#41: Alex Zaccaria, Co-Founder and CEO of Linktree — finding a need in the market, when to take venture money, preparing for board meetings, and the value of conferences
46m 35s
In this podcast episode, Alyssa Cohn interviews Alex, co-founder and CEO of Linktree, about the company's journey from a bootstrapped side hustle to a venture-backed business. Linktree was born in 2015 when Alex, his brother Anthony, and their friend Nick realized artists and creators struggled to link multiple revenue streams from social media. They built a quick prototype for their agency clients, and early signups like the Melbourne City Council showed broader demand. The company grew organically, with a pivotal moment in 2017 when Alicia Keys signed up, driving thousands of daily signups. By 2019, with 3-4 million users, Alex saw the problem expanding beyond music as the internet fragmented across platforms like TikTok. He chose to take venture capital not for money but for advisory and talent access, especially during the pandemic's tailwind. Alex emphasizes that bootstrapping taught him discipline and efficiency, which he now applies in a downturn-focused market. He also discusses learning to manage a board where members often disagree; instead of seeking alignment, he uses their opinions as inputs and fosters debate. Overall, Alex highlights the importance of being the user, maintaining conviction, and balancing offensive and defensive strategies in uncertain times.
[MUSIC] Welcome to From Startup to Grow Up the Podcast. My name is Alyssa Cohn. I'm an executive coach, an angel investor, and the author of From Startup to Grow Up. Each week, I talk to founders, creators, advisers, investors, and builders of all kinds about their insights and experiences in going from Startup to Grow Up. Welcome back and today I'm thrilled to welcome Alyssa Karyak to the podcast. Alyssa is the co-founder and CEO of Linktree. Linktree is the tool that lets you connect your socials, websites, stores, videos, podcasts, and everything else in a single Link and Bio landing page. If you've ever been on Instagram, you've seen Linktree, and you may even be one of Linktree's over 30 million users. Alyssa and I had a great discussion. We started with the founding insight and how Alex and his brother started building Linktree. What I love about the Linktree story is how they started just by seeing something that was needed in the marketplace, getting a quick prototype built, and then continuing to build it as a side hustle, to totally bootstrap for a number of years until they got to about 4 million users. Alex talked about one of the turning points of the business, which was the day that Alicia Keys signed up organically. We discussed his decision to go all in on Linktree and also to take venture money after being bootstrapped for years. And we also discussed the pros and cons of being well funded and how he continues to draw on his lessons from being a bootstrapped business. We also talked about how he's learned to manage his board and how he prepares for board meetings and how he handles it when board members disagree, which does happen pretty regularly in all companies. We also talked about Alex hired his new president, an experienced executive, and what that process was like. Alex also described the challenge in maintaining his own conviction when other experienced executives have their own equally strong conviction and how he's learned to balance that. We talked a lot about how Alex learns, his use of frameworks, and why Alex thinks conferences are so valuable. This is an incredible conversation and Alex is such an insightful founder. It was a joy to talk to him and you're going to love this discussion. So please enjoy my conversation with Alex Sikaria, co-founder and CEO of Linktree. Alex, welcome to the show. I'm so excited to have you. - Hey, Lisa, thanks for having me. - I'm so delighted to see you. Again, we met a web summit in November. We had really a wonderful dinner that Linktree put on for a number of folks. And it just, I think, goes to show you like the culture and the vibe of your company. So tell us, this is a starting point. Tell us about Linktree and what was the founding insight? - Yes, my brother Anthony and I and our friend Nick were running a digital strategy agency that specialized in music and entertainment back in 2015. So we're looking after, you know, go to market strategy for festivals and record labels, lots of others, lots of creators. And we realized through that, that there was no real way to link out of social in an effective way from my marketing perspective, really especially for artists and creators because they have so many different revenue streams. And because their industry is just so fragmented, you know, so they have their streaming on a whole bunch of different platforms for their music. And then when it comes to their touring, they got that on a hot year, they got their tickets and a whole bunch of different platforms. And then they've got their video content and another platform and then they're merged on another platform again. And so ultimately they've been out of link out to, you know, to one of these revenue streams became a real problem for them. So really we just set out to solve that problem for our clients and for ourselves. So yeah, and it turned out many more people had that problem. We built it really quickly as a quick prototype as a simple solution to that problem and put it out there and, you know, almost immediately the first sign up was the Melbourne City Council, which really kind of gave us any immediate insight. But actually this isn't just music. This is affecting everyone and there's a big implementation problem when we thought so we continue to run that as a side hustle for a while. For another few years kept running the OGTV. I just see it was scaling, you know, for a niche agency in Australia, it was scaling quickly. It was kind of doubling to tripling every year. So we grew that to that 70 people by 2019 and through that period, we're basically just agitated during the day. Link should have grown really quickly at night, mostly in the US. So we'd stay up through the night replying to support messages, trying to figure out how to keep you seeing alive. And we get to 2019 and actually what's ended up happening is we realized that it's not just the music industry that's this fragmented. It's actually the entire internet became this fragmented, right? We see the exposure to TikTok on the scene, we're pretty getting more popular LinkedIn, getting much more popular Snapchat. And so all the places you find your audience continue to explode. And then all the places you need to get your audience to actually convert them, or monetize them, or get them to wherever you need to get them to go to actually convert them, explode it as well. We saw a huge, you know, huge proliferation of creator platforms where you can monetize and third of platforms, or your commerce, all this kind of thing. And platforms continue to incentivize users more and more to keep content on their platform. And so the ability for LinkTree to be able to unify that whole digital ecosystem and to really make that a lot easier for creatives, for businesses, for brands to be able to get online and do that became even more important. - I love that. I guess you narrated so beautifully, as in, oh yeah, then we did this, then we did this. But it can't really have been like that, right? It was obviously like, oh, should we do this? No, we shouldn't do this. Like I guess I'm just curious, was, when was the moment of truth when you realized this is not just noise, this is signal, and we need to devote our time to this? - Yeah, I think that was through 28, 2019. So we were at around three or four million users by then. And there's something quite interesting about being in Australia and this lonely island on the other side of the world, where you feel like you actually just, I'll know this now that I've got many great mentors and great people around me from the US. And obviously we've teamed in the US. We were very sheltered at the time. And it felt, you know, three million users didn't seem like many. I just always assumed that there's, there's people over in Silicon Valley that had way more than that. When I first started talking about these, these are like, are you crazy? I won't be talking about. So I think through 28, 2019, we really started seeing that drove, we saw our daily signups start to continue to accelerate. There were probably a few other pinching moments on the way to really made it clear that there were, there was pretty clear signal, I think, to early 2017, the Wichikeys signed up entirely organically. I think giving the fact that we built this for music, with music in mind, that was a real validation point for us. And really that was, you know, when we had gone from, you know, it was maybe 50 signups today. And we had a, we had like this Slack integration where you would get a notification every time someone signed up. And that was fine until Wichikeys signed up. And then it went to 2000, 3000 signups today. And then it just got extremely annoying. Oh wow. Wow. But you get these like, you know, these little moments where, building that conviction over time and seeing this silver real problem for more people, way outside of a regional reason we built it. But I think it's that, I think it's still so important to one of the biggest different J this for us still, and it seems a little bit of familiar with this when it comes to product building, like having been the user yourself and having been, you know, really genuinely understanding the core problem that you're solving and how to solve it in the best way so that it actually, yeah, solves that problem for that person is completely fundamental, I think, to building a great user experience. And so all those kind of like just like building it along the way and being the user whilst being at the agency and working on behalf of these clients that we're building the product for, really made it clear that we had that signal. And every time we gave it to someone, it immediately solved the problem they had, improved their conversion, improved everything about the way they were driving their funnel. And so it really came to have what actually is the scale of this thing now. - Yeah, oh my god, I love that. I love how like you're like, we didn't have empathy for the user, we were the user. And I think it's also so interesting, you know, conventional wisdom would say, you have to go all in on your thing, but actually you're being a user and running the agency help drive insights for the product and the business itself. - Yeah, absolutely. You know, the agency taught us a few things, I think as well, it was very much, yes, we were the user because we were doing this on behalf of very start seasons and we're sort of managing a lot of entries for major artists. But then we're also, and obviously that was given us inside into what made it good to be sold. But I think just agency, the product transition is quite interesting where actually agencies are basically all about servicing the client and keeping the client happy. And it's really the same for a user, right? It's really happy.
how do we make a user happy? How do we give them the best experience? Possible, it's about, you know, learning that how to manage a team, how to grow a business, in a very harsh environment, a very frequent environment where it doesn't work, it changes very quickly. And so I think there's a lot that helped us, I think once we, in mid-2017, once we started charging for the product and actually out of the payment plan, it's seeing good revenue come through and that growing really as a big shot business. Pretty much we just consistently looked at that and we just looked at the revenue in the cost of an engineer. Like just as we were like, X amount, like the added X amount in Amarada, that's another engineer, okay? Okay, now we're gonna have higher and other engineering which is like, they were not one by one, as soon as you have a little bit of revenue and I think it got to the point where actually the revenue coming in from the tree was exceeding the agency. And I think that was one of them really kind of key seeing the point about that we need to split this out from the agency when we go, far away to spend more time directly on this. And it was actually, for better or worse, the pandemic kind of created that space for us. They were able to go do that. Given the agency was all music, it got flattened pretty quickly in the pandemic. And so that gave us the opportunity to really step away from that and go all in on ring train, which was getting us out of tailwind from the pandemic. - Right, that makes a complete sense. And so you were bootstrapping and you were profitable and then you decided to go take VC money or go out maybe and get VC money or approached. What was the journey of getting investors and what have you experiences advantage and disadvantages of now being bootstrapped first of all and now being venture back? - I think the reason we did that relates back to the Australian thing. Again, it's very hard to find people that are scaled to the scale we have in consumer business and have the advice and the right people on the table to be able to help us with that journey. We were moving from 30,000 a day to 10,000 a day to 25,000 a day to 40,000 a day pretty quickly. And understanding how to see around corners and what we should be doing with that was, still really have access to the people that are needed to be able to learn that from. So that was one of the first reasons we really started entering the phone calls from the VC's and started to, I think through those conversations and learning, you started to just be fascinated by the space and the access to the experience. So it was less about capital more about people and experience and advisory. And then obviously as we started to grow more and we got this really big tailwind set so it was really the opportunity to leap frog and we needed to make sure we could hire a team. We also had, as a big, well-served big stripe and cash-led positive people still quite difficult to compete for tech talent at the prices that were being, you know, where the market was sitting in the tech industry at the time and even now. And so you get to the point where like to be able to compete with the other funded businesses in the market, we needed to look that as well. - It turns out we learned, I think, going from bridge trap to funded. Right now I'm reflecting on it, a lot given the macro conditions. Yeah, it's really genuinely set us up in very good state in terms of the discipline and the disciplines that run sustainable growth and how to run a business, coupled with efficiency around capital. I'll be honest, it can't get easier to forget that when you're well-funded and you're just absolutely in growth at all costs mode. Which is absolutely what we, there's zero regrets. About that, we absolutely needed to do that at the time. We had a giant opportunity in front of us and it worked in many ways. But I think it does become quite easy to get very, those hard one lessons from being a bridge trap business and had a really profitably and efficiently grow a business. And so I'm really grateful I've got that experience and I could call back on that and bring that back into the fore for this year and be really sustainable through 323. - Yeah, it's such a great point. Just reflecting on that, I had Greg Galant from Mukrak on the show and he was a bootstrap business for 13 years. He just recently got, I think, private equity or VC funding or they bought part of the business. And he was talking about the what you have to go through to think about, can you hire this person? Can you hire this executive and sort of the slow plotting nature of that? And to your point, the discipline around that, I'm curious now that you have the investors and the macro environment, what kinds of conversations did you have with your investors and what did you find that they were able to give to you? Because this is a crisis that, you know, it's like we haven't really managed to require a crisis for like 13 years. And so most people who are now founders and first time CEOs are managing the first time. What are you getting from your investors in terms of advice and how to manage for this time? Like you said, there's really, so many of us founders, this is definitely the first time we're saying this. We definitely have been building out businesses through one of the biggest bull runs in history. And it's really important to remember that. I think when you're in it, it's really hard to say that. And as you kind of continue to grow and zoom out and look at the macro and you see those trends, you kind of see the moment you're in. The investors have been incredible. And I think we were very fortunate that we had an extremely competitive round. We were able to make choices around our investors in the way that we wanted to and what aligned with us. The most, you know, I was able to send a similar board and advisory and angels based on, you know, the advisory we could get and how they could lead in and dip, you know, different styles of experience. And so it's very rare that our investors or aboard agrees immediately on everything. It's a generally, I get extremely, the perspectives. And it took me a while to learn that is probably one of the biggest steps from the executive fund that is all of a sudden I have a boss which I've never had before. You know, I have people to report to, and I ask me questions that actually was it, whilst it was a shift, I've loved it because it's, excuse me, but another level of discipline and accountability and people to be accountable to, which is what I was seeking also. You know, and also my big worry for me was, you know, for a long time, I really tried to make them all happy. And it became, it's very hard to do that. You tend to learn actually, it's just about taking each of their opinions as a signal and as an input. And then it's up to you still to make the decision and just actually being able to take that advisory. And so right now the advice about all founders given all funds are giving you to focus and revenue, you know, to access the new 3x sideways is new up. - I love those expressions. - I think like, which is great from an expectation setting perspective, but I think, you know, for us, we still have a big opportunity. I do actually, we got a tailwind last time there was an economic uncertainty and I would still expect that to be the case next year. And so we just have conversations around how defensively play, how offensively we play, whilst really making sure that you're high-profile person on a capital efficiency, on our unit economics and making sure we're just being very protective through the downturn. - I love that. I especially love what you just said about learning to manage your board. I think that you are like most first-time founders. It's like the board, they seem so experienced and they're giving you these different pieces of advice and they're not agreeing themselves. And so I'm just curious, I want to double click a little bit about that. How did you kind of, was there a moment of truth that you kind of got to where you thought, oh, I get it, I have to make this decision or oh, I get it, they don't agree. And so I'm gonna have to figure this out. Is there like an example you could give about a moment that stood out for you? - Yeah, there was probably the main moment that sticks out to me is, for a board meeting, so before a board meeting I always have a meeting with each of my board members and they're getting a day reading up to it and they're sure that we're covering the right topics and the board meeting today. They're keen to hear about and to talk about and to get their perspectives and realize that three of the board members wanted to talk about in Tyler different things and not only did they want to talk about in Tyler different things specifically called out, not wanting to talk about the thing that they other person wanted to talk about and realize that actually I'm just not gonna be able to run an effective board meeting. If basically I just try to appease everyone and only talk about the things that they're calling out. And so you kind of had to just very, like, no, not for everyone, tell me these are the things that companies talk about and these are the things that I need advice on. And obviously they were super aligned with that. They were happy to talk about whatever it is that we need to talk about, you know, they're not, I think I'm not talking about 'cause they, you know, someone else wants to, everyone, gets along amazingly, we get the advice we need. But I think that was my more or less at all. (laughs) I should not be aiming for a line here. I should not be aiming for a line here.
should just be aiming actually for provocation and building debate and building ways for actually the board meeting to be people debating and actually talking about finding that true through tension and helping you meet that advice. That's really the way I take signal. Obviously they're expecting an outcome after the board meeting, committee come back with some time they can make it out because I've just got two entirely different perspectives, but generally in my experience is led to way high quality decisions because I can see around corners and see both sides. Often the opinion of another is just, even though it's contrary, it's because of an experience or something that I haven't seen before. That's giving me that insight and make sure that I don't run into it in this decision. I love it. I love your expression, "Truth through tension." I'm going to steal that for sure. I stole that. I stole that from my president, Michael Senn. He loves it so much that we made a tation for him. That said, that's it. Oh my God, I love that. Well, I was going to ask you about Michael Senn. Let's talk about him now since you mentioned him. You brought him in. I think this year is that right, Michael Senn? What drove that decision to bring in Mike, who was an experienced executive, I guess, from Twitch and Pandora? What drove a decision? Well, I think of myself as a product-led founder. I think where I find what fills my cup of most and where my geniuses would be around the product and where my geniuses definitely wouldn't be in a lot of the other areas of the business and just wanted to find people smarter than me, around the table and essentially wanting to speak my reports that I can spend more time on the product. So essentially, rather than going for a COO specifically, I went, I was looking more for a president of all that could take in and look after more of the day to day running in the business. So he looks after pretty much everything outside of marketing, product and tech. So that's people, legal and opt strategy and commercial as well. He's got experience kind of across the board in all of those areas. So that's been really awesome to console and add all of that report and hit those reports and run that part of the business. And then for me to be able to lean in much more heavily on the product side of the business has been, yeah, it's worked really well. And obviously bringing in the other thing we're looking for in that role is someone that can help bring the kind of Australian culture along for the journey towards the US culture a little bit. Given so many of our users, based in the US, we're building a team in the US, we knew we would need to be able to find a way for those cultures to work really well together. And there are some nuances. And so finding that person has the key to be able to show the, you know, show the Australians how the US team, the culture on the US team and around the US uses, pace uses was really important. Like, you know, show them how to break glass instead of just breaking the glass. And I think it's like a really important travel and marketing is absolutely masterful like that. That's what I want to ask you so many questions about that. First of all, it's hard enough finding the right president, quote unquote, you know, the right partner or the CEO and founder. It's hard enough finding that person. It's hard enough kind of embedding them into the culture. And it's really hard for founders to let go. Like they say they want to let go. But then this person brings a whole bunch of process and not only the process and you know, sort of checking around, but it sounds like you were able to navigate all three of those stages. What, I guess I'm curious, like, how did you go about and find Mike? What were you looking for when you found him? And how did you make sure he was going to be really embedded into the culture so that it would be acceptable and a success? So the search for a while, we, the way we approach this search was either CEO or president and we, and we, so we saw a lot of candidates cost both. And generally, I like to do it that way because I can, I can pick up in the signal between the two styles, where he's re-roving, rather than rocking my brain and just dividing one singular J.D. around a particular role. I, you know, took work with us and searched them on, hey, let's look for both these roles. I want to see candidates of both styles and both experiences and through the questions in the way they answer questions, I'll get a bit of fear for what we're actually looking for and I can build a role around that. I think it's, it is important to, to try and obviously start with the role and what the problem's been in its soul. They're trying, you know, we can, at a role at that scale, without many reports, we have room to, to maneuver different reports, states and their genius zones and where they're going to be really effective. We needed to add, we had a pretty rigorous process, we had a, you know, did a task that he presented, we spent a lot of time, we did, you know, it was through the pandemic, so we couldn't meet him person and through that period of more hiring executives, I always found a really important step was just to actually just have like a two-hour call in the evening with a wine or a drink and just be able to talk, not in interview style, but about family and life and just actually as if you were able to go out and drink and hang out and I think like finding those aligned interests and intenties between our suspenders and like and they can't, and I think we found that really clear with Mark, because we had shown through in terms of just his approach, his energy, the way he answered questions, you could see the ECU showing through and then obviously experience clear experience in key areas of that role and then also what I was looking for was giving it was such a widespread role, so many reports across so many different functions, finally, actually my experience at Twitch and Amazon company where they have single credit leadership, generally where they have to manage one part of the business across many functions is really important experience and how to manage between the different functions and build cross-functional process, which is really what we're looking to do, I didn't really want to be, I didn't think it was the most effective use of my time to be leaning in that way, to building the option process and commercial side of the business and finding some of my experience and saying yeah, it can go wrong a lot of the time and I think there's a degree of luck here rather just like, okay, once they're in there, once they're in the seed, how do we get along and then how do we actually do that report together and I think yeah, we're just getting along really well. That's great, that's wonderful. What surprised you the most about bringing it up president or about bringing Mike or about how he executed? I think they experienced from the scale, I think it was just like actually probably realizing the amount of things we were doing quite on quite wrong. But I think there's just these things just through figuring it out and then when you're bringing in someone's experience like that, actually showing that either the right way to do it or a different way of thinking. I think there's a learning there as well, like you tend to, or at least something I learned was starting to bring in very experienced execs. I'm doing that very clearly for their experience and for their talent and for finding ways smarter than people that may or want to be the dumbest person in the room. I think once that actually, that is really easy to say when you're just driving and you're like, you're able to speak things out because you're doing it yourself. And to still have the level of conviction you had in the first place when you've got other people with extremely high conviction in an opposite direction to you for the first time, is it learning in itself what I can have it to go and trust my own semi-actually acting really trust you can be actually not just salad. And that was a big beachy of smear this year. I think in testing my, just like, oh hang on, this is something I've always believed in now, someone who has a completely different perspective and they say it with absolute conviction and absolutism, which is great because it pressure tests me and then I've had many times on my, actually cool, you're right, let's go do that and then end it up not being the case and realizing I should have trusted myself. And then there's been many times as well, well as entirely wrong and never arrived and I think it's, you know, it's just finding that place that experimentation culture and the times of trust yourself and the times to be able to let go. It's a journey. Oh my God, it's such a journey. Do you think that there's really a way to know with experience, when to trust yourself and when to let go because, you know, the other person's more experienced or whatever, or do you just think that best you can, you make a decision and then you course correct if it's wrong? Yeah, I think there's times of cool, you know, times of cool for both. I like to use the one way door to a door framework. If it's a one way door, then I think we'll spend a bunch of time with debate on it and at some point, so many disagreeing community, or at some point we need to trust one or the other and that's great and obviously, as long as we learn from it, that's great. Every way door, it's just really important to me, it's quickly as we possibly can, and yes, let's just make it happen and we'll course correct or reverse it or do what we need to do there. And I think that's something that becomes, yeah, that's definitely something as we've grown become harder to maintain that pace and decision, you know, to make sure that we are [BLANK_AUDIO]
quickly on decision-making and on two-way doors and being comfortable learning from it. But yeah, I, in terms of trust in my, I'm still learning about that exact signal we actually really push hard enough and where I should really trust the people that I'm deliberately high for that specific reason to tell me I'm wrong but instead in areas that yeah. So that's yeah. I'm sure that I'll tell you I haven't haven't figured it out yet but get in there. Every one, every day, one foot in front of the other. Now Alex, you had, I mean like all like all startups, you've had some ups and downs, you were bootstrapping, you got investment, you were like this high flying unicorn and then in continuing to really progress and then at some point earlier in this year you've done a few layoffs, can you talk about kind of what drove that decision and also what was that like for you personally? How did you handle that? Yeah, I mean this was definitely the low light of the year or I've built in the company. I think we, as I said earlier, was like we needed to go or in growth, drive an opportunity in front of us, the market called for it and it was an opportunity to really scale the team and seize that. I think that's definitely made some wrong decisions around that. I think as the, like we're speaking about earlier, I think that as founders in this market, you kind of, it's kind of, it's kind of easy to think that that's going to continue going. It didn't and I think it really, there's a bunch of realities around the way we need to run the business and the way you know how long we need capital to last and those kinds of things but most importantly around our strategy and realizing, you know, after a whole bunch of learnings, things that are working, things that aren't working, re-erlining our strategy of realizing that there's some areas of the business and some roles that are not imperative for the following year and so we have to make that call. Obviously, personally is incredibly tough. I don't want to call the attention of myself and our tough horsemen. It was obviously much tougher for those impacted and I was just mostly concerned for those obviously, those people obviously have the remaining team members as well and we think that their teammates, BL is kind of like, you know, easily one of the hardest days of my life and they'll lead up to it and it's the management around that as well. Like, you know, every person in the executive team crying and being, you know, genuinely, all of us genuinely very affected by it is, yeah, obviously very heart wrenching and to be learning moment, I think a big, big moment to obviously learn from and think about in terms of how we really make sure we're super clear on our strategy and super clear on how we're hiring to that strategy. I think touching on the bootstrap learnings, like that was probably where I was most disappointed in myself, right? Like I had that sustainable experience and doing it in a business and then we jumped into the way we needed to run and I, like I said, there wasn't regress necessarily about that. That was the opportunity at the time and the way we, the reason we brought on capital and the way VC funded businesses work is that we should be hiring ahead of our revenue curves to go and innovate and build product and scale. And so we needed to do that ultimately realizing with a bunch of new inputs that we needed to change our strategy and ultimately obviously you can't help but blame yourself if you can't help. And you know, and it is really important to like to see the recycling understand what were these regions that were at this point and now we make sure we learn from it. And so absolutely it was on me, it was on our team in terms of these decisions. So super disappointing. Yeah, it was, yeah, it was a rough, rough week. Yeah. So I can, I can totally imagine it. Thank you for sharing all that. It's, you know, an important thing that actually all founders at some point have to face. I'm struck really by the way you articulate yourself and how it's so clear you're such a learner, you're a flexor and you're a learner. And I'm curious because you as a, as a founders of CEO have to learn so rapidly, how do you, what things do you seek out to handle your own learning and to make sure you're continuing to develop kind of above the curve of the company? This is something I'm working on a lot. I learned about myself that I learned through doing and so generally just throwing myself into situations and to make sure I'm learning from them and I gather the answer the best way to me to synthesize that I found is to get an exact coach so that I can be real time tour. Yeah, you're going to be a coach. Absolutely. Number one, getting exact coach reminds me of incredible and like I can talk through these thoughts and feelings and learnings or vent or you'd be frustrated or be happy and just like really cool after learnings that and apply frameworks to it. I think I never went to university. I didn't think in, I didn't think in frameworks and so like when I'm going through something and then be able to apply that kind of framework to think into it, it's definitely, it really helped me to synthesize that learning and take notes about it. I love to read books but I don't read books enough and I'm not an extremely quick reader. So if I need to learn something rapidly, I generally won't turn to a book. If I need to learn something more map through just overall, I'll turn to a book about it and when in the way of read books is I read it and I listen to the audio book at the time which helps me retain, I can read way faster because I put it on like 3x and I can absorb the information at 3x and retain it really well with both the reading and the listening. So if I'm trying to learn something from a book, I'll do it that way for trying to just enjoy like a kitchen book. It will take a much more relaxed approach and then podcasts, absolutely not podcasts. Again, then I would have speeded up but mostly around product like Lenny's podcast, Lenny or VC20, yeah, just finding a very specific topic and learning from people that have done it before me, generally I'll learn that a lot quicker. And then advisory, I think building a mental network and building an advisory and that's why it specifically chose out angels and out investors so I can pick up a phone and ask them and talk to them and why we met at a conference, why I find conferences valuable, they take a bunch of time but then to be able to go meet amazing founders and CEOs that I can build a network with, I actually build a proper relationship with such that I can take some of the people to phone, it's not like this transactional Zoom conversation. And important for me to be again being in Australia, I think when you're in a city where lots of those people are around, you can go out and launch it and build that relationship, that doesn't happen in each amount here. It's very, very transactional Zoom conversation since I'm really going and being very deliberate and intentional about building those relationships so that I've got a mix of CEOs and founders that on the same part of the journey as me that we're learning together and we can call each other and console each other or people that are at step ahead of me. And then a final thing I'll say is mentoring others and so I do some angel investing, I started a angel synchid and a small fund here in Australia, mainly so that I can access new founders and be able to be able to give back the community and also advise and mentor mostly because I just find it's one of the best ways to make it synthesize my learnings. I just find that I actually go into it thinking I know nothing about this topic that I want to talk about but I end up having a lot to say and it makes me really gather all my thoughts around it and actually end up leaving those meetings having learned something that I already knew that I would categorize and be able to take it more clear about it. So that's fascinating. Yeah, that is fascinating. When you explain it to somebody else you suddenly do realize both how much you know and also how you're pulling from all these different elements. I think that's great. And I appreciate that you're also finding founder networks of so important. One thing that so many founders deal with is imposter syndrome or severe self doubt and I'm just curious have you encountered or experienced imposter syndrome? Yes, I mean absolutely more recently than ever. I think I touched on it earlier. I don't think I really found it that much when I was more time to go and handle the wheel. I think I kind of just like swamp for the fences just always have an attitude that I can do anything and we'll figure it out. And it's fun like there's so much I hate the term fake and make it but there's so much of like just figuring it out. Little story when I when we started the agency I went into a festival and convinced him I knew what I was doing with digital marketing. They gave me $1,000,000 to expand the media and it was the first time I'd signed up that I'd never used it before in my life. And we tripled the conversion rate like it was just I spent basically getting all noticed where we can just pick it out. And I think doing that a bunch of times means
kind of lose any processing, you kind of just know that you can do it. And I think in that zone of uncomfort, it's actually where I learned the most, and so I lived comfortably there. More recently, I feel a little more as I've surrounded myself with people we've seen a particular experience in particular areas. And so then when it's worth it outfinger to outfinger yourself and more about explaining to others, your thoughts and what you think are given them the space to do it, yeah, that's when you can definitely feel it. It's an interesting feeling. Yeah, how have you overcome it when that does come up for you? I think I just name it mostly. Like I'm very, you know, build that relationship with my team where I just really name what I don't know something well, and this is why I need you around it or I'm going to go learn it or how we can figure this out together. Or because then that way, or that, that gives you the space then when you do know something, you can really try to be an honest, say, hey, I'm experienced here and we can lean in on that experience more. Outside of that, if I'm not naming it, it's really just being comfortable with the process knowing that actually it's the way I've learned a million times before, and I'll look back at this moment in six months and realize it's actually the easiest thing I've ever done. And whatever I'm doing with this, the expanse is going to be way harder. And so that's fine. One call out on Impossessingium. There's a really great take talk from Mike Cannonbrook's on Impossessingium. Yeah, it's just like a very Australian approach to Impossessingium, but it's super independent, but I think it for someone like him. And he is the founder of Atlassian. Atlassian, yes, I saw that Ted talk. It's fantastic. Everyone should watch it. Yes, it's great. I think to what you think like that, where you realize that actually even someone like him feels like has no idea what he's doing in H.A. That's completely normal and fine and absolutely exactly what you should be. If I, you know, no one, especially fam is in a high scale group, like if you feel like you know what you're doing in H.A. You're definitely not either pushing yourself or pushing the company hard enough. And so I think that's fine. Alex, just a couple of more questions. What do you wish you had known earlier on your journey? I would say just say probably this, probably the scale that Winctree would get to. That might have been better to start that journey earlier rather than waiting for years and running the agency and making sure the side hustle. That's definitely, you know, we think about that a lot actually. And I do think everything happens for a reason in that regard. And actually so much the way we built Winctree as a side hustle and through sheer kind of grit and determination and bootstrapping it actually kind of led to the sale of productities and the patience to grow with our users, learn from our users. If we were just for Winctree, I think we would have made different decisions because we would have had the drive, revenue in a different way. We would have had to, you know, push users into a higher plan earlier these kinds of things. And I think, yeah, so even those kinds of things, you know, where like yes, it would have been great to know about this and do it earlier. Actually, don't know if it would be the same product. And I think that's meaningful. I think as well, just like the learnings, just kind of like so much of what I know now about how to hire and how to integrate executive and build a team and you know, do that from the outset. And just how to construct the team. I think you end up with all our trials and tribulations and the last two years of hiring great people and hiring also great people and the impact that makes some of business. And so taking those learnings a lot earlier, I would say. Last question. What advice do you have for other founders as they embark on their journey to grow into leaders? So I think the first is to learn how to trust yourself and back yourself. If you're going to do it, be ready to back yourself is going to be plenty of people to tell you not only like not that you're necessarily that you're wrong. It's not an idea, but just particular ways of doing things. And I think ultimately if you trust yourself and do it your way, you can learn from yourself rather than doing it their way and we really spend the rest of the time reaching you get it your way. You can exact coach. That's definitely a good one. As soon as you can afford it, five mentors. One of, I've worked this year as well is nothing is ever is good or is bad as it seems. I've heard that a bunch of times from people and it's never really meant that much. But I think it's when you do that, it can be really, you know, things can seem dire. There's always a way out of it. And then, you know, like I said, six months later, it's kind of seemed like a bit. And also when things are amazing, that's also never as good as it seems and that's ultimately going to change as well. So being able to keep steady on that. And then finding ways to communicate your vision and articulate that it's something that I have not nailed at all because our vision is so vast. And it's something that is like quite difficult to really put into very clear words. But being able to find a way to do that in different means of communication, different modes of communication for different people understand it. And make it and be able to just communicate it every single day as you scale. It's just so important. Love it. Great advice. Great advice. Alex, it's such a joy to talk to you. I really appreciate all the insight that you shared. And I'll just say that a lot of people are going to get a lot of this. So thank you so much for your time. Well, it's a nice of thanks so much for having me. Thank you. Thanks for listening to from Startup to GrownUp. If you like what you heard, give it a review on Apple Podcasts so other people can find it. And if you know of a founder or someone else who is meant to be on this podcast, drop me a line through my website, alissacon.com. [BLANK_AUDIO]
Podcast Summary
Key Points:
Linktree was founded in 2015 by Alex and his brother Anthony, along with their friend Nick, initially as a side hustle while running a digital strategy agency for the music industry.
The founding insight was the need for a single link to consolidate multiple revenue streams (streaming, touring, merchandise) for artists and creators on social media.
The company bootstrapped for years, reaching 3-4 million users by 2019, with key validation moments like Alicia Keys signing up organically in 201
Alex decided to take venture capital primarily for access to experienced advisors and talent, not just capital, as they scaled rapidly during the pandemic.
Lessons from bootstrapping—discipline, capital efficiency, and sustainable growth—remain crucial, especially in the current economic downturn.
Managing a board involves learning that disagreement is normal; Alex now focuses on using board input as signals, not directives, and aims for provocation and debate rather than unanimous alignment.
Summary:
In this podcast episode, Alyssa Cohn interviews Alex, co-founder and CEO of Linktree, about the company's journey from a bootstrapped side hustle to a venture-backed business. Linktree was born in 2015 when Alex, his brother Anthony, and their friend Nick realized artists and creators struggled to link multiple revenue streams from social media. They built a quick prototype for their agency clients, and early signups like the Melbourne City Council showed broader demand.
The company grew organically, with a pivotal moment in 2017 when Alicia Keys signed up, driving thousands of daily signups. By 2019, with 3-4 million users, Alex saw the problem expanding beyond music as the internet fragmented across platforms like TikTok. He chose to take venture capital not for money but for advisory and talent access, especially during the pandemic's tailwind.
Alex emphasizes that bootstrapping taught him discipline and efficiency, which he now applies in a downturn-focused market. He also discusses learning to manage a board where members often disagree; instead of seeking alignment, he uses their opinions as inputs and fosters debate. Overall, Alex highlights the importance of being the user, maintaining conviction, and balancing offensive and defensive strategies in uncertain times.
FAQs
Linktree is a tool that lets you connect socials, websites, stores, and other content in a single bio landing page. The founders created it in 2015 because artists and creators needed an effective way to link out from social media to multiple revenue streams.
They built a quick prototype and saw immediate sign-ups, including from the Melbourne City Council. Organic sign-ups from celebrities like Alicia Keys in 2017 signaled strong demand, and daily sign-ups grew from 50 to thousands.
The founders ran a digital agency and only focused on Linktree at night. By 2019, with 3-4 million users and revenue exceeding the agency, they realized the problem was widespread beyond music, prompting a full pivot.
They needed access to experienced advisors and capital to scale quickly, especially to compete for tech talent. The decision was driven by a desire for people and expertise, not just funding.
It instilled discipline in sustainable growth and capital efficiency. This helped them navigate economic downturns, like in 2023, by focusing on revenue and unit economics.
He meets with each board member before meetings to align on topics. He learned not to appease everyone but to seek provocation and debate, using their opinions as signals while making his own decisions.
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