The other day I wrote about how desperate I was to take a pause from the breakneck speed of jumping from start-up to start-up to start-up for the last 4 years.
The sentiment is true, I stand by it— not having savings, because I spent them all on my business, has really limited my options in life. I’ve written extensively about how you must pay yourself, and your business must produce enough revenue to support you after a reasonable period of time for this very reason: you need to be able to give yourself a break and some optionality when you need it most, at the end of your time running your business.
Most founders bet on a liquidation event or some sort of flashy end to the story, a white knight delusion that there will be some massive rescue should you just work hard enough. This doesn’t happen for most of us. (This is also why I’m a big fan of secondary/taking money off the table if you’re a founder who has raised venture capital— take what you can, take care of yourself, your investors won’t do that for you.)
I have also written quite loudly about the mistakes I’ve made— more on that below, after the jump. I’ve written about how you shouldn’t start a business. I’ve talked a lot of people out of big swings that I thought were irresponsible and ill-fated. I’ve answered AMA questions that have possibly discouraged founders.
It’d be fair for you to extrapolate from what you’ve read here that I’m anti-risk, though my resume suggests a fairly insane risk tolerance. I’m not sure I know anyone else with as high a risk tolerance when it comes to their career— I roll the dice on ideas I have, pre-”product market fit” start-ups, working with people or in a business entity/structure that I know absolutely nothing about over and over and over again. This can oftentimes make me hate myself.
Why am I attracted to jobs that make my hair fall out? Why is the idea of a safe, stable job for myself somehow so repulsive and repugnant to me?
But then again:
I came across this Sartre quote on the Substack app the other day.
In my lowest, darkest, ickiest moments, when I’ve felt the shittiest about myself or my accomplishments or my credit card debt or the landslide of bad luck, rejection, and depression that nearly buried me since 2020, I have one, tiny comforting thought. It’s a chip on my shoulder, one small thing that allows me to feel superior, in some way, at least, to my peers who were all out-earning me, crushing life, getting married and getting jacked while I was flailing.