Ask HN: What has been your single best investment?

Re:Ask HN: What has been your single best investment? by smt88 on Tuesday March 29, 2022 @02:04AM (#30839329)

$15k => 30% stake in bootstrapped $100M company

Sounds good, right? You see these all the time.

But the truth is this is one successful startup after 10-15 attempts, each of which cost me either cash or market-rate salary.

So if you factor in the opportunity cost, it's a lot more like:

$800k => 30% stake in bootstrapped $100M company

Still very good, but easily could have happened 10 years from now or not at all. Bootstrapping is definitely gambling.

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Re:Ask HN: What has been your single best investment? by mwint on Tuesday March 29, 2022 @07:32AM (#30841215)

How’d you get started / get in a position to both have all these opportunities, and be able to take them?

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Re:Ask HN: What has been your single best investment? by smt88 on Tuesday March 29, 2022 @12:16PM (#30844517)

I was born lucky (high-income parents who encouraged me to learn coding and had money for computers) and have financed most of my bootstrapping with sweat equity.

For example, I've done some joint ventures with business people who were willing to give me 50% of market rate but then a big chunk of equity. I have never worked for $0 and no one should ever do that.

Eventually I became sought after enough that I can make market rate and still get equity.

Startups are like lottery tickets, and if you aren't just born rich, you have to find a way to get more lottery without going bankrupt or ruining your quality of life.

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