Raising money fucked me up

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 that worry. It’s hard to replace it if you consider it your motor. Let the desire to do well and good stay, but let the fear of others disappointment go, and the fantasy that we can control those outcomes by squeezing every last drop out of ourselves.

> 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.

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?

Without trying to be glib about it, this post sounds like a description of second-system syndrome, applied to entrepreneurship. It happens to all of us.

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.

Loved it, understanding and working through your vulnerabilities is super hard but ultra rewarding. Bold but very altruistic move to publish this

This is exactly why I've avoided raising so far. Not because VC money is bad - obviously it enables things that wouldn't otherwise be possible - but because I know myself well enough to recognise I'd react exactly like this.

The author nails it: "I started to actually operate in a way that is counterproductive for my startup, while thinking I was actually doing what was best." That's the dangerous part. The pressure doesn't announce itself as pressure. It masquerades as ambition, urgency, drive.

Bootstrapping has its own version of this though. Instead of investor expectations, you've got the slow burn of "am I wasting years of my life on something that needs capital to work?" The grass is always greener. At least with VC money, you can move fast and find out if you're wrong. With bootstrapping, you can spend 3 years proving out something that would have taken 6 months with proper funding.

Neither path is inherently better. But knowing which one will fuck with your head less is worth figuring out before you're in the middle of it.

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.

Finding the right psychologist/coach/founder to chat this over with will probably do you and the company wonders.

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 comes Z%

You can make the best decision and have a bad outcome because there are so many unknowns. This isn't chess

You can play everything wrong and still hit it out of the park

I mean this is one of the range of outcomes that could've happened. You can't declare yourself a success or failure from one project

Just keep making good decisions and don't risk it all, and you'll more than likely end up fine

Imagine betting on someone and xe writes this ...