The 5 levels every founder faces (in order):

Level 1: Not enough leads

Level 2: No killer product

Level 3: Too many leads (systems breaking)

Level 4: Your team needs to level up

Level 5: You need to level up

You can't fight the next boss...

I sold The Hustle's first ads. About $100k worth.

Here's the 1st cold email I sent that got a sale. It was Wealthfront.

Maybe sent emails to 20 diff brands, 5-8 showed interest.

We had 93,535 subscribers. I charged them $26 per 1,000...

I sold my company for over $40 million when I was 31.

Here’s every idea I tried before my big win:

1. In high school I made $2,500 one summer flipping seniors’ used sports gear on eBay.

2. At 20, I launched a hot dog stand called Southern Sam’s: Wieners as Big as a Baby’s Arm. Made up to $1,000 a day. Learned how to sell - and how to blow all my money on beer.

3. That same year, I started an online liquor store selling rare whiskey. It lasted three months before a lawyer told me I wasn't doing things correctly. Still made $10K in profit.

4. In San Francisco, I started a weekly business book club called The Anti-MBA. Couldn't figure out how to monetize it, but met lifelong friends.

...

Hampton has a Slack channel called sh*t i'm f*cked where people tell stories when they nearly failed.

The channel is our most popular channel.

Its honestly pretty awesome seeing super successful people talk about near-business-death experiences.

Also fun to celebrate these f*ck ups and laugh at it all.

A few highlights (anonymized):

1. $140k payroll due in 6 days. $550k in receivables. $7k in the bank.

...

A major difference between founder & employee mindset is orientation to problems.

Employee mindset believes problems are bumper-to-bumper traffic. Out of your control & no way through until someone else fixes the problem.

Founder...

Let me tell you about the creator tension.

On Youtube, My First Million episodes mostly get ~60k-300k views per pod lately.

Spotify + iTunes, consistently in the 100k range (haven't looked in forever, but whatever it is, its consistent).

This week Robert Greene was on.

I LOVED recording it. I learned so much. I wanted to go for another 2 hours. He moved me.

But on YouTube, its maybe the worst performing pod in the last 1-3 months.

...