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Raising money fucked me up

blog.yakkomajuri.com

11–20 of 147 posts

Re: Raising money fucked me up

#11
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…

A wonderful and personally relevant thing to read.

Re: Raising money fucked me up

#14
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 rigged.

Re: Raising money fucked me up

#16

Imagine betting on someone and xe writes this ...

Nothing about this struck me as a sign that money wasn’t well-invested. From the headline, I was picturing “we raised and then I blew it in Vegas”.

Nothing wrong with admitting to uncertainty and insecurity. I mean, there are two types of people — those who suffer doubt sometimes, and those who don’t admit it. Give me the first kind any time.

Re: Raising money fucked me up

#17
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.

Identities shift over time whether we intend it or not. Who you were at 5, or 10 is not who you are at 20, 30, 40. We all pick up baggage, trinkets, burdens, and experiences.

One worries because it was a helpful strategy compared to not worrying, but some (like me very specifically) can get attached to that worry to the detriment of picking up other mechanisms.

Re: Raising money fucked me up

#18
When doing my own startup in the past, the biggest pain were: loneliness and inexplicable paranoia. Which then lead to anxiety.

This, when unchecked, can lead to self inflicted, unnecessary pressure on myself. And failure to meet the impossible deadlines, created downward spiral.

I think this is normal, everyone went through the same thing. That’s why some VCs filter for megalomaniacs, zealots, or people who have no idea what pain is, because the journey is insane arduous.

The pain magnifies if the startup is located in VHCOL. Every month a whale appears and eat a big chunk of your runway. Who wouldn’t have anxiety?

Re: Raising money fucked me up

#19
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…

One of my favorite star trek scenes: https://www.youtube.com/watch?v=t4A-Ml8YHyM

Re: Raising money fucked me up

#20
Thank-you! It is great to read a honest and self-aware journal covering this.

As someone who fantasizes about running my own thing, working for a few start-ups have made me very stringent on what my requirements are for starting something (co-founders, investment, location, market). And also that these requirements have become so very risk-averse that I probably am not the personality profile to run a business! Nevermind the endless imposter syndrome.

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