How Beehiiv Grew to $20M ARR and $10M Revenue: 20 Lessons From the Trenches of Startup Life
Jul 17, 2025
Last week, after 3.5 years of relentless building, Beehiiv surpassed $20M in ARR — not even counting their Ad Network and Boosts, which bring in an additional ~$10M in revenue.
Cofounder and CEO Tyler Denk shared 20 lessons, insights, and thoughts from the milestone:
While I’m not one for the birthday-listicle “life lessons” posts, this milestone felt worth reflecting on. Here are 20 raw, practical lessons I’ve learned along the way — from scaling chaos to mental health to why advisors often don’t matter.
1. It Doesn’t Get Easier
The stress doesn’t disappear with scale — it evolves. Every stage brings new, often harder challenges. The myth of future calm is just that: a myth.
2. The Goalposts Keep Moving
What once seemed like a dream becomes just another number. Growth rewires your expectations faster than you’d think.
3. Most Advisors Are Just Window Dressing
They’re great for signaling legitimacy early on, but very few add real value. Set your expectations accordingly.
4. No One Cares Who Your Investors Are
Customers don’t care about your cap table. Raise from who believes in you, build the product, and the Tier 1s will follow — just like ours did.
5. Remote Work Is a Superpower
We’ve embraced it fully — it unlocks talent, flexibility, lifestyle, and happiness. I’d rather hang at the DMV than commute daily again.
6. Having Cofounders Is Underrated
When things break — and they always do — having partners in the trenches makes all the difference.
7. Tough Conversations > Avoidance
Firing, demotions, feedback — the fear is always worse than the reality. Don’t carry emotional baggage longer than you need to.
8. Dogfood Your Product
I use Beehiiv every day — for this newsletter, for our site, for everything. It keeps me close to the experience and accountable.
9. The CEO Role Changes Fast
You start building product. You end up building systems, culture, and people. Embrace the shift.
10. Storytelling Is a Superpower
It’s not just about motivating your team — it’s about building belief, alignment, and momentum.
11. There’s No Playbook
We lost a cofounder early on. GoDaddy wiped user sites. We acquired two companies. There is no prep for this — only response.
12. Shared Upside Drives Ownership
Everyone at Beehiiv has meaningful equity. When the whole team has skin in the game, magic happens.
13. Ownership Drives Excellence
If no one owns something, it doesn’t improve. Assign clear ownership, or expect mediocrity.
14. Transparency Wins
I share numbers, decks, and updates internally. Treat people like adults — they’ll repay it with trust and action.
15. Mental Health Is Not Optional
I fooled myself into thinking fitness was enough. It wasn’t. Don’t ignore your mind.
16. Founder Friends Are Lifelines
Other founders get it. Time with them = fuel. That’s why I run founder retreats regularly.
17. Speed Is the Ultimate Advantage
In the early days, speed was our moat. Build fast, ship faster, iterate always. Speed compounds.
18. Mediocrity Infects
A single “meh” hire can bring the whole team down. Don’t wait to part ways. Excellence or nothing.
19. You Have to Love the Game
I work 14-hour days and still want more. If you don’t love the process, no outcome will be worth it.
“I didn’t want to be rich. I didn’t want to be famous. I didn’t even want to be happy. I wanted to be great.” — Bruce Springsteen
20. The Best Is Still Ahead
After $30K MRR, someone told me, “You’ll hit $300K before you know it.” They were right. Small improvements compound. Every day, 1% better. That’s the whole game.
Final Thought: Keep Building
We’re 100+ people now, rowing in the same direction. Still compounding. Still proving people wrong. And still just getting started.