Greg Isenberg is a multi-exit Silicon Valley entrepreneur and owner of Late Checkout product studio. He has:
- Headed Product Strategy at WeWork
- Been an advisor to Reddit
- Founded a startup, Islands, which was sold to WeWork
- Founded 5by, which was sold to StumbleUpon
Guest Author: Greg Isenberg
When you raise venture and you’re the CEO, you’re still making $100k+ no-matter what. Realistically more. You know how long you’ll be getting that cash for even if VCs decide not to fund you anymore (usually 12-18months).
You’ve got baseline stress because you want to build something big.
When you are bootstrapping and you are profitable, it’s way less stress than running a venture-backed startup. You’ll taste real freedom and probably take home $500K+/year through dividends.
![](https://techzi.co/wp-content/uploads/2024/07/image-112.png)
When you are bootstrapping and unprofitable, it’s way more stressful. Everything is on your shoulders. You’re looking at creative financing like lines of credit and growth hacks to get you to profitability like your life depends on it.
Your stress levels go down the more profits you make.
I’ve got tons respect for both type of founders, but bootstrappers you earn an extra tip of my hat.
![](https://techzi.co/wp-content/uploads/2024/07/image-113.png)
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