A hard-won guide to staying mentally healthy while building a startup
I founded Stitcher, the podcast platform, in 2007 and ran it for seven years until we sold in 2014. We raised through Series B with investors like Benchmark and NEA. From the outside, it looked like a typical startup success story.
The reality? It was brutal in ways nobody talks about. We were within a month of running out of cash three times. We had to lay off almost half our team at one point. We were never growing fast enough, and there were a million other “punches in the face,” as YC calls them.
In the beginning, I didn’t actively prioritize myself enough—and it really hurt me. By the end of year two, I was physically and mentally exhausted. I was taking tons of stimulants, working 90+ hour weeks, drinking when I got home to numb the pain. I had zero balance. I felt like Stitcher was the center of the world, and every failure felt deeply personal.
That second year, I committed to making changes. I spent the next six years testing and implementing things to improve my mental state. Since leaving Stitcher, I’ve been an EIR at a venture firm, invested in and advised startups, ran the early stage Startup BD team at AWS and I’m currently a fulltime founder coach. I’ve spoken with literally thousands of founders about this challenge.
What I’m sharing here are the things that helped me most. None are magic bullets—you know you’re supposed to sleep and meditate. But I hope sharing my personal experiences will motivate you to prioritize yourself a bit more.
What Makes a Good Startup Founder?
Besides luck, what are we striving for? Early on, it’s this: the ability to fail, recover quickly, iterate, and fail again almost constantly… while inspiring others to follow you… for a long period of extreme uncertainty.
That’s the ugly truth about finding product-market fit and early growth. At Stitcher, our first product was an iTunes plugin to help organize podcasts on your desktop (the iPhone didn’t even exist yet). The first version was so bad that after launching, we had exactly zero retained users. We had to pay people to try it just to understand why it was so terrible.
A lot of what makes a good startup founder is hard, painful, unnatural, and exhausting. You end up feeling like crap a lot of the time. So perhaps not surprisingly, the key to the mental game is prioritizing yourself—specifically, activities that help you feel less like crap. That’s what allows you to do more of the failing and recovering, and to do it better, more objectively, and more authentically for longer without burning out.
I bucket these activities into three categories:
1. Maintaining Perspective
These activities help you stay objective, be happier, calmer, more empathetic, and see things more clearly. They make you a better leader.
Make Founder Friends—and Talk to Them Regularly
This probably helped me the most. One of the most difficult things about being a founder is that you generally have to be very positive for everyone, and you can’t really talk openly about what you’re dealing with. You end up carrying a lot inside. It’s incredibly lonely.
I created a CEO support group with 4-5 founders. I invited two friends, they each invited a friend, and the group evolved over time. We met monthly for two hours, from 8-10am, rotating between offices. The format was simple: the host got to complain first, unless someone had something urgent.
Deep friendships developed in our group. The two friends I brought together? One is now a VC and invested in the other’s second company. Take advantage of founder communities—get each other’s numbers, self-organize, and create these support systems.
Meditate
There’s research showing meditation reduces stress, positively affects emotions and mental well-being, and increases clarity. Try “box breathing” (used by Navy SEALs): breathe in through your nose for four counts, hold for four, exhale for four, hold for four. Repeat. It’s simple but effective.
Volunteer—Help People with Bigger Problems
I know what you’re thinking: “I have so much on my plate, and this guy wants me to volunteer?” When I was running Stitcher, I didn’t have a family or much of a life—this was about the only other thing I did most weeks.
I started volunteering as a mentor for underserved kids about a year into Stitcher. I mentored Damante for four years, hanging out every Sunday. It feels great to give back—there’s actually a name for the feel-good effects: “giver’s glow.” Scientists have shown that when you’re giving, you get additional dopamine and endorphins.
As a leader, it’s your job to lead by example. I brought Damante to our office sometimes, and our team would light up around him. It had the opposite effect of what I feared—instead of looking like a bad example, it energized everyone and inspired other team members to give back.
Read Books About People with Bigger Problems
I started reading long biographies of great leaders in history, partly to help me put away my phone and transition to sleep. A surprise benefit was perspective. When you’re reading about Harriet Tubman or Abraham Lincoln—what they went through and what was on the line for them—your revenue not hitting targets doesn’t feel as catastrophic.
Keep a Gratitude List
Quick and easy: write down things you’re grateful for regularly. It helps you look around and smell the flowers. Studies show it improves your mood and ability to handle adversity. Set a reminder to do it 3-4 times a week and write down three things. It can be simple like “I have a place to sleep” or more specific like “I had the opportunity to talk with founders about this topic I’m passionate about.”
2. Wellness: The Foundation
My lack of self-care was probably extreme, but the single biggest difference maker to my state of mind was taking care of myself—fixing my sleep, eating healthy, not consuming bad things, and exercising. There are so many studies about the effects of each on cognition and performance that it’s simply fact.
Sleep: The Game Changer
For the first 1.5 years of Stitcher, I averaged 4-5 hours of sleep a night, then would occasionally sleep 12 hours and figure I was caught up. That doesn’t work.
Here’s what crystallized it for me: We had to raise our Series A in 2008. I’d pitched 90 VCs and 89 had passed. I was at the one-yard line with one potential investor when they asked me to meet with their EIR. It was a terrible sleep week—I was working non-stop and just trying to power through with caffeine.
In that meeting, I literally couldn’t do simple math. The guy must have thought I was a complete moron. We didn’t get the term sheet. It was a huge wake-up call: How can I make the complex decisions necessary to run a startup if I can’t even get through a meeting like this?
Contrast that to the Benchmark round—once I’d started prioritizing these things. I slept 7.5 hours the night before the partner meeting and went for a run. I was doing perspective exercises. We also didn’t have nearly as much user growth as in 2008, and we were six weeks away from running out of cash. But prioritizing myself was a really big part of why that meeting went well.
Sleep tips that helped me:
Same wake time, even on weekends—your body is on a clock
No screens within an hour of bedtime (TV, phone, everything off)
No alcohol—it reduces sleep quality
Say goodnight to your phone and leave it outside your room
Get Help If You Need It
This is the most serious thing I’ll discuss. UC’s Michael Freeman found that entrepreneurs have much higher prevalence of mental health conditions and are more vulnerable to depression and substance abuse. This is made harder by the fact that as founders, we have to be cheerleaders for our companies.
If you’re depressed or experiencing suicidal thoughts, please get professional help immediately. I never experienced depression or suicidality, but I did mask stress with Xanax and alcohol at night. Putting aside the health risks, it impaired the most important things I needed as a leader: judgment, mood, energy, clarity.
When I eventually fixed my evening routine, within two months everything was better. If you’re doing this and need professional help, get it. There’s no shame. More startup founders are opening up about mental health—don’t mask the pain with substances.
Exercise
We all know exercise helps. I’ve always exercised regularly—it was one of the only healthy things I did at the beginning of Stitcher. One tip: if you’re super competitive and going hard when you exercise, but feeling fatigued in general, tone it down. During Stitcher, I found that if I pushed over 70%, the tiredness afterward would outweigh the benefit.
3. Trusting Yourself
As a founder, one of your most important jobs is making decisions. Early on, that can be hard.
Write It Down
Use a simple pros/cons sheet. It’s amazing how much writing forces clarity of thought. It helps you clarify the decision for yourself and articulate it to others. You’ll likely make unpopular decisions, and this process helps.
It also helped with self-awareness. I realized that any decision involving people and feelings was hard for me. I’m sensitive and feel people’s pain more deeply than most. So decisions like firing someone or scrapping something people had been working on—I wasn’t weighing correctly. Being aware of it and writing it down really helped.
Get Feedback
Once our team was over five people, we sent out four anonymous questions to all employees monthly. It was amazing how much this helped with my blind spots, though some feedback was painful to read.
The Bottom Line
I don’t want this to feel like another “thing you should do.” You don’t need to wake up tomorrow stressed about writing gratitude lists. This is about being gentler with yourself and doing things that are truly for you.
We all know how hard this job is. It’s also very rewarding—especially when you’re prioritizing yourself. The startup journey is brutal enough without making it harder on yourself than it needs to be.
Take care of yourself. Your startup—and everyone counting on you—will be better for it.
