Eating glass

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The hardest part about being a founder isn't building the tech. It's not hiring, or managing a team. It's not marketing or retention.

It's all mental.

Because everything that could go wrong usually does. Elon famously described running a startup as "staring into the abyss and eating glass" … and I get it. Most startups fail. You're almost always in fear of total collapse. And the stakes are high, with a lot of other people's capital on the line — investors, and sometimes friends and family.

Most people choose jobs they enjoy, and leave when the work turns unpleasant. As a founder, you don't get to choose. You work on what the company needs… which is usually the most painful and broken problem, week after week.

To shoot it straight — it's really not fun a lot of the time.

When my cofounders and I first came up with beehiiv, we all had full-time jobs. We spent every night and weekend on this little side project with no guarantee it would ever lead to anything.

That first year may have been the most mentally taxing of them all. I turned down dinners and concerts and trips with my best friends to stay home alone in my room shipping code for a platform with zero users.

Sort of building with one foot in and one foot out. Like it could work and be something one day, but right now it's nothing at all. And at any moment my cofounders could have a change of heart, or a competitor could launch something to make our thesis moot, and all of those late nights and weekends would be for nothing.

That feeling of uncertainty, with a healthy mix of both excitement and dread (i.e. staring into the abyss), every day for a year. It takes a lot of mental strength to not quit when it feels like life is just passing you by. Missing out on all of those formative experiences in my 20s to build something that maybe no one will even want.

And when I went out to fundraise in the summer of 2021, it sure seemed like that was the case. More than 40 investors passed before we got a yes.

There are already dozens of email platforms.
I'll never see a 10x return on this.
Substack already exists.
You'll never be able to build an Ad Network.
Facebook just launched a paid newsletter service.
I don't think this is a venture-backable company.

Now imagine: you spend an entire year of your life working every night and weekend on something, only to get rejected by every investor you talk to. It's easy to fold there, but we kept going and eventually got a yes… which led to our $2.6M seed round.

We launched in November and actually got decent traction out of the gate. It wasn't an Anthropic revenue ramp, but we jumped from a few hundred dollars to a few thousand to tens of thousands in subsequent months. As difficult as the journey had been to get here, it finally felt like all of those late nights were worth it.

That feeling of momentum as a founder is euphoria. When all of your conviction and optimism shows up in the numbers, it feels like you're on top of the world.

Then one Friday afternoon in April, our cofounder and CTO tragically passed away. Not only was he the most beloved and talented person on the team, but he was also in charge of solving all of the scaling issues we were dealing with at the time.

I had to make calls to everyone on the team and share the news, then show up to standup on Monday morning with one less square on our screen and try to hold the team together. Meanwhile, I'm flying to Memphis for the funeral, my inbox is full of angry users because the platform isn't working, and my cofounders are doing everything they can to keep the pieces from falling apart.

There have been a lot of moments where it felt like this whole thing was going to fold — that was one of them. But we recovered and lived to fight another day.

And thank god that we did, because since then I've experienced some of the most rewarding years of my life. There have been so many little milestones and highs along the way: hiring that amazing candidate, closing that big deal, surpassing $1M ARR, then $5M, then $10M… then $30M.

But for each of those highs, there have been plenty of lows to balance it out: getting ghosted by candidates I loved, firing people who were instrumental in the early days, needing to raise more money, influential customers churning, employees leaving.

In the moment, each of these feels catastrophic.

I remember GoDaddy unexpectedly shutting down our account and taking all of our users' websites down with it. I remember making a mistake with our email infrastructure in the early days and all of our customers' emails going to spam for two weeks.

I remember all of the days and nights I spent 16 hours working alone in my bedroom, internalizing all of the negative externalities of startup life, questioning whether this was ever going to work. Four years later, projecting $50M in revenue for 2026, and I still have those days.

Being a founder is just bouncing between the highest highs and the lowest lows, and trying to stay sane through it all. I still feel all of the stress and uncertainty I did when I began this journey. But mentally, I've matured a ton as a founder.

Let me paint a picture.

On Sunday night, I'll round up a list of priorities and go to bed excited to work on them. But by Monday morning: something broke, someone needs something from me, there's an escalated customer in my inbox, there are people issues on some team I need to resolve, and suddenly 3 extra meetings on my calendar.

By Monday night, not a single thing from my list got done. Now repeat that every single day. That’s life as a startup founder... and it used to drive me mad.

I was in a perpetual state of adding things to a to-do list that only got longer, with no time to actually do them. I'm still in that state today… but I've come around to learn that that is the job.

My job is to solve problems, remove blockers for others, and make difficult decisions. Instead of fighting the reality of what it means to run a company, I embrace it.

I know that I am not going to get a block of four uninterrupted hours in the middle of the week, so I religiously work every weekend to get that stuff done. It's the only way that I can be more present during the weeks without feeling like I'm drowning.

Maybe it's the yoga and breathwork, but I feel much more grounded today in what I can and cannot control. I used to let everything bother me. But some days it's going to rain, people are going to act irrationally, vendors are going to make mistakes.

That's life. I don't let it get to me as much anymore.

Back when I was in college, I majored in engineering, did research in some lab, and launched a startup that consumed all of my time. I somehow still managed a social life in a fraternity and had a whole lot of fun. Sleep and health were the primary trade-off there.

After my college startup fizzled out, I joined Morning Brew as the second employee, taking on founder-like responsibilities from the jump. I worked my ass off for 3.5 years and rode that wave up until the acquisition by Business Insider in 2020.

That following year was the one I wrote about above, tirelessly building beehiiv on nights and weekends with my cofounders. It was all-encompassing. I sacrificed a lot of time and experiences to bring this thing to life.

When we launched, I wasn't capable of giving up the work ethic (and never will) — I knew this thing needed 80+ hours a week from me to succeed. But I also couldn't keep suppressing all of the life I was letting pass me by.

Of course I wanted the success, but I also wanted to be a normal 27-year-old who could hang with friends, go out on dates, travel and experience life outside of work. So I learned how to do both.

I began to burn the candle at both ends, and for a while, I felt invincible. The company was growing a ton month over month, the product was so dialed, and I could lock in and binge work for 16 hours at a time. But I could also be the last one out and still make it to the gym at 7am.

I basically tried to have all three:

My work ethic never changed, I was just trying to overcompensate for lost time in my social life.

That culminated with one bender in Medellín where I was out til 4am three consecutive nights (starting on a Wednesday), powering through the workdays with Adderall and cold brew. That landed me in the hospital on Saturday morning thinking I was going to have a heart attack.

Sometimes a good wake-up call is needed. Trying to navigate a Colombian hospital with my broken Spanish thinking I was going to die was a really gnarly one. I don't regret a thing, but I knew that I had been flying too close to the sun.

Between that episode and another where I way overcommitted on work travel while trying to maintain the same level of output — I hit a breaking point and decided I needed to invest in my mental health if I was going to survive this thing.

I cut coffee cold turkey almost two years ago. Running a startup, I already operate with a heightened baseline of cortisol and stress as is. I don't need any extra.

I meditate for at least 15 minutes every single morning, non-negotiable. I started with some guided meditations, and now just freestyle while listening to some hippie sound bowl melody.

I used to wake up at 5:30am and scroll Slack before even getting out of bed (being in LA, I'm 3 hours behind most of the team). Jumping from channel to channel triaging problems and putting out fires, all before the sun rises, isn't a particularly healthy way to start the day.

Now, I don't touch my phone for the first hour after I wake up. I protect that time to ruminate, stretch, meditate, whatever — without the influence or disruption of the outside world. Almost all of my best ideas happen in that hour.

I don't touch my phone the hour before bed either. Instead, I read every night and it's made a massive difference in the quality of my sleep (confirmed by my Eight Sleep … not an #Ad).

We're still so early in understanding our health, and how the food we eat, air we breathe, water we drink, content we consume, and products we use actually impact our wellbeing.

I've installed reverse osmosis filters in my apartment and only drink ultra-filtered water. I have hardcore air purifiers in every room. I'll measure my glucose from time to time to make sure my diet isn't working against me.

I'm not trying to live forever. I'm not even trying to longevitymaxx… I just want to feel incredible today.

I want to build beehiiv into a multi-billion dollar business. I want to scale this newsletter and community to millions of founders. I want to create tons of incredible content, build fun side projects, explore the world with my friends, and have a damn good time doing it all.

That all takes a ton of energy and ambition. I want to do everything I can to always feel and be at my best.

I started this post by writing that the hardest part of being a founder is mental. Mentally, I feel like a totally different person today than when I first started the company.

Recently, when people ask how work is going, I tell them: I'm working more, and harder, than I ever have. But I feel less stressed and more in control than ever before.

It's all mental, baby.

If you enjoyed this post or know someone who may find it useful, please share it with them and encourage them to subscribe: mail.bigdeskenergy.com/p/eating-glass

One of my cofounders is backpacking through the Dolomites right now. I don’t know if this office actually exists, but Jake if you see this message hop on we have a big meeting tomorrow at 11a ET.

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