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Raising money fucked me up

blog.yakkomajuri.com

21–30 of 147 posts

Re: Raising money fucked me up

#21
post #5

I think everyone would seriously benefit from learning poker. I used to play professionally and the idea of looking at things as probabilistic bets, and in terms of expected value is so deeply rooted in my mind Investments are bets. Most sane investors aren't putting it all on one thing Startups are bets Applying for jobs. Sales. Dating. Health. Basically everything You risk $X money and time for a payoff of $Y that…

> You risk $X money and time for a payoff of $Y that comes Z% Unlike in poker where you know those 3 numbers if you are paying attention, in real life you know only X, and sometimes not even that. The rest is a guessing game, and that estimation is the hard part.

In poker you learn to strategically size $X based on your estimates of $Y, Z%, and current bankroll.

Even if your estimates have large error bars, it can still be a good bet if you believe it’s +EV and have a large enough bankroll.

Re: Raising money fucked me up

#22
I have a few 1099 MBA advisors that I call Chief of Staff. I check my questions against what they think. When you get 3 MBAs with engineering, finance, or CS degrees agreeing independently, it bumps up confidence.

I think this is a case where this helps considerably. Its essentially the 'consulting' thing for small businesses.

Re: Raising money fucked me up

#23
post #5

I think everyone would seriously benefit from learning poker. I used to play professionally and the idea of looking at things as probabilistic bets, and in terms of expected value is so deeply rooted in my mind Investments are bets. Most sane investors aren't putting it all on one thing Startups are bets Applying for jobs. Sales. Dating. Health. Basically everything You risk $X money and time for a payoff of $Y that…

If you want me to ruin this for you, look up Bertrand's Paradox and The Problem Of Priors.

I recently had to deal with this, ugh, I just pick a prior or two and see what the outcome looks like. I'm not sure we can calculate probability of success, but rather use probability to find losing ideas that should never be done.

Re: Raising money fucked me up

#24
post #5

I think everyone would seriously benefit from learning poker. I used to play professionally and the idea of looking at things as probabilistic bets, and in terms of expected value is so deeply rooted in my mind Investments are bets. Most sane investors aren't putting it all on one thing Startups are bets Applying for jobs. Sales. Dating. Health. Basically everything You risk $X money and time for a payoff of $Y that…

I read about mathematical expectation in a poker book for the first time a long time ago and it's really an interesting way to think about the world. In real life, it's a bit different though since there are other factors than just raw percentages like poker hands. For example, you could do everything right and still fail while someone else (like a nepo hire) can do everything wrong and still succeed. Life's odds are…

I think the metaphor is pretty extensible to handle the things you point out.

> you could do everything right and still fail

Sometimes even a high probability draw doesn't get there on the river.

> while someone else (like a nepo hire) can do everything wrong and still succeed

Some people always start with pairs, Axs, or suited connectors.

Re: Raising money fucked me up

#26
> Then you look around and see "startup X gets to $1M ARR a month after launch" and shit like that and I'm feeling terrible about how we're barely growing.

Comparison is the thief of joy. I fall into this trap almost weekly. Success stories are incredibly rare and we only see the splash, not the iceberg of failure just beneath the surface.

I think about my current business constantly even though on paper we are making enough to keep this thing going forever but it never feels enough.

I felt this post and appreciate the honesty.

Re: Raising money fucked me up

#27
post #9
post #7

Expectations that we hold inside of ourselves can be a really difficult echo of identities we tried fantasizing about when growing up and as an adult. We want to do well, we want the approval, we want the validation. The anxiety over expectations can kill you. It’s self abuse - people (investors, bosses, spouses) don’t invest in you for your anxiety driven productivity, they do it because of who you are outside of th…

Can you separate "who you are" from that worry? Seems to me it's a part of you and you wouldn't be you without it, for better and worse.

It's always important to remind one's self that "who you are" is simply the story one is attached to. Things like meditation or psilocybin can help bring that to light.

Re: Raising money fucked me up

#28

[flagged]

With boot strapping at least you can de risk with consulting/freelancing. And I think with the new generation of software development tools it’s much easier to validate the core business problems without grinding out code for weeks on end.
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