Memes, Newsletters, and Millions w/ beehiiv CEO Tyler Denk

I graduated with $120,000 of student debt. I had no internship experience. No mechanical engineering job would hire me, nor would a software engineering company hire me. And I had like no money. I used to have a screenshot of like less than $3 in my bank account. Let's blow up the internet. From the basement to the higher net. Scroll and tap in there, we ain't done yet. Let's blow up the internet.

So you can make money with newsletters. Are you sure about that?

We're testing it. We're in the idea stage currently, but we're pretty optimistic about the future of newsletters.

But nobody opens their email, right?

Yeah, no one uses email. Nobody. But we think with the right platform, with the right type of design and creators, there's a chance that we may be able to get people to open more of their emails.

It's crazy, crazy. Yeah, I don't think anybody opens their email.

I typically scroll Twitter a few hours a day. TikTok after that, go back to Instagram. Most of my news is TikTok-based. The CCP, is that what it is? Yeah, yeah, CCP. CCP. Yeah, yeah.

And Chat CCP, which is DeepSeed.

Yes, yes.

So definitely newsletters, nobody opens them, you can't make money.

So don't start one and don't write one on Sunday nights 'cause no one opens them.

No one opens mine.

Well, isn't White Lotus on Sunday now?

Oh, true. Mine's Sunday morning, so hopefully people get to finish before.

Your what?

My newsletter.

Oh, you do that?

Yeah, yeah. A little thing, you know.

Yeah.

Only like 170 weeks straight, you know. It definitely always blows people's minds when they realize you can make money with newsletters, like 100%. Investors were confused, right?

We got told a ton no for a lot of reasons. I'd say one is the narrative that email has been dying for two decades now. That was also Slack's go-to marketing phrase, right? Like email is dead, the full New York Times or Wall Street Journal takeover. Actually, email is like the furthest thing from dying. I think any professional in any setting has to go to their email more than they go to anything else. Whether it's you're applying for jobs, you have a job, you're booking vacations, you're checking receipts, like the one constant in most people's life, which is a crazy thing to say, is that you have to go back and check your email for work or life or something. I think there is like a flood of new information and certainly people with cold emails that are extremely obnoxious, but Yeah, you can make a lot of money with newsletters and a lot of people are crushing it.

Dude, it's been insane. So I started my newsletter 3 years ago. You converted me over from Substack to Beehive. Something that I've always found super helpful that I've learned from you is when you're building a platform for creators to create stuff, creators, everybody obviously, but especially artists, we want to make more money. Writers, it's really hard for writers to make money. And so you could have either gone the Substack intellectual intellectual elite route for whatever.

We hate intellectual.

I know, dude, we hate them. We like meme lords. Or you go the route of we help you guys make more money. So I've taken a similar approach where it's like, you can make money with memes. This is not an art platform. This is a lot for meme marketing.

Right.

And I don't know. I think people underestimate how important that is, how much people care about that.

My thesis, just to jump in, is there's two things that our users care about. It is growing faster and making more money. And I think if we can build tools in a platform that helps you grow faster, and there's a lot of things that come with growth. Yes, it's a larger number, but there's also influence, right? People want to be seen, people want to be heard, people want opportunities. Being able to speak and send a message to more people is influence, it's power, it is an opportunity to make money in the future by having more people on your list. So growing faster and obviously making money, bottom line. How can we have them pay back what they're paying us if they are paying us? How can we have them earn revenue to reinvest into other channels, other business units, whatever it may be? But I think that's something that I've known very early on, two things that people care about. There's a lot of inputs prior to that that you have to do well, right? You have to create good content, you have to have a strategy, you have to have a target audience that resonates with what you're building. But at the end of the day, numbers go up is really what keeps people around, and numbers, growth, revenue.

100%. And people underestimate how important that is. It's the reason why Beehive's killing it. Last year, my newsletter, it took a few years because I started when I was 21, 22, scrappy, broke. And as I've grown it way past 6 figures last year, with the mix of ads and community and all sorts of stuff. And it's crazy. I remember how stupid people thought I was for writing a newsletter every week. And for the writers out there, you're gonna look like an idiot when there's only 100 subscribers, right? Or there's only 1,000 subs or you're not making money and it's like, what the fuck is the point? It's like, no, this is for you. It's a long haul investment. And my newsletter has taken me crazy places. It's taken me here, taken me to conferences, got me hundreds of thousands of dollars of customers, right? And like helped me build my software. The newsletter is like the home base for everything. And I don't think people, everybody realizes that yet.

I also think newsletters went mainstream-ish. Like there's plenty of people that came before Morning Brew, but like a lot of people look to Morning Brew, The Hustle, Skimm, Axios, and they see massive newsletters with a huge audience and advertising base. And so for, I think a lot of people getting started, they feel like there's a very high bar of, I can't make money till I have 50,000 subscribers. We have newsletters that are in single-digit thousand subscribers bringing home $100K+ from events, sponsorships, community products, just using email as top of funnel. There's a lot of very niche applications and use cases for it where you don't need, for example, this trip that I put on is technically, I guess, revenue from the newsletter. That's how I source most of the founders. And I could have had 500 founders on my email and generated tons of revenue from this. So— 100%. Which also should we— where we are? Why we're not in this beautiful studio? Yeah, oh yeah, shit.

We are in Costa Rica right now. We're at Tyler's retreat, big desk energy.

What do we think so far?

Dude, it has been an incredible time. It's like 6 other founders, I think. We've done like presentations, introductions. If you're ever thinking about A, going on retreat, go on Tyler's, but if you're ever thinking about hosting retreat or events, something that I really like that we've done so far, speaking about events, is like the introductions have actually felt almost like a podcast episode where instead of doing stupid icebreakers for 5 minutes where you learn nothing, we each did introductions for 45 minutes over a span of 4 days, basically 3 days. Just like the deepening of connections. It's almost like reading somebody's newsletter for a year or something.

Everything ties back to email, dude.

Everything goes back to email and memes. That's it. MemeHive. But yeah, I think It's insane how many different ways you can make money with newsletters. Like you said, even when my newsletter was low, I was still making great money from it. And now it's growing more. I think local newsletters are untapped. Dude, it's insane.

Every time I go on Twitter, there's someone else who just launched a local newsletter.

I know, it's crazy. It's wild. Because you get all these small businesses, you start throwing events, you become like a celebrity in your city. It's crazy.

We gotta go back to the mastermind topic.

All right, yeah, yeah, back to masterminds.

How we even ended up here is one of my buddies who I met in Medellín introduced me and was like, hey, we're gonna host this mastermind event in Santa Teresa, Costa Rica. 4 days, 6 other founders, we're gonna surf, we'll do yoga, we'll do sound bath, and we're just gonna talk business. I honestly just wanted an excuse to go to Costa Rica and surf. I saw the house, the Airbnb, I said, I don't know any of these guys, sign me up, I trust you. Yeah, kind of like a life-changing experience in the sense of I've been heads down building for the past 3 and a half years, don't care for networking events. It's like, not— there's value in them, but it's an inconvenience. A lot of the networking events are standing around a bar awkwardly introducing yourself into some conversation, talking about what you do, seeing how transactional of a relationship it can be. Can they introduce you to someone? Can they help you? If not, move on to the next person. And if you're not playing that game many of the other people in that room are playing that game. And so for 4 days we were in Costa Rica, we were chilling, we were like on the beach. It's not forced, it's not a conference, there's no itinerary. And then one day we sat down for lunch and we like, most of us didn't know each other. And one person was like, so this is my background, this is what I do, this is where I'm struggling with my business, here's where I think the opportunity is. And when you have the right group of people, the other 6 people listening to that were like, oh, you should try this software. Or like, I have a buddy who's actually solved this exact problem, let me introduce you to them. And like we talked from lunch to dinner to drinks. We sat down at this restaurant, this like beachfront restaurant for, I kid you not, 6 hours and just did intros. And it was like the least transactional, like questions ranging from how much revenue you doing to what are your long-term goals with this business? Or like what are your long-term goals in life? Like do you want to be a public founder, CEO? Do you want to do this as a launching pad for something else in your career? And for 6 people I didn't really know at all going into this trip, left that 6-hour sit-down knowing them more than almost anyone outside of my best friends. So that's kind of what laid the foundation for doing this. And then I've wanted to come back to Costa Rica. I wanted to meet other founders. I launched a newsletter and like, same thing, going back to like the previous conversation of how do you make money with your newsletter? I'd be like, I could just do ads, which I now do ads. But at the time I was like, I have 25,000 mostly founder, early startup people reading this newsletter. Let me just aggregate 6 or 8 of the most interesting. We go to Costa Rica and everyone gets to meet other people.

Yeah.

Anyway, that's the backstory of this. It's been amazing. This is my third one. Glad you're here and we're having a great time.

I mean, I don't know if you're comfortable. If I need to edit it, you need to edit it, but dropped 10 Gs to be here, which is a lot for a bootstrap founder.

Don't edit it. Price is going up.

Price is going up.

All right.

Dropped 10 Gs. Already worth it in my opinion. The presentations that we've done, everybody's done, like Tyler showed us the inside of Beehive from like the weekly flows that he does with his team, the entire framework. And you know, I'm a solo founder and first time kind of thing. Like it's so helpful for me so far. And then I showed like my software and people already gave me more ideas. Got, dude, just inspired.

Like, dude, you have like 6 other founders who are so high agency watching you use your software and be like, this is where we get leads. This is where we like do that. And Someone's like, yo, have you tried this automation? You're like, no, let me write that down.

Also just the inspiration. I don't know if I told you this last night, I was just feeling inspired. You know, I love to say you could just do things, like we're always saying that shit, but like last night I've been thinking a lot about this idea of secret agents, so A-I-G-E-N-T-S, and I've always been like a James Bond fanatic, right? Like loved it since I was a kid, my dad showing it to me. And last night I was like, you know what, Dharmesh Shah, founder of HubSpot, billionaire.

VIP user.

Yeah, yeah, dude, he fucking subscribed to my newsletter like 3 years ago. I never reached out to him. I just like, you know, never had much to say. And last night I was just inspired being around people like this, like just inspiring. So I cold emailed him. It's like, yo, I got an idea for Agent AI. Like the branding sucks. Sorry, Dharmesh. The branding sucks right now. Like I didn't say that, but like I think it'd be really cool if you do this secret agent thing.

I don't have time.

I'm full-time on Memelord Technologies.

Like, but I think— Respect, respect.

Yeah, but I think this would be sick. 3 minutes later, signs up for my software. 3 minutes later.

It's also crazy 'cause like, he's a Beehive user actually, and so we've emailed back and forth. It's something that a lot of people say, which I think I'm very good with my emails. I'm inbox zero every single night and try to be responsive as possible. I also go on the other end of the spectrum of like deep focus time, don't wanna touch email or Slack for 3 hours and get shit done. He responds within an hour every time. It's so impressive.

It's insane. It's the same thing with like somebody like Mark Cuban or whatever. I mean, you have to be super responsive to be successful, so it makes sense.

I'll take a step back. You have to be interesting to get a response. People, I put my email freely on Twitter, LinkedIn, whatever, 'cause when people are like, "Hey, I need help doing this," I don't need to bullshit around, file a support ticket, just email me directly, I'll triage and solve it. So then I have that relationship with our user, and people are like, "Why do you share your email?" You can get my email, it's tyler@beehive. I will read your emails. Will I respond to your emails? Maybe, if it's interesting, right? And interesting varies from, It's not like, I can make you more money, this is like a huge opportunity, 'cause like the higher lift or higher effort it is, the less likely I am to do it.

Dude, he's a billionaire.

Yeah. Like, you just said I'm building something cool and I have this idea for you, so like, hi, Jason, you're showing interest and you're like, I'm actually building this other thing and it's like catchy and he's like, I can sign up and pay $6.97.

No, no, he signed up for the big $42 plan. He doesn't have a micro—

That's also, that's the life hack to growing a business. Just sell to billionaires.

Obviously. Also, also, sell to VCs and then don't raise VC. So I took like 3 or 4 VC meetings even after I knew I wasn't going to raise, just have them sign up.

I was like, that's good. Yeah, it's kind of like if you're ever applying for a job, one, common sense, sign up for the product so you can speak to the product or whatever. But if you want to show going above and beyond, pay for the product and use all the features. So it's a no-brainer. If you're going to go into a VC meeting, they should probably— they're unqualified if they're not going to sign up for the product. Honestly, I said that. I said I'm not going to take the meetings.

I literally said that because I wasn't that serious about raising. So I was like, why not? That was a crazy experience thinking about raising and that entire thing.

When did you consider raising?

This was like 6 months ago when I was first starting out, and it was cool. I went to talk to the team at O'Shaughnessy Ventures. Jim's the fucking man. He is a legend, like hilarious meme lord. This dude is 75-year-old billionaire kind of guy, and he's read my book and we became buddies, and he gets it. He gets it. So I talked to his team and they were the first people that I was like, I had already talked to him before and they were super interested. And I pull it up and the coolest part, this was accidental, but I pull it up and there were already like 10 people making memes on there at the same time, which was crazy during a VC call. That was some big dick energy.

Of course.

And so they're super interested. And for me, I decided not to raise. I enjoyed doing it by myself.

So is it lack of control that you want to give up, which is why you don't raise, or is it you don't need the money or you have enough revenue now that you don't?

I don't need the money. And what I, you know, I kept talking to different friends, like I talked to Alex Lieberman, right, early on, and he was basically like, dude, you don't have enough data yet, like wait another 6 months.

And I'm very glad. Also controversial, sometimes the best time to raise is when there isn't data, because then you get into like data-driven investors. Not that there's anything wrong with that, but my thesis is like early stage, pre-seed, seed, you're betting on like the founder, the team. Not that I'm like an expert investor, I've done a few small seed checks that are like too young to even see if they'll work out, but From my experience, there were so many investors that said no to Beehive because there wasn't enough data, there wasn't enough convincing data, or they were looking at other data like size of market. Dude, there was one investor that reached out being like, what do you think the total— he kept nailing down the total addressable market. It's TAM, it's TAM. And first of all, TAM doesn't exist.

It's the stupidest metric.

But there's people who send emails, there's people who have a blog, there's people who have websites, there's whatever. Podcasts, creators. You can go in a million different directions. So obviously when building a slide, when I'm trying to build the business, I pull a few random reports pre-ChatGPT time in 2021. I throw up a random number that is just big enough to be exciting but not too big where it's unrealistic. And this one inexperienced, annoying fucking investor kept drilling on like, what do you think the TAM actually is? And I kept— I was like, I don't fucking know. And that you shouldn't be investing in a seed stage company if that's what you're worried about.

Yeah, 100%.

Mailchimp sold for $13 billion. There's a market there. I don't need to answer your question.

Yeah. So anyway, it was like I hit profit very quickly because it was cheap to build and I built it myself.

By the way, shout out Bubble.

Yeah, shout out Bubble, it's crazy.

You gave the demo of what the platform looks like from the outside and inside and I can't believe that's possible.

Yeah, it was a lot of work, very, very tedious, but it works and it makes it easy. You said you showed the Bubble team and they were like, "What's your Adderall prescription?" Yeah, dude, I was drinking coffee doing this demo, they were laughing their ass off and then the next person comes up and it's just some boring doctor stuff. I was like, hell yes. Anyways, yeah, so hit profit fast. I was like, I don't need to raise, I'm not gonna do it, I'm in control. But I wanna jump into something else while we're talking slides and stuff. So slides. Yeah, yeah, so something Tyler does, at least showed us yesterday and today, getting my days crossed, but with slides that he makes for his team and There's a lot of people have always talked about Bezos's memos and how important it is to write, and I believe that 100%. So how do you think about internal communications for your team, inspiring them, like a mix of slides? And I'm not talking about pitching VCs, fuck that. I'm talking about pitching the teams with, or talking to your team and inspiring them with a vision and strategy.

Yeah, it was kind of what I said the other night. I think my number one job is storytelling. There's a lot of things I do. I do product, I used to do engineering, I work with design, I hire, fire, whatever. But at the end of the day, my job now with 85 employees is to storytell and be able to communicate what I think we're building is massive. I think it can impact a lot of people. I need to motivate everyone from my co-founders who don't need the motivation, but from the last person that we hired at number 85, to be as equally motivated and driven to continue to build on what we're working on. There's a lot of different ways to do that. For me, I'm like, I have a million thoughts and I need to get them into a slide deck and I need to show them what the opportunity is and how it impacts everything. I think repeating things is extremely important. Everyone's so busy. We're a remote company. People who are working on the ad network haven't engaged with people who are working on this automation feature who isn't working with design. It's like there's natural silos, which is good and bad. There's a lot of focus, and— but because we are remote and we're not bumping into each other at lunch every day, like, people focus on what they're working on and lose sight of how it impacts, like, the broader business. So I actually think a big part of my job is to be able to connect all of the dots. And you saw, like, my weekly success list. Like, it's— there's, like, 25 things on there that, like, I don't expect anyone else at the company to have to keep tabs on each of those 25 things. But like, that is my job to show how this person's effort, it leads to the success of this team, which leads to the success of this initiative, which leads to the success of the company. Um, so storytelling is super big for us. We do a quarterly review of like reviewing the previous quarter, a preview of the upcoming quarter, and then like big tentpole features, like highlighting different users. Um, I try to keep it fresh and try different things. On Valentine's Day, my girlfriend wasn't happy with me, but I was like— and you saw a sneak peek of this presentation. I will keep it private for now, but I was so inspired by something that transpired that week, and I was like, I have so many thoughts. And Valentine's Day was on a Friday. I just spent all Friday night working on this presentation that I'm going to present tomorrow. But basically, like, a big opportunity that I think we have, and like, going back to you can just do things honestly pretty awesome to think about that I was inspired at one point from like whether it's a podcast or something I saw on Twitter to be like, oh, we can shift our focus and do something different here. I can spend 4 hours creating a presentation to communicate my vision to the team. I will present it tomorrow. I think we will act on it next week. And then we are off to the races and like launching a totally new vertical. I think it's incredibly cool. And like, that's another benefit of being a startup that like we can just do things like that.

It's ridiculous. I love the— I was initially actually very against having employees, and then I found the employees that were right for me, I guess, or they found me, which makes sense. They're super high agency, right? And you actually tweeted the other day, it was like, what do you think the number one skill that we're going to teach our kids is now that AI is here? I really just believe it's agency. It's like, how do you teach kids that can do shit by themselves? They're not getting babied. They don't have tiger moms. Like they are doing whatever the fuck they want. You know, for me, like I started selling stickers when I was like 14, made like $40 grand in high school just like selling stickers on the internet. Like how do you raise kids like that is something that like, now that I have a wife, like think about shit like that. But yeah, the point is like agency, super important and having a team that is high agency where you could tell them like, okay, you do this. But even better than that, what I realized was like, oh my God, they're suggesting ideas that I would never think of. Like, oh my God, this is crazy. And then, dude, at first, this is gonna sound weird, but I had 2 employees and they didn't know each other 'cause like we were working on separate things. And I was like, should I introduce them? I was like, ah, maybe I should. And then they started coming up with ideas and without me there, I was like, oh my God, this is incredible. And now I have like a sales guy, Cam, who's a fucking man, and he's just fucking grinding sales and I'm not taking sales calls. I was like, what is going on? He's like, oh, leverage. It's leverage. I don't know, it's been really interesting. Employees, we were talking about this, people problems, right? And for me, having as little people problems as possible.

You've seen me on my full 360 trajectory over the past 48 hours. So I listened to a podcast, I've written a bunch about this, but listened to a podcast that put it so clearly to me this past week, Invest Like the Best, by the way, great podcast. Um, and so they were talking about how as the company grows, it's natural that the CEO and founders and leadership are spending less and less time on problems for the customer and more and more time on other problems. Other problems: employees, hiring, processes, performance reviews, check-ins, one-on-ones. None of those things— I mean, indirectly, yes, but none of those things actually solve the problems that our users are having today. Users want better features, more monetization, they want to grow faster. There's things that we could be focusing all of our time on. And so when it was just me and my two co-founders, we were 100% focusing on the customer. There's nothing else to do. We don't care about our titles, we don't care about compensation. We are— it's us against the world. We think that no one's giving us a shot at building this. We believe this thing should exist. And we are just 100% focused on shipping and whatever the customer asks for. Then you start adding people and now we're at 10, then you're at 20, then you're at 30. Now you need one-on-ones and you need recurring meetings and someone wants more responsibility. Then someone wants like a title change, then someone loses interest and then someone leaves. And so your time, my time personally, and our time as a leadership team goes from what was 100% on the customer and the product to maybe it's 50/50 now. And I'm not great at hiding my emotions. Like I get really frustrated when I'm like, this is what's actually important and you're taking me away from doing what actually matters at this company. 'Cause the competition doesn't give a shit that you want a different title or you want to change your role. The customer doesn't care that we have this recurring meeting that's preventing us from shipping the features that they're asking for. And so that's something I'm super cognizant of. And so I bitch and complain about that all the time. One of the things I'm trying to focus on is how do I get as much of my time focused as close to the customer. But then on the other end—

You're excellent at that, by the way.

I would say on the other end of the spectrum, to your point about how employees are also awesome, On this trip, I took off yesterday and we were like doing intros, we were doing sessions, we went surfing in the morning. And so like I was kind of phone away for like 8 hours. I came back like a proud parent and like so much shit got done yesterday, like so many initiatives. So like it's the highs and lows. Like I love our team, they're so talented, they're so high agency. So it's not anyone in particular on the team, it's just the nature of a startup and a company as it grows, there's just more shit. But the flip side of that is like when you have the right people, like, We had one of the most productive days ever yesterday. I didn't touch my phone once. That feels incredible.

It's the nature of humans just being together. And so what you were talking about yesterday actually inspired me to tweet basically like everybody talks about small teams being small and mighty and you could save a ton of money, right? Because you have a small team and now with AI teams are potentially getting even smaller. But not just that, saving money, you're saving people problems. And a lot of founders like myself, we are fucking weirdos who are kind of maniacs on the internet and we I spend a lot of time alone and just like creating weird shit. I don't want to— I don't like talking to people that, that much. Like, I don't— I'm not good with like that shit, right? Like, I'm good, but I'm not like— that's not what I enjoy. Like, I enjoy like making shit.

I enjoy writing.

I enjoy like, you know, writing a script for the show that I'm working on. Like, that's what I want to spend my time doing and like building the software. And as AI improves, like, yes, like your company's also becoming more profitable, but also less people problems, less crap, less crap to deal with, less baggage. And so being a founder right now is fucking beautiful. It is incredible. I'm using AI to build these automations, getting signups while I'm on the beach in Costa Rica. Life's good, right? And so it's something that I'm trying to be careful of, maybe overhiring or just keeping the team small. Do we need this?

Small teams are sexy now.

Dude, small teams, I feel like small teams are sexy.

I don't know why, I don't know who put the idea in their head of like, every now now and then I'll like— and this isn't like supposed to be a brag— it'll be like, I can't believe we're 80 people or whatever on LinkedIn, or like something. It'll be like some cool milestone. The point of that wasn't that we're 80 people. Like, that's like not the great part, right? But like, there was definitely a time and place where founders felt like success was having a larger team, and it stemmed out of like, I don't know, like a power struggle. I have no idea why that became cool. To me, it's been the opposite. I was like, can we build this for 30 people? And then as you grow and like things happen, you're like, oh, we could use a little bit more engineering, we could use a little bit more here's a really cool opportunity. And very quickly you start to see how one hire leads to multiple hires. So it's like we could use more engineers, like, so for example, let's say we need one additional engineer. We hire one engineer. Now we have so much engineering bandwidth, we're actually blocked on design. So we need a new designer to hand off mockups to engineering. So now it's two hires. Then we're actually shipping faster and there's more bugs and input coming in, so we need a product manager to take— product's kicking, now we're growing faster, we need another customer support agent, we need a customer success manager, we need another salesperson. And it's like that one, it's kind of like the domino effect. Domino meme. We could just probably do the whole podcast in memes, but like the domino meme, that one or two engineers that you hire just led to like 6 additional hires that you weren't anticipating, but everything's so interconnected. So not that I've fallen in that trap a few times, we're 85 people now, I'm happy with the team size.

His domino meme, Tyler's domino meme is raise a Series B, raise $30 million just to pump a Spotify playlist.

You should check out the Spotify playlist.

Big desk guy.

Hopefully it's a soap opera, I think.

Yeah, I think it is. I mean, it's the same thing. You found a company and we all, it's not all about the company, right? I have crazy other dreams. I've learned a lot about you this trip, learning about, oh shit, you're super into spas and wellness and you're thinking about doing stuff there after Beehive or whatever. I don't know. You start a company and there's a ton of dreams and it's pretty fun to be able to, for me, my domino is build the software, start a show, do podcasts, all sorts of shit.

Yeah. I feel like everyone kind of has that trajectory. I mean, I'm like laser focused on BI, but I think there's like, of course, but like, so it's actually like more of a meta thing that you kind of hit on of building the, it's kind of like the employee and the people and the shit and whatever else. And something I've been pushing back on, one of like going back to like, where do I spend 100% of the time focusing on customer problems? There is like this acceptance that as a company grows, you have more recurring meetings, more one-on-ones, not just away from the customer, but like they're not enjoyable. And so I listened to a podcast, The Founders Podcast, about the NVIDIA CEO, and he has apparently 60-some direct reports, zero 101s, and he's been running the company for 30-some years. And the takeaway from the podcast host was if he wants to stay there for 30 years and actually enjoy what he has to do, he has to build the company that he looks forward to building. And it's such an obvious statement, but I was adding 101s, and I have 10 direct reports, and we're doing weekly 101s, and I'd wake up Monday morning and look at my calendar, like, I generally— we don't do meetings Tuesday and Thursday. Monday, Wednesday, Friday, very meeting heavy because we don't do meetings Tuesday, Thursday. Monday, Wednesday, Friday, like, I actually like— I'm like, I'm not excited for the day because I just— I'm gonna sit in meetings all day long. Yeah. Tuesday, Thursday is heavenly. I love building. I love putting my headphones. I love going heads down. I was like, me just saying that out loud is like a problem. Like, that's 3/5 of the week that I kind of don't look forward to because they're heavy with meetings. So like, what's better for the company, these recurring meetings or me as the founder being motivated, happy, and enjoying what I'm doing. And it's clearly the latter. So I canceled all my one-on-ones, moved them to monthly, removed like 10 hours of meetings from my calendar. And I feel so much better. I think that was just like such an obvious choice to make, but like it took me to hearing how someone else was having success and like breaking like the paradigm of like what is normal or like what is expected at like a Series B company, which I hate all of those. I hate the common truths, the acceptances, like this is just how things are done. Like, I don't agree with like 90%.

Dude, I mean, I have basically no meetings and it's amazing. It's mostly Looms and I want to spend my time like just creating shit, right? And it's relaxing. It's weird because like I love my team and I want to like have these meetings.

Like, I actually feel— I'm on the other end of the spectrum. I actually feel bad because when we were 20 people, I would talk to like all 20 people every single week. There's probably a handful of people in the team I haven't talked to like too much just because like we don't cross paths as much. And so like on the complete other end of the spectrum, being counterintuitive, like I wish I had more time to be able to reach out to them, be like, hey, do you just want to catch up and chat for 15, 20 minutes? Want to check in? So that is like the constant balance of I want to spend time doing what I care the most about, which is product engineering, design, and just building and solving customer problems. But I also am the manager at the company and I'm a people person. I'm an operations person. I need to check in and make sure people are taken care of. So it is like a very difficult balance. I'd say.

Yeah. Something I think, talking about getting close to customers, Tyler's crazy good at this and learned a lot is I got recruited over to Beehive 3 years ago from Tyler just DMing.

For free, we didn't pay him.

Yeah, yeah, no, just DMing me, right? And the amount of signups that I've gotten just from DMs and cold DMs and cold emails is insane. And becoming homies with your users is such a good feeling because you're just like, Building stuff for your friends. It goes from building stuff for a random big-ass person to like, oh, let's jump on a call. You want me to fix this bug? Or let me send you a goofy meme, goofy Loom. When I fix bugs for my software, I go in there and I always leave a hidden Easter egg meme for the person's account. And it's just fun. Staying close to the customers is really important. I think there's a very YC fucked up those words of talk to your users. You're not supposed to, in my opinion, I think you don't talk to your users before you launch the product. A lot of these founders, it feels like they're like, let's go talk to construction workers or construction tech and figure out a problem. It's like, no, you build the thing and then you hang out and—

Or even better, you are your user before you launch the product, which I think goes back to what you're saying. It's easy for you to talk to your users because they're a bunch of nerds who love memes.

Yeah. That's you, right?

That's exactly what you want. For me, it's easy to talk to my customers 'cause they are trying to do the same thing that I'm trying to do. They're trying to build things, they're high agency, they are creating content, they want to scale their audience, whatever it is. From my Morning Brew experience, from now with Big Desk Energy and the newsletter, we're almost at 100,000 subscribers. So I am the user, which helps. And then when people, which is also a superpower, by the way.

Such a superpower, 100%.

When I go to write my newsletter and something doesn't work, I am like, I'm in every Slack channel, like, "Why doesn't this work? Why is this broken? This makes no sense." But it's actually, I would say, a huge superpower of the team. It's not me alone. We have, I'd probably say, maybe 2 dozen people at the company that have—

Steve, Daniel, everybody has a newsletter.

Steve has like 11 newsletters. But yeah, the fact that they're power users, yes, you can file a support ticket. It will get escalated appropriately. We actually have a Slack channel with our users and they'll DM me and be really annoying, but it's fine. We'll talk about it. But our internal users who are power users and are in the meetings with the people who make decisions are like, "Hey, I've been trying to do this in the platform. Doesn't make any sense. Very unintuitive." We fixed it in 2 hours. So having half the company with a newsletter is an extreme superpower. That's where I prefer to hire from. We've hired a ton of our users just 'cause there's a non-negligible amount of people who used to just be very annoying users who would just constantly DM me and be like, "Yo, when are you gonna build this? When are you gonna fix this?" Hey, I'm still waiting on this feature. And a few of them just turn around, they're like, do you need help over there? 'Cause like I can do some of this stuff. And like it's the things that no one else was owning at the time. I was like, dude, just come on over. And like they know the product inside and out, it's been super helpful.

100%. Like all my meme team, my meme lawyers are all on the software. I'm on the software all day. Like that's how I know what to fix and how to fix it. And like building a product for yourself, like something really, I wanna say like, feels like a caveman. I've been thinking about this, almost like caveman building himself a hammer. I built Memelord for myself because I was pissed off at the other platforms that existed. And same with Beehive, right? And it's like you get to build yourself tools. It's a cool feeling. And then you just make it better and keep adding cool shit, then become tools for everyone. It's a fun feeling.

Name of the game.

I want to talk real quick, dude, something I didn't know about you. Was 22, you were broke living in your parents' basement after college, figuring shit out. There's a lot of college kids that listen to my podcast or read my newsletter. Any words of advice for people trying to either break into startups, start their own thing, or what would you tell a younger Tyler?

Yeah, honestly, high agency is everything and just sticking with it. There's no better time not to be a fuck-up, 'cause I wasn't a fuck-up, but to like not have it all figured out than like when you're young and like have plenty of opportunity ahead of you, right? It's much harder to make the leap and get out of like corporate America, the incentive structures, like whatever, when you have a family, kids, wife, mortgage, whatever. For me, I launched a startup in college my sophomore year. I didn't have an internship for any of college because all of the kids in mechanical engineering had like these different internships. And they were like, you going to the career fair? I was like, dude, I'm building a multi-million dollar startup, bro. Why would I ever go to the career fair? And so I almost like looked down at these people because I thought I was going to like this massive like unicorn startup. Newsflash was not a unicorn startup. And so I graduated with $120,000 of student debt. I had no internship experience. I was a mechanical engineer who's never done any mechanical engineering work because I forewent doing any internship. I was a self-taught software developer also with no experience because I was like building my own startups. Like I'm my own reference. So I was like the worst, like I was the least— I think no mechanical engineering job would hire me, nor would a software engineering company hire me. And I had like no money. So like I used to have a screenshot, like less than $3 in my bank account. Moved back to like outside of Baltimore County where my parents live, like living in the basement. Student debt loans were like picking up in like 6 months. $2 unemployed. I taught myself how to build Shopify websites. I like, I guess I don't know when Shopify started, so I felt that I was early in 2006. It was pretty early. I saw the vision for Shopify and obviously there's a lot of similarities between what Beehiiv is trying to build and like democratize is overplayed, but like a platform to be able to build online, monetize, grow your audience. For them it's like selling goods and whatever. But I saw the power of Shopify back in 2016 when I graduated. I was like, this platform, if I had more than $4 in my bank account, I would invest every dollar I had into that. So I got really good at building Shopify websites. I built a Shopify website for my grandfather's like basketball store, like shoe store or whatever. And I started doing like weird like freelancing projects. This one guy gave me a chance from like this community I was in to like build WordPress websites, which was like the worst. And I was so underqualified but so stressed out and was just like building and tinkering. And then on my way home from Washington, D.C. one evening, I was catching up with Austin Reif, who is the co-founder of Morning Brew. And he was like, dude, like Axios and The Skimm have like this referral program that leads to like so much growth. And like all of them have this like You can click on the bottom of the newsletter and share to Facebook and Twitter, which now it's everywhere. But at the time it was semi-novel, I suppose. He's like, we don't have any of that. We don't even have an engineer. He's like, do you wanna build this? And I was like, yeah, how much? He's like, 3 grand. I was like, dude, no problem. I got you. I had no idea how to build this. It was shitty WordPress, PHP, custom code. This is pre-ChatGPT days. ChatGPT would've been amazing here. And so for 3 weeks I bullshitted him. I was like, yeah dude, we're almost done. I was up till 3:00 AM for 3 weeks. I almost quit almost every night.

Wow.

That's wild. Because it was a perfect example of, I'm sure there's a way that I knew I could have figured out to do it and I did, but I was so unqualified and just lied because I needed the $3,000. And then once I launched it, he goes, "Dude, we have 20 things that we've been wanting to do. We just don't have an engineer to build it. Do you just wanna keep doing this?" And I was like, "Dude, of course. I would do whatever." That led to eventually a full-time job at Morning Brew and the rest is history.

Dude, it's crazy. When you're young and hungry and desperate— Yeah, desperate's 100% the word. You do anything. I, so when I was trying to like break into the Twitterverse of like ghostwriting, like I just wanted to get money for writing. Like that was my dream.

Like fuck yes.

And I get on a call with Greg Eisenberg. Like he, you know, we DM and this is like very early. I have like, you know, 1,000 followers at the time. I'm like still just starting. He has like 200,000. He's like a fucking celebrity. And he, I'm working, you know, my job at the time, data engineering shit. And he's like, wanna hop on a call tomorrow? We're working for Warner Music on a pitch. Wanna just jump on and jam all day?

And I was like, yeah.

I just took off from work that day, jump on with him. We're on for 3 hours and I spill coffee on my laptop. Laptop fries. I'm like, as it's dying, I message, I'm like, yo, gotta grab lunch. I book it to the Apple Store. Buy a laptop, you know, like credit card, like I'm broke, like buy a laptop, run back, jump back on. And like he never knew, I told him after 'cause we're homies, but like he had no idea. Like you just do whatever the fuck you gotta do. Like I knew it was like an opportunity I wasn't gonna fuck up. So you do what you gotta do. Like, I don't know.

The one thing I'd say to piggyback on my story around like what advice I would give, the more clear advice is betting on yourself. Yes. Because what I left out of that story is towards the end of that summer, so I graduated in the winter, I worked freelance, lived in my parents' basement, super broke for 6 to 8 months working with Morning Brew. Funny story, I went up to visit New York. They hosted a happy hour one day. I was catching up with Austin. He's like, dude, I think we're going to hire an engineer from Facebook or Google. Meanwhile, I'm freelancing as their engineer. I was like, I guess they don't want to hire me because I'm definitely not that. I'm a self-taught, super insecure software developer that doesn't really know what they're doing. When they eventually offered me the job, they were 3 guys working out of a closet. Newsletter company, 100,000 subscribers, like very risky. Also got a job with Deloitte in DC to do like technology consulting, nice $75K salary, secure benefits, health insurance, everything. Again, I have $120,000 of student debt. I've been living at home entirely broke for the whole summer. And so unproven startup that I at least have like the ability to change, or Deloitte in the system, sure thing, but like pays the bills and covers my student debt payments and everything else. And I was on the phone with one of my friends, different Austin, and I was like walking through it. I was like, dude, it's like so uncertain. He gave me like one of the best advice ever. He's like, you could be one of 50,000 technology consultants at Deloitte or you could be the only person in the world building Morning Brew. I heard that and I go, no brainer. And like just bet it all on that and like totally changed the trajectory of my life.

Dude, betting on yourself. I've never, never regretted investing in yourself. Something my dad taught me early on was like, you know, anytime I'd ask for a book, he'd say yes. Like, I didn't ask for much, like video games. Like, I wasn't a big video game guy. I wasn't like, you know, into like fancy shit. But like any book, like any investment in yourself, like it just pays off. Even if it's not immediate, it takes a while. Like Making my big bet around memes, I looked like a retard for 2 years and you even thought I was joking when I launched my software and everybody thought I was just ridiculous.

Now we're users. Yeah, exactly.

There's multiple Beehive users on there. And it's, I don't know, when you've got a vision and just betting on yourself with it, the willingness to stay through even when you look like an idiot, most people don't have the willingness to look like an idiot an idiot for long enough. Fortunately, like, I'm used to looking like an idiot and I embrace it. But like, most people don't have that. That's why like most fame people who go start a startup fail. That's why most like Ivy Leaguers, uh, who like, they're too scared because they're too scared of like the reputation risk. I thought about this earlier.

There's—

everybody here has at least a 7-figure business. There's not one Ivy Leaguer here. Every single person here is from a normal college and like I love that. I fucking love that. I'm very, very bearish on college. But like, when you don't have the fear and you're willing to look like an idiot, you will just do crazy shit. Like offering to engineer some shit for like $3,000 and like look like an idiot to most people probably. Your parents, I don't know if your parents like, my parents were very against me like quitting my job to go make memes and shit. Like, who cares?

You know? There's also something even like a through line with like the employee thing and like the early versus later stage of like, not like weird or controversial, but the more out there you are, the more you attract people that are more like you. So you said your 2 employees came to you.

Every single one. 7 employees, every single one has found me.

And it's like the trajectory that I have seen, and like, granted, we have some people who have joined recently who are incredibly like bought in, see the vision, but like early days, like we are the furthest thing from, we are very insecure, we are unstable, we have like less money, we're barely making money. And we're going up against like all these massive companies in the industry, like you would never bet on us. So the people who do come to us believe in the vision, they have the risk tolerance, and they like want to go to war and like really fight for what you're building. And then as the company matures, you get more people who are looking for like a 9-to-5, and it's, it's safe, there's good benefits, and like you start to optimize for different things. But like nailing your early core people is so important. It's kind of like what Dara says of like like, "Yo, you're gonna work, work." I expect our employees to work weekends. This is another founder here, not me, although a lot of our employees do work on weekends. And he's like, "Dude, that turns off 90% of people, and that's awesome. Those people, I don't even want them in this circle." 'Cause the world is big enough where you can repel 95% of people. You just need the 5% who are in line, see the vision, and want the upside that it takes. I've gone back and forth. I love the idea of a 4-day work week, for a lot of reasons, from retention, from lifestyle, from like trying to build healthier habits and also come to work for those 4 days more focused, more refreshed, and actually like ideally increase output. But the other way, like, I also love the 996 of like, hey, the market, the customers, everyone doesn't give a shit about your work-life balance. And like every employee at Beehive has equity and there's a path forward where I think this could be a $10-20 billion business. And their equity could be a new house, a new car, their college, their kids' college tuition.

And kids' college tuition.

And so like, I see that. I'm like, the only thing preventing us from where we are now and that is like us putting our heads down and like just building this thing and working. And if it means that, okay, maybe on a Sunday you're gonna have to give up a Sunday here and there, like, is that worth it? To me, obviously the answer is yes. I'd like to find more people who the answer is like, obviously yes. And if that's not everyone, I respect it. And so just I love that, dude.

100%. Repelling the wrong people. My content is very unhinged. It's very me. And people ask all the time, aren't you afraid of offending people? It's like, no, I want you to be offended. I want the wrong people to be offended because the right people just fucking love it. A lot of people respect me because I say the shit that other people are scared to or make the goofy memes or Even sex jokes, right? It's an arbitrage. Most people are afraid to make it, so I make them, right? And it's like, whatever you truly believe in, like, don't hide that. Double down on that shit. And that's how you'll find your tribe of people, right? That's how you'll find— for me, it was my memers. They all found me, right? And what I think as well is super cool is like, you know, 2 or 3 of my team members are overseas, right? You know, not native English speakers, but they understand memes better than 99% of SF NYC people better than anybody because the internet is all over. Two of your employees in India, who I've talked to, both of them are amazing, right?

Incredible. Like, I wouldn't even talk about remote work, but like, I think that outside of like the financial and logistical reasons of just hiring the best person for the job irrespective of where they live, there's so many benefits to like, we are better because we aren't 15 white guys in San Francisco building tech, right? Like, we are getting perspectives from so many different people in different companies and cultures and countries and like That makes us considerably better. So yes, it's amazing being in person. This retreat's awesome. When we do an annual offsite, I love getting together with the team and there's definitely unlocks there. I would go to bat and say that the benefits of a remote-first company far outweighs the benefits of— Oh, 100%, dude.

We are fully remote. For doing the show and in-person stuff, I do love those moments, but I'm naturally an introvert. I like to do that. But yeah, I do. My fucking employee in India, right? He is 23, 25-year-old meme lord, right? And totally gets memes. But from like day one, he's like, I see your vision. You're gonna be like Larry David of Silicon Valley. We're gonna like turn this into a show. We're gonna make— like, how do you know who Larry David is? Like, you're like a 23-year-old in India. Like, what the fuck?

That's amazing. Larry David is the GOAT.

I mean, he's the GOAT. But like, it's just crazy. Like, people, the amount of talent, like internet nativity and like content is everywhere. And so You could make friends with people all over. You could find employees who get it. Like I said, two of your employees in India just fucking get it. Great taste, great smart people.

I love Ben Thompson used to say the internet is so much bigger than anyone gives it credit for. Oh yeah. Which was his argument for saying that if you like X niche topic, there are tens if not hundreds of thousands of people that like that exact thing somewhere. That used to be part of my pitch for the seed deck. When we were raising money initially, everyone's like, dude, how many people are gonna write newsletters? And it was still in the early days where everyone just thought we were a Substack clone and they couldn't get over the fact that there's a few big newsletters, there's a few popular ones on Substack, how big could this get? And I think for whatever reason I defaulted to the internet's so much bigger than you give it credit for. They didn't give me money anyway. And that's not even the opportunity in what we're building. But yeah, it is very true.

There's a good line, this guy Henry Carlson, I think his name is. Where it's like a blog is a very comp— or a blog is the simplest way to find strange and interesting people and send them to your inbox. And it's crazy, like the amount of people— I wrote this article called Digital Apprenticeships, right? And that alone, one article has gotten me two employees because I just wrote about how I was apprenticed for Greg Eisenberg, who I was talking about earlier, and two guys who were in college hit me up, hey, I read this, I want to be your apprentice. Okay, hell yeah. Like, dude, you write about like just dope shit.

Writing on the internet has unlocked more doors for me than anything else. It's why we're here on this retreat. It's why I've connected to all these different founders. It's also been an unlock for the business. Like, I view Big Desk Energy as an extension of Beehive because it's a narrative that is now very commonly accepted, I'd say. But people resonate with people, not with brands. And so by sending all of your communications from the brand account and the brand emails versus like, we launched this feature, here's like a bit behind the scenes of like the shitstorm it took to even get this live, shows like the human element of what we're doing. It gets people, it personifies the business to, you see me in the business and you understand how I think, how I feel, what I prioritize, like what I value. So just adds like a narrative and I think you were talking about like we live to be amused, like people love stories. Like, that is the— all of human existence is the ability to tell stories. And to be able to add a story and a narrative to a company, I think, is extremely powerful. And furthermore, because I'm so transparent in real time, it's like startups are risky and hard, and like, it might not work out. And like, I take lots of like very controversial bets of like super in on remote culture, we're super transparent, we're making big bets in different areas. I'm like, I'm making these Bets in real time, you can read them and it's like a story that's unfolding in real time that you can follow along and maybe they work, maybe they don't. And it's like entertainment, story, tech, transparency. It's been awesome writing online.

100%, dude. Every startup is a media company. Every founder is an influencer and not just that, but like a storyteller. Dar downstairs earlier was talking about how all he does is tell stories and same here. People love that shit. When I wrote my post Founder Mode, when I quit my job during a company offsite and wrote literally a day-by-day play-by-play, that was the best thing I've ever written, I think. And I wrote it at 11:00 PM on a Saturday night in a hotel in Austin and just so much fun, so much energy. The amount of replies I got from that post alone, was just insane.

I'm looking forward to the day-by-day breakdown. Yes, because that was amazing. And then I think there was something else you did, whether it was Hereticon or something else, where like you documented like an hour-by-hour, and it was fucking awesome.

I love doing that. And because I write my newsletter every week, I thought about like, do I do this day by day every week?

It's like, I mean, like, not every week's that exciting.

Yeah, so some weeks are more exciting than others, so sometimes I can't do that, but like I love doing that. You give people a whole world into it. And I really just try to do that and be as open as possible, share the crazy stories. I remember during the founder mode post, I just half-assed, or not half-assed, I threw it in at the last second. I was like, told Alex Cohen I got chlamydia in college, blah, blah, blah. It's just dumb shit, just sharing the real thing. People appreciate it.

People want authenticity.

People want real, and if you're willing to do that, it pays off. Speaking of authenticity, we got the sun beating down and I'm sweating.

I know, so we might have to call that a pod.

Alright, this is dope.

Appreciate it.

Good shit, man. This was fun. Good shit, man.

Hopefully it saved.