She laughed when I asked. A real laugh, like the question itself was funny.

“I’m not motivated,” she said. “I just have a plan.”

That felt like a cop-out, like something you say when you don’t want to explain the real answer. But the more she talked, the more I realized she meant it literally. Motivation, for her, isn’t the starting point. It’s what shows up after she’s already begun, and she figured out a long time ago that waiting for it to arrive before she started was a losing battle.

She told me about a goal she’d had for a while, something she really wanted and thought about constantly. And then, just didn’t do it. Months went by and the longer she waited, the further back the starting line got, until she finally decided that waiting to do it “right” was costing her more than starting and doing it “badly”. So she started. Ten minutes. That was it, just ten minutes of actually doing the thing. She told me she scoffed at herself, “how is ten minutes going to do anything?!”

I asked her, “okay, so did you think the same thing after just 10 minutes of work?”

She replied, “No, and I was shocked. At the end of those ten minutes I felt something I hadn’t felt in a while. Proud. Not of what I’d made, but that I’d finally moved. And that feeling made me want to come back the next day.”

And that’s the ticket. Progress doesn’t have to be a leap. It can be embarrassingly small, but it counts. Small progress creates a feeling that makes you want to come back, and coming back is what compounds. Ten minutes became fifteen, fifteen became thirty, she started gaining momentum, momentum meant she wanted to spend more time on it, more time meant more visible progress, and eventually she looked up and she was there.

But she made a mistake.

She didn’t have a plan for after. She hit the goal, felt great, and but didn’t think about what it would take to keep it. Things started slipping. Slowly at first, then faster, until enough time had passed that she admitted she’d lost most of what she’d built. “The come down after accomplishing something,” she told me, “is one of the sneakiest motivation killers there is.”

If you don’t know what you’re going to do after you cross the finish line, hitting the goal can actually bring you to a screeching halt. So now when she sets a goal, she also thinks about what comes next. Sometimes that’s a new goal, sometimes it’s a maintenance goal, but either way, it’s a clear picture of what holding the ground looks like, and what it would cost her if she didn’t. She’s still working on getting back to where she was, the difference is now she knows what she’s doing when she gets there.

When I asked her what the actual system looks like day to day, she was pretty specific about it. She has a big picture goal in mind, including when she wants it done, and writes it down, breaking out milestones. She spends time at the beginning of each month and sets up her schedule to accomplish one of those milestones, or even part of one. And she’s ruthlessly honest about her energy. She knows there will be days when she’s just too tired or there’s too much going on with the kids or family is coming in town, etc…, so she literally schedules “no work” days. And if there needs to be a lot of those, she readjusts her goal.

This is true in reverse as well. It helps her set boundaries with life outside work. If she needs to get something done, she doesn’t have to think about whether she can bake cookies for the PTA. She just looks at the calendar and says no. No thinking about. No shame. No overcommitting. She’s learned from experience that putting something on the calendar she won’t do just means she’ll feel awful about it later. And feeling awful is the opposite of motivating.

“When I don’t do those things,” she said, “everything falls apart the same way every. time. Deadlines sneak up, I’m disorganized, the work gets messy, the STRESS piles up, and then it’s harder to get back on track, which makes me feel worse, which makes me want to not do it at all.” She called it the shame loop, and she said it will eat you alive.

I learned a lot talking to her, but the biggest impact was realizing the being motivated isn’t a personality trait. She said she’s watched people with almost no natural drive build amazing things. And she’s watched people who seemed endlessly fired up flame out because the fire was the whole system, and fire runs out.

“Motivation isn’t real,” she said. “Progress is.”

Here’s the thing you want:

You want to stop feeling like the people around you have something you don’t, like there’s some internal engine running in other founders and builders and that yours is missing or sprung a leak.

You want to get out of the shame loop, the one where you don’t start because you don’t feel motivated, feel bad about not starting, which makes it harder to start, and by the time you go to bed you’ve convinced yourself you’re falling behind and maybe you’re not cut out for this.

You’re not broken. You’re not behind. And the motivation you think you’re missing probably isn’t what’s actually standing between you and moving forward.

Here’s how to do it:

Stop waiting for the feeling. Build the plan instead.

The plan removes confusion that kills momentum before it starts. Big picture first: what do you actually want to accomplish and by when. Then break it into monthly goals. Weekly and daily if you need to. The key word is honest. Not aspirational, not what you’d do with unlimited time and perfect energy. What you can actually do given your schedule and your life as it is right now.

Then protect the time. Put it on the calendar before the week gets away from you. And on the days where you know you won’t have the bandwidth, don’t schedule work. A plan you’ll actually follow beats a perfect plan you’ll ignore every single time.

The cool thing is that the plan can always change. Life transition, change your goals. Realize that you weren’t right about how long one part will take, adjust the timeline, if something comes up and you can’t accomplish what you wanted that day, don’t be too hard on yourself. Life is going to happen, it’s OK to let it. Adjusting your plan doesn’t equal failure. It’s just part of the plan.

First step, start with something small. Small enough that you almost don’t even want to tell someone. One email. One paragraph. One corner of the desk. Our brains are naturally wired to avoid doing something hard, and if it feels big or heavy or unclear, your brain will win. But if the thing is small enough, there’s no friction, you’ll do it, and doing it is what starts the engine. It also helps to keep the end goal visible. Don’t write a plan and then stick it in a drawer. Tape it to your monitor, put it on your fridge, your bathroom mirror. Remind yourself as often as possible where you’re headed. A maybe even put affirmations or motivational sticky notes somewhere. It may be cheesy, but it works when you’re feeling like you’re in the trenches

When you hit the goal, don’t stop. Think about what comes next before you get there. Set the maintenance goal. Write down what it would cost you if you didn’t. That part matters more than most people think.

Here’s why it works:

When you stop waiting for motivation and start treating progress as the thing that creates it, the shame loop loses its grip. You don’t need to feel a certain way to take the next step, you just need to know what it is and and make it small enough that its not intimidating. The plan removes the confusion, the small step removes the resistance, and the progress that follows is what brings the feeling back. It’s more honest too. You’re not pretending you’ll wake up fired up every day. You’re building something that works on the days you don’t.

Now go:

This week, try this: Block 30 minutes, not to do work, but to map it. Write down the one thing you’re trying to accomplish in the next 30 days, then work backwards. What needs to happen this week for that to be possible? What needs to happen today? Be honest about your schedule and don’t put things on days where you know you won’t have the bandwidth.

Start here if you only have 10 minutes: Open your calendar and find three blocks this week where you can realistically do focused work. Block them now, before you do anything else. Don’t figure out what you’ll work on yet, just protect the time. That’s enough for today.

P.S. I know I want to consistently send out a newsletter. I know I need to write them. Sometimes, I just don’t have the bandwidth and feel bad about not getting to it sooner. Apparently I needed to take my own advice. But that’s kind of the whole point, isn’t it? Even the people writing about motivation are in the trenches with you. Some days I genuinely cannot find the gear, and the only thing that gets me going is remembering that doing something small today is always better than waiting until I feel ready. I’m still learning that. Probably always will be. But every time I take the small step, I remember why it works, and that’s usually enough to take the next one.

If this resonates, hit reply and tell me where you’re stuck in this transition. I read every response.

Writing from Austin, still building the plan,

Alex

We also work with founders and teams on ghostwriting and go-to-market support—helping turn ideas into clear content for positioning, launches, and distribution.

If that’s something you’re thinking about, happy to chat. Feel free to put some time on my calendar here.

Haley told her potential employer this upfront, “I’ve been around long enough to know what bad looks like and I’m not doing it again.”

Her soon-to-be new boss told her they were really proud of their culture. That it was one of the best. That it wasn’t a branding exercise, it was real. So, she did what any smart person would do. She talked to people on the team when the boss wasn’t in the room. She said everyone told her the same thing. The flexibility was real. The support was real. The expectations were high but fair, and they were happy to be a part of the team.

She was genuinely excited and said for the first few months, it was everything they said it would be.

Then, things ACTUALLY got real. She explained, “The blend of in-office and WFH I was promised turned into five days a week in the office. I wasn’t supposed to work on weekends, but it slowly evolved into working most evenings and weekends. The technical manager was fired, and his workload got handed to me, on top of the job I was hired to do. Without a conversation. Without a title change. Without additional compensation. And when I finally told him the workload was too much, he told me I just needed to get better at my job.”

Haley also has a child with disabilities which means leaving early or staying home more than a typical parent would. She was promised flexibility, but after a while she said her her inability to be there every day was “ruining her reputation and people couldn’t rely on her.”

“I was crushed.” she said. “It felt like everything I’d worked for in my career was dismissed in a single sentence.”

In the end, she was let go under an assumption that wasn’t true. Her boss even told her, “I don’t even need to hear the whole story.” This was after almost 2 years of her time.

Haley told me, “Hind sight’s 20/20. I should’ve noticed it so much earlier. The turnover was really high; he actually let someone go just 3 days after being hired. He kept toxic employees that did everything he asked but who slowly ruined the team when he was gone. And the hardworking people, he always ended up letting them go.”

There were free snacks in the kitchen. A gym in the building. Annual team retreats. Monthly town halls. All of it looked right. It wasn’t. not even close.

She said, “It was one of the most elaborate fake cultures I’ve ever encountered.”

After our conversation, it made me think about how often founders talk to me about their own company’s culture. They either want to make sure they create a good one or need help figuring out how to fix it.

Here’s the thing you want:

You want to build something people are genuinely proud to be part of, where nobody’s updating their LinkedIn on a Tuesday afternoon because they’re miserable.

Most founders want that. The problem is the ones who don’t have it usually think they do, and the gap between what they say their culture is and what people actually experience is where their company quietly fall apart. High turnover, disengaged teams, people doing the bare minimum, good people leaving for no obvious reason — that’s not a hiring problem or a compensation problem, that’s a culture problem.

“ Corporate culture is the only sustainable competitive advantage that is completely within the control of the entrepreneur.” — David Cummings, Co-founder of Pardot

Here’s how to do it:

Define your culture by what you do, not what you say. You can put your values on the wall. You can send the all-hands email. You can have 1:1s and coach people. None of it matters if your highest performer treats people like crap yet you keep promoting them. When you do that, what you’re actually telling your team is values are decorative and performance is the only currency that matters.

When a founder says they care about work-life balance and then sends a Slack message at 11pm and expects a response or says they value transparency and then makes major decisions without explanation, people lose faith. It only takes a few inconsistencies before the trust is gone, and once it’s gone you’re not getting it back by throwing a company retreat at it.

Be 100% honest about what the job actually is before someone takes it. Not the aspirational version, the realistic version, including the parts that aren’t great. When you don’t clearly define the role or expectations, you’re not just disappointing people, you’ve made them feel lied to. People can handle hard things. They usually don’t tolerate handle being misled.

Don’t tolerate poor behavior. Fire someone for violating company values the same way you’d fire for under-performance. Most founders never do this because a violation of cultural expectations can be really hard to quantify. They’ll let someone go for missing targets but keep someone who’s making people miserable.

We all know when you have to let someone go who is genuinely great at their job, it’s easy to hesitate. They can do things nobody else on the team can do, they’re fast, clients love the output, and losing them feels like a real business risk. But they’re dismissive of people who disagree with them, they cut corners on the work that isn’t exciting, and the people around them start to either retreat or leave. Maybe you think the output justifies the behavior. It doesn’t.

Cutting toxic employees, regardless of their skills is always the right move. — Gary Vaynerchuk

Listen and pay attention to the culture people are experiencing. You can usually tell you have a bad culture even if you don’t want to admit it. Yea, the gym and the snacks and the team trip, those things are great, but it’s just marketing; it’s what the culture looks like from the outside. What it should feel like on the inside is that managers actually have their team’s back when things go sideways and people are trusted to do the job their job with being micromanaged. But if you actually listen to people in your 1:1s and they’re telling you differently, you need to address it immediately.

The uncomfortable truth. Many founders don’t understand that people who work the hardest aren’t the ones you pressure into it, they’re the ones that do it because that’s who they are. Those are the people you want on your team, but they’ll only stay as long as they feel trusted, supported, and not taken advantage of. Their work may be slow at times, but unfortunately, most founders don’t have the patience for slow when they’re trying to grow fast.

And you can’t measure commitment to the company by how much you’re willing to sacrifice for it, and then use that as the standard for everyone else. That’s the thing founders miss most often: your tolerance for the grind is not a baseline. It’s just yours. Expecting your team to care as much about the company as you do is a losing strategy. The company is your baby, the weight of success or failure is ultimately on you. Not them. So don’t expect them to act like it is. Respect their boundaries, and then success is far more likely.

One more thing worth saying: the culture you build in the first ten people is almost impossible to change at fifty. Not because people resist change, but because culture is self-selecting. The early team attracts the next wave, and if they’re burned out, cynical, and keeping their heads down, that’s what you’re recruiting into. I’ve seen founders try to fix culture at scale and it’s brutal, not impossible but brutal, because you’re essentially asking people to unlearn the survival behaviors they developed working for you.

The time to get this right is before you think you need to.

Now go:

This week, try this:

If you haven’t specifically thought about what culture you want for your company, start there first. Write a few things down about how you want your company to feel to others. If you already think you know that, think about one person on your team who is high output but low culture fit. Not someone you’d call a bad person, just someone whose behavior, if everyone on the team behaved the same way, would make the company worse. Write down what you’re tolerating and why. Then ask yourself if you’d hire someone today knowing they’d behave exactly that way. If the answer is no, you already know what to do.

Start here if you only have 10 minutes:

Ask one person on your team, someone who isn’t a direct report and who you know will tell you the truth. Ask them how they’d describe the culture to a friend who was thinking about joining. Don’t prompt them, don’t lead them. Just listen. What they say will tell you more than any engagement survey.

Next Tuesday: The Genius Guide on When to Pivot and When to Move on

P.S. The hardest part of building a real culture isn’t making sure you’re providing all the bells and whistles, it’s being honest about any gap between what you say and what people are actually experiencing. Several founders I know have had moments where someone on the team finally told them the truth and realized they’d been the problem the whole time. That’s uncomfortable. It’s also the only way you actually fix it.

If this resonated, hit reply and tell me what your culture looks like on paper versus what it looks like in practice. I read every response.

Writing from Austin, still learning and listening,

Alex

We also work with founders and teams on ghostwriting and go-to-market support—helping turn ideas into clear content for positioning, launches, and distribution.

If that’s something you’re thinking about, happy to chat. Feel free to put some time on my calendar here.

She tried building a business as a photographer and stopped, then she tried again and stopped again.

Every time I’d ask her what was going on I’d get some version of the same answer: there were already so many photographers, everyone had a good camera on their phone now, who was even going to hire her over someone with more experience and an established name.

She’d spiral through all of it and talk herself back to the starting line before she ever ran the race, she’d find a niche she thought nobody was touching, pour energy into it, get some encouraging feedback, and then hit a wall when people weren’t quite ready to let a stranger into that part of their story, and that was it for her, she stopped trying to find another way in.

She never fully committed, and today she’s not a photographer, and what makes it sting is that since she first started dipping her toe in the water she’s watched so many photographers dive in and build something real.

I think about her story a lot because the thing that stopped her wasn’t the market, it was the story she told herself about the market.

Here’s the thing you want:

You want to build a business and stop thinking there’s no space in the marketplace for what you have to offer.

You want to stop the repeat cycle of trying and then circling back to start again, and somewhere in the back of your mind you already know that a crowded market simply means a product is in demand and all you need to do is figure out what’s going to make customers buy YOUR product instead of someone else’s.

Here’s how to do it:

A saturated market isn’t a bad thing, it just means that step one is already taken care of and you don’t have to test the theory that people want something because it’s already proven. It’s a demand signal and a lot of people are paying for it, the only real question is whether you can give them a reason to want it from you.

“Every market is saturated. The only question is whether you're remarkable.” - Nicolas Cole, entrepreneur and writer

My friend’s fatal mistake wasn’t that she picked a competitive space, it was that she kept trying to compete on the same terms as everyone else, and when her first attempt at differentiation didn’t immediately stick she concluded the whole market was the problem instead of just that one angle. Saturation doesn’t mean no room, it means no room for another version of the same thing, and that’s a different problem, a solvable one.

When I was building in a space that felt genuinely overrun, things shifted for me when I stopped trying to appeal to everyone who might possibly want what I was selling and started getting really specific about who it was actually for. Who is this person at exactly this moment in their life, what have they already tried, what about it isn’t working, and how can my product solve that problem for them?

When I got that specific, the market didn’t feel saturated anymore, it felt like I finally knew where I was standing in it.

The photographers who built real businesses in my friend’s city weren’t doing something she couldn’t do, many were objectively less talented, what they had that she didn’t was a committed point of view. One of them only shoots families during major life transitions like moving, new babies, kids leaving for college, she charges more than almost anyone in her area and has a waitlist. Another one built hers around making introverted people feel at ease in front of the camera, that’s her entire brand, she talks about it constantly, and she stays booked. Neither of them is trying to be everything to everyone, they both made a choice about who they were for and then they showed up for those people consistently until it compounded.

The thing I’ve seen derail founders in crowded markets is they confuse the discomfort of not being the best known option with evidence that they can’t win, and these are not the same thing. Every business that exists right now entered a market where something else already existed, Google wasn’t the first search engine, Slack wasn’t the first workplace communication tool, the question was never whether the space was occupied, it was whether they had something genuinely better to offer a specific set of people and whether they were willing to be patient enough to let that play out.

What I’d tell my friend now if she were still trying is that her first niche idea not working wasn’t a sign that the market was full, it was data, it told her something specific about that particular audience that she could have used to find the next angle. Instead, she let one failed attempt become a verdict on the whole thing, and that’s the part that actually cost her.

The hard truth for a lot of people is that market saturation is often just an excuse for an underlying problem, confidence. She was using the market as cover for not thinking she was good enough and the lack of confidence was feeding the market anxiety, and neither one ever got addressed directly because she kept running the same loop. When you’re confident in what you have and you commit even imperfectly, market feedback stops being scary and turns into something you actually want to hear, you’ll still feel vulnerable but when you can stand tall and push through that discomfort you’ll get something real to iterate on instead of just a fear to manage.

The people who succeed in saturated markets aren’t usually the most talented or the most innovative, they’re the ones who were confident in what they had, stayed in long enough to learn from the friction, and didn’t let one thing not working become a reason to stop trying other things.

Obstacles don’t have to stop you if you run into a wall. Don’t turn around and give up. Figure out how to climb it. Go through. Or work around it. - Michael Jordan

Here’s why it works:

When you stop trying to shout at everyone in the room and start talking directly to one specific person, the competition mostly disappears, not because the other people are gone but because you’re focused on your conversation. When you’re talking to a smaller group of people you get better feedback faster, they either convert or quickly tell you exactly why they didn’t, and that information is worth more than any amount of time spent worrying about how crowded the space is.

The confidence problem quietly solves itself too because you’re measuring success against the specific problem you’re solving for a specific person instead of trying to solve every problem for everyone, and that’s a much more winnable game.

Now go:

This week, try this:

Write down exactly who your most specific possible customer is, not a demographic, a situation. What have they already tried, what didn’t work about it, what are they actually frustrated by right now. Then look at how you talk about what you do and ask yourself honestly whether that specific person would read it and feel like you were talking directly to them. If not, that’s your first thing to fix.

Start here if you only have 10 minutes:

Find one competitor who is winning in your space and figure out who they’re NOT serving. Not who they’re ignoring on accident, who they’ve structurally opted out of by the choices they’ve made. That’s your opening.

Next Tuesday: The Genius Guide to Staying Motivated

P.S. The thing I never said to my friend and probably should have is that the market was never the real obstacle. She was talented, she had good instincts, and she found a real gap on her first try even if the timing wasn’t right. I should have told her that committing, iterating, and staying in long enough is the secret sauce, I wanted her to be successful and had I known it was just her thinking she wasn’t good enough I could’ve been a louder cheerleader and encouraged her to keep going. Saturation doesn’t stop the people who decide to stay in the game, it just thins out the ones who were looking for a reason to leave.

If this resonated, hit reply and tell me where you’re stuck. I read every response.

Writing from Austin, still backing people who bet on themselves,

Alex

We also work with founders and teams on ghostwriting and go-to-market support—helping turn ideas into clear content for positioning, launches, and distribution.

If that’s something you’re thinking about, happy to chat. Feel free to put some time on my calendar here.

1. Here’s the thing you want: You want to build something real, something that works, something people actually use, something you’re proud of when you talk about it at dinner without needing to mention a valuation to make it sound impressive. You got into this because you believed in something, because you saw a problem worth solving or a product worth creating, and that instinct was right. The question is whether you’re still building toward that or whether somewhere along the way the goal quietly shifted from making something good to making something that looks like it’s going to be enormous, because those are two very different things and they pull you in very different directions.

2. Here’s how to do it: When I was at Techstars, the MD Amos used to say the same thing over and over and it took me a while to really hear it: test your theories, understand what levers you can pull to push the business just a little further, know your financial structure, know your forecast, find what works then find what works a little better and keep going. He wasn’t talking about hockey stick growth or Series A timelines, he was talking about the unglamorous brick by brick work of figuring out if your idea actually holds up when real people interact with it. The founders I watched struggle were almost always the ones who skipped that part, great pitch deck, inflated numbers, sometimes no real MVP, sometimes no tested theories at all, just an idea dressed up to look like a business because the timing felt right and the trend was hot. I get it, because when everyone around you is talking about disruption and the room is full of that electric energy, it’s genuinely hard to be the person who says “we actually need more time,” it feels like you’re losing a race that everyone else is running and winning. But most of those people weren’t building companies, they were pitching stories, and stories without foundations eventually collapse and everyone in them pays for it, the founder, the team, the investors, and oftentimes the customers.
   

   I met a guy in 2017 who was just starting out, bootstrapped from day one, no outside money, no splashy press, no valuation conversations, he just kept plugging away day by day, year by year with the same integrity and patience he had at the start. He still isn’t the biggest and the best and you probably haven’t read about him anywhere, but he owns 100% of his company, he has a great team, a great culture, and a product people genuinely want that’s still trending up. His vision and his patience got him there, not suits and newspaper articles stroking his ego, and he’s one of the most respected people I know in this startup space because he built that reputation by actually doing the work. Quiet steady success is still a win, a business that grows sustainably that you control and reflects the thing you originally set out to accomplish. That’s not a consolation prize, it’s actually the goal, it just doesn’t photograph as well.

   

   
   The numbers make this pretty clear if you’re willing to sit with them; about 90% of startups fail, making it to unicorn status has a 1-2% chance on a good day, and less than 0.7% of unicorns ever achieve sustained revenue. After ten years the failure rate for unicorns sits somewhere between 30-40% compared to 10-15% for smaller more sustainable ventures, so the question isn’t whether unicorn status sounds exciting, it’s which group you actually want to be in.
   
   There’s also a version of this nobody talks about because it’s uncomfortable: when you take on the kind of money that comes with unicorn expectations you trade something, you trade control, you trade the ability to make your own decisions about where the company goes because now there are people in the room who need a very specific kind of win and they will push for it even if it’s not what you need. You and your investors can become completely misaligned; you want a good product and a sustainable business, they want an exit, and that tension doesn’t just create friction, it can stall everything you’ve worked for. The dilution alone can be enough to make you feel like a stranger in your own company. Good investors ask hard questions and want real answers and they’re patient because they understand what it actually takes, and the ones chasing fast growing companies on a wing and a prayer will push you in ways you didn’t expect and didn’t sign up for because they’re panicking. And panicking investors make everything harder.

   

   
   The other uncomfortable truth is this: entrepreneurship isn’t for the faint of heart, it’s hard and the odds are against you, and that’s okay to say. If you’re not willing to take the time to build something well, to build it with integrity, to sit in the uncertainty long enough to figure out what actually works, this is a hard road. If big money is your number one motivation or you’re driven by the buzz, you often won’t get very far because the money actually follows the work, not the other way around. Your ego will tell you you’re the exception, of course you’re going to be the unicorn, disrupt the market, solve all the problems of the industry, it tells everyone that because if it didn’t no one would probably even start a business. But most of the time when you chase the wrong things for the wrong reasons, you won’t realize you’re not where you wanted to be until you’re already too deep in.

3. Here’s why it works: When you stop chasing unicorn status and start building something sustainable, you keep control of your company and your vision, you make decisions based on what’s actually working instead of what looks good in a pitch deck, you avoid the dilution and misalignment that comes with taking on investors who want an exit more than they want a good product. You build something that lasts instead of something that burns bright and collapses, and you get to be proud of what you made instead of explaining what happened to it.

   ---

   “How you climb a mountain is more important than reaching the top.” — Yvon Chouinard, Founder of Patagonia

4. Now go: This week, try this: Write down why you started, not what you’re building but why. Then write down what your average Tuesday actually looks like right now, the real one not the highlight reel version. Ask yourself if those two things are still pointing in the same direction, if they are, keep going, but if they’re not that’s important information.

Start here if you only have 10 minutes: Find one founder you know who’s built something slowly and well, not a unicorn, not a headline, just someone who’s still standing after ten years. If you don’t know anyone read about one. Their stories will tell you more than any pitch competition recap ever will.

Next Tuesday: The Genius Guide to Dealing with Market Saturation

P.S. The thing I keep reminding myself is that 1% better every day compounds into something real; it’s not flashy, nobody’s writing about it, but it adds up and it lasts, and at the end of it you still recognize what you built and that matters more than I used to think it did. If this resonated, hit reply and tell me where you are in the building process. I read every response.

Writing from Austin, still betting on the builders,

Alex

Not kidding. Three months on branding, fonts, photos, messaging, the whole identity of this new business I was launching. I was choosing new color palettes every other week it seemed. And I rewrote the homepage copy probably 40 times because I wanted it to feel just right.

When I finally launched, finally started talking to actual people about it. They loved the idea, they said it was brilliant, they told me exactly who they think would and should buy it.

Then they didn’t buy it.

And then those other people they talked about, they didn’t buy it either.

The whole thing needed to pivot, which meant all that time perfecting the brand, obsessing over the messaging, getting everything perfect was basically wasted. I could’ve learned this in week one if I’d just put something ugly out there and started talking to people.

I see this happen over and over. Founders with legitimately great ideas who never get off the ground because they’re caught in the trap of figuring it all out before they launch. Brainstorming session after brainstorming session, trying to anticipate every possible user thought, building the roadmap to perfection, adding just one more feature before they’re ready and nothing ships.

The team gets frustrated because nobody knows what they’re actually working toward. Months go by and you’re still in the same place, just with a longer feature list and more reasons why you’re not ready yet.

You’re just never going to know if your theory is right until you test it. And the only way to test it is to put it out there and see what happens.

1. Here’s the thing you want:

You want to be successful. You want to be able to launch something you feel proud of.

You want to know what users want, what they’ll pay for, and you want a gold star next to your name.

You’re stuck in build mode, and what you need is to figure out how to get past it. Then, you’ll get what you want.

2. Here’s how to do it:

Get it to 80% and launch it.

The way to get started is to stop talking, and begin doing. - Walt Disney

Not 95%, not “just need to add this one thing.” 80%. Good enough that it demonstrates the core idea, rough enough that you’re not devastated about changing it.

Then get feedback, adjust, launch again. Keep doing this until you start to understand who your actual customers are, what they actually need, and what they’ll pay for.

I learned this the hard way with that business I mentioned. Three months on branding and positioning for something nobody wanted to buy.

When I finally pivoted, I did the opposite. I threw together something basic, reached out to five potential customers, walked them through it, and asked if they’d pay for it. One of them said yes immediately, two of them told me they like it but why it wouldn’t work for them at that time, and the other two said they could share it with other people they think would buy it. Suddenly I had actual information instead of theories.

The version I launched after those conversations looked much different than the original, but it was the right version because it was informed by reality instead of assumptions. And I then understood that each version after would get me a little closer to the goal line.

I’ve watched this play out with other founders too. Worked with a team once where we had meeting after meeting theorizing about the user experience, trying to sequence features perfectly, debating which user flow would be most intuitive. We weren’t making any real progress. The founder kept saying “we just need to think through this one more scenario.”

Eventually I asked, “What if we just launched what we have?” The founder didn’t. I left the team and never saw him launch anything. All that time. For nothing.

On the flip side, I worked with a founder who spent the time getting it perfect…. Well, perfect according to her. After she launched and got feedback, she didn’t listen to it because she was so attached to what she built and how much time and energy she spent. She was convinced it was the perfect product. Despite what people were telling her, she didn’t want to feel that time was wasted and it was harder to change the path forward, harder to meet her customers’ needs and solve their problems. 10 years later, she’s still stuck that mindset, running out of money and can’t get funding because she doesn’t have much growth compared to the time spent building it.

The ticket to just launching it is knowing it’s a litmus test. It’s not the end-all, be-all. The first version doesn’t need to be perfect. It won’t be what defines you for years to come and it doesn’t have to be your gold star. You’ll be able to make changes, smarter decisions, alter course. You just have to know what turn to take and why. Referring back to last week’s topic, just launching it requires being ok with not knowing, being comfortable making decisions with incomplete information and adjusting as you learn.

You probably already know this and it’s exactly why you’re not launching, but in case you don’t, know this is going to be uncomfortable.

Founders tend to wrap their whole identity around their product and how people respond to it. You might be embarrassed or feel like you got punched in the gut when you get feedback you don’t like. And you will.

You’ll probably also lose customers along the way. Some people may like the first version and not the second or vice versa but not everyone can be in love with what you build.

Your most unhappy customers are your greatest source of learning. - Bill Gates

Just remember that it’s not about appealing to all customers, it’s about appealing to the right ones. Despite what you feel, the successful founders know this. They put their egos aside and just go for it.

3. Here’s why it works:

You stop wasting time on things nobody wants.

When you launch at 80% instead of waiting for perfection, you find out quickly if you’re building in the right direction. You might discover, like I did, that your theory was completely wrong and you need to pivot. That’s not a failure, that’s information. And getting that information early means finding success earlier.

You can theorize all you want about who your ideal user is and what they need, but until you test it on real people, you don’t actually know. Launching means you start building on reality, not just a good idea.

Move fast, fail fast, and fail forward until you get to the thing that works.

Every launch is progress. You’re moving forward, learning, iterating. That momentum keeps your team motivated and keeps you from getting trapped in endless planning cycles.

You get better at the things that actually scale. Launching and iterating teaches you about positioning, messaging, customer development, all the stuff that actually grows a company. Building in isolation just makes you good at building in isolation, which doesn’t help when you eventually need to sell the thing you built.

4. Now go:

This week, try this:

Pick one thing you’ve been perfecting that’s at least 80% done. Launch it this week, even if it feels rough. Get it in front of five real users, ask them what they think, watch how they actually use it instead of how you thought they’d use it. Document what you thought would happen and what actually happened.

Then adjust and launch again in a couple of weeks. Don’t wait until it’s perfect, just make it 10% better based on what you learned and put it back out there.

Start here if you only have 10 minutes:

Look at your calendar for the last month. How many hours did you spend in planning meetings vs. actually testing things with real users? If the ratio is heavily skewed toward planning, that’s your problem.

Block two hours this week to put something in front of someone outside your team. Doesn’t matter if it’s polished, just needs to be real enough that they can give you actual feedback instead of theoretical opinions.

Next Tuesday: How to be OK with Not Being a Unicorn

P.S. The hardest part about launching before you’re ready isn’t the work, it’s the emotional hit when you get feedback you don’t want to hear. That feature you spent weeks building that users don’t care about, the positioning you crafted that doesn’t resonate, the whole approach that turns out to be wrong. It feels like failure, and your instinct will be to retreat back into build mode where it’s safe and you don’t have to face reality. But getting that feedback is actually the win. Now you know. Now you can fix it. The only real failure is never launching at all because you were too scared to find out if you were wrong. If this resonates, hit reply and tell me what you’ve been sitting on that needs to ship this week. I read every response.

Writing from Austin, learning in public,

Alex

That was my friend Lauren Hoffmaster several years ago. She’d just moved to Austin after completely pivoting her career to work in startups following 10 years in big oil and gas, trying to prove to everyone who thought she was crazy that she was right for making the move.

“Did you prepare for the interview?” I asked her.

“Not really,” she laughed. “I didn’t reach out to people for advice before the interview, and then I was so nervous that whatever I said probably had nothing to do with my actual resume or accomplishments, I just know I was sweating through my shirt in that coffee shop and hoping he couldn’t tell.”

She got the job anyway but not because she fooled him, she said she was just lucky that he took a chance on her. A few months later he told her she should be in an executive position based on the value she brought to the table, but also told her point blank that her interview was terrible and he had no idea what she was really capable of, and she said he was absolutely right on both counts.

I’ve had interviews like that, where I walked out thinking I’d completely bombed it and somehow still got the job, and it’s wild how often the thing we think disqualifies us doesn’t actually matter as much as we think it does because people are still willing to take a chance on someone who doesn’t know everything yet.

1. Here’s the thing you want:

You want to feel confident when you step into something new that you’re not sure you can handle, when you’re leading a team for the first time, when you’re pitching your business to people who seem way more accomplished than you.

You want to walk into those rooms with all the answers and know exactly what to do in every situation, you want to feel certain about your decisions even when the information is incomplete, you want to stop feeling like a fraud and stop pretending you understand things you don’t actually understand yet.

That’s not how it works most of the time, and the sooner you accept that not knowing is part of the job, the sooner you’ll actually become effective at what you’re doing and gain confidence because of it.

2. Here’s how to do it:

Everyone is operating with incomplete knowledge, even the people you think have it all figured out. The CEO who seems certain about their decisions is making calls with missing information all the time, the colleague who sounds authoritative in meetings might be winging half of it, the person who just got promoted is dealing with a learning curve they didn’t expect.

“Just because you are CEO, don’t think you have landed. You must continually increase your learning, the way you think, and the way you approach the organization.” — Indra Nooyi, former CEO of PepsiCo

The people who seem the most confident aren’t the ones who know everything, they’re the ones who’ve gotten comfortable with not knowing and are okay saying so.

I asked Lauren what it was like when she got her first executive level job.

“I felt like an imposter every single day,” she told me. “My reputation was on the line, my team was watching to see if I could actually lead them, my boss needed to know he’d made the right call, and every time I had to speak in front of people my voice would shake and my heart would pound so hard I thought everyone could hear it. I kept thinking, are they going to figure out how much I don’t know, are they going to realize I’m in over my head, what the heck am I doing here?”

The worst part, she said, was feeling like she had to hide it, like admitting she didn’t know something would prove she didn’t deserve to be there.

I’ve been in rooms where I was terrified someone would ask me a question I couldn’t answer and I’d spent so much energy trying to look like I belonged that I couldn’t actually focus on doing the work.

“So what changed?” I asked.

The turning point came when she started noticing that the leaders she respected most were the ones who would say things like “I don’t know enough about this yet, can you explain it to me” or “I’m not the expert here, what do you think we should do.” They weren’t pretending to know everything, they were honest about their limitations, and that made people trust them more, not less.

So she started experimenting with it, in meetings when someone brought up something she didn’t understand, instead of staying quiet she’d say “I’m not familiar with that, can you break it down for me,” when her team asked her about a decision, instead of making something up on the spot she’d say “I need to think about this more, let me get back to you tomorrow,” when her boss asked about an area she had no experience in she’d say “I honestly don’t know the best approach here, but here’s what I’m thinking so far….”

“And what happened when you started doing that?” I asked.

“People didn’t lose respect for me, they gained respect for me,” she said. “My team started coming to me with problems more often because they knew I’d give them an honest answer, my boss started trusting my judgment more because he knew I wasn’t going to pretend, and I started making better decisions because I wasn’t wasting energy on maintaining a facade.”

When you’re honest about what you don’t know, you build more credibility than if you fake your way through it, because as good as you think you are at hiding it, people can usually sense you’re not being genuine.

Every time she admitted she didn’t know and asked for help, it opened up a conversation that made her better at her job, and she found that people were excited to help, they wanted to share what they knew, and they respected her more for asking.

I wanted to know if she had a specific example of when this actually worked, when the stakes were high and being honest about not knowing something helped her succeed.

She told me about a case she had to present to executives on a topic she didn’t have much experience in, where a negative outcome would have severely affected the person she was defending.

“Part of what made me successful was admitting to myself I didn’t know,” she said. “It motivated me to prepare like crazy, research more, learn more, forced me to reach out to people who understood the topic better than I did, show them what I learned and ask for help to make it better. I was under a lot of pressure to get it right, and simply asking for advice or a general overview wasn’t gonna cut it, but because of my initial research, they gave me detailed insights I never would have found on my own, they pointed out things I was missing, they helped me understand nuances I didn’t know existed, and because of that I actually had a deep understanding of the topic that I would have never learned that quickly on my own.”

We think asking for help makes us look weak but it’s actually what makes us effective, and if you do some due diligence first, the help you get is even more valuable.

I then asked, “What was it like when you actually got into the room?”

“My hands were shaking and my mouth went dry,” she admitted. “But I had done the work, I had admitted what I didn’t know, I had asked for help, I had filled in as many gaps as I could, and when I didn’t have an answer I was able to confidently tell them I didn’t know but that I would find out.”

She won that case, not because she knew everything, but because she was honest and prepared.

The other thing that helped her get comfortable with not knowing was realizing that certainty is often an illusion anyway, even when you think you know something, circumstances change, new information comes in, what worked before stops working. The best leaders are the ones who can make decisions with incomplete information, course correct as they go, and admit when they were wrong.

“I learned that you can be comfortable with uncertainty, and that’s when you can make the best decisions.” — Mary Barra, CEO of General Motors

“What would you tell someone who’s in that position right now?” I asked her. “Someone who’s leading a team or stepping into a new role and feels like they don’t know enough?”

She thought about it for a second. “Not knowing doesn’t mean you’re not qualified, it means you’re still learning, and learning is literally part of the job. Every time you step into something new there’s going to be a learning curve, you’re not gonna know it all even if you’re experienced, and that’s normal. The question isn’t whether you know everything, the question is whether you’re willing to figure it out, whether you’re asking the right questions, whether you’re confident that not knowing is okay.”

Being confident that not knowing is okay, that’s the whole thing.

3. Here’s why it works:

When you stop pretending and start asking, you make better decisions because you’re working with real information instead of assumptions. You build trust because people know you’ll give them honest answers instead of performing competence. You learn faster because you’re not wasting energy on maintaining a facade. You become the kind of leader people actually want to follow, not because you have all the answers, but because you’re honest about the process of finding them.

4. Now go:

This week, try this:

Pick one thing in your current role that you don’t fully understand but have been pretending you do. Find someone who knows more about it and reach out, see what happens when you stop hiding what you don’t know and start asking for help instead.

Start here if you only have 10 minutes: In your next meeting or conversation, the next time someone brings up something you’re not familiar with, instead of nodding along speak up and say “I’m not familiar with that, can you explain it?” Notice how it feels and notice how people respond.

Next Tuesday: The Genius Guide to Just Launching It

P.S. After talking to Lauren, I realized I still find myself pretending I know things I don’t, still worried that admitting I’m uncertain will make me look incompetent, but the confidence doesn’t come from knowing everything.

It comes from being okay with not knowing and being honest about it.

If this resonates, hit reply and tell me about a time you pretended to know something you didn’t. I read every response.

Writing from Austin, where we’re all figuring it out as we go

Alex

Not the kind where you don’t have friends or family, the kind where you’re surrounded by people, but nobody actually gets what you’re going through. The kind where you have to have it all together in public, but behind closed doors you’re scared and alone and don’t know who you can actually talk to about it.

I remember sitting in my apartment a few years ago after a particularly brutal week, staring at my phone trying to figure out who I could call. I had friends, I had family, I had a team, but I couldn’t call any of them about what I was actually feeling because none of them would understand.

My friends would tell me to just quit if it was that hard. My family would worry and ask if I needed money. My team needed me to have answers, not doubts.

So I just sat there alone with it…

That’s the thing about being a CEO or a solo founder or the person who’s responsible for everything, it’s the loneliest role there is, and the worst part is, you’re so busy trying to keep everything from falling apart that you convince yourself you don’t have time to deal with it.

Loneliness isn’t just an emotional problem, it’s a business problem, and if you don’t address it, it will kill you before the business does.

1. Here’s the thing you want:

You want to stop feeling like you’re the only one going through this.

You want people who actually understand what it’s like to carry the weight of a business on your shoulders, to make decisions with incomplete information, to feel responsible for other people’s livelihoods, to have everyone looking to you for answers when you’re not sure you have them.

You want someone you can be honest with about how hard this is without them telling you to just get a real job or move on or questioning whether you should even be doing this in the first place, and you want to feel less alone without having to sacrifice the time you don’t have or the focus you need to keep building.

2. Here’s how to do it:

When I was running a founders community and later working at Techstars, people thought we were selling funding or mentorship or connections to investors. Those things mattered, sure, but that’s not really what we were selling, we were selling community.

We were great at curating groups of people and putting them in rooms together, CEO lunches, COO meetups, founder cohorts where people who were going through the same shit could actually talk about it. The number one thing I heard from CEOs wasn’t “I need more capital” or “I need better advisors,” it was “there’s not enough time in the day” and “I don’t know who I can go to.”

That second one is the killer.

When you’re the CEO, you can’t just vent to your team about how scared you are or how uncertain you feel about the next six months, you can’t tell your investors you’re not sure this is going to work, and you can’t even really talk to your family or non-entrepreneur friends because they don’t get it, and their advice is usually some version of “just quit and get a stable job.”

So you end up carrying it all alone, and that isolation compounds over time until you’re burned out, making bad decisions, and questioning why you started.

Entrepreneurial loneliness hits different because it’s not often assuaged by non-entrepreneurs. It’s easy for friends or family who don’t get it to tell you to just quit and find something stable, but entrepreneurs know that’s not really an option. Being an entrepreneur is a lifestyle, and finding people who understand that changes everything.

The first thing that worked for me was joining a founders community, not a networking event where everyone’s pitching each other but an actual community where people showed up consistently, shared honestly, and supported each other without expecting anything in return. At Techstars, the magic wasn’t the mentors or the demo day or the investor intros, it was the cohort. It was putting 10 CEOs in a room together every week where they could talk about the real stuff like the anxiety, the uncertainty, the fear of failing, the pressure of payroll, the loneliness of making decisions nobody else can make.

When you’re around people who are going through it too, you realize you’re not crazy, you’re not weak, you’re not failing, you’re just doing something really hard, and nobody told you it would feel like this.

The thing is, you have to be intentional about this even when you don’t have time, especially when you don’t have time, because loneliness doesn’t care how busy you are, and it will catch up to you whether you deal with it or not.

I used to resist this because I thought I was too busy, I had a company to run and clients to serve and a million things that felt more urgent than grabbing coffee with another founder, but the founders who avoid burnout aren’t the ones who work 80 hour weeks with no breaks, they’re the ones who carve out time, even just an hour a week, to connect with people who get it.

Try CEO lunches, founder coffee chats, or Slack communities where you can ask dumb questions without judgment. It doesn’t have to be a massive time commitment, it just has to be consistent because that one hour a week of connection with people who understand will give you more clarity and energy than another 10 hours of grinding alone.

The thing people forget to mention is you also need people who like you and care about YOU, not just what you’re building or how much you’re raising or what your revenue is. Those people might be other founders who understand the grind, or they might be old friends who remind you that you’re more than your company. Either way you need both. You need people who get this specific type of loneliness and people who pull you out of it entirely.

I had this moment a few years ago where I realized I’d been so focused on building and surviving that I’d let almost all my non-work friendships fade, not because I didn’t care about those people but because I kept telling myself I didn’t have time. Then, I had a week where everything felt like it was falling apart. I looked around and realized I had nobody to call who would just let me be a person instead of a founder, and that scared me more than any business problem I’d faced.

So I started by being intentional about finding something. I started saying yes to dinners with old friends even when I had work to do, I started texting people just to check in without needing anything from them, I started showing up to things that had nothing to do with business, and it didn’t fix the loneliness immediately, but over time, it reminded me that I’m allowed to exist outside of what I’m building.

I used to think I could just power through - focus more, grind harder, get more disciplined, then I’d be fine. That’s what most founders do. They treat loneliness like a weakness they need to overcome, but loneliness isn’t a lack of discipline, it’s a lack of connection, and you can’t optimize your way out of it.

I’ve seen founders who were brilliant, hardworking, and totally capable crumble because they isolated themselves. It wasn’t because they couldn’t do it, they just tried to carry everything alone, and eventually it crushed them. The ones who made it weren’t necessarily smarter or more resilient, they were just better at asking for help and building relationships with people who could actually support them, and that’s not a weakness, that’s survival.

When you stop carrying everything alone and have people who know what it’s like, you don’t have to pretend you have it all figured out. You can be honest about what’s hard and get the support you actually need which gives you perspective when you’re too deep in it to see clearly. Loneliness clouds your thinking. When you’re isolated, every problem feels insurmountable and every decision feels life or death, but connection reminds you that most of what feels catastrophic today won’t matter in a month.

You also start to actually enjoy building again when you’re not drowning in isolation. The problems don’t go away, but they feel lighter when you’re not facing them alone. Finding the people who can support you is the difference between burning out and building something sustainable with your mental health still intact. Founders who crash out don’t usually fail because the business failed, they fail because they couldn’t survive the loneliness. Community is how you stay in the game long enough to actually succeed.

4. Now go:

This week, try this:

Find one founder community, Slack group, or local meetup, and join it. Show up to one event or one call, just one, and see if there are people there who are dealing with the same stuff you are. See if it feels less lonely.

Start here if you only have 10 minutes:

Text one other founder or entrepreneur right now, and ask them, “How are you actually doing with all of this?”

See what happens.

Next Tuesday: The Genius Guide to Not Building a Unicorn

P.S. When I was running founder communities, the thing that always surprised me was how relieved people looked when they realized other people felt the same way they did, like they’d been holding their breath for months and finally got to exhale.

It’s what community does. It reminds you that you’re not alone, and sometimes that’s just enough to keep going.

If this resonates, hit reply and tell me how you’re dealing with loneliness as a founder. I read every response.

Writing from Austin, still building community,

Alex

You’re great at what you do, people want to work with you, you’re making decent money, but you’re also completely maxed out because you’re the one doing all the actual work. Every client deliverable, every project, every output runs through you, and if you stop working, the whole thing stops making money.

So you think, “Okay, I need to scale, I need to sell more, I need to grow this thing,” but the problem is you don’t have time to sell more. You’re too busy doing the work you already sold and can’t stop doing the work because that’s how you make money. You also can’t delegate the work because you’re the only one who knows how it needs to be done.

Welcome to the trap. You’re stuck between being the person who does the work and needing to be the person who sells the work, but you can’t seem to figure out how to be both or transition from one to the other without everything falling apart.

I’ve been there. Most founders I know have been there, and most of us handled it badly the first time because nobody actually teaches you how to make this shift.

So let’s talk about it.

1. Here’s the thing you want:

You want to stop being the bottleneck in your own business.

You want to take on more clients, make more money, grow the thing you’ve built without working 60-hour weeks doing everything yourself. The goal is to sell the work, manage the relationships, bring in new business but have other people actually do the work you’ve sold.

Yet, you can’t get what you want right now because you’re stuck in the trap. Right now, your business only works when you’re doing all the work, and you don’t know how to extract yourself without quality suffering, losing clients, or losing revenue.

2. Here’s how to do it:

I fucked this up the first time I tried it. I was running a consulting business, maxed out on clients, working insane hours, and I thought the solution was just to hire someone to take over delivery so I could focus on sales. Sooooo, I hired someone and handed off a client project. It immediately went sideways.

Not because the person I hired was bad at their job but because I hadn’t actually set them up for success. I’d built zero systems, nothing was documented; therefore, I wasn’t able to train them properly, and I definitely didn’t prepare the client for the transition. I was just like, “Okay, you do it now” and expected it to magically work.

It didn’t. The client was confused, the work wasn’t up to our standards, and I had to step back in and fix everything. I ended up doing more work than if I’d just done it myself in the first place.

Here’s what I learned from that disaster and from watching other people navigate this transition way better than I did:

You can’t transition from doing the work to selling the work overnight.

It’s not a switch you flip. You don’t wake up one day and suddenly become a salesperson; it’s a gradual shift that starts with freeing up time. Most people try to do it too fast, and it blows up in their face.

First, you need to accept that, for a while, you are going to be doing both, and it’s going to suck. But as you start building systems, hiring carefully, and intentionally managing client expectations, you start having more bandwidth to focus on taking calls, responding to inbound leads, following up with prospects, going to events, building relationships, etc…

The selling then happens naturally when you’re not drowning in delivery.

For me, the tipping point was when I realized I had 10 hours a week that weren’t consumed by client work, and I started using that time to reach out to people, take coffee meetings, write content, do the things that bring in new business. That 10 hours turned into 20, then 30, and eventually, I was spending most of my time on business development and very little on delivery.

Document everything you do.

This sounds boring and tedious; you don’t want to do it (nobody does), but if you don’t, no one else can replicate it. Every process, every template, every decision framework, every client interaction… write it down or record it.

I started doing this by just recording myself while I worked, like screen recording client calls or loom videos of me building decks or writing strategies, and then I’d have someone transcribe it and turn it into documentation. It wasn’t perfect, but it was way better than trying to sit down and write a manual from scratch.

Hire for execution first, not strategy.

The mistake I made was hiring someone and expecting them to figure it all out at once. What actually works is hiring someone to execute a very specific, repeatable part of the job while you continue handling strategy and client relationships.

For me, that meant hiring someone to handle slide design and formatting while I still did the content and strategy. Then over time, as they got better and understood my thought process and how I approached various things, I could hand off more. I didn’t start by saying, “Here, take over this entire client.” I started with, “Here, take over this one repeatable task.”

Tell your clients what’s changing and why.

Most people skip this, and it makes for an even rockier transition. Your clients hired you because they trust you, so when you suddenly hand them off to someone else without providing context, they freak out.

What worked for me was framing it as growth, not replacement. I’d tell clients, “We’re bringing on someone to handle [specific task] so I can focus more on [strategic thing that benefits them].” As a result, they didn’t feel like they were losing me or that they were less of a priority; they actually felt like they were getting more of me and higher-quality service.

You have to be okay with things not being done perfectly your way.

This is the hardest part, especially if you’re a perfectionist or if your personal brand is tied to the quality of the product. Someone else is not going to do it exactly how you would’ve done it, and you have to be okay with that as long as it’s good enough.

I had to let go of the details and focus on asking myself, “Does this solve the client’s problem and meet the standard we promised?” Most of the time, the answer was yes, and the client didn’t notice or care about the small differences.

Accept that your identity will shift, and it will be uncomfortable.

Nobody prepares you for this. When you’re the person doing the work, you know you’re valuable because the output is tangible, quantifiable, but when you transition to selling and managing, its less concrete. It might feel like you’re not actually producing anything at all even though you’re doing the most important thing for the business.

I went through a weird period where I felt guilty that I wasn’t “doing the work” anymore, like I was somehow less valuable even though I was bringing in more revenue, and the business was growing. That’s normal. You get over it.

3. Here’s why it works:

When you’re not the only person who can deliver, you’re no longer the bottleneck, and the business can now grow beyond your personal capacity. The needle starts moving again.

Freeing up time allows you to focus on revenue-generating activities. Selling and closing deals is higher leverage than doing the work yourself. Revenue increases. You make more money.

You can take a vacation without your business collapsing. When the company can run without you, you actually have a business instead of a job.

You get better at the things that actually scale. Doing the work makes you good at execution. Selling the work makes you good at client relationships, positioning, pricing, business development… the things that actually grow a company.

4. Now go:

This week, try this:

Pick one repeatable task in your delivery process, and document it. Screen record yourself doing it, write down the steps, create a template, whatever… just get it out of your head and onto paper.

Then ask yourself, “Could someone else do this with these instructions? If not, what’s missing?”

That’s your starting point.

Start here if you only have 10 minutes:

Look at your calendar for the last month. How many hours did you spend doing delivery vs. selling? If it’s 90% delivery and 10% selling, that’s your problem.

P.S. The transition from doing the work to selling the work is awkward, often cumbersome, and uncomfortable, but once you’re on the other side of it, you’ll wonder why you waited so long.

If this resonates, hit reply and tell me where you’re stuck in this transition. I read every response.

Writing from Austin, still learning to let go,

Alex

Before, it would’ve been filled with power, money, success.

Now, it’s filled with family, friends, happiness, and stability.

I don’t think it’s because I’ve given up or stopped being ambitious. I think it’s because I finally let myself admit what I actually want instead of what I thought I should want.

For years I chased the “impressive” stuff because that’s what you’re supposed to do when you’re building something… You’re supposed to want more revenue, more growth, more recognition, more everything. I mean sure, yeah, I did want those things, or at least I thought I did, until I started getting them and realized they didn’t feel the way I expected.

The shift wasn’t dramatic, it was gradual, like finally admitting to your friend group that you find the Lord of the Rings movies boring even if they all disagree with you (I’m so sorry).

So… before you make your list of goals for 2026, before you commit to the next big thing, I want you to ask yourself one question, “Is this actually what I want, or is this what I think I’m supposed to want?”

The difference matters more than you think… now, let’s get into it:

1. Here’s the thing you want:

You want to stop lying to yourself about what you actually want.

Not in a dramatic way, in a quiet, insidious way where you tell yourself you want the promotion, the bigger business, the impressive title, the revenue milestone, the recognition… because that’s what ambitious people are supposed to want, but when you really sit with it, you’re not entirely sure you actually want any of it.

Maybe what you actually want is smaller, quieter, less impressive, like more time or more space or more freedom to do nothing. Maybe you want to work less instead of more, to build something modest that pays the bills without consuming your life, to stop performing ambition and just exist. But that doesn’t sound like something a serious person would say, so you keep chasing the thing you think you should want, and it’s exhausting.

2. Here’s how to do it:

Start asking yourself questions, and answer them…honestly.

A few years ago a mentor told me I should find a CEO for my business, and I got so upset, like genuinely angry about it. I was trapped in this ego validation that said, “Well the CEO is the most important so of course you want to be that.” But when I really thought about it, I realized they were right—I never wanted to be the CEO, I never have been.

I’ve never wanted to fly around the country or fundraise or be the face of things or have to constantly keep up and talk to people or ride the whole business on my shoulders. What I actually wanted was to give my input, my ideas, my skills, and not carry all the weight. I wanted influence and creative control without the title and the performance that comes with it.

That’s a hard thing to admit when you’ve spent years building toward something because it sounds impressive.

But here’s what I started noticing: I wasn’t the only one doing this.

I was talking to a founder a few months ago who’d been grinding on their startup for three years - decent traction, interested investors, all the markers of “success.” I asked them, “Do you actually want to keep doing this?”

Long pause.

Then they said, “I don’t know. I feel like I should want to. Everyone’s telling me I’m onto something. It would be stupid to quit now.”

Notice the language… “should want,” “stupid to quit,” not “I’m excited about this” or “I love this,” just obligation.

I have another friend who spent years working toward a VP role at a big tech company. They finally got it, and within six months they were miserable. Not because they were bad at the job but because the job required a version of themselves they didn’t want to be… endless meetings, office politics, managing up, performing confidence even when they felt uncertain. They thought they wanted the title, but what they actually wanted was respect and influence, and there were other ways to get that without the VP lifestyle.

So here’s what I’ve learned from watching this pattern play out over and over, including in my own life:

Most of us are chasing what a goal represents, not the goal itself. You don’t want the promotion, you want the validation. You don’t want the revenue milestone, you want the security and status. You don’t want the big audience, you want to feel like you matter.

And once you realize that, you can ask, “Is there another way to get what I actually want?

For me, it was realizing I could have influence and creative control without being the CEO. For my friend with the VP role, it was realizing they could have respect and influence through their work and reputation without the title. For the startup founder, it was realizing they could build something meaningful without trying to turn it into a unicorn.

Every goal comes with a lifestyle. The promotion means more meetings, more politics, less autonomy. The big business means managing people, fundraising, constant growth pressure. The impressive title means playing a role, showing up a certain way, living up to expectations.

Most people focus on the end state without thinking about the daily reality of living it.

So I started doing this exercise: I write down what my average Tuesday would look like if I achieved the goal, not the highlight reel but the mundane reality. Do I actually want to live that day? Most of the time, the answer is no.

We live in a culture that worships ambition where more is always better and wanting less is seen as settling. But what if wanting less isn’t settling, what if it’s clarity?

Maybe you don’t want the empire, maybe you want the small, profitable thing that funds your life without it being your whole life. Maybe you don’t want to be famous but rather known by the people who matter and invisible to everyone else. Maybe you don’t want to work 60-hour weeks. Maybe you want a job that pays well and ends at 5pm so you can go live your actual life.

You have to give yourself permission because nobody else will, and you’re allowed to want less than you’re capable of because capability doesn’t equal obligation.

The other thing I’ve learned: you don’t have to blow up your life to figure this out. If you think you want something different, try a small version first.

Think you want to quit your job and freelance? Start freelancing on the side, and see if you actually like it or if you just like the idea of it. Think you want to move to a new city? Spend a month there first. Think you want to scale your business? Talk to people who’ve done it, and ask them what their day-to-day actually looks like.

Most people commit to the big change and then realize six months later that they wanted the idea, not the reality.

Here’s what changed for me: I started paying attention to the language I use when I talk about my goals. “Should” and “supposed to” became red flags. When I catch myself saying “I should want this” or “I’m supposed to do that,” I stop and ask, “Do I actually want this, or do I think I should want this?

If the honest answer is “should,” I ask, “What does this goal represent to me, and is there another way to get that?

Most of the time, there is.

3. Here’s why it works:

You stop wasting energy chasing things you don’t actually want. Once you do that, you can intentionally build toward what you do want instead of grinding for years only to realize you wasted so much time on a goal that wasn’t worth it.

You stop performing for other people. Most of what we think we “should” want is born from culture, social media, or the people around us. When you let that go, you get your life back.

You make better decisions. When you’re clear about what you want, ambivalence disappears, and you’re not constantly second-guessing yourself or optimizing for someone else’s definition of success.

4. Now go:

This week, try this:

Pick one goal you’re currently working toward and ask yourself, “Do I actually want this, or do I think I should want this?

If the honest answer is “should,” ask, “What does this goal represent to me, and is there another way to get that?

Write it down, sit with it, see what comes up.

Start here if you only have 10 minutes:

Think about the last time you achieved something you thought you wanted—did it feel the way you expected or was there a quiet disappointment underneath?

That disappointment is information.

Next Tuesday: The Art of Doing Less

P.S. I spent most of my twenties chasing things I thought I should want—the bigger business, the recognition, the proof that I was serious. Then I got some of it, and it didn’t feel the way I thought it would.

The shift happened when I stopped asking, “What should I want?” and started asking, “What do I actually want?” Turns out, what I actually want is way simpler than what I thought and way more satisfying.

If this resonates, hit reply, and tell me what’s one thing you’re chasing that you’re not sure you actually want. I read every response.

Writing from Austin, wanting what I want,

Alex

You want to be the person who stays in touch.

The friend who checks in. The colleague people remember fondly. The one who doesn’t let relationships die from neglect.

Right now? Keeping in touch feels exhausting… not because you don’t care. You do. You want to be thoughtful. Present. Available.

Buttttt…. you’re also running a business, managing your own chaos, trying not to drown in your inbox. And every time you think “I should text that person,” you feel guilty because you haven’t in three months.

So you don’t text them and now it feels weird and the longer you wait, the weirder it gets.

You’ve probably seen those people who just… seem to know everyone. Who run into friends everywhere. Who have this effortless web of relationships that looks like ✨magic✨.

My co-founder Brian is one of those people.

We can’t go anywhere without him running into someone he knows and who genuinely loves him. I’m not joking when I say I’ve brought him to events where we walk in and he knows the host from something they worked on 10 years ago…He’s the best connector I’ve ever met. It’s not an accident. It’s a skill he’s built over years.

When we launched our business together, his ability to keep in touch with people brought in our first paying clients. Not through sleazy networking, just through genuine, consistent connection.

So one day last year I asked him: how do you do this without burning out?

What he told me changed how I think about relationships entirely.

Below is his system…adapted and in my words, but the philosophy is all his:

2. Here’s how to do it:

Step 1: Accept that you can’t keep in touch with everyone (and stop trying)

Brian’s first rule: you can’t maintain meaningful relationships with 500 people.

Your brain wasn’t built for it. Your schedule doesn’t allow it. And trying to will just burn you out.

There’s this concept in anthropology called “Dunbar’s number”—the cognitive limit to stable social relationships is around 150. But for close relationships? The number drops to 5-15 people.

So stop pretending you can give equal energy to everyone.

Brian’s approach: Make a list. Be ruthless. 30-50 people max.

His list includes:

• Immediate family (partner and parents)

• Close friends he actually wants to stay close to

• Colleagues he’s building with or learning from

• People he’s intentionally investing in (even if he barely knows them… yet)

• Anyone in his personal growth orbit (like his recovery community)

This is the real network. Everyone else? They’re fine. They don’t need weekly check-ins.

Brian reviews his list twice a year. People drift. Priorities shift. That’s okay.

The point isn’t to be cold. It’s to be intentional and know that when you spread yourself too thin, nobody gets the real version of you.

Step 2: Eliminate decision fatigue (pre-decide who you’re reaching out to)

Brian’s insight: the worst time to figure out who to text is when you finally have 10 free minutes.

You’ll freeze. You’ll overthink it. You’ll scroll through your contacts and feel overwhelmed. Then you’ll end up on Instagram instead.

His solution: pre-decide.

He keeps his list in a simple note. Names, birthdays, last contact dates, and a reminder for who he wants to check in with this month.

When he has time, he doesn’t think “who should I text?” He just opens the note and picks someone.

Zero thinking required. Zero decision fatigue.

Research on willpower shows we have finite decision-making energy each day. Every choice—even small ones like “who should I reach out to?”—depletes that reserve.

Pre-deciding removes the friction. You’re not deciding whether to reach out or who to reach out to. You’re just doing it.

Step 3: Stop keeping score (one-way is fine)

This is the part Brian hammered into me: keeping in touch isn’t a transaction.

Texting someone doesn’t hinge on whether they replied last time.

Some messages are gifts. You send them because you thought of the person… Not because you need something back.

“Thought of you today. That random memory made me laugh. Hope you’re good.”

That’s it. No pressure. No expectation. Just care.

The people who matter will respond when they can. The ones who don’t? That’s information too.

Brian told me he used to get in his head about this. If someone didn’t reply, he’d assume they didn’t want to hear from him so he’d stop reaching out.

Now he realizes: most people are just busy. Or they saw the text and forgot to respond. Or they meant to but life got in the way.

It’s not personal. And even if it is… fine. He still sent the message because he wanted to, not because he needed validation.

Step 4: Ask better questions (and actually care about the answer)

Brian’s pet peeve: most “how are you?” texts are autopilot garbage.

You’re not really asking. They’re not really answering. It’s just filler.

His approach: ask questions that give people permission to be real.

Instead of:

• “How’s it going?”

• “What’s new?”

• “What are you up to?”

He asks:

• “What’s one thing that’s going well right now?”

• “What are you actually excited about lately?”

• “What’s been harder than you expected this month?”

These questions invite actual conversation. Not small talk.

And here’s the key he emphasized: ask because you’re genuinely curious. Not because you’re waiting for your turn to talk.

If you’re using someone else’s answer as a prompt to talk about yourself, they’ll feel it. And they won’t open up next time.

Step 5: Make it a ritual, not a routine

Brian’s philosophy: keeping in touch is a mental health practice.

Loneliness kills more dreams than failure and the people you think are “too busy” to hear from you are often hoping someone checks in.

If you wait until you “feel like it,” you never will.

His system: schedule it. Put it on your calendar like a workout or a meeting.

He blocks 20 minutes every week. Sends 3-5 “thinking of you” messages. Sometimes more. Sometimes just one.

It doesn’t need to be deep, it just needs to be consistent.

Research on habit formation shows that behaviors tied to specific times and contexts are more likely to stick. “Sunday mornings = reaching out” becomes automatic. You stop debating whether to do it. You just do it.

Here’s what Brian told me surprised him: the more he did it, the easier it got. Not because he got better at writing texts but because he stopped overthinking them.

3. Here’s why it works:

You stop carrying guilt about who you “should” have texted.

When you have a system, you know you’re already doing what you can. You’re not ignoring people. You’re just being realistic about your capacity.

You actually stay in touch (instead of just feeling bad about not staying in touch).

Consistency beats intensity. Five people you check in with regularly matters more than 50 people you think about texting but never do.

You build real relationships, not shallow networks.

When people know you’ll actually reach out not just when you need something they trust you more. They open up and most of the time, they show up when you need them too.

You stop absorbing other people’s flakiness.

When you stop expecting everyone to reciprocate, you stop feeling hurt when they don’t.

You reach out because you want to. If they respond, great. If not, that’s okay too.

4. Now go:

This week, try this:

Make your list. 30-50 people. Write it down.

Then schedule 20 minutes this weekend to reach out to 3 people on that list. Wish them a happy holiday, tell them you hope their well.

Not because you need something… literally just because you thought of them and see how it feels.

Start here if you only have 10 minutes:

Text one person right now. Someone you’ve been meaning to reach out to but haven’t. Don’t overthink it. Just say: “Hey, thinking about you. Hope you’re doing well.”

Hit send.

This weeks prompt: What’s been the best part of your week?

P.S. I’ve been using Brian’s system for a few months now. Some people reply immediately. Some don’t reply at all. Some send me voice memos about random shit happening in their lives.

All three of those outcomes are fine because I’m not texting them for a response. I’m texting them because I care.

If this resonated, hit reply and tell me who you’re going to reach out to this week. I read every response.

Writing from Austin, staying connected,

Alex

1. Here’s the thing you want: You want to stop letting trivial things ruin your day

The spilled coffee. The cancelled flight. The person who didn’t text back. The thing that broke. The plan that fell through.

You want to be the person who just… moves on. Who doesn’t spiral. Who doesn’t carry every minor frustration like it’s a personal attack.

You’ve probably seen that post that goes: “One of the most freeing realizations in life is that you can just… not care about certain things.”

And you think: yeah, okay. But how?

Because right now, you do care. You care when someone’s rude to you. You care when things don’t go as planned. You care when something that shouldn’t be a big deal… feels like a big deal.

You want detachment. Not the cold, apathetic kind. The kind where you still care about what matters, but you stop giving energy to the stuff that doesn’t.

2. Here’s how to do it:

Step 1: Understand what detachment actually is and isn’t

A couple weeks ago, I walked out to my car and someone had keyed it.

Long, deliberate scratch down the side. The kind that costs money to fix.

My first thought was: Who does this?

My second thought was: I could be really angry about this. Or I could just… not.

Whoever keyed my car is probably miserable. And what they want—whether they know it or not—is for me to be miserable too.

So I just… didn’t let it bother me.

Took a photo for insurance, got in the car, drove away.

A few years ago, that would’ve wrecked my week. I would’ve spiraled. Told everyone. Replayed it in my head. Let it sit in my chest like a weight.

Now? It’s just a scratch. On a car. That I can fix or not fix. Either way, it doesn’t matter.

That’s detachment.

Not apathy. Not pretending nothing matters. Just recognizing that most things aren’t worth the energy we give them.

Here’s what I’ve realized: we have a finite amount of attention and emotional capacity. Decision fatigue is real—neuroscience backs this up. Every time you care about something insignificant, you’re spending resources you don’t get back.

Spilled coffee? That’s energy.

Delayed flight? That’s energy.

Someone didn’t text back? That’s energy.

And most of the time, that energy goes to things that won’t matter tomorrow. Let alone in a year.

The filter I use: If it won’t matter in a year, don’t let it ruin your day.

Step 2: Ask yourself if this will matter in a year (and practice letting go in real time)

When something goes wrong, pause.

Not to suppress what you’re feeling or pretend you’re fine. Just to check in: Will this matter in a year?

There’s this concept in psychology called “affect labeling”—naming what you’re feeling reduces its intensity. When you ask “will this matter in a year?” you’re essentially labeling the situation as temporary. Your brain registers it as less threatening. The emotional charge drops.

But here’s the thing: you don’t just ask the question once and move on. You practice it constantly.

Every time you choose not to spiral over something insignificant, you’re building the muscle.

When you narrate what you’re feeling—even just to yourself—you activate the prefrontal cortex, the part of your brain responsible for executive function and emotional regulation. It literally helps you process and release the emotion faster.

So yeah. I started narrating my frustrations like I’m explaining them to someone else. Sounds kinda silly. But it works.

Step 3: Recognize what you can and can’t control

Most of what stresses us out is stuff we can’t control anyway.

Someone keyed my car. I can’t unkey it. I can’t find out who did it. I can’t make them apologize.

What I can control: whether I let it wreck my day or not.

I started splitting things into two piles: stuff I can control (my reaction, my next move, how I frame it) and stuff I can’t (what already happened, what other people do, external circumstances).

Then I just… stopped thinking about the second pile.

The burnt toast theory:

There’s this idea that’s been floating around—people call it the “burnt toast theory.”

The concept is: when something trivial goes wrong (burnt toast, missed bus, spilled coffee), it might be protecting you from something worse. You miss your train, which makes you late, which means you’re not in the car accident that happened five minutes earlier on your usual route.

Idk if that’s true. Probably not. But I like the reframe.

What if the thing that went wrong… just went wrong? And it’s fine?

Step 4: Stop treating everything like an emergency

Not everything is urgent. Most things aren’t.

But we’ve been conditioned to react to everything immediately. Every notification. Every inconvenience. Every minor frustration.

That’s exhausting.

There’s research showing that humans have an “urgency bias”—we prioritize tasks that feel urgent over tasks that are actually important. It’s why we respond to emails immediately but put off the big project.

Detachment helps you override that bias. You stop reacting to everything like it’s a crisis and start responding to what actually matters.

So now I ask: Is this actually urgent? Or does it just feel that way?

Most of the time, I have more time than I think.

Step 5: Let other people’s chaos be theirs, not yours

Someone else’s bad day doesn’t have to become your bad day.

Someone’s rude to you? That’s about them, not you.

Someone cancels last minute? Annoying, but it’s their mess, not yours.

You don’t have to absorb other people’s energy.

I have a friend who’s chronically late. Like, always. We’ll make plans, and I know they’re going to show up 30-45 minutes late.

It used to bother me. I’d get annoyed, feel disrespected, let it mess with my mood.

Now? I just assume they’ll be late and plan accordingly. Bring a book. Answer emails. Enjoy the extra time.

When they show up, I’m not mad. Because I didn’t let their lateness become my problem.

When someone else is spiraling, stressed, or chaotic, I remind myself: This is theirs to carry, not mine.

You can be supportive. You can be present. But you don’t have to take on their emotional state.

3. Here’s why it works:

You stop spending energy on things that don’t deserve it.

We have a finite amount of attention and emotional capacity. When you stop caring about the trivial stuff, you have more left over for what actually matters—your relationships, your work, your goals, your peace.

Research from Stanford shows that people who practice “selective attention”—consciously choosing what to focus on—report lower stress levels and higher life satisfaction. It’s not about ignoring everything. It’s about curating what gets your energy.

You train your brain to categorize appropriately.

Not everything deserves the same emotional weight. A scratched car is not the same as a betrayal. A cancelled flight is not the same as a loss.

When you ask “will this matter in a year?” you’re giving your brain permission to categorize things correctly. Neuroscientists call this “cognitive reappraisal”—changing how you think about a situation to change how you feel about it. Studies show it’s one of the most effective emotion regulation strategies.

You take back control.

You can’t control what happens to you. But you can control how much space it takes up in your head.

There’s research on something called “psychological flexibility”—the ability to stay in contact with the present moment and act according to your values, even when you’re experiencing difficult thoughts or emotions. People with higher psychological flexibility have better mental health outcomes, stronger relationships, and higher resilience.

That’s the shift—from reacting to everything to responding to what matters.

You stop absorbing other people’s chaos.

When you stop taking on everyone else’s stress, frustration, and bad moods, you get to keep your energy.

Mirror neurons in our brains make us naturally empathetic—we feel what others feel. That’s beautiful for connection. But it also means we can absorb stress that isn’t ours. Detachment isn’t about shutting off empathy. It’s about having boundaries around what you carry.

You can still be supportive without being consumed.

So yeah. Detachment isn’t about not caring. It’s about knowing what’s worth carrying. And most things? They’re not.

4. Now go:

This week, try this:

Next time something frustrating happens… spilled drink, cancelled plan, inconvenience… pause before you react.

Ask yourself: Will this matter in a year?

If the answer is no, say out loud: “This is annoying. But I’m letting it go.”

Then move on. See how it feels.

Start here if you only have 10 minutes:

Think about the last thing that stressed you out. Ask yourself: does this still matter today? If not, that’s proof you didn’t need to carry it as long as you did.

Next Friday: The Ordinary Story of The Guy Who Learned to Let Go

P.S. My car is still scratched. I still haven’t fixed it. And honestly? I kinda don’t care. It’s just a car. And whoever keyed it is still miserable. I’m not.

If this resonated, hit reply and tell me what you’re working on letting go of. I read every response.

Writing from Austin, unbothered,

Alex

That trip changed how I understood charm. But understanding something and actually doing it are different.

Today I want to tell you about the first time I really used what I learned—and how one conversation with a stranger at a conference changed my entire business.

1. Here’s the thing I wanted:

I wanted to stop feeling small in rooms.

For most of my life, I’d sit at dinners and barely say a few words. Not because I had nothing to say, but because I didn’t feel good enough… Interesting enough… Like I belonged there.

I didn’t know what to talk to people about. Conversations felt awkward. I felt awkward.

Then I watched Jeff in Chicago and something shifted: charm isn’t about being the most interesting person in the room. It’s about being the most interested.

But I didn’t really understand what that meant until I met Mark…

2. Here’s how I did it:

The Setup: ECRM Conference, some hotel in Jacksonville, Florida

I was 25 years old, standing alone at a buyers conference in Florida.

I’d spent my savings… every dollar I had… to manufacture 5,000 units of a nail polish holder called Polish Pal. I made the sell sheet. I bought the display. I designed the poster. I flew across the country by myself.

I was terrified.

I came from a family of real estate entrepreneurs, but none of them knew anything about beauty or nail polish or selling a product. I was completely out of my depth.

ECRM is a conference where they match make you to meet with buyers from retail stores—Nordstrom, TJMaxx, all the ones we know—in hopes they’ll buy your product for their shelves.

The oh-shit moment was realizing that while I didn’t know anyone and was the youngest person there… everyone else seemed to already know each other.

Meet: “The Guy Next to Me”

The stand next to mine was run by this grey-haired, kinda unkept guy in his early-70s selling a really cute nail polish product with flowers in it called Blossom Beauty.

Over the first few days, I noticed something: every buyer already knew him really well. They’d greet him warmly. They barely talked business. It was like they were catching up with an old friend.

Meanwhile, I was nervously pitching my product to strangers who didn’t know me from anyone.

So one day, I walked over to meet him.

The Big Moment

I looked at his product… this delicate, feminine flower design…

and then looked at him. Sharp contrast.

A grey-haired guy in his 70s with a really cute flower product?

I saw his name tag: “Mark Friedman”

I grabbed mine and held it up next to his.

“Mark Friedman… Alex Friedman… are we secretly related?”

He laughed. “Lithuanian Jew?”

“No, Ukrainian Jew.”

“Ah, guess not! But I’m Mark.”

I introduced myself, and eventually pointed at his product, then back at him. “So… how did THIS happen?”

He laughed. And then he started talking.

Mark told me his parents owned the number one nail polish manufacturer in North America. All the products in Vietnamese nail salons? Those came from them.

He’d sold the business two years earlier. Retired. Then his brother-in-law came to him with this flower nail polish idea. Mark was bored, so he said yes.

I kept asking: “So why are you here if everyone already knows you?”

“It’s easier to see everyone in one shot than to fly around the country.”

Then I asked about the sale, about retirement, about what it was like working with family. Every answer led to another question.

That opened the door.

The Next Few Days

Over the course of the week, Mark and I became friends.

He’d coach me on things. Tell me stories about the industry. Ask me for advice on how to talk to his kids, who were my age.

I’d ask him about his life. His parents. How the business worked. What buyers actually cared about.

We’d talk about life.

By the end of the week, I asked him to mentor me.

He said: “Alex, I’m too old and tired to mentor you. But I’m going to introduce you to Shawna, my head of sales. She’ll mentor you as a favor to me.”

And she did.

Shawna helped me get vendor agreements with Forever 21 and Urban Outfitters. She coached me on branding. She introduced me to buyers and told me exactly what to do.

That purely chance meeting… being put next to each other at a conference… changed my entire career trajectory.

3. Here’s what it cost me:

Ego

You can’t center yourself if you want to be charming. You have to let other people shine.

At that conference, I could have spent every conversation talking about my product, my vision, my story. But I didn’t…

I wanted to learn. I asked Mark about his life, I listened more than I talked, and I made it about him. Then, I only pitched when appropriate.

I had to be willing to not be the expert. To admit I didn’t know things. To ask for help.

That’s uncomfortable when you’re 25 and trying to prove yourself.

But it’s also what made Mark want to help me.

That takes ego out of the equation.

Attention

You have to actually be engaged. Listen. Nod. Smile. Be authentically present.

You can’t fake this. If you’re asking questions just to check a box, people feel it.

With Mark, I was genuinely fascinated. A 70-year-old guy with a flower nail polish brand? How did that happen? I had to know.

4. Here’s why it worked:

I genuinely believed Mark was interesting

After watching Jeff, my mindset shifted: every person I meet could be the most interesting person I’ve ever met. It’s my job to find out what makes them that.

With Mark, I didn’t have to fake it. A grey-haired guy with a flower product? I HAD to know how that happened. That curiosity was real. And that’s what opened the door.

You can’t be performative if you truly believe anyone can be fascinating.

I adapted to meet him where he was

Mark was in his 70s. I was in my 20s. We had nothing in common on paper.

So I didn’t try to pretend I was older or more experienced. I just met him where he was. Asked about what he cared about. Matched his energy.

Jeff’s lesson from Chicago in action: be a chameleon without losing yourself.

I gave him something he wanted… to feel heard

All any of us want is to feel like our stories matter.

Mark had built an empire. Sold it. And now he was kind of just… there. When I asked about his life with genuine curiosity he lit up. He had stories to tell, and I wanted to hear them.

That’s the real key: when you make someone feel seen and important, they want to help you. Not because you asked, but because you made them feel good.

You never know who you’re sitting next to

I could have ignored Mark. I could have focused only on pitching buyers or networking with people who looked more “important.”

But I didn’t… I just talked to the guy next to me

And that one conversation changed my business.

Mark taught me what Jeff had shown me but I hadn’t fully internalized: relationships are everything and you never know who you’re sitting next to.

5. Now go:

This week, try this:

Find someone you wouldn’t normally talk to … different age, different background, different industry… and make them feel like the most interesting person in the room for five minutes.

Ask them about their life. Go deeper. Actually listen.

You never know who you’re sitting next to.

Bonus: What I Learned From Mark That Jeff Didn’t Teach Me

Jeff showed me that charm is adaptability.

Mark showed me that charm is generosity.

When you make someone feel seen, important, and interesting—they want to help you. Not because you asked, but because you made them feel good.

That’s the real power of charm. It’s not manipulation. It’s connection.

Next Tuesday: The Genius Guide to Determining How Much Effort to Put Into Friendships

P.S. Mark passed away a few years ago. I think about him often… not just because of what he did for my business, but because he taught me that one conversation with a stranger can change everything.

If this resonated, hit reply and tell me about an unlikely friendship that changed your life. I read every response.

Writing from Austin, still grateful for Mark and that chance meeting in Florida,

Alex

You know that person at every party who everyone wants to talk to?

The one who somehow makes every conversation feel easy. Who remembers your name after meeting you once. Who leaves and suddenly the room feels a little less interesting.

You’ve probably thought: “I wish I could do that. But I’m just not that type of person.”

I used to think the same thing.

Then I spent one day shadowing my dad’s business partner through back-to-back meetings in Chicago, and I realized something: charm isn’t a personality trait you’re born with.

It’s a skill. And like any skill, you can learn it… here’s how I did:

P.S. If this resonates, hit reply and tell me about the most charming person you’ve ever met. I read every response.

1. Here’s the thing you want:

You want to be magnetic.

Not loud. Not fake. Not performing.

You want to be the person people gravitate toward. The one who can talk to anyone about anything. The one who knows when to speak and when to listen. The one who leaves a room with ten people remembering your name.

Most people think charm is extroverted, over-the-top, performative. Like a used car salesman who’s “on” all the time. The kind of person who leaves you feeling gross afterward.

That’s not charm. That’s performance.

Real charm feels effortless. Like an old friend you just met.

It comes from two things: authenticity and adaptability.

Genuinely caring about the person in front of you while adapting to meet them where they are, not where you are.

2. Here’s how to do it:

Step 1: Understand what charm actually is

I learned what real charm looks like when I shadowed my dad’s business partner, Jeff, on a trip to Chicago in 2017.

Jeff is the former CEO of Auction.com. When you meet him, you immediately understand why. He’s magnetic. Walk into any room and ten people are surrounding him within minutes.

Our first meeting that day was at a young hedge fund. The room was full of 35-year-old guys in finance.

Jeff walked in and immediately started talking about hockey. Season tickets. The game last weekend. Matching their energy… excited, competitive, engaged.

By the end, deal closed 🤝 relationship built.

Next meeting: Sears. The room was full of 70-80-year-old employees.

Jeff completely transformed. Lower energy. Warmer. He talked about his kids the whole time. Asked about their families. Listened more than he spoke.

Same outcome.

That’s when I understood: charm isn’t about being loud or extroverted. It’s about being a chameleon, adapting to the room without losing yourself.

“The most charming people don’t talk at their level. They talk at yours.”

Step 2: Read the room in 30 seconds

When you walk into a conversation, you’re looking for clues.

Start with the basics: demographics and age. What someone younger cares about is probably different from what someone older cares about.

Then, match their energy. Jeff was animated with the hedge fund guys, softer with the Sears employees. Don’t bring party energy to someone who’s clearly reflective.

Finally, listen for what they talk about first. People tell you what matters to them within minutes.

Kids? That’s the thread.

A project? That’s the thread.

A recent trip? That’s the thread.

“Your job is to pull the thread—not redirect the conversation back to yourself.”

Step 3: Make every person feel like the center of the universe (for five minutes)

This is the whole game.

A couple months ago I was on a trip with my dad and I sat next to someone at dinner who mentioned they brew kombucha. Most people would say “oh cool” and move on.

I asked: “What made you start?”

They told me about gut health and fermentation. So I went deeper: “What’s the hardest part?”

Then: “What’s your favorite batch you’ve made?”

By the end of dinner, they were teaching me about SCOBY hotels and flavor experimentation.

I learned something fascinating. They felt heard.

The mechanics are simple:

When someone tells you something, go deeper:

• “What made you decide to do that?”

• “How did that feel?”

• “What happened next?”

Not performative listening where you’re waiting for your turn to talk. Real listening.

“People like people who like them. When you’re genuinely interested in someone, they feel it.”

Step 4: Remember the small things

Jeff remembers everything. Your name. Your kids’ names. The last thing you talked about.

Not because he has a photographic memory but because he cares enough to pay attention.

When you see someone again:

• “How’s your daughter doing with soccer?”

• “Did that project go well?”

• “How was that trip?”

This isn’t a trick. It’s just showing people they mattered.

“Charm isn’t just in the moment. It’s remembering what mattered after the conversation ends.”

Step 5: Adapt without being fake

Here’s the difference:

Fake charm: Pretending to care about something you don’t care about to impress someone.

Real charm: Finding what the other person cares about and genuinely exploring it even if it’s not your thing.

I don’t brew kombucha. I probably never will. But I was genuinely curious about why someone finds it fascinating.

You don’t have to love hockey to ask someone why they love it.

You don’t have to be a parent to care about someone’s kids.

You don’t have to share someone’s interests to be curious about them.

The shift: Believe that every person you meet could be the most interesting person you’ve ever met. Make it your job to find out what makes them that.

And here’s what I’ve learned from watching Jeff and practicing this myself: when you approach people this way, you actually DO find them interesting. It’s not a trick… it’s a shift in how you see people.

“Charm isn’t about being interesting. It’s about being interested.”

Step 6: Know what kills charm

Being over-the-top or performative.

If you’re “on” all the time, people can tell. It’s exhausting.

Centering yourself.

If you’re constantly redirecting conversations to your stories, you’re not charming—you’re self-absorbed.

Asking questions and then not listening.

If you zone out halfway through someone’s answer, they feel it. That’s worse than not asking at all.

Only caring about people who can give you something.

If you’re only charming to people who can help your career or status, you’re not charming. You’re transactional. People smell that immediately.

“Don’t mistake charm for charisma. Charisma is magnetic energy. Charm is making people feel good when they’re with you.”

You don’t need to be charismatic to be charming. Introverts are often the most charming people in the room… they just do it through deep listening and thoughtful questions instead of high energy.

3. Here’s why it works:

People don’t remember what you said. They remember how you made them feel.

When you make someone feel seen, heard, and important, they associate that feeling with you.

Adaptability signals emotional intelligence.

When you can read a room and adjust to match the people you’re with, it shows you’re self-aware, thoughtful, and emotionally mature. People trust that.

Authenticity cuts through the noise.

Most people are performing. When you’re genuinely yourself AND genuinely interested in others, you stand out.

4. Here’s what to avoid:

Don’t confuse charm with being a people-pleaser.

Charm isn’t agreeing with everyone. It’s making people feel good while still being yourself.

Don’t think you need to be extroverted.

Some of the most charming people I know are introverts. They’re just great at asking questions.

Don’t fake interest.

People can tell. If you’re asking questions just to check a box, it’s worse than not asking.

Don’t perform energy you don’t have.

If you’re naturally lower energy, that’s fine. Calm, thoughtful charm is just as magnetic as high-energy charm.

5. You’ll know it’s working when:

• People remember you after meeting you once

• Conversations feel easy, not forced

• People open up to you quickly

• You can connect with anyone—regardless of age, background, or energy level

• People ask about you when you’re not around

• You leave interactions and people feel better for having talked to you

• You’re not exhausted after socializing—because you’re not performing

6. Now go:

This week, try this:

Pick one conversation and make it your goal to make that person feel like the center of the universe for five minutes.

Ask them about something they care about. Go deeper with follow-up questions. Actually listen.

See how it feels. See how they respond.

Start here if you only have 10 minutes:

Next time you talk to someone, instead of thinking “What should I say?” think “What can I learn about them?”

Then ask one good question and actually listen to the answer.

Next Friday: The Ordinary Story of Someone Who Went From Awkward to Magnetic

P.S. My dad and I travel a lot on this boat called The World. He laughs because whenever I leave, everyone asks him where I am. I’m more popular than him on his own trip.

That’s not because I’m louder or more interesting, it’s because I genuinely believe every person could be the most fascinating person I’ve ever met. And I make it my job to find out what makes them that.

Writing from Austin, thinking about Sears (RIP Sears you could’ve been Amazon),

Alex

Not because I actually hated it, but because every time a post of mine did well, my comments and DMs were filled with hate. Sometimes passive-aggressive, sometimes just directly rude.

People saying I looked like I had tons of plastic surgery. Anti-semitic or sexist comments. Saying I talked weird. Calling me dumb.

It didn’t even matter how wholesome the video or post was. There would always be something.

So one day I texted my friend Kevin Espiritu.

Kevin is the CEO and big brain behind Epic Gardening—a gardening empire with 9M+ followers across platforms and millions of dollars in revenue teaching people how to garden.

Kevin is unique because beyond being a master of content and an incredible business builder, he’s extremely insightful and grounded in how he approaches life. He cares about doing things that make him happy so over the years he has become kind of my go-to guy on these type of things.

He said something to me that stuck:

“Alex, you can only get upset about the things that you believe are true. And if you believe they are true and they STILL upset you... well that’s just a signal to look inwards.”

From that moment forward, hate comments don’t bother me. It’s like something reconfigured in my brain. Whenever anyone leaves a comment or I even get real-life feedback, I run it through the filter: “Do I believe this is true?”

Here’s how Kevin developed that mindset (and how you can too).

1. Here’s the thing he wanted:

Kevin wanted to teach people about gardening; show people how to grow tomatoes, build raised beds, start a garden from scratch. Make free content that actually helped people. That’s it.

You’d think teaching people about plants would be safe. Wholesome. Uncontroversial.

But when you have an audience, the hate always comes somehow.

People calling him fat. Saying his head’s too big. Telling him he doesn’t know what he’s talking about. Accusing him of just being there to sell stuff.

Kevin didn’t want to spend his life spiraling over comments from strangers on the internet. But more importantly, he didn’t want the hate to stop him from doing what he loved: teaching people how to grow things.

He wanted to build something meaningful and keep building it, regardless of what random people on the internet thought about him.

The key to not caring what people say isn’t about developing thick skin. It’s about believing in your long term mission more than believing what some asshole is saying on the internet.

2. Here’s how he did it:

The Framework: Is This True?

Over time, Kevin developed a simple filter—the same three-question framework I shared with you on Tuesday:

If a comment bothers you, ask yourself: Is this true?

If it’s not true, it’s easy to dismiss. Someone says you don’t know what you’re talking about when you’ve spent years studying something? Okay, move on.

If it IS true, then it’s not really about the comment, it’s about how you feel about that truth.

“The ones that bothered me were the ones that were true,” Kevin told me.

Someone commented that he was getting fat once. And instead of dismissing it, he thought: Fuck. I am actually kind of getting fat right now.

That comment stung because it hit something he already believed about himself.

So instead of spiraling or getting defensive, he’d respond with a disarming comment:

“Yeah, I am. Working on it though.”

And that was it. No drama. No spiral. Just acknowledgment and moving on.

This is how Kevin uses the framework in practice. Not as a theory, but as an actual filter every time a comment comes in.

The Three Moves He Uses Now:

When Kevin gets a hate comment now, he does one of three things:

1. He just moves on.

Most of the time, he reads it, thinks “okay,” and keeps scrolling. It doesn’t even register.

2. He uses the disarming comment technique.

Someone says something critical, he agrees with the part that’s true and adds context.

“You’re just here to sell stuff.”

Kevin’s response: “I make thousands of pieces of free content so you don’t have to buy anything. So it’s fine if I sell stuff.”

No defensiveness. Just facts. It takes the wind out of the criticism immediately.

3. He trolls back (if he feels like it).

Sometimes, if the comment is absurd enough and he’s in the mood, he’ll have fun with it.

Not in a mean way. Just in a “this is ridiculous and I’m not going to pretend it’s serious” way.

What Changed Over Time

Years ago, comments like “You’re just here to sell stuff” would have bothered Kevin.

Now? He laughs.

Because he knows the truth: He’s created thousands of hours of free content. He’s helped millions of people start gardens. If someone thinks he’s just there to sell, they’re not paying attention, and that’s not his problem.

The shift wasn’t about becoming numb. It was about becoming clear.

Clear on what’s true. Clear on what he cares about. Clear on what’s worth carrying.

3. Here’s what it cost him:

Nothing, really. Because he never let it cost him anything.

Kevin didn’t have to develop thick skin. He didn’t force himself to stop caring. He didn’t sacrifice his emotional capacity.

He just cared more about the work than the noise.

But here’s what his approach DOES require:

Loving what you do more than you hate the criticism

Kevin genuinely loves teaching people about gardening. He loves making content. He loves helping people grow their first tomato.

That love is bigger than the frustration of someone being an asshole in the comments.

You’re going to get hate regardless.

The question is: Do you enjoy what you’re doing enough to keep going anyway?

If the answer is no, the hate will eat you alive.

If the answer is yes, the hate becomes background noise.

Caring more about the long-term goal than short-term frustration

Kevin’s not building for the person leaving a mean comment today. He’s building Epic Gardening for the long haul.

He’s thinking: How many people can I help? How much content can I create? What does this look like in 5 years?

When you’re focused on the long game, the short-term assholes don’t matter as much.

The discipline to filter signal from noise

Kevin doesn’t ignore all feedback. He listens to the useful stuff.

But he’s developed the ability to quickly sort: Is this helpful feedback I should consider? Or is this just someone being a dick?

Most people can’t tell the difference. Kevin can.

Wanting to put stuff out more than you care about the hate

This is the key. Kevin’s drive to create and share is stronger than his concern about criticism.

If you care more about what people think than you care about the work itself, you’ll never make it. The hate will win.

If you care more about the work, the hate becomes irrelevant.

4. Here’s why it worked:

He cared more about helping people than about being liked

Kevin’s mission is clear: teach people how to garden. Help them grow food. Make gardening accessible.

That mission is bigger than any individual comment. When you care deeply about what you’re building, individual opinions matter less.

He never tried to build thick skin, he just focused on the work

Kevin didn’t set out to “not care” about hate comments. He just cared MORE about creating good content.

It’s not about building armor. It’s about building something you love so much that the armor isn’t necessary.

People will always have opinions, he doesn’t ignore them, he filters them

Kevin doesn’t dismiss all feedback. He’s not walking around saying “fuck everyone’s opinion.”

He listens, but he’s clear on the difference between:

• Useful feedback that helps him improve

• Random noise from people projecting their stuff

Most people treat all feedback the same. Kevin knows better.

You’ll get hate regardless, might as well enjoy what you’re doing

This is the key insight: The hate is coming whether you care about it or not.

If you build something visible, people will criticize it. That’s just the reality.

So your only real choice is: Do you love what you’re doing enough to keep going anyway?

If yes, you’ll be fine. If no, you’ll quit.

Kevin loves teaching about gardening more than he hates the occasional asshole comment. So he keeps going.

He’s playing the long game

Kevin’s not optimized for avoiding criticism today. He’s optimized for building Epic Gardening for the next decade.

When you’re focused on the long-term goal, the short-term frustrations become irrelevant.

Someone says something mean? Okay. He’s still going to help millions of people start gardens. That matters more.

5. Here’s what he avoided:

He didn’t confuse “not taking it personally” with not caring

This is the trap I talked about on Tuesday: people think “not taking it personally” means becoming cold or detached.

Kevin didn’t do that. He still cares about his work. He still cares about helping people. He just doesn’t let random strangers’ opinions dictate his self-worth.

He didn’t ignore all feedback

He identifies what’s real vs. what’s not and adjusts accordingly.

There’s a difference between useful feedback and random hate. He can tell the difference.

This goes back to the framework: Is this true? Does it come from someone whose perspective I value? Is it worth addressing?

He didn’t use it as an excuse to avoid accountability

If multiple people are saying the same thing, Kevin doesn’t just dismiss it as “not taking it personally.”

He looks at it: Is there a pattern here? Is this something I should address?

“Not taking it personally” doesn’t mean ignoring valid criticism. It means not carrying the emotional weight that isn’t yours.

He didn’t become defensive

Most people’s instinct when criticized is to defend, explain, justify.

Kevin just doesn’t. He either agrees with the true part, or he moves on.

No essays. No explanations. No trying to convince strangers he’s a good person.

He didn’t stop being himself

Some creators change who they are to avoid criticism. They soften their edges, play it safe, try to be palatable to everyone.

Kevin didn’t do that. He kept teaching gardening the way he wanted to teach it. If some people didn’t like it, that was fine.

He didn’t spiral or ruminate

The biggest trap with hate comments is the spiral. You read one, then you can’t stop thinking about it. You replay it. You imagine responses. You wonder what that person thinks of you.

Kevin skips all that. He reads it, processes it (or doesn’t), and moves on.

His advice if you’re drowning in hate comments?

“If you’re drowning in it, there’s probably a reason. You’ve got to look at yourself.”

Not in a “you deserve it” way. In a “what are you believing about yourself that’s making these land?” way.

6. Now go:

This week, try Kevin’s approach:

Next time you get a comment, criticism, or feedback that stings, ask yourself:

Is this true?

If it’s not, move on. Don’t think about it again.

If it IS true, ask: Does this bother me because I’m insecure about it? Is it something I want to change?

Then decide: Am I going to work on this, accept it, or let it go?

Bonus: Kevin’s Three Moves You Can Steal

1. Just move on. Most comments don’t deserve your energy. Read it, think “okay,” keep going.

2. Disarming comment technique. Agree with the part that’s true, add context, take away the fight. Example: “Yeah, I do sell stuff. I also make thousands of hours of free content. Both can be true.”

3. Troll back (if you feel like it). If the comment is absurd and you’re in the mood, have fun with it. Don’t take it more seriously than it deserves.

Next Tuesday: The Genius Guide to Becoming More Charming

P.S. If you want to learn how to grow literally anything, check out more of Kevins products at epicgardening.com.

If this resonated, hit reply and tell me how you handle criticism. I read every response.

Writing from Austin, thinking about how absurd it is that people leave hate comments on gardening videos,

Alex

Hey y’all,

Last week’s playbook talked about asking better questions which got me thinking, “well, what if I don’t like the answers” lol and that lead me to this week’s playbook on how to not take things personally. This was definitely a learned skill for me and it’s served me so well over the years!!

Playbook is below👇

Case study coming on Friday

Writing from Austin,

Alex

P.S. If this resonates, hit reply or leave a comment and tell me what you’re working on letting go of. I read every response and love hearing from everyone!

1. Here’s the thing you want:

You want to stop spiraling every time someone says something that stings.

A hate comment. A critical text. Feedback that feels like an attack. A friend who doesn’t reply. Someone canceling plans. Your partner asking you to change something small.

You want to be able to move through the world without constantly wondering if people are mad at you, disappointed in you, or judging you.

You want the freedom to post something online without refreshing for validation or bracing for criticism.

You want to hear feedback without your chest tightening and your brain immediately going to “I’m the worst.”

Most people think “not taking things personally” means becoming emotionally numb. Detached. Unbothered in a cold, robotic way.

It’s not that. It’s the opposite.

Not taking things personally means having enough empathy and self-awareness to know what’s about you and what’s about them... and letting go of the stuff that isn’t yours to carry.

2. Here’s how to do it:

Step 1: Understand where this actually comes from

I make content online. When something gets traction, the hate comments come. They always come.

For a while, I’d spiral. Screenshot them. Send them to friends. Start typing responses. Delete them. Type again. My brain would loop on it for hours.

One day I told my friend Kevin Espiritu, “You’re so lucky. You don’t get hate comments because your content is so wholesome.” (Kevin runs a big gardening channel.)

He laughed. “What are you talking about? I get hate comments all the time.”

I was confused. “About what? You teach people about plants.”

“I get called ugly, stupid, that my head’s too big, that I don’t know what I’m talking about...”

I asked how he didn’t let them get to him.

He said: “You can only get upset about the things you believe are true. If someone says something that upsets you, that’s a signal to look inward, not outward.”

That shifted everything for me.

The comments that bothered me weren’t random. They were hitting something I was already insecure about. The ones that didn’t land? I didn’t even remember them.

Step 2: Run it through the filter

Now when I get a comment (or feedback, or criticism, or someone acting weird), I ask myself three questions:

Question 1: Is this true?

If it’s not true, I move on. I don’t think about it again.

Someone says “You don’t know what you’re talking about” and I know I’ve done the work? Cool. Not my problem.

Question 2: Does this upset me?

If it’s true but it doesn’t upset me, I also move on.

Someone says “You post a lot about yourself” and yeah, I do, and I’m fine with that? Not a problem.

Question 3: If it upsets me, why?

This is where it gets interesting.

If something is true AND it upsets me, that’s a signal.

Is it something fixable? Is it worth fixing? Do I want to fix it?

If yes, I move toward fixing it.

If no, I accept it and let it go.

Step 3: Separate hate from feedback

There’s a difference between hate and actual feedback... but not as much as you’d think.

Both are coming from the other person’s worldview, experiences, and projections.

The difference is whether it’s coming from someone whose perspective you value.

Examples:

• Random internet person says you’re cringe → probably not worth considering

• Your partner says they wish you planned more dates → worth listening to

• Your boss yells at you because they had a bad day → not about you

• A mentor gives you critical feedback on your work → probably worth considering

The framework is the same though:

Is this true? Does this upset me? Why? Is it worth addressing?

Step 4: Look at the whole person and situation

It’s a lot easier to not take things personally when you zoom out and look at someone’s full context.

Example 1: The MIA friend

Two years ago, my best friend died. I went kind of MIA after that. Stopped seeing people. Stopped replying to texts. I only hungout with people who knew her and knew the situation because it was easier than having to explain my grief over and over. It was easier to not have to apologize for being tired, or quiet, or not in the mood to do much.

I reached out to my friend Shaun a couple weeks ago after not seeing him in forever.

His reply: “What is that voice from above? Is that god?”

It made me laugh because I realized then that he got it. He knew I was going through something. He knew my disappearance had nothing to do with him. He wasn’t mad at me, he just missed me.

Example 2: The work criticism

Your boss gives you critical feedback on a project you worked hard on.

You could take it personally: “I’m terrible at my job. They think I’m incompetent. I should just quit.”

Or you could zoom out: Your boss is under pressure from their boss. The company’s going through a rough quarter. They’re stressed and maybe didn’t deliver the feedback well.

The feedback might still be valid—maybe there IS something to improve. But the way it landed had more to do with their stress than your worth.

When you see the full picture, you can extract what’s useful without carrying the emotional weight that isn’t yours.

Example 3: The couple conversation

If your partner asks you to plan more dates or try to keep the house cleaner, that’s not them saying you’re doing something wrong.

It’s them expressing a preference or a need. It has nothing to do with your worth. It’s just information about what would make them feel better.

You can take it personally and spiral, or you can hear it as: “This is what they need to feel good in this relationship.”

Step 5: Recognize that most things aren’t about you

People bring their own:

• Insecurities

• Past experiences

• Bad days

• Projections

• Worldviews

• Triggers

When someone reacts to you, 90% of it is about them.

The critic who says you’re too loud? Maybe they were told to be quiet their whole life.

The person who doesn’t text back? Maybe they’re overwhelmed and can barely text anyone.

The friend who cancels? Maybe they’re going through something you don’t know about.

Your only job is to discern: Is this actually about me? Or is this about them?

Step 6: Build empathy for yourself and others

Not taking things personally doesn’t mean numbing yourself.

It doesn’t mean ignoring feedback.

It doesn’t mean lowering your emotional intelligence.

It means the opposite.

It means having enough empathy and self-awareness to understand:

• What’s yours to own

• What’s theirs to own

• What’s worth addressing

• What’s worth letting go

It means being secure enough to hear criticism without spiraling.

And compassionate enough to see that other people are carrying their own stuff too.

Step 7: Decide what’s worth carrying

You don’t have to carry every opinion, every comment, every piece of feedback.

Some things are worth picking up and working on.

Some things are not yours to carry.

The goal isn’t to care about nothing. It’s to care about the right things.

3. Here’s why it works:

Psychology: Most emotional reactions aren’t about the present moment—they’re about old wounds, past experiences, or existing insecurities. When you stop taking things personally, you’re separating the present from the past.

Empathy: Understanding that people are projecting their own stuff onto you makes you more compassionate. It’s not personal because they’re not even seeing the real you—they’re seeing their version of you filtered through their experiences.

Freedom: When you stop needing everyone to like you, approve of you, or validate you, you get your power back. You can make decisions based on what feels right to you, not what keeps everyone else comfortable.

Clarity: The stuff that’s actually about you becomes obvious. When you’re not drowning in everyone else’s projections, you can see the real feedback clearly.

4. Here’s what to avoid:

Don’t confuse “not taking it personally” with not caring at all.

You can still care about people, care about your work, care about doing well. You’re just not letting other people’s opinions dictate your self-worth.

Don’t use it as an excuse to avoid accountability.

If multiple people are telling you the same thing, and it keeps coming up, maybe it’s not “their stuff”—maybe it’s something worth looking at.

“Not taking it personally” doesn’t mean “ignoring all feedback.”

Don’t mistake detachment for emotional numbness.

Being unbothered doesn’t mean not feeling. It means feeling it, processing it, and deciding whether it’s worth holding onto.

You can be hurt in the moment and still choose not to carry it.

Don’t assume everything is about the other person.

Sometimes it IS about you. Sometimes you did mess up. Sometimes the feedback is valid.

The framework helps you figure out which is which.

Don’t shut down all emotional responses.

The goal isn’t to never be affected by anything. The goal is to not spiral over things that aren’t yours to carry.

5. You’ll know it’s working when:

• You read a critical comment and your first thought is “Is this true?” instead of “I’m the worst”

• A friend cancels plans and you think “They’re probably overwhelmed” instead of “They hate me”

• Someone gives you feedback and you can hear it without your chest tightening

• You post something online and don’t refresh obsessively waiting for validation

• You let things go faster—hours instead of days, minutes instead of hours

• You’re more empathetic, not less—because you see that everyone’s carrying their own stuff

• You feel lighter because you’re not carrying everyone else’s opinions

6. Now go:

Today, try this:

Next time someone says something that stings—a comment, a text, feedback—pause.

Ask yourself:

1. Is this true?

2. Does this upset me?

3. If yes, why? Is it fixable? Is it worth fixing?

Then decide: Is this mine to carry, or can I let this go?

Start here if you only have 10 minutes:

Think about the last thing someone said that bothered you. Run it through the three questions. See what you learn.

Next Tuesday: The Genius Guide to Becoming More Charming (Without Being Fake)

Quick reminder about the *new* Ordinary Genius sending schedule and layout:

Every Tuesday = playbook. Every Friday = real case study 👇

This week’s case study highlights how Trevor Boehm, a Techstars program director, learned to help founders by asking, not telling. Let’s dive in :)

1. Here’s the thing he wanted:

Trevor wanted to actually help founders.

Not just give them advice that sounded smart. Not dispense wisdom from on high. Not tell them what to do and send them on their way.

OKAY PAUSE… some quick context… if you are unfamiliar, Techstars is an accelerator program Trevor and I worked at together.

Every 3 months, 10 startups (and roughly 30-50 founders) would go through our startup “bootcamp” (for lack of a better word). All with the goal of growing their business, raising more funding, and beyond…

okay back to my story…

Trevor wanted founders to leave Techstars having figured something out… something real, something they could act on, something that felt true to them.

The problem was, everyone who came to him wanted answers.

They wanted to be told what to do next.

“Should I raise now or wait?” “Should I pivot or push through?” “Should I hire this person?”

Trevor had been a founder himself. He’d built Frame Agency, a learning design company. He’d co-founded Penny, an Instagram commerce startup. At one point he even sent a bunch of koozies to space. (I’m not joking, I have a koozie from him that says “this koozie went to space”)

He knew what it was like to be in the arena (lol), making decisions with incomplete information and just wanting to know what to do next.

He could have just given advice. He had opinions. He had experience.

But he realized something: when you tell people what to do, they might follow your advice… but they don’t own the decision. And if (or when) it doesn’t work out, they blame you. Or worse, they never build the muscle to figure things out themselves.

He wanted something different. He wanted founders to leave knowing what they thought, not what he thought.

So he stopped giving advice… and he started asking questions… good questions.

2. Here’s how he did it:

Trevor’s approach was deceptively simple: he just repeated back what founders said to him, in a different way.

A founder would come in: “I don’t know if I should focus on growth or product right now.”

Most mentors would say: “You should focus on growth” or “Product has to come first.”

Trevor would say: “What are you really trying to solve right now?”

And then he’d shut up.

The founder would pause. Think. Then start talking through it themselves.

“Well, we have users, but they’re not sticking around...”

Trevor: “What happens if they don’t stick around?”

“We lose them and have to keep acquiring more, which gets expensive...”

Trevor: “So what does that tell you about where to focus?”

“...I guess we need to fix retention before we scale.”

and just like that, the founder just solved their own problem.

Trevor didn’t tell them what to do. He asked clarifying questions until they surfaced what they already knew.

The Questions He Actually Used:

• “What are you really trying to solve?”

• “What happens if you don’t do this?”

• “What’s the version of this that feels true to you?”

• “What are you optimizing for?”

• “What would this look like if it were easy?”

Simple questions. No tricks. No clever frameworks.

Just genuine curiosity and the discipline to not jump in with answers or absolutes.

The Move That Made It Work:

The key was what he did after asking the question: he waited.

Most people ask a question and then fill the silence with their own thoughts, or another question, or a story about themselves.

Trevor just sat there. Comfortable with the discomfort.

That silence forced founders to think. To process. To articulate what they actually believed instead of just reacting.

Founders would look at him like, “Aren’t you going to tell me what to do?” but eventually they’d start talking. And once they started, they’d figure it out.

3. Here’s what it cost him:

Time.

Asking questions instead of giving answers takes longer. You can’t just tell someone what to do and move on. You have to sit with them. Wait for them to process. Ask follow-ups.

Trevor spent hours in office hours with founders. Not because he was slow but because he was doing the harder, more helpful thing.

Risking being seen as “not helpful” at first.

Some founders left his sessions thinking, “He didn’t even tell me what to do.”

They wanted a “guru”. They wanted someone to hand them the answer.

Trevor didn’t do that. And early on, some people interpreted that as him not knowing the answer, or not wanting to help.

It took time for founders to realize: the ones who worked with Trevor ended up making better short AND long term decisions than the ones who just collected advice from everyone else.

The discipline to shut up.

This is harder than it sounds. When someone asks you a question, the instinct is to answer it. Especially when you have an answer.

Trevor had to constantly fight the urge to jump in with “Here’s what I would do.”

He had to trust that founders were capable of figuring it out themselves even when it would have been faster to just tell them.

4. Here’s why it worked:

Psychological ownership.

When you tell someone what to do, it’s your idea. When they figure it out themselves (with your questions guiding them), it’s their idea.

People execute on their own ideas way harder than they execute on someone else’s advice.

It built the muscle.

Founders who worked with Trevor didn’t just solve one problem… they learned how to think through problems.

So the next time they got stuck, they didn’t need Trevor. They could ask themselves the same questions, walk themselves through the same process. Whether they realized it or not, Trevor gave them a framework for long term success.

It was actually more honest.

Trevor didn’t pretend to have all the answers. He wasn’t performing expertise.

He was genuinely curious about what the founder was trying to do, and he helped them surface their own thinking.

Founders trusted him because he wasn’t trying to be the smartest guy in the room. He was trying to help them be smarter, and he was trying to understand their thought further in the process.

It separated the serious founders from the advice collectors.

A lot of people just want to be told what to do. Either they are overwhelmed, or they aren’t confident in what they are building, or they want to try and alleviate some stress or responsibility from making mistakes.

Trevor’s approach filtered those people out. The founders who stuck with him were the ones willing to do the hard thinking themselves and those were the founders who actually built something.

5. Here’s what he avoided:

He didn’t give advice just to sound smart.

Plenty of mentors want to show off how much they know. They jump in with war stories and frameworks and tactical advice… not because the founder needs it, but because it makes them feel useful.

Trevor avoided that trap.

He wasn’t there to perform. He was there to help.

He didn’t ask leading questions.

A leading question is when you’ve already decided what someone should do, and you’re trying to guide them to your answer.

“Don’t you think you should focus on growth right now?”

That’s not a real question. That’s just advice disguised as a question.

Trevor asked clarifying questions… genuine curiosity about what the founder was thinking, not steering them toward a predetermined conclusion.

He didn’t fill the silence.

Most people can’t handle the awkward pause after asking a question. They jump in with more explanation, or a story, or another question.

Trevor just waited and sometimes when you wait long enough magic happens.

He didn’t try to be everyone’s guru.

Some mentors want to be the go-to person for every decision. Trevor built founders who could think for themselves.

Which meant they needed him less over time and that was the point.

6. Now go:

This week, try this:

Pick one conversation… could be with a friend, a colleague, someone on your team… where you’d normally give advice.

Instead, ask: “What are you trying to solve?”

Then shut up. Let them think. Don’t fill the silence.

See what happens.

Bonus: Here’s what you can steal from Trevor

1. Replace “Here’s what I would do” with “What are you optimizing for?”

2. Get comfortable with silence… let people at least try to figure it out

3. Ask clarifying questions, not leading ones

4. Trust that people are capable of finding their own answers

5. Your job isn’t to be the smartest person in the room… it’s to help others think clearly

Next week: The Genius Guide to Not Taking Things Personally

P.S. Trevor now works as an Operating Partner at Saturn Five, he also wrote a book called Levers: The Framework for Building Repeatability into Your Business. If this story resonated, hit reply and tell me what topics you want to see us cover next. I read every response.

Writing from Austin and very full still from Thanksgiving,

Your question master, Alex

Hey y’all!

Welcome to the *new* Ordinary Genius.

New sending schedule:

Every Tuesday = playbook. Every Friday = real case study.

New layout:

Here’s the thing you want

Here’s how to do it

Here’s why it works

Here’s what to avoid

You’ll know its working when…

Now go!

Have any feedback? Reply directly or DM me anywhere @heyalexfriedman.

Today we’re covering how to ask better questions. Not networking tips, or sales jargon. The real stuff like how to have conversations that actually matter.

Writing this from Austin, Texas. Let’s go!!

Here’s the thing you want:

You want to be the person people want to talk to.

Not because you’re the loudest or the most interesting… but because when you ask a question it’s obvious that you MEAN it. The conversation gets better, people open up, small talk disappears, and everyone leaves feeling like you actually got them.

Good questions do that. Most people ask terrible questions lol

They ask what they think they’re supposed to ask: questions designed to make themselves look smart, leading questions because they already decided what the other person should do, etc.

You don’t have to be that person!

Here's how to do it:

Step 1: Stop trying to sound smart

The best questions aren’t clever. They’re simple.

When I worked at Techstars, my coworker Trevor was the master at this. Founders would come to him stuck on some decision, and instead of telling them what to do, he’d just… ask questions. Simple ones likeeeeee……..

“What are you trying to solve here?”

“What happens if you don’t do this?”

“What’s the version of this that feels true to you?”

He wasn’t performing. He was genuinely curious. And somehow, founders would leave his office having solved their own problem.

Your job isn’t to have the answer. It’s to help them find theirs.

Step 2: Don’t ask leading questions

Leading question: “Don’t you think you should focus on growth right now?”

(Translation: I’ve already decided what you should do, and I’m trying to get you to agree.)

Clarifying question: “What’s making you feel like you need to choose between growth and product right now?”

(Translation: I’m genuinely trying to understand your situation.)

The difference is massive. One makes people defensive. The other makes them think.

The pattern: Repeat back what they said in a different way. That’s it. It sounds simple, but most people never do it because they’re too busy thinking about what they want to say next. Pushing someone deeper on their own question allows them to process their thoughts further. Usually they will find the conclusion on their own (and still give you the credit for finding it)

Step 3: Use the “What” and “How” framework

These are your power words:

• “What are you optimizing for?”

• “What would this look like if it were easy?”

• “How are you thinking about this?”

• “What’s the thing you’re not saying?”

Notice: no “Why” questions. “Why” makes people defensive. “What” and “How” make people reflective.

Step 4: Go one level deeper

Most people stop at the surface answer. You want the second or third layer.

Surface: “What are you working on?”

One level deeper: “What part of that are you most excited about?”

Two levels deeper: “What would success actually look like for you?”

The first question is small talk. The third question is a real conversation.

Step 5: Make it context-appropriate

On a date:

Bad: “What do you do for work?”

Better: “What’s keeping you busy these days?”

Even better: “What’s something you can’t stop thinking about lately?”

In a meeting:

Bad: “Don’t you think we should do X?”

Better: “What are the trade-offs you’re seeing?”

Even better: “What outcome are we optimizing for here?”

As a mentor/advisor:

Bad: “Here’s what you should do…”

Better: “What options are you considering?”

Even better: “What would you do if you weren’t afraid?”

Step 6: Listen for the real answer

The first answer is rarely the real answer.

Someone says, “I’m fine.”

You say, “Lol what does FINE mean?”

They pause, loosen up, then get to the actual answer.

Your job is to create space for the real answer to come out. That means being comfortable with silence. That means not jumping in with your own story. That means actually listening instead of waiting for your turn to talk.

Step 7: Process out loud when you’re not sure what to ask

It’s okay to say:

• “I’m trying to understand what you mean by that… can you say more?”

• “I’m processing this… help me make sure I’m getting it right.”

• “I don’t know what to ask yet, but this is interesting. Keep going.”

You don’t have to have the perfect question ready. Sometimes the best move is admitting you need more information or time to ask a better follow up.

Here’s why it works:

Psychology: People already know their answers. They just need someone to help them surface it. When you ask clarifying questions instead of giving advice, you’re treating them like they’re capable of figuring it out.

Culture: We’re in a world where everyone’s talking, nobody’s listening. When you actually ask thoughtful questions, you stand out. You become the person people want to talk to… not because you’re impressive, but because you make them feel heard.

Strategy: Good questions build trust faster than anything else. They show you’re paying attention. They show you care about the other person’s perspective, not just your own. In business, in relationships, in life… that matters more than you think.

Here’s what to avoid:

Don’t ask questions to feed your own ego.

If you’re asking a question to show off how much you know, stop. It’s transparent, and it makes people not want to talk to you.

Don’t ask “gotcha” questions.

Questions designed to trap someone or make them feel dumb aren’t questions. If your goal is to prove someone wrong, you’ve already lost the conversation.

Don’t ask when you’ve already decided the answer.

Leading questions are manipulative. If you’ve already decided what someone should do, either say it directly or don’t say anything. Don’t pretend to be curious when you’re not.

Don’t over-complicate it.

Simple questions are better than clever ones. “What do you mean by that?” Or “Can you tell me more about that?” is often the best question you can ask.

Don’t fill the silence.

After you ask a good question, shut up. Let them think. Let them sit with it. The silence is where the real answer lives.

You’ll know it’s working when:

• People start opening up to you more

• Conversations feel less like interviews and more like actual exchanges

• You walk away understanding what someone actually meant, not just what they said

• People tell you “I’ve never thought about it that way before”

• You stop feeling like you have to have all the answers

• Silence doesn’t feel awkward anymore, it feels productive

Now go!

Today: Pick one conversation…

a meeting, a coffee, a phone call and commit to asking one clarifying question instead of giving advice.

Try: “What are you optimizing for?” or “What would this look like if it were easy?”

Then do the hardest thing: shut up and listen.

Start here if you only have 10 minutes:

Replace “Why did you do that?” with “How are you thinking about that?” in your next conversation. Notice what changes.

Trying out a new format to write the best newsletter ever written,

Your friend Alex

Thank you for all the great feedback over the last couple of weeks. It’s been so insanely helpful to know what resonates so we can continue to refine the newsletter and make it as valuable as possible.

So, our quick update: We are currently working on our ✨new ✨format and moving platforms.

To hold you over, I wanted to share something practical: a playbook for monetizing a small audience.

It doesn’t matter if you have 100 followers or a 1,000,000… you can monetize.

So, whether you’re building a side project or thinking about going full-time on your own thing, this breaks down how to turn even a modest following into actual, real revenue.

Thanks for being a part of the ride. I appreciate it.

Talk to you next Tuesday <3

Alex

💡 Thanks for being here! Know someone who would love Ordinary Genius? Don’t forget to forward this.

Share Ordinary Genius

No big pitch here, but y’all filled our calendar in August for sprints so we hired a new team member (Welcome, Lauren!) and are opening a few more slots for brand audits and ghostwriting in September.

If you are a founder, coach, or VC and want clarity + speed in building your brand online and offline, let’s chat!

Let’s get into this weeks newsletter…

Ever notice how the most successful people you know… aren’t the ones who always make the perfect call?

They’re the ones who make calls, period.

Meanwhile, you’re stuck weighing pros and cons, reading another book, asking five more people what they think. By the time you’re “ready,” the opportunity’s gone, or it feels too late.

Decisiveness isn’t about being right. It’s about trusting yourself to handle being wrong.

Why This Has Been on My Mind

I recently started re-reading Decisive by Chip and Dan Heath. I’ve struggled with making quick decisions. From ordering ice cream as a kid, to picking my favorite font as an entrepreneur.

My mind would get wrapped up in the optionality, and worrying what if I make a wrong choice and regret it?

About 8 years ago my friend Naz (shoutout, Naz—you’re probably reading this!) invited me a lecture where Chip Heath was speaking.

After enjoying his other book The Power Of Moments, I started reading Decisive and one line stopped me cold: “Prepare to be wrong.”

It hit because I realized how much of my indecision wasn’t about choosing… it was about wanting guarantees.

But life doesn’t hand out guarantees and the people who win big don’t wait for them.

The Heath brothers call out four villains that stall decisions:

• Narrow framing (thinking it’s “this or that”)

• Confirmation bias (seeking proof you’re right instead of testing assumptions)

• Short-term emotion (letting temporary feelings sway the call)

• Overconfidence (believing you can predict the future too well)

Their antidote is the WRAP framework:

• Widen your options

• Reality-test assumptions

• Attain distance before deciding

• Prepare to be wrong

The Core Reframe

We think indecision protects us from mistakes.

Really, it just delays progress.

Jeff Bezos used to say: if you’ve got 70% of the information you wish you had, that’s enough. Make the call. Waiting for 90% is usually waiting too long.

Here’s where Bezos and the Heath brothers overlap beautifully:

• Bezos gives you speed (act at 70%).

• The Heaths give you safeguards (WRAP to avoid obvious traps).

Put together, you get a system that’s both fast and resilient. Bezos ensures you move, the Heaths ensure you don’t move blind.

5 Moves to Build Decisiveness Immediately

Here are some simple guidelines to consider when turning you’re expertise Into a service.

1. Apply the 70% Rule

If you’ve got most of the data, stop waiting. Bezos used this to scale Amazon. It forced momentum and left room for course correction.

2. Put a Timer on Decisions

Give yourself 24 hours (or less) for most choices. Time limits force clarity.

3. Flip the Script: “What’s the Cost of Waiting?”

We obsess over the risk of the wrong move… but rarely calculate the hidden cost of delay.

4. Practice Micro-Decisions

Order the first thing on the menu. Take the first flight option. Send the first draft. For once, don’t overthink it. Small calls stack into instinct.

5. Audit Who You Ask for Advice

Every extra opinion adds friction. Pick 1–2 trusted filters, not a committee.

Genius Tips: Decisiveness Reframes

• Perfect timing is a myth.

• Waiting is a decision—usually the worst one.

• Speed compounds. A decent decision now beats a perfect one later.

• Progress loves momentum more than accuracy.

• Confidence doesn’t come from being right. It comes from moving forward anyway.

If You Take Nothing Else From This

Decisiveness isn’t about knowing the future.

It’s about stacking evidence that you’ll survive mistakes AND adjust as you go.

That one shift flips the script: from paralysis over being wrong → to proof that you can handle being wrong.

And if you want a deeper dive, Decisive by Chip and Dan Heath is the best breakdown I’ve read on how to escape the mental traps that keep us stuck.

thoughtfully, yet quickly

— alex 💭 (@heyalexfriedman)

P.S. Forward this to a friend who’s stuck “thinking it over” for the 10th time.

P.P.S. if you missed it at the top… Y’all we are opening just a few more slots for September. If you are a founder, coach, or VC and want clarity + speed in building your brand online and offline, let’s chat!

That gut-wrenching feeling before a big move—your first cold call, product launch, or bold risk. And yet, we’re constantly told: “Be fearless.”

That advice? Garbage.

The best entrepreneurs aren’t fearless. They’re terrified. But the difference? They act anyway.

Fear Isn’t a Stop Sign. It’s a Green Light.

Fear doesn’t mean you’re weak or unprepared—it means you’re about to do something that matters. If you’re never scared, chances are you’re playing too small.

Your brain screams, “Danger!” But what if, instead of stopping, you took it as a cue to move forward?

Fear is just your mind saying, “Hey, this is important.”

The best entrepreneurs don’t let fear paralyze them—they harness it.

The question isn’t “How do I stop feeling afraid?”

It’s “How do I move forward even when I am?”

How Fear Shows Up in Entrepreneurship

1) Fear of Rejection

You put yourself out there—your product, your pitch, your ideas. Then the fear kicks in:

❌ What if they say no?
❌ What if they don’t get it?
❌ What if they ignore me?

Feels personal, right? But what’s the alternative? Playing it safe and never knowing?

Rejection isn’t failure. It’s proof you’re in the game.

Genius Tips:

🧠 Reframe rejection as redirection. Every “no” is feedback, not failure—use it to refine your approach.

🧠 Make rejection the goal. Aim for 50 no’s. The more you get, the more you’re putting yourself out there—and the closer you are to a yes.

2) Fear of the Unknown

What if it flops? What if no one cares? What if I lose money?

Entrepreneurship is betting on an uncertain future—and that fear never fully goes away. But if you learn to sit with the discomfort, that’s where the biggest breakthroughs happen.

The best founders aren’t fearless. They’re just really good at moving through uncertainty.

Genius Tips:

🧠 What if it works? Your brain defaults to worst-case scenarios—flip it. Focus on what could go right.

🧠 Test before you leap. Launch a small, low-risk version of your idea today. Clarity comes from action, not overthinking.

3) Fear of Not Being Good Enough

Imposter syndrome? Everyone feels it. Even the most successful entrepreneurs hear that little voice whisper, “Who do you think you are?”

But here’s the thing: Feeling unqualified isn’t a flaw. It’s a sign you care. It’s a sign you’re growing.

If you’re always growing, you’re always stepping into new territory—so of course fear is coming along for the ride.

The goal isn’t to eliminate fear. It’s to move forward anyway.

Genius Tips:

🧠 Confidence follows action. Stop waiting to feel ready—just start. Growth happens in motion.

🧠 Read your own receipts. Keep a list of past wins. When imposter syndrome hits, remind yourself what you’ve already conquered.

How to Handle Fear Like a Pro

✅ Embrace It. Fear isn’t the enemy—it’s part of the process. The more you avoid it, the more power you give it.

✅ Reframe It as Excitement. That racing heart? Sweaty palms? It’s just energy. Instead of thinking, “I’m terrified,” tell yourself, “I’m excited.” Your brain doesn’t know the difference.

✅ Take Small, Calculated Risks. You don’t have to go all-in at once. Test. Tweak. Adjust. Every small risk makes the big ones easier.

✅ Trust Yourself (Even When You Don’t Feel Ready). No one ever feels 100% ready. The best entrepreneurs act before they feel prepared.

Fear = Fuel

Fear isn’t a sign to stop. It’s proof you’re pushing boundaries.

The best entrepreneurs don’t wait for fear to disappear. They use it as fuel.

So the next time fear shows up? Take it as a sign you’re headed in the right direction.

Until next time,
Alex Friedman

P.S. What’s the biggest fear you’ve had to push through on your entrepreneurial journey? Tweet me let me know—I’d love to hear your story.

P.P.S. If you’re looking for part time roles while you supplement your income, subscribe to our sister newsletter FounderGigs!