Imagine: You’re 25 years old, sitting in your childhood bedroom while your mom thinks about dinner in the next room. Suddenly, your phone buzzes with a bank notification—a life-changing amount of money just hit your account. You’ve officially sold your company for millions, and it feels… completely anticlimactic.
That was my reality when Morning Brew sold, and it’s one of the stories I shared with Sam Parr and Shaan Puri on the My First Million podcast. But the real story isn’t about that moment—it’s about the wild journey that got me there, from crashing college lectures with printed spreadsheets to building a media empire one email at a time.
Podcast Clip
You can watch the 22-minute clip from our conversation right here, where we dive into some of these stories.
The “1 to 100” Operator Mindset
Sam called out my “private equity-like ability” to analyze businesses and know which levers to pull for growth. He’s right—that’s where I thrive.
While creators like Sam and Shaan excel at the “0 to 1” phase of starting something new, I’m a “1 to 100” guy. I love taking that initial spark and building a durable, profitable machine around it.
This mindset came from my undergraduate business degree, where I took every accounting class possible, and was solidified during my investment banking summers. Learning to live inside a P&L gave me the conviction that focusing on key metrics made success almost mathematically certain.
First 50,000 Subscribers
Before we had marketing money, we had to get creative. Our strategy was simple but effective: crash college lectures.
We’d walk into massive Econ 101 or Psych 101 classes at the University of Michigan, give a 60-second Morning Brew pitch, then literally walk the aisles with a printed spreadsheet getting students to write down their email addresses. We wouldn’t let them leave until they did!
It was pure, unscalable hustle. But we replicated it at universities nationwide—Penn State, Miami, NYU—until we hit 50,000 subscribers. We were notoriously frugal, making new hires bring their own laptops and packing sticker envelopes ourselves on Friday afternoons. This intense focus and grit built our foundation.
Anti-Climactic Exit Moment
People imagine selling a company involves popping champagne on a yacht. For me, it was the complete opposite.
The deal closed during peak COVID. I was 25, living in my childhood bedroom at my parents’ house. When the life-altering wire transfer hit my account, I was sitting at my desk while my parents were in the next room and my mom was probably thinking about dinner. It was the most surreal and anti-climactic moment imaginable.
This taught me that external milestones are rarely as fulfilling as the daily process of building. The real joy was in the trenches, not the finish line.
My Philosophy
After the exit, I hired a financial team and put 90% of the money into conservative investments—Vanguard funds, bonds, and real estate.
For the rest, I adopted Ramit Sethi’s “Rich Life” philosophy: spend extravagantly on things you absolutely love, cut costs mercilessly on things you don’t.
- Things I’ll spend on: Travel, business-class flights, and really nice hotels. Those experiences are priceless to me.
- Things I won’t spend on: Flashy cars. I live in New York City—buying a Lamborghini to sit in a parking garage 360 days a year is terrible money management. I bought a brand new Acura and love it.
This approach helps avoid lifestyle creep while enjoying the freedom financial success provides.
Conclusion
Looking back, our success wasn’t about a single stroke of genius.
It was about relentless focus, understanding our numbers, and having the grit to do unglamorous work every single day.
Full Podcast Episode
The conversation covered so much more than what’s in the clip.
If you want to dive into the full hour-long episode and hear more stories about our investors, my trip to Kid Rock’s ranch, and building company culture, you can watch it below, or on YouTube by clicking here.