YouSaid · the spoken record

Andrew Wilkinson

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100
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2025-07-03
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2025-07-03
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1
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podcast

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

    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

  2. “A design social network, a whole bunch of businesses like that. So if somebody is thinking about selling their business, definitely get in touch.”

    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

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

    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

  4. “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 I did.”

    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

  5. “No, 2003, something like that. And so I was really excited about that. So I show up to go do this tour. And there's like 30 other journalists there. And I'm first in line. And this big black SUV pulls up and this man gets out. And the man is wearing gray new balance, little circular John Lennon glasses, the mock turtleneck. And my brain finally puts it together and I realize it's Steve Jobs. And he walks directly up to me because I'm first in line and he shakes my hand and he says, hi, I'm Steve. And I'm like a quivering mess. You know, I'm 17 years old. He's my hero. He is my Jesus. And so I was just so high on adrenaline that I just started asking him questions as soon as we walked in. I basically just stayed at his side and I just picked his brain about all sorts of different stuff. So it's not like I got to ask him questions about life.”

    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

  6. “So, when I was a teenager, I had a tech news website and I emailed the Apple PR people and I said, hey, could I interview Steve Jobs? And they kind of laughed at me. Like they're like, yeah, there's no way you're not going to interview Steve Jobs. But hey, why don't you go to this tour of the Apple store? So this is no other Apple store has existed. This is in New York at Macworld back in like 2”

    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

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

    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

  8. “One of those people who really believes in the idea of a robot vacuum, I've probably spent like $10 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 M8. 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.”

    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

  9. “I love challengers. I don't know if you've seen it, but it's amazingly acted, amazing cinematography. And it's like this amazing, like romantic triad tennis movie. Really, really good.”

    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

  10. “And I read that when I was in my 20s, and I found it so exciting and inspiring. And then I recently reread it. And I was like, oh my God, why didn't I listen to this guy? Like everything he said came true.”

    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

  11. “If I could only recommend two, I would recommend 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? What is a narcissist? 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. So I love that book. The other one that I love is a book by Felix Dennis called How to Get Rich. It's hilarious because the whole book starts out saying I got rich and I regret it. And I wish that I'd become a poet. And instead he went off and he built this huge publishing empire, became a poet in his 60s, and then he died of throat cancer. So it's his story. He basically says, I'll tell you how to build the business, even though you probably shouldn't.”

    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

  12. “Totally. I think it's like any medical thing, right? It's like there's an Alzheimer's gene, right? You know you 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 hey I need things to be explained to me this way so that I can be effective in loving you”

    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

  13. “Better because I was more focused, but it actually really helped me in my personal life and it made me feel not broken. I always felt a bit broken. I couldn't put my finger on why, but I just went, I'm not good at doing all the things everyone else seems to be able to do, no problem. And so I think especially because you have an entrepreneur audience, I think a lot of entrepreneurs should consider getting checked for ADHD. Just go 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.”

    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

  14. “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. Previously, I was very, very skeptical of ADHD. But it is a real brain disorder. If you actually dig into it, it's a very real thing, very objective that people have poor executive function. And for me, it's given me a lot more empathy for myself and my behaviors because at work, if you have ADHD, you can delegate to other people and build systems to get around your disability. But at home, that's where it really plays out. And so for me, it's like my girlfriend asked me to take the garbage out and I say, of course. And then I forget three times in a row. And she views that as you are being very hurtful and you're not caring for me and it causes, you know, all sorts of different problems at home. And so for me, not only did it make my workplace.”

    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

  15. “Organized. You know, I've got to do lists. I built a business. I wasn't the hyper kid in school or anything like that. And she said, well, look, just humor me. Just go get tested. And so I went through this crazy process. They were, you know, you can go online and just quickly get tested or whatever. But I went through this really, really, you know, like kind of five-day process to get tested. And it turned out that I do have it. It's really interesting because if you take the normal population about 5% of people have ADHD, but about 30% of entrepreneurs have ADHD, and many entrepreneurs I talk to, they love new things. They love jumping around between a million different topics. They're an inch deep and a mile wide like I described, and they describe themselves as unemployable. And frankly, I remember I was so skeptical of ADHD that when”

    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

  16. “So one thing that was kind of shocking for me was I was doing my doctor asked me to get a cognitive test, not because I had any problem, but he said, look, it's really important to get a baseline in your 30s, because then as you age, we can make sure that you're not getting Alzheimer's or dementia or whatever. So I go and I do this test with a neurologist and she asks me a bunch of questions. Remember these 10 digits and say them backwards and all this stuff. And finally, when I get my test results back, she said, look, your crystallized intelligence, your ability to remember stuff long range is totally fine. You're above average. Your short-term memory, your working memory is 10th percentile, very, very bad. And you probably should get checked for ADHD. And I was like, nope, there's no way. I don't have ADHD.”

    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

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

    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

  18. “Frankly, beneficial voice that helps you grow your business or whatever becomes unproductive at a certain point. And I think that it's wonderful to be able to actually just get a little bit of solace from it.”

    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

  19. “Funny because if you have a headache, I don't think many people say, oh, don't take Tylenol. You're benefiting Johnson and Johnson, Big Pharma. They go, yeah, you take a Tylenol when you have a headache or a lot of people have seasonal allergies and they take antihistamines and they forget that histamine is not just in your nose. Histamine is in your brain and everywhere in your body. And so when you take an antihistamine or even a tylenol, you're changing your brain. You're changing the way you think, you're changing everything. And yet for some reason, people are so scared, myself included, of taking an SSRI or similar medication to treat something that is ruining their life. Like anxiety was ruining my life every minute of every day. I was convinced that something terrible was about to happen. And even now, medicated, I still have that voice. It's not like that benefit.”

    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

  20. “Nasty voice inside of me doing all that. And for the first time in my life, I felt relief. No amount of money or success or attention or anything else had done what this little tiny yellow pill could do for my mental state. And so now I've been on an SSRI for four and a half years or something like that. And then I also started medicating my ADHD. And I would say that my brain went from Times Square to a quiet library. And I think a lot of people are scared of that. But ultimately most people are acting out something that's going on inside of them. You know, there's a trauma or something medically going on and that's creating this anxiety, this depression, this feeling. And addressing that is so much more important than trying to get praise from the external world.”

    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

  21. “And in 2020, I remember I was watching a movie with my ex-wife and I was looping on, you know, I need to respond to this email. If I don't respond to that email, this person's going to be mad. And then I realized that I was watching a movie for the last 20 minutes and I didn't know anything about what was happening in the movie. And then I was going, oh my God, my wife is going to be mad at me. We're going to 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. And so I went to my doctor and I got prescribed with one. And I remember I was so scared of it that I cut it into 10 pieces. I said, I'm just going to take a tiny little piece. And it took me six months after that to try any. But I started taking these pieces every day. And I just noticed that within about three or four days, it was like someone had turned down the volume on the net.”

    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

  22. “The win isn't for me. The win is about doing something good. So I did that, and that definitely helped. I also stopped spending as much money. I found that, you know, the more stuff I had, the more houses I had, the more people that directly work for me to manage all that stuff, the less happy I was. You know, I was kind of owned by my stuff. And then I also do a really, I work really hard not to have people I try not to beat people over the head with it. Like I drive a normal car. I don't bring people to my house until I know them really, really well. I meet them on neutral ground. Like I meet them in a cafe. I dress like a schmo. You know, I just try not to be, you know, a weird, out of touch, rich person. But the biggest thing, which is kind of a weird answer, is actually medicating myself. So basically, like all my life, I've been really anxious.”

    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

  23. “While there's a few things, I mean, one was reframing money to some degree to have it be something that wasn't just about feathering my own nest and making it better. So, for example, I was talking to a friend who's very wealthy and I was kind of saying like, you know, all the feelings I described of, you know, have all this and yet I don't feel better. And he said, well, you know, what are you working for? And I said, well, I guess I'm just working for the numbers to get bigger and, you know, have more employees. And, you know, that's nice. Like our businesses do good things in the world and help more people and stuff. But ultimately, it's just to pile up cash. And he said, you know, I've reframed it so that all my money, 90% of my money plus goes into my philanthropic foundation. And then it gets given away to great causes. So when I think about working really hard or losing a deal or investment going well,”

    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

  24. “Been 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.”

    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

  25. “Like $5 billion, like, what can he do that you can't? And he goes, he can buy a super yacht. And it's like, what? And, you know, you can look at that guy and you can say, oh, that's a wacko and all the other stuff. But the reality is that we're all just comparing ourselves to our peers, whatever our peers have that we don't, we feel hard done by. And I remember just thinking like, oh my God, how do I not how do I avoid becoming this? And that's the scary reality is no matter how lucky you are. I mean, we're all so fortunate. We live in, you know, for me, I live in Canada. I have every opportunity that I ever could have hoped for. And there's people all over the world who have nowhere near what I had growing up. And yet I felt hard done by because in my neighborhood, I was the poor kid. I wasn't poor globally. I wasn't even.”

    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

  26. “10 years ago, I had all the same thoughts and I was stressed out about similar kinds of problems and our revenue was 20 million bucks or 15 million bucks. Now we're at almost 300 million and I'm still stressed about the same things. And the saddest part was as I met more and more wealthier people all the way up to multi-billionaires, I realized they were all still comparing themselves to their peers, competing over who has what and tracking stuff and still unhappy that anxiety loop or depression was still in their brain. I remember I had this moment where I met this guy who is a multi-billionaire, single digit multi-billionaire and he goes, oh Jeff Bezos, he's just so fucking rich and I was like wait like what do you mean you're worth?”

    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

  27. “I'm always worrying about what could go wrong in health or my businesses or with my family or whatever it is. And so when I started my business, all I thought was I just don't want to work for someone else. If I can just wake up in the morning, do my own thing, make 60K a year, then I'll be happy. So I got that. And then it was once I make a million dollars a year and I can buy a house. Well, I got that and so on and so on and so on all the way up to at one point being worth over a billion dollars. By the way, should redo the title of the book from Breast to the Billionaire. Now it's former billionaire because our stock went down. But it didn't change anything. Like I'm still just as anxious as ever. I remember a month ago I had this day where I was sitting in the sauna and I was stressing about a bunch of business problems and money things.”

    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

  28. “Remember when you're in your early 20s, I remember when I was in my early 20s, I'd always be like, I need to move away to Europe. I need to go discover myself. And I'd be really anxious and stressed out and in an existential crisis. And then I'd fly to Europe to go backpacking or something. And I'd still feel anxious and have my existential crisis. It's just now I'm in Europe. And I think the reality is that whatever'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 your past and your DNA and all that stuff that creates that soup. And for me, I've always been a very anxious person. I've always worried about tomorrow. I rarely enjoy tomorrow.”

    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

  29. “The best part about ChatGPT is I used to just get stuck and I have ADHD. So when I get stuck, let's say like, let's say example, 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 erring. And then I'm like, well, I'm out. Like I have ADHD. I can't tolerate this. 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 not being artificially stopped in your tracks and being able to continue the flow state as a result.”

    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

  30. “Well, I don't know. I mean, they're so little. They're five and eight. And so really what I'm focused on is making sure they're socialized and they're polite, very basic. So are they comfortable talking to adults? Like I often send my son, whenever he wants something at a cafe, I always make him go up, ask nicely, pay himself, all that kind of stuff. But at this point, I feel like for the first 10 years of life, you're just trying to make sure that they're not traumatized or rude. I think it's going to be really interesting when they're 10 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. 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.”

    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

  31. “Well, it's like, where does status come from in a world of abundance? Where does status come from? Maybe it is just like having being the best at hiking 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

  32. “in this new world, but I am certainly feeling a little bit like all of our brains could be defunct in the next 10 years. And that's kind of a scary thought.”

    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

  33. “Skill sets that we can't imagine right now. Like, for example, just being funny, right? Being funny to hang out with them. You know, think about OnlyFans, right? Right now, there's this whole idea of OnlyFans 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 plays play pickleball with you or something. I don't know, but I can imagine that in this weird world, there's all these weird new jobs. So I think like my take is like things will either be totally fine or they will be terrible and we'll all be dead. And I can't predict which 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.”

    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

  34. “In my opinion, I think the best thing to do right now is to get incredibly good with these tools and utilize them to build enough wealth that you can put the money into diversifying, into compute and energy. And I do think that while everybody thinks that all jobs will go away in five years and robots will be everywhere, people generally overestimate things in the short term and underestimate them in the long term. So I think there's going to be this long window where robotics is not anywhere near good enough to even do like raking leaves and stuff. And I think there's going to be a ton of opportunity for people to just spin up new businesses that never existed before. Like I was talking to some friends and we were like, you know, what do you do in a world of abundance where everything is really cheap and companies operate almost autonomously? I think there's a lot of weird.”

    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

  35. “Grow the business while making the customers happy and turning a profit or something like that. And it is able to actually be an omniscient presence that can run a whole company. Now that's a big, I'm someone building AI agents. I can barely get it to reliably do calendar entries and that kind of stuff. So I don't think that's totally imminent, but I can certainly see a world where that's coming. And so the question is, what is one to do when that reality is barreling down at you? For people who have resources, I think there's a lot of things they can do in terms of investment. They can invest in the companies that will benefit from this, companies that have a lot of compute or energy or that sort of thing. So that's one thing.”

    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

  36. “Everybody 10 years ago, do you remember there was this whole movement that we should teach kids how to code? Remember that? Now, teaching kids how to code is like teaching kids basic and we have a GUI, right? You don't need to learn punch cards and basic programming because, or MS-DOS, because we all have keyboards and mice, we don't have to do that. And I feel like coding has really gone away because of that. And I think now people are saying people need to learn how to prompt, which I think is very true for the tool set right now, but I don't know how relevant that is in the future because I think we're still, again, the palm trio phase. I think that the AIs will be very good at eliciting what the actual problem you're trying to solve is and reinterpreting it in a way that it can optimize the query to get the right answer and solve the problem. And so I think the fundamental question is, do all jobs just become a single prompt? So for example, does a CEO just become”

    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

  37. “They say they're going to. I mean, if you trust Sam Altman and Dario Amade, I mean, Dario Amade said by 2027 our models will be smarter than all PhDs. So in any subject, that is a staggering statement. And he's been a very conservative kind of almost fearful voice in the AI world, very cautious to say things like that. And so when he said that, I kind of perked up and started listening carefully. I don't know that that's going to how it's going to play out. He might be trying to fundraise. We have to take it with a grain of salt. But if that's true, then I think so many knowledge work jobs are going to change massively.”

    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

  38. “You know, you do sales. Do you want me to set up a sales agent? Okay, great. Plug in your HubSpot API. Now tell me a few things and then give me access to all your data. And then before you know it, it's just a digital employee that's on the other end of the phone on ChatGPT, just like in the movie Her that you can talk to and it can go do stuff. I think that is kind of the iPhone moment that we're going to have sometime in the next five years. And so I think that if AI doesn't progress, we will see some serious job displacement like what you already mentioned, the translators, the researchers, the admin, some assistant jobs, depending on the kind of work they do, those jobs will definitely be massively affected. But I think pretty quick, all knowledge work jobs could be affected if the model scale and the way 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

  39. “That was this shocking thing. It had a black and white or barely color screen, and you could go in and email people. And I remember being walking through the mall, buying shoes while answering business emails and going, this is the ultimate freedom. This is incredible. But the problem with that device was it sucked. You know, you had to use a stylus. It's not a good user experience. And then the iPhone comes out and you're like, okay, this is what I was waiting for. This is the real thing. But I got a little preview with the palm trio. And so right now people like me who have the time to 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 in terms of if you could just open ChatGPT and say, hey, ChatGPT, I run a business. Can you help me? And it started asking you questions. And it said, oh, well.”

    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

  40. “This great William Gibson quote The future is already here. It's just not evenly distributed. And I think that we are in the palm trio phase. Do you remember the palm trio? So, when I always see in 2007, I think, was that when the iPhone came out, 2007? Something like that. In 2007, there was this device called the Palm Trio. And it was like a little PDA with a stylus. And it had a little modem attachment. And so what you could do is you could get your email anywhere.”

    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

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

    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

  42. “I'm really tired and stressed out today. What supplements should I take and what dose? Or I'll say remember all the medications I'm taking whenever I ask you a health question, always remind me in the context of I might be taking that medication. So a few times it said, hey, you shouldn't take this other medication because your genetics say you're not compatible with it and you're already taking this other one. So stuff like that's been really helpful.”

    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

  43. “You just got to wear it really covertly. Honestly, honestly, I know it sounds kind of cheesy because you think, oh, it'll tell her, right? But in reality. Usually you're both guilty in the fight, and my girlfriend has actually appreciated it because there's been half the time it'll be like, oh yeah, you know, Zoe kind of said this and it triggered this, but a lot of the time it's me too. And I think I'm totally right. So I find it actually really helpful. Other tools, I mean, otherwise it's kind of the basic stack of Claude and Chad GPT and Gemini. Gemini I use mostly for things that are really large. So for example, all my medical records, I have trained on Gemini 2.5 just because the other ones can't really go through it all. Claude, I use for writing very extensively. I find it's the best for that. And then ChatGPT for everything else. In terms of cool things I do, recently I went through my entire medicine cabinet and I just took big photos that showed all the different medicines and stuff. And now I can say something like, hey,”

    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

  44. “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 daughter tried to get your attention about this. You should have paid attention 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

  45. “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.”

    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

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

    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

  47. “I mean, they're all great. I just am the most familiar with Replit, and it seems like it has the most functionality. Like it has a lot of beef to it, whereas Lovable and Bolts seem a little more basic. You might have to deal with deployment and stuff in a fiddlier way with them.”

    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

  48. “So, the other one is Replit. So Replet is basically a vibe coding platform. You can literally go into it and say, you know, I want to make a website for my SAS software business. Here's a big document with a bunch of details and it'll go and design a pretty impressive website. But then you can also build web apps now. So you can literally be like, yeah, build a Python web app that does XYZ. And the design is getting so good because it uses Cloud 4. You can start saying do it in the style of Stripe, think this through, rewrite all the copy and the tone of David Ogilvy or Malcolm Gladwell or whoever you like. And it does have really incredible job. So what I'm finding is that things that previously would have frustrated me because I would have had to rely on a team of five. I can just do entirely on my own.”

    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

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

    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

  50. “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 Airtable. It says, okay, I don't know where do you live?”

    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