Pain, anxiety, and overwhelm

Non-textbook approaches to founder stress

Hi all -

Here’s the deck I’ve been working on for a while. It’s my perspective of the path from $0-$1M ARR. If you’ve got a community you’d like me to share this with / speak at, or a startup I can help… reach out!

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You’re in it, so you already know: Building a startup is mentally brutal.

It’s unlike any other professional endeavor. Most of my readers have had successful careers in the high-stress worlds of consulting, corporate, etc. And yet - being a founder is different.

Three things that caused me stress unlike any other work experience:

1. The anxiety that I’m wasting my life. Especially true pre-Product-Market Fit, but continued on after. I stopped checking LinkedIn and intentionally lost touch with business school friends. Seeing other people moving forward with their lives and careers while I was LARPing as a wannabe founder was more than I could stand.

2. The fear that it’s all going to fall apart, and that I’m not good enough to hold everything together. Once you start to get a little traction, you know how flimsy your business is… and you’re paranoid that all your customers will churn and your team will give up.

3. The overwhelm when things start to work - that you’re missing SOMETHING important that’s going to kill your business, and you don’t have the time or energy to figure out what it is. There are always a million things to do, and you’re dropping balls left and right. Something’s going to break you.

You might think that it gets better once you get to $1M, $5M, or $10M ARR. It won’t.

It only gets more difficult, because there’s more riding on your success. The bar raises, especially if you take growth capital.

This mental stress can break you.

I’ve seen founders break. They lose total touch with reality, become paranoid and vengeful. I’ve heard stories & seen firsthand some wildly destructive behaviors. The stress can turn good people into tragic characters.

But this mental stress can also make you stronger.

While there’s a lot on mental health for founders, nothing has really resonated with my experience.

Because you have to work hard. Really hard. And you have to be creative, too. You can’t just go on a bunch of meditation retreats, do trust falls, and sing kumbaya to recharge. You’ll never be operating at 100% when you need to, and you’ll never be ready when shit blows up.

Here are three ways I tried to get stronger through the stress. They definitely aren’t “healthy”, but then again neither is being a founder. It’s worth talking to a professional if you’re going through hell, etc. etc. etc.

1 - Let the hate flow through you

A founder I respect once told me his secret to keeping motivated. It’s wonderful:

He’d had a humiliating investment pitch with a partner at A16Z. The guy was a total asshole. He sneered at their business with a holier-than-thou vibe that only someone who’s gone Private Equity → MBA → VC (and, of course, never started anything) can truly master.

So what did this founder do? He printed out a picture of this VC and taped that picture to his laptop. It stayed there for years. Every time he felt like cutting a corner or taking it easy, he had a picture of this VC staring at him. He’d quietly say, “fuck you, I’m not letting you win,” and get back to work.

I do something similar. I have a set of angry emails and experiences stored up in my mind that I use as fuel.

Is it healthy? OF COURSE not. Is it effective? Absolutely.

2 - Become a force of nature

Some people talk about their company’s mission inspiring them to push through the stress. That may be true… but also, we’re in B2B software. When facing crushing stress, I don’t know that the mission, “improving accounts receivable workflows” is really going to get me amped to enter the battle.

I’ve learned from some amazing startup salespeople - shoutouts to Steve Travaglini and Jack Hannah - that it’s not necessarily just about the money either. They seem push through pain, rejection, and stress… to become the best version of themselves.

I’ve heard things like:

“Getting through this will make me more of a force of nature.”

“I am grateful for the opportunity to be the person who figures out something like this.”

Pushing through difficult things can make you better - especially if you view each difficult thing as one more step towards becoming a force of nature.

3 - Do it for the scoreboard

Sometimes, you’re in a shitty situation and feel like you’re backed up against a wall. Let’s say you’ve got very limited runway and an unclear path to your next fundraise. You can become hopeless, nihilistic. You can feel like you’re trapped.

The question I ask is, “Let’s say you’re looking back on this exact situation a few years from now. Looking back, you’re proud of how you handled it. What did you do?”

Even when situations seem hopeless, just saying, “fuck it, this is to make my future self proud” can help you push through. For me, this led to a massive Hail Mary pivot that led to us going $0-$4M ARR in 2 years… after wasting 2 years of life in pre-PMF hell. The important thing: Regardless of the outcome, I’m proud of how I handled myself in that particular crisis.

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Helpful? Insane? Let me know - reply to this email or reach out on LinkedIn, I reply to just about everything.