The Pain Cave

Are you willing to step inside?

TLDR: Most founders are tourists. Are you really sure you want to do this?

I have so many conversations with people that start like this:

“I have a friend who has this great idea, they’re thinking about starting a company, would you be willing to talk to them by any chance?”

Every once in a while there’s an incredible introduction, but the truth is, 99% of these tend to be what I like to call Founder Tourists. People who like the idea and the so-called glamour of being a “successful founder.”

And to be clear, there are—for sure—infinitely better ways to build companies and to get rich than by being a venture-backed founder. If that’s your reason for building, you might just want to pack up and go home right now.

I can walk you through the dilution math and exit outcomes another time, but the harsh reality is, if you are a venture-backed founder, you’re not going to be Brian Chesky rich. You’re more than likely going to be Shmyan Shmesky poor.

Below is a post from Raviv Sapir; highlighting a top 1% outcome, an $85m exit.

Sure the upside may be unlimited, but the other 99% are worth ~$0.

Are You Willing to Go Into the Pain Cave?

Monday morning. The week begins. Before you dive into customer calls, another round of product iteration, investor updates, or hiring plans, let’s ask a real question: Are you actually willing to do this?

Not ‘do you think you want to start a company?’

Not ‘are you excited by the idea of being a founder?’

Not ‘do you like the idea of raising millions and making Forbes 30 Under 30?’

No. Are you willing to go into the pain cave?

Because that’s what this is. A place where every rational signal in your brain will tell you to stop. A place where your body, your relationships, and your bank account might all take a hit. A place where you’ll feel more alone than you ever have, even when you’re surrounded by people.

You’ll wake up at 3 AM and stare at the ceiling, wondering if your company will exist in a month. You’ll cycle through exhilaration and despair within hours, sometimes within minutes. You’ll be told ‘no’ so many times that ‘no’ stops even sounding like a word—just a dull sound in the background of your existence.

Are you ready to be broke longer than you thought? Are you prepared to fire your best friend? To let go of employees who moved across the country to work for you? To tell your significant other, once again, that ‘next month’ is when things will stabilize?

Are you prepared to see a competitor, who is worse than you, raise more money and hire better engineers? Are you willing to sell your car? To skip weddings and birthdays and holidays, not because you’re a bad person, but because you have no other choice?

Do you have the stomach to hear that your idea is stupid—repeatedly—and still march forward? Do you have the stamina to get crushed by rejection for two years before you see a sliver of momentum? Are you mentally stable enough to handle the daily rollercoaster of feeling like a genius in the morning and a complete fraud by dinner?

Because here’s the thing: You don’t get to skip this part. No one does. If you want to build something great, this is the price of admission. It’s not fair. It’s not glamorous. And no amount of positive thinking will save you from it.

This isn’t meant to scare you. This is meant to help you. If this doesn’t sound like something you want to endure, you should not do this. And that’s okay. Truly. There are other paths in life that are fulfilling, rewarding, and even lucrative. But founding a company isn’t one of them unless you are ready—really ready—to suffer for it.

If this resonates—if, despite all this, something in your gut still tells you to move forward—then you might just be one of the ones who can do it. But go in with eyes wide open. The pain cave is waiting.

Are you willing to step inside?

See you Monday.