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Henrik Werdelin
I see AI as such a underlying foundational technology that the only way to use it as an ironman suit is to become better of bench pressing yourself. And the only way that you can bench press better in entrepreneurship is to really understand what makes humans tick.
Tommy
Entrepreneur, investor author Henrik Werdelin is the co founder of Bark, the company behind Barkbox and Bark Air.
Henrik Werdelin
Building a startup today doesn't require hundreds of dollars, requires $20,000, $30,000 to build something pretty meaningful.
Tommy
He's helped shape some of the most successful startups of the past decade with multiple exits to companies like Facebook, Dropbox and Microsoft.
Henrik Werdelin
By forcing yourself to go out and sell pretty early, a few things happen.
Tommy
He's been recognized by Fast Company as one of the top 100 most creative people in business and by business insider, Silicon Valley 100.
Henrik Werdelin
Your really key competitive advantages is to be able to launch something very quickly and take quickly.
Tommy
Whether it's scaling companies, innovating in unexpected industries, or exploring the future of business, Henrik brings a perspective that is as strategic as it is inspiring. All right guys, welcome back to the Mellow Millionaire. Today I got Henrik Werderland with me. He's the co founder of Bark, the company behind Barkbox and Bark Air. He's also the co founder of Pre Hype and the founder of otos, an AI platform helping aspiring entrepreneurs build smarter, faster startups. This year he published the book called Me My Customer and AI Exploring Human First Entrepreneurship in the Age of AI, which I'm fascinated by. This has been like the conversation piece the last year. Henrik, it's a pleasure to have you on. So let's just start with your entrepreneurial journey, where you started, what you're excited about.
Henrik Werdelin
I mean like I, I started in entrepreneurship here back in Denmark before, I guess entrepreneurship was really a thing because I'm an old man by now, but I've always been building stuff. I thought I wanted to be a journalist and then I got a job at MTV Networks. Then for those who don't know who that is, that used to be a cool TV stations back in the days. And I had, I was asked if I could come up with a show about the Internet. And this is like late 90s. And I came up with this show, pitch it to my boss who thought it was kind of like a crazy idea, didn't like it much. And then I took it upon myself to break into the studio of MTV at 2 in the morning and make a live TV show. And back then you didn't get sued, you got like promoted. And so I I got into the whole entrepreneurship by basically running product development for MTV networks outside the US and then from that I built a bunch of companies and some of them have been big and some of them didn't work out. And here I am.
Tommy
I love it. So tell me a little bit about, I want to hear first about the book Meme My Customer and AI.
Henrik Werdelin
Well, the book is a bit of a passion project. You know, like I, I started in 2010, I, I was part of a company that sold to Facebook and I ended up not really knowing what I wanted to do. And so I ended up building kind of a halfway house for entrepreneurs that we called pre hype. And over the last 10, 15 years, we then kind of been helping people figuring out how to build companies. And we've been lucky enough with some of them. I got kind of obsessed about how do you take workflows and how do you atomize them and how do you create basically autonomous age that could do a lot of that work. And I thought for entrepreneurship there's a lot of shitty work you have to do. Maybe we can kind of offload that to some of these AI agents. And so I spent a lot of time figuring out what is entrepreneurship going to look like in the age of AI.
Tommy
You know, your book is, is often pitched as the AI book, but I know you made it clear that it's, it's not primarily about AI, it's about humans problems, customers. With AI as the co pilot. What was the hardest part about resisting the trend to just be straight, pure AI and staying true to the humans first ethos?
Henrik Werdelin
So the book is basically about two things. One is that we think that AI will dramatically kind of democratize who can build companies because you no longer really need like a computer science degree. And then following that, when everybody can build everything, what is really the thing that will be your moat? Like what is the thing that will make you stand out? And the thesis of the book is that your authenticity and your authority with a specific customer group is, is what's going to make it special.
Tommy
Yeah, I love that. I've been talking about building a brand. I was with Dan Martell recently in Canada and he said there's two things I'm investing my life into. AI, any AI backed company and personal brand.
Henrik Werdelin
I mean, our book, we call it Relationship Capital, we think it's, it's one of the last moats that's going to be back. And I think for me that's really the overlap of those two things. It's, you know, who, who do really, who do you care enough about to serve them for the next 10, 15 years? What's the meaningful problem that they have and why the hell should they want to buy it from you? Those are basically the three components that will matter. And then most other things you can basically build on the back of an AI stack. And so I'm very much in believing that, that those two things in the overlap is where entrepreneurship is going to head. And I guess a little bit my pitch is that I think we talk a lot about unicorns and building big companies, but the reality is that the US and most companies and countries in the world are built on the backbone of just very talented people who build small businesses. And what I hope we can do is not just build a bunch of one per person unicorns, but that we can build a bunch of what I think of as Donkey Kong. So one person companies that do a million turnover a year. And, and so I'm excited about not just that a lot of people can build big companies, but also that a lot of like everyday entrepreneurs can build something meaningful and, and, and serve somebody and make a good life for themselves.
Tommy
So this is a few selfish questions that aren't in my deck here, but where is the world going? I mean I'm thinking about anything that is repetitious, that I'm taking. One thing, putting a piece of data, whether that's payroll, hr, call center dispatch, you, lot of things that inventory there. There's so many things that I just feel like are kind of be going to be gone soon. The AI is going to handle it. I think if you partner with AI, get good at it, you could actually make yourself 100 times more efficient. There's still some things to keep an eye on, at least for the next few years. I mean it's a race right now. I think everything's going to get commoditized. Energy is going to become cheaper and cheaper. The AI will figure out energy issues very, you know, within the next five years. Right now that's a race for energy. But where does this go for the mankind and how does it all work out? Is it a government, government subsidized world?
Henrik Werdelin
I do think that what, you know, the best way to predict the future is to make it. And I think a lot of us now have a choice. We can either kind of get all doom and gloom about all these changes that I think we'll face or, or we could kind of say, hey, this is a new technology, probably at the level of like electricity. And then we can go out and say, how do we build something on top of that that makes something meaningful, that that is meaningful in our community. And I think, you know, obviously if you are entrepreneurial, if you are resourceful, if you are original thought, I think this is kind of a golden age because you now don't have to go and beg somebody else to do stuff for you. You can Basically turn to ChatGPT, your cloud or whatever is your foundational model of choice, and then you can actually make something. And so I hope that this will be kind of like a very inspiring time for all the people who says that they have this idea. They just don't really know how to get started. And if you look at the US and you survey people, that's 60% of the population, like everybody wants to do something. And specifically US is just like a country of entrepreneurship. And so I really hope that all these people that will be displaced, and I think quite a few will, they'll be able to find a very meaningful work doing something on the top of an AI stack. I've run this podcast called beyond the Prompt with a professor at Stanford, and we interview people every other week about AI and we've done it for a long time. And so I think a lot about AI. And here's the irony, the more I learn about AI, the more I realized that to really understand AI, you have to understand about humans. Because AI is really just a big generalized kind of like algorithm that gives you the average answer that a lot of people would answer. And so for us to get something useful out of it, we have to find out, like, how do we actually ask questions that are meaningful for us? And that means that we have to start to understand ourselves much better. It's all about like all these things that, yeah, like taste and decision making and gut feeling and all these different things. Like, you know, chatgpt have a tough kind of answering the question, like, you know, why is the party just getting started? Or the mood in the office is really weird, you know, like, that's like tougher to know. I see AI as such a underlying foundational technology that the only way to use it as an Ironman suit is to become better of bench pressing yourself. And the only way that you can bench press better in entrepreneurship is to really understand what makes humans tick.
Tommy
I got a deeper question because I was just at a Goldman Sachs event with people that I probably shouldn't have been invited there. I do garage doors and it was 75 founders and the old CEO of Google was on stage and he said, listen, SGI, you know, basically superintelligence is smarter than every human being combined and it'll solve, he says, within three years. The Silicon Valley, San Francisco, the, the large majority of these people believe that we're three years away from a breakthrough that'll change mankind forever. And at the rate in which we're moving, the Google CEO said we're still in the early, early infancy stages. A lot of people think these valuations are crazy, but they're just getting started. He's like, it's not gonna taper off anytime soon. I'm just curious your thoughts cuz you're much more well versed. I mean you obviously have a podcast about it.
Henrik Werdelin
I don't know how long it will take, but I am also pretty convinced that we'll get to something in the foreseeable future that is very, very capable. But I think also like what we have, like if we just start with what. I think if we stopped developing AI today, we as entrepreneurs would have like 10 years where we could just build on what we have today. I mean like what we have in ChatGPT is freaking insane. I mean like, and most people don't know how to use it. And so I think there's two questions, that is how long will it take for the algorithms to be, you know, get to a artificial general intelligence AGI as they kind of think. I don't even think people really know what that means. And so we'll have to kind of like spend some time debating that. But let's say that it'll just be much smarter than it is now. I think that will happen. I think that we will all have to figure out how we implement it and it'll take some time for our AI to kind of get incorporated in all these different tools we use. And I guess I go a little bit back to like I don't think anybody really knows, you know, I think the people that know the most, they probably know three month more than the others. But like, and all the models, when they become available, they become available to everybody. Like it's not that there's like a huge secret lab with a AI, there's like 10 years ahead. Like it's when ChatGPT kind of comes up with something, they put it on the Internet, right? And so I don't think that we can use the thinking much in what it might become, but I do think that we can ask ourselves is how do I become better of using it? And how do I become good at understanding how I can take this tool and turn it into something either I can make money on or that could serve my community. And that is kind of like the only real thing I spending time on, because I don't have the answer to. Like, your bigger question is, like, how long it's going to take and how crazy it's going to be.
Tommy
I just told my buddy last night, I said, I wish this would have come out five years from now. I said, I. I've been. I've been working at this business for 20 years, man, we're. We're in such a solid spot. And now it's like, now I gotta go back to the BBB and worry about these thumbtack and these crazy things that haven't mattered. And now you gotta work Reddit and, you know, there's like. And then it changes every day. And I know I'm in the same spot as everybody. At least I'm reading about it, I'm doing podcasts about it. But it's making business. It's like, when I was. I was in the first year of. When the yellow book went out of business, I was my first year in business. I was a yellow book ad. And this is when there was like, eight algorithms. Like, Google was not the winner yet. And it was interesting. It was good for me because I was just starting out. But do you have any concerns?
Henrik Werdelin
I mean, like, I took a little bit of time off after went public, and I thought I would just be really good at gardening and stuff like that. And then I got insanely bored, and then I got really deep on AI and I was like, holy shit, this is exciting. So I think two thoughts I get worried about all the time. I am like, a worry like a lot of other people. I catastrophize, like, you know, like, all day long. So, yes, I get worried a lot. I think there's two thoughts, though. One is, I think it's a choice. I think you can either just get super worried and you can tell everybody else that you're super worried, but there's also a version where things can go well. There's also a version where it doesn't have to suck. My daddy's 86, and I talked to him about it the other day and talk about how miserable it was, the whole thing, and how all these things could go wrong. He goes like, dude, like, when I had to buy sugar, I had to kind of give them a coupon because it was during the Second World War. Like, they were literally drumping bombs on my house. Like, yes, I understand how things are a little Bit kind of naughty right now, but like, dude, like, hold my beer, right? And so I do think that we just have to decide, like, do we want to see all the bad things that can happen or do we want to try to like, figure out what is the good things that we can do and then just spend a lot of time talking about that. And I know it's a little bit naive, but, like, I'm deciding to do the latter. I want to talk about the good things. I want to kind of, like get excited about it.
Tommy
Have you ever heard of a guy named Robert Ciardini? Psychology. He wrote the book Influence. He's probably the world's expert on influence. And I was. He was in here with me. He's in his 80s now, and he came over for dinner, we drank some wine and he's like, I am so excited. He's like, this world, he's like, it's just the most exciting thing in the world. He's like, things are going to become more affordable and people are going to be able to live better and the third world countries won't be third world. And the edgy education system. He just had so many great things to say, so optimistic. And I really appreciated that.
Henrik Werdelin
I think it's tough not to get a little bit like, you know, also I think a lot of us, we lived through like a generation where things were pretty awesome. Like, you know, things were kind of like in general getting better across the world, you know, like, obviously a lot of people specifically in the US have also lived through like a period of time where things just kind of stayed a little bit like, flat and was miserable about that. And so I think, you know, like, if you look at oval the next 10, 15 years, I think it's going to be wild. And I think it's a lot of things going to change. And I think you can basically strap in, enjoy, enjoy the show, and have a good time while you see where that takes us. Or you could be super miserable and try to hide all your money under your blanket and then kind of like go to bed and wake up and hope the whole thing goes away. And. And I just think you have to choose the first one because the other thing is too depressing.
Tommy
I love it. You know, we've been learning so much. Whether that's Claude gbt, there's just so much to learn. But you look at these workflows now. I watched a guy make something in minutes. It scraped the Internet for the top technology and it went through Huffington Post and all the major articles. Wall Street Journal found the top one with the most reviews for the day before it populated it. And he used, I think, I think it was using Claude and then a few other tools. And then it literally transcribed it, rewrote it, built the top thumbnail and then it posted the top one for LinkedIn X, Facebook, TikTok, Instagram and YouTube. And his hey Jen, which he created. Just him talking about it, talking ahead. And it's really, really good. And it's like a shadow account.
Henrik Werdelin
And here's the crazy thing, it doesn't cost you really anything to do. And you can learn those things just by watching a few YouTube links. Like, it is just incredible. You know, when I like, as mentioned, I was old, right? Like, the first thing I had to do when I do had to make my first startup. This is like late 90s, I had to find somebody to give me $5,000 for a Windows NT server. Then I had to find somebody who would understand how to connect it to the freaking Internet. Like now, of course, you just like swipe your credit card and you're on the cloud, everything is fine. And then when I started Barkbox, you know, I had to figure out, you know, like, how do you do recurring, recurring billing software? And now again, you swipe your credit card and there's something called recurly and they'll just kind of do it for you. But I still had to figure out like a designer, a developer and somebody who can understand how to SEO on this stuff, but not anymore. And so I don't know, like, I think it's very easy to steer yourself blind on how difficult it's going to be for a lot of people. And I do think it's going to be difficult for a lot of people. So I don't want to diminish that. But I also think that if you think that it is awesome to serve somebody and you think it's very interesting to really dig down to what is a meaningful meaty problem and you have like the originality to come up with a solution for it, you really don't have any excuse anymore than to go out and do it.
Tommy
I think you're spot on. I wanted to tell you that I love Barkbox. Me and My fiance have two dogs, Huckleberry and Finn. They're Kava Poos 5 and 4. The best dogs ever. I want to hear the the origin story behind Bark and what inspired you to. To build it all around dogs.
Henrik Werdelin
I wish it wasn't kind of like as goofy a story. So I was just trying to figure out what I wanted to do next. And I had booked a ticket for a conference that happened to be on a cruise ship. And if you were the cheapest, if you bought the cheapest ticket, you would just be randomly paired with somebody else and you would share cabins. And of course they've taken the bed and they pushed it apart into two different beds because you didn't know who it was. Now I checked in first and thought it would be hilarious to redo the bed as one and like a heart shaped bed in a cruise ship. And I went out for a drink and then came back a little bit late to the cabin, at which point my now co founder Matt had already checked in. And so the first time I ever meet this dude, we're lying in a heart shaped bed on a cruise ship and I'm kind of awkwardly have to put my hand over the duvet and kind of shake his hand. So that's how we met each other. And then we were talking about the companies we built. He had just built something called meetup.com and I built like this business that we had exited pretty fast. We got to talk about dogs and Matt had this great Dane called Hugo that lived in New York City with him and he couldn't find cool stuff for it. And we were like, why don't we just make like a really cool discovery box with, with treats and toys. And so honestly, the idea wasn't very grand. It was just like, let's work together because we like each other. Let's find some cool shit for dogs and then put in the box and make people happy. And luckily it kind of took over really fast. And then we kind of like started to think, hey, what could this become? And we've gotten big on this idea that we wanted to build the Disney for dogs. And so 15 years later we are flying airlines and have food and treats and toys and, and everything. So that's how it came about.
Tommy
Yeah. Bark air started in 2024 and it's like a concierge service for dogs. Dog first travel service entirely built around the dog's comfort in the air and on the ground. Oneway flights are around 6k per ticket. What's the goal for Bark Air and what does it look like in five years?
Henrik Werdelin
I mean like the, the real story is that if you have a big dog and you want to fly across country or let alone you want to bring it on vacation to Europe, like you're pretty, you know, stuck, right, you know, and you don't want to put it down in the, in the cargo hold. And I think, you know, I have a, you know, a slightly older Labrador and I mean I'm not putting her in, in a box and putting in cargo. So for example, when we want to go to Europe, like I just, I can either sail her on the Queen Mary II for like five days or I can't go. And so what we wanted to solve was basically how do you bring your best friend on a trip? And that didn't work. Now like when Uber started, they started with Uber black because. Or Tesla started with kind of like a sports car, right. Because it was expensive to kind of solve this. And so we've started in the very high end where we fly dogs first class. We fly them in, you know, private jets. We've developed a champagne on chicken broth for them. We call their owners on the way to the airport to find out the dogs want to have the windows open or closed on the way out there. We make a playlist for them. Their spot treats. Like it is crazy. But the dogs and their owners like freaking love it. Right? The dream is to make it affordable for everyone. So if you want to go back for Thanksgiving and you live in New York, you have to go to Chicago. You don't have to drive for like eight hours or whatever it takes. Then you can jump on a bark airplane and then you can be back. So we have slowly started to be able to fly bigger and bigger planes, which means that we can put the ticket lower and, and our dream is to make it super affordable and a super great experience to travel around with your dog.
Tommy
I love that we, we're fortunate enough to take the dogs quite a bit to Idaho. It's a two and a half hour private flight, so it's. But I know what you mean. Not being able to bring the dogs is a huge dilemma. I mean when you, they're your family, I mean they're like for me, I don't have kids yet.
Henrik Werdelin
I mean like and I think, I mean if you, if you go on YouTube and you check out Bark Air, you'll have like a giggle. It's like the best videos of dogs having a great time. And there's also one of my co founder, Matt, which I put in a crate and got him to fly from Miami to New York just to kind of show how miserable experience it is.
Tommy
I'm going to ask you a couple questions that I always ask on this. What's one piece of game changing advice you wish you knew in your early 20s?
Henrik Werdelin
You know what I'll Steal one from, what's it called, Richard Branson, who did Virgin. He goes, ask, if you had only one advice to an entrepreneur, what would it be? And he answered, go to the gym. And I can see you're somebody who take care of yourself. I mean, like, I, I'm in my late 40s, and I didn't really start to go to the gym until I was in my, like, late 30s. And, you know, it's tough starting that day. So I will say, I mean, like, it sounds such a cliche, but, like, take care of yourself. If your hardware or your software breaks down, then you're not going to make any money, you're not going to make your family happy. And so I think that's probably pretty important.
Tommy
I agree. You, you have five P's. You talk about powers, passions, possessions, positions and potentials as a way of helping someone find inspiration as an entrepreneur. Can you talk a little bit about each of those?
Henrik Werdelin
Yeah, I mean, like, I think in general, a lot of people say they'd like to start something. A lot of people just don't know where to start. And so I think a lot of people then start by thinking, oh, is there a new technology I can work on? Or what is a business model? And I think a lot of time what you really need to find is something that gives you energy. And the five Ps are basically ways to try to ask yourself the question of, do I have something already in my world that I can just tap into? And that could be that you are a position of being a dad, or you're in a position of being a teacher, or you're in a position or stuff like that, or it's like you have a specific passion for something. And so I think a lot of people, when they talk about entrepreneurship, they think about what is the thing they can start and then they forget to ask the question, should I start? I'll give you a good example. I. We have this thing called Autos. It's on autos.com, you can go in. It'll help you come up with an idea to help you build a business. And so our hope is to help a million people over the next 10 years build a business. And we had a journalist from the Economist, and I walked him whole thing through, and he built a business that was really about. I hope I'm not saying anything I'm not supposed to say, but his business idea was like helping people who have aging parents about how to kind of deal with all that. And we built the first version of the business and we throw some ads at it and had, like, not super traction, but it also, like, had a little bit of sizzle, right? And as he was doing, he realized, hey, I don't really feel very comfortable being this business. Like, this is not the business that I'd like to start. Like, somebody should probably start this business, but not me. So the 5PS is really trying to give people a little bit of an assistant of trying to figure out not what business they can start, but what business they should start. And also maybe try to ask a little bit of the question of, like, what's the type of venture that I'm into? Some people should go and raise venture, but some people should just bootstrap it sometimes. Some people should be a solo entrepreneur. Some people should make a little mom and pop store. Somebody should make an agency. You know, like, there's like a thousand different flavors of entrepreneurship. But the question that a lot of people don't ask themselves is, what is it that I would like to do? Basically, where do I have something that make me unique to do it? And then what is the type of business that'll be interesting for me? And the 5PS is basically a little framework for trying to help you do that.
Tommy
Once you come up with an idea, are there any AI tools that you think are, like, the ultimate leverage?
Henrik Werdelin
I mean, the first thing people should do, if they haven't already, which is like the most basic, is just install one of the models on their phone, right? Like, do grok chatgpt Perplexity. And then they should just start by getting into the practice of babbling into the phone. Like, most people have some inklings all the time, and it just stays in their brain. I'll give you one from like I did the other day. I was walking with the dog, and then I was like, we spent a lot of money making trademark analysis for all the dog toys we do. So that signer will come up with a toy. He'll call it, or she'll call it like a, you know, like Prunelle the cactus. And then they'll send it to the legal team. The legal team would kind of make a trade. I was like, oh, maybe I can just make a little agent that could have that where they could just say the name that they want. It could go out and search it. It can then come with a recommendation back, maybe even like, with different name if the first one's kind of like solar tick right now. That took me, what, 30 seconds to explain to you. Instead of that just being like, A random thought in my brain, I babbled it into ChatGPT and then at the end of it said, hey, please write this up as a full description of a concept and direct it to my design team and my head of AI. And so as when I come home, there's just like a whole email link in there. I copy paste it, I send it to two people and hey presto, like a little bit like three days later, somebody comes back, say, oh, we use it and we're now saving shit ton of time on that. And so to start with it is get stuff out of the brain and get it on to something that is actionable. And I think it's such a superpower and nobody's doing it. So the way that I think about coming up with business ideas is I try to look for problems, right? So I have like the people who listen to can't see it, but you can see my notepad here. It says it sucks. That and it sucks. That is basically my, my key statement for expressing something that I think is pretty annoying. It's not just a little irritating, it's like stuff that has to suck, right? Like, and so it sucks. If you can say it sucks, that then you pretty much have a business idea on the back of that. Because if you can come up with a solution to that problem, then somebody's probably going to pay you for it. So I run around and I basically try to find it sucks that statements. And then I try to figure out who it is that it sucks for. And then I try to come up with something that can do relatively easy, like a solution. I call it an easy start. A easy start with a big finish. What is something that I think I could come up with a solution for like over the weekend even? I just do it manually myself. But if I sold it for a lot of people, it could be a pretty big business. And then I create a landing page, go on autos.com, go to Squarespace, go into Wix, whatever you kind of a tool and you whip up a little landing page. And then I put 50 bucks of A.D. traffic against it. And then I see if anybody clicks and that I call it signal mining. And then if people click, I call them and say, hey, you clicked on my thing. You know, why did you do that? What do you think? You know, how much would you pay for it? And then I basically use that a little bit of like stone carving. I see that's kind of like an inkling an idea. And then by all this new information, I kind of like just carve away. And then sometimes I'm lucky that I see something, I go like, oh, this could actually become something. Sometimes I don't. And it just rinse and repeat and start and do it again.
Tommy
You know, Jeff Bezos, he said a long time ago in an interview, he said in 30 minutes, he said he hired a bunch of consultants that ended up working for Amazon. In 30 minutes, Jeff could whiteboard more ideas for Amazon. And. And his mentor said, you could bankrupt Amazon in 10 minutes. He goes, your ideas, you have so many ideas. And he goes, so you've got to learn to control and prioritize the ideas when the team's ready, because you can't give them 80 things at once. Now, with AI, that changes the game quite a bit. But do you just think kind of starting a bunch of different things and just testing with 50 bucks, a few hundred bucks, whatever, seeing what catches on, Is that like just a good way to a B test or. At what point do you go, hey, racehorses wear blinders for a reason? Take. Because now you're successful, you know, Henrik, you've got the money and the resources to have an AI team and to have these things and be able to test things quite a bit. But when you're starting out, you know, do you think that. That all these ideas sometimes could you lose focus?
Henrik Werdelin
Everybody always say that to me. So yes, I guess. I mean, like, I think that is what a lot of people offer the advice. I am promiscuous when it comes to ideas. I love, like something new and it's completely my Achilles heel. I realized that. But I think ideas are kind of like annoying. What's is interesting is when you can make them actionable. And I think an actionable bolt idea is actually quite valuable. I think the world probably needs more people who think of something new. I need to make a few different things at the same time. And then I look for signal that what I'm doing is not dumb. And I don't know if I don't have the intellect or I don't have the discipline. I don't know which one that is until I put it out in the world. And so sometimes it's just about telling you the idea and then just see your reaction. And if you get excited about it, I get a little bit more excited about it and then I do a little bit more. And like, so like this. So I think about it like making snowmen. Like, you need to make the snow first snowball. And that's a little bit complicated, right? Because like, the snow is kind of, like, tough to get together. The second that you have something that's pretty compact and you put it down, you get to roll it two or three times. It becomes much easier because now you have the solid form. Now it's just about rolling it. You've been smart, you walked uphill, so now you just have to roll it downhill. I think it's okay to make a few snowballs first and then just see which one is the easiest to kind of, like, get turning a little bit.
Tommy
I agree. Listen, if. If I think on my ideal list, there's 287 things, and luckily now I have the resources to get a lot of them done on that list.
Henrik Werdelin
Like, when you have, like, something like, there's always one thing that kind of, like, is the one when people ask, like, oh, what is the thing you're thinking on? What. What do you think it is for you that makes you gravitate to something?
Tommy
Well, what's interesting is I'm involved with a lot of things. This is my core business. I'm a CEO of this business. But I've got big teams in the family office that, you know, we've got 25 developers just working on one product. I was just on a podcast earlier with another guy that I've. I'm involved with another product. I can't use a lot of my headspace because I do have obligations to the thousand people that work here, and they've each got three people depending on them. And the weird thing about guys like you and I are most people don't understand. They think there's something wrong with us. They think, like, they think, you know, we're more likely to be adhd, but we're also likely, you know, we're hunters, and we're always thinking about stuff, and it's not something you could just turn off. What I don't like people saying is you should always have a side hustle, because I find that measuring, like, you know, how many side hustles do you want? Because you never built anything to begin with. You don't have any savings account. You know, you're not spending a lot of time with family yet. Like, let's make up your core. Let's get some. Some money saved. Let's. Let's be good at a couple of things first. But, you know, it's hard to take away the entrepreneurial spirit. If you had to start over with 10 million only and your network, it sounds like you're super entrepreneurial. But where exactly what would you do with it? What would be the. The way you'd spend the money?
Henrik Werdelin
I'm a pretty philosophical guy, so I'll give you, like, a pretty philosophical answer, and then we can make it a little bit more concrete for people. I read this book recently. It's called why Greatness can't be Planned. It's by Kenneth Stanley. He was a professor in Miami doing AI. He made an algorithm, sold it to Uber, became head of AI for Uber, then went to OpenAI. Now he's doing something else. He wrote this book that basically say all great ideas were never really planned. It wasn't about just visualizing them working. What you have to do is to pursue with great intensity what he calls interestingness. And if you just pursue what you find to be deeply interesting, and you do it with a lot of passion, then that will create the stepping stones. And it might not take you where you thought it would take you, but it will take you somewhere good. And I honestly believe a little bit like that. I've always made the joke that every time I try to chase making money, I always end up with pretty mercenary people. And every time I try to build cool shit with people I really like, I always end up kind of, like, doing something good. And so I think I would go back to basically the first principle that I think have kind of, like, gotten me the things that I enjoy the most, and that is find somebody who I really admire and aspire to hang out with, and then find something that I just want to think about all the time and then just work on that. And for me, like, that was something as stupid as putting, like, two treats, two toys, and a chew in a brown box, you know, But I mean, like, then you IPO it and, you know, like 10 years later. And every time I like, oh, yeah, this would be a big business, and I can just do that and flip and all that stuff like, which I think some people have success with. I always end up kind of being miserable. So I would. I would just follow cool people and do cool shit.
Tommy
You think? What is your take on partnerships? Because most people. I talk to a lot of entrepreneurs. I know a lot of people, and it feels like almost sometimes like a marriage, like, you want to meet 50, 50. Most people 60, 40. But money changes people, man. I hate to say that, but certain people like to work more. Some people like a little bit more freedom into travel, and there becomes animosity. But what is your take on partnerships versus just being the sole decision maker? It sounds like you've had a good experience Overall.
Henrik Werdelin
I've tried both. Right. You know, at Pre Hype, I did it by myself and I very much enjoyed that was kind of my show and that I could just make the calls that I wanted all the time. I find the journey just to be so long and you know, like with Matt and Carly at Barkbox and Nicholas at Autos and with my different business partner, I've always just found people I just really admire than I enjoy hanging out with. I almost feel that it's the one like, that I was the one who was like the, you know, like the week, the weak link. So I've had a lot of, I have a lot of happiness with it, but I definitely sympathize with people who just want to kind of like, you know, have, have the killer instinct. They have something they see they want to go for. They don't want to be slowed down by anybody. You know, I think that works too. I think it's a little bit of the personality you, you grew up with.
Tommy
How tough. What was the experience of an ipo? I, I hear good stories, but then you've got an earn out usually and there's a lot to it, depending on how it's done. But what, what was that like for you?
Henrik Werdelin
I will say that I have sold companies and made some money on it and I was very grateful for that. There was nothing as an entrepreneur, I think as impactful for me as ringing that freaking bell. Like standing there and touching the bell and hearing go ding, ding, ding, ding, ding, ding, ding is like winning the Oscars or the Nobel Prize for entrepreneurship, right? Like it's just. And then when the, when the stock goes down afterwards, you're obviously super bummed about it, but nobody can kind of take that moment away. I didn't think it would be a big deal. I always just thought it as a kind of like, and kind of like investment event. But I have to say, just standing there, it did transform me quite a bit. If somebody came and asked me for an advice. Would you sell the business and. Or would you go public? I would like most times say go sell the business. But I do think for some people like my co founders and I who aspire to build like a business that's going to be around forever, then you really only have the option of going public. And then you just have to take the pain and misery that goes with being a public company.
Tommy
A lot of highs and lows.
Henrik Werdelin
A lot of highs and lows. And I think, you know, what you don't think of as a, a private company, you know, here you obviously sit and look at that freaking stock ticker, like, every second. And then, like, when it goes up, like, half a point, you're like, what happened? And obviously nothing happened. Right? You know, it's just like whatever blurb there was in the market that day. So it becomes this kind of constant, kind of like, I don't know, like, evaluation of what you do when reality is that there's all these technical reasons why it goes up and down and stuff like that, and you really just have to, like, not look at it and then keep your. Your head down and just build a robust good business.
Tommy
Yeah. Jeff Bezos was asked about when Amazon was struggling in the stock. He goes, I didn't care. He goes, big deal. He goes, it was a cheap pickup by Botbat's Botback stock, but I had a vision of where the company was going to go. And we knew we were profitable. We knew we had stuff getting released, but. But I could see being entrepreneur. I have some buddies that just went public with a massive company and they're like, man, we've hit all of our numbers. We've excelled every quarterly expectation, and a stupid article will come out, it'll affect the stock dramatically, and it's.
Henrik Werdelin
It, It.
Tommy
It's crazy. Kind of seeing through their eyes on that.
Henrik Werdelin
Yeah, I mean, like, that's not ideal. I mean, like, you pay, you pay, you play at the. At the. At the big roller kind of like table. Then sometimes you get hit in the nose a little bit and, you know, you just have to kind of like, get ready and play another round.
Tommy
Well, Henrik, I really appreciate you coming on and I appreciate you staying up. I learned a lot.
Henrik Werdelin
I appreciate it.
Tommy
Thanks so much for listening to this episode, like always. We're going to close it out with the Tommy Truth, which is a little slice of wisdom from me to you that can help guide you in whatever you're striving towards right now. You know, less than 5% of businesses ever cross $1 million in annual revenue. Your chances are 1 in 20. And the reason why is most people underestimate what they could do in five years and overestimate what they could do in a year, and they give up. There's a great book about this called Three Feet from Goal. And the best answer I could give to you is, don't give up. Make a plan, reverse engineer it, and stay the course. Go for the long term. Start to learn how to build teams and not be so reliant on yourself. Businesses that track key performance indicators grow 60% faster than those that don't. When you know the score, it's a lot easier to win the game. And that's it, guys. We'll talk to you next week.
In this lively episode, billionaire entrepreneur Tommy Mello sits down with Henrik Werdelin—serial founder, author, and co-founder of Bark (the company behind Barkbox and Bark Air)—to discuss what it really means to be an entrepreneur in the era of Artificial Intelligence. They explore how AI is changing the game for startups, why human-centric problem-solving is the ultimate advantage, and Henrik’s personal path from MTV to building beloved brands for dogs. This conversation is full of actionable tips, candid wisdom, and optimism for anyone building or scaling a business today.
On AI’s Role:
“The only way to use it as an Ironman suit is to become better at bench pressing yourself. And the only way that you can bench press better in entrepreneurship is to really understand what makes humans tick.” – Henrik Werdelin ([00:00], [09:36])
On the Future for Entrepreneurs:
“What I hope we can do is not just build a bunch of one person unicorns, but that we can build a bunch of...Donkey Kong[s]: one person companies that do a million turnover a year.” – Henrik Werdelin ([05:15])
On Optimism vs. Worry:
“You can either just get super worried...or figure out what is the good things that we can do and then just spend a lot of time talking about that. And I know it's a little bit naive, but, like, I'm deciding to do the latter.”
– Henrik Werdelin ([13:47])
Barkbox Startup Story:
“The first time I ever meet this dude, we're lying in a heart shaped bed on a cruise ship and I'm kind of awkwardly have to put my hand over the duvet and kind of shake his hand. So that's how we met each other.”
– Henrik Werdelin ([18:57])
Execution with AI:
“Get stuff out of the brain and get it onto something that is actionable. And I think it's such a superpower and nobody's doing it.”
– Henrik Werdelin ([26:45])
IPO Reflection:
“Standing there and touching the bell and hearing go ding, ding, ding...is like winning the Oscars or the Nobel Prize for entrepreneurship, right?”
– Henrik Werdelin ([37:42])
If you’re building in today’s AI-powered world, the playbook is wide open and the tools are at your fingertips. What matters most: a deep understanding of real human problems, the authenticity of your connection to your customers, the creativity to launch and test ideas, and the courage to stay positive (and healthy!) in a rapidly changing world. Barkbox’s heart-shaped-bed origin, AI prototyping tips, and the honest reflections on entrepreneurship—from “bench pressing yourself” to ringing the IPO bell—make this a must-listen for builders looking for wisdom and inspiration.
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