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

Andrew Wilkinson:You don't wanna 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 gonna make the next great AI company I think that is the equivalent

Lenny Rachitsky: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

Andrew Wilkinson:Charlie Munger Warren Buffett's longtime business partner has this amazing quote

Lenny Rachitsky:Fish where the fish are

Andrew Wilkinson: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

Lenny Rachitsky:It's so funny to watch you on twitter clearly you've become AI obsessed

Andrew Wilkinson:It's like having the world's most reliable employee who costs $200 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

Lenny Rachitsky:Today my guest is Andrew Wilkinson Andrew is the cofounder and CEO of Tiny a holding company that's often called the Berkshire Hathaway of the internet they own over 40 businesses ranging from Dribbble to WeCommerce to the AeroPress coffee maker and they focused on buying profitable businesses from founders and holding them for the long term Andrew and his co founder bootstrapped the business from zero to hundreds of millions of dollars in value and Andrew personally was worth over $1,000,000,000 at one point in our wide ranging conversation we cover a bunch of strategies for coming up with a good business idea what common business ideas you should avoid his experience automating much of his work and life using AI and what that means for employment in the near future also what he's learned about happiness and money and how they are not directly related and also how getting diagnosed with ADHD and then taking SSRIs was the thing that most impacted his happiness in life this is both a powerful and also a very tactically useful conversation and I'm really excited for you to hear it if you enjoy this podcast don't forget to subscribe and follow it in your favorite podcasting app or YouTube also if you become an annual subscriber of my newsletter you get a year free of a bunch of amazing products including Bolt Linear Superhuman Notion Perplexity Granola and more check it out at lennysnewsletter.com and click bundle with that I bring you Andrew Wilkinson This episode is brought to you by Sauce the way teams turn feedback into product impact is stuck in the past vague reports static taxonomies unactionable insights that don't move business metrics the result churn lost deals missed growth Sauce is the AI product copilot that helps CPOs and product teams uncover business impact and act faster it listens to your sales calls support tickets churn reasons and lost deals surfacing the biggest product issues and opportunities in real time it then routes them to the right teams to turn signal into PRDs prototypes and even code that drives revenue retention and adoption that's why Whatnot Linktree Incident IO and ZIP use Sauce one enterprise uncovered a product gap that unlocked $16,000,000 ARR another caught a spiking issue and prevented millions in churn you can too at sauce.app/lenny Sauce built for AI product teams don't get left behind This episode is brought to you by Interpret Interpret is a customer intelligence platform used by leading CXN product orgs like Canva Notion Perplexity Strava Hinge and Linear to leverage the voice of the customer and build best in class products Interpret unifies all customer conversations in real time from Gong recordings to Zendesk tickets to Twitter threads and makes it available for your team for analysis and for action what makes Interpret unique is its ability to build and update a customer specific knowledge graph that provides the most granular and accurate categorization of all customer feedback and connects that customer feedback to critical metrics like revenue and CSAT if modernizing your voice of customer program to a generational upgrade is a 2025 priority like customer centric industry leaders like Canva Notion Perplexity and Linear reach out to the team at interpret dot com slash leni that's e n t e r p r e t dot com slash leni

Lenny Rachitsky:Andrew thank you so much for being here welcome to the podcast

Andrew Wilkinson:Oh thanks man great to be here

Lenny Rachitsky:I've been wanting to chat with you for so long there's so much that I wanna 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 startup idea and this is something that a lot of people are thinking about right now because AI makes it so easy to actually build your idea into something real and I feel like this is something you spend a lot of time thinking about I feel like you've actually started and run more companies than I don't know maybe anyone else in the world I feel like you're in the top 100 top 10 something like that I don't know does that feel right

Andrew Wilkinson:I've definitely had a lot of experiences and I've probably started or been involved with 75 different projects or businesses where I've been a primary contributor and wouldn't say that's anything to brag about because I've been an inch deep and 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

Lenny Rachitsky: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

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

Lenny Rachitsky:It doesn't feel intuitive to go after small markets and define niches so let's just follow that thread well why is that actually a source of some of the best ideas starting really small and niche

Andrew Wilkinson:I 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 if you're a first time entrepreneur or a student or something you don't wanna 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 gonna make the next great AI company or you know I'm gonna launch a new bank or something like that something that is very very rigorous and complicated and highly competitive and regulated I think that is the equivalent I think you really wanna 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 that was so easy and it worked it worked immediately because all I had to do was know how to build websites and be able to talk to potential customers and then once they said you know yes I will pay you $5,000 I just had to send them an invoice do the work and that was it it was a very simple business and because of that I got immediate positive feedback and I built my own narrative and my narrative was I'm good at business I can do this keep going and then I went off and I started taking my money that I made from that original business and that's when I fucked up so I went out and I started a pizzeria and I lost all my money I started a designer cat furniture business a online DJ school a skin cream business all of these things I just lost all my money almost immediately but because I had that first win I kept on going and I just think it's so critical that people choose a business where they get that initial win

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

Andrew Wilkinson:So like I just started a pressure washing business I was speaking at a local business school and after I spoke one of the kids walked up to me and he said hey I'm an entrepreneur I've started two or three businesses in the past doing landscaping and I'm not enjoying school and so just on the spot 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 and I think for him he kinda had this moment of do I really wanna 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 you know if the business can get big enough where you can have employees he can just focus on sales or digital marketing or whatever aspect of the business that he really loves I think that's the biggest thing that a lot of entrepreneurs miss you know they say I don't want to do that for the rest of my life I don't want to you know be in the back of a dry cleaner dry cleaning clothes and to me it's just a question of scale I think the cafe is a great example because a cafe if it doesn't get to a reasonable scale is just a job there's a big difference between a business and a job right I think if you you could start a pressure washing business where you're the only employee yeah that's a job but if you can get to a scale where you can drive 10 leads a day then you don't have to do any of the pressure washing 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 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

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

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

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

Andrew Wilkinson:Well yeah I mean like I just met some another UVic student at the local university student you know she is interested in marketing and so she's gone out and she's found some local clients so small restaurants and stuff and 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 and I said well you know if you just pivot that idea just ever so slightly and instead of doing restaurants you did realtors or wealth managers who have quite a large marketing budget and are used to spending serious money and it only has to work a little bit to make a lot of money for them those people you can charge $5,000 a month so I think often it's you find your passion you know your skill set you zero in and then you just 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 where startups would share projects they needed help with I could charge five times the amount for five times less work

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

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

Lenny Rachitsky:For people that don't I don't know that don't have this experience with just 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 problem or no this will tell me it probably isn't

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

Lenny Rachitsky:That's a really good tip actually then there's this point you made about boring is good that's a really good piece of advice a lot of people are going after flashy stuff things they condemn 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

Andrew Wilkinson: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 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 I love jumping around in them and I didn't understand that and I ended up losing $10,000,000 trying to compete with venture backed businesses and bootstrapping was all my own money poured $10,000,000 lit it on fire trying to compete with Asana because I didn't understand how the the business world worked really you know I was kind of like they they had raised you know hundreds of millions of dollars and they were run by the cofounder 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 if I'd taken that same amount of energy and I'd instead focused on let's see what's a really boring one I've heard about there there was a business I saw recently they were making $30,000,000 a year and all they did was help people fill out forms to get government assistance in certain programs so it'd be like you know your uncle is disabled and you need to access government funding they the process to do it is incredibly time consuming and miserable and you have to fill out all these forms they just have software that fills out the forms for you and it says look you're gonna get $20,000 as a grant pay us a thousand bucks and that is such a boring like nobody wakes up and goes I wanna make form filling software but I think they would if they could make $20,000,000 a year

Lenny Rachitsky:Along these lines of just bad ideas things people shouldn't start what are a few ideas that you think everyone thinks is gonna be a great idea then they do it and then they always fail

Andrew Wilkinson:Well I think the biggest mistake I can speak from my own experience 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 so for example 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 you know we realized that we didn't know anything about business compared to someone who runs a pizzeria if you think about it like my example earlier of if you run a software company what has to happen you have to hire a bunch of nerds they need internet connections and computers and you need to pay them and you need to coordinate online and everyone can work asynchronously nothing has to go right you know it's not that complicated at least at small scale a pizzeria it's like if the baker doesn't wake up at three in the morning and start prepping dough the entire thing is F and all along the way there's a 100 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 you know I got into the news business the local news business I ended up buying a like a old paper in Vancouver it's and 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

Lenny Rachitsky:This is this is really good advice basically if there's a bunch of dead bodies in that space there's probably something there that keeps killing them that you're 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

Andrew Wilkinson: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 that it can happen but would it be easier to start Instacart Amazon or Coupang or would it be easier to start an enterprise SaaS software company definitely the enterprise SaaS software company

Lenny Rachitsky:I see so this is I guess this is the advice there the thing that is easy to start is the thing you should not do because everyone's going after that

Andrew Wilkinson:Well it goes back to my gym analogy of if you're gonna deadlift 300 pounds yeah trust me 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 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

Lenny Rachitsky:Let's talk about something that is kind of this like endless debate on Twitter maybe it's false dichotomy between lifestyle businesses kind of bootstrap businesses this idea of not raising money just making revenue living off the revenue versus venture backed venture scale companies feels like you're very good at the first bucket and a lot of people this is their dream I'm just gonna start something I'll start a lifestyle business make a few million a year never raise money who needs VCs VCs suck advice for deciding which route to go with an idea you have

Andrew Wilkinson:Well I think there's this it's just not true that a quote unquote lifestyle or bootstrap business can't get huge I mean we bootstrapped the entire business and now across all of our companies we do almost $300,000,000 in revenue right so it doesn't there's no and the the whole time you know I had been focusing on taking you know starting small businesses small ideas simple ideas often buying small companies and watching them grow really big and I think that the only difference between what we do and what a venture capitalist does is the level of tolerance of burning money on fire and I just haven't seen that if we if we choose the right businesses that aren't in incredibly competitive markets or where they have some sort of moat so what I mean by that is like a great brand or a network effect like a social network or something like that there's no I don't feel we're holding them back by not letting them light a bunch of money on fire because these things naturally grow the numbers I mean they're like you know balloons they just go as long as 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 gonna start the next satellite business that you know creates 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 but if you're wanting to just tinker and solve a problem that you think is not gonna be hypercompetitive so for example that form filling thing or software that just does a narrow thing that doesn't require $20.30 $40,000,000 to be lit on fire before it can make money then you know you can have a wonderful life and build a wonderful company that can scale into the hundreds of millions of dollars if you play your cards right without ever raising money

Lenny Rachitsky:Per the story you shared with Flo where you're competing against a venture venture funded company if there is a venture backed company in the space is the advice like you're not gonna win competing with them most likely and try to do something else

Andrew Wilkinson:Well look at Things do you know Things

Lenny Rachitsky:I use Things

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

Lenny Rachitsky: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 VC to ever be excited and so that's why no one's come in for them

Andrew Wilkinson: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 VC is like not even worth considering like a VC they want to you for for a VC to invest in your business you need to have a story where it's worth 300,000,000 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 wanna be con 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

Lenny Rachitsky:This is great advice if you're trying to start a non venture backed company is find this metaphor just keeps working for us which is fish where the fish are but not where the professional fishermen are also ideally not where there's just like a ton of I don't know fishermen from all over the place I don't know solo preneur fishermen okay coming back to just starting a successful company 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 wanna focus on

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

Lenny Rachitsky:It was interesting when Elon bought X how that was such a test of the power of network effects if you think about it back then he changed the name so the brand completely changed the team 80% of the people left like what was left it was the network and the network effect 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 becomes more useful for everybody

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

Lenny Rachitsky:What's the last company you guys bought

Andrew Wilkinson:We bought Serato so Serato is the largest DJ software company in the world so if you ever see a DJ playing and they've got a laptop in front of them probably using Serato to DJ

Lenny Rachitsky:Wow that is super cool what a like a fun thing to

Andrew Wilkinson: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 really interesting mode of this huge passionate user base and deep hardware integration and and I also love DJing and I was able to analyze the business and you know luck comes to the prepared mind it worked out

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

Andrew Wilkinson: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 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 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 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 I should fire them immediately it has always been a signal at least for me that when someone's a superstar I can't imagine firing them I think it's it's impossible the I'd be lost without them but when I repeatedly start going man is this person gonna work out almost always within six to twelve months it doesn't work out and so I really try and be really direct about stuff like that and just cut when it's not working so I'd say like the lesson really is hire for what you need don't hire just for potential which is counter to what a lot of people say a lot of people say hire for potential and coach them into being whatever you need I just haven't found that I I think you kinda need to have hire someone who already is fully formed and can do what you need but again everyone does it differently

Lenny Rachitsky:This is big advice powerful advice is this is this true not just for like the CEOs of the companies you you run it's for folks under lower down the ladder too

Andrew Wilkinson: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 my in my opinion the business needed to grow via organic marketing in his opinion it was enterprise sales and so when we're interviewing him he keeps going back to his experience building with enterprise sales and there's this great saying to a man with a hammer everything looks like a nail and so for him he's looking at this business and going enterprise sales that's the way to grow I hire him but I say look if we're gonna hire you we need you to do the organic marketing lo and behold of course he goes off and he does the enterprise sales thing and I've just found that hiring CEOs is like you're they're an elephant and you're the rider they're gonna go wherever it is that they wanna 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 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 I've found that anytime I try and pull pull them in a certain direction or coach them or whatever it just doesn't work and again this could be my problem I might be the world's worst coach and mentor but for me that's been what's true

Lenny Rachitsky:I mentioned there's also an element of they won't love the job if they want to be doing say enterprise sales and then they're like creating viral TikTok videos all day and tweeting they're like what the hell

Andrew Wilkinson: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 they want their idea to work and so I've learned not to do that

Lenny Rachitsky: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 76% of people believe that AI can benefit their role but over 50% of people struggle to know when to use it enter Miro's innovation workspace an intelligent platform that brings people and AI together in a shared space to get great work done Miro has been empowering teams to transform bold ideas into the next big thing for over a decade today they're at the forefront of bringing products to market even faster by unleashing the combined power of AI and human potential teams can work with Miro AI to turn unstructured data like sticky notes or screenshots into usable diagrams product briefs data tables and prototypes in minutes you don't have to be an AI master or to toggle yet another tool the work you're already doing in Miro's canvas is the prompt help your teams get great work done with Miro check it out at miro.com to find out how that's mir0.com let's talk about AI it's so funny to watch you on Twitter clearly you've become AI obsessed AI pills I don't know what the term is and I love that you're not just the kind of person that just talks about it and tweets pontifications you're clearly using it in every facet of your job and looking for more ways to use AI so I have a lot of questions here because I think this is where more and more founders are going to 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 more most useful

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

Lenny Rachitsky:And you're sitting there in Lindy doing this yourself or do you have people that you've kinda trained to help build these sorts of things for you

Andrew Wilkinson:No I do it myself

Lenny Rachitsky:Okay how many agents if if that's the term you wanna use do you have running for you

Andrew Wilkinson:Oh man I think I probably have not not a crazy amount within let's see each well each workflow probably has four or five agents so for example my inbox has four or five agents and then I have a whole bunch of other you know I've got a calendar agent I've got a meeting agent I've got an email agent I've got scheduler I've got a CRM and basically they're all different workflows with a whole bunch of agents within

Lenny Rachitsky:Okay and you're not even you're not an investor in Lindy right you're just a fan super duper no no fun fact I actually am so this is a great

Andrew Wilkinson:Fan of oh way that's awesome

Lenny Rachitsky:Tiny angel investor so just wanna put that out there I love that this came up organically what are a couple other really interesting use cases workflows you've built that people might be inspired by

Andrew Wilkinson:Let me let me go through the email one a little more so basically emails come in and the first agent says does Andrew even need to see this like let's say you're in a thread and you've already chimed in and everyone's just saying cool that works I don't need to see that so it just archives that never never so that immediately reduces my email up by about 20% then it decides is this something that is time sensitive is this thing that needs to be dealt within the next twenty four hours and if so it labels it in a special twenty four hour label so when I go to 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 email me and you say hey do wanna get lunch so it emails me privately and it says hey Lenny wants to get lunch do you wanna say yes do you wanna say yes but in a few months do you wanna say no how do you wanna say no and it gives me multiple choice I just can say for like four and then it'll email you as me and it'll write out a nice thoughtful email or whatever so stuff like that is like so freaking cool and helpful and I'd say that it's replaced stuff that my full time I used to have a full time assistant just working on email that's all completely automated and there's all sorts of other cool stuff I'm doing there other agents like I'm working on one right now to manage my calendar which is really complex I do a lot of scheduling and a lot of rules I have another really simple one it adds emojis to every single calendar event so when I look at my calendar I've got beautiful little emojis for every single calendar event very silly

Lenny Rachitsky:What are the emojis like do they represent something

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

Lenny Rachitsky:In in Marin in the Bay Area

Andrew Wilkinson: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

Lenny Rachitsky:I I for that

Andrew Wilkinson: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 twenty four seven

Lenny Rachitsky:Okay I wanna follow that thread but first of all what other tools do you have what Lindy is one what else do you find really useful

Andrew Wilkinson:So the other one is Replit so Replit is basically a vibe coding platform you can literally go into it and say you know I wanna make a website for my SaaS software business here's you know a big document with a bunch of details and it'll go and design a pretty impressive website but then you can also build web apps now so you can you can literally be like yeah build a Python web app that does x y z and the design is getting so good because it uses cloud four you can start saying do it in the style of Stripe think this through 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 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

Lenny Rachitsky:That's cool and so your team Replit versus lovable Bold V Zero is that I

Andrew Wilkinson: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 beef to it whereas Lovable and Bolt seem a little more basic you might have to deal with deployment and stuff in a fiddlier way with them.

Lenny Rachitsky:Awesome okay anything else.

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

Lenny Rachitsky:I've I've got one of those.

Andrew Wilkinson:It's 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 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 what did I promise to people today or even better everyone loves this use case I have a fight with my girlfriend and she says you didn't say that and I'm able to say well actually you know you did and and you can query it as an LLM so you can say you're a couple's counselor look at this fight what did each person need how did it start what are the key lines where did it change how could you do this better and so honestly from a relationship standpoint is probably where it's been the most useful what's cool too is that has an API and so eventually I haven't gotten there yet but eventually you'll be able to just have it record your entire day and then automatically go into your to do list or whatever it is and add to dos or send emails or whatever you need it to do.

Lenny Rachitsky:Wow this is so fun or just per your point with the relationship ask it what could I have done better today where did I did I where did the day go downhill.

Andrew Wilkinson: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.

Lenny Rachitsky:Whatever and that was with the Limitless data oh man I love that with the relationship you didn't go or thought you were gonna go where it's like oh but who actually said it what did you actually say I love that it became much more wholesome of just like how could we have communicated better holistically mhmm okay my wife actually is like don't don't wear this around.

Andrew Wilkinson:You just gotta wear it really covertly it honestly honestly I know it sounds kinda cheesy because you think like 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 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 Claude and Chad GPT and Gemini and Gemini I use mostly for things that are really large so for example all my medical records 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 like I went through my entire medicine cabinet and I just took big photos that showed all the different medicines and stuff and now I can say something like hey you know I'm really tired and stressed out today what supplements should I take and what dose or I'll say remember remember all the medications I'm taking whenever I ask you a health question always remind me in the context of I might be taking that medication so a few times it said hey you shouldn't take this other medication because your genetics say you're not compatible with it and you're already taking this other one so stuff like that's been really helpful.

Lenny Rachitsky:For that use case do you come back to a specific conversation where you've given it that context use a project I.

Andrew Wilkinson: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.

Lenny Rachitsky:I see so just tap into the memory of ChatGPT yeah this is awesome this makes me remember that I I've started to use and this connects to other points you've been making I've started to use ChatGPT deep research to prep for these conversations I used to have a researcher who did this for $400 they did research on every guest that I had 40 to $500 and gave me a whole doc here's everything about them here's their background here's questions you might wanna ask deep research is better just as of recently especially with O three pro.

Andrew Wilkinson:We were talking earlier about agents I forgot one of my favorite agents so it looks on my calendar 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 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 and it basically does all the research for me so I 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 what are our commonalities and what are all the fun things we should talk about.

Lenny Rachitsky:Oh my god I just I just wanna plug and play all these agents you've built to use them myself interestingly I tried to create an agent to do this research kickoff for me but I don't think you can automate chattypety deep research okay.

Andrew Wilkinson:Perplexity okay.

Lenny Rachitsky: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 as a contractor i was working with for a few months i no longer need them your assistant you no longer need thoughts on just the impact we're gonna see on jobs as a result of ai

Andrew Wilkinson:there's this great william gibson quote the future is already here it's just not evenly distributed and i think that we are in the palm trio phase do you remember the palm trio no so so when i was let's see in 02/2007 i think was that when the iphone came out 02/2007 i'm really out of '7 something like that in 02/2007 there was this device called the palm trio and it was like a little pda yes with a stylus and you it had a little modem attachment and so what you could do is you could get your email anywhere and that was this shocking thing it had a 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 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 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 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 gonna have in sometime in the next five years and so i think that if ai doesn't progress we will see some serious job displacement like what you already mentioned the translators the researchers the admin some assistant jobs depending on the kind of work they do those jobs will definitely be massively affected but i think pretty quick all knowledge work jobs could be affected if the models scale in the way that they say they're going to i mean if you trust sam altman and dario amadeh i mean dario amadeh said by 2027 our models will be smarter than all phds any 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 gonna how it's gonna 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 gonna change massively

Lenny Rachitsky:okay there's a lot here i actually had mike on the podcast their cpo mike kreger and he pointed out that dario every prediction he's had so far has been right over the past few years and so there's reason to listen to his insights okay andre know you're not gonna have all the answers for people but let me ask you a kind of a two part question for new grads and for people currently in the workforce say like i don't know senior product manager advice on what they should do where should they focus what skills will matter most what jobs do you think will last what advice can you give us

Andrew Wilkinson: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 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 toolset right now but i don't know how relevant that is in the future because i think we're still again in the palm trio phase i think that the ais will be very good at eliciting what the actual problem you're trying to solve is and reinterpreting it in a way that it can optimize the query to get the right answer and solve the problem and so i think the fundamental question is do all jobs just become a single prompt so for example does a ceo just become grow the business while making the customers happy and turning a profit or or something like that and it is able to actually be in 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 you know calendar entries and that kind of stuff so i don't think that's totally imminent but i can certainly see a world where that's coming and so the question is what is one to do when that reality is barreling down at you for people who have resources i think there's a lot of things they can do in terms of investment they can invest in the companies that'll benefit from this companies that have a lot of compute or energy or that sort of thing so that's one thing but that's not really the question the question is what do you do if you're a smart 18 year old or 19 year old or whatever in my opinion i think the best thing to do right now is to get incredibly good with these tools and utilize them to build enough wealth that you can put the money into diversifying into compute and energy and i do think that while everybody thinks that you know all jobs will go away in five years and robots will be everywhere people generally overestimate things in the short term and underestimate them in the long term so i think there's 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 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 weird 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 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 play to plays play pickleball with you or something i don't know but i could 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 toe things will either be totally fine or they will be terrible and we'll all be dead and i can't predict which one of those is there i don't think it's worth thinking about all of us being dead and so i think it's really just lean into what are the tools how do you stay cutting edge how do you build businesses and wealth in this new world but i'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

Lenny Rachitsky:i'm picturing this dystopian world where humans are just going around making jokes

Andrew Wilkinson:well it's like where does where does status come from right in a world of abundance where does status come from you know maybe it is just like having being the best at hiking or something

Lenny Rachitsky:well let me ask you this because this is where it gets even more real is just with your kids what are you encouraging them to learn what are you encouraging them to get good at because that's you know like this is the real problem a lot of people are having right now is what will matter in the future obviously don't know but what are you what are you what are you encouraging them to focus on

Andrew Wilkinson:well i don't know i mean they're so little they're five and eight and so really what i'm focused on is making sure they're socialized and they're polite very basic so are they comfortable talking to adults like i often send my son whenever he wants something at a cafe i always make him go up ask nicely pay himself all that kind of stuff but at this point you know i feel like for the first ten years of life you're just trying to make sure that they're not traumatized or rude and the i think it's gonna 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 but i have no idea and to be honest it's not something i'm worrying about because it's too hard to worry about i don't know it's too multivariate there's too many ways it can go

Lenny Rachitsky:i feel like a core part of your message is just get good with these tools there's you know this classic quote ai won't replace you it'll be somebody very good using ai is gonna replace you at least for a while and so it feels like a big part of this is just like use these things before we were started recording we were having a mic issue and i love you just went straight to chatgpt chatgpt how do i connect this mic to riverside and make it work and i feel like that's just a habit to build is just assume chatgpt like go to chatgpt whenever you have a problem like i've been doing that a lot i was connecting a subwoofer i'm like what wire do i need to buy to connect the subwoofer to the receiver

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

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

Andrew Wilkinson:do you remember 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 i need to move away to europe i need to go discover myself and i'd be really anxious and stressed out and in an existential crisis and then i'd fly to europe to go backpacking or something and i'd still feel anxious and have my existential crisis it's just now i'm in europe and i think the reality is that whatever is in your brain whatever that anxiety loop is doesn't go away just because you have a bigger house or more money in the bank account or you're in bali or wherever it is that's a chemical reaction happening inside you that relates to your past and your dna and all that stuff that creates that soup and for me i've always been a very anxious person i've always worried about tomorrow i rarely enjoy today i'm always worrying about what could go wrong in health or my businesses or with my family or whatever it is and so when i started my business all i thought was i just don't wanna work for someone else if i can just wake up in the morning do my own thing make 60 a year then i'll be happy so i got that and then it was once i make a million dollars a year and i can buy a house well i got that and so on and so on and so on all the way up to at one point being worth over a billion dollars by the way should redo the title of the book from barista to billionaire now it's former billionaire because our stock went down but you know it didn't change anything like i'm still just as anxious as ever i remember a month ago i had this day where i was sitting in the sauna and i was stressing about a bunch of business problems and money things and i had this i stopped myself and i was like wait a minute like ten years ago i had all the same thoughts and i was stressed out about similar kinds of problems and our revenue was $20,000,000 or $15,000,000 now we're at you know almost 300,000,000 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 multibillionaires 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 multibillionaire single digit multibillionaire and he goes oh jeff bezos he's just so fucking rich and i was like wait like what what do you mean you're worth like $5,000,000,000 like what can what can he do that you can't and he goes he can buy a superyacht and it's like what like and you know you can look at that guy and you can say oh that's a wacko and all the other stuff but the reality is that we're all just comparing ourselves to our peers whatever our peers have that we don't we feel hard done by and i remember just thinking like oh my god how do i not how do i avoid becoming this and that that's the scary reality is no matter how lucky you are i mean we're all so fortunate we live in you know for me i live in canada i have every opportunity that i ever could have hoped for and there's people all over the world who have nowhere near what i had growing up and yet i felt hard done by because in my neighborhood i was the poor kid i wasn't poor globally i wasn't even poor based on canada but all my friends had big screen tvs and would go to hawaii and i never got to do any of that stuff my parents were stressed about money so i feel hard done by

Lenny Rachitsky:there's a phrase a friend's financial adviser once shared the joneses are doing really well

Andrew Wilkinson:mhmm

Lenny Rachitsky:and that's hard to get over yeah what so what changes did you make to just be happier you know it's hard to give up money it's hard to give up more money you could make it's hard to give up things that you know that that money buys i guess just so what what did you change

Andrew Wilkinson:Well there's a few things I mean one was reframing money to some degree to have it be something that wasn't just about feathering my own nest and making it better so for example I was talking to a friend who's very wealthy and I was kind of saying like you know I all the feelings I described of you know have all this and yet I don't feel better and he said well you know what are you working for and I said well I guess I'm just working for the numbers to get bigger and you know have more employees and you know that's nice like our businesses do good things in the world and help more people and stuff but ultimately it's just to pile up cash and he said you know I've reframed it so that all my money 90% of my money plus goes into my philanthropic foundation and then it gets given away to great causes so when I think about working really hard or losing a deal or an investment going well the win isn't for me the win is about doing something good so so I did that and that definitely helped I also stopped spending as much money I found that you know the more stuff I had the more houses I had the more people that directly work for me to manage all that stuff the less happy I was you know I was kinda owned by my stuff and then I also do a real I work really hard not to have people 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 schmo you know I just try not to be you know a weird out of touch rich person but the biggest thing which is kind of a weird answer is actually medicating myself so basically like all my life I've been really anxious and in 2020 I remember I was watching a movie with my ex wife and I was looping on you know I need to respond to this email if I don't respond to that email this person's gonna be mad and then I realized that I was watching a movie for the last 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 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 gonna take a tiny little piece and it took me six months after that to try any but I started taking these pieces every day and I just noticed that within about three or four days it was like someone had turned down the volume on the nasty voice inside of me doing all that and for the first time in my life I felt relief I'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 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

Lenny Rachitsky:Wow that is 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 medicate yourself you're gonna you're I don't know there's all these downsides all this risk the pharma industry is trying to make money I love this other perspective of it it's actually really effective and actually makes a big difference in your life and it may be the only solution

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

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

Lenny Rachitsky:Amazing Andrew we've covered so much ground I love the spectrum of topics we've gone after is there anything else that you wanted to share anything you wanted to double down on any last nugget you wanna leave listeners with before we get to a very exciting lightning round

Andrew Wilkinson:So one one thing that was kinda 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 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 test with a neurologist and she asked me a bunch of questions you know it's remember these 10 digits and say them backwards and all this stuff and finally when I get my test results back she said look your crystallized intelligence your ability to remember stuff long range is totally fine you're you're above average your short term memory your working memory is tenth percentile very very bad and you probably should get checked for ADHD and I was like nope there's no way I don't have ADHD I'm organized 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 you know you can go online and just quickly get tested or whatever but I went through this really really you know like kind of five day process to get tested and it turned out that I do have it and it's really interesting because if you take the normal population about five percent of people have ADHD but about thirty percent of entrepreneurs have ADHD and many entrepreneurs I talk to they love new things they love jumping around between a million different topics they're an inch deep and a mile wide like I described and they describe themselves as unemployable and I frankly I remember I was so skeptical of ADHD that when my girlfriend told me a friend of hers got diagnosed with it I sarcastically said oh good she better take some meth right talking about stimulant drugs some I I previously I was very very skeptical of ADHD but it is a real brain disorder if you actually dig into it it's very a very real thing very objective that people have poor executive function and for me it's given me a lot more empathy for myself and my behaviors because at work if you have ADHD you can delegate to other people and build systems to get around your disability but at home that's where it really plays out and so for me it's like my girlfriend asked me to take the garbage out and I say of course and then I forget three times in a row and she views that as you are being very hurtful and you're not caring for me and it causes you know all sorts of different problems at home and so for me not only did it make my work life better because I was more focused but it actually really helped me in my personal life and it made me feel not broken I always felt a bit broken I couldn't put my finger on why but I just went I'm not good at doing all the things everyone else seems to be able to do no problem and so I think especially because you have an entrepreneur audience I think a lot of entrepreneurs should consider getting checked for ADHD just go 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

Lenny Rachitsky:Man this garbage story is very descriptive of my life and so I'm gonna do this oh boy there's kind of this implication that it's good to know this right like people would be like it feels scary to feel like oh shit I might get diagnosed with ADHD your advice I imagine is like you'd actually it's better to know because you could do stuff about it

Andrew Wilkinson:Totally I think it's like any medical thing right it's like there's an Alzheimer's gene right and if you know you have it there's a lot you can do to slow the disease or prevent maybe getting it or whatever 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

Lenny Rachitsky:Beautiful okay well Andrew with that we've reached our very exciting lightning round I've got five questions for you are you ready

Andrew Wilkinson:Let's go. If I could only recommend two I would recommend The Laws of Human Nature by Robert Greene it's basically like a compendium of every single type of personality disorder or psychological effect how do people warp their minds to make bad decisions what is a narcissist what is a psychopath all that kind of stuff and Robert Greene does such a great job of telling all that in a really engaging way by using storytelling so every single chapter has a story about someone with that personality disorder 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 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

Lenny Rachitsky:Next question do you have a favorite recent movie or TV show that you have really enjoyed

Andrew Wilkinson: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

Lenny Rachitsky:Do you have a favorite product you recently discovered that you really love you already mentioned limitless is there anything else

Andrew Wilkinson:I'm one of those people who really believes in the idea of a robot vacuum I've probably spent like $10,000 on different robot vacuums over the years probably five or six of them and I finally got one that actually works it's called the matic vacuum m a t i c and basically I think it's like former Google engineers basically built like a mini Waymo car so it has like machine vision and it will avoid absolutely everything and never get tangled it can mop your floors and vacuum I've been super impressed with it so far

Lenny Rachitsky: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 it has this little personality and it just does a really good job and I'm not an investor and that's awesome I'm a huge fan okay next question do you have a favorite life motto that you often come back to find useful in work or in life

Andrew Wilkinson:Yeah my favorite is a quote by jersey gregorick 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

Lenny Rachitsky:Final question okay so let me know if this is true I I found that when you were a teenager when you're running mac teens you interviewed Steve Jobs at a conference is that true

Andrew Wilkinson: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 kinda laughed at me like they're like yeah there's no way you're not gonna 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 02/2004 no 02/2003 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 realized it's Steve Jobs and he walks directly up to me because I'm first in line and he shakes my my hand and he says hi I'm Steve and I'm like a quivering mess you know I'm 17 years old I he's my hero he is my Jesus and so I was just so high on adrenaline that I just started asking him questions as soon as we walked in I basically just stayed at his side and I just picked his brain about all sorts of different stuff so it's not like I got to ask him questions about life I was asking him about you know the new 17 inch iMac or whatever but it was a pretty cool experience to get to meet him

Lenny Rachitsky:That is awesome there's such a funny thread recently with guests everyone's there's a Steve Jobs connection for the past couple months of guests 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

Andrew Wilkinson: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

Lenny Rachitsky:The door door in the face technique I think people call it yeah Andrew this was incredible two final questions where can folks find you if they wanna reach out I know you're buying companies investing in companies just talk about what you're looking for there in case people are like this is me and then finally how can listeners be useful to you

Andrew Wilkinson:Yeah my my business is Tiny Tiny.com and we buy businesses we 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 and would show up in our office in suits and you know use a bunch of words we didn't understand and we ended up going man why can't we just sell to somebody who's like us and so we basically started Tiny to become the buyer we wish we could have sold to and we're looking for businesses that have some of the qualities I mentioned before so you know really high quality businesses that do something positive in the world and have happy customers happy employees and some kind of competitive advantage that will make them continue into the future so we own like Aeropress Letterbox Dribbble which is like a design social network whole bunch of businesses like that so if somebody is thinking about selling their business definitely get in touch

Lenny Rachitsky:Amazing okay and then how can listeners be useful to you if it's not just that

Andrew Wilkinson:I just would say if there's anyone really interesting coming to Victoria Canada which is where I live send me an email and I would love to have coffee with you I just I I the reason I love going on podcast 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

Lenny Rachitsky:Amazing Andrew thank you so much for being here

Andrew Wilkinson:Yeah thanks dude that was fun

Lenny Rachitsky:Bye 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 lennyspodcast.com see you in the next episode