All of these entrepreneurs built more of a lifestyle business or had a smaller liquidity event before they built a rocke

I think VCs may underestimate the extent to which mainstream entrepreneurship is a key input to outliers and moonshots. So many successful billionaire founders had a “never worry about rent again” moment via an exit in a much more boring business before swinging for a home run.

Austin Allred — co-authored the growth hacking textbook Secret Sauce, which became a best-seller and provided him the personal seed money to build Lambda School, valued over $150m.

VC’s may shit on lifestyle businesses but at the end of the day, they collect a 2% yearly management fee regardless of their success and typically have a great lifestyle (once their fund size is above $100m AUM).

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ore you ask the tough questions. This includes questions on family relationships, what their friendship groups are like. You should even ask questions that help clarify where your potential partner is at on things like family, feelings, and conflict resolution.

A lot of people go out and start their first business and try to make it a venture-backed startup. That’s the wrong move. That’s like going to the gym and trying to bench 250 lbs on day one. It’s not that you can’t build up to that, it’s just not the right move today.

Most entrepreneurs start with one goal in mind: freedom. If you value freedom, you should have one goal for your first company, and that’s to build a lifestyle business that can produce $100k /yr of personal income. It can be boring and it doesn’t have to scale. It sets yourself up for the foreseeable future and then you can afford to take big swings. Forget startups. Forget venture capital. Build something that gets you in the game and makes you a living first.‍

The point of entrepreneurship is freedom. Yes, it’s to build cool stuff and innovate and all that, but at the end of the day the sort of person who becomes an entrepreneur is usually doing it because they want the freedom to control their day and work on the things they care about.

Alex Tew — started the Million Dollar Homepage to raise money for his university education. He sold 1 million pixels on a 1000 x 1000 pixel grid on his website for $1 per pixel. He ended up making $1,037,100 USD before founding the billion-dollar meditation app, Calm.

My definition of rich is having a passive income that’s greater than your burn. I’m pretty sure we can all comfortably live off $40k/mo without ever having to leave the house.

After 20 years, you can choose to sell that business or automate it and let it ride but with $9.6m invested in a conservative portfolio paying out 5% annually = $480k/year in interest or $40k/mo for you to live off without ever touching the principal nor sacrificing your quality of life.

Daniel Ek — Spotify isn’t Ek’s first success. Daniel Ek became a self-made millionaire at age 23, before even putting a single thought into Spotify. At 23, Daniel Ek “retired” after he sold his online marketing company Advertigo to Swedish digital marketing firm TradeDoubler in a deal worth $1.25 million.

Elon Musk — before sending rockets into space and revolutionizing the auto industry, Elon Musk was broke building Zip2 (online city guides for newspapers) before he netted $22m on the sale. Source

Patrick