YouSaid · the spoken record

Andrew Wilkinson

lines on the record: 100
first: 2025-07-03
most recent: 2025-07-03
sittings or episodes: 1
sources: podcast

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“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.”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“Then it decides is this something that is time sensitive? Is this something that needs to be deleted 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 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 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.”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“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've already chimed in and everyone's just saying, cool, that works. I don't need to see that. So just archives that. So that immediately reduces my email by.”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“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”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“So, the primary tool I use is a tool called Lindyndy.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 you. 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 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. 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.”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“I've also found people will shoot themselves in the foot, right? 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'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.”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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.”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“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, 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, they're an elephant and you're the rider. They're going to go wherever it is that they want to go.”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 cod 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 hire someone who already is fully formed and can do what you need. But again, everyone does it differently.”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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. You can never mentor someone out into being a good employee. And 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 impossible. I'd be lost without them. But when I repeatedly start going,”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“My business partner, Chris, has a really great quote. He says, There are no problems. There is only people problems. And so we 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.”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“I used to DJ, so I was aware of them and it was one of those moments we talked about earlier where I understood the business. They had a really interesting mode of this huge passionate user base and deep hardware integration. And I also love DJing and I was able to analyze the business. And luck comes to the prepared mind and it worked out.”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“We bought Cerrado. So Cerrado 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 Cerrado to DJ.”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“There's another moat, which is high switching costs, which I don't really like because it's not really very consumer friendly. But an example might be Salesforce, where no one wants to, 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.”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 Letterbox, 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 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 that is hard to compete with and that we can hold over the very long term.”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“But really, 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.”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“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, no one should know that we've even bought them. Obviously, people know that.”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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 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.”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 five and twenty five.”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“Be as big as possible, then 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, 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. Dustin Moscovit Moscovitz is just playing a different game than the things guy. And if Dustin Moscovitz 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.”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“I do too. It's awesome. So, you know, things still exist and things have 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 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. They're not on Android. They're very focused. And I think 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?”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“Million dollars to be lit on fire before it can make money, then 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.”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“Or a network effect like a social network or something like that. 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. The numbers, I mean, they're like, you know, balloons. They just go 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? 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, 34.”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“Well, I think This is 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 there's no, and the whole time, you know, I had been focusing on taking 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 the level of tolerance of burning money on fire. And I just haven't seen that 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.”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“Well, it goes back to my gym analogy if you're going to deadlift 300 pounds, train for 15 years. You should have already had three startups and they should have worked and 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.”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“We'll look at Instacart, right? When Instacart came out, everyone said, Well, WebFan 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 Would it be easier to start Instacart, Amazon, or Kupang, or would it be easier to start an enterprise SaaS software company? Definitely the enterprise SaaS software company.”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“I mean, I also, you know, I got into the news business, the local news business. I ended up buying an 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.”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“And so we thought 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. 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 3 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.”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“I think the biggest mistake I can speak for my own experience, the biggest mistakes I've made business wise have been going into business models where other people have mistakenly 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”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“Money poured $10 million littered on fire, trying to compete with Asana because I didn't understand how the business world worked really. I was kind of like they had raised hundreds of millions of dollars and they were run by the co-founder of Facebook. And it was a 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 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 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”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“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. It was all my own.”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“No, unfortunately, I think it's mostly gut. I mean, it's a munger and buffet 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's a bad business, et cetera. And when I see it, I just immediately know, I mean, I think 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 mode? 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.”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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.”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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.”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“Well, yeah, I mean, like I just met another UVC 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 managed 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 as 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.”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 Letterboxed. 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.”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 priest traps, another one that cleans exhaust fence 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 is 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.”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 beflon for tasks?”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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.”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 this 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 unless you want.”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 pounds, 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.”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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.”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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, you know, 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 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 past control business or I should start.”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“Definitely had a lot of experiences, and I've probably started or been involved with. 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.”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“It's like having the world's most reliable employ 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?”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“Charlie Munger, Warren Buffett's longtime business partner, has this amazing quote. 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.”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source
“Don't want to walk into the gym on day one and try and deadlift 300 pounds. 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.”
2025-07-03 · Lenny's Podcast · I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · IDENTIFIED FROM THE TRANSCRIPT · source