I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny)

0:00 You don't want to walk into the gym on day one and try and deadlift three hundred pounds. So when someone comes to me and they're a first time entrepreneur and they say, I'm gonna 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 Fish 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 two hundred dollars a month and works twenty-four-seven. 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 CO of Tiny, a holding company that's often called the Berkshire Hathaway of the Internet. They own over 40 businesses, ranging from dribble to Wommer to the AeroPress Coffee Maker. And they focus on buying profitable businesses from founders and holding them for the long term.

1:12 Andrew and his co-founder bootstrap the business from zero to hundreds of millions of dollars in value, and Andrew personally was worth over one billion dollars 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.

2:02 Including Bolt. Linear, superhuman, notion, perplexity, granola, and more. Check it out at Lenny's Newsletter dot com and click bundle. With that. I bring you. Andrew Wilkinson.

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3:55 Like customer centric industry leaders like Canva, Notion, Perplexity, and Linear, reach out to the team at interpret.com Slash Lenny. That's E N T E R P R E T dot com slash Lenny. Andrew, thank you so much for being here. Welcome to the podcast.

4:15 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 wanna 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

4:28 Startup idea. And uh 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 spent a lot of time thinking about. I feel like you've actually

4:42 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 Seventy five different projects or businesses where I've been a primary

5:02 Contributor. And I wouldn't say that's anything to brag about. Because I've been an inch deep and a mile wide. Um, 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.

5:14 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 gonna be interested in. But I think a mistake a lot of people make is

5:34 They choose Something that everything is everybody is interested in. So For example they say I I don't know anyone that has the had the thought Man, I would love to start like a really cool restaurant.

5:46 Or You know, I want to have a cool cafe or something. And what in reality what they think about is how cool would it be to come up with a ba an amazing logo. Or You know, all the fun stuff, design the logo the menu and stuff. But in reality

6:01 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

6:16 You know what, I'd love to start a funeral home. Or I would like to start a past 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,

6:32 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.

6:41 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. Uh, you know, they all have amazing strategy. You actually want to walk off into the forest and find a small

6:57 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

7:10 Equals Lower margin. The more competitors there are The lower your prices have to be and the more competitive. the businesses ultimately.

7:19 It doesn't feel uh Intuitive. to go after small markets and to find niches. So let's just follow that thread. We'll Why is that actually a source of some of the best ideas starting really small and niche? I I don't necessarily think it has to be something that is

7:33 Small forever. But it has to be something that Like I think about if if you're a first time entrepreneur or a student or something You don't want to walk into the gym On day one.

7:45 And try and deadlift three hundred pounds. Right. So when someone comes to me and they're a first time entrepreneur and they say I'm gonna make the next great AI company or You know, I'm gonna launch uh a new bank or something like that. Something that is very, very rigorous and complicated and highly competitive and regulated.

8:05 I think that is the equivalent. I think you really want to take the baby weights 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.

8:21 That Was so easy. And it worked. It worked immediately. Because all I had to do was Know how to build websites.

8:30 And be able to talk to Potential customers. And then Once they said, you know, yes, I will pay you five thousand dollars. I just had to send them an invoice, do the work, and that was it. It was a very simple business.

8:41 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.

8:54 uh 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.

9:06 A online DJ school. Uh 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

9:20 They get that initial win. Okay, this is a great topic. This is Just like how do you avoid creating a job for yourself that you hate? business opportunities and ideas that like, yeah, you can make this work.

9:32 And then you work and then you're stuck doing this thing, running a restaurant. Like uh my wife tells a story where a friend Uh replacing milk and buying milk all day. That's my job now. So just kind of along those lines. To help people avoid

9:48 creating a beast that they o didn't expect. Any advice for just how to No, 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

10:08 I'm an entrepreneur. I've started two or three businesses in the past, um, 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?

10:20 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 Uh we started this business and and I think For him he kinda had this moment of

10:42 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 unless you want to.

10:55 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. You know, they say I don't wanna do that for the rest of my life. I don't wanna You know, be in the back of a dry cleaner, dry cleaning clothes.

11:17 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

11:34 Yeah, that's a job. But if you can get to a scale where you can drive ten 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.

11:46 Where they think, Well, I've gotta 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 power pressure washing business. So I guess just for folks that are coming up with ideas. And

12:08 I imagine most ideas are There's like a pull to make it software oriented, something AI is gonna help build. For you and help you run. What's your calculus on Just

12:17 going down a direction of like real world physical business, like A restaurant. Power washing. business versus uh 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

12:38 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.

12:48 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

13:00 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

13:10 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.

13:22 And he said, Oh, like I love it. It's so I'm so passionate about it. It's this stunning beautiful uh restaurant in my hometown. And He said, you know.

13:34 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.

13:45 And those guys are making a killing. And so he told me about a business that cleans grease traps, another one that cleans uh exhaust fence for kitchens. So I think looking around and seeing where your passion is

14:00 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.

14:16 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

14:28 Funding movies. And I realized that when you fund movies Like ninety percent of the time you lose all your money. And even if you do make some money, you rarely make a good return. But

14:39 I kind of Spend a bunch of time understanding the industry and learning about it. And then Uh two years ago I was in New Zealand. And I met the founder of Letterboxd.

14:50 And I realized, Oh my God, this is a business where Uh, 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 Aero Press coffee maker company.

15:12 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 What are you thinking about? Start up ideas. Make sure there's some connection to something

15:25 unique to you where you have some unfair advantage. This makes me think about Brian Armstrong. He can he I saw him do a talk once and he gave this really amazing Insight about why Uh

15:36 Why Coinbase did well. And why he started Coinbase and it's because If you look at his background, he had this weirdly rare van diagram of background of computer science. And I think it was cryptography and economics.

15:49 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 UVX student

16:05 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 managed their social media. And she kinda 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.

16:26 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 And it only has to work a little bit to make a lot of money for them.

16:42 Those people you can charge five thousand dollars a month, so I think. Often it's You find your passion, you know your skill set, you zero in and then you just kinda 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.

17:01 Where startups would share uh 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.

17:24 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

17:36 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 twenty I would say um 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

17:57 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 I just I didn't have enough life experience to go Yes, that's actually a worthwhile opportunity. And I think that

18:13 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.

18:25 I know that a realtor can make like twenty to fifty thousand dollars 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 five thousand dollars a lead, maybe, right? So

18:45 So I think you kinda 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 um infomercial idea I had I would think was genius.

18:59 Or 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 kinda gives you a sense, maybe there's something here, maybe there's a lot of fish. Maybe it's a value prom 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.

19:21 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.

19:39 I mean I think all the all entrepreneurs are so lucky now To be able to go into Claude or chat GPT 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

19:56 Uh 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.

20:09 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 demo 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 um So I started this business.

20:26 Uh one of my first Called flow. And flow was basically a sauna before Asana came out. So it's a way to manage Your to do's and projects with your team. Uh in a web app.

20:39 And We Basically did the thing, we made the mistake that so many entrepreneurs make. Which is To go after an industry

20:49 That everybody goes after. You know, just like Cafe's 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 I love jumping around in them.

21:10 And I didn't understand that, and I ended up losing ten million dollars. Trying to compete with venture backed businesses and bootstrapping. It's all my own money. Poor ten million dollars lit it on fire. trying to compete with Asana because I didn't understand how the the business world worked really

21:26 You know I was kind of like They 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 gonna invade the United States in retrospect. Just completely silly. Now On the flip side.

21:42 If I take in 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 Thirty million dollars a year. And all they did was help people fill out forms.

21:58 to get government assistance in certain programs. So it'd be like uh, 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 gonna get twenty thousand dollars as a grant. Pay us a thousand bucks. And that is such a boring

22:22 Like nobody wakes up and goes I want to make form filling software. But I think they would if they could make twenty million dollars a year. Along these lines of just bad ideas, things people shouldn't start What are a few ideas that you think everyone Think it's gonna be a great idea and then they do it and then they always fail.

22:37 I think the biggest mistake I can speak from my own experience, the biggest mistakes I've made in business wise have been Going into business models where other people have repeatedly failed. and thinking I can do this better. So for example

22:52 Me and one of my best friends about ten 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 thought it'd be great for the city. And so we and 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.

23:14 You know, we realize 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.

23:28 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

23:41 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 a hundred different failure points from Front of house, back of house, the deliveries arriving on time, all these logistics. And so I think it's been stuff like that. I I mean I also

24:00 you know, I got into the news business, the local news business. I ended up buying a like a old paper uh 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.

24:17 You know, ultimately the business model wins. This is uh 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 gonna work. And we still don't necessarily know if Instacart is a great business. I don't I don't know. I haven't studied it, but But I think it was like okay, enough technology has changed.

24:48 Amazon or Coupang, or would it be easier to start an enterprise SaaS software company? Definitely the Enterprise uh software company. Mm. I see. So this is

25:02 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 gonna deadlift three hundred pounds, train for fifteen 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 gonna start Instacart.

25:25 You know, that's different than someone who's twenty 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 style businesses. Kind of bootstrap businesses this idea of not raising money, just making revenue, living off the revenue.

25:44 versus venture back, venture scale companies. Feels like you're Uh very good at the first bucket. And Uh a lot of people, this is their dream. I'm just gonna start something, I'll start a lifestyle business, make a few million a year.

25:56 Never raise money. Who needs VCs? VCs suck. Advice for deciding which route to go with a an idea you have. Well I think um There's this it's just not true. the a quote unquote lifestyle or bootstrap business.

26:12 Can't get huge. I mean we bootstrapped The entire business. And Now across all of our companies we do almost three hundred million dollars in revenue.

26:23 Right. So it doesn't there's no And the the whole time. you know, I had been focusing on Taking You know.

26:31 Starting small businesses, small ideas, simple ideas, often buy 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 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

26:53 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 up a bunch of money on fire because these things naturally Grow.

27:12 The numbers I mean they're like you know, balloons. They just go. Uh as long as we 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?

27:24 And if you You know, your big Harry Audacious goal is I'm gonna start the next satellite business that You know, create some sort of crazy technological revolution. Yes, you're gonna have to raise venture capital unless you're already a billionaire or something like that.

27:40 But if you're Wanting to just tinker and Solve a problem that You think is not going to be hyper competitive.

27:49 So for example, that form filling thing or software that just does a narrow thing that doesn't require twenty, thirty, forty million dollars 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.

28:06 If you play your cards right without ever raising money. The story you share with Flo where you were competing against a venture fail uh venture funded company. If there is a venture. Fact company in the 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 um things. Do you know things? Items. I do too.

28:27 It's awesome. So You know, things still exists and things has existed for twenty years. It's run by I believe one or two or three people like it's not a big team, certainly under ten people. It was, I believe, bootstrapped.

28:42 And It's just consistently Delivered an exceptional product. And built up a loyal following. They have their

28:51 You know, ten thousand 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 all they they've d they're not on Android.

29:04 They're very focused. And I think they They have succeeded. But The question is

29:11 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 the answer is no, because Asana and other people have built multi billion dollar companies. If the goal is the founder has an incredible life Probably has three houses.

29:34 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 one. I am generally much more in the camp of the things guy has won, not Dustin Moscovitz.

29:50 Dustin Moscov Moscovits is just playing a different game than the Things guy. And if Dustin Moscowits was running things He'd be miserable. And if the things guy was running Asana Human

30:01 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. And 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 V C to ever be excited. And so that's why no one's coming for them.

30:21 I think so. I mean I think things Probably I'm I'm just guessing. I don't know any of the numbers or whatever, but I I would assume it makes between five And twenty five million dollars of revenue. Which to a V C is like not even worth considering. Like a V C They want to you for for a V C to invest in your business.

30:39 You need to have a story where it's worth three hundred 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 con uh fighting against the commercial fishermen. Right. If you just wanna 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 back company is find

31:08 Uh this metaphor just keeps working for us, which is Uh fish where the fish are, but not where the professional fishermen are. Also ideally not where there's just like a ton of Uh I don't know, fishermen from all over the place. I don't know. So premier fishermen. Okay. Coming back to just starting a successful company.

31:25 What would you say are the keys to An amazing business model. an 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

31:42 In my early career, I started one business. Then I started about ten 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 ten years and really asking myself,

32:01 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.

32:21 Warren Buffett. Is kind of He's counter to every V C kind of hustle culture.

32:30 Because he basically just sits quietly in a room And reads all day. Despite owning Two hundred and sixty uh different businesses and being one of the ten wealthiest people in the world. His life is incredibly calm.

32:44 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?

33:02 And so When I'm buying a business What I'm really looking for is something that I can't Mess up.

33:10 Right. Now, obviously we buy a business, we try not to mess it up, but 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 any that we've even bought them. Uh, obviously people know that, but but really like there should be no change whatsoever.

33:31 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.

33:44 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.

33:57 And so I 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.

34:08 Tylenol. Advil, something like that. So something that gives you pricing power where you can Consistently charge And you have loyal customers. Yeah.

34:19 Uh 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.

34:30 So for example, we own Letterboxed, 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? It has

34:43 A small number of users. When all their friends are already on Letterboxed. 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.

34:57 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 eighty percent of the people left. Like what was left? It was the network and the network effect.

35:17 And the 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 er becomes more useful for everybody. There's another moat which is high switching costs, which I don't really like'cause it's It's not really very consumer friendly. But an example might be Salesforce.

35:36 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, 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?

35:58 Uh we bought Serato. So Serrato 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 Serrato to DJ. Wow.

36:10 That is super cool. What a like a funding to be willing to. I used to I used to DJ, so I 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 a really interesting mode of this huge passionate user base and deep hardware integration. And uh and I also love Djang and I

36:30 was able to analyze the business and you know, luck comes to the prepared mind and it worked out. This is a another great call back to your I've just got to be a little bit more. ideally what you're working on 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.

36:48 Let me ask you one more question before we shift to a whole different topic, uh hint hint AI. Something that I know you talk a lot about, something you believe strongly, and something you deal with a lot is when you buy companies is just Is people And the The challenges of

37:03 Uh management and hiring and People. So what have you learned about just uh how to successfully, I don't know, 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

37:18 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?

37:36 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 twenty percent of my time just trying to make sure we're filtering

37:52 people very carefully in ensuring we're working with People that we enjoy Uh, 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 like them.

38:09 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 gonna 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

38:30 I've never been able to change someone. I've never you can never mentor someone out 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?

38:43 I should fire them immediately. Uh, 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. I'd be lost without them. But when I repeatedly start going Man, is this person gonna work out?

39:00 Almost always within six to twelve months, uh, 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.

39:21 I just haven't found that I I think you kinda need to Have hire someone who already is fulfilled and can do what you need. But again. Everyone does it differently. This is big advice, powerful advice. Is this is this true not just for like the COs of the companies you you run is for folks under lower down the ladder, too?

39:39 Well, for CEOs one of the most interesting things we've observed is So so I'll give you an example. So We had a CEO come in and we were interviewing them. And he

39:50 My in my opinion. The business needed to grow. via organic marketing. In his opinion It was enterprise sales.

39:59 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 gonna hire you We need you to do the organic marketing.

40:19 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

40:29 You're they're an elephant and you're the rider. They're gonna 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 wanna be nodding along.

40:47 I wanna go, that's exactly what I would do, or that's way smarter than my idea. And then I just leave them alone. Because any time 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 a price sales and then they're like

41:12 Creating viral TikTok videos all day and tweeting there, like what the hell? Well 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.

41:33 They want their idea to work. And so I've learned not to do that. This episode is brought to you by Miro. Every day new headlines are scaring us about all the ways that AI is coming for our jobs, creating a lot of anxiety and fear. But a recent survey for Miro tells a different story. Seventy six percent of people believe that AI can benefit their role. But over 50% of people struggle to know when to use it.

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42:33 Help your teams get great work done with Miro. Check it out at Miro.com to find out how. That's M I R O. Let's talk about AI. Uh It's so funny to watch you on Twitter. Clearly you've become AI obsessed, AI pilled, I don't know what the term is. And I love that you're not just

42:49 The kind of person that just talks about it and tweets pontifications, you're like clearly using it in like every facet of your job and looking for more ways to use AI. So I have a lot of questions here,'cause I think this is where more and more founders are gonna be, where you are today. First of all, just what's in your AI stack these days? Like what are the tools you find yourself coming back to most or finding are you most useful? So the primary tool I use is a tool called Lindy.

43:13 Lindy. Uh 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 Uh I want you I want to add an AI agent that reads the email and labels it.

43:31 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, uh when I get an email and it's related to my kids' school. One of the big problems I have is that My kids 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.

43:55 The AI agent automatically takes that, puts it onto my calendar. make sure there's notes for all the things I need to prepare and stuff. So like I have just but basically tried to take every single thing a human could do in my inbox and automate it with Lindy. And you're sitting there inland doing this yourself. Uh, or do you have people that you've kinda trained to help build s these sorts of things for you? No, I do it myself. Okay.

44:18 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 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

44:42 uh a scheduler, I've got Uh 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. Fun fact, I actually am, so this is great. Tiny Angel Investors, I just want to put that out there. Which uh I love that this came up organically.

45:02 What are a couple other uh Really interesting use cases, workflows you built. That people might be inspired by. Let me let me go through the email one a little more. So

45:10 Basically emails come in and the first agent says, does Andrew n even need to see this? Like let's say you're in a thread and You've already chimed in and everyone's just saying Cool, that works.

45:24 I don't need to see that. So just archive that. Never never so That immediately reduces my email but by about twenty percent. Then It decides is this something that is Time sensitive.

45:36 Is this thing that needs to be dealt with in the next twenty four hours? And if so, it labels it in a special twenty four hour label. So when I go in my email, one of the biggest stresses I find is I go. Shit, there's two hundred 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 uh or every single email and it decides

45:58 Is this a simple decision? So for example, let's say s you email me and you say Hey, do you want to get lunch? So It emailed me privately and it says, Hey

46:08 Lenny wants to get lunch. Do you want to say yes? Do 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. Like 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

46:29 Cool and helpful. 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

46:42 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 events when I look at my calendar.

46:56 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 and air table. It says, Okay I don't know where where do you live?

47:20 In uh 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 see 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

47:42 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 Employ

47:59 Who costs two hundred dollars a month. And works twenty four seven. Okay. I wanna 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 um replet. So Raplet is basically a vibe coding

48:12 platform, you can literally go into it and say You know, I want to make a website for my Sound software business. Here's, you know, a big document with a bunch of details and it'll go in design. A pretty impressive Website. But then you can also build web apps now.

48:28 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 Cloud Four, you can start saying Do it in the style of stripe. Um, think this through

48:43 rewrite all the copy in 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.

49:00 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. So your team Replit versus Lovable Bull to zero. Is that the thing I think I'm going to I mean they're all great. I I just am the most familiar with Replit, and it seems like it has the most Functionality. Like it has a lot of uh beef to it. Whereas Lovable and Bolt seem a little more basic. You might have to deal with Uh deployment and stuff.

49:27 in a fiddlier way with them. Awesome. Okay. Anything else? Um another one I love. So Limitless? I don't know if you've seen this. I've 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.

49:41 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 I'll send you that and I'll do this or whatever. And so at the end of the day, I can just say

50:00 Hey, what in What did I promise to people today? Or mean b 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.

50:15 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

50:27 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 to doist or whatever it is and add to dos or send emails or whatever you need it to do. Wow. This is so fun.

50:49 Uh or just for 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 your 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 uh data.

51:09 Oh man. I love that with the relationship unico or I thought you were unico, 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. Mm-hmm.

51:21 Okay. My wife actually is like don't don't wear this around. You just gotta wear it really covertly. It honestly honestly I know it sounds kinda cheesy'cause 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

51:40 Half the time it'll be like Oh yeah, you know, Zoe kinda 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 I find it actually really helpful. Other other tools. I mean, otherwise it's kind of the basic stack of Uh Claude and Chad GPT and Gemini.

51:57 And Gemini I use mostly for things that are really um large. So for example, all my medical records I have trained on Gemini two point five, just'cause the other ones can't really Go through it all. Claude I use for writing.

52:12 very extensively, I find it's the best for that. And then chat GPT for everything else. In terms of cool things I do. recently like I went through my entire medicine cabinet and I just took big photos that showed all the different um medicines and stuff. And now I can say something like Hey, um You know, I'm really tired and stressed out today.

52:31 What supplement should I take? And what dose? Uh 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

52:46 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 or say remember. I just say remember. Remember these supplements. This is what I have in my medicine cabinet, or this is what I take every day.

53:10 I see. So just tap into the memory of Chat GPT. Yeah. This is awesome. This makes me uh remembered that I I've started to use and this connects to other points you've been making, I've started to use Chad GPT deep research to prep for these conversations. I used to have a researcher who did this for four hundred bucks. They Did research on every guest that I had.

53:29 Fourty five hundred 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 O three pro. We were talking earlier about agents. I forgot one of my favorite agents. So It looks on my calendar.

53:44 Thirty minutes before I meet anyone. 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

53:59 Who is this person? I don't even remember booking this meeting. It'll text me before 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 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.

54:18 What are our commonalities and what are all the fun things we should talk about? No my god. I just I just want to plug and play all these agents you built. To use them myself. Uh Interestingly, I tried to uh create a an agent to do this research kickoff for me, but I don't think you can

54:33 Automate chat GPT deep research. Okay. Only 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

54:53 Thoughts and just the impact we're gonna see. On jobs. As a result of AI. There's this great Al uh William Gibson quote, The future is already here. It's just not evenly distributed.

55:03 And I think that We are in the palm trio. Faze. Do you remember the palm trio? No. Well when I was

55:12 Let's see, in two thousand seven, I think. Was that when the iPhone came out? Two thousand seven. Something like that. In two thousand seven. There was this device called the Palm Trio, and it was like a little PDA with a stylus. And you it had a little modem attachment. And so what you could do is you could get your email Anywhere.

55:32 And that was this shocking thing. It had a you know, 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.

55:48 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 trio.

56:02 And so Right now people like me who have the time to Mm the time and skill set 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

56:16 In terms of If you could just open chat GPT and say Hey ChatGBT, 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.

56:34 Now tell me a few things and then give me access to all your data. And then before you know it, it's just a digital employee. That's on the other end of the phone on Chat GPT. 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 gonna have in sometime in the next five years. And so I think that if AI doesn't progress We will see

56:59 Some serious job displacement like what you already mentioned, the translators, the researchers, the admin Um, some assistant jobs depending on the kind of work they do. Those jobs will definitely be massively affected. But I think pretty quick.

57:16 All knowledge work jobs could be affected if the models scale in the way that they say they're going to. I mine if you trust Sam Altman And Dario Amade. I mean Dario Amade said

57:30 By twenty twenty seven. Our models will be smarter. Then all PHDs Any so in any subject. That is a staggering

57:41 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 gonna how it's gonna play out. He might be trying to fundraise we have to take it with a grain of salt.

58:00 But if that's true, then I think so many knowledge work jobs are going to change massively. Mm. Okay. There's a lot here. I actually had Mike on the podcast, their CPO, Mike Krieger, and He pointed out that Dario

58:14 Every prediction he's had so far has been right. over the past few years. And so there's reason to listen to his in insights. Okay, Andre, I know you're not gonna have all the answers for people, but let me ask you. A kind of a two part question. For

58:28 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?

58:43 You know, everybody ten years ago, do you remember there's 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.

58:55 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.

59:15 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

59:26 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

59:46 uh grow the business while making the customers happy and turning a profit or or something like that. And it is able to actually be an on 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, you know

1:00:04 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 cutting and so The question is What is one to do?

1:00:14 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.

1:00:29 So that's one thing, but that's not really the question. The question is what do you do if you're a smart eighteen year old or nineteen 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

1:00:48 Into uh 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.

1:00:59 People generally overestimate things in the short term and underestimate them in the long term. So I think there's gonna 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 gonna be a ton of opportunity for people to just spin up.

1:01:16 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 and companies operate almost autonomously. I think there's a lot of

1:01:30 Weird Skill sets. that we can't imagine right now. Like for example Just Being funny.

1:01:37 Right? Being funny to hang out with a m you know, think about OnlyFans, right? Right now there's this whole idea of OnlyFans or 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 his I don't know, but I can imagine that in this weird world

1:02:04 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.

1:02:13 Or they will be terrible and will 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.

1:02:28 But I'm certainly Feeling a little bit Like all of our brains could be defunct in the next ten years and that's kind of a scary thought. I'm picturing this dystopian moral curve.

1:02:39 Humans are just going around making jokes. Mm-hmm. Where is it Where does status come from? Right. In a world of abundance, where does status come from? You know, maybe it is just like having

1:02:50 Being the best at hiking or something. Well let me ask you this,'cause 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 are you what are you encouraging them to focus on?

1:03:09 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.

1:03:25 Pay himself, all that kind of stuff. But at this point You know I feel like for the first ten years of life you're just trying to make sure that they're not traumatized or rude.

1:03:36 And Th I I think it's gonna be really interesting when they're Ten plus. 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

1:03:51 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. 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. Uh AI won't replace you. It'll be somebody very good using AI is gonna replace you.

1:04:13 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. And I love you just went straight to Chat GPT. Chat GPT how do I connect the spike to Riverside and make it work? And I feel like that's just a habit to build is just Assume chat GP they go to chat G P T whenever you have a problem like that. I've been doing that a lot. I was connecting a subware from like

1:04:33 What wire do I need to buy to connect the subwoofer to the receiver? Well the best part about Chat G PT 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.

1:04:55 And then I'm like, Well I'm out. Like I have ADHD, I can't tolerate this. I 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

1:05:10 I love not being artificially stopped in your tracks and being able to continue the flow state as a result. And also, uh, 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.

1:05:30 You've been spending a lot of time, you wrote a whole book about this of just kinda your journey from you called it barista to billionaire, where you Started serving coffee, then you ended up being very successful. Then realize that that's not Didn't make you happy, you're quite unhappy. Uh with lots and lots of money.

1:05:47 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 um when you're in your early twenties? Like you I I I remember when I was in my early twenties, I'd always be like

1:06:16 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.

1:06:26 To go backpacking or something. And I'd still Fex. And have my existential crisis. It's just now I'm in Europe. And

1:06:35 I think the reality is that Whatever's 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

1:06:52 Yeah. 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.

1:07:03 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

1:07:20 Do my own thing. Make Sixty K a year, then I'll be happy. I got that. And then

1:07:27 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 Breeze to the Billionaire. Now it's former billionaire because our stock went down.

1:07:46 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.

1:07:56 And I was stressing about a bunch of business problems and money things. And I had this mo I stopped myself and I was like Wait a minute. Like Ten years ago. I had all the same thoughts.

1:08:08 And I stressed about about similar kinds of problems. And our revenue was twenty million bucks or fifteen million bucks. Now we're at well, you know, almost three hundred million and I'm still stressed about the same things. And the saddest part was As I met more and more

1:08:26 wealthier people All the way up to multi billionaires. I realize they were all still Comparing themselves to their peers. Competing.

1:08:36 over who has what and tracking stuff and still unhappy that anxieto or depression was still in their brain. Uh I remember I had this moment where I meant this. Guy who is a multi billionaire, single digit multi billionaire.

1:08:51 And he goes. Oh, Jeff Bezos, he's just so fucking rich. And I was like wait, like What do you mean you're worth like Five billion dollars. Like what can

1:09:02 What can he do that you can? And he goes. Um he can buy a super yacht. And it's like what? Like the and 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.

1:09:21 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?

1:09:29 And that that's the scary reality is no matter how lucky you are, I mean, we're also fortunate We live in uh, you know For me, I live in Canada. I have every opportunity. That I ever could have hoped for.

1:09:42 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.

1:09:50 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 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.

1:10:07 The Joneses are doing really well. Uh-huh. And that's hard to get over. So what changes did you make? to

1:10:17 Just be happier. It 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?

1:10:28 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

1:10:37 feathering my own nest and making me better. So for example I I was talking to a friend who's a very wealthy And I was kind of saying like, you know, I I 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

1:10:55 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 And he said. You know, I've reframed it so that All my money, ninety percent of my money plus

1:11:13 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 a investment going well. The win isn't for me, the win is about some 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.

1:11:36 The more people that directly work for me to manage all that stuff. the less happy I was, you know, I was kinda owned by my stuff. And then I also Do a real I work really hard not to Have people

1:11:50 I 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 shmo. You know, I just try not to

1:12:05 be uh you know a weird Out of touch rich person. Um 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.

1:12:18 And in twenty twenty I remember I was watching a movie with my ex wife. And I was looping. On

1:12:27 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 twenty 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 in that moment I was like okay. Maybe I do need to, you know, try an SSRI or something. This is not sustainable.

1:12:51 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 ten pieces. I said I'm just gonna take a tiny little piece. It took me six months after that. To try any.

1:13:05 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.

1:13:19 I've 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 S R I for Four and a half years or something like that. And then I also started medicating my ADHD.

1:13:38 And I'd 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.

1:13:49 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

1:14:02 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

1:14:17 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

1:14:34 Don't take Tylenol. You know, you're benefiting Johnson and Johnson big pharma. They go, Yeah, you know, you take a Telenol 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

1:14:53 And antihistamine or a t even a tomanol. 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.

1:15:11 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 benef that frankly beneficial voice that helps you

1:15:27 grow your business or whatever. Becomes unproductive at a certain point. And I think that's a good thing. It is it's wonderful to be able to actually just Get a little bit of solace from it.

1:15:38 Well. For folks that I mentioned 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? Yeah, I think talking to your doctor and one one note I think a lot of people miss his

1:15:51 When I I was so scared of side effects'cause 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. um or similar DNA test and you can find out how you metabolize

1:16:13 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 I 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 Telenol or you take an antiestamine or Other medications. I don't know why

1:16:34 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

1:16:48 You wanted to share anything you wanted to double down on, any last nugget you want to leave listeners with before we get to our very exciting lightning round. So one one thing um It was kind of shocking for me was I was doing I doctor

1:17:02 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 thirties 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 uh test with a neurologist and she asked me a bunch of questions, you know, it's Remember these ten digits and say them backwards and all this stuff. And finally when I got my test results back, she said, Look Your crystallized intelligence.

1:17:28 Your ability to Remember stuff long range. is totally fine. You're you're above average. Your Short term memory.

1:17:38 Your working memory Is Tenth percentile. Very, very bad. And you probably should get checked for ADHD.

1:17:47 And I was like no. There's no way I don't have ADHD. I'm organized. You know, I've got to do lists, I built a business, I've you know, 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 they were

1:18:04 Um, you know, you can go online and just quickly get test it or whatever, but Um, 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

1:18:17 It's really interesting because if you take The normal population about five percent of people have ADHD. But about thirty percent of entrepreneurs have ADHD. And many entrepreneurs I talk to They love new things.

1:18:31 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 sceptical of ADHD.

1:18:45 That when my girlfriend told me a friend of hers got diagnosed with it, I sarcastically said, Oh, good, she better take some meth, right? Talking about stimulant drugs. Some I I previously I was very, very skeptical of AHD. But it is a real brain disorder. If you actually dig into it, it's very uh a very real thing, very objective that people have Poor executive function. And

1:19:07 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

1:19:29 you are being very hurtful and you're not caring for me and it causes, you know, all sorts of different problems at home. And so for me Not only h did it make my work life better because I was more focused on the But It actually really helped me in my personal life.

1:19:46 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 and chat GPT. Say, ask me a bunch of questions and tell me if you think I might have it. But I was very surprised, and that's been really impactful for me, too.

1:20:13 Man, this garbage story is uh Very descriptive of my life. And so I'm gonna do this. Oh boy. Uh 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 H D.

1:20:28 Your advice, I imagine, is like you'd actually it's better to know and you could'cause you could do stuff about it. Totally. It's like any medical thing, right? It's like uh there's an Alzheimer's gene, right? And If you know you

1:20:41 Uh have it. There's a lot you can do to slow The disease or prevent Maybe getting it or whatever. 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.

1:20:59 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

1:21:20 The Laws of Human Nature by Robert Green. 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 nurses, what is a psychopath, all that kind of stuff. And Robert Green 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.

1:21:45 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.

1:21:59 And instead he went off and he built this huge publishing empire. Became a poet in his sixties 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 twenties 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.

1:22:23 Next question, do you have a favorite recent movie or TV show that you have really enjoyed? I love challengers. Uh, I don't know if you've seen it, but it's amazingly acted, amazing cinematography. It's like this amazing uh Like romantic triad tennis movie. Really, really good. Do you have a favorite product you recently discovered that you really love? Uh you already mentioned Limitless. Is there anything else?

1:22:45 I'm one of those people who really believes in the idea of r a robot vacuum. I've probably spent like ten thousand dollars 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.

1:23:09 And it will avoid absolutely everything and never get tangled and it can mop your floors in vacuum. I've been super impressed with it so far. I've got one of these myself. I completely agree. My wife loves it, which she I did not expect. She's like, turn that matic on. It's like very delightful, has this little personality and it just does a really good job. Uh, and I'm not an investor. That's awesome. I'm a huge fan.

1:23:31 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 Gregoric. Um It's easy choices, hard life. Hard choices, easy life. And I often find that

1:23:49 Any time 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.

1:24:07 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 Teams, you interviewed Steve Jobs at a conference. Not true. So when I was a teenager I had a tech news website

1:24:21 And I emailed the Apple PR people and I said, Hey, could I interview Steve Jobs? And they kinda laughed at me like they're like Yeah, there's no way you're not gonna interview Steve Jobs. But um hey.

1:24:34 Why don't you go to this um tour of the Apple store. So this is no other Apple stores existed. This is in New York at Macworld. Back in like two thousand and four? No, two thousand three, something like that. And so I was really excited about that. So I show up to go do this tour.

1:24:52 And there's like Thirty other journalists there. And I'm first in line. And this big black S C V pulls up. And this man gets out.

1:25:01 And the man is wearing Great 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 he walks directly up to me because I'm first in line.

1:25:14 And he shakes my s my hand and he says, Hi, I'm Steve. And I'm like a quivering mess, you know, I'm seventeen 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.

1:25:34 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 seventeen 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. Uh that's an awesome story. It just shows how you you know, you it wasn't luck. You made this happen. You got there first, first in line.

1:25:59 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 uh s door door in the face technique, I think people call it.

1:26:11 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 who what you're looking for there in case people are like, Oh, this is me. And then

1:26:24 Finally, how can listeners be useful to you? Yeah, my my business is tiny, T I N Y dot com. And we buy businesses Uh we s we basically When we sold a business we hated it. We went through this process where

1:26:37 We talked to all these douchebags that were private you know, ran private equity firms that would show up in our office and suits and You know, use a bunch of words we didn't understand. And we ended up Uh going, man, why can't we Just sell to somebody who's like us.

1:26:54 And so we basically started Tiny to become the buyer. Uh, we wish we could have sold two. And uh 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

1:27:16 Aeropress. Uh, Letterboxd, uh Dribble, which is like a design social network, whole bunch of businesses like that. So if somebody uh is thinking about selling their business. Uh definitely in touch. Amazing. Okay, and then how can listeners be useful to you? If it's not just that.

1:27:33 I just would say if there's anyone really interesting coming to Victoria, Canada, which is where I live. Send me an email. And uh would love to have coffee with you. I just I I the reason I love going on podcasts is'cause 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.

1:27:53 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.

1:28:00 Hi everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show. at Lenny's podcast dot com.

1:28:23 See you in the next episode.

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