How long can you build a company you believe in as a side hustle before something has to break?
From a Baltimore basement with $120 thousand in student debt to building the entire tech backbone of Morning Brew, Tyler Denk had already lived a few lifetimes. Last we left off, he'd been told no to the idea of spinning that solution into its own business, taken a new job at Google's YouTube Music team, and decided to keep building his idea anyway with two friends.
The trio of Tyler, Ben, and Jake spent a difficult ten months trying to make Tyler’s all-in-one creator platform idea work while holding full-time jobs. Tyler was still at Google, Ben and Jake at Morning Brew. Weekends and nights of meetings, sketching out a roadmap for what would become beehiiv (not a Beyoncé reference either, he swears).
Beehive was the word that came to mind. The idea was a hive of subscribers.
“A beehive felt like the perfect metaphor: because it’s the collective colony, not the bee, that really matters. It’s the shared interests and direct relationship between them that creates value.”
However, beehive.com was already taken. So they ran through variations until something was available. beehiiv was there for ten dollars, misspelled but close enough.
“If you have an amazing product, you don't have to have the perfect branding and name. I think product speaks louder than that.”
They bought the domain and started building.
“We would meet once a week, (...) run through the board of things that we needed to get done. We would show the progress from the prior week. We divvy up tasks, and we just do it all over again. It was basically one-week sprints for 40 weeks straight.”
But, there's a limit to how much you can accomplish with a side hustle and a full-time job.
Soon, one would have to go.
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As the name started to form over those ten months, so did the product. Tyler felt it had great potential. He saw how signs pointed to the newsletter ecosystem continuing to grow and become more popular among content creators and publishers.
What he had built at Morning Brew was being copied by other newsletters and media companies. That was proof that there was real interest and that the market could be big. But they didn't have a product to show for it yet.
So, they had to keep building until it became real. But there is a version of that stubbornness that is reckless, and Tyler was conscious of the distinction.
The mythology around founders tends to celebrate the all-in leap, eating-ramen kind of story, and he wanted no part of that. "We derisked this as much as we possibly could," he would say.
Tyler is straightforward about it: if you are worried about paying rent and doing groceries, building a successful business becomes even harder than it already is. So you should have some degree of financial security to be able to focus properly on building your company.
That non-negotiable is what kept them sane through the whole stretch, working full-time jobs and what would become beehiiv like crazy.
After ten months of nights, weekends, and self-imposed deadlines, they had something worth sharing. It was not perfect, but it was something. And the clock was ticking.
Why? Well, Tyler started noticing the newsletter ecosystem becoming more competitive around summer 2021. That made him anxious.
“The worst part about doing all of that is, in this period of time before you launch, or when we're working our ass off, we are anxious about it being for nothing. We're not even generating revenue, and we have zero users, so there's no feedback loop that we're even on to anything special here.”
And if you’re a founder or thinking about being one, you know you can’t blame him.
“It could be totally me in my head as an insecure and anxious founder who felt like everyone was going to take their idea and get to market first (...) Given how big the world is and how many competitors, you'd have to assume that most ideas are not totally novel.”
Every day they waited was another day some larger company with hundreds of full-time employees, as compared to their three-person team’s combined nights and weekends, could ship a feature that made everything they'd built irrelevant overnight.
Besides, the Morning Brew backstory was their strongest card, and they knew it. These were the people behind the engine that had taken a newsletter from 100 thousand to 3.5 million subscribers. That should mean something.
Therefore, ready or not, it was launch time.
In June 2021, Tyler announced beehiiv to the world with a tweet.
Four hundred people put their email addresses into the waitlist.
It sounds modest against the scale of what beehiiv would become, but, in that moment, 400 people choosing to raise their hand for such an early product was the signal Tyler needed.
The waitlist also served a second purpose. To join it, people had to answer a few questions like what platform they were currently using, and what they wished was different about it. It was market research as well as a sign-up form, and it gave the team a map of exactly which pain points to attack first.
Most critically, working full-time while also building beehiiv was no longer an option.
“I made the case that if we stay in this part-time project stage, we're just going to continue to fall further and further behind, and we're never actually going to give ourselves the best chance to compete. After we all kind of came to an agreement there, I spent July of 2021 raising our seed round.”
Around that same time, he reconnected with an old friend and mentor of his, Andrew Platkin. Andrew had been a technical advisor during the Morning Brew days, also known as the insanely competent expert guy that Tyler, as a 24-year-old self-taught developer, would always message with some version of "I think I f*cked something up", and he would always help.
When they reconnected in the summer of 2021, Andrew had just started at another startup, and Tyler pitched him on beehiiv. There was no money to pay him, but Andrew was there to help anyway.
In October 2021, the long-awaited seed round came together, led by Social Leverage, and closed at $2.6 million, with the addition of around 30 strategic angel investors, such as Jason Yanowitz, co-founder of Blockworks, a $195 million crypto media and data platform, and Anna Palmer and Jake Sherman, the journalists and best-selling authors behind Punchbowl News, a membership-based newsletter covering Washington politics.
The list goes on. Ben Kaplan & Elliot Tebele, the co-founders of Jerry Media & WhatDoYouMeme, were in. So was Adam Ryan, co-founder of Workweek, a B2B media company with newsletters across a dozen industries. And last but definitely not least, the man behind @litquidity (keep that in mind).
With the term sheet in hand, they could finally offer Andrew Platkin a real job, transitioning him from technical advisor to proper CTO. Tyler quit his job at Google as soon as the money was in the bank; the rest of the Morning Brew team waited another month.
They were all fully in. Which was good, because they would soon need every bit of that energy.
Resist the instinct to automate and systematize before you have anything worth automating and systematizing. Get close to your early user for real, because the information you gather and the trust you build in those first steps of your company are things no growth strategy can replicate later.
This iconic advice is otherwise known as "Do things that don't scale".
Why do we bring it up? Well, 400 people were on the waitlist to receive beehiiv’s first version.
Today, a company with a functioning marketing operation would feed them into an automated email sequence, track open rates, and optimize the funnel.
But back then? Tyler opened Gmail and wrote emails. One by one.
When beehiiv finally went live in November 2021, he sent an email to these 400 people along the lines of:
"Hey, we just launched. If you're on Mailchimp, this will save you 60% of your monthly cost. It's a new and unproven product, but I'll hold your hand every step of the way through."
Tyler explained that beehiiv was launched underpriced at the moment because the goal was to remove every possible reason for someone to hesitate, as well as encourage them to be more open-minded about trying it. If you were paying for Mailchimp, the math was simple: you would spend less money. Period.
The conversion rate was around 25%. In real numbers, one in four people on a waitlist said yes to an unproven product.
The angel investors gave the early momentum an extra push. They had been chosen because they were the ideal users, meaning people who already had email lists with sizable, recognizable newsletters, and had a direct financial incentive to want beehiiv to succeed.
And around 10% to 15% of them moved their lists over in those first weeks.
With the first hundred users in, the team had a victory. But victories like this rarely stand still, because there's always a new bar waiting once you clear the last one.
Now came a different question entirely.
In a market where Substack, the platform that had made it easy for anyone to start and monetize a newsletter, had already planted its flag and built a loyal following, what exactly was beehiiv, and why should anyone switch?
As it turned out, Tyler had a very clear answer to that.
At some point during those first months of real usage, users were asking to remove the "Powered by beehiiv" badge from the footer of their newsletters and websites. Tyler said no.
That decision came from data that showed something interesting. Every newsletter sent by a beehiiv user was an advertisement for beehiiv itself. Readers who liked what they were reading would see it, and some of them would follow it, and some of those would become beehiiv users themselves. It was a free, organic growth loop.
It reflected something about how Tyler thought about building beehiiv: growth was a product decision.
Morning Brew had taught him that lesson. It had the referral program and all the infrastructure that made the newsletter better than its competitors, and all of it had driven growth because it was embedded in the experience itself rather than bolted on separately.
The same logic governed how beehiiv was positioned against the market it was entering.
The obvious comparison was Substack, which had done something innovative by bundling a website, newsletter, and paid subscriptions into a single product and making the whole thing accessible to writers who had no technical background. Tyler respected what Substack had built, but had no intention of competing with it on its terms.
Substack's business model is built on a take rate. The platform is free to use, but when a writer monetizes their audience through paid subscriptions, Substack takes a percentage. For a writer making modest money, that's a manageable cost. For a creator doing serious volume, it becomes a significant and compounding expense that Tyler calls a “graduation problem.”
In other words, the more successful you become on Substack, the more expensive it gets to stay there. For him, this arrangement isn’t creator-friendly.
beehiiv's model was built on a different premise. Free up to 2,500 subscribers, then increasing flat subscription costs with the size of the list, while taking no cut of audience subscription revenue. What a creator earned from their audience was theirs.
The point was to make the math easy for anyone already making money. beehiiv was never really trying to convince people to start newsletters. It was simply offering an alternative for creators who already had an audience and wanted their growth to keep working in their favor.
With the model clear, the right creators were starting to take notice.
But a compelling argument only gets you so far. At some point, the product has to earn the trust of its users.
That moment was now.
Among Tyler’s angel investors, there was one who stood out for the size of his list: Lit, the anonymous creator behind Litquidity, one of the biggest finance meme accounts on Instagram and X/Twitter.
At the time, nobody knew who he was. That wouldn't be revealed until years later, when Lit came forward as Hank Medina, a former Wall Street banker. But back in 2021, he was just Lit, and Lit had an email audience of around 100 thousand subscribers through his newsletter, Exec Sum.
When Tyler asked if he wanted to migrate to beehiiv, he said he'd move the whole thing over if it would help, even though beehiiv was a brand-new platform and had never sent a newsletter with more than 5,000 readers.
In a single move, overnight, the infrastructure would face more load than it had encountered across all of its users in all of its history to that point. There was no way to simulate that in testing, nor any gradual ramp-up available. It would either hold or it wouldn't.
By this point, Andrew’s responsibility had grown alongside the company. He owned the most critical and time-sensitive parts of the platform, and he was right in the middle of a series of infrastructure rewrites meant to make beehiiv more stable as it scaled.
There was no one else who understood the system the way Andrew did. If this didn't hold, he would be the one staring at the wreckage, trying to figure out why.
The time came, and…
It held.
The send went out. Everything worked, and Lit never raised a concern.
The thing they'd built in nights and weekends, across months of stress and no guarantees, was carrying real weight. Tyler's relief rippled across the country.
"Thankfully, it went flawlessly, (…) it gave us a really strong case study to tell other people that we could handle that much email. He was a good social personality that helped amplify the case study and social proof.”
It was the first time the question of whether beehiiv was real had a definitive answer.
It probably felt like the hardest part was behind them for now. It wasn't.
Infrastructure stress tests, it turns out, are the kind of problems you can prepare for. What was coming next had no preparation and no playbook.
It was, in his own words, the worst day of Tyler’s life.
On Friday, April 29th, 2022, Andrew Platkin, beehiiv's CTO, died suddenly.
There is no way to write around that sentence. Andrew had been there from the beginning, one of the four who had made the jump, who had sat with the others through months of nights and weekends before launch, who had carried the technical weight of everything the platform was built on. He was a colleague and a close friend.
“The profound sadness and emptiness that ensued was unlike anything I had ever experienced in my life. Andrew was brilliant. He was the kindest person I had ever met. He was our X-factor. And he was supposed to spend the next few years of his life building this thing alongside us.”
The team was left to hold the grief of losing someone they deeply cared about, and the impossible reality of a fast-growing company that could not simply pause while they processed it.
Losing someone that important after so many amazing milestones... it was painful. And no business playbook on how to be a founder prepares you for this kind of thing. The way Tyler dealt with the days that followed will forever be a ghost in his spirit.
“Mustering the courage to join our Monday all-hands with one less square present, and to lead the team forwards without him, was the most difficult thing I’ve ever done. It still haunts me to this day.”
How do you recover from having someone that important to you taken from you? You don't. You learn to live with it, somehow. At that moment, they did what they could with what they had, but it was extremely difficult.
“It was at a time when the platform was breaking for our users and causing them a lot of issues. He was in charge of doing some really difficult technical work to fix that. Navigating that for the next several weeks, when everyone was grieving, and everyone felt terrible, the platform wasn't working, things were breaking, people had to learn things that they've never done before on the fly, and the support queues were overflowing with complaints. It was a pretty miserable experience end to end.”
The team would eventually find its footing and see brighter days, but for now there was only the pain and confusion of losing a loved one.
Four years later, beehiiv has come a long way. But Andrew’s memory lives on.
To this day, Tyler keeps a photo of Andrew on his desk, where he spends 16 hours working each day. All day, every day, Tyler’s friend is still there by his side, watching over everything.
And he’s still helping when Tyler mentally says, “I think I f*cked something up.”
Andrew’s photo on Tyler’s desk. (Big Desk Energy)
To say beehiiv has experienced its share of challenges would be an understatement.
In the next and final chapter of our journey, we'll see how the team created a beautiful, lasting legacy to honor Andrew's memory, and how beehiiv kept growing, eventually gaining 100,000 new users per week in 2026.
But first, things would get worse before they’d get better.
Stay tuned.
