#41: Alex Zaccaria, Co-Founder and CEO of Linktree — finding a need in the market, when to take v...

In this episode of the From Startup to Grownup podcast, host Alisa Cohn interviews Alex Zakaria, co‑founder and CEO of Linktree. Alex explains how he and his brother identified a market need for a single‑link bio tool while running a digital‑strategy agency for music and entertainment clients, built a quick prototype, and grew Linktree as a side‑hustle. He describes the "pinch‑me" moments that proved product‑market fit – notably Alicia Keys signing up – and how the business transitioned from bootstrapping to venture‑backed growth. Alex discusses the strategic reasons for taking VC money (access to talent, capital efficiency, advisory support), the challenges of managing a board with divergent opinions, and the process of hiring a president (Michael Olson) to run day‑to‑day operations while preserving culture. He shares decision‑making frameworks (one‑way vs. two‑way doors), the painful layoff round, and how he copes with imposter syndrome. Alex outlines his personal learning system: executive coaching, accelerated book/audio consumption, podcasts, mentorship networks, and mentoring others. He concludes with advice for founders on trusting oneself, building a vision communication strategy, and staying balanced through highs and lows.
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Welcome to From Startup to Grownup, the podcast. My name is Alisa Cohn. I'm an executive coach, an angel investor, and the author of From Startup to Grownup. Each week I talk to founders, creators, advisors, investors, and builders of all kinds about their insights and experiences in going from startup to grownup. Welcome back, and today I'm thrilled to welcome Alex Zakaria to the podcast. Alex 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 in 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. Alex 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, totally bootstrapped 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 how 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 gonna love this discussion. So please enjoy my conversation with Alex Zakaria, co-founder and CEO of Linktree. Alex, welcome to the show. I'm so excited to have you.
Hey, Alisa Cohn, thanks for having me.
I'm so delighted to see you, uh, again, we met at Web Summit in November and we had a 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, just as a starting point, tell us about Linktree and what was the founding insight?
Yeah, so my brother Anthony and I and our friend Nick were running a digital strategy agency that specialized in music and entertainment back in 2015. Uh, so we're looking after, you know, the go-to-market strategy for festivals and record labels, uh, lots of artists, lots of creators.. And we realized through that, that there was no real way to link out of social in an effective way from a marketing perspective, really, especially for artists and creators because they have so many different revenue streams and because their, 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, you know, they got their tickets on a whole bunch of different platforms., and then they've got their video content on another platform and then their merch on another platform again. And so only being able to 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. Put it out there and, you know, almost immediately the first sign-up was the Melbourne City Council, which really kind of gave us that immediate insight that actually this isn't just music, this is affecting everyone and there's a bigger fragmentation problem than we thought. So we continue to run that as a side hustle for a while, for another few years, kept running the agency. The agency was scaling, you know, for a niche agency in Australia, was scaling quickly. It was kind of doubling to tripling every year. So we grew that to about 70 people by 2019. And through those period, that period, we're basically just agency during the day. Linktree was growing 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 this thing 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 explosion of TikTok on the scene, Twitter 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, to actually convert them or monetize them or do get them to wherever you need to get them to go to actually convert them exploded as well. We saw a huge, you know, huge proliferation of creative platforms where you can monetize and further platforms for e-commerce, all this kind of thing. And platforms continue to incentivize users more and more to keep the 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 creators, for businesses, for brands, to be able to get online and do that became even more important.
I love that. I guess I'm just— you narrated so beautifully as in, oh yeah, then we did this and 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 2018, 2019. So we were at around 3 or 4 million users by then. And there's something quite interesting about being in Australia on this lonely island on the other side of the world where you feel you actually just— I've noticed now that I've got many great mentors and great people around me from the US and obviously with our team in the US. We were very sheltered at the time and it felt, you know, 3 million users didn't seem like many. I just always assumed that those people over in Silicon Valley that had way more than that. When I first started talking to VCs, they're like, are you crazy? What are you talking about? So I think through 2018, 2019, we really started to see that grow. We saw our daily signups start to continue to accelerate. There were probably a few other pinch me moments along the way that really made it clear that there were, there was pretty clear signal, I think. So early 2017, Alicia Keys signed up entirely organically. I think given 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 a day, and we had a, a, we had like this Slack integration where you would get a notification every time someone signed up. And that was fine until Alicia Keys signed up. Uh, and then it went to 2,000, 3,000 signups a day, and then it just got extremely annoying. Wow. Wow. But you get these like, you know, these little moments where, uh, building that conviction over time and seeing this solve a real problem for more and more people way outside of the original reason we, uh, built it. But I think it's that, I think it, you know, it's still so important. It's one of the biggest differentiators for us still. And it seems a little bit ephemeral, but 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, 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, you know, how, what, 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, 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 helped drive insights for the, 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 had, we were the user because we were doing this on behalf of those types of users and also managing a lot of Linktree for major artists. But then we'll also, and obviously that was giving us insight into what needed to be solved. But I think just agency to product transition is quite interesting where actually agency is like basically all about servicing the client and keeping the client happy.. And it's really the same for a user, right? It's like really, how do we make a user happy? How do we, how do we give them the best experience possible? It's about, you know, learning about how to manage a team, how to grow a business in a very harsh environment, a very difficult environment where if it doesn't work, it changes very quickly. And so I think there's a lot there that helped us. I think once we, in mid-2017, once we started charging for the product and actually added the payment plan and seeing good revenue come through and that growing really as a bootstrap business, pretty much we just consistently looked at that and like we just looked at the revenue in the cost of an engineer. Like as soon as we get like X amount, like added X amount in MRR, that's another engineer. Okay, okay, now we can hire another engineer. We're just like building it one by one as soon as we had a little bit of revenue. And I think it got to the point where, uh, actually the revenue coming in from Linktree was exceeding the agency. And I think that was one of the really kind of key signal points. We're like, all right, we need to split this out from the agency. We need to go, uh, find a way to spend more time directly on this. Um, and it was actually, for better or worse, the, uh, pandemic kind of created that space for us to be able to go do that. Given the agency was all music, it got flattened pretty, pretty quickly in the pandemic. And so that gave us the opportunity to really step away from that and go all in on Linktree, which was, which was getting a solid tailwind from the pandemic.
Right. That makes complete sense. And so you were, you were bootstrapping and you were profitable and then you decided to go take VC money or go out maybe and get VC money. You were approached. What was the journey of getting investors? And, and what have you experienced as advantages, disadvantages of now being, of being bootstrapped first of all, and now being venture-backed?
I think the reason we did that, it relates back to the Australian thing again. It's, you know, it's very hard to find people that have scaled to the scale we have in consumer business, um, and have the, you know, have the advice and the, and the right people around the table to be able to help us through that journey. We were moving from 3,000 a day to 10,000 a day to $25,000 a day to $40,000 a day pretty quickly. And understanding, you know, how to see around corners and what we should be doing with that was, you know, I just didn't really have access to the people that I needed to be able to learn that from. So that was one of the first reasons I really started, you know, answering the phone calls from the VCs and starting to, you know, I think through those conversations and learning, it 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, saw it as a really big opportunity to leapfrog, and we needed to make sure we could hire a team. We also had, you know, whilst we're bootstrapped and cash flow positive, it was 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 at that as well. In terms of what we learned, I think going from bootstrap 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 around sustainable growth and how to run a business coupled, you know, with efficiency around capital. I'll be honest, it can get easy to forget that when you're well funded and you're just absolutely in growth at all costs mode, which is absolutely what we— I, 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, you know, those hard-won lessons from being a bootstrap business and how to really profitably and efficiently grow a business. And so I'm really grateful that we've got that experience and I can call back on that and bring that back into the fore for this year and Yeah, be really sustainable through '23.
Yeah, it's such a great point. Just reflecting on that, I had Greg Gallant from Muck Rack 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? You know, 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 through 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 through this time?
Like you said, there's really, for so many of us founders, this is definitely the first time where we're seeing this. We definitely have been building our 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, it's really hard to see 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 were in. Our 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 assemble a board and advisory and angels based on, you know, the advisory we could get and how they could lean in and give, you know, different styles of experience. And so it's very rare that our investors or our board agrees immediately on everything. And so generally I get extremely different perspectives and it took me a while to learn. That is probably one of the biggest steps from bootstrap to funded is like all of a sudden I have a boss, which I've never had. Before, you know, I have people to report to, they're asking me questions. That actually was it. Whilst it was a shift, I've loved it because it's— it gives me another level of discipline, uh, and accountability and people to be accountable to, which is what I was seeking also, you know. And also a big learning 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 them, each of their opinions as signal and as an input, and then it's up to you still to make the decision, um, and just actually being able to take that advisory. And so right now the advice is like all founders are given, all funds are giving, is to, to focus on revenue. You know, it is, you know, uh, 2x is the new 3x, uh, sideways is new up.
I love those expressions.
I think like, which is great, uh, 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, you know, economic uncertainty, and I would still expect that to be the case next year. Um, and so we're just having conversations around how, um, how defensive we play or how offensive we play whilst, you know, really making sure that it's hyper-focused on, on, uh, capital efficiency, on our unit economics, and making sure we're just being very protective through the downturn.
I love that. Um, I especially love what you just said about, you know, 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 going to 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 for me is preparing for a board meeting. So before a board meeting, I always have a meeting with each of my board members in the days leading up to it to make sure that we're covering the right topics in the board meeting that they are keen to hear about and to talk about and to get their perspective. And realized that 3 of the board members wanted to talk about entirely different things and not only didn't want to talk, wanted to talk about entirely different things, specifically called out not wanting to talk about the thing that the other person wanted to talk about. And realized 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 name that for everyone, tell them these are the things that companies talk about and these are the things that I need advice on. And obviously they're all super aligned with that. They're all happy to talk about whatever it is that we need to talk about. You know, they're not going to not talk about because they, you know, someone else wants to. Everyone gets along amazingly. We get the advice we need. But I think that was the moment where I was like, oh, uh, I'm— I should not be aiming for alignment here. I should just be aiming actually for provocation and building debate and building ways for actually the board meeting to be people debating an issue, um, and talking about, um, you know, finding that truth through tension and helping give me that, that advice. That's really the way I can take signal. Obviously then they're expecting an outcome after the board meeting for me to come back with. And sometimes it can make it harder because I've just got two entirely different perspectives. But generally, you know, in my experience, has led to way higher 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. And that's given me that insight to make sure that I don't run into it. In this decision.
I love it. I love your expression, truth through tension. I'm gonna steal that for sure.
I stole that. I stole that from our president, uh, Michael Olson. He loves it so much that we made a t-shirt for him, uh, that said that. So, um, oh my God, I love that.
Well, I was going to ask you about Michael Olson, so let's talk about him now since you mentioned it. You brought him in, I think, this year. Is that right? Mike Olson. What drove that decision to bring in Mike, who was an experienced executive, I guess, from Twitch and Pandora? What, what drove a decision?
So I'm a, I, I think of myself as quite a product-led founder. I think where I find the, you know, what fills my cup the most and what I, where, you know, where my genius zone would be, would be around the product. And where my genius zone definitely wouldn't be, would be in a lot of the other areas of the business. And just wanted to find people smarter than me being around the table and essentially wanted to shrink my reports so that I can spend more time on the product. And so essentially, rather than going for a COO specifically, I went— I was looking more for a president role that could take in and look after more the day-to-day running of the business. So he looks after pretty much everything outside of marketing, product, and tech. So that's people, legal, and ops, strategy, and commercial as well. He's got experience kind of across the board in all of those areas. And so that's been, yeah, really awesome to, to consolidate all of that reporting with 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, uh, 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 like the US culture a little bit. Given so many of our users are 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 who has the EQ to be able to show the Australians how the US team, the culture around the US team and around the US users, base users was really important. And like, you know, show them how to break glass instead of just breaking the glass. I think it was like a really important trait we're looking for. And Mark is absolutely masterful at that.
That's why 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 then it's really hard for founders to let go. Like they say they wanna let go, but then this person brings a whole bunch of process and I don't like 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 gonna be really embedded into the culture so that it would be acceptable and a success?
So the search went for a while. The way we approached the search was either COO or president. And so we saw a lot of candidates across both. And generally, I like to do it that way because I can pick up on the signal between the two styles more easily rather than racking my brain and just writing one singular JD around a particular role, I would, you know, to work with a search firm on, hey, let's look for both these roles. I wanna see candidates of both styles and both experiences. And through the questions and the way they answer questions, I'll get a better feel for like what we're actually looking for and I can build the role around that. I think it is important to try and obviously start with a role, what the problems we need to solve. We try and like, you know, we can at a role at that scale with that many reports, we have room to to maneuver different reports based on their genius zones and where they're going to be really effective. Leading into that, 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 in person. And through that period of more hiring executives, I always found a really important step was just to actually just have like a 2-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 have a drink and hang out. And I think like finding those aligned interests and intentions between us as founders and Mike and the candidate. And I think we, you know, we found that really clearly with Mike. It shone through in terms of just his approach, his energy, the way he answered questions. You could see the key shone through. And then obviously experience, clear experience in key areas of that role. And then also what I was looking for is, given it was such a widespread role with so many reports across so many different functions, finding like, actually Mike's experience at Twitch and an Amazon company where they have single-threaded leadership generally, where they have to manage one part of the business across many functions. Is really important experience on how to manage between those different functions and build cross-functional process, which was 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 deeply into building the ops and process and commercial side of the business. And someone, you know, finding someone that's had that experience. And so yeah, it can go wrong a lot of the time, and I think we're there's a degree of luck here as well, right? Of just like, okay, once they're in the, once they're in the seat, how well do we get along? And then how do we actually build that rapport together? And I think, yeah, we're just, yeah, getting along really well.
That's great. That's wonderful. What surprised you the most about bringing in a president or about bringing in Mike or about how he executed?
I think just the experience from the scale. I think it was just like actually probably realizing the amount of things we were doing quote unquote wrong. Like, you know, I think there's just things you just do through just figuring it out. And then when, you know, bringing in someone experienced like that, actually showing them either the right way to do it or a different way of thinking. But 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 for their talent and for finding way smarter people than me. I want to be the dumbest person in the room. But I think once that actually— that is really easy to say when you're just driving and you're like, you're able to just figure things out because you're doing it yourself. Learning 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 a learning in itself, of like having to, having to go and trust. Like, all of a sudden you actually have to really trust your conviction, not just sell it. And that was a big, big shift for me this year, I think, in testing my— just like, oh, hang on, this is something I've always believed, and now someone who has a completely different perspective, and they say it with absolute conviction and absolutism, which is like, which is great, uh, because it pressure tests me. And then I've had many times where I'm like, actually, cool, you're right, let's go do that. And then ended up that not being the case and realizing I should have trusted myself. And then there's been many times as well where I was entirely wrong and they were right. And I think there's, you know, it's just finding that place, that experimentation culture and the times to 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 you do the best you can, you make a decision, and then you course correct if it's wrong?
Yeah, I think there's times to call, you know, times to call for both. I like to use the one-way door, two-way door framework. If it's a one-way door, then I think we'll spend a bunch more time, we'll debate on it, And at some point someone needs to disagree and come in, or at some point we need to, uh, trust one or the other. And that's great. And obviously as long as we learn from it, um, that's great. Two-way door, uh, which is just really important to move as 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. Um, and I think that's something that becomes Yeah, that, it's definitely something as we've grown become harder to maintain that pace and decision, you know, making sure that we are moving real quickly on decision making and on two-way doors and being comfortable with learning from it. But yeah, I, in terms of trusting, like, I'm still learning like that, that exact signal where I should really push hard enough and where I should really trust the people that I've deliberately hired for that specific reason to tell me I'm wrong in certain areas that Yeah. So, that's— yeah. I'm sure they'll tell you I haven't figured it out yet, but get in there.
Everyone, right? Every day, one foot in front of the other. Now, Alex, you've had— I mean, 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 continuing to really progress. And then, at some point earlier 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, the, obviously the lowlight of the year, or of building the company. I think we, as I said earlier, I was like, we needed to go all in growth, giant opportunity in front of us. The market called for it, um, and it was an opportunity to really scale the team and seize that. I think that's, you know, we definitely made some wrong decisions around that. Uh, I think as the, you know, Michael was speaking about earlier, I think that as founders in this market, you kind of— it tends to be easy to think that that's going to continue going, uh, and it didn't. And I think it really— there's a bunch of realities around the way we need to run a 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, realigning our strategy and 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 it was incredibly tough. I don't want to call the attention to myself and how tough it was for me. It was obviously much tougher for those impacted. And I was just mostly concerned for those people obviously, and for the remaining team members as well, and losing their teammates. But yeah, it was kind of like easily one of the hardest days of my life, and the lead up to it. And the— you know, 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 a big learning moment. And I think a big, big moment to, to obviously to learn from and, and think about in terms of like 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, uh, experience in building a business, and then we jumped into the way we needed to run. And I— and like I said, there wasn't regrets necessarily about that. That was the opportunity at the time, and the way we— the reason we brought on capital, and the re— and the way VC-funded businesses work is that we should be hiring ahead of our revenue curve 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, but ultimately, obviously you can't help but blame yourself and you can't help but, and you know, and it is really important to like sit and reflect and understand what were the decisions that that led to this point and how do we make sure we learn from it? And so absolutely it was on me, it was on our team in terms of those decisions. So super disappointing. But yeah, it was a rough week.
Yeah.
That's for sure.
I can totally imagine. And thank you for sharing all that. It's, you know, 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 reflector and you're a learner. And I'm curious, because you as a founder, as a 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, I just throw myself into situations and make sure I'm learning from them and I gather. And so the best way for me to synthesize that I've found is to get an exec coach so that I can real-time—
I support that. Yay, executive coaches.
Absolutely. Number one, get an exec coach. And mine's incredible. And like I can talk through these thoughts and feelings and learnings or vent or be frustrated or be happy and just like really pull out the learnings from that and apply frameworks to it. I think I never went to university. I didn't think in frameworks. And so like when I'm going through something and then being able to apply that kind of framework of thinking to it, it's definitely really helpful for me to synthesize that learning and take notes about it. I love to read books, but I don't read books enough, uh, and I'm not an extremely quick reader, uh, so if I need to learn something rapidly, I generally won't turn to a book. If I need to learn something more macro, just overall, I'll turn to a book about it. Um, and when— and the way I read books is I read it and I listen to the audiobook at the same time, which I found Helps me retain, like I can read way faster 'cause I'll 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. If I'm trying to just enjoy like a fiction book, I will take a much more relaxed approach. And then podcasts, I absolutely love podcasts. Again, being able to speed it up, but mostly around product, like Lenny's podcast. Lenny, uh, or VC20. Yeah, just around finding a very specific topic and learning from people, uh, that have done it before me. Generally, I'll find— I'll learn that a lot quicker. And then advisory, you know, I think building a mentor network, uh, and building an advisory. And that's why I specifically chose our angels and our investors, uh, so I can, you know, pick up the phone and ask them and talk to them. And why, like, we met at a conference why I find conferences valuable. They take up a bunch of time, but the network, you know, to be able to go meet amazing founders and CEOs that I can build a network with, actually build a proper relationship with such that I can text them or pick up the phone. It's not like this transactional Zoom conversation. And it's important for me, again, being in Australia, like I think when you're in a city where lots of those people are around, you can go have lunches and dinners and build that relationship. Doesn't happen a huge amount here. It's very end up being these very transactional Zoom conversations. And so really going and being very deliberate and intentional about building those relationships so that, you know, I've got a mix of CEOs and founders that are on the same part of the journey as me, that we're learning together and we can call each other and, and consult, console each other, or, or people that are a step ahead of me. And then the final thing I'd say is mentoring others. And so I've, you know, I do some angel investing. I started an angel syndicate and a small fund here in Australia, mainly so that I can access new founders and be able to, be able to, you know, give back to the community, but also advise and mentor, mostly because I just find it's one of the best ways for me to synthesize my learnings. I just find that I actually go into it like thinking I know nothing about this topic that they want to talk about, but I end up having a lot to say. And it makes me like really gather all my thoughts around it and actually end up leaving those meetings having learned something that I already knew, but been able to like categorize and be able to go take a more clear note about it. So that's been fascinating.
Yeah, that is fascinating. When you explain it to somebody else, you suddenly do realize like 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. It's 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 tactical and hands on the wheel. I think I kind of just like swung for the fences, just always had 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 it till you make it, but there's so much of like just figuring it out. Little story, when we started the agency, I went into a festival and convince them I knew what I was doing with digital marketing. They gave us half a million dollars to spend on media and it was the first time I'd signed up to AdWords. I'd never used it before in my life and we tripled their conversion rate. Like it was just, it was just, I spent basically good all-nighters for a week and just figured it out. And I think doing that a bunch of times means you kind of lose that imposter syndrome. You kind of just know that you can do it. And if you, and I think that in, in that zone of uncomfort is actually where I learn the most, and so I live comfortably there. More recently, I feel it a lot more as I've surrounded myself with people with significantly more experience in particular areas, uh, and so then when it's less about figuring it out for yourself and more about explaining to others your thoughts and what you think, or giving them the space to do it, yeah, that's when you can I 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 with it, you know, build that relationship with my team where I just really name whether I don't know something well and this is why I need you around it, or I'm going to go learn it, or, hey, we just can figure this out together. Or because then that way, that that gives you the space then for when you do know something, you can really drive in on and say, hey, I'm experienced here, and we can lean in on that experience more. Outside of that, you know, if I'm not naming, it's really just being comfortable with the process, knowing that actually this is the way I've learned a million times before. And I'll look back at this moment in 6 months and realize that that's actually the easiest thing I've ever done, and whatever I'm doing within 6 months is gonna be way harder. And so that's fine. One call out on imposter syndrome. There's a really great TED Talk from Mike Cannon-Brookes on imposter syndrome. Yeah, it's just like a very Australian approach to imposter syndrome, but it's super entertaining. But I think for someone like him—
And he's the founder of—
Atlassian.
Atlassian, sorry. Atlassian. Yes, I saw that TED Talk. It's fantastic. Everyone should watch it.
Yeah, it's great. I think watching things like that where you realize that actually even someone like him feels like he has no idea what he's doing each day, that's completely normal and fine and absolutely exactly where you should be. No one, especially founders in a high-scale group, like if you feel like you know what you're doing each day, then 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 that probably this, probably the scale that Linktree would get to, uh, that might have been better to start that journey earlier rather than waiting 4 years and running the agency and Linktree as a side hustle. Um, 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 of the way we built Linktree as a side hustle and through sheer kind of grit and determination and bootstrapping it actually kind of led to the style of product it is and the patience to grow with our users, learn from our users. If we were just all in on Linktree, I think we would've made different decisions 'cause we would've had to drive revenue in a different way. We would've had to push users into a higher plan earlier, these kinds of things. And I think, yeah, so even those kinds of things where like, yes, it would've been great to know about this and do it earlier, I actually don't know if it'd 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 executives and build a team and being able to, you know, do that from the outset and like just how to, yeah, how to construct the team. I think you end up, we've had all our trials and tribulations over the last 2 years of hiring great people and hiring not so great people and the impact that that makes on a business. And so I've taken 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. There's going to be plenty of people that tell you not only like, not that you're necessarily that you're wrong or it's a bad 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 really spending the whole, the rest of the time wishing you did it your way. Get an exec coach. That's definitely a good one. If as soon as you can afford it, find mentors. I think a really big one I've learned this year as well is nothing is ever as good or as 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 zoom out, it can be, be really, you know, things can seem dire. There's always a way out of it. And then, you know, like I said, 6 months later, it's going to seem like a blip. And also when things are amazing, it'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, uh, and articulate that. It's something that I have not nailed at all because our vision is so vast, and it's something that's 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 to understand it, and make— 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 really gonna get a lot out of this. So thank you so much for your time.
Awesome, Lisa. Thanks so much for having me. It's been fun.
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, alisacohn.com.
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