The Pain of the Artist Entrepreneur


February 5, 2024
3 min

Back in May 2023, I decided to wind down my dream startup.

It was a decision which I felt kind of was forced onto me.

I say forced because we had just figured out the exact direction we needed to take and started getting traction (revenue, etc.) but a few things cornered me into ultimately deciding to stop.

  • We bootstrapped so funds were low and we had bills.
  • I spent my savings over 3 years (avoiding rent by using my mom's basement, moving to Argentina, etc.)
  • I hadn’t stopped working 12-hour days in 3 years.
  • CTO quit (startups are very hard we know).

Overall, between the mental capacity I had left and the cash and technical backup I didn’t, I felt it was time to wind down.

It was not easy. Here are some thoughts that go through the mind of a competitive person who comes from an athlete and military background:

  • You’re giving up.
  • Keep going.
  • Would Elon do the same?
  • Every great person you look up to goes through this.
  • It’s okay, this is a stepping stone.
  • Go into more debt.
  • Is this fair to those that believe in you? It’s almost offensive to them.
  • You learned a lot. Now people should take you very seriously and offer you a lot of money to work for them so at least you will get a more comfortable paycheck while you cool off.
  • As the CEO, it is my fault insert the whole entire list of things that went wrong.

Along with 13,000 other things a million miles a minute.

You can probably guess that this mentality is what most people go through.

But what very few cannot understand (and what I did not expect to happen) are the long aftereffects at times:

  • The loss of sleep.
  • The mornings when you feel you have no direction and do not want to get up.
  • The pep talks to force yourself out of bed.
  • No HR person understanding your CV.
  • No HR person wanting to deal with a founder.
  • No one putting respect on your name enough to not waste your time in interviews and very inappropriate and exaggerated processes.
  • Very few understanding the deep value you bring to the table to be able to understand C-level people’s mindset and take pressure off their plate due to knowing how to run things well and be a business-minded person.
  • Recruiters saying they want you and ghosting.
  • The adjustment of it all.
  • Trying to adapt as fast as you can without making it obvious you see exactly what is going on behind the scenes.
  • The mental toughness of pushing through it all with positive thoughts + “this is what they all went through. Keep going. It’s part of the story.”
  • Keeping yourself busy by building new systems, testing new AI tools, building small apps.
  • The internal struggle of ego when someone wastes your time, energy, and trying to remind yourself that this is how the real world is.
  • No one caring who you are or what you have done because you did not exit or make a ton of money.
  • Questioning yourself constantly.
  • Being skeptical against VCs and the system.
  • Having to adjust when people move slow and you move fast.
  • Reminding yourself not to ask too many questions in interviews because you could come off as a person who is “asking too many questions.”
  • Asking yourself why you should work under someone who is not 10x better than you, (while still understanding that you can learn something from everyone but wanting to always be around people that you who have done what you want to do).
  • All of a sudden being swept into a war along with your closest friends and family (Israeli founders).
  • Watching your nation see death and pogroms before its eyes (Israeli founders).
  • Being worried to open the door because terrorists run loose (Israeli founders).
  • Seeing the world turn on you with so much factless, biased, unfathomable hate (Israeli founders).

The list goes on and on.

So what do you do when every single thing is sitting on you?

When you just had it all sitting on you and even post-company you still have weight?

When everything is crashing down?

When you don’t see a light?

Remind yourself of why you came.

Remind yourself that this is a stepping stone.

Get up. Keep going.

Lie to yourself and lie again and again and again to stay positive.

Look at images like this to remind yourself that it is a long, hard journey.

[Embed tweet]

Remind yourself of the athlete days when you wanted to give up but kept going and soon after you won.

Remind yourself of the sleepless nights of the army when everything in your body felt broken and cold, and you wanted to throw all your gear on the floor, but shut up and kept going and by the end of the week you sat back and felt confident in yourself that you finished it.

Remind yourself that in both of those situations - there was no other choice but to keep going because giving up in the middle would have resulted in literally nothing.

Left on the sidelines while watching other people win.

Left in a field in the middle of nowhere with no way home and letting your teammates down.

And worst of all - left with a feeling that you didn’t do it, and you aren’t proud of yourself (regret).

And so yes, this might be another cheesy article to tell you to keep going.

That the only way out is through.

That is because there is no easy way.

There is no magical formula besides fail and learn and repeat 10 times and then win 1 time.

THIS is the way.

I leave you with this: The artist sometimes lies awake at night wanting and enjoying the struggle, because sometimes the best pieces of art come out of pain.

Ash Fishman

Building in the Web3 music creator economy, while entrepreneur-ing like an athlete. Hunger on the Hillside. ⛹🏼‍♂️🏄🏼‍♂️🏋🏼‍♂️

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