[hkarthik]

From a timeline perspective, let's see how the rule of 3 startups would work out to become King.

Ages 22-25: Fresh out of college, work for a startup as an employee and learn the ropes, build connections, and level up with the right skills.

Ages 25-30: Strike out on your own with Startup #1. Work at it for 5 years (because the VCs totally own you) and then bail.

Age 30-33: Start another startup with VC funds, but negotiate better terms. Work at it for 3 years to get the 7 figure exit.

Age 33+: A full 13 years after you began your career, you're finally ready to bootstrap a business with no VC at all. Maybe now you can actually slow down enough to get married, have a family, and put down some roots. Well hmm, now with all those responsibilities on the line, it seems foolhardy to risk your own cash from the previous ventures when VCs are willing to give you money again...

[ChuckMcM]

There is another path, marry an engineer and delay starting your family for a few years. It worked out pretty well for me. While she was working we always tried to balance risk between the two jobs so that either one of us having our job go poof would still have enough runway to recover.

I certainly agree doing it all yourself is going to be a challenge.

[michaelochurch]

What's sad is that, as bad and wasteful as that trajectory sounds, it's the 99.9th percentile outcome.