10 Lessons from $30M ARR

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Last week we surpassed $30M ARR at beehiiv. That doesn't include the Ad Network or Boosts, which account for another ~$15M in revenue.

Here's what that looks like as a tweet:

When we surpassed $20M, I wrote a post sharing my 20 lessons and takeaways from the journey up until that point. It was a massive hit — one of those newsletters that got tons of positive replies.

Don't worry, I'm not going to make you read 30 takeaways (I don't have the time for that). Instead, I'm going to share 10 lessons from this past year.

The journey from $20M to $30M took just under 10 months, but it was filled with some of the most challenging stretches in the company's history.

I hope you find them useful…

I'm cheating a little bit here, because this is the same one I started with in my previous list. But it's a good reminder to myself, and a good lesson to share with other founders.

There were times in the early days where I'd start the morning with an inbox full of angry customers, fight engineering fires through the afternoon, then answer support tickets myself until midnight. Those days felt like hell and I couldn't wait for a future that was a bit more calm, delegated, and steady.

Fast forward to today and I haven't felt the slightest sense of calm. I have just as many problems (if not more) today as I did back then.

Different levels, different devils.

Up until a few quarters ago, I could literally feel the strain of adding each additional hire. The company felt heavier and somehow it required more of me and my time. It made me reluctant to grow the team.

But with the right caliber of leaders, you can absorb new people without feeling it. We could hire 10 people tomorrow and I wouldn't notice.

For the record, I do meet with every new hire. The point is it doesn't drain my time and focus like it used to.

We have a 90-minute leadership meeting each week to review metrics and discuss the current priorities, issues, and everything in-between. But 90 minutes isn't enough — it's barely enough time to resolve the issues du jour.

Meanwhile I spend my days solving today's problems and planning next week's initiatives. There's no real space to align on the long-term strategic bets we need to be making.

So we added a 3-hour strategy session to the calendar this week. I learned that we have to be deliberate about making space for this kind of planning.

If we want to do $80M in 2027 (we do), we have to make the decisions and investments today that get us there. But if you’re always heads down in the day-to-day, you'll totally miss the bigger picture.

This startup thing is no joke. I've faced many episodes of burnout, anxiety, grief, and uncertainty throughout this journey.

Last year I decided to prioritize my mental health: I cut coffee, meditate every morning, don't touch my phone when I wake up, read before bed, plus a bunch of other habits that have genuinely changed my life.

On the physical side, I took it up another notch too:

I feel better and healthier than ever before. Which means I can think more clearly, focus for longer, manage stress better, and generally bring the best version of myself to work every day.

There was a time not too long ago when I had 18 direct reports. My calendar was filled with meetings and I spent most of my time managing people, teams, and expectations.

But I didn't start a company to sit in meetings all day. I started beehiiv because I love to build. Making space to be creative and bring new things to life is where I find the most fulfillment. Big Desk Energy is a great outlet for this (as an example).

A lot of founders build companies that they eventually hate to run, and are forced to sell or move on because of it. I recognized that I was going down that path and made some changes.

Today I have half as many direct reports and spend more of my time on product, growth, and the parts of the business I genuinely enjoy.

You're in control of how you build your company — you should prioritize yourself or you won't last.

Our text editor used to be pretty mid. My cofounder, Jake, would begrudgingly fix bugs when users reached out, but it was never his priority.

But the editor is one of the most important parts of the app. We hired someone to make it their top priority and own its success end-to-end.

Now it's our default playbook. We hired a Head of Podcasts to lead that product, which was 1000% the right move. Ditto for the website builder, digital products, and our other key offerings.

Up until about 30 employees, we had a daily standup where everyone in the company shared updates and chatted together. We had a monoculture and it was so easy to understand what everyone valued and respected.

beehiiv today is 130 people across nearly a dozen timezones. The culture still exists, but we have to be much more intentional about it.

We're actually redefining our company values right now. Rewarding the people who exemplify them (and parting ways with those who don't) matters all the more at scale.

When you're small, you're always looking to punch up and partner with companies that might help you reach new customers and distribution. When you're large(r), you're constantly fielding these requests for integrations, partnerships, and marketing.

You can usually make a strong case for each one. They often make a ton of sense. But there's no free lunch — each thing you commit to means several other things you can't.

And it's not just partnerships: it's speaking opportunities, panels, dinners, events, conferences, meetings, and more. My team tried to convince me to fly out for NY Tech Week last week, but the non-stop travel has been wearing on me and I couldn’t handle another cross-country trip.

Saying "no" is a superpower. It just gets a lot harder at scale because the opportunities are so much bigger.

Granted, we compete with dozens of companies that are many multiples our size (in terms of revenue, customers, and employees) and plenty of venture-backed startups with much more funding. We are by no means the market leader (yet).

But we're also not this tiny upstart that everyone is rooting for anymore.

There are so many new startups taking aim at us and trying to eat our lunch. We used to only focus on out-innovating and counter-positioning against those ahead of us — now we have to watch the ones behind us too.

Everyone loves a good underdog story. You get just a little bit less love as you climb to the top.

I'm not perfect. There's always room to improve. But I am damn proud of the company we have built and the platform we provide employees. beehiiv genuinely has a very special company culture.

We work entirely remote, and encourage people to work the hours they feel the most productive, from wherever in the world they want to be. We have two focus days per week (i.e. meeting-free), and in general have fewer meetings than any other company I've been a part of.

Everyone at the company is so incredibly smart and passionate about what they do, but no one takes themselves too seriously (the all-hands chat is mayhem and I get roasted all the time).

We encourage people to be themselves, and post their thoughts and accomplishments freely online. That has led a handful of former employees to leave and launch their own businesses, and others to join some of the fastest-growing startups in the world.

Like I said — beehiiv as a platform.

We have built a place where exceptional people come to do exceptional work, and we elevate them for whatever is next, whether it's taking on more here at the company or elsewhere.

Twice a year we do an anonymous survey to collect feedback. The overwhelming majority of people feel what I feel, love being here, and appreciate the opportunity and platform the company provides.

But there is a small cohort that we can seemingly never appease. For example, I thought our recent company offsite in San Diego was the best yet — the in-person time together and vibes were immaculate.

In the survey, though, there's a vocal minority: San Diego was too cold, there were too many meetings, also not enough meetings, the hackathon wasn't long enough, but was also too long, etc.

I don't want to conflate constructive criticism with unfounded complaints. Like I said, these surveys are genuinely helpful and there's always room for improvement.

But as a founder who cares so much about what we're building and our people, I'd be lying if I said it wasn't frustrating to see feedback that's so negative (and unappreciative?).

But that's the law of large numbers at play. At a certain scale, it's impossible to make everyone happy. And unfortunately, that's just the way it is.

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/10-lessons-from-30m-arr

Unfortunately, the rumors about me being on a yacht in Monaco for F1 were not true. If I were there, I would imagine it would look something like this.

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