Linktree Founder - spinning side project into one of top 3 fastest growing companies in the world | Alex Zaccaria

0:06We were the user. we understood the problem so deeply. We created it to solve a problem for ourselves. We always thought about it from a product perspective. How can we productise this? How can we build this product? Hey client, we'll actually give this to you for free if you let us build this product and we'll go sell it to everyone else.

0:28That's Alex Zakaria, the co-founder and CEO of Linktree. Linktree is one of those ideas that seems so simple it's difficult to imagine nobody thought of it before. It's a kick-yourself product, especially now they're worth over a billion dollars. Linktree solves a unique problem in the social media age. Most social sites like Instagram only allow you to have one link in your bio. For successful people in all kinds of industries, like music, picking that one link is a nightmare. Do you want to send your followers to your merchandise, to your website, to your tickets, or wherever? Linktree solves the problem by having one link to rule them all.

1:04You put your Linktree in your bio, which, when clicked on, displays various links to various things that you might want to promote. It's a product so ubiquitous that we even use it here at Secret Leaders. Alex, his brother Anthony, and their business partner Nick Humphreys created Linktree because they saw how much time they were wasting having to update individual bio links for their clients at their digital agency, Bolster. After running the operation as a bootstrap side hustle for several years, things snowballed when singer-songwriter Alicia Keys joined the platform. It's a tale of opportunity and intuition, which Alex and his brother were able to grab because they grew up surrounded by business role models.

1:43I was the fourth child, the youngest child out of four. So two brothers and a sister. Grew up in the suburbs of Melbourne. My father came to Australia from Italy when he was around 19. And my mum was born here, but both her parents came to Australia from Italy when they were around 16 or 17. And so, yeah, I grew up with a very, very strong Italian heritage. My parents spoke Italian at home, almost exclusively. Yes, my parents ran a musical instrument store, and they also imported musical instruments. So to my grandfather, he found a mandolin in the trading post, figured he could fix it up because it was a cabinetmaker by trade, resold it, started doing that a whole bunch.

2:25I eventually opened a music store and then ended up with a record label and a radio station and imported white goods in a retail store and an accordion and mandolin school and then his own guitar brand and his own amplifier brand and so I think I was kind of you know I looked up to him a lot growing up and my parents were deep into music as well and had their imported musical instruments and at a music store so my childhood was uh you know going to primary school and then I would get picked up or whatever it was quarter past three in the afternoon I would go straight to the retail store uh until maybe five six seven o 'clock when mum was finished working dad had finished you know he became a luthier he fixed violins um mum would do the payroll and cash up at the end and I'd be kind of like coming home at seven o 'clock with them you know at the time I'm sure I I can't remember if I loved it or didn't but I remember really distinctly like just being surrounded by these instruments and even now when I walk into a musical instrument store I just get this waft and like incredible sense of nostalgia.

3:24Like every music store just feels like home. Do you know, do you think that gave you an entrepreneurial spark in itself? I'm sure it must have. Pretty much every dinner table conversation was about business. My eldest brother ended up leaving school in year 10 and running the family business. It was pretty much always some kind of debate or argument or yelling or talking about something that's going on at work. And that was just completely normal. Like the tension of that was entirely normal. And it's probably what normalized me being able to work with my brother and founding Linktree with. I saw what it took to support a family through running your own business.

3:54I know we would stay at the retail at the store, we'll go home, mum will put me to bed and then they stay up till midnight, one o 'clock, still working. Just that kind of the hustle needed and the work ethic around it is, yeah, I guess that work ethic and what it takes. And I've always, I can't remember ever actually ever wanting to work for someone else. I think this is like a dumb thing in my mind of just asking. I've always just wanted to do my own thing. Many things we kind of need to undo, which I've learned over the years, like this kind of small business mentality where you can't really afford to outsource anything.

4:29You have to do everything yourself, figure everything out yourself, which is incredible for the zero to one in a business. Yeah, the bootstrapper mentality. Yeah, always figuring out how to do everything ourselves. But then when you have to start learning how to delegate and learning how to lead properly and how to trust other people. it's less of the best training ground it's interesting because i'm hearing you know you had a sort of role model to an extent but you know at the very least a vision an opportunity to see what it's like for family members to be working together right because that's obviously what you ended up doing with your brother other brother you often hear people like don't work with your family don't work with your friends but i never saw anything that was that bad because it was actually the opposite right where yeah absolutely there were tips daily every hour like absolutely yelling and screaming matches but 10 minutes later your best mate's having dinner or lunch together um and I think that actually becomes the benefit uh if if you're fortunate enough to be in that position where you can just have that really psychologically safe relationship that you know has come in handy many times over the years working with my brother you know we genuinely we will really disagree we have kind of like the opposite perspectives on a lot of things but right at the end of the day let's disagree and commit or spend a bunch of time convincing each other and then we move on pretty quickly so I think we've been actually it's been a big plus for us I guess I'm jumping forward a bit here but I'm going to ask a question because I am so curious how do your two other siblings feel about the fact that you two work together you know I guess it could have been an interesting dynamic if you were just running like some lovely music shop or whatever but you're running a fucking billion dollar unicorn company you know I've thought about it sometimes like how they might feel about it but they've never shown anything but absolute pride and admiration and it's kind of the family the family vibe I'm super proud of us and just uh and love it I think you know there was a period where I was working in the family business with our oldest brother uh and I moved on from that I felt like there was so much more I should be doing always been yeah super supportive how do you think you'd feel because I guess I'm reflecting on like what your answer and thinking god your siblings sound a lot nicer than I would be I I think I would probably be jealous.

6:38You know, if it were me, yeah, I'm sure there'd be some level of jealousy. I'd be like, mate, you're paying for mom's retirement. That's on you now, I think. But we definitely show the love back in every way we can. And I think it's a, you know, even for them, they obviously saw the struggle of our parents. They went through coming to a show with nothing, building their own business. We grew up middle class and said we have a really wonderful childhood. It wasn't like flush with cash. but we were definitely not in a bad position but we definitely saw the trials and tribulations of of running a business in through its ups and downs you know obviously our parents incredibly proud and our brother and sister are proud it's probably maybe there's a little bit of a expectation on the on the level of christmas present now i don't know good okay um so let's move on to your early career then you grew up with this sort of music influence and music shop around you instruments everywhere obsessed with music what was your early career like like did it carry on following the theme of music it did for a little while yeah so through high school I just knew I wanted to do my own thing parents really wanted me to go to university so I was going to go to study entrepreneurship which was a relatively new course in Australia at the time I ran the formal after parties for the year 11 and 12 when I was in year nine I did all kinds of like side businesses I I then went to university.

7:58I stayed maybe a few weeks, like maybe formally a term, a semester. And I got out of there. I absolutely hated it. Figured I could learn a whole bunch more just doing things myself and learning and failing. And again, I recognize that's a privileged position to be in because I had a roof over my head and somewhere to leave with my parents. Yeah. So when I did that, I went and worked with my parents. Started kind of just working on new ventures for them, like trying to modernize, you know, a relatively legacy wholesale business. We launched like a vending machine business where we sold guitar strings and drumsticks and things to a vending machine.

8:34We launched a bunch of D2C consumer websites with the products they were importing. So kind of modernized that. I then, I was still running parties and club nights. I got to a point where I was running an events company. We had maybe four or five nights happening per week. started touring international acts and launched a record label uh amongst it and meanwhile my brother was managing bands he had moved to sydney we realized hey i'm managing djs i'm managing bands you're managing bands we should do this together and so we decided to combine forces and that was when bolster music was born which was a a management agency uh that was fun for a while we we had a little bit of success we had you know some bands reached the top of the charts or the you know top 10 in the charts in australia we had one song reached number one in 41 countries uh and so that was fun for a little while but through that and through you know knowing the music industry growing up uh and then knowing the music industry managing bands uh in australia we really realized that the music industry was not taking advantage of digital marketing or technology digital marketing technology that other industries were taking advantage of, like e-commerce and what brands were taking advantage of.

9:47So, you know, I'm talking about things like remarketing and conversion tracking and those kinds of things. Anthony had started doing some just like freelance media buying for a festival and I was looking at it. I was like, we can do so much more with this. Stop buying display ads and this boring stuff. Like we can do some interesting stuff here. And so when I convinced a festival that we knew what we were doing with this, they gave us a$300 ,000 budget. and it was the first time I'd signed up to AdWords. And so I went and figured out a way to spend 300 grand on AdWords and Facebook ads, basically took it to four or five all-nighters and just figured it out and turned out, you know, it was significantly more successful than what they were doing, just simply because we actually started using more modern technology.

10:29That was the launch of kind of Bolster Digital, which was essentially digital strategy for music and entertainment. We grew it out to 20 people in its first 12 months, took over almost every festival, like just started doing the digital strategy for almost every festival in the country and then moved into record labels and artists and into other verticals of events, comedy, film, etc. So about a year into that is when we realised, hey, these artists have got no way of connecting all the dots. They can only link out of socials to only one of their revenue streams. They really need to be able to connect all their revenue streams into one place and it's actually quite a problem for them and it's pretty annoying for us.

11:06And so we should go solve that. so what were the flops before we get into like how successful that agency was like what did you learn about failure in any of these endeavors oh so many so the the vendor machine was quite interesting uh that ultimately flopped just through i just had in my mind that musicians were never going to pay for anything without a credit card and i could not figure out how to get credit cards installed in vendor machines in australia and so we killed that uh and actually launched in that period as well a thing we called happy hobo which was basically a mattress we designed to turn the backseat of your car into a bed uh and we figured out a way to design them did all the branding ordered 500 of them it was very much because we see music festival kids uh go to festivals and sleep in the back of a car not pay for camping tickets and such and so it was very much marketed towards music festivals but no one no one bought it for music festivals we did sell them out over the next six months or so but it was actually to mostly the pet owners uh that wanted a backseat bed for their dog uh and so that was like an interesting lesson in knowing your customer before you start things uh still kind of worked out in the end we didn't continue that one of the biggest failures was a festival website so we got into building websites for a lot of the major festivals in the country and for a festival the launch of a website at the moment of launching your lineup is like the most significant moment of your campaign we were spending weeks building this website multiple nighters the night before national radio station in australia triple j announces a lineup at 8am we're supposed to push live on the website and it just completely crashes and just nothing loads for a very long time i threw up i was like it was an absolute disaster of a day and I think that was a pretty big learning for us to you know stop being such cowboys and figure out how to do this properly.

13:02But this is your client as well right so you know also particularly difficult and embarrassing. How would you handle something terrible like that happening? Yeah that was terrifying that day you know especially after I think we're in the office for 70 hours straight or such and so we're not in a in a great place mentally either but that was a big learning and just being really upfront and admitting your mistakes and owning up and acknowledging and writing it you know I ended up just calling him and saying we stuffed up like this you know there was no trying to figure out giving excuses I probably would have wanted to give him every reason understand why this happened it was like look we stuffed up we're gonna make it right give us 10 you know get right now I'm trying to get your website up just let me call you in two hours but ultimately it was okay they were actually incredibly understanding given the circumstances so before we move on to lintry i just want to know like how big did this business get and kind of how do you maneuver out of it bolster got to i think around 70 people uh which for a niche agency in australia is sizable uh we continue to add services as very much digital strategy for music entertainment culture but we begin to add data, insight services, started connecting brands to the music.

14:24So it became very much, we became the experts in how to market to a music-based audience. And so we started working with brands on how to activate music audiences. And so we actually ended up launching YouTube music into Australia and working with a bunch of major brands. And then we started doing digital rights and rights for festivals, so activations of festivals as well. So started really connecting the dots across kind of these, like cultural audiences which was heaps of fun festivals have significantly more reach and more clout than traditional publishers have and so we ended up working with a music festival in Australia real tastemaking music festival called Lameway Festival and we turned them into a media publisher so we launched her always on media property and started yeah doing real journalism through that amongst music and connecting that with brands and that was a huge huge learning lots of fun as well ultimately when COVID hit is when that started to go the other way because it's all music and whilst we had thought about a bunch of contingency plans and thought about you know what happens in what happens in an economic downturn you know we started to think about planning for this agency we never really planned for a pandemic because I'm sure many people didn't and when the prime minister announced there are no longer you know festivals and events are cancelled 95 % of our clients walked out the door in one day.

15:44That was pretty tough. But it was at the exact same time, actually, the ring tree got a massive tower wing and went the complete opposite way. So we had one business that was on life support and one business that had turned into a rocket ship in a day. And obviously, what an incredible way to hedge your bets by total luck and coincidence. I want to know one mistake that I see founders make often, and I almost made this mistake myself, is you're running a business. It's a really good business, a big business. It's an exciting business, so Bolster is a perfect example of all of this, you have a new idea.

16:14You don't know how that idea is going to go. You certainly don't know the communication of how to tell other people, I have this idea. I don't know what to do. So you basically do it as sort of entrepreneurship inside that company. And you start that business inside that company. Right or wrong, but this is a very common mistake I see entrepreneurs make. How did you literally set up Linktree at the same time as Bolster? What were the kind of timelines there? And how did you find managing the communication around who knows who doesn't what's right what's wrong yeah it's always fascinating watching products come out of agencies and how agency founders think about this because i get the question all the time of how that went about it's fast it seems to always be that agency owners after a few years it's just like oh my god how do i turn into a product please get me out of service also because agencies have really like their job is they have creative people right so like you are going to have really great ideas yeah it's just uh but whether or not you can like focus on executing them is the hard thing.

17:08Totally. And because of creative people, I also think because you're just solving problems all the time, a client gives you a problem, you're solving it for them. And that's ultimately, ideally the creative thinking about ideas. You know, you're so close to the customer all the time because you're dealing with them as a client. And that's ultimately where the tree came from. Like we understood, we were the user, we understood the problem so deeply. We created it to solve a problem for ourselves. And pretty We always did that whenever a client asked for something or needed a problem solved and we came up with this creative campaign idea.

17:40We always thought about it from a product perspective. How can we productize this? How can we build this as a product? Hey, client, we'll actually give this to you for free if you let us build it as a product and we'll go sell it to everyone else. And Linktree was kind of just one of those things that we thought about and we were sick of changing the link and buy all the time. We recognized we needed to consolidate all these links with linkers. it was also the musicians that have many the music industry is incredibly fragmented you know you've got your streaming on a whole bunch of different platforms you've got your merch on another platform you've got your ticketing on a whole bunch of different platforms you've got your video content another platform again and so and generally each of these platforms are looked after by a different stakeholder your label your agent or your manager and they'd all be arguing when we're trying to run a campaign over what was more important uh what we should lead with and so So that was another kind of input into just deeply understanding this problem and needing to solve it.

18:32We kept having these ideas. We were never very good at writing them down and sending them off to an engineer or developer somewhere else. And we just really wanted to have a developer in-house with us where we could just tell them the idea and they could build it. And so we did the same thing we did initially with music, with the digital marketing. We went and convinced the client that we knew how to build websites. when we want a client and we realized we don't have a we don't have a developer to do it and so I heard about this guy who played guitar he was a single songwriter that he also was a web developer and I went to his show that following Friday night and I accosted him inside a stage and pitched him to come and build this website for us and managed to keep him around uh to then you know we had maybe two months worth of his salary his wages to continue paying him that was around the time we had this idea for Linktree and it was really fortunate and we had nothing for him to do and I could just go straight to him and be like hey this is the idea do it and literally we built a prototype in six hours and we continued to to grow it really it was it became a side hustle to the agency and we also worked on it in the agency and so there were people within the agency that got to work on it but most of the time that that agency was scaling so much that unfortunately and I'm sure many agency owners or those that build products in agencies get this the client work always comes first there's always some kind of deadline and so your own product just keeps getting pushed to the bottom of the pile and so we would always be working on a way to know we'd come home at maybe 11 o 'clock midnight from the agency we'd stay up until maybe 3 or 4 a.m answering support tickets keeping the thing alive and eventually we got to the point where hey we decided we needed to split this and actually have a couple of dedicated a couple of the engineers go dedicated onto the product because it was just never getting the intention and it was growing enough such that it needed full-time support from an infrastructure perspective at least let alone building features It was built into two companies.

20:19It split out relatively early in the piece to at least have its own company for it. But it was very much working with the resources inside the agency, as well as a whole bunch of hustle at home. As you know, there were people that absolutely loved doing the agency work. They were like, stop putting me on Linktree. And there were people that loved doing the Linktree work. And they were like, stop, you know, stop giving me agency client work to do. You know, it kind of evolved relatively naturally from there. what about like the drive to do it with your brother again was there a moment where you both decide to go and do it together like at the same time yeah again i think it was quite natural we were running the agency together actually also without with one of our mates without one of our mates nikki who so he was a designer he was actually living in london doing the australian in london thing gallivanting around making no money trying to be a designer in agencies and making coffee on the side to survive we realized we needed a creative i called him and said hey you're making no money there you should come make no money with us yes he was such an awesome designer and awesome guy i just really wanted him to be the one that helps us build the digital agency into more of a creative agency we were doing it all three of us all together link true was born out of that agency utilizing the resources being paid for that by that agency so it was just a natural thing that actually all three of us own it and all three of us are founders anthony my brother had been like facing this challenge constantly it's probably like the thousandth link and buy who he changed that day for one of our clients and it was like what like there's got to be a better way and I was like got this idea Nick did all the design to start with so it was very much all three of us anyway and it was kind of just evolved quite naturally we've kind of just always done everything together from then even now recently launching a fund to do it together everything that we do yeah I don't think we've ever actually sat and been like hey everything we do we do together it's just like a very natural fit we love working together we know each other's strengths and weaknesses so well that we can play off each other really well and so it seems to work.

22:08And I know I'm incredibly fortunate to have, you know, I had many partnerships prior to that that didn't quite work. So when you find a way it works, you want to stick with it. 100%. If I ask them what your biggest weaknesses were, what are they going to highlight for us? Oh, so many. I'm extremely pie in the sky, always thinking about the future. And so tend to miss deadlines, get it right in front of me or, you know, not super diligent about meeting deadlines. I'm sure my executive team will say the same thing. I've always been really thinking about, you know, really optimistic. I'm like way too optimistic and very trusting and thinking about the vision and we can do all these things.

22:48Anthony's a very risk-averse one, much more pessimistic. I generally will battle things out pretty quickly. I reckon we'd probably still be in our mum's garage if it wasn't for me, but we'd also be entirely bankrupt and would have wasted all our money and done something very silly if it wasn't for Anthony. and it played quite well and nick jennery's has got this immense trust for us where we do all the kind of the business and money side of things and he's the creative we've just had this great trust between each other the worst decision we ever made was when we all just agreed really quickly on something and so now when we like pitch an idea to each other and it's just like yeah great idea we're like whoa whoa whoa that's a bad idea like let's examine this more um okay so let's let's talk about linktree then i mean it's kind of a business that i i would imagine but like a business that felt like it came out of nowhere to other people.

23:34A labor of love for you. Take us through the dates. Yeah, so we were, you know, we had this issue. We recognized that there was this challenge that our artists, our creators were having. It was a really quick, simple solution that, hey, I needed a link that we could put in the bio that we can just change and manage from a completely separate area and we don't have to go and edit and change it all the time. And it should be able to schedule and reorder the links and should be able to customize it to make it look like and feel like your brand and you should be able to track analytics and do remarketing and do all the kind of my tech things we were doing.

24:04We quickly put that together as a prototype, launched it and gave it to a few of our clients, you know, 10 or 20 signups almost immediately and realized that actually people are starting to click on this thing and use this thing, so we should probably build it properly. Got to maybe a few thousand users after a few months. I think it was maybe December that year, someone had put it on Product Hunt and I was very excited, but we just kind of sprung into action, stayed up pretty much all night, replying to comments it did really well servers got them got into a little bit of trouble but it was like this really exciting kind of moment where we realized that actually a lot of people were just like praising and seeing how simple it was and and realizing what we'd built about a week later we realized that signups just started going crazy and at the time we had it we had an integration into slack where there'd be like a ding every time someone signed up and it just started going crazy we realized that alicia keys had signed up and we figured it must be fake uh but it turned out it really reached out to the agency basically did whatever it took with them to build custom features for them so they would sign up the rest of their roster and that ended up being the killers and pill jam and chili peppers and elton john that was obviously a big pinch me moment just out of interest did you ever find out if it was her specifically that chose it or it was her agency did you ever find out the person who signed up alicia who was working at this agency who signed up founded and signed up for alicia keys actually now works with us at link tree um we eventually took him over, brought him over the fence.

25:27He runs our partnerships now. And so, but it continued to grow outside of artists. And that was, you know, this really fascinating moment where we realized, hey, you know, there's this, the Guardian signed up and we did not build it for publishers. Why did you sign up and learn from them, call them, understand their use case? Comedians signed up, actors, chefs. And so we kind of just really rapidly continued to talk to our users and understand why they're using it, building out functionality and trying to solve their problems as quickly as we could so this is maybe jan or feb about a year in so at this stage we're maybe at about 15 000 20 000 users total we were maybe around a thousand sign ups a day from but we're about 50 sign ups a day before product time it went to about a thousand sign ups a day after product time and went to about three thousand sign ups a day after alicia keys uh so it was about time we turned off that integration it got pretty annoying uh we just kept hearing these bells all the time and so it was obviously incredibly exciting time we realized we're getting all these requests for features that we that we could charge for and that actually be single-sided to cost us a lot of money to run um and we needed to start charging for it and so we built out a bunch of functionality like analytics and custom um so we realized users want to customize themselves so we launched that analytics scheduling i believe i put it into a paid version came up with six dollars because it sounded like we'd thought about it uh and launched it there was a sign up almost immediately that night i remember doing it all night just watching the chart watching these transactions come in watching the dashboard following them talking to them on chat learning where it was going wrong all i wanted it to get to was you know seven eight thousand dollars a month so i could hire another engineer and we just thought about it in salaries it was like okay we now clocked another x per month we can hire a designer x per month we can engineer was just like completely feeding it back in so maybe fast forwarding towards 2019 getting to the point where the revenue was actually exceeding the agency uh we figured we should actually really separate this out from the agency and focus on it and how many people were working for you then sorry it's about 70 or maybe 60 to 70 at bolsters maybe four or five in which says everything you need to know listeners about the difference between assassin agencies exactly exactly and why you start to go yeah how do we how do we start getting into product started we start to get quite a lot of interest from vcs at this stage i have no idea what vc means or what that world is i didn't know vc existed to me a business is aimed to be profitable you know like you bootstrap it and so it took a little bit to learn about this world but it came to early 2020 after the bushfires in australia and we realized that our platform was doing a little bit of good we we launched this thing to where you could add a way to accept donations onto your profiles and we raised a few million dollars through profiles from external like overseas cash into australia to give to the wildlife and the and the fireys and realized we really should spend a lot more time scaling this uh and it was tricky because you know building an agency with clients who care deeply about they want a relationship with you and the amount of time I was spending with clients was taking my time away from Linktree.

28:36And so we committed to thinking about how we can transition a little bit more, spend a bit more time in Linktree. We were also starting to find it challenging to compete with other VC-funded startups in Australia for talent that we needed, specific talent that we needed for Linktree compared to what Balsa needed. And so we started to explore this VC thing and we went to LA and SF in March 2020, which was a really great time to fly overseas as you may recall. I was there in March 2020 in LA raising money for my startup. I literally landed from London on Friday and I had to fly home Sunday night and do any of my meetings and all on Zoom anyway.

29:16It was so annoying. It's exactly the same story. Yeah, essentially we ended up on the last flight back into the country whilst we were in the air. Australia decided that if you came back into the country you had to quarantine. and so my now fiance left the house uh so then mickey and i could stay in it for 14 days and we just stayed in the u.s time zone and just still did all that for literally for two weeks stayed in the u.s time zone locked in a house and through that period we had gone from you know the four or five thousand signups a day to 35 or 40 000 signups a day um it started really accelerating and so and you know vc still were exploring do we even want to do this but vc contacting us saying hey, you're the fourth fastest consistently growing company in the world right now.

29:58You should really consider funding. And we played around with it and ultimately decided, hey, to build a consumer-led business in Australia, there isn't many of them here. We really want to call Australia home and continue building it here, but we need some help around the table and some assistance and advisory on what we should do here. So I wanted to raise mostly from a people perspective to get the right people around a board and have a board and add a little bit of fuel to the fire to go scale and hire the right people. And how much did you raise? That was about$10.7 million. That was one of the most fascinating calls I had to appear.

30:31Generally, VCs were quite like, no one could quite work out Ringtree at the time. It's a lot more ubiquitous now and people get the reason why it exists and its place in the ecosystem. But a lot of people were very much like, try and understand why at the time. And Insight was very much, they could explain it back to me better than I could explain it myself. and it was a really interesting conversation about where this thing could go. So we're super excited to bring them on board and then less than six or so weeks later, we actually did our next round with another 45 million with Index and Co2 and Insight as well.

31:04That was then, you know, the period of figuring out how do we go from bootstrapped to having this capital? How do we make sure that we keep this bootstrapped scrappy mentality? But where should you spend the money? Where should you not? how do we grow sustainably? And then in 2022, you then raise over$100 million at over a billion dollar valuation, right? How do you deal emotionally with the really strange reality that you actually have a business failing, a people business as well, people heavy business? I think that's the most interesting and important part of it. But at the same time, you're also one of the hottest startups in the world.

31:43At the time, we didn't even have a chance to think about it. Like it was just absolute chaos and just trying to do everything we could for both sides of the business, trying to like come up the learning curve and figuring this VC thing out, figuring shareholder agreements and all those things, which we, you know, as three best friends and partners, we had never even done that between us. Like it was a lot of that kind of learning. But also, yeah, like we were, you know, building an agency over a few years with these people. It was like such an awesome culture and such a really nice, close-knit team.

32:14And so that was absolutely devastating. And I was very fortunate that Anthony could deal with that while we were dealing with the other side of it. And we were very fortunate as well in Australia. The government helped a fair bit to keep people at least be able to continue paying people to a certain extent and keeping them around. And so just even still figuring that out was hard. But yeah, it could have been a lot worse. And what did happen to Bolster? Is it still running on fumes? Is it still going or did you end up shutting it down? kept it alive. It pivoted to do a bunch more brand work during that period outside of just music.

32:51And a guy who we had, we had acquired one of his, his business into the, into the business a little bit earlier. Awesome operator. Again, fortunately, and we sorted our shares down to him and he took over and still alive. It's actually thriving, rescaling very much in the same space, same vibe about it. And so again, And I don't keep saying I'm unfortunate, but like that's, you know, the fact that that lives and breathes in the same kind of energy that we created around it is awesome. Well, the fact you managed to find the right person, that's the hardest part. Yeah, exactly. And it's very similar to us, similar vibes, similar approach.

33:30And so that's like really heartwarming. We love knowing that that still exists. We can go, you know, go visit the office every now and then and see the energy around it because definitely miss it sometimes. What's been your biggest challenge in terms of personal growth? So going from a bootstrapper all these years, family business guy, all that stuff to running a unicorn, scaling hundreds of people. It's an enormous shift of mindset. What have you personally struggled with? A few that I can name pretty easily. The first one being like the product builder, like the guy who, you know, at my mind thinks in solutions and features.

34:07I generally thought about a feature because of the problem I was having. And it was very like an agency was very directive. It was, yeah, build this. And as you build a product team who want to be the one solving those problems, not being told what to do, it's like the first kind of thing for me to learn and to speak to them in problems and not to speak to them in solutions and learn how to really run a product team. You know, something I'm definitely learning and the biggest learning curve, actually, I can talk about what I'm learning right now. like my biggest learning curve right now is how to be a CEO instead of just a founder and that's a massive shift like founder being very much in the weeds doing kind of everything being super close to it all uh having a bunch of experience on the table but not all of the experience and so my executive leadership team is infinitely more experienced than I am which is awesome but it's also and I deliberately hire people that I'm intimidated by and so it's this this kind of this curve of like how to actually manage them as an experienced group of people with very specific and particular backgrounds experiences opinions uh and lead through them rather than doing things myself it's probably actually the hardest learning curve i've been on how how have you approached that challenge then yes i've had a coach for 18 months or so and and she's been incredible very therapeutic but also just kind of holding the mirror back and helping unpick my mind i have you know advisors as well I think it's trusting your instinct with trusting your gut like when you're running things yourself and you're doing stuff yourself you just make your own decisions and all of a sudden you're influencing people to make those decisions more than just doing it yourself you know I brought this incredible board together of amazing investors and operators who I brought together because I trust their opinion and because I want their experience and so I'd go and ask them a bunch of questions and get their perspective generally they'd all have opposite perspectives and I'd go and talk to my leadership team and they'd all have different perspectives and then I get into this kind of decision paralysis where previously I would just make a decision very quickly.

36:00And that's one thing I've pushed out the other side on now for sure and kind of like actually just go back to trusting my gut, take a few opinions as inputs, go back to making decisions with imperfect information and stop trying to please everyone. And so that was a journey went on in the last sort of six months, I would say. In terms of like how I'm learning how to be a more effective CEO now, it's definitely a coach. I'm very transparent with my team as well. they know this ultimately they didn't necessarily join Linktree because I'm an amazing CEO they joined it for my or our vision and where we're taking it and you know they know I'm super collaborative and consultative with them and they're yeah they're super supportive of that sometimes patient sometimes not patient which is also very good because it pushes me yeah learning through doing but you know trying things getting my head bitten off or trying things and then agreeing and and seeing how it works what's been your what's been your biggest challenge then growing link tree firstly is there something you regret and then like just more broadly what have been your greatest challenges regret you know generally my answer to regret is you know the classic no regrets you learn from things there is one like very big very big like learning i'd call it a big failure which is that we definitely didn't do an amazing job of maintaining that bootstrapped mentality and sustainable approach to growth some numbers we you know we're now 35 million link trees about 1.6 billion visits a month on link trees about 40 ,000 signups a day so still growing a lot but we grew our team from that five or six people at the start of 2020 to 300 or so people over 18 months from our living room and so that was absolutely wild we needed there was a whole bunch of reasons why we needed to do that and it felt like absolutely the right decision to do at the time with the information we had but that ultimately ended up with us they need to do layoffs which was incredibly regrettable and and painful for for everyone involved yeah doing the over scaling thing way too quickly was definitely a big learning a big failure made even more painful for the fact that we were bootstrapped and we knew better but we kind of definitely lent into that very hard and that's still things where i'm doing right now like incredible team but definitely culturally i'm picking the the nature of do you build versus buy or do you like the frameworks around capital efficiency uh getting back to our roots and basics of being scrappy and more bootstrapped given the market at the moment just like every startup's going through uh but it's a yeah fascinating journey and every day it was just like you're the big picture guy so what's the big picture like where's this all going like obviously linktree can continue to grow and do what it does and serve more people and all that stuff but i get this sense and i get this inkling that um that's not enough for you it's not uh first and foremost you know right now we're really focused on keeping the main thing the main thing we've got a lot more to do in the product even right now it's still day one honestly like we're 35 million linkers we refer to our users as linkers i see our tam is in the billions one yeah one two three billion anyone with an internet connection should be able to get online something i care deeply about is this idea of democratizing digital presence and really, you know, what happens if the person that had no idea how to build a website or how to have a digital presence that the world, you know, they can get online in under 20 seconds, have it their own corner of the internet, and the world can discover their talent because of it.

39:23I think that's incredibly exciting and something we care about. And so we've got so much more of that to grow and do to make it simple enough that that can happen and powerful enough that that can happen uh and that actually just becomes entirely ubiquitous and that such that you know i bump into you in the street and you give me your link not your phone number um this is the you know the the identity way of the internet and expression and curation way of the internet where anyone can express themselves not just creators and brands but actually individuals themselves and everything i care about everything that i am and so that's absolutely where it's where it's going from an expression perspective where does where does ai where does gpt where where do the technological revolutions both uh help and hinder you i've been thinking a lot about this from more broadly around the ecosystem more so than just specifically the link tree right like what happens to content creators uh what happens to artists what happens to brands and businesses and this kind of thing that's happened in a moment where creators are wanted to block their content from training models and publishers are wanting to block their content from training models uh and how does that all play out and so i think that's going to be fascinating in terms of from like a friend or foe perspective i think it's absolutely a friend uh i think it's going to be fascinating to see what people do with it for linktree you know we're thinking a lot about how we again like how do we simplify things how do we help do things for you how do we combine AI with our proprietary data.

40:49Anyone can just go and put OpenAI's tooling into something and just call it AI driven. And I think that's really boring. How do we combine that with our proprietary data such that it actually becomes exponentially more powerful for the user and really means something to them? How do we automate things for them? That's how I'm thinking about it from a product perspective. Okay. Ending with inspiration. As a former bootstrapper, now a dirty VC money funded guy. What is your advice to entrepreneurs that want to build big, incredibly fast paced, amazing, life-changing technology companies that will be inspired by your story?