The Art of Strategic Storytelling: A Masterclass with beehiiv CEO Tyler Denk

Yeah, let's do it.

Yeah, I feel like you did a pretty good job with that introduction, so I'll try not to be too repetitive here. Yeah, I grew up in Baltimore, went to University of Maryland, studied mechanical engineering, self-taught software developer. After graduating, moved to my parents' house, couldn't get a job because the company I started in college failed and I was a self-taught developer with no internship experience. So started just building projects at home and that led me to meeting — I grew up with Austin Rief, who's one of the co-founders of Morning Brew, and they did not have an engineer. They had a lot of ambitious projects to build and was fortunate enough that he took a chance on me and I built something that worked. He gave me more work that turned into a full-time job and that turned into me being the second employee at Morning Brew. There I ran product, engineering, and growth. I built the content management system team for our writers to create the newsletters. I built the ad management platform for our sales team to monetize the newsletters. I built all of the ad creative, built the funnels, helped scale the actual newsletter. When I joined, we had about 100,000 subscribers, scaled it to over four million readers up into the acquisition by Business Insider. So my journey there, incredible experience.

And I left Morning Brew, joined YouTube for a quick 10-month stint. During my time at YouTube, I was really spending nights and weekends building beehiiv. During my time at Morning Brew, the impetus was we had received so much feedback from readers that they wanted the same newsletter capabilities that we had built. Whether it was the design of the template, the deliverability, the referral program, the growth mechanism, they wanted what we had. And as kind of the architect behind building all of that, I knew how to build it and saw that there was a huge gap in the market for everyone wanting to be Morning Brew for X, whether X is crypto, AI, business, politics. And I built a lot of that internal Morning Brew infrastructure. So me and my two co-founders, who were both software engineers at Morning Brew, left, started beehiiv in the summer of 2020, side project, nights and weekends, raised capital in 2021, and then as you mentioned, we're at about 35 million ARR today, should do 50 million in revenue this year, about four years into the business. And yeah, I do a little bit of product and founder marketing along the way, and I guess that's helped build the reputation that you alluded to earlier.

Yeah. I think Morning Brew stood on the shoulders of giants in the way — one, quite literally, the actual news outlets like The New York Times and Bloomberg and everyone that were doing the true journalism work, and then also The Skimm, which had come before us. And I think both Alex and Max took a ton of inspiration from The Skimm. The Skimm's target demographic were women, 20s to 30s, interested in news but didn't want to read the large articles, and they would synthesize them and make them more interesting as a quick skim, which is where they got the name from. Morning Brew took a similar approach, which is a lot of people are and should be interested in business news and pop culture and other things that are happening around and tangential to the business world. Reading The New York Times and The Wall Street Journal is very dense, and this new mechanism of delivering news, which was the newsletter — it's been around for a while, but I think The Skimm really normalized it in this demographic of you can spend five minutes and get everything you need to know in a single email. And so Morning Brew built on that strategy. So there's something around the format. There's something around the actual content, in which the way that they would describe it is they wanted to be like your best friend that was explaining to you what was happening in the business world. So it was very conversational. It was funny. It had pop culture references. It would reference some movie that just came out last week, but tie it into the Fed raising rates somehow. And they were very clever and creative in being able to create that content. With that, because they had such an interesting spin on creating that content, it built this brand affinity of people looking forward to and aligning and being proud of saying that they've read Morning Brew, which I think really was the tailwind for a lot of our growth. If you can build a brand that people actually are proud of and you can incentivize people to refer that newsletter to millions of other people, that's really what created that flywheel to help us scale quicker.

Yeah, we always used to say push versus pull. And pull would be expecting consumers to go to techcrunch.com and scroll down and find articles and read them. So you had to actually pull them into your ecosystem, which is the way that most of these media companies operated. The whole value of newsletters was it was push media, which is your consumers and your readers have to open their inbox every morning. They're using their inbox for work. They're using inbox for purchasing things and receipts and information and newsletters. And so if you can meet your reader where they already are and where they have to go, you're pushing content to them rather than expecting to pull them into your ecosystem. And I think that's something that a lot of media companies have obviously woken up to. So there's something around that. There's something around the conversational tone and adding humor into business news, which like The Wall Street Journal — I also read The Wall Street Journal, it doesn't make you laugh a ton. So like really being able to hit on humor and entertainment as a part of packaging this business news. And then I'd say the — and then brevity, right? Like the fact that two things: brevity and the reliability or like the frequency with which it comes. So it was habit-forming in that it shows up in your inbox at 6:00 a.m. every morning, and to be on the subway in New York City heading to work and being able to get a download of everything that's happening in the business world so you can sound smart around the water cooler with your boss or in a job interview and actually enjoying consuming that content. I think that was kind of the sweet spot across all of those vectors that made it work.

Yeah, I alluded to this a bit in my brief overview. Realizing now I maybe went into too much detail for my introduction, but yeah. So the thinking there was the amazing thing about newsletters is you can hit reply and you can get in contact with the person who sent the newsletter. And at Morning Brew, at the scale of millions of readers, we would have tens of thousands of responses some week. And one of our core advantages, which funny, there's a through line to like how I operate beehiiv today, is like always listening to customer feedback. I respond to everyone who tweets at me on X and posts on LinkedIn. Like that's where I get a lot of sentiment of like users and the ecosystem, but also how we can improve the product and how we build our roadmap. Going all the way back to Morning Brew, like we actually had the writers reading everything in the inbox because like that's how they got better. It was what story didn't resonate, what was too political, where did we have a blind spot in covering this topic where it didn't resonate with the audience. Eventually, at the scale of millions, we had interns reading through the inbox and they would basically forward to the right person. So whether it was the managing editor like, 'Hey, you took too hard of a political stance on this story,' and like a lot of people did not like it, and feeding that. But a lot of it was people who were either journalists or writers at other companies or hobbyists who wanted to build a newsletter, and they opened Morning Brew every morning and they saw the newsletter looks great, it's delivered well, like it's always hitting my primary inbox. They are clearly growing super quickly because they mention their growth numbers. They have this referral program which has incentivized me as a reader to share it with like my parents and my family and my friends. So they've clearly cracked this newsletter code. And a lot of these people would reply, 'How did you build the referral program? How did you format the newsletter? How are you rendering well in Yahoo and Outlook and Gmail? What data are you looking at to scale the newsletter?' And those questions would be forwarded to me, and I don't have the ability to answer hundreds of emails every day. But that was really the impetus and the seed of what we had built at Morning Brew actually was special. And the answer also wasn't, 'Oh, we use X platform.' The truth was we used X platform but built 15 things around it that are all custom to us. So where most of these readers wanted a simple answer was where did you build that referral program? They wanted me to say we use X, so just like a product recommendation. The truth was I built X and we've integrated with like five other things. And so that's where I think it became very obvious that what we had built was special and that me being the architect behind a lot of that had a lot of insight that could really productize this and bring it to a much larger market.

I think first step was realizing — well, first step was realizing what I had just explained and pitching it to Alex and Austin that like, hey, Morning Brew should sell this software. Like I've already done the hard part of building it once for us. Can we — right now our users are like the 40-person team, I'd like it to be 40 million people. We have massive distribution, why don't we sell this as a software product to them? The pros and cons, who knows, but like they were already talking about getting acquired by Business Insider, and I would imagine be quite the curveball to throw in mid-process in diligence that you're also a SaaS platform and going into a new market. So they were kind of like, that's a cute idea, but like we're not interested in becoming a SaaS platform. And then me and like my now two co-founders were all engineers on the team, and I think engineers want to build for millions of people. Like if you're going to put the effort in to build something, it's cool to have a few close people using it. It's much cooler to have a few million people using your software and benefiting from it. So we had always talked about like, hey, this would be really cool to productize. I think when I left Morning Brew, it took me one week. I actually got COVID the week after I left Morning Brew. And so I was actually stranded in my Brooklyn apartment with no job — not that I hadn't started my new job yet, but so no work to do. And I'm not someone who can sit still. So I actually just called my now co-founder, Ben, and kind of convinced him like, 'Hey, I think we should be building this company that we'd always talked about.' He thought I was crazy. He just spent three years building this tech. He's like, 'There's no way we can just build this, us two, in the next couple of months.' So we recruited a third, which is our third co-founder, Jake. And I convinced them step by step that it was a worthwhile endeavor, which kicked off 10 months of like probably the most high-stress 10 months of my life for a few reasons.

One, I think anyone who's ever had an idea, immediately after the excitement is the anxiety that someone's going to take that idea or that one of the other millions of competitors are going to get to market before you. For us, like the email space is massive. And our thesis was that we could bring a referral program which helps users grow, which was like proprietary to Morning Brew, but make that an add-on that came with the platform. And that was something that any of these competitors could have just launched a referral program because we talked about it all the time at Morning Brew. And that was like our initial wedge into the market and it would be totally gone. So for 10 months, we had this anxiety of waking up that any of these competitors would do that. The other anxiety is like me and my two co-founders, like we were co-workers. We're not like best friends. We're not totally aligned in life. They both got married fairly early and like priorities shift. So at any day they could have been like — Ben could have been like, 'Hey, I just got a promotion. I'm getting paid a ton. Like I'm not going to leave and start this company.' So you're kind of one foot in and one foot out where you want to spend weekends building it because that gets you closer to this. But then there's like half of you that's like, what am I spending my Saturday night building for where you have no customers, no revenue, and this could fall apart tomorrow. So you're just kind of on the edge always. And then I would say I immediately violated my non-solicit, my non-compete with both of them. And so I woke up every day terrified that we were going to get sued and just like basically —

With Morning Brew. Like I left Morning Brew and the next week I already called — like there was only three engineers remaining and I called two of them and tried to convince them to start this company. And so that ruined the relationship with Alex and Austin.

This is long gone, but yeah. No, exactly. I mean, and that was my worry. I was like, one, I know Alex and Austin are going to be super pissed at me, which they were, but I was like, that's actually not even their company anymore. Like it's now owned by a much larger org. And so like they might not even be the decision maker. So that was my mental state. Like I mean my mental state hasn't been all that great for the past five years, but like that was how it started, was thinking every morning that we were going to get either sued out of existence or that a competitor was going to make it totally moot to even build this, or that anything else could happen to make this reality not come to fruition. And that was a really stressful period of my life.

Yeah, for sure. So we started off as Morning Brew in a box. It was we want to be the best at newsletters. You can design a newsletter, customize it however you want, send it. We have tools to make you grow faster, which is the referral program that we built at Morning Brew built into the product, which was our core thesis. We built a recommendation network. And then the other thesis is, can we help you monetize? And this was really our big bet. What I saw up close and personal at Morning Brew was we had a team of 20 sellers talking to agencies and brands, which is how we would get sponsorships in the newsletter across our portfolio of newsletters. Then I looked at the ecosystem on Substack and on Twitter, and there's a lot of independent writers who are writing about sports and politics where they're amazing at writing about sports. They have no interest in talking to Nike to get a brand sponsorship, but like that's how they would be able to monetize and be able to scale their business. And so Substack kind of came into the market and normalized that the only way to monetize content is paid subscriptions. And I thought that was [__] from the beginning. We do it and we support it. And we actually are doing millions of dollars of transactions per month. And we don't take a cut of revenue, which is a big counterpositioning for us. As opposed to Substack and Patreon and most creator platforms that take a cut of revenue, 10 to 15%. We don't take a dollar from any of our users. So we support that. But I thought it was [__] that's the only way to make money with content on the internet. For decades, the most common way is through ads. But I knew that that sports writer or politics writer could not and should not spend their valuable time doing anything but creating content and definitely not doing brand partnerships. So the beehiiv ad network was always a thesis of can we do what YouTube did for video but for email and bring all of these brands. Today we have Nike, Netflix, Roku, HubSpot, like really premium brands that are sponsoring these newsletters, which in turn makes these newsletters generate more revenue, which means that they can invest that income into growing faster, into maybe going from a part-time project to a full-time project and then building and creating more content. So that was like our core thesis, which is let's do best-in-class newsletter software, help them grow faster, help them monetize more and not have this predatory take rate and let them generate revenue unopinionated however they want.

What we learned is a lot, and we learned this from the Morning Brew days as well. Morning Brew was such a well-oiled machine across all of these different product vectors. And so we gave users a newsletter product and they said, 'I want a beautiful website to host my newsletter, so people can discover it online. They can sign up.' And so we built a website builder and then eventually acquired a website builder that's now been folded into the product. So now you can create a custom website. You can go to my newsletter, mail.beehiiv.com, and see like the different types of customization you can do. So now we had newsletter and website. Then when you launched a website and people were getting traffic, people were like, 'Well, now that I have this website, I want to sell things. I want to sell a product, a course, a template, a guide, coaching.' And so we kept expanding the surface area. Where last year we launched digital products which allow you to do everything I just said. So you can sell your expertise online. Again, where most products charge a 10 to 15% take rate, we charge 0%. So it is more creator-friendly as a platform. And then as we continued to scale our surface area and users began to trust us — we build very quality product and we ship very fast. We listen to user needs and we're actually trying to solve their problems more than any other company, much quicker than any other company. That has allowed us to also ship podcasts, so you can host, distribute, and monetize your podcast directly on beehiiv. And then last week we launched community as well. So you can launch a full community where your audience interacts, engages, DMs with each other, messages in, hosts events, etc. So we've kind of evolved from like a newsletter-only platform to a newsletter platform plus this ecosystem of everything you would need to build a successful content business.

Yeah, super dumb term that I just named one of my newsletters, but it was around the thesis that a lot of these companies who are not media companies have invested in creating content, and everyone from Rippling, Chime, Plaid, Vanta are basically hiring like heads of storytellers. I think last December or last November, The New York Times wrote an article that Vanta is hiring a head of storyteller for $250,000. And that went viral on X of people like kind of ridiculing it and being like, what the hell is a head of storytelling? But I actually think it speaks to a much larger trend of going higher. I mean, the foundational labs are paying, you know, half a million. Really strong. Yeah. It's like it's crazy. It's insane. They're like staffing full, you know, owned media teams to — I mean, OpenAI bought TBPN, right? So for hundreds of millions allegedly. So yeah, I think they're investing in like the narrative and stories that —

They're putting out there. I think it's based off of a few different themes. One is distribution is becoming the bottleneck. Paid spend has continued to get more and more expensive across Google and Meta. SEO has been more commoditized and search is also decreasing and it's less difficult to break out from search. Social has evolved from a place where you used to be follower-based and if you had 100,000 followers, roughly 100,000 people should see your content, where now it's algorithmically based where you might have 100,000 followers, but maybe only 5% of those people ever see the content you post on Instagram or X. It's harder to reach your audience.

I think there's a thesis that people follow people, not features or faceless brands. And we see that, and the example I always give is like Brian Chesky at Airbnb. Like same exact launch announcement, one from the Airbnb account, one from Brian's account. And like all things being equal, like normalizing based on followers, he 100x'd the engagement because people actually want to hear from a person and Brian rather than like this faceless brand. There's this like confluence of like now that AI has become so prevalent, anyone that has access to ChatGPT or Claude or even like these video things can like create content that looks and feels good, directionally good. So there's a real premium on excellence rather than just like the slop that's being created. And then I think that also moves the conversation towards trust where it's you trust people or brands over just like any sort of like slop that's showing up in your feed. And when you put that all together, you can kind of see why there's a premium being put on quality storytelling, which I think founder-led marketing is like one of the many flavors of that, which is hearing directly from a person who has some sort of expertise who is doing content that's slightly different than you would be able to get from like asking ChatGPT or any of these LLMs. And so that's kind of like a long summation of like the thesis around storytelling. It's really just companies waking up to like in order to get in front of your customers reliably and build this trust and narrative, you have to be doing more than like the average. And like the bar has been raised with everything that I just mentioned.

Yeah, I think it's worth calling out that when I first started back in 2020, I I think I had like three or four thousand followers on on Twitter and like probably the same amount on LinkedIn. So, I didn't come from like a background of being a content creator and I still don't really consider myself a content creator and definitely not a background of like having a large base. Um, so obviously there's time and effort put into it. If I put more, I've actually just started taking it more seriously. I'd say even like the past like 18 months, if I had taken it as seriously as I am now maybe five years ago, I think I'd be much further along on this journey. I think it started when in 2020 when I was just building this as a side project. I started sharing updates of like features or things we were building or things that I was excited about building a company. And I just found this like pocket of Twitter that was like startup founder Twitter where people were constantly engaging with the content, like following along with that journey. And I think what that did was it was just like a reinforcement of, hey, we launched this and like 50 people would like it and they they showed some level of interest and they were responding. And so I had this like little community of founders. And then when we launched, we had 500 likes and people were engaging and super excited and signing up for the product. So I was like, okay, me sharing it like transparently what we're building and how we're thinking about the business has clearly caught the attention of other startup adjacent people and like we need customers. We don't have money. We just raised like a small seed round and at that point no seed round. And so I viewed creating content organically as an initial funnel to get people in.

I think since I've thought about it in like two buckets. One is altruistically, the content I create is extremely transparent of how we're building the business, how we're hiring, how we raise capital, how we run our meetings, how we do our feature launches. The thinking is I think a lot of founders are gatekeepers of what works. And I think the world's a better place if there's more people building things. And if there were more people sharing the secrets of how to scale a successful company, more successful companies will be created. And so I'd like to be a voice and someone who can actually share what works and what doesn't, hoping it inspires and helps other founders. So like that's the altruistic thing which is like very real and very legit. The other one is like as I create more content about fundraising, it's not just about newsletters, but it's about anyone who's interested in business or entrepreneurship and there's a very wide market of people and I believe in increasing the luck surface area. Like it is so hard to build a startup. The more people that I can have under my tent who knows about us and is vouching for us because they resonate with the content that I create, the better. And when they're at a dinner party and someone mentions that they are thinking about launching a newsletter and they can say, 'Hey, like I follow someone who started this newsletter company,' like you only get there by building goodwill and providing valuable content and helping others. And so we have got a lot of business from this founder marketing motion. And so it's kind of one, two sides of the same coin essentially.