I lost ten million dollars doing something stupid.

Hello friend,

Here's what I'm thinking about…

I just went on My First Million for the 20th time (kind of crazy).

We talked about:

• The world's best and worst business models
• Why you should want to be hated
• My response to the trolls
• Super Genius vs. ADHD Type Entrepreneurs

It's a fun one. Listen here: YouTube / Spotify / Apple Podcasts

"Lina is REALLY good at making friends."

Zoe's sister Ariele and her friend Lina were visiting the other weekend when Ariele casually dropped this compliment.

I immediately leaned in and wanted to know more.

If I have one passion in life—maybe even an addiction—it's making new friends.

Most people want money. A nice car. A flashy watch. A beautiful house. Why? Because they think if they get those things, it will somehow translate into the life they dream of — a life where they have a great partner, interesting friends, and a community that welcomes them.

They crave connection—they just try to get it in the wrong way…

Read the full essay →

I've had this song on repeat for days now.

'Rich Men North of Richmond' by Oliver Anthony (Spotify).

If you haven't heard it, you should listen. I get tingles up my neck every time I listen.

If you study history, there's this recurring pattern—what Robert Greene would call the cycle of generations...

Read the full essay →

My last newsletter was about screwing up.

This is the story of one of my most spectacular ones.

This week, with quivering, shell-shocked hands, I signed documents that hammered nails into the coffin of my greatest business disaster of all time.

We finally shut down Flow, the productivity software company I started back in 2010. Twelve years and over $10 million of my own money, lit on fire trying to compete with a Facebook billionaire's VC-funded juggernaut. The full slow-motion train wreck—and the six lessons I bought at full price…

Read the full essay →

Random Stuff:

• I'm hosting a very odd conference in Maui. One for lonely weirdos like me who run holding companies with many (sometimes dozens of) businesses. I looked it up, and the term for people like us is "Conglomerateur." If you ever want to get punched in the face, introduce yourself as one! We have some incredible speakers and attendees (Ben Gilbert from Acquired, and Tren Griffin from Microsoft, to name a few) and it's shaping up to be a great event. If you run a holding company doing $25M+ across a variety of businesses, you should apply.

• If Apple made an electric razor, it would look like this. I just got a Laifen P3 Pro and I'm absolutely blown away by the design and build quality. China is really upping its game.

• I got one of these little e-ink displays for our kitchen and I love it. It's called TRMNL and I have it show countdowns to birthdays, holidays, and vacations, plus our family calendar. It's really well crafted and totally extensible. On the one in my kitchen, I just added a countdown clock of how many days ChatGPT estimates I have before I die (17,451 days). Fun customization!

• I'm obsessed with this paired down version of 'Strawberry Fields Forever' from The Beatles Anthology. So good.

That's all for now…

-Andrew