Founder in Focus: Tyler Denk of beehiiv

This week's Founder in Focus features co-founder Tyler Denk of beehiiv, a Fund IV portfolio company that streamlines the ability to create, customize, monetize, and scale email newsletters. beehiiv was co-founded by Morning Brew alums Tyler Denk, Benjamin Hargett, and Jake Hurd.

Tyler’s entrepreneurial drive is a combination of four things: physics and engineering, eternal optimism, a general annoyance when things don’t work properly, and he’s hyper competitive. He fell in love with physics in high school and studied engineering in college. Tyler is completely infatuated with learning how the world works while pursuing the most optimal solutions to complex problems. 

This combination keeps Tyler looking through the lens of “how can this be done better?” He says this approach has been both a blessing and a curse, but he loves solving problems and the challenge of trying to do it better than anyone else. And if you really have an entrepreneurial spirit, Tyler says’ it’s hard to find a well-defined “job” that scratches that itch. While some people love direction and boundaries, others thrive in open space and ambiguity. Tyler has always enjoyed the latter. 

His family work ethic runs deep. Tyler’s father ran a car detailing business on the side while working full-time. He did this throughout most of his career, waking up at 4:30am every morning for his full-time job and detailing cars on his day off. Tyler says his dad’s work ethic was next level, and he never once complained. But more than work ethic, Tyler observed the passion behind it. A love of cars. His dad took tremendous pride in his work. He knew he could provide better service than the larger chains. Tyler says, “It’s as cliche as it gets, but I truly don’t think he ever felt like he was ‘working’ when he was detailing these cars. He truly loved the craft.” In addition, Tyler’s grandfather started a large shoe business in Baltimore when he was in his 20’s. And at 95 years old, he still shows up to work every day. 

Birth of beehiiv

Tyler had joined Morning Brew back in 2017. He was the second employee. His role spanned engineering, growth, and product; the classic early startup employee roles. He was able to build a lot of impactful custom tech: the website, the referral program, the content management system, the ad management platform, the cohort analytics, and more. Tyler did everything needed behind the scenes for a newsletter sent out at 6am every morning. It was an entire bespoke tech ecosystem that fueled internal operations and growth. He had a front row seat and a hand in building what would become a 3.5 million subscriber behemoth, and the true leader in the newsletter space.

From his front row seat, Tyler witnessed a ton of inbound interest from others wanting to leverage some of the tools used by Morning Brew. His eyes opened to the potential utility of some of the things he’d built, and he saw a void in the market. 

Simultaneously, a few other platforms in the newsletter space were gaining notoriety. But from a pure product perspective, Tyler was unimpressed. He felt his unique perspective on what it takes to scale a massive newsletter and his first-hand experience building tools, along with the gaining popularity of newsletters, was a real opportunity to build something special. Tyler, along with his co-founders, are “democratizing” access to the tools that give other newsletters the ability to flourish.

The experience and perspective beehiiv brings to the space has made them stand out. The early days at Morning Brew and the caliber of the team has made their platform unique. They’re not just copying everyone else's playbook. They’ve spent years honing and refining content, sales, and growth. They’re building tools, dashboards, processes, and customization that fits creators exact needs. The granularity of insights and feedback has compounded over years of iterating and scaling. This gives beehiiv an advantage and unique edge in separating what moves the needle in the industry from what’s vanity. 

Entrepreneurship

Coming back to Tyler’s own journey into entrepreneurship, I rounded out our interview looking for some insights useful to up-and-coming entrepreneurs:

When it comes to generating new ideas, Tyler says it’s hardest to come up with new ideas if you’re consciously trying to come up with new ideas. Surrounding yourself with smart, curious people and engaging with others is the catalyst that will take you to the next level.

For motivation, Tyler has reached the conclusion that there’s no one thing that motivates him. It's the confluence of expectation, emotions, and aspirations moving the needle together. And Tyler continues to evolve as an entrepreneur. He says he’s enjoying the process more now than in his younger days. He grew up reading TechCrunch and viewed the startup world as all glamour and upside. And though he realized it would be difficult to scale a startup, he’s come around to genuinely enjoy the day-to-day challenges versus growing frustrated.

I asked Tyler what has been his greatest entrepreneurial achievement so far, and he says he’s still very much in the thick of it. He hasn’t had a huge successful exit to hang his hat on yet. He’s not filed any life-saving patents; it’s the small victories. For instance, successfully hiring someone to join the beehiiv team really resonates with him. Tyler notes everyone is on their own career trajectory. They’re looking for ways to advance their careers and position themselves for success. So when someone makes the decision to join beehiiv as what’s best for them, it just hits different. There are so many layers of validation packed into that decision for Tyler. 

One of the books that’s inspired Tyler most is The Go Giver: A Little Story About a Powerful Business Idea by John David Mann and Bob Burg. As for growing as an entrepreneur, Tyler says it’s important to read and listen. “I think one of the best things to acknowledge is that there’s way more that you’ll never know than the inverse.” according to Tyler. Tap in to other people’s experiences and extract that knowledge, whether it’s articles, books, podcasts, etc. Position yourself to be well-informed and malleable. Constantly learning and adjusting is the key to succeeding as an entrepreneur. Other than that, there really is no winning formula. The best entrepreneurs often fail many times. Tyler says you should develop the ability to keep learning and trying.

In the weeds

What popular entrepreneurial advice do you agree/ disagree with? Why?

The ‘hire fast, fire faster’ mantra is one of those bits of entrepreneurial advice Tyler disagrees with. He says hiring is exhausting and firing is even more exhausting. The constant shuffling and instability of a startup team in the early days does more harm than good. Tyler also recommends you avoid putting yourself in a position where you need to make a quick hire out of desperation.  

Who is the one entrepreneur to be your greatest example and inspiration?

Elon Musk. 

How do you define success?

I think it’s totally subjective, but for me it’s having the ability to spend time doing what I want to do, when I want to do it. 

What entrepreneurial tricks (hacks) have you discovered to keep focused and productive in your day-to-day busy schedule?

I try to cluster all my day’s meetings into a 2-3 hour block. That gives me the rest of the day to focus and do deep work without the constant context switching. 

What advice would you give to people who want to go into business?

Start with something you have a true competency in. I’ve attempted several side projects in industries and disciplines that were flashy and popular, but I had no business being there. Being able to really command the space you occupy due to experience or reputation really helps legitimize your business and have others (customers and potential employees) believe in you.

What is your greatest fear, and how do you manage fear in general?

Not spending enough time with the people I care about. More often than not I try to keep it top of mind because it's usually less scary to face it than to suppress it.

In what way has becoming an entrepreneur turned you into a better person?

It’s forced me to create a ton of great habits. To put myself into the best position to succeed, I need to be locked in and feeling good/motivated for sustained periods of time. To do that I’ve developed a ton of great habits like waking up early to go to the gym, eating healthy, meditation, reading at night, going to sleep early, etc.

Share some of your failures and the best lessons you have learned from them?

The biggest failures (or at least the times I’ve felt the lowest) are when we haven’t been able to close a hire I was really optimistic about. For all the reasons I see a successful hire as incredibly validating, having someone reject your offer is just as extreme in the opposite direction. It’s more so amplified on a small team in need of additional bandwidth, and after spending weeks working your way through the hiring process. The few lessons I’ve taken from this is that it’s never done until it’s done (so keep the pipeline flowing), and more importantly you need to do everything you can to position the company in such a way it’s in their best interest to take the offer. No ones going to accept an offer because you really need them. They’re going to do what’s best for them. So build the company in such a way where they’d be foolish to decline an opportunity to work for you. And don’t forget part of hiring is selling too.

What sacrifices have you had to make to be a successful entrepreneur?

Mostly just time. There really are no shortcuts. It's a lot of work, a lot of long days, and a lot of weekends staying in. Fortunately I’m a bit of a sicko and really enjoy it, but it’s come with its fair share of missing out on spending time with others.