I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson

You don't want to walk into the gym on day one and try and deadlift £300. So when someone comes to me and they're a first time entrepreneur and they say I'm going to make the next great AI company, I think that is the equivalent.

I feel like you've actually started and run more companies than maybe anyone else in the world. What is your best advice for coming up with a great startup idea?

Charlie Munger, Warren Buffett's longtime business partner, has this amazing quote is where the fish are. The biggest mistakes I've made have been going into business models where other people have repeatedly failed and thinking I can do this better.

It's so funny to watch you on Twitter. Clearly you've become AI obsessed.

It's like having the world's most reliable employee who costs $200 a month and works 24 7. So many knowledge work jobs are going to change massively. I think the fundamental question is do all jobs just become a single prompt.

Today my guest is Andrew Wilkinson. Andrew is the co founder and CEO of Tiny, a holding company that's often called the Berkshire Hathaway of the Internet. They own over 40 businesses ranging from Dribble to E Commerce to the Aeropress Coffee Maker and they focus on buying profitable businesses from founders and holding them for the long term. Andrew and his co founder bootstrapped the business from zero to hundreds of millions of dollars in value and Andrew personally was worth over $1 billion. At one point in our wide ranging conversation we cover a bunch of strategies for coming up with a good business idea, what common business ideas you should avoid his experience automating much of his work and life using AI and what that means for employment in the near future. Also what he's learned about happiness and money and how they are not directly related and also how getting diagnosed with ADHD and then taking SSRIs was the thing that most impacted his happiness in life. This is both a powerful and also a very tactically useful conversation and I'm really excited for you to hear it. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. Also, if you become an annual subscriber of my newsletter, you get a year free of a bunch of amazing products including Bolt Linear Superhuman Notion, Perplexity Granola and more. Check it out at lenny'snewsletter.com and click bundle. With that I bring you Andrew Wilkinson. This episode is brought to you by Sauce. The way teams turn feedback into product impact is stuck in the past. Vague reports, static taxonomies, unactionable insights that don't move business metrics. The result? Churn lost deals, Missed growth. Sauce is the AI product copilot that helps CPOs and product teams uncover business impact and act faster. It listens to your sales calls, support tickets, churn reasons, and loss deals, surfacing the biggest product issues and opportunities in real time. It then routes them to the right teams to turn signals into PRDs, prototypes, and even code that drives revenue retention and adoption. That's why whatnot, Linktree, Incidentio, and Zip use sauce. One enterprise uncovered a product gap that unlocked $16 million ARR. Another caught a spiking issue and prevented millions in Churn. You can too at Sauce app Lenny Sauce built for AI product teams don't get left behind this episode is brought to you by Interpret. Interpret is a customer intelligence platform used by leading CXN product orgs like Canva, Notion, Perplexity, Strava, Hinge, and Linear to leverage the voice of the customer and build best in class products. Interpret unifies all customer conversations in real time, from gong recordings to Zendesk tickets to Twitter threads and makes it available for your team for analysis and for action. What makes Interpret unique is its ability to build and update a customer specific knowledge graph that provides the most granular and accurate categorization of all customer feedback and connects that customer feedback to critical metrics like revenue and csat. If modernizing your voice of customer program to a generational Upgrade is a 2025 priority, like customer centric industry leaders like Canva no Notion, perplexity and linear reach out to the team@ interpret.com Lenny that's E N T E R P R E-T.com Lenny Andrew, thank you so much for being here. Welcome to the podcast.

Oh thanks man. Great to be here.

I've been wanting to chat with you for so long. There's so much that I want to talk about and I want to start with a topic that I know that you think a lot about and that's also in the minds of a lot of people, which is coming up with a great startup idea and this is something that a lot of people are thinking about right now because AI makes it so easy to actually build your idea into something real and I feel like this is something you spend a lot of time thinking about. I feel like you've actually started and run more companies than, I don't know, maybe anyone else in the world. I feel like you're in the top hundred top ten. Something like That. I don't know, does that feel right?

I've definitely had a lot of experiences, and I've probably started or been involved with 75 different projects or businesses where I've been a primary contributor. And I wouldn't say that's anything to brag about, because I've been an inch deep in a mile wide. So that's been, in a lot of ways, kind of my Achilles heel is I get too excited about ideas and I start too many businesses. But as a result, I've seen almost every business model under the sun.

Amazing. Okay. So, yeah, I think the benefit is for us is we get to learn from your experience. So let me just ask you this question. What is your best advice for coming up with a great startup idea?

Ultimately, the best thing is something you're going to be interested in. But I think a mistake a lot of people make is they choose something that everything is everybody is interested in. So, for example, they say, I don't know anyone that has had the thought, man, I would love to start, like, a really cool restaurant or I want to have a cool cafe or something. And in reality, what they think about is how cool would it be to come up with an amazing logo or, you know, all the fun stuff, design the logo, the menu and stuff. But in reality, operating those businesses is miserable. And it's also a very hard business because every morning millions of people wake up and they go, I should start a cafe. But on the flip side, almost nobody wakes up every morning and says, you know what? I'd love to start a funeral home, or I would like to start a pest control business, or I should start software that helps people fill out forms for the government. And Charlie Munger, Warren Buffett's longtime business partner, has this amazing quote. He says, fish where the fish are. And he gives this example. He says, you know, if you're a fisherman and you see a large pond and all around the pond there's a whole bunch of fishermen, and they're all elbowing each other out of the. Out of the way. They're all using the best lures, the best fishing line. You know, they all have amazing strategy. You actually want to walk off into the forest and find a small fishing hole with lots of fish and very little competition. And I think that's probably the most important thing in business is actually to find those niches where you can actually make real money. Because competition equals lower margin. The more competitors there are, the lower your prices have to be, and the more competitive the business is, ultimately, it.

Doesn'T feel intuitive to go after small markets and to find niches. So let's just follow that thread. Well, why is that actually a source of some of the best ideas starting really small and niche?

I don't necessarily think it has to be something that is small forever, but it has to be something that, like I think about if you're a first time entrepreneur or a student or something, you don't want to walk into the gym on day one and try and deadlift £300, right? So when someone comes to me and they're a first time entrepreneur and they say I'm going to make the next great AI company or you know, I'm going to launch a new bank or something like that, something that is very, very rigorous and complicated and highly competitive and regulated, I think that is the equivalent. I think you really want to take the baby weights and, and start slowly building your muscle. And I think about my own experience starting a business. I was so lucky because the first business I ever started, my web design agency, which became Metalab, that was so easy. And it worked. It worked immediately because all I had to do was know how to build websites and be able to talk to potential customers. And then once they said, you know, yes, I will pay you $5,000, I just had to send them an invoice, do the work. And that was it. It was a very simple business. And because of that I got immediate positive feedback and I built my own narrative. And my narrative was, I'm good at business, I can do this, keep going. And then I went off and I started taking my money that I made from that original business. And that's when I fucked up. So I went out and I started a pizzeria and I lost all my money. I started a designer cat furniture business, a online dj, school, a skin cream business, all of these things. I've just lost all my money almost immediately. But because I had that first win, I kept on going. And I just think it's so critical that people choose a business where they get that initial win.

Okay, this is a great topic. This is just like, how do you avoid creating a job for yourself you hate? There's a lot of business opportunities and ideas that like, yeah, you can make this work and then works and then you're stuck doing this thing, running a restaurant. My wife tells a story where a friend started a coffee shop and then he's like, I thought I was starting a coffee shop, but I'm just replacing milk and buying milk all day. That's my job now. So just kind of along those lines to help people avoid creating a beast that they didn't expect. Any advice for. Just how to know this is maybe even though this may work and make money, you probably don't want to be spending your life doing this sort of business.

So, like, I just started a pressure washing business. I was speaking at a local business school and after I spoke, one of the kids walked up to me and he said, hey, I'm an entrepreneur. I've started two or three businesses in the past doing landscaping and I'm not enjoying school. And so just on the spot I said to him, why don't you drop out and we'll start a business together? And I'd kind of been cooking on this idea of a pressure washing business because I'd studied that industry a little bit and I knew a few friends who'd done it in other cities. And I had this unfair advantage, which is I owned a whole bunch of media properties where I could advertise it for free, basically. And so we started this business and I think for him, he kind of had this moment of, do I really want to be washing people's driveways for the rest of my life? And what I said to him is, look, if this gets to scale, you'll never touch a pressure washer. And unless you want to, you know, if the business can get big enough where you can have employees, he can just focus on sales or digital marketing or whatever aspect of the business that he really loves. I think that's the biggest thing that a lot of entrepreneurs miss. You know, they say, I don't want to do that for the rest of my life. I don't want to, you know, be in the back of a dry cleaner, dry cleaning clothes. And to me, it's just a question of scale. I think the cafe is a great example because a cafe, if it doesn't get to a reasonable scale, is just a job. There's a big difference between a business and a job, right? I think if you, you could start a pressure washing business where you're the only employee, yeah, that's a job. But if you can get to a scale where you can drive 10 leads a day, then you don't have to do any of the pressure washing and you just do what you love. So I think a lot of people have this kind of Protestant work ethic where they think, well, I've got to be the person to do everything. And I think they really need to lean into what I call lazy leadership, which is, how do I get away from the things I hate as quickly as humanly possible, how do I be teflon for tasks?

It's interesting that this business is non software related at all, this pressure washing business. So I guess just for folks that are coming up with ideas, and I imagine most ideas are, there's like a pull to make it software oriented, something AI is going to help build for you and help you run. What's your calculus on just going down a direction of like real world physical business, like a restaurant, power washing business versus software. Just like what are the benefits of that direction? When should someone actually seriously think about doing a business like a power washing business?

I think if someone's listening to this podcast, odds are they're someone who's kind of a digital native. And I think the question is, what's your unfair advantage and what are you great at? So for me, I think I have reasonably good taste. And so what I could do is identify and I knew enough to identify great design and development talent. But mostly I was lucky because I was a talker. I was good at meeting with clients and selling myself. And so ultimately my highest and best use, my superpower was sales. And so that can be applied to anything, anything where you need to go out and you need to sell a customer. And so really it just comes down to what do you get drawn to and then how do you find the profitable business within that. So here's an example. A friend of mine, he owns a restaurant and he said, oh, like I love it. It's so, I'm so passionate about it. It's this stunning, beautiful restaurant in my hometown. And he said, you know, but it's really just a job for a few different people and we can't make any money at it. But I've been noticing that there's all these vendors that service the restaurant and those guys are making a killing. And so he told me about a business that cleaned grease traps, another one that cleans exhaust vents for kitchens. So I think looking around and seeing where your passion is and then sniffing around within it, probably somewhere within your passion there's an opportunity. So for example, I love movies. My happy place is a dark theater. You know, this the best way for me to de stress is go to a dark theater and watch a movie and get lost in it. And probably about four or five years ago I was like, man, how cool would it be to invest in movies in some way to be a part of that creative world? And so I started looking into funding movies and I realized that when you fund movies like 90% of the time, you lose all your money. And even if you do make some money, you rarely make a good return. But I kind of spent a bunch of time understanding the industry and learning about it. And then two years ago, I was in New Zealand and I met the founder of letterboxd. And I realized, oh, my God, this is a business where this has a moat, so it has a network effect. It's a huge social network for film reviewers. It's something I'm passionate about and it's something that we can buy at a fair price. And so all those things came together and I was like, oh, my God, I can invest in film now. So. And in the same way I used to be a barista, we ended up buying the aeropress coffee maker company. So I kind of follow my passions and spend a long time learning different industries and then I find the profitable niche within.

Okay, this is a great takeaway. Essentially, when you're thinking about startup ideas, make sure there's some connection to something unique to you where you have some unfair advantage. This makes me think about Brian Armstrong. He came, he. I saw him do a talk once and he gave this really amazing insight about why. Why Coinbase did well and why he started Coinbase. And it's because if you look at his background, he had this weirdly rare Venn diagram of background of computer science. And I think it was cryptography and economics, which is the exact set of skills you need to start something like Coinbase. And so I think the tip there is just what is that unique Venn diagram of skills in your background? And just ideally, what you're building connects to that and gives you an unfair advantage?

Well, yeah, I mean, like I just met some. Another UVic student at the local university. Student, you know, she is interested in marketing and so she's gone out and she's found some local clients, so small restaurants and stuff and manage their social media. And she kind of said, yeah, it's okay, I can make a thousand bucks a month, but it's a lot of work and you know, the owners really want a lot for their money. And I said, well, you know, if you just pivot that idea just ever so slightly, and instead of doing restaurants, you did realtors or wealth managers who have quite a large marketing budget and are used to spending serious money and it only has to work a little bit to make a lot of money for them. Those people, you can charge $5,000 a month. So I think often it's you find your passion, you know, your skill Set you zero in, and then you just kind of pivot and you find the most profitable way to do it. Like, when I started my web design firm, I started mostly with local and small projects. But very quickly I found a job board in San Francisco where startups would share projects they needed help with. I could charge five times the amount for five times less work.

This point about fish, where the fish are, I think is really important. You can start something that's awesome, that you love, that you're so excited about, but nobody needs it. Talk a bit more about just what that looks like. What have you seen when you're thinking about ideas that tell you that there's fish, but also not overfished, as he pointed out?

I think it's hard. Like, Warren Buffett has this great quote, I'm a better businessman because I'm an investor, and I'm a better investor because I'm a businessman. And I feel like in order to know what problems are valuable to solve, you kind of need to have valuable problems. So it's a bit of a hard thing because, you know, I remember when I was like, 20, I would say, I hate how ugly all the cat furniture I can buy for my cats is. I bet people would pay a lot of money to solve this. But I didn't understand anything about the realities of that business model. I didn't understand how little people were actually willing to pay. I didn't there. I just. I didn't have enough life experience to go, yes, that's actually a worthwhile opportunity. And I think that being able to know what people would pay to solve the problem realistically is incredibly valuable. So my example of a realtor selling a house, because I've studied that industry, I know that a realtor can make like 20 to $50,000 selling a single house. So I can intuit that they'd be willing to spend a lot of money if I have a unique way of getting them. Clients that'll buy houses, that'll convert at a high conversion rate that is worth $5,000 a lead, maybe, Right? So. So I think you kind of have to, like, understand the problem in depth before you really know. Because when I was starting out, I would go down every rabbit trail, you know, every infomercial idea I had I would think was genius.

For people that don't. I don't know, that don't have this experience, which is most people. Is there. Is there one thing you do, maybe a heuristic that kind of gives you a sense, maybe there's something here Maybe there's a lot of fish. Maybe it's a value problem or. No, this will tell me. It probably isn't.

No, unfortunately, I think it's mostly gut. I mean it's a, it's a like, you know, Munger and Buffett talk about having a whole bunch of mental models in your brain and they form a lattice work, right? And they all kind of piece together. And I feel like for me there's so much of this that is like, it's almost like I'm an AI model and I've trained on all this data of what works and what doesn't and what, you know, what's a good boat and what, what's a bad business, et cetera. And when I see it, I just immediately know. I mean I think all the, all entrepreneurs are so lucky now to be able to go into Claude or ChatGPT and just say, hey, I'm thinking about starting a Botox clinic. Can you break down the numbers? Is this a good business? What's hard about it? What is the regulatory moat? You know, what, what would my payroll look like? I didn't have any of that. And so I started so many incredibly stupid businesses. But I think there's no excuse at this point. You should be able to do it with AI.

That's a really good tip actually. Then there's this point you made about boring is good. That's a really good piece of advice. A lot of people are going after flashy stuff, things they can dem on Twitter. Your advice here is boring is actually a really good thing because fewer people are going after it. Is that the general tip?

Totally. I mean, I think so. I started this business. One of my first called Flow and Flow was basically Asana before Asana came out. So it was a way to manage your to dos and projects with your team in a web app. And we basically did the thing, we made the mistake that so many entrepreneurs make, which is to go after an industry that everybody goes after. You know, just like cafes, everybody has the idea. Man, I wish I could design my own project management system or my own to do system. And not only that, but everybody loves new things, they love jumping around. I know me personally, in the last three years I've probably used three different productivity systems and I love jumping around in them. And I didn't understand that. And I ended up losing $10 million trying to compete with venture backed businesses. And bootstrapping is all my own money. Poured $10 million lit it on fire trying to compete with Asana because I didn't understand how the business world worked really. You know, it's kind of like they had raised, you know, hundreds of millions of dollars and they were run by the co founder of Facebook. And it was a little, little bit like I'm Fiji and I'm deciding I'm going to invade the United States. In retrospect, just completely silly. Now on the flip side, if I'd taken that same amount of energy and I'd instead focused on, let's see, what's a really boring one I've heard about. There was, there was a business I saw recently, they were making $30 million a year and all they did was help people fill out forms to get government assistance in certain programs. So it'd be like, you know, your uncle is disabled and you need to access government funding. They, the process to do it is incredibly time consuming and miserable and you have to fill out all these forms. They just have software that fills out the forms for you and it says, look, you're going to get $20,000 as a grant, pay us a thousand bucks. And that is such a boring, like nobody wakes up and goes, I want to make form filling software, but I think they would if they could make $20 million a year.

Along these lines of just bad ideas, things people shouldn't start. What are a few ideas that you think everyone thinks is going to be a great idea and then they do it and then they always fail.

Well, I think the biggest mistake, I can speak from my own experience. The biggest mistakes I've made business wise have been going into business models where other people have repeatedly failed and thinking, I can do this better. So for example, me and one of my best friends about 10 years ago, we really wanted to start a bar. We just thought it'd be so cool to have a bar where us and all of our friends could go. We, we thought it'd be great for the city. And so we, and we thought, you know, we can run this really high margin because we're tech guys, we know how to build systems, we're good at business. And we were utterly humbled. You know, we realized that we didn't know anything about business compared to someone who runs a pizzeria. If you think about it like my example earlier of if you run a software company, what has to happen? You have to hire a bunch of nerds. They need Internet connections and computers and you need to pay them and you need to coordinate online and everyone can work asynchronously. Nothing has to go right. You know, it's not that complicated. At least at small scale, a pizzeria. It's like if the baker doesn't wake up at three in the morning and start prepping dough, the entire thing is aft. And all along the way there's 100 different failure points from front of house, back of house, the deliveries arriving on time, all these logistics. And, and so I think it's been stuff like that. I, I mean, I also, you know, I got into the news business, the local news business. I ended up buying a, like a old paper in Vancouver and it's the exact same thing. It's like I just can't. You can't take a brilliant management team and change a bad business model. You know, ultimately the business model wins.

This is, this is really good advice. Basically, if there's a bunch of dead bodies in that space, there's probably something there that keeps killing them that you are probably not aware of until maybe somebody figures something out, right? Like once in a while, once in a blue moon, someone's like, okay, here's how we do this. And then it works.

Well, look at Instacart, right? When Instacart came out, everyone said, well, webvan failed. This is never going to work. And we still don't necessarily know if Instacart is a great business. I don't know, I haven't studied it, but I think it was like, okay, enough technology has changed that it can happen. But would it be easier to start Instacart, Amazon or Coupang, or would it be easier to start an enterprise SaaS software company? Definitely the enterprise SaaS software company.

I see. So this is, I guess is the advice there. The thing that is easy to start is the thing you should not do because everyone's going after that.

Well, it goes back to my gym analogy of if you're going to deadlift £300 train for 15 years, right? You should have already had three startups and they should have worked. And you know, you've really built up the reps. And I think that if I was going to start Instacart, you know, that's different than someone who's 20 starting it. Not that I would be good at it, but at least I would know what I'm getting into.

Let's talk about something that is kind of this like endless debate on Twitter. Maybe it's a false dichotomy between lifestyle businesses, kind of bootstrap businesses. This idea of not raising money, just making revenue, living off the revenue versus venture backed venture scale companies feels like you're very Good at the first bucket. And a lot of people, this is their dream. I'm just going to start something. I'll start a lifestyle business, make a few million a year, never raise Money. Who needs VCs? VCs suck. Advice for deciding which route to go with an idea you have.

Well, I think there's this. It's just not true that a quote unquote lifestyle or bootstrap business can't get huge. I mean, we bootstrapped the entire business and now across all of our companies, we do almost $300 million in revenue. Right. So it doesn't, there's no. And the whole time, you know, I had been focusing on taking, you know, starting small businesses, small ideas, simple ideas, often buying small companies and watching them grow really big. And I think that the only difference between what we do and what a venture capitalist does is, is the level of tolerance of burning money on fire. And I just haven't seen that. If we ch. If we choose the right businesses that aren't in incredibly competitive markets or where they have some sort of moat. So what I mean by that is like a great brand or a network effect, like a social network or something like that. There's no, I don't feel we're holding them back by not letting them light a bunch of money on fire because these things naturally grow the numbers. I mean, they're like, you know, balloons. They just go as long as you don't mess them up too much. So I think the decision ultimately comes down to how hairy do you want your big hairy, audacious goal to be? And if you, you know, your big hairy, audacious goal is I'm going to start the next satellite business that, you know, creates some sort of crazy technological revolution. Yes, you're going to have to raise venture capital unless you're already a billionaire or something like that. But if you're wanting to just tinker and solve a problem that you think is not going to be hyper competitive. So for example, that form filling thing or software that just does a narrow thing that doesn't require 20, 30, $40 million to be lit on fire before it can make money, then you know, you can have a wonderful life and build a wonderful company that can scale into the hundreds of millions of dollars if you play your cards right without ever raising money, per the story you.

Shared with Flow, where you were competing against a venture, venture funded company. If there is a venture backed company in this space, is the advice like you're not going to win competing with them, most likely and try to do something else.

Well, look at things. Do you know, things I use things I do too. It's awesome. So, you know, things still exist. And things has existed for 20 years. It's run by, I believe, one or two or three people. Like, it's not a big team, certainly under 10 people. It was, I believe, bootstrapped. And it's just consistently delivered an exceptional product and built up a loyal following. They have their, you know, 10,000 true fans who use it and that's enough for them. But they don't do a lot. They've been very intentional. They don't do any AI stuff, they don't have an API. You know, all they, they, they're not on Android. They're very focused and I think they, they have succeeded. But the question is, what would an MBA or a business professor say about their success? If the measure of success is did they maximize taking as much market share as possible and grow to be as big as possible, then the answer is no. Because Asana and other people have built multibillion dollar companies. It's if the goal is the founder has an incredible life, probably has three houses, flies all over the place, does whatever he wants, has recurring revenue, and he gets to work with headphones on building a beautiful piece of software that people love, then I think he's won. I am generally much more in the camp of the things guy has won, not Dustin Moskovitz. Dustin Moskovitz is just playing a different game than the things guy. And if Dustin Moskovitz was running things, he'd be miserable. And if the things guy was running Asana, he would probably kill himself because he wants to put his headphones on and build.

I wonder why nobody has come. It feels like just with lifestyle businesses, if it's working, you would think somebody would come in with more money and more funding and just eat, eat their lunch. Is the key that the market is too small for a VC to ever be excited and so that's why no one's coming for them?

I think so. I mean, I think things probably. I'm just guessing, I don't know any of the numbers or whatever, but I would assume it makes between 5 and $25 million of revenue, which to a VC is like not even worth considering. Like a VC they want to. For, for a VC to invest in your business, you need to have a story where it's worth 300 million to a billion dollars or more. So it's just not that exciting to them, which again, going back to Fish where the fish are, right. You don't want to be fighting against the commercial fishermen. Right? If you just want to have a little business where you make enough, you know, you get enough fish to feed your family and your village or whatever, find the other fishing hole. Don't go where the trawlers are.

This is great advice if you're trying to start a non venture backed company, is find this metaphor just keeps working for us, which is fish where the fish are, but not where the professional fishermen are. Also, ideally not where there's just like a ton of, I don't know, fishermen from all over the place. I don't know, solo solopreneur fisherman. Okay, coming back to just starting a successful company, what would you say are the keys to an amazing business model and amazing business broadly? Like, what should you be thinking about and looking into? I know you spend a lot of time thinking about this when you're buying companies. What are like a few bullet points that you want to focus on?

What I do for a living is basically buy businesses. So in my early career, I started one business, then I started about 10 more. And then I realized starting businesses was extremely hard. And I, I was doing pretty well. I was making quite a bit of money and I'd sold one of my businesses and I was looking out at the next 10 years and really asking myself, what do I want my career to be and am I happy doing what I'm doing? And the answer was no, I did not like starting businesses and experiencing that failure rate. It was incredibly stressful. And so I picked up a book about investing and I got lucky. The first one I bought, I bought was about Warren Buffett. And for those that don't know, Warren Buffett is kind of, he's counter to every VC kind of hustle culture thing you might hear because he basically just sits quietly in a room and reads all day. Despite owning 260 different businesses and being one of the 10 wealthiest people in the world, his life is incredibly calm. He only does what he wants and he spends most of his time quietly reading. And once or twice a year he makes a big decision to buy a business. And so when I read about Warren Buffett, I just thought, wow, I'm a sucker. I'm running around like a crazy person trying to run all these businesses. Why am I not just buying businesses and letting them run? And so when I'm buying a business, what I'm really looking for is something that I can't mess up right now, Obviously we buy a business, we try not to mess it up. And we're very intentional, actually very odd, in that when Tiny buys a company, we generally just leave them alone. If they already have management in place, we say nothing changes. You know, no one should know that. That we've even bought them. Obviously people know that, but. But really, like, there should be no change whatsoever. The only change that we generally make is if the founder wants to leave the business, then we'll bring in a CEO to run the company. And that's probably the most important decision that we make. So I'm looking for a business, though, where it is so good that it's hard to mess up. And most businesses are very easy to mess up. You know, like, one person leaves and the whole business falls apart because it's held together with dental floss and duct tape. And so I'm really looking for what Warren Buffett would call a moat. So a moat is basically a brand. So that could be a brand like Coca Cola, Tylenol, Advil, something like that. So something that gives you pricing power, where you can consistently charge and you have loyal customers, or where we usually find a lot of opportunity is in network effects. So typically, we're looking for a community that's gotten so big where people don't want to go elsewhere. So, for example, we own letterboxd, which is the largest social network for film lovers. And the question is, if someone else wants to compete with us, why would someone go to their social network that has a small number of users when all their friends are already on letterboxd? And so you see that same kind of thing with Instagram or Facebook or similar. And so we're looking for businesses like that, something that has staying power, that is hard to compete with and that we can hold over the very long term.

It was interesting when Elon bought X, how that was such a test of the power of network effects. If you think about it, back then, he changed the name, so the brand completely changed the team. 80% of the people left, like, what was left. It was the network and the network effect. The simplest way, just for folks that aren't super familiar with network effects, the way I think about it is just Network effect is where every additional user that joins the network becomes more useful for everybody.

There's another moat, which is high switching costs, which I don't really like because it's. It's not really very consumer friendly. But an example might be Salesforce, where no one wants to. They've. They've spent years and they've done all the implementation and trained Everyone on it, and it's kind of the standard. Everybody hates it, but ripping it out and switching is such a pain in the ass that they just won't bother, you know, Know that's another form of sometimes a great business, but again, that's more depressing. I don't love that one.

What's the last company you guys bought?

We bought Serato. So Serato is the largest DJ software company in the world. So if you ever see a DJ playing and they've got a laptop in front of them, probably using Serato to dj.

Wow, that is super cool. What, like a fun thing to be looked into.

I used to. I used to dj, so I was aware of them. And it was one of those moments we talked about earlier where, you know, I understood the business. They had a really interesting moat of this huge, passionate user base and deep hardware integration. And. And I also love DJing. And I was able to analyze the business and, you know, luck comes to the prepared mind and it worked out.

This is another great callback to your excellent piece of advice of just ideally, what you're working on and whether you're starting the company or buying the company is you have a unique unfair advantage or some kind of unique background that connects to that idea. Let me ask you one more question before we shift to a whole different topic. Hint, hint, AI, Something that I know you talk a lot about, something you believe strongly and something you deal with a lot when you buy companies is just as people and the challenges of management and hiring and people. So what have you learned about just how to successfully? I don't know, follow, find amazing people, keep amazing people, help people be more successful within the companies that you operate.

My business partner, Chris has a really great quote. He says, there are no problems. There is only people problems. And so we've found that, you know, you could tell us that there's a disaster that, you know, one of our business units is about to fail or something like that. As long as I'm surrounded by really great smart people, I feel fine. Right? But when we have a bad actor, we have a psycho or a narcissist or a really horrible, difficult person we're dealing with, all bets are off and life becomes incredibly stressful. So I'd say I spend probably 20% of my time just trying to make sure we're filtering people very carefully and ensuring we're working with people that we enjoy. And I could talk about it in the AI. I've done some really interesting stuff to help me screen and identify difficult people. But I've just found that the biggest mistake I made in my early career was I would hire people because I liked them on gut and I would think that I could change them. So it's kind of like in romantic relationships, it never works out well if you, you know, get married to someone and you go, okay, well this is going to be a great relationship as long as I can convert them to Christianity or I can change their parents or their personality or whatever it is. And so I've just found that I've never been able to change someone. I've never. You can never mentor someone out into being a good employee. And the, the kind of heuristic I have is if I ever think, should I fire this person even once, I should fire them immediately. It has always been a signal, at least for me, that when someone's a superstar, I can't imagine firing them. I think it's, it's impossible. The, I'd be lost without them. But when I repeatedly start going, man, is this person going to work out? Almost always within six to 12 months, it doesn't work out. And so I really try and be really direct about stuff like that and just cut when it's not working. So I'd say like the lesson really is hire for what you need. Don't hire just for potential. Which is counter to what a lot of people say. A lot of people say hire for potential and coach them into being whatever you need. I just haven't found that. I think you kind of need to have hire someone who already is fully formed and can do what you need. But again, everyone does it differently.

This is big advice, powerful advice. Is this true? Not just for like the CEOs of the companies you run is for folks under, lower down the ladder too.

Well, for CEOs, one of the most interesting things we've observed is. So I'll give you an example. So we had a CEO come in and we were interviewing them and he my, in my opinion, the business needed to grow via organic marketing. In his opinion, it was enterprise sales. And so when we're interviewing him, he keeps going back to his experience building with enterprise sales. And there's this great saying, to a man with a hammer, everything looks like a nail. And so for him, he's looking at this business and going, enterprise sales. That's the way to grow. I hire him. But I say, look, if we're going to hire you, we need you to do the organic marketing. Lo and behold, of course he goes off and he does the enterprise sales thing. And I've just found that hiring CEOs is like, you're. They're an elephant and you're the rider. They're going to go wherever it is that they want to go. And so listening incredibly carefully to people's words and their experiences, because generally people will do the thing they tell you. So what I look for when I interview a CEO now, I want to be nodding along. I want to go, that's exactly what I would do. Or, that's way smarter than my idea. And then I just leave them alone because I've found that anytime I try and pull. Pull them in a certain direction or coach them or whatever, it just doesn't work. And again, this could be my problem. I might be the world's worst coach and mentor, but for me, that's been what's true.

I imagine there's also an element of they won't love the job if they want to be doing, say, enterprise sales. And then they're like, creating viral TikTok videos all day and tweeting. They're like, what the hell?

I've also found people will shoot themselves in the foot, right? If they. If they. If I tell them an idea in a board meeting and I say, I really need you to try this, it never works because usually they kind of sandbag it, right? They don't really put their heart into it, or they. They're just kind of placating me and they don't want it to work. They want their idea to work. And so I've learned not to do that.

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So the primary tool I use is a tool called Lindy Lindy AI. And what it basically lets you do is build workflows and agents. So it's very simple. You might say, when I get an email in the Gmail API, I want to add an AI agent that reads the email and labels it based on that. Right. Or you can build a crazy Rube Goldberg machine that sends different emails all sorts of different places. So, for example, when I get an email and it's related to my kid's school, one of the big problems I have is that my kid's school sends so many emails. You know, the field trip is on Thursday and you need to bring the following things. And meanwhile, there's parent teacher interviews, and all these things get added to my calendar. The AI agent automatically takes that, puts it onto my calendar, makes sure there's notes for all the things I need to prepare and stuff. So, like, I have just basically tried to take every single thing a human could do in my inbox and automate it with Lindy.

And you're sitting there in Lindy doing this yourself, or do you have people that you've kind of trained to help build these sorts of things for you?

No, I do it myself.

Okay, how many agents, if. If that's the term you want to use, do you have running for you?

Oh, man, I think I probably have not. Not a crazy amount within. Let's see, each. Well, each workflow probably has four or five agents. So, for example, my inbox has four or five agents. And then I have a whole bunch of other. You know, I've got a calendar agent, I've got a meeting Agent, I've got an email agent, I've got a scheduler, I've got CRM. And basically they're all different workflows with a whole bunch of agents within.

Okay. And you're not even, you're not an investor in Lindy, right? You're just a fan, super user.

No, no, fun fact.

I actually am. So this is great.

That's awesome.

Tiny angel investor. So just want to put that out there, which I love that this came up organically. What are a couple other really interesting use cases, workflows you've built that people might be inspired by?

Let me, let me go through the email one a little more. So basically emails come in and the first agent says, does Andrew even need to see this? Like, let's say you're in a thread and you, you've already chimed in and everyone's just saying, cool, that works, I don't need to see that. So it just archives that. Never, never. So that immediately reduces my email by about 20%. Then it decides, is this something that is time sensitive? Is this thing that needs to be dealt with in the next 24 hours and if so, it labels it in a special 24 hour label. So when I go in my email, one of the biggest stresses I find is, is I go, shit, there's 200 emails in here and if I don't go through all of them, I don't know if there's an emergency burning somewhere. So now I do. Then it takes any email or every single email and it decides, is this a simple decision? So for example, let's say you emailed me and you say, hey, do you want to get lunch? So it emails me privately and it says, hey, Lenny wants to get lunch. Do you want to say yes? Do you? You want to say yes, but in a few months, do you want to say no? How do you want to say no? And it gives me multiple choice. I just can say four, number four. And then it'll email you as me and it'll write out a nice thoughtful email or whatever. So stuff like that is like so freaking cool and helpful. And I'd say that it's replaced stuff that my full time, I used to have a full time assistant just working on email that's all completely automated. And there's all sorts of other cool stuff I'm doing there. Other agents, like I'm working on one right now to manage my calendar, which is really complex. I do a lot of scheduling and a lot of rules. I have another really simple one, it adds emojis to every single calendar event. So when I look at my calendar, I've got beautiful little emojis for every single calendar event. Very silly.

What are the emojis like? Do they represent something?

Yeah, so if I write weightlifting, it'll just do like a, you know, a guy weightlifting or whatever. I've got one that. This one's cool. Basically, what it does every time I email someone, it looks them up online. It figures out what city they live in. It checks my CRM in Airtable. It says, okay, I don't know, where do you live in?

In Marin, in the Bay Area.

Okay. So it'd say, okay, you email Lenny, he lives in Marin. It puts in the database, you live in Marin. And then next time I travel to the Bay Area, the agent will see two weeks before and it'll say, I saw. You're going to San Francisco. Here's all the people in San Francisco you should try and have coffee with. Right. So just like all these things that I. Yeah, yeah, exactly. Like all these things that I've dreamed of having my assistant do that my assistant could just never consistently do because she gets distracted. We're doing an event, there's something going on. It's like having the world's most reliable employee who costs 200amonth and works 24 7.

Okay, I want to follow that thread. But first of all, what other tools do you have? What are Lindy's One. What else do you find really useful?

So the other one is Replit. So Replit is basically a vibe coding platform. You can literally go into it and say, you know, I want to make a website for my SaaS software business. Here's a big document with a bunch of details, and it'll go and design a pretty impressive website. But then you can also build web apps now. So you can. You can literally be like, yeah, build a Python web app that does xyz. And the design is getting so good because it uses Cloud4. You can start saying, do it in the style of Stripe, think this through, rewrite all the copy and the tone of David Ogilvy or Malcolm Gladwell or whoever you like. And it does a really incredible job. So what I'm finding is that things that previously would have frustrated me because I would have had to rely on a team of five. I can just do entirely on my own when it comes to web projects and stuff like that. So I'm having a blast with that. That's cool.

So your team replit versus lovable bold V0 is that roughly?

I Mean, they're all great. I just am the most familiar with Replit and I. And it seems like it has the most functionality, like, it has a lot of beef to it. Whereas Lovable and Bolt seem a little more basic. You might have to deal with deployment and stuff in a fiddlier way with them.

Awesome. Okay. Anything else?

Another one I love so Limitless. I don't know if you've seen this.

I've got one of those.

It's really cool. So it, you know, clips to your shirt. I actually just put it on my pocket so no one actually notices that I've got it on usually, and I just have it on all day. And what it does is it just records everything I do. And then I can say, you know, the other day I had a coffee with someone and I'm the kind of person where I go a mile a minute and I say, oh, I'll send you that and I'll do this or whatever. And so at the end of the day, I can just say, hey, what did I promise to people today? Or even better, everyone loves this use case. I have a fight with my girlfriend. And she says, you didn't say that. And I'm able to say, well, actually, you know, you did. And. And you can query it as an LLM so you can say, you're a couple's counselor. Look at this fight. What did each person need? How did it start? What are the key lines? Where did it change? How could you do this better? And so, honestly, from a relationship standpoint, is probably where it's been the most useful. What's cool too, is that has an API. And so eventually, I haven't gotten there yet, but eventually you'll be able to just have it record your entire day and then automatically go into your todoist or whatever it is and add to dos or send emails or whatever you need it to do.

Wow, this is so fun. Uh, or just per your point with the relationship, ask it, what could I have done better today? Where did I. Where did I. Where did the day go downhill?

Yeah. I saw a guy on Twitter, he said, every day I ask it, how could I have been a better dad? And it'll be like, oh, you're, you know, your daughter tried to get your attention about this. You, you know, you should have paid attention or whatever.

And that was with the limitless data. Oh, man, I love that. With the relationship, you didn't go. Or that you were going to go where it's like, oh, but who actually said it? What did you actually say, I love that it became much more wholesome of just like, how could we have communicated better holistically? Okay. My wife actually is like, don't. Don't wear this around.

You just got to wear it really covertly.

It.

Honestly, Honestly, I know it sounds kind of cheesy because you think like, oh, it'll tell her, right? But in reality, usually you're both guilty in the fight. And my girlfriend has actually appreciated it because there's been. Half the time it'll be like, oh, yeah, you know, Zoe kind of said this and it triggered this. But a lot of the time it's me too. And I think I'm totally right. So I find it actually really helpful. Other other tools. I mean, otherwise, it's kind of the basic stack of Claude and ChatGPT and Gemini. And Gemini I use mostly for things that are really large. So, for example, all my medical records, I have trained on Gemini 2.5, just because the other ones can't really go through it all. Claude I use for writing very extensively. I find it's the best for that. And then chatgpt for everything else. In terms of cool things I do. Recently, I went through my entire medicine cabinet and I just took big photos that showed all the different medicines and stuff. And now I can say something like, hey, you know, I'm really tired and stressed out today. What supplement should I take and what dose? Or I'll say, remember. Remember all the medications I'm taking. Whenever I ask you a health question, always remind me in the context of I might be taking that medication. So a few times it said, hey, you shouldn't take this other medication because your genetics say you're not compatible with it and you're already taking this other one. So stuff like that's been really helpful.

For that use case. Do you come back to a specific conversation where you've given it that context? Use a project.

I say remember. I just say, whenever you have. Remember these supplements. This is what I have in my medicine cabinet. Or this is what I take every day.

I see. So just tap into the memory of ChatGPT. Yeah, this is awesome. This makes me remember that I've started to use. And this connects to other points you've been making. I've started to use GPT, ChatGPT, deep research to prep for these conversations. I used to have a researcher who did this for 400 bucks. They did research on every guest that I had 4 to 500 bucks and gave me a whole doc. Here's everything about them. Here's Their background. Here's questions you might want to ask. Deep research is better just as of recently, especially with O3 Pro.

We were talking earlier about agents. I forgot one of my favorite agents. So it looks on my calendar 30 minutes before I meet anyone and it goes on to perplexity and it does a deep dive on the person and it sends me. It goes into my email and it gets the context of the meeting. So often I book meetings three months out, so I usually look at my calendar and I go, who is this person? I don't even remember booking this meeting. It'll text me before and it'll say, here's who you are, here's your background, here's the email context of why we're meeting. And it can. And it basically does all the research for me. So I do the same thing. I also use deep research and say like, give me if I'm meeting them, you know everything about me. What are our commonalities and what are all the fun things we should talk about?

Oh my God. I just, I just want to plug and play all these agents you've built to use them myself. Interestingly, I tried to create an agent to do this research kickoff for me, but I don't think you can automate ChatGPT. Deep research. Okay.

Only complexity. Yeah. Okay.

Okay. Perplexity is great too, but it's different. Okay, so let me follow this thread. I was going down, which is around job displacement. I know you think a lot about this. So with me, this researcher is a contractor I was working with for a few months. I no longer need them. Your assistant, you no longer need thoughts on just the impact we're going to see on jobs as a result of AI.

There's this great William Gibson quote. The future is already here. It's just not evenly distributed. And I think that we are in the palm trio phase. Do you remember the palm tree O when I was see in 2007 I think was that when the iPhone came out? 2007, I'm really bad with 700, something like that. In 2007 there was this device called the Palm Treo and it was like a little PDA with a stylus and it had a little modem attachment. And so what you could do is you could get your email anywhere. And that was this shocking thing. It had a black and white or barely color screen and you could go in and email people. And I remember being walking through the mall buying shoes while answering business emails and going, this is the ultimate freedom. This is incredible. But the problem with that device was. It sucked. You know, you had to use a stylus. It's not a good user experience. And then the iPhone comes out and you're like, okay, this is. This is what I was waiting for. This is the real thing. But I got a little preview with the Palm Treo. And so right now, people like me who have the time to. The time and skillset to nerd out and build the agents can do this. It's just not accessible to everybody. And I think that if it was accessible to everybody in terms of, if you could just open ChatGPT and say, hey, ChatGPT, I run a business. Can you help me? And it started asking you questions and it said, oh, well, you know, you do sales. Do you want me to set up a sales agent? Okay, great. Plug in your HubSpot API now, tell me a few things, and then give me access to all your data. And. And then before you know it, it's just a digital employee that's on the other end of the phone on ChatGPT, just like in the movie her, that you can talk to and it can go do stuff. I think that is kind of the iPhone moment that we're going to have in sometime in the next five years. And so I think that if AI doesn't progress, we will see some serious job displacement, like what you already mentioned, the translators, the researchers, the admin, some assistant jobs. Depending on the kind of work they do, those jobs will definitely be massively affected. But I think pretty quick, all knowledge work jobs could be affected if the models scale in the way that they say they're going to. I mean, if you trust Sam Altman and Dario Amadei, I mean, Dario amadei said by 2027, our models will be smarter than all PhDs in any subject. That is a staggering statement. And he's been a very conservative, kind of almost fearful voice in the AI world. Very cautious to say things like that. And so when he said that, I kind of perked up and started listening carefully. I don't know that that's going to how it's going to play out. He might be trying to fundraise. We have to take it with a grain of salt. But. But if that's true, then I think so many knowledge work jobs are going to change massively.

Okay, there's a lot here. I actually had Mike on the podcast, their cpo, Mike Krieger, and he pointed out that Dario, every prediction he's had so far has been right over the past few years. And so there's reason to listen to his insights. Okay, Andrew, I know you're not going to have all the answers for people, but let me ask you a kind of a two part question for new grads and for people currently in the workforce, say, like, I don't know, senior product manager advice on what they should do, where should they focus, what skills will matter most? What jobs do you think will last? What advice can you give us?

You know, everybody. Ten years ago, do you remember there was this whole movement that we should teach kids how to code? Remember that? So now teaching kids how to code is like teaching kids basic and we have a gui, right? You don't need to learn punch cards and basic programming because or Ms. Dos because we all have keyboards and mice. We don't have to do that. And I feel like coding has really gone away because of that. And I think now people are saying people need to learn how to prompt, which I think is very true for the tool set right now. But I don't know how relevant that is in the future because I think we're still again in the palm trio phase. I think that the AIs will be very good at eliciting what the actual problem you're trying to solve is and reinterpreting it in a way that it can optimize the query to get the right answer and solve the problem. And so I think the fundamental question is do all jobs just become a single prompt? So for example, does a CEO just become grow the business while making the customers happy and turning a profit or something like that? And it is able to actually be an omniscient presence that can run a whole company. Now that's a big I'm someone building AI agents. I can barely get it to reliably do calendar entries and that kind of stuff. So I don't think that's totally imminent. But I can certainly see a world where that's coming. And so the question is, what is one to do when that reality is barreling down at you? For people who have resources, I think there's a lot of things they can do in terms of investment. They can invest in the companies that'll benefit from this. Companies that have a lot of compute or energy or that sort of thing. So that's one thing, but that's not really the question. The question is what do you do if you're a smart 18 year old or 19 year old or whatever? In my opinion, I think the best thing to do right now is to get incredibly good with these tools and utilize them to build enough wealth that you can put the money into diversifying into compute and energy. And I do think that while everybody thinks that, you know, all jobs will go away in five years and robots will be everywhere, people generally overestimate things in the short term and underestimate them in the long term. So I think there's going to be this long window where robotics is not anywhere near good enough to even do like, raking leaves and stuff. And I think there's going to be a ton of opportunity for people to just spin up new businesses that never existed before. Like, I was talking to some friends and we were like, you know, what do you do in a world of abundance where, you know, everything is really cheap and companies operate almost autonomously? I think there's a lot of weird skill sets that we can't imagine right now. Like, for example, just being funny, right? Being funny to hang out with. You know, think about only fans, right? Right now there's this whole idea of only fans or where people are paying for comfort and connection. But in a romantic sense, imagine people did that day to day, they just love hanging out with funny people. So you have a funny guy who you chat with or comes over to your house or whatever it is, I'm making stuff up. Maybe it's a guy who comes to play play pickleball with you or something, I don't know. But I can imagine that in this weird world there's all these weird new jobs. So I think, like, my take is like, things will either be. Things will either be totally fine or they will be terrible and we'll all be dead. And I can't predict which one of those is there. I don't think it's worth thinking about all of us being dead. And so I think it's really just lean into what are the tools? How do you stay cutting edge? How do you build businesses and wealth in this new world? But I am certainly feeling a little bit like all of our brains could be defunct in the next 10 years. And that's kind of a scary thought.

I'm picturing this dystopian world where humans are just going around making jokes.

Well, it's like, where does, where does status come from? Right? In a world of abundance, where does status come from? You know, maybe it is just like having. Being the best at hiking or something.

Well, let me ask you this, because this is where it gets even more real, is just with your kids, what are you encouraging them to learn? What are you encouraging them to get good at? Because that's you know, like, this is the real problem a lot of people are having right now is what will matter in the future. Obviously, we don't know, but what do you. What do you. What are you encouraging them to focus on?

Well, I don't know. I mean, they're so little. They're five and eight. And so really what I'm focused on is making sure they're socialized and they're polite, very basic. So are they comfortable talking to adults? Like, I often send my son whenever he wants something at a cafe. I always make him go up, ask nicely, pay himself, all that kind of stuff. But at this point, you know, I feel like for the first 10 years of life, you're just trying to make sure that they're not traumatized or rude and that I think it's gonna be really interesting when they're 10 +, where they're really aware of this stuff and can start building with these tools. And to be honest, I just don't know. I think I just want them to lean into whatever they're passionate about and go from there, but I have no idea. And to be honest, it's not something I'm worrying about because it's too hard to worry about. I don't know. It's too multivariate this. There's too many ways it can go.

I feel like a core part of your message is just get good with these tools. There's this classic quote, AI won't replace you. It'll be somebody very good. Using AI is going to replace you, at least for a while. And so it feels like a big part of this is just like, use these things. Before we were started recording, we were having a mic issue. And I love you. Just went straight to ChatGPT. ChatGPT. How do I connect this mic to Riverside and make it work?

And.

And I feel like that's just a habit to build is just assume ChatGPT. Go to ChatGPT whenever you have a problem like that. I've been doing that a lot. I was connecting a subwoofer from like, what wire do I need to buy it to connect the subwoofer to the receiver?

Well, the best part about ChatGPT is I used to just get stuck. And I have adhd. So when I get stuck, let's say, like, what's an example? I was. I was redoing my home IT security, right? And what will happen is I'll be in the terminal and I'll enter something, and then something goes wrong and it just keeps erroring and then I'm like, well, I'm out. Like, I have adhd. I can't tolerate this. I don't have. I just. I just lose the thread completely. And ChatGPT allows me to stay on track and go so much further and faster than I ever could before. And I just love, I love not being artificially stopped in your tracks and being able to continue the flow state as a result.

And also I noticed you were using voice mode, which is what I've been using more and more. And I feel like that's something a lot of people sleep on, is just the voice mode where you could talk to it and not have to sit there and type your questions. Okay, so let me go in a different direction. You've been spending a lot of time, you wrote a whole book about this, of just kind of your journey from you call it a barista to billionaire, where you started serving coffee, then you ended up being very successful, then realized that that's not. Didn't make you happy. You're quite unhappy with lots and lots of money. I think a lot of people hear these stories. They see this stuff, they're like, yeah, okay, I sort of get it. But they still do the same sorts of things. They still assume they will be happy once they reach that next goal, that next title, make certain dollar amount. What can you share? What have you learned about just what it actually takes to be happy that you think people are still not really recognizing and still kind of are confused about.

Do you remember when you're in your early 20s? Like you. I remember when I was in my early 20s, I'd always be like, I need to move away to Europe. I need to go discover myself. And I'd be really anxious and stressed out and in an existential crisis. And then I'd fly to Europe to go backpacking or something, and I'd still feel anxious and have my existential crisis. It's just now I'm in Europe, and I think the reality is that whatever is in your brain, whatever that anxiety loop is, doesn't go away just because you have a bigger house or more money in the bank account or you're in Bali or wherever it is. That's a chemical reaction happening inside you that relates to your past and your DNA and all that stuff that creates that soup. And for me, I've always been a very anxious person. I've always worried about tomorrow. I rarely enjoy today. I'm always worrying about what could go wrong in health or my businesses or with my family or whatever. It is. And so when I started my business, all I thought was, I just don't want to work for someone else. If I can just wake up in the morning, do my own thing, make 60k a year, then I'll be happy. So I got that. And then it was, once I make a million dollars a year and I can buy a house, well, I got that. And so on and so on and so on, all the way up to, at one point being worth over a billion dollars. By the way, should redo the title of the book from Barista to Billionaire. Now it's former Billionaire because our stock went down. But, you know, it didn't change anything. Like, I'm still just as anxious as ever. I remember a month ago, I had this day where I was sitting in the sauna and I was stressing about a bunch of business problems and money things, and I had this moment, I stopped myself and I was like, wait a minute, like 10 years ago, I had all the same thoughts and I was stressed out about similar kinds of problems. And our revenue was 20 million bucks or 15 million bucks. Now we're at almost 300 million, and I'm still stressed about the same things. And the saddest part was as I met more and more wealthier people all the way up to multi billionaires, I realized they were all still comparing themselves to their peers, competing over who has what and tracking stuff, and still unhappy that anxiety loop or depression was still in their brain. I remember I had this moment where I met this guy who is a multi billionaire, single digit multi billionaire. And he goes, oh, Jeff Bezos, he's just so rich. And I was like, wait, like, what do you mean you're worth like $5 billion? Like, what can. What can he do that you can. And he goes, he can buy a super yacht. And it's like, what? Like. And you know, you can look at that guy and you can say, oh, that's a wacko, and all the other stuff, but the reality is that we're all just comparing ourselves to our peers. Whatever our peers have that we don't. We feel hard done by. And I remember just thinking like, oh my God, how do I not. How do I avoid becoming this and that? That's the scary reality is no matter how lucky you are, I mean, we're all so fortunate. We. We live in. You know, for me, I live in Canada. I have every opportunity that I ever could have hoped for. And there's people all over the world who have nowhere near what I had growing up. And yet I felt hard done by because in my neighborhood I was the poor kid. I wasn't poor globally. I wasn't even poor based on Canada. But all my friends had big screen TVs and would go to Hawaii and, and I never got to do any of that stuff. My parents were stressed about money, so I feel hard done by.

There's a phrase a friend's financial advisor once shared. The Joneses are doing really well and that's hard to get over. What, so what changes did you make to just be happier? You know, it's hard to give up money. It's hard to give up more money you could make. It's hard to give up things that, you know, that, that money buys. I guess, just. So what, what did you change?

Well, there's a few things. I mean, one was reframing money to some degree to have it be something that wasn't just about feathering my own nest and making it better. So for example, I was talking to a friend who's very wealthy and I was kind of saying like, you know, I. All the feelings I described of, you know, have all this and yet I don't feel better. And he said, well, you know, what are you working for? And I said, well, I guess I'm just working for the numbers to get bigger and, you know, have more employees. And, you know, that's nice. Like our businesses do good things in the world and help more people and stuff, but ultimately it's just to pile up cash. And he said, you know, I've reframed it so that all my money, 90% of my money plus goes into my philanthropic foundation and then it gets given away to great causes. So when I think about working really hard or losing a deal or investment going well, the win isn't for me, the win is about doing something good. So. So I did that and that definitely helped. I also stopped spending as much money. I found that, you know, the more stuff I had, the more houses I had, the more people that directly work for me to manage all that stuff, the less happy I was. You know, I was kind of owned by my stuff. And then I also do a real. I work really hard not to have people. I try not to beat people over the head with it. Like I drive a normal car. I don't bring people to my house until I know them really, really well. I meet them on neutral ground. Like I meet them in a cafe, I dress like a schmo. You know, I just try not to be, you know, a weird, out of touch rich person. But the biggest thing, which is kind of a weird answer, is actually medicating myself. So basically, like, all my life, I've been really anxious. And in 2020, I remember I was watching a movie with my ex wife, and I was looping on, you know, I need to respond to this email. If I don't respond to that email, this person's gonna be mad. And then I realized that I was watching a movie for the last 20 minutes, and I didn't know anything about what was happening in the movie. And then I was going, oh, my God, my. My wife is gonna be mad at me. We're gonna get in a fight. And, you know, I'm projecting all this negative stuff. And. And in that moment, I was like, okay, maybe I do need to try an SSRI or something. This is not sustainable. And so I went to my doctor and I got prescribed with one. And I remember I was so scared of it that I cut it into 10 pieces. I said, I'm just going to take a tiny little piece. And it took me six months after that to try any, but I started taking these pieces every day. And I just noticed that within about three or four days, it was like someone had turned down the volume on the nasty voice inside of me doing all that. And for the first time in my life, I felt relief. I. You know, no amount of money or success or attention or anything else had done what this little tiny yellow pill could do for my mental state. And so now I've been on an SSRI for four and a half years or something like that. And then I also started medicating my adhd. And I would say that my brain went from Times Square to a quiet library. And I think a lot of people are scared of that, but ultimately, most people are acting out something that's going on inside of them. You know, there's a trauma or something medically going on, and that's creating this anxiety, this depression, this feeling. And addressing that is so much more important than trying to get praise from the external world.

Wow. That. It's really powerful. I really. I'm really thankful you're sharing this. The advice most people hear, you know, like, the general, I don't know, culture is just like, no, don't take meds, don't take. Don't medicate yourself. You're gonna. You're. I don't know, there's all these downsides, all this risk. The pharma industry is trying to make money. I love this other perspective of it. It's actually really effective. And Actually makes a big difference in your life. And it may be the only solution.

Well, it's funny, because if you have a headache, I don't think many people say, oh, don't. Don't take Tylenol. You know, you're benefiting Johnson and Johnson, Big Pharma. They go, yeah, you know, you take a Tylenol when you have a headache, or a lot of people have seasonal allergies, and they take antihistamines, and they forget that histamine is not just in your nose. Histamine's in your brain and everywhere in your body. And so when you take an antihistamine or even a Tylenol, you're changing your brain, you're changing the way you think. You're changing everything. And yet, for some reason, people are so scared, myself included, of taking an SSRI or similar medication to treat something that is ruining their life. Like, anxiety was ruining my life every minute of every day. I was convinced that something terrible was about to happen. And even now, medicated, I still have that voice. It's not like that. That. That frankly, beneficial voice that helps you grow your business or whatever becomes unproductive at a certain point. And I think that it is. It's wonderful to be able to actually just get a little bit of solace from it.

Wow. For folks that. I imagine many folks listening are like, oh, man, I should really explore this. What's the best way to explore is to talk to your primary care physician.

Physician. Yeah. I think talking to your doctor. And one. One note, I think a lot of people miss is when I. I was so scared of side effects because you hear about all these horrific side effects of, you know, people lose their libido and feel terrible and stuff. And so I looked into it, and a lot of the side effects are due to the way that people metabolize different drugs. And so you can actually do your 23andMe or similar DNA test, and you can find out how you metabolize different SSRIs. And then I chose one that I could metabolize. Well. And so I've had no side effects or problems. And I know every time I mention this, I get a lot of people that say exactly what you say. You know, big pharma and all this other stuff. But I just ask everyone listening, if you take a Tylenol or you take an antihistamine or other medications. I don't know why, you know, something that can be so profoundly helpful is something that people need to be afraid of.

Amazing. Andrew. We've covered so much ground. I love the spectrum of topics we've gone after. Is there anything else that you wanted to share? Anything you wanted to double down on any last nugget you want to leave listeners with before we get to a very exciting lightning round?

So one, one thing that was kind of shocking for me was I was doing, my doctor asked me to get a cognitive test, not because I had any problem, but he said, look, it's really important to get a baseline in your 30s, but because then as you age, we can make sure that you're not getting Alzheimer's or dementia or whatever. So I go and I do this test with a neurologist and she asked me a bunch of questions. You know, it's remember these 10 digits and say them backwards and all this stuff. And finally when I get my test results back, she said, look, your crystallized intelligence, your ability to remember stuff, long range is totally fine. You're above average. Your short term memory, your working memory is 10th percentile, very, very bad. And you probably should get checked for adhd. And I was like, nope, there's no way I don't have adhd. I'm organized. I've got to do lists. I built a business. I wasn't the hyper kid in school or anything like that. And she said, well, look, just humor me, just go get tested. And so I went through this crazy process. They were, you know, you can go online and just quickly get tested or whatever. But I went through this really, really, you know, like kind of five day process to get tested. And it turned out that I do have it. And it's really interesting because if you take the normal population, about 5% of people have ADHD, but about 30% of entrepreneurs have ADHD. And many entrepreneurs I talk to, they love new things. They love jumping around between a million different topics. They're an inch deep and a mile wide like I described. And they describe themselves as unemployable. And I frankly, I remember I was so skeptical of ADHD that when my girlfriend told me a friend of hers got diagnosed with it, I sarcastically said, oh good, she better take some method, right? Talking about stimulant drugs, some. I previously I was very, very skeptical of adhd. But it is a real brain disorder. If you actually dig into it. It's very, a very real thing, very objective that people have poor executive function. And for me it's given me a lot more empathy for myself and my behaviors. Because at work if you have adhd, you can delegate to other people and build systems to get around your disability, but at home, that's where it really plays out. And so for me, it's like my girlfriend asked me to take the garbage out and I say, of course, and then I forget three times in a row. And she views that as, you are being very hurtful and you're not caring for me. And it causes all sorts of different problems at home. And so for me, not only did it make my work life better because I was more focused, but it actually really helped me in my personal life. And it made me feel not broken. I always felt a bit broken. I couldn't put my finger on why, but I just went, I'm not good at doing all the things everyone else seems to be able to do. No problem. And so I think, especially because you have an entrepreneur audience, I think a lot of entrepreneurs should consider getting checked for ADHD. Just go in ChatGPT, say, ask me a bunch of questions and tell me if you think I might have it. But. But I was very surprised. And that's been really impactful for me too, man.

This garbage story is very descriptive of my life. And so I'm going to do this. Oh, boy. There's kind of this implication that it's good to know this. Right? Like, people would be like, it feels scary to feel like, oh, shit, I might get diagnosed with hd. Your advice, I imagine, is like, you'd actually. It's better to know. And you could, because you could do stuff about it.

Totally. I think it's. It's like any medical thing. Right? It's like a. There's an Alzheimer's gene. Right. And if you know you have it, there's a lot you can do to slow the disease or prevent maybe getting it or whatever. I think it's always better to know, even if you don't medicate. I think there's a lot of lifestyle interventions, dietary interventions, and just things you can do to make your life easier, even if it's just explaining to your partner, hey, I need things to be explained to me this way so that I can be effective in loving you.

Beautiful. Okay, well, Andrew, with that, we've reached our very exciting lightning round. I've got five questions for you. Are you ready?

Let's go.

First question. What are two or three books that you find yourself recommending most to other people?

If I could only recommend two, I would recommend the Laws of Human Nature by Robert Greene. It's basically like a compendium of every single type of personality disorder or psychological effect. How do people warp their minds to make bad decisions. Uh, what is a narcissist? What is a psychopath? All that kind of stuff. And Robert Greene does such a great job of telling all that in a really engaging way by using storytelling. So every single chapter has a story about someone with that personality disorder. Um, so I love that book. The other one that I love is a book by Felix Dennis called How to Get Rich. It's hilarious because the whole book starts out saying, I got rich and I regret it, and I wish that I'd become a poet. And instead he went off and he built this huge publishing empire, became a poet in his 60s, and then he died of throat cancer. So it's his story. He basically says, I'll tell you how to build the business, even though you probably shouldn't. And I read that when I was in my 20s, and I found it so exciting and inspiring. And then I recently reread it and I was like, oh, my God, why didn't I listen to this guy? Like, everything he said came true.

Next question. Do you have a favorite recent movie or TV show that. That you have really enjoyed?

I love Challengers. I don't know if you've seen it, but it's amazingly acted. Amazing cinematography. It's like this amazing, like, romantic triad tennis movie. Really, really good.

Do you have a favorite product you recently discovered that you really love? You already mentioned Limitless. Is there anything else?

I'm one of those people who really believes in the idea of a robot vacuum. I've probably spent, like $10,000 on different robot vacuums over the years. Probably five or six of them. And I finally got one that actually works. It's called the Matic Vacuum M A T I C. And basically, I think it's like former Google engineers basically built, like, a mini Waymo car. So it has, like, machine vision, and it will avoid absolutely everything and never get tangled. And it can mop your floors and vacuum. I've been super impressed with it so far.

I've got one of these myself. Completely agree. My wife loves it, which she. I did not expect. She's like, turn that matic on. It's, like, very delightful. It has this little personality, and it just does a really good job. And I'm not an investor, and that's awesome. I'm a huge fan. Okay, next question. Do you have a favorite life motto that you often come back to find useful in work or in life?

Yeah. My favorite is a quote by Jersey Gregory. It's easy choices, hard life. Hard choices, easy life. And I often find that anytime that I'm making the easy choice, my life gets hard. And when I make the hard choice to shut down the business, fire the person, you know, say bye to a project that I was excited about, it's almost always the right choice, and it makes my life a lot easier.

Final question. Okay, so let me know if this is true. I. I found that when you were a teenager, when you're running Mac Teens, you interviewed Steve Jobs at a conference. That true?

So when I was a teenager, I had a tech news website, and I emailed the Apple PR people and I said, hey, could I interview Steve Jobs? And they kind of laughed at me. Like, they're like, yeah, there's no way you're not going to interview Steve Jobs. But, hey, why don't you go to this tour of the Apple Store? So this is. No other Apple Store has existed. This is in New York at Macworld, back in, like, 2004. No, 2003, something like that. And so I was really excited about that. So I show up to go do this tour, and there's like 30 other journalists there, and I'm first in line. And this big black SUV pulls up, and this man gets out, and the man is wearing gray New Balance, little circular John Lennon glasses, the mock turtleneck. And my brain finally puts it together, and I realize it's Steve Jobs. And. And he walks directly up to me because I'm first in line, and he shakes my. My hand and he says, hi, I'm Steve. And I'm like a quivering mess. You know, I'm 17 years old. I. He's my hero. He is my Jesus. And so I was just so high on adrenaline that I just started asking him questions as soon as we walked in. I basically just stayed at his side and I just picked his brain about all sorts of different stuff. So it's not like I got to ask him questions about life. I was asking him about, you know, the new 17 inch iMac or whatever. But it was a pretty cool experience to get to meet him.

That is awesome. There's such a funny thread recently with guests. Everyone's. There's like a Steve Jobs connection for the past couple months of guests. That's an awesome story. It just shows that you, you know, it wasn't luck. You made this happen. You got there first. First in line.

The lesson for me was ask big and maybe you'll get something great. You know, ask for. Ask for Amazing. You'll get something great. Which. Which I did the door.

Door in the face technique. I think people Call it.

Yeah.

Andrew, this was incredible. Two final questions. Where can folks find you if they want to reach out? I know you're buying companies, investing in companies, so just talk about what you're looking for there in case people are like, oh, this is me. And then finally, how can listeners be useful to you?

Yeah, my, my business is Tiny T I N y dot com and we buy businesses. We, we basically, when we sold the business, we hated it. We went through this process where we talked to all these douchebags that were private, you know, ran private equity firms and would show up in our office in suits and, you know, use a bunch of words we didn't understand. And we ended up going, man, why can't we just sell to somebody who's like us? And so we basically started tiny to become the buyer we wish we could have sold to. And we're looking for businesses that have some of the qualities I mentioned before. So, you know, really high quality businesses that do something positive in the world and have happy customers, happy employees, and some kind of competitive advantage that will make them continue into the future. So we own like aeropress, letterboxd Dribble, which is like a design social network, whole bunch of businesses like that. So if somebody is thinking about selling their business, definitely get in touch.

Amazing. Okay, and then how can listeners be useful to you if it's not just that?

I just would say if there's anyone really interesting coming to Victoria, Canada, which is where I live, send me an email and would love to have coffee with you. I just, I, I, the reason I love going on podcasts is because I get to meet so many interesting people, both randomly. Like, if I'm in a cafe and someone sees me and says hi, I often make a lot of friends that way or if someone comes to my hometown. So yeah, just get in touch.

Amazing. Andrew, thank you so much for being here.

Yeah, thanks, dude. That was fun.

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