How Tyler Denk Grew beehiiv to a $250M Business in 3.5 Years

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Aug 8, 2025

Tyler Denk, founder of beehiiv and former tech innovator for Morning Brew, shares his inspiring entrepreneurial journey, highlighting the leap from heavy student debt to launching a $250M business in just 3.5 years. He discusses the importance of betting on oneself and pursuing meaningful risks over stability. Tyler reveals how he navigated career choices, tackling the complexities of startup culture and ambitious hiring. His insights on product development speed versus quality and the challenges of fundraising provide a fresh perspective for aspiring entrepreneurs.

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ANECDOTE

From $120k Debt To Freelance Hustle

Tyler graduated with $120k of student debt and lived in his parents' basement before finding freelance work to survive.
He taught himself web work, built Shopify sites for clients, and took any paid project to avoid insolvency.

ANECDOTE

Choosing Upside Over Certainty

Tyler turned down a signed Deloitte offer, a lease and a girlfriend to join Morning Brew full-time after freelancing for them over the summer.
He chose asymmetric upside and the chance to be the only person building the product over the safety of a large firm job.

ADVICE

Use Regret Minimization To Choose Risks

Apply a regret-minimization framework: pick the path you'll regret least later and that offers asymmetric upside.
Weigh trade-offs consciously and favor learning, skill growth, and the best story for your future self.

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In this episode, Tyler Denk sits down with Wouter Teunissen to talk about the incredible founder journey he has had starting beehiiv. After graduating college with $120K in student debt, Tyler Denk faced a tough choice: follow the safe path or take a leap of faith.

Broke and living in his parents’ basement , he said yes to a freelance opportunity from a childhood friend—building early tech for the newsletter Morning Brew. With just 49 cents in his bank account, he bluffed his way into the role, pulling all-nighters to teach himself what he didn't know and barely holding it together.

But he didn’t quit. He built fast, listened hard, and proved himself through execution, not credentials.

When Morning Brew offered him a full-time role, Tyler turned down a signed Deloitte offer, a girlfriend, and a lease in D.C. for a shot at something riskier—but more meaningful. He chose asymmetric upside over certainty. That mindset—betting on himself, learning through doing, and minimizing regret—became his foundation as an entrepreneur.

From building Morning Brew’s referral engine to founding Beehiiv, Tyler’s journey is proof that high agency beats pedigree. It's not just about chasing success—it's about designing your own luck through relentless ownership and speed.

His story isn’t a blueprint for life; it’s a challenge for you to stop optimizing for safety and start optimizing for growth.

Follow:
Wouter - @WouterTeunissen on X
Biography Newsletter - https://biography.beehiiv.com/
Tyler - @denk_tweets on X
Tyler's newsletter - https://www.bigdeskenergy.com/
beehiiv: https://www.beehiiv.com/

Timestamps:
(0:00) Intro
(0:46) Graduating College with $120k in Debt
(16:36) Why you need to realise that everything is a tradeoff
(25:33) Principles in Hiring Talent – Looking for High Agency
(37:04) Communication as a Founder is of paramount importance
(45:56) The importance of feature-led marketing to get organic marketing
(53:20) The Importance of the early Morning Brew Days
(1:04:28) Why Tyler left Morning Brew to Join YouTube Music
(1:15:28) The Nights and Weekends Project that became Beehiiv
(1:27:10) How Tyler Fundraised A $2.6M Seed Round in 30 days
(1:32:32) Why You Should Build in Public
(1:48:27) Rejecting $30M Within 18 Months of Work