Being a Founder can suck

Being a human can suck too, of course, so I get it if you’re already rolling your eyes at how cliché that sounds. We grow up on lines like “Life isn’t fair,” designed to teach us that being human can and often will be painful.

But being a founder is its own kind of strange. You know life is hard in general, yet before you became a founder, all you ever saw was how great it looked from the outside. The media is packed with highlight reels and victory laps. By design, it only tells the “newsworthy” stories.

You don’t see the founder who was quietly building a solid business until a divorce blew up their life, derailed the company, and vaporized their investors’ money.

That “non‑newsworthy” story is everywhere. You just don’t hear it until you’re one of us.

If you’re like me (a founder for over a decade, writing a newsletter for founders, spending almost all of your time with founders) you’re surrounded by those stories. The Divorce. The Tragic Loss. The Scary Diagnosis. The Stress‑Borne Insomnia. Anxiety. Pain. Sadness. Loneliness.

If only we weren’t predisposed to try to carry all of this alone.

Your Pre-Selective Proclivities May Be Hurting You

Founders are not a random sample of humans.

Most people never seriously consider starting a company. The ones who do tend to share a specific cluster of traits. We like to call them things like grit, resilience, appetite for risk, bias toward action, resourcefulness.

They show up nicely in a pitch deck. They also _{come with fine print.}

To become a founder in the first place, you have to be the kind of person who runs toward hard problems instead of away from them. You have to be comfortable betting your time, reputation, savings, and sanity on something that might not work. You have to be stubborn enough to keep going long after a reasonable person would have tapped out.

And then we drop that personality type into an environment that constantly reinforces the story: you are the one who fixes things.

From day one, you are rewarded for “figuring it out.” Investors back you because you seem unflappable. Early employees join because you project certainty. Customers buy because you make them feel like everything is under control. The entire system is set up to applaud you for absorbing stress so other people don’t have to feel it.

So when the cost of that stress starts to show up in your sleep, your mood, your marriage, your body, etc, your default move is the same as it’s always been:

Work the problem.

Tighten the calendar. Tweak the stack. Change the diet. Add a supplement. Read another book. Optimize, optimize, optimize.

What you don’t do, almost by design, is raise your hand and say, “I’m not okay and I need help.”

Compared to non-founders, we have more identity wrapped up in being the person who can handle it. Asking for help feels less like “being responsible about my health” and more like “admitting I’m not cut out for this.”

The irony is brutal: the exact traits that make you a good founder (the willingness to take on outsized responsibility, the belief that you can solve anything, the comfort with risk and sacrifice) are the same traits that make you more likely to suffer in silence, minimize your own pain, and treat real mental health issues like just another bug you can patch on your own.

In other words, you weren’t just dropped into a hard job. You were pre-selected to be unusually bad at stepping out of it to get help.

Consider a Mental Wellness Pivot

We’re all out here working so hard for some great accomplishment. We hope to achieve fabulous wealth or make some other impact. What a shame it would be if we worked so hard to numb our pain along the way that we end up numbing our joy, should we find success.

James Oliver Jr Doesn’t Want to See That Happen

I mentioned last week that I was starting a podcast. Not to pursue sponsorship from BlueChew or DraftKings, but to have open conversations with interesting people who have great perspective on what I write about in this newsletter.

I had to start with James Oliver Jr because he literally wrote the book on founder mental health.

This book tells some amazing and sobering stories about Founder mental health and it drove home for me that:

1. You’re not alone

2. It could get a lot worse

3. You don’t have to wait for the worst case scenario to start taking care of yourself.

Watch our conversation

I present to you my first podcast episode. I didn’t use the modern tools that make it sound like a professionally edited interview segment. It’s a conversation and it sounds like one.

James’ story is awesome and his book was incredibly eye opening. I’ll be recommending this one for a long time.

Accept this gift of mental wellness

James has generously offered to gift three of you wonderful founders 4 free virtual mental health sessions on the BetterHelp platform.

No strings. Just be one of the first THREE founders to FILL OUT THIS TYPEFORM and you’re in. It is anonymous so I won’t know who is signing up for this.

Next best thing?

Ok if you aren’t ready for therapy (or you didn’t get here in time to snag a free slot), James is also hooking anyone who wants it up with their first 3 months with the Calm App for free. Don’t wait because this expires in a few days. If you don’t already use the Calm App, fill out this typeform and enjoy your first 3 months for free ❤️ 

Thank you, James!

Request for Podcast Feedback:

If you watched my first podcast episode and thought “Oh boy, he has a lot of work to do” then please take a second to tell me! Improvement is so much faster with the real feedback founders crave.

Do you want to be on my podcast?

I’m only filming one per week and I’m well on my way to filling my entire year so please let me know ASAP if you’d like to share your life with us in an open conversation about being a Founder. Just hit reply 🙂 

THE END

I love you