Happy Monday!

I hope you had an incredible weekend. I just got off a three day cruise and it honestly changed my life.

Cruises normally get a bad rap. I’m the first to talk shit on the unlimited booze, terrible farmers tans and having my eyes on people who look like they shouldn’t be let out in public. But this was different!

Three days, 2,000 entrepreneurs going to Bahamas. It was for an event called Summit at Sea, and I'm still trying to make sense of what I felt out there.

The boat was filled with some of the highest performing humans on earth. People who have sold companies for billions. People responsible for creating companies that have changed the world. Multiple exit founders. The guy responsible for implementing AI at Microsoft. An amazing guy from Austin building a Neuralink competitor and is inplanting his first human in July. Fortune 500 CEOs. Folks from other communities like YPO, EO, and Tiger 21. Family offices run by thirty year olds who are now managing billions. And amongst them, were Founders Club members everywhere. Every conversation I had, the person across from me was building something that mattered.

There were over 250 events on that boat over three days. Panels, workshops, workouts, jam bands, fireside chats, dinners, breakouts. I went to a handful. I took some notes. I shook a lot of hands.

And here's the thing I can't stop thinking about.

I don't remember a single talk.

Not one. Not a quote, not a slide, not a stage moment. We make so much of having the “best speakers” at The Founders Club and putting so much pressure on securing the best guests but what I remember are actually the conversations with the people in the room.

And what I noticed across those conversations, dozens of them over three days, was a pattern I wasn't expecting.

Almost everyone was carrying something heavy.

The guy who sold his company for a number most people will never see in their lifetime, telling me he can’t sleep at night because he is so stressed with how to manage his new financially free life. The Fortune 500 CEO who couldn't stop checking his email at dinner. The founder mid-raise who was $2M short on her round, hoping that her pitch on the boat was going to let her secure her funding needed for inventory for the largest order of her life. The guy who'd technically retired at 38 and was already trying to figure out what to start next, not because he was bored, but because his wife divorced him and now the silence felt worse than the grind.

I had a version of this conversation maybe a dozen times. Different people. Different industries. Different zeros at the end of their net worth. Same song.

Two thousand of the most successful people I've ever been around in one place, and a huge percentage of them were quietly carrying a version of the same exact problem.

I’ve been sitting with this for the last few days.

I grew up with very little.

Most months we relied on government money. Mom worked as a high school secretary. Dad was in and out of jobs, and money was always something we didn't have enough of. There's a specific memory I have of standing in our kitchen, maybe twelve years old, watching my parents open a stack of mail at the counter. They weren't crying. They weren't saying anything. Just slowly working through the envelopes with the particular stillness of someone doing math they didn't want to do. I didn't know the word "mortgage" yet in the way I know it now. I certainly didn't know the word "foreclosure." But I knew that look. I've been chasing the opposite of that look for the last twenty years.

Then my dad died when I was 18. Heart attack. He died in my arms. We didn't have a financial cushion or a network or a plan. Hell I spent my entire portion of his life insurance plan on a $7000 Canon 5D Mark II camera and my brother bought a Pontiac G6.

What we lacked in money was pure grit and belief that I could change my life. Despite all the bullshit I was up against, I was fully in control. With just enough education, a few introductions, a few good ideas, and resilience, I was going to be okay.

So I did what I thought I was supposed to do. I went to college. I signed up for a life of imprisonment with this thing called student loan debt. I came out with $200,000 at a 16% interest rate. A death sentence. One that I know at 33 very clearly, but 17 year old Chris had no idea. The plan had ended with me $200K deeper into the same hole my family had been in my whole life.

I struggled for years with shitty corporate jobs paying me the bare minimum, scrapping up just enough money to pay my rent, the loan, and having enough money for a Friday night pizza. There was no light at the tunnel. There was no way out. My only escape was starting something on my own.

Entrepreneurship is what got me out. CROSSNET was a brutal, beautiful eight-year run that eventually let me clear that debt and then some. I sold the company. I got the exit. I crossed the line I'd been chasing since I was a teenager standing in that kitchen wondering how my parents were going to keep the lights on.

And here's what I'm finally honest enough to say:

No matter how good you have it, stress never goes away, it just changes form.

I'm 33. I’ve built multiple companies. Don’t think about things like rent, food, or life expenses. Have a beautiful wife, an amazing family and great friends. Essentially ever metric I cared about at 22, I've reached. The version of me carrying $200K in student loan debt in my Bushwick apartment would call my current life a vacation. The truth is, he would be 100% wrong. The problems are different now. They're not less real. They're just different.

It's not the stress of "can I pay rent." It's the stress of a thousand Founders Club members trusting us with their time and their money. It's the stress of leading a team. It's the stress of starting to think about kids and what kind of father I want to be, especially knowing I had mine for only 18 years. The stress of investing every dollar I make wisely and making sure that I dont wipe out years of savings with 1-2 stupid mistakes.

And underneath all of it, the one I think about most:

I just want to retire my mom and spend more time with my family.

She worked for decades in jobs that didn't pay her what she was worth. She’s prioritized everything but herself as she raised two boys mostly alone. She never asks for anything and appreciates every thing we can give. The gap, between where I am and where I need to be to take care of the woman who took care of me, is the engine that fueled the majority of everything I do. On top of that I want to do the same for Lyndsey as I help make her dreams come true and desperately want to find as much free time as possible to see my eight month old nephew, McCoy, who is a bundle of joy.

Everything I described is just a different season of life. A difference stress. It's not lighter. It's just different.

When I was broke, I thought money was the cure. When I was in debt, I thought clearing it was the cure. When I was running CROSSNET, I thought an exit was the cure. Each time I hit the thing I was chasing, the thing did what it was supposed to do. And then a new thing showed up.

The reward for solving the problem you have is unlocking the next problem you didn't know you were going to have.

That's the part nobody tells you and everyone on that boat has realized the same thing.

I've been turning this over since I got back, and I keep landing on the same uncomfortable place.

There's no income number that turns the stress off. There's no exit that closes the chapter. There's no investment, no boat, no penthouse, no zip code that delivers the version of peace we were sold. Your favorite entrepreneurs and the people whose lives you scroll through and feel small next to are all, at the core of it, just humans dealing with their own version of the same thing. The variables change. The weight stays.

I'm not romanticizing being broke. I’ve been there for the majority of my life. Being broke is brutal, and I will fight every day to make sure my future kids never know what that feels like. Money matters. Going from recycling cans to financial security was the best thing that ever happened to me. But somewhere in my head I held onto the idea that there was a final boss, and once I beat him, the game would end. The boat showed me there is no final boss. Every level just has a different one.

What I'm starting to suspect, and I'm saying this out loud for the first time, is that the only thing that actually moves the needle is the ratio.

We get 16 to 18 waking hours a day. The question isn't whether you can build a life with no stress in it. You can't. The question is what percentage of those hours you spend on things you actually love versus things you dread.

I love writing this newsletter. I love Netflix in bed with Lyndsey. Traveling the world for concerts with my brother. I love sauna sessions and deep talks with Aaron. I love the gym at 7:30AM. I love our monthly retreats with Founders Club members.

This past month, BODY Hot Pilates had its largest month in company history. Six-figure revenue, six-figure profit, in a single month. We just got the keys to our newest studio in Sarasota, a location we were genuinely nervous about opening. The social response since we announced has been wild. The studio we were most worried about has become the one we're most excited about. Lyndsey is in the middle of building the thing she's dreamed about her whole life, and she's doing it with a specific quiet ferocity that I don't think I'll ever fully be able to describe.

There's a thing she does where she lays in bed at night, exhausted in a way only someone running their own brick-and-mortar can be exhausted, and she smiles. It's the smile of someone who is tired in the right way. Someone living inside a dream they used to only talk about.

That smile is the closest thing I have found to an answer.

It's not the boat. It's not the number. It's not the exit. It's becoming a person who is living their dream and balancing life to make the ratio of loved hours versus dreaded hours bend in the right direction over time.

The next month is filled with all out travel. I’m heading to Mexico City next week for a Founders Club member who has turned into a really good friend’s wedding! From there I’m on a two week Euro trip to Lisbon, Barcelona, Ibiza, and Sicily for my college roommate and the best lawyer I know’s wedding. Its amazing to see how friendships and relationships can evolve over time, as I now have access to one of the country’s best lawyers after a 15+ year friendship. If you ever need a recommendation, hit reply and I'll make the intro

Quick favor while I have you. None of the hotels are booked yet. If you have a favorite spots to stay or a place I absolutely need to visit in Mexico City, Lisbon, Barcelona, Ibiza, or Sicily, hit reply and tell me.

I'm also starting to write my first book. Working title: I Wish I Knew. The premise is simple. I'm going to interview 100+ Founders Club members, people responsible for billions of dollars in collective revenue, and ask them one question.

What do you wish you knew earlier?

I'll let you know what I find.

Chat soon,

Chris

PS. Reply directly to this email if you have questions or thoughts. I read every one.