I turn 40 soon.
I always thought life would make more sense by now. It hasn't.
What has happened is a series of hard resets, wake-up calls, and lessons I never expected to learn.
Some things, I had to unlearn—beliefs I once held that turned out to be wrong.
Some things, I just had to learn the hard way.
Here they are.
On Life, Friendship & Relationships
1. Friendships don't break over one mistake. They break from years of unspoken shit.
I lost one of my closest friends after a day of drinking. I messed up. I apologized. She still cut me out of her life.
At first, I thought she overreacted. But I've realized it wasn't just about that night—it was about years of things unsaid.
The silver lining? That night made me quit drinking.
She doesn't know it, but losing her might have saved me from something worse.
2. At 36, I thought I'd built the life I wanted. Then it fell apart.
I met my ex-wife two months into COVID. Lockdowns accelerated everything. We spent nearly every day together, and in that kind of isolation, it felt like we really knew each other.
And in many ways, we did. She's an incredible person. I was experienced enough in dating to feel confident in what I was looking for, and at the time, I truly believed we were aligned.
But COVID also hid the natural friction that comes from experiencing life together. The world was small. Routines were simple. There were fewer opportunities to see the places where we weren't compatible.
It wasn't until things opened back up—when life reintroduced complexity—that we started to see the gaps. And by then, we were married.
I don't regret it. I learned so much about myself, about relationships, about what really matters in a partner.
But I also learned that some things can only be revealed through time and experience—and that's no one's fault.
3. If you're thinking about ending things, tell someone. But don't expect them to know what to do.
I wrote a suicide letter to my parents. I never sent it.
Later, when I started turning things around, I told a few friends—not as a cry for help, just to share.
I expected concern. A reaction. Something. But… no one really said much. That surprised me.
Maybe they didn't know what to say. Maybe I expected something they couldn't give.
Looking back, I know this: I should have told someone sooner.
4. You don't think your way into feeling better. You move first.
I was stuck in my head. I tried to think my way out of it. That never worked.
Then I learned: You don't change how you feel by thinking differently. You change it by moving.
Tony Robbins drilled this in: "Move your body first. Your mind follows."
It sounded simplistic. But it worked.
5. I used to think my ability to read people was a superpower. Then I realized it made me lose track of what I actually want.
I've had to come face-to-face with my people-pleasing tendencies.
At 40, it's gotten to a point where I don't always know what I want—I just know how to read what other people want. And that's dangerous.
If you spend your life accommodating others, you end up disappointing both of you.
6. I thought NYC was home forever. Then I looked up and realized I had already left.
I moved to NYC the day after college, hellbent on taking over the world. I built companies, a career, a network.
Then COVID happened. Suddenly, I felt isolated. My company was remote. Most of my friends had left.
I realized: The version of me who thrived in NYC didn't exist anymore.
On Growth, Resilience & Reinvention
7. I thought I had to follow my original dream. Turns out, dreams evolve.
What do I actually want vs. what have I just been chasing because I always have?
8. They say people don't change until they have to. That was true for me.
For me, that point wasn't some grand realization. It was knowing I'd f*cking die if I didn't change.
- That's what it took to quit drinking.
- That's what it took to lose 50lbs.
- That's what it took to pull myself out of my lowest point.
9. Low testosterone will f*ck your life up.
🚨 Low testosterone
🚨 High estrogen
🚨 Cortisol, dopamine, and serotonin were shot from chronic stress
Doctor's words: "You've been physiologically PMSing for a long time."
I had no idea how much this was affecting my energy, resilience, and mental state.
Got on TRT—and within two weeks, I felt normal for the first time in years. Not great, just normal. And that changed everything.
10. I used to think I was missing the right strategy. Sometimes, I was just missing the right people.
The biggest inflection points in my life didn't come from new strategies.
They came from new relationships.
- People who challenged me.
- People who opened doors.
- People who made me see things differently.
11. I thought getting in shape was about motivation. It's not. It's about removing decisions.
I didn't wake up and ask, "What should I eat?"
I didn't debate, "Should I go to the gym?"
I built systems so I didn't have to think about it.
Motivation fades. Systems last.
12. I used to think breakthroughs came from thinking harder. Turns out, they come from breaking patterns.
When my marriage ended and my business was on the verge of collapse, I was completely stuck. Overthinking. Analyzing every move. Trapped in my own head.
I tried everything—books, journaling, talking it out. Nothing helped.
Then I did Ketamine therapy.
My parents would probably question it. A lot of people would.
But in six sessions, I moved through more emotional weight than I had in months.
It didn't "fix" me. But it shook me out of paralysis. It gave me enough space from my own thoughts to see a way forward.
Sometimes, the thing that actually works isn't what you expect—or what makes sense to other people.
13. My therapist is f*cking awesome.
Not because she just listens, but because she challenges me. She calls me out on my own bullshit, helps me see the patterns I miss, and gives me practical ways to move forward.
I'm a cynical, sarcastic New Yorker living in Venice, California.
She jokes that I'm "woo-curious"—open to the spiritual/energetic side of things, but still skeptical.
And she meets me exactly where I am, pushing just enough to expand my perspective without losing me in the process.
14. I don't need balance. I want people who are just as obsessed as I am.
I don't want balance. I want flow. I want a team that's locked in.
I want to do the best f*cking work of my life, with people who want the same.
On Execution, Leadership & Playing to Win
15. Everything changes when you realize no one is coming to save you.
Stop waiting for the perfect market conditions.
Stop waiting for someone to tell you you're ready.
Stop waiting for some external validation.
That doesn't mean we shouldn't take care of each other—we absolutely should. But you cannot afford to sit still.
It's on you. And once you accept that, everything becomes simpler.
16. The best opportunities didn't look like opportunities at first.
I've said "yes" to things that made no logical sense.
A conference I couldn't afford.
A role I wasn't qualified for.
A move to a new city without a real plan.
In hindsight? Those were the biggest unlocks of my life.
17. Some people want to win. I refuse to quit.
I don't work just to stay busy. I don't build just to build.
I need to win. Not for validation. Not for status. But because pushing forward is the only thing that makes me feel alive.
18. I used to think failure was the worst thing that could happen. It's not. Stagnation is.
A failed business. A failed relationship. A bad investment.
None of that will kill you.
But sitting in the same place, repeating the same mistakes, running the same loops? That will.
19. The more successful someone is, the less they judge you for trying.
The loudest critics are never the people who've done sh*t. They're the ones on the sidelines.
The people at the top? They respect the game. They respect effort.
20. I used to think successful people had it all figured out. Turns out, nobody does.
The truth? Nobody really knows what they're doing. Some just move forward anyway.
21. I thought I needed to trust the process. I actually needed to trust myself.
The process works—but only if you stay in it.
There have been times when I second-guessed everything. My decisions, my strategy, my instincts.
Every major win I've had came when I trusted myself just a little longer than I wanted to.
22. I do my best work when I'm NOT scared.
Some people do their best work with their backs against the wall. That's not me.
I thrive when I feel clear, calm, and safe to experiment & f*ck up.
23. I thought I was bad at sales. Turns out, I was bad at asking for what I wanted.
I used to think sales was some magical skill I didn't have. It's not.
It's just the ability to be clear and direct about what you want—and why it's worth it.
That applies to business, relationships, and every major decision.
24. I don't need to be the best. I just need to stack the right skills.
I'm not the best programmer.
I'm not the best marketer.
I'm not the best operator.
But I'm good enough at all three. And that combination is my unfair advantage.
Success isn't about being the best. It's about stacking skills in a way that creates leverage.
25. The difference between a bad business and a great one is a pivot you didn't see coming.
I've been one pivot away from success multiple times.
Some I made. Some I missed. Some I made too late.
Now, I know: You don't just need vision. You need to know when to shift.
26. Success is a lagging indicator of consistency.
If I look at every big win I've had, it didn't come from some magical moment—it came from showing up over and over until something clicked.
Talent matters, but consistency is the great equalizer.
27. Most problems in business aren't business problems. They're people problems.
Every major challenge I've faced in business has boiled down to one of three things:
1️⃣ The wrong people in the wrong seats.
2️⃣ The right people, but misaligned incentives.
3️⃣ A leadership issue I didn't want to admit.
Hiring, incentives, and leadership. If you can solve for those, you can solve for almost anything.
28. The best deals aren't found. They're made.
There's rarely a perfect hire, investor, acquisition, or business model.
But if you understand leverage, incentives, and timing, you can create great deals. You can engineer great outcomes.
29. Everything is hard when you suck at it.
Lifting weights is hard—until you get strong.
Sales is hard—until you get reps.
Public speaking is hard—until you stop sucking.
Most things aren't hard. Being bad at them is.
30. The best way to attract great people is to be someone they want to work with.
If you want to work with brilliant, talented, driven people—you better be someone they're excited to build with.
Standards. Work ethic. Integrity. Vision.
Good people don't follow titles. They follow energy.
This goes for personal life and business.
31. The worst person to take advice from is someone who's never done it.
I've been given so much bad advice from people who have never built anything.
The best "advisors" I know? They give less advice. They ask better questions.
If you're taking advice, check the track record.
32. People are going to make up stories about you. Let them.
You can't control what people think about you. You just have to keep building.
33. The worst decisions I've made came from trying to force something that wasn't working.
Every time I've forced something—a business model, a partnership, a launch, a relationship—I knew it wasn't right.
I just didn't want to admit it.
Now, I listen to that hesitation.
34. I used to think I needed perfect clarity before making a big decision. I don't. I just need forward motion.
I didn't have a perfect plan when I quit drinking.
I didn't have a perfect plan when I pivoted my business.
I didn't have a perfect plan when I moved to LA.
I just knew one thing: Staying where I was wasn't an option.
35. I used to think momentum was just about hard work. It's actually about eliminating friction.
Some people grind 12-hour days and never get anywhere. Others work strategically and make it look easy.
Every time I've gone from stuck to unstoppable, it wasn't because I pushed harder. It was because I got rid of what was slowing me down.
The wrong hire. The wrong market. The wrong mental loop.
Momentum isn't about forcing speed. It's about clearing the path.
36. If you're always the smartest person in the room, you're in the wrong room. If you're never the smartest person in the room, you're in the wrong life.
I want to be around people who challenge me, but also spaces where I bring something unique to the table.
Too much of either is suffocating.
37. I used to think persistence was about pushing harder. Sometimes, it's knowing when to walk away.
I've had moments where I was fighting for something that wasn't working.
A business model.
A product.
A partnership.
I told myself it was grit. But grit without awareness is just stubbornness.
Sometimes the smartest move isn't "push harder."
Sometimes the smartest move is "let it go."
38. I thought I needed to be smart. I actually needed to be resourceful.
I've met insanely smart people who get stuck in analysis paralysis.
I've met people who weren't the smartest, but they adjusted faster than anyone else.
The ones who win aren't the smartest. They're the ones who adapt the fastest.
39. Every founder has one big regret: Not trusting their instincts sooner.
Every time I've ignored my gut, I've regretted it.
A hire that didn't feel right.
A deal I knew I shouldn't take.
A product I knew wasn't going to work.
Now, I trust my instincts faster. It doesn't mean I'm always right. But it means I don't waste time fighting what I already know.
40. When things go bad, act fast. When things go well, slow down.
When things are breaking, speed up. Cut the bad hire. Kill the bad product. Pivot fast.
When things are working, slow down. Stay focused. Don't chase shiny objects. Let momentum build.
Most people do the opposite.
41. Money doesn't buy happiness. But financial freedom buys peace.
I don't need more money. I need money that keeps buying me optionality.
Not worrying about rent. Not worrying about burn. Not having to take bad deals.
The goal isn't "more." The goal is freedom to move how I want.
42. I thought I didn't have time for a dog. Turns out, dogs make life better no matter how busy you are.
I want a mini golden retriever. Yes, I know they shed. Everywhere. All the time. I do not care.
43. I've built great products that failed. I've built mediocre products that made millions.
Execution > ideas.
Distribution > features.
Market timing > everything.
Some of the best things I've built never took off. Some of the things I didn't think were special made millions.
You don't get to decide what the market values. You just have to pay attention.
44. The best people I've worked with all have one thing in common: They care more than they need to.
You can't fake obsession. You can't force someone to care.
The people who do the best work of their lives? They give a sh*t beyond the paycheck.
That's the only kind of person I want to work with.
45. Every major pivot I've made started with a conversation.
Not a grand strategy session. Not a whiteboard exercise. A single conversation.
A mentor pointing out what I wasn't seeing.
A friend challenging my thinking.
A chance encounter with someone who changed my perspective.
If you're stuck, talk to people who've already solved your problem.
46. Most people quit before the inflection point.
Growth isn't linear. It looks like nothing, nothing, nothing… then everything all at once.
Every founder I know has been on the edge of quitting right before a breakthrough.
Most people don't lose because they aren't capable. They lose because they stopped too soon.
47. If you don't write things down, you'll convince yourself you haven't made progress.
I used to feel like I wasn't getting anywhere—until I actually looked back at where I was a year ago.
Your brain will always tell you you're behind.
That's why you need real evidence that you're moving forward.
Write it down. Track it. Revisit it.
48. There's no such thing as a perfect decision—just the next best move.
Most decisions aren't right or wrong. They're move forward or stay stuck.
I used to obsess over making the perfect choice. Now, I just focus on making the next best move.
49. You can't build something meaningful if you're constantly distracted.
Most people don't fail because they don't have good ideas. They fail because they chase too many at once.
The times I've made the most progress? When I cut the noise and focused.
50. A business without a strong point of view is forgettable.
Nobody cares about "just another" product.
The strongest brands, founders, and companies stand for something. They challenge something.
If your product doesn't have a clear, strong opinion, it's probably not worth building.
51. Most things don't need more time. They need more intensity.
I've had weeks where I got more done than in the previous three months combined.
Not because I worked longer. But because I went all in.
Most people trick themselves into thinking they need more time. They just need to turn up the intensity.
52. The difference between a $10K problem and a $1M problem is the questions you ask.
If you're stuck, you're probably asking the wrong questions.
❌ "How do I get more customers?"
✅ "How do I make customers feel like they'd be stupid not to buy?"
❌ "How do I raise money?"
✅ "How do I create leverage so investors feel like they need to bet on me?"
The right question changes everything.
53. I used to think I had to figure everything out on my own. Then I realized I just needed better questions.
Every time I've been stuck, I didn't need an answer—I needed a better question.
❌ Instead of: "How do I fix this?"
✅ Ask: "Who's already figured this out?"
❌ Instead of: "Why isn't this working?"
✅ Ask: "What part of this is actually working?"
The right question will get you further than the best answer.
54. I used to think I needed to have all the answers.
Now, I know the goal is just to keep asking better questions.
