The most active angel investors I know bootstrapped and sold their SaaS businesses

Most of the big angel investors I know have one thing in common:

They bootstrapped and sold their own software businesses.

Isn’t that ironic?

The entrepreneurs who never took any outside investment are the most active angel investors in my network.

I do know plenty of folks that grew VC-funded companies who invest too. That’s the game I played, so I get it.

But between the coasts and outside of a few tech hotspot cities, I see that former bootstrappers are the most active angels.

  • Maybe there are more of them who ended up with a lot more extra money to invest.
  • Maybe they love the entrepreneurship game so much they want to keep playing by helping the next generation with their time and treasure.
  • Maybe they know how brutally hard it was for them and they want to make it a little easier for someone else.
  • Maybe they believe more in the ability to grow something from nothing to build a great business and a great life.
  • Maybe they know there are plenty of great founders doing things differently who get overlooked by venture capital investors.

This adds up to a bunch of savvy entrepreneur-investors helping an important segment of crazy founders.

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