Transcript
Startup Secrets in the Age of AI with Entrepreneur and Author Henrik Wederlin
From Tommy Mello · Episode page · Watch on YouTube
· 41 min · 8,537 words · 70 timestamped sections
This is the full, timestamped transcript of "Startup Secrets in the Age of AI with Entrepreneur and Author Henrik Wederlin", an episode of Tommy Mello published November 29, 2025 (41 min, about 8,537 words). It mentions 11 people, works and ideas, including Bark Air, BarkBox, Bark, Facebook, Me, My Customer, and AI.
What is discussed, and when
Notable quotes from "Startup Secrets in the Age of AI with Entrepreneur and Author Henrik Wederlin"
Entrepreneur, investor, author Henrik Worlin is the co-founder of Bark, the company behind Barkbox and Bark Air.
about Bark Air · atPlatform helping aspiring entrepreneurs build smarter, faster startups. This year, he published the book called Me, My Customer, and AI, Exploring Human First Entrepreneurship…
about Me, My Customer, and AI · atIn 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 his mentor said, You…
about Amazon · atWhat they could do in a year and they give up. There's a great book about this called 3 ft from Gold. And the best answer I could give to you is don't give up. Make a plan…
about 3 ft from Gold · at
Who and what is mentioned in this episode?
People
- Henrik Worlin — Person · 1 mention · first at
Entrepreneur, investor, author Henrik Worlin is the co-founder of Bark, the company behind Barkbox and Bark Air.
Books & papers
- Me, My Customer, and AI — Book · 2 mentions · first at
- 3 ft from Gold — Book · 1 mention · first at
Companies & orgs
- Bark — Company · 4 mentions
- Facebook — Company · 3 mentions · first at
Successful startups of the past decade with multiple exits to companies like Facebook, Dropbox, and Microsoft.
- MTV Networks — Company · 2 mentions · first at
Stuff. I thought I wanted to be a journalist and then I got a job at MTV networks and for those who don't know who that is that used to be a cool TV stations back in the days…
- Amazon — Company · 2 mentions · first at
- Dropbox — Company · 1 mention · first at
Successful startups of the past decade with multiple exits to companies like Facebook, Dropbox, and Microsoft.
- Fast Company — Company · 1 mention · first at
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. Your really key competitive advantages is to be able.
Products & tech
Full transcript with timestamps
I see AI as such a underlying foundational technology that the only way to use it as an iron man 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 how what makes humans tick.
Entrepreneur, investor, author Henrik Worlin is the co-founder of Bark, the company behind Barkbox and Bark Air. Building a startup today doesn't require hundreds of dollars, requires $20,000, $30,000 to build something pretty meaningful.
He's helped shape some of the most successful startups of the past decade with multiple exits to companies like Facebook, Dropbox, and Microsoft.
By forcing yourself to go out and sell pretty early, a few things happen. 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. Your really key competitive advantages is to be able to launch something very quickly and take decision very quickly.
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 Wordland with me. He's the co-founder of Bark, the company behind BarkBox and Bark Air. He's also the co-founder of Prehype and the founder of Autos, 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. Uh 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. I mean like I I started in entrepreneurship here back in Denmark u before I guess entrepreneurship was
really a thing because I'm an an old man by now but I've always been building stuff. Um, I thought I wanted to be a journalist and then I got um a job at um MTV networks and 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 it I took it upon myself to bring into the studio of MTV two 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've built a bunch of companies and some of them have been big and some of them didn't work out and here I am.
I love it. So tell me a little bit about I I want to hear first about the book me, my customer, and AI. 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 prehype. And over the last 10, 15 years, we then kind of been helping people figure 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 agents 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 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 it's about humans, problems, customers with AI as the co-pilot. Uh what was the hardest part about resisting the trend to just be straight pure AI and staying true to the humans first ethos? So the book is basically about two things. One is that we think that AI will dramatically um 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.
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.
I mean I our book we call it relationship capital we think it's it's one of the last moes 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 1015 years? what's a 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 believe belie believing that that those two things and the overlap is 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 in 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 coins. 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.
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 know, a 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. Um, the AI is going to handle it. I think if you partner with AI, get good at it, you could actually make yourself a hundred 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 5 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? 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. uh we can either kind of get all doom and gloom about all these changes that I think we'll face 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 in our community and I think you know obviously if you are entrepreneurial if you are resourceful if you are original odd. 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 JTBt your cla 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 that all these people that will be displaced and I think quite a few will they'll be able to find like a very meaningful work doing something uh on the top of an AI stack. I I've run this podcast called Beyond the Prom with a professor at Stanford and we interview people every other week about AI and 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 realize that for 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 it questions that are meaningful for us? And that means that we have to start to understand oursel much better. It's all about like all these things that Yeah. like taste and and decision making and gut feeling and all these different things like you know chachi have a tough time answering the question like uh you know uh 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 I I see AI as such a underlying foundational technology that the only way to use it as an Iron Man
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 how what makes humans tick. I
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 uh the old CEO of uh Google was on stage uh and he said listen SGI you know uh basically su super intelligence is smarter than every human being combined and it'll solve he says within three years the Silicon Valley San Francisco the the the large majority of these people believe that we're 3 years away from a breakthrough that'll change mankind forever. And at the rate in which we're moving, the 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 it's not going to taper off anytime soon."
I'm just curious your thoughts cuz you're much more wellversed. I mean, you obviously have a podcast about it. 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 thought 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 Jub 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 it will take for the algorithms to be you 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. Uh 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 AI to kind of get incorporated in all these different tools we 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 months 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 that's like 10 years ahead.
Like it's when chat dbt 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 be become but I do think that we can ask ourselves is how do I become better of using it and how do I become uh 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 I 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.
I just told my buddy last night I said I wish this would have come out 5 years from now. I said I 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 got to go back to the BBB and worry about these thumbtack and these crazy things that haven't mattered and now you got to worry Reddit and uh 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 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 yellowbook And this is when there was like eight al algorithms like Google was not the winner yet and it was interesting. Uh it was good for me cuz I was just starting out. But do you have any concerns? I mean like I took a little bit of time
off after we 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 [ __ ] this is exciting. So I think two thoughts I get worried about all the time. I'm like a worrier like a lot of other people like 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 this thing 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 dropping 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 I want to talk about the good things. I want to kind of like get excited about it.
Have you ever heard of a guy named Robert Shaini uh psychology? He wrote the book Influence. He's probably Oh, yeah. 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 education system." He just had so many great things to say, so optimistic and I really appreciated that.
I think it's tough not to get a little bit like, you know, also I think a lot of us we live 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. So I think you know like if you look at overall the next 1015 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 I just think you have to choose the first
one because the other thing is too depressing. I love it. You know, we've been learning so much. Whether that's claw, 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 the for the day before and populated it. And he used I think I think he 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, Tik Tok, 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.
And here's the crazy thing. It doesn't cost 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 and everything is fine. And then when I started Barkbox, you know, I had to figure out uh you know like how do you do recurling 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 do SEO on this stuff. But not anymore. And so I don't know, like I I think it's very easy to stare 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 disinish that. But I also think that if you think that it is awesome to serve somebody and if 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 to go out and do it.
I think you're spot on. I wanted to tell you that I love Bark Box. Me and my fiance have two dogs, Huckleberry and Finn. They're cava poos five and four the best dogs ever. I want to hear the uh the origin story behind bark. And what inspired you to to build it all around dogs?
I 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 uh if you were the cheapest, if you bought the cheapest ticket, you would just be randomly paired with somebody else and you would share a cabin. 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 hot 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 hot shaped bed on a cruise ship and I 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. as 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 um uh box with with treats and toys and so honestly the idea wasn't very grand. It was just like let's work together cuz we like each other. Let's make find some cool [ __ ] for dogs and then put in the
box and make people happy. and 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 got big on this idea that we wanted to build the Disney for dogs and so you know 15 years later we're flying airlines and you know have food and treats and toys and and everything so that's how it came about.
Yeah. Bark Air started in 2024 and it's like a uh concier service for dogs. Dog first travel service entirely built around the dog's comfort in the air and on the ground. One-way flights are around 6K per ticket. Uh what's the goal for Bark Air and what does it look like in 5 years? I mean like the 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 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 5 days or or I can't go. And so, what we wanted to solve was basically how do you bring your best friend, you know, on a on a trip and 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. So we've developed a champagne on chicken broth for them. We call their owners on the way to the airport to find out if the dogs want to have the windows open or closed on the way out there. We make a playlist for them, their spot treat.
Like you it's 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 and 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 bar 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 u lower and and our dream is to make it super affordable and a super great experience to travel around with your dog.
I love that. We [snorts] uh 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.
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. Um, I'm going to ask you a couple questions that I always ask on this. What's one piece of gamechanging advice you wish you knew in your early 20s?
You know what? I'll steal one from uh what's it called? Um Richard Branson who did Virgin. He goes asked, "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 h family happy. And so I think that's probably pretty important.
I agree. You you have five Ps. 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?
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 position of stuff like that or it's like you have a specific passion for something. And so I 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 uh should I start? I'll give you a good example. I uh 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 um 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 uh 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 five Ps 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 should 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 will be interesting for me? And the five Ps is basically a a little framework for try to help you do that.
Once you come up with an idea, are there any AI tools that you think are like the ultimate leverage? I mean like 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 gro chatbt 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 like we spent a lot of money making trademark analysis for all the dog toys we do So, a designer will come up with a toy.
He'll call it or she will call it uh like a you know like panel the cactus and then they will send it to the legal team. The legal team would kind of make a trade. I was like ah 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 sort of take 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 chatbt and then at the end I said, "Hey, please write this up as a full description of a concept and um directed to my design team and my head of AI."
And so as when I come home, there's just like a whole email ling 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 [ __ ] 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 uh 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? 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 sucked 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 auto.com, go to
Squarespace, go to Wix, whatever you kind of like tool, and you whip up a little landing page. And then I put 50 bucks of ad traffic against it. And then I see if anybody clicks and that I call a signal mining. And then if people clicked, 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 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 I just rinse and repeat and start and do it again.
Yeah. You know, Jeff Pesos, 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 AB test or at what point do you go, "Hey, race horses were blinders for a reason. take because now you're successful. You know, Henrik, you 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? Everybody always say that to me. So, yes, I I guess I 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 realize that. But I think ideas are kind of like annoying. What's is in interesting is when you can make them actionable. And I think an actionable 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 it's it's 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.
I agree. Listen, if if I think on my idea list, there's 287 things. And luckily now I have the resources to get a lot of them done.
On that list, 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?" Like what what do you think it is for you that makes you gravitate to something?
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. Uh I can't use a lot of my headsp space 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 a ADHD, but we're also likely, you know, we're hunters and and we we we're always thinking about stuff and it's not something you can 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 le 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?
I'm a pretty philosophical guy, so I'll give you like a pretty philosophical answer and 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's a 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 OpenMai, 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 like 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'll take you somewhere good. And I honestly believe a little bit like that. I've always like 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 [ __ ] 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, you like that was something as stupid as putting like two treats, two
toys in a chew in a brown box, you know, but like I mean then you IPO it and you know like 10 years later and every time I like oh you this will 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 [ __ ]
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 6040 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 and 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
I've tried had both, right? You know, at prehype, I did it by myself and I very much enjoyed that it was kind of my show and that I could just make the calls that I wanted all the time. Um, 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 partners, I always just found people I just really admire and enjoy hanging out with. I almost feel that it's the one like that I was the one who's like the you like the weak the weak link. Um 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 that has something they see they want to go for it. 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 grow up with.
How tough what was the experience of an IPO? I I hear good stories, but then you've got an earnout usually and there's a lot to it depending on how it's done. But what what was that like for you?
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 then 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 as a kind of like an 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. Uh 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.
A lot of highs and lows. 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 out like half a point, you're like, "What happened?" And obviously nothing happened, right? You know, it's just like whatever blur 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 for 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.
Yeah. Jeff Basos 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. I bought back bought back 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 uh 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 it it's crazy kind of seeing through their eyes on that.
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.
Well Henrik, I really appreciate you coming on and I appreciate you staying up. I learned a lot.
I appreciate it. 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. Do you know less than 5% of businesses ever cross $1 million in annual revenue, your chances are one in 20. And the reason why is most people underestimate what they can do in 5 years and overestimate what they could do in a year and they give up. There's a great book about this called 3 ft from Gold. 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.
Questions about this episode
What is discussed in "Startup Secrets in the Age of AI with Entrepreneur and Author Henrik Wederlin"?
In order: 0:00 Bark Air, BarkBox, Facebook, Me, My Customer, and AI; 15:00 BarkBox, Facebook; 20:00 Bark Air; 30:00 Amazon; 35:00 Amazon, BarkBox; 40:00 3 ft from Gold.
What is mentioned in this Tommy Mello episode?
11 people, works and ideas are mentioned, including Bark Air, BarkBox, Bark, Facebook, Me, My Customer, and AI, MTV Networks. Each one on this page links to its own page with every episode that mentions it.
How long is "Startup Secrets in the Age of AI with Entrepreneur and Author Henrik Wederlin"?
The episode runs 41 min; the transcript is about 8,537 words in 70 timestamped sections.
More from Tommy Mello
About this transcript: the episode's spoken words as captioned on YouTube, split into timestamped sections. Reclip.Me locates every person, work and idea in the text, keeps the time it is first named, and quotes the words around it verbatim. Last updated January 24, 2026.