The Yes That Changed Everything
The success story of Tyler Denk started with a single “yes.” Not a hesitant yes. Not a calculated yes. Just a pure, gut-level, “yes” to figuring it out later.
Tyler Denk was living in his parents’ basement, $120,000 deep in student debt, nursing the sting of a failed startup. Life was uncertain. Until the phone rang.
In a recent LinkedIn post, Tyler Denk shared a saved photo that illustrated how difficult things were for him during that period — he had just 49 cents in the bank.
Austin Rief, co-founder of Morning Brew, was on the line. “Can you build something for us?”
Denk didn’t hesitate. “Yes.”
He didn’t have all the answers, but he knew he could figure them out. That one word opened the door to a journey that would lead from rock bottom to becoming the CEO of Beehiiv, one of today’s fastest-growing newsletter platforms.
That single “yes” set Tyler Denk on a path that would lead from rock bottom to becoming the CEO of Beehiiv, one of the fastest-growing newsletter platforms today.
What was the first Tyler Denk startup?
Denk’s entrepreneurial itch started during his college years at the University of Maryland. A mechanical engineering student who taught himself to code, Denk co-founded VentureStorm, a platform designed to connect student entrepreneurs with developers.
It grew to approximately 10,000 users but ultimately shut down. Still, Denk didn’t let failure define him. He treated it as a hands-on masterclass in running a startup. That mindset would prove crucial in his next chapter.
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Tyler Denk Hired at Morning Brew
Post-college, Denk stood at a crossroads. He had a safe offer from Deloitte. It was the logical path—secure, stable, predictable.
But when Austin Rief called with an offer to join Morning Brew, a scrappy media startup, Denk chose the uncertain road. At the time, Morning Brew was just a daily newsletter with 100,000 subscribers. Denk became the second employee, diving into engineering, product, and growth.
He built the referral program that became Morning Brew’s growth engine, taking the company to over 3 million subscribers. By 2020, Morning Brew sold to Business Insider for $75 million.
The risk paid off. More importantly, it cemented his belief in the power of newsletters.
The Leap of Faith – From Google to Beehiiv
Despite the success at Morning Brew, Denk was nowhere near finished making his mark. He left the company just weeks before its sale to join Google’s YouTube Music team. It seemed like a stable move—until the Morning Brew deal closed. That moment reignited Denk’s entrepreneurial fire.
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“As soon as that money hit the bank, I quit Google,” Denk said in an interview with Inc. He knew it was time to build something of his own. Alongside former Morning Brew colleagues Ben Hargett and Jake Hurd, he began developing what would become Beehiiv. The goal was clear: create a newsletter platform as powerful and intuitive as Morning Brew’s custom-built system.
For nearly 10 months, Denk worked around the clock. By day, he led product initiatives at Google. By night, he poured his energy into coding Beehiiv. It was a grueling period, but his belief in the product kept him going.
The Battle to Build Beehiiv
Going all-in wasn’t easy. Investors were skeptical. Could a small team really challenge platforms like Twitter’s Revue or Facebook’s Bulletin?
But Beehiiv pushed forward. In mid-2021, they secured a $2.6 million seed round, giving them the runway to quit their day jobs (see the pitch deck here).
But the startup’s challenges were far from over.
- Personal Tragedy: In May 2022, Beehiiv’s co-founder and CTO, Andrew Platkin, passed away unexpectedly. The loss was devastating. Denk later shared that losing a key team member so early nearly broke the company. But despite the grief, the team pushed forward, driven by their shared vision.
- Technical Crises: Shortly after, Beehiiv faced a major technical outage that took the entire platform offline for eight hours. Denk and his team pulled all-nighters, working relentlessly to stabilize their infrastructure and ensure it wouldn’t happen again.
Through it all, Denk’s resilience never wavered. He leaned on the lessons learned from his early failures, understanding that entrepreneurship is as much about endurance as it is about innovation.
Resilience Rewarded – Beehiiv’s Rise
Against the odds, Beehiiv grew fast. Within a few years, they hit $15 million in annual recurring revenue. The platform became known for its intuitive tools, powerful analytics, and creator-first approach.
Denk’s early “yes” wasn’t just to Rief—it was to his own belief in what was possible. It sparked a chain reaction of risk-taking, relentless work, and resilience.
Lessons from Denk’s Journey
Denk’s story isn’t just about business. It’s about betting on yourself, even when the odds are unclear.
- Say Yes, Then Figure It Out: Denk didn’t wait until he had all the answers. He trusted that his ability to learn would catch up to his ambition.
- Take Calculated Risks: Turning down Deloitte. Leaving Google. Every risk Denk took wasn’t reckless—it was a calculated move rooted in belief.
- Resilience is Non-Negotiable: Loss. Technical breakdowns. Investor skepticism. Denk faced it all, and his refusal to quit made all the difference.
- Embrace the Grind: Denk spent nearly a year working two jobs—building Beehiiv by night while working at Google by day. Success didn’t come easy, but it came because he didn’t give up.
Big Wins With Small Steps of Courage
Tyler Denk’s journey from his parents’ basement to leading Beehiiv is a masterclass in saying “yes” to possibility. His story is proof that sometimes, the biggest wins start with the smallest steps of courage.
So the next time an opportunity comes knocking, consider what’s really holding you back. Say yes if it feels right. You can figure out the details as you grow.
Because sometimes, one yes can change everything.
