The Exchanges

Q terms of, like, determining where to spend and prioritize your time and where to focus. I'm intrigued. How do you think about resource allocation today? I always think the best CEOs are fundamentally the best resource allocators. How do you think about prioritizing and focusing resources today, and what drives those decisions? You expanded into the UK very recently, very quickly. What drives the prioritization decisions that you do take?

A Yeah, I mean, it is the fundamental question of an early stage or even mid-stage startup, which is, like, You can waste your time on so many things, and I think the way I look at it is what is unique about us? What are the unique characteristics of our company where we can absolutely differentiate, whether it be a user experience, whether it be market expansion? So if I take the example of the UK, we really felt, hey, one of our biggest advantages as a company is how quickly we move and how well we're capitalized. And so we said, there was a board meeting in March of last year or something, maybe it was late February, and we said, let's do it. And a 119 days later, we had 55 full-time employees in the UK, and we were launching. And so we set out to do something. We went over to the UK and hired 55 of the best journalists, editors in the country, and moved with unbelievable speed and focus because we had already hired so many people in the US. We knew exactly what we were looking for. And so, those advantages, they seem small on paper, but here we are a year later, and we're well north of a 100,000 paying subscribers in the UK, building a really great product for fans all over the world. And that's an example of us saying, hey, this is one of our biggest advantages, knowing that we can move quickly and have all this capital. Let's go and compete with companies that are over 200 …

AI assessment note: “what are the unique characteristics of our company where we can absolutely differentiate”

Q Can I ask, because it requires this, like, inflection point of yes from someone, that first big check, that first big seed. Can you remember that moment when you got the first lead seed who was like, yeah, I see this ten billion dollar company. Here's the whatever lead check for the seed round. Can you remember that moment, and what was it?

A Yeah, I can. I mean, Michael Horvath, the founder of Strava, was our first check, but it was a smaller check, and then the next check was Charles Hudson at Precursor, and Charles is amazing. And he went through a completely different process than anyone we talked to at that stage. And he learned about us as people, as opposed to the idea, the idea was still very, very, very small and unproven. And so he did his research on my co-founder, Adam and I, and that was really cool. And I'll never forget when he said, yes, any entrepreneur will say this, but like, it really gives you wings. You start to believe in yourself. There's so many moments early on. Where you don't necessarily believe in yourself sometimes because you've gotten so many no's in a row. And then even one yes can carry a thousand no's. And that was just such an amazing moment.

AI assessment note: “I'll never forget when he said, yes, any entrepreneur will say this”

Q terms of, like, determining where to spend and prioritize your time and where to focus. I'm intrigued. How do you think about resource allocation today? I always think the best CEOs are fundamentally the best resource allocators. How do you think about prioritizing and focusing resources today, and what drives those decisions? You expanded into the UK very recently, very quickly. What drives the prioritization decisions that you do take?

A Yeah, I mean, it is the fundamental question of an early stage or even mid-stage startup, which is, like, You can waste your time on so many things, and I think the way I look at it is what is unique about us? What are the unique characteristics of our company where we can absolutely differentiate, whether it be a user experience, whether it be market expansion? So if I take the example of the UK, we really felt, hey, one of our biggest advantages as a company is how quickly we move and how well we're capitalized. And so we said, there was a board meeting in March of last year or something, maybe it was late February, and we said, let's do it. And a 119 days later, we had 55 full-time employees in the UK, and we were launching. And so we set out to do something. We went over to the UK and hired 55 of the best journalists, editors in the country, and moved with unbelievable speed and focus because we had already hired so many people in the US. We knew exactly what we were looking for. And so, those advantages, they seem small on paper, but here we are a year later, and we're well north of a 100,000 paying subscribers in the UK, building a really great product for fans all over the world. And that's an example of us saying, hey, this is one of our biggest advantages, knowing that we can move quickly and have all this capital. Let's go and compete with companies that are over 200 …

AI assessment note: “the way I look at it is what is unique about us?”

Q Can I ask, because it requires this, like, inflection point of yes from someone, that first big check, that first big seed. Can you remember that moment when you got the first lead seed who was like, yeah, I see this ten billion dollar company. Here's the whatever lead check for the seed round. Can you remember that moment, and what was it?

A Yeah, I can. I mean, Michael Horvath, the founder of Strava, was our first check, but it was a smaller check, and then the next check was Charles Hudson at Precursor, and Charles is amazing. And he went through a completely different process than anyone we talked to at that stage. And he learned about us as people, as opposed to the idea, the idea was still very, very, very small and unproven. And so he did his research on my co-founder, Adam and I, and that was really cool. And I'll never forget when he said, yes, any entrepreneur will say this, but like, it really gives you wings. You start to believe in yourself. There's so many moments early on. Where you don't necessarily believe in yourself sometimes because you've gotten so many no's in a row. And then even one yes can carry a thousand no's. And that was just such an amazing moment.

AI assessment note: “I'll never forget when he said, yes, any entrepreneur will say this, but like, it really gives you wings.”

Q many a single consumer can have. And I asked this of Chris on the show with Substack, how many substacks will someone have? You won't pay for 25 substacks. And the question to you is like, Is Substack competitive to you in terms of, I love this writer who's just left the Daily Telegraph sports section, and I'm paying for him over the Athletic? Is it competitive? I don't know.

A I don't think so. I mean, you know, if you look at a single writer at a single moment in time, perhaps, you know, on the margins, but we're building a massive bundle for a very specific category. And we like where that stacks up versus a single writer on Substack. And I think if you look at what happened with Substack, to just take a second to look at that business, and it's a wonderful product, a wonderful founding team, and they're much more competitive with, say, Medium. And we don't necessarily look at them as competitors. They're probably capturing the opportunity that Medium had and missed. And we look at Substack and say, hey, if there is a great writer that left the Telegraph and is writing on Substack and they get to a certain scale, then heck, we're going to reach out and try to get them on our platform. And They may not join. They may say, hey, I really want to be on my own, and I like that, but we have an art department. We have a legal department, so you can do deeper journalism, right? We have editors that can guide your stories into better places. We can give a writer the ability to not have to write every day to really drive that subscription value, and for many folks, the economics work better under The Athletic than they might on Substack. Now, For others, it might be the complete opposite. So I don't see it as a competitive force at all.

AI assessment note: “I don't think so. I mean, you know, if you look at a single writer”

Q at all. I've been excited for this one, I have to say, but I'm also the biggest fanboy of both Strava and The Athletic, so I'm going to pretend like this isn't a fanboy moment for me, but tell me, how did you make your way into the world of startups and tech, and how did you really found the game changer for sports news and media with The Athletic?

A Yeah, for me, I started as an engineer early on in my career, and kind of actually all goes back to the Palm Pilot. I was pre-med in college. I forget what class I was in, and a gentleman came into our classroom, and I went to Penn State, and he came into the classroom and said, hey, everyone, I'm launching a new program at Penn State called IST, and if you try some of our classes, we'll give you this thing called a Palm Pilot, and you can write computer programs for it. And I remember in high school writing some simple programs for my TI-eighty-five calculator. And I was like, oh, that's cool. I'll check it out. And I just felt at home in that world. And I became an engineer through that experience and loved it. And as my career went on, I got into design and worked at Xfinity TV, building out a lot of the underlying tech and user experience around things like HBO Go and stuff. And I was just so passionate about building stuff for consumers. Never really enjoyed building stuff, enterprise, and I moved out to the West Coast and joined Strava. I was an avid cyclist, like, just loved it. I loved California. I loved just getting on my bike and riding, and Strava felt like such a natural place to work, and I was lucky enough to be employee number seven there, the first sort of design and product hire, and built out those teams over the years at Strava, and helped grow that company …

AI assessment note: “I started as an engineer early on in my career, and kind of actually all goes back”

Q I have to say, Alex, I didn't know it was 55 in terms of the talent acquisition in the UK. I have to ask, what's the biggest challenge about, like, scaling to 55 people in the UK when you're based in the US in a 119 days? Is it the actual, like, discovery and acquisition? Is it the culture maintenance? What's the biggest challenge of scaling up so fast?

A Well, I think the challenges are almost always different as you go into different countries, and I think in the UK we went in thinking folks would be more conservative in how they think. That was totally incorrect. We were worried about costs. We were right around where we thought it would be, so that was incorrect. Where we learned there were problems were things like garden leave, right? Folks have, like, things in their contracts that are very specific to the UK, so we had to wait a while for a lot of people, but overall, the challenge mostly was just flying back and forth. I had had a child for four months prior, and just back and forth, back and forth. It was grueling, but absolutely worth it and a blast.

AI assessment note: “overall, the challenge mostly was just flying back and forth”

Q No, I, I totally agree in terms of that authenticity. In terms of the communications, I spoke to John Adamassia before, and he said being a successful entrepreneur requires vision that sometimes borders on stubbornness, and yet being open to feedback and continuous improvement. And so he asked, can you think of a time maybe when you made a mistake and the steps that you took to rectify it?

A Yeah, I mean, this one is pretty easy. Early on in the company's history, I did a wide-ranging interview with the New York Times, and we were young. I think we had Five or six people at our headquarters, maybe 20 people on our newsroom, so quite small, and I said some things that blew up on Twitter, made me the sort of center of attention in a negative way, and it all came from a place of perhaps a little too much confidence, and I think as a founder, there's this crazy moment where you go from just a person writing code, convincing investors to Give you money. To being of interest to the world, and it's a little bit like a high school athlete getting on ESPN for the first time, and they stumble with their words, and they don't know exactly how to think about what they need to say, and here I was pitching and being really confident. There's this crazy aspect to how you have to convince people that you see this massive vision, and it's a situation where then you go to the press, and some of that confidence Bubbles out, and it's not really something that plays well in this modern media environment, and it was a massive lesson for me, and I told the company recently about this, and I was sobbing every night for a week, thinking I really damaged the company that we were building, that I embarrassed the people who I had hired, and I felt so terrible about that, and I said, I'm just …

AI assessment note: “I did a wide-ranging interview with the New York Times, and we were young.”

Q I have to say, Alex, I didn't know it was 55 in terms of the talent acquisition in the UK. I have to ask, what's the biggest challenge about, like, scaling to 55 people in the UK when you're based in the US in a 119 days? Is it the actual, like, discovery and acquisition? Is it the culture maintenance? What's the biggest challenge of scaling up so fast?

A Well, I think the challenges are almost always different as you go into different countries, and I think in the UK we went in thinking folks would be more conservative in how they think. That was totally incorrect. We were worried about costs. We were right around where we thought it would be, so that was incorrect. Where we learned there were problems were things like garden leave, right? Folks have, like, things in their contracts that are very specific to the UK, so we had to wait a while for a lot of people, but overall, the challenge mostly was just flying back and forth. I had had a child for four months prior, and just back and forth, back and forth. It was grueling, but absolutely worth it and a blast.

AI assessment note: “overall, the challenge mostly was just flying back and forth.”

Q No, I, I totally agree in terms of that authenticity. In terms of the communications, I spoke to John Adamassia before, and he said being a successful entrepreneur requires vision that sometimes borders on stubbornness, and yet being open to feedback and continuous improvement. And so he asked, can you think of a time maybe when you made a mistake and the steps that you took to rectify it?

A Yeah, I mean, this one is pretty easy. Early on in the company's history, I did a wide-ranging interview with the New York Times, and we were young. I think we had Five or six people at our headquarters, maybe 20 people on our newsroom, so quite small, and I said some things that blew up on Twitter, made me the sort of center of attention in a negative way, and it all came from a place of perhaps a little too much confidence, and I think as a founder, there's this crazy moment where you go from just a person writing code, convincing investors to Give you money. To being of interest to the world, and it's a little bit like a high school athlete getting on ESPN for the first time, and they stumble with their words, and they don't know exactly how to think about what they need to say, and here I was pitching and being really confident. There's this crazy aspect to how you have to convince people that you see this massive vision, and it's a situation where then you go to the press, and some of that confidence Bubbles out, and it's not really something that plays well in this modern media environment, and it was a massive lesson for me, and I told the company recently about this, and I was sobbing every night for a week, thinking I really damaged the company that we were building, that I embarrassed the people who I had hired, and I felt so terrible about that, and I said, I'm just …

AI assessment note: “learn how to interact With the press in a meaningful way, and I would just give”

Q to hear. And I didn't actually know he was the first in the lead for that. So that's awesome. Another one of your investors is Founders Fund. And they have a different view in terms of investor value add. And they take the view that investors can Can't really add much value to their portfolio. I'm interested. How do you feel about this? And what do you think about that?

A Yeah, I mean, I would say that, like, I look at them subtly different than that categorization. I would say, like, they believe mostly that founders can drive biggest returns because they have the biggest ideas, and that the more investors meddle, they tend to destruct value rather than create. And what's Amazing about Founders Fund is they believe in you as a founder, and they trust you as a founder, but that doesn't mean they just disappear. They hold you accountable. They have an incredibly high bar, and they're all so different and smart, and it's a situation where when you want them, they tend to be some of the best folks to talk to when you need advice, but they're not necessarily just lobbying it to you every time you talk.

AI assessment note: “I look at them subtly different than that categorization.”

Q to maintain that quality and standard. So totally with you on the love of the business model there. You mentioned Strava, though, and I spoke to, obviously, Michael, the founder, before the show, and he asked a specific question. He said, what are some things that you had to learn or even unlearn as the founder and CEO of The Athletic, really kind of from your time learned with Strava?

A My time at Strava was so... So good. I look back at that with such fond memories of learning how to build a subscription business. And one thing that comes to mind for me is focus. There is a little bit of a curse when you're so passionate about what you're working on in that you see every idea as worthy of deep exploration for your team. And so there were definitely a few years there at Strava where we were running around trying to build so many things at once. Whether it be nutrition or finding a route to ride or things like that. What I came back to as we got better in the company was focusing as many people in the company on a shorter list of things that have an objective as opposed to like, oh, that would be cool. That would be cool. That would be cool. Kind of like a dog, you know, squirrel, squirrel, squirrel. So that to me is a big one. And the second one that I might add on is this idea of inclusivity versus exclusivity. And If there are any cyclists listening, cycling can be a very exclusive sport, and it's probably one of the downsides of the sport. It's very complicated. It's a dangerous sport, and there's a culture around it, and it can make people feel like they're on the outside if they're not as dialed in to all the little tricks or culture aspects. And at some moments in the company's history, we were probably a little too exclusive. We should have talked to mo…

AI assessment note: “one thing that comes to mind for me is focus”

Q went out for many, many more releases, but there's always, there's always an issue in a post-COVID world. I'm really interested, though, because that's a big evolution in the business itself. I'm a very person-driven guy. I want to focus a little bit on your leadership style. When you think about the evolutions of the business, how have you seen your personal leadership style change over the last few years?

A Yeah, I mean, I've been the CEO for four and a half years, and the major thing I can say is the job changes instantly. Every single month, every hour, some days. What made sense at 10 people, it makes absolutely no sense now. And I think the thing that I really focus on now is just looking at it as a craft like anything else and really being committed to being great at it. And that means reading, learning, talking to the people on the team, talking to other CEOs, talking to investors, learning as much as I can. And the biggest shift now Going from zero to 550 employees is used to write code, and thankfully they don't let me anymore, but now my job is communication, and all day long I must focus on communicating, and that is absolutely a full-time job. Sometimes it doesn't feel like it, but building out the channels of communication in your company, making sure everyone feels focused, everyone feels energized, everyone feels Just like, we're building something meaningful, durable, you know, all those things. That's the job, and every bone in my body wants to get back and write code, and I'm pretty antisocial generally, and like, my job is communicating, and making sure of all those things happen, and that is an insane challenge.

AI assessment note: “now my job is communication, and all day long I must focus on communicating”

Q of 18 months ago, and now I've got like four, and I just want to be the best board member that I can be, quite frankly. My question to you is like, help me out here. What can I do to be the best board member, and what can I do to build that relationship with you, the founder, to be the best and the one you really go to?

A Yeah, so I'm a big listener of your pod, and so I'll try not to repeat a lot of the things I hear from folks on this one, and the thing that I would add to the dialogue is just care. You know, if you're on a board, you're smart enough, you've seen enough, you can recognize patterns quickly. Those are all, like, baseline attributes of a board member. Yes, you'll get some folks with lots more experience, but I think one of the most valuable things on a personal level is you can tell so quickly when the board member cares about the company, About you as a founder, about the journey, and the difference between someone who cares and someone who doesn't is so meaningful to the founder, because this is our life, right? This is everything to us, and when you care, you tend to be honest when you need to, but always have a little spoonful of sugar, and the incentives just all start to make sense when you both care, so that's what I would add.

AI assessment note: “the thing that I would add to the dialogue is just care”

Q many a single consumer can have. And I asked this of Chris on the show with Substack, how many substacks will someone have? You won't pay for 25 substacks. And the question to you is like, Is Substack competitive to you in terms of, I love this writer who's just left the Daily Telegraph sports section, and I'm paying for him over the Athletic? Is it competitive? I don't know.

A I don't think so. I mean, you know, if you look at a single writer at a single moment in time, perhaps, you know, on the margins, but we're building a massive bundle for a very specific category. And we like where that stacks up versus a single writer on Substack. And I think if you look at what happened with Substack, to just take a second to look at that business, and it's a wonderful product, a wonderful founding team, and they're much more competitive with, say, Medium. And we don't necessarily look at them as competitors. They're probably capturing the opportunity that Medium had and missed. And we look at Substack and say, hey, if there is a great writer that left the Telegraph and is writing on Substack and they get to a certain scale, then heck, we're going to reach out and try to get them on our platform. And They may not join. They may say, hey, I really want to be on my own, and I like that, but we have an art department. We have a legal department, so you can do deeper journalism, right? We have editors that can guide your stories into better places. We can give a writer the ability to not have to write every day to really drive that subscription value, and for many folks, the economics work better under The Athletic than they might on Substack. Now, For others, it might be the complete opposite. So I don't see it as a competitive force at all.

AI assessment note: “I don't think so. ... So I don't see it as a competitive force at all.”

Q to maintain that quality and standard. So totally with you on the love of the business model there. You mentioned Strava, though, and I spoke to, obviously, Michael, the founder, before the show, and he asked a specific question. He said, what are some things that you had to learn or even unlearn as the founder and CEO of The Athletic, really kind of from your time learned with Strava?

A My time at Strava was so... So good. I look back at that with such fond memories of learning how to build a subscription business. And one thing that comes to mind for me is focus. There is a little bit of a curse when you're so passionate about what you're working on in that you see every idea as worthy of deep exploration for your team. And so there were definitely a few years there at Strava where we were running around trying to build so many things at once. Whether it be nutrition or finding a route to ride or things like that. What I came back to as we got better in the company was focusing as many people in the company on a shorter list of things that have an objective as opposed to like, oh, that would be cool. That would be cool. That would be cool. Kind of like a dog, you know, squirrel, squirrel, squirrel. So that to me is a big one. And the second one that I might add on is this idea of inclusivity versus exclusivity. And If there are any cyclists listening, cycling can be a very exclusive sport, and it's probably one of the downsides of the sport. It's very complicated. It's a dangerous sport, and there's a culture around it, and it can make people feel like they're on the outside if they're not as dialed in to all the little tricks or culture aspects. And at some moments in the company's history, we were probably a little too exclusive. We should have talked to mo…

AI assessment note: “one thing that comes to mind for me is focus”

Q went out for many, many more releases, but there's always, there's always an issue in a post-COVID world. I'm really interested, though, because that's a big evolution in the business itself. I'm a very person-driven guy. I want to focus a little bit on your leadership style. When you think about the evolutions of the business, how have you seen your personal leadership style change over the last few years?

A Yeah, I mean, I've been the CEO for four and a half years, and the major thing I can say is the job changes instantly. Every single month, every hour, some days. What made sense at 10 people, it makes absolutely no sense now. And I think the thing that I really focus on now is just looking at it as a craft like anything else and really being committed to being great at it. And that means reading, learning, talking to the people on the team, talking to other CEOs, talking to investors, learning as much as I can. And the biggest shift now Going from zero to 550 employees is used to write code, and thankfully they don't let me anymore, but now my job is communication, and all day long I must focus on communicating, and that is absolutely a full-time job. Sometimes it doesn't feel like it, but building out the channels of communication in your company, making sure everyone feels focused, everyone feels energized, everyone feels Just like, we're building something meaningful, durable, you know, all those things. That's the job, and every bone in my body wants to get back and write code, and I'm pretty antisocial generally, and like, my job is communicating, and making sure of all those things happen, and that is an insane challenge.

AI assessment note: “used to write code, and thankfully they don't let me anymore, but now my job is communication”

Q of 18 months ago, and now I've got like four, and I just want to be the best board member that I can be, quite frankly. My question to you is like, help me out here. What can I do to be the best board member, and what can I do to build that relationship with you, the founder, to be the best and the one you really go to?

A Yeah, so I'm a big listener of your pod, and so I'll try not to repeat a lot of the things I hear from folks on this one, and the thing that I would add to the dialogue is just care. You know, if you're on a board, you're smart enough, you've seen enough, you can recognize patterns quickly. Those are all, like, baseline attributes of a board member. Yes, you'll get some folks with lots more experience, but I think one of the most valuable things on a personal level is you can tell so quickly when the board member cares about the company, About you as a founder, about the journey, and the difference between someone who cares and someone who doesn't is so meaningful to the founder, because this is our life, right? This is everything to us, and when you care, you tend to be honest when you need to, but always have a little spoonful of sugar, and the incentives just all start to make sense when you both care, so that's what I would add.

AI assessment note: “the thing that I would add to the dialogue is just care.”

Q to hear. And I didn't actually know he was the first in the lead for that. So that's awesome. Another one of your investors is Founders Fund. And they have a different view in terms of investor value add. And they take the view that investors can Can't really add much value to their portfolio. I'm interested. How do you feel about this? And what do you think about that?

A Yeah, I mean, I would say that, like, I look at them subtly different than that categorization. I would say, like, they believe mostly that founders can drive biggest returns because they have the biggest ideas, and that the more investors meddle, they tend to destruct value rather than create. And what's Amazing about Founders Fund is they believe in you as a founder, and they trust you as a founder, but that doesn't mean they just disappear. They hold you accountable. They have an incredibly high bar, and they're all so different and smart, and it's a situation where when you want them, they tend to be some of the best folks to talk to when you need advice, but they're not necessarily just lobbying it to you every time you talk.

AI assessment note: “I look at them subtly different than that categorization.”

Q Facebook and Google there, bluntly, I always question CACs, especially I get very nervous when it's so predominantly focused on Facebook. For you as a media subscription business, does it work from a unit economics perspective to have, like, customer acquisition strategies centrally focused around Facebook, or do you find actually bluntly the CACs are just too high now on these platforms, given just how kind of proliferated they are?

A We have had an incredible amount of success using platforms like Facebook, Instagram, Google to acquire users, and the cool thing that we're doing is And I think that this is where hopefully more companies will go, which is how do you use your content to grow your business? Well, mastering these platforms in terms of you controlling your destiny there is how to do it. And we pay these companies. We advertise. And the way we do it is we look at things like in the first 20 minutes of an article being out to the public, how's the conversion? How many people are clicking on the paywall? How many people are looking at our plans page? How many of our subscribers are scrolling down the article? How many subscribers are clicking the article in their feed? Right. All these little signals, they all add up to information that we can then use to say, well, this article is worth putting money behind. And then we can go put more money and we're starting to automate a lot of it. So within minutes of an article being out, we can learn, is it worth putting money behind? And then it's automatically posted to Facebook. And we learn in the first couple of hours, if it's working on Facebook, these are examples. And like, we have an entire team dedicated to this. And this is what I believe is like, what's necessary to survive. And grow in a world where Facebook, Google, other platforms own the custo…

AI assessment note: “We have had an incredible amount of success using platforms like Facebook”

Q at all. I've been excited for this one, I have to say, but I'm also the biggest fanboy of both Strava and The Athletic, so I'm going to pretend like this isn't a fanboy moment for me, but tell me, how did you make your way into the world of startups and tech, and how did you really found the game changer for sports news and media with The Athletic?

A Yeah, for me, I started as an engineer early on in my career, and kind of actually all goes back to the Palm Pilot. I was pre-med in college. I forget what class I was in, and a gentleman came into our classroom, and I went to Penn State, and he came into the classroom and said, hey, everyone, I'm launching a new program at Penn State called IST, and if you try some of our classes, we'll give you this thing called a Palm Pilot, and you can write computer programs for it. And I remember in high school writing some simple programs for my TI-eighty-five calculator. And I was like, oh, that's cool. I'll check it out. And I just felt at home in that world. And I became an engineer through that experience and loved it. And as my career went on, I got into design and worked at Xfinity TV, building out a lot of the underlying tech and user experience around things like HBO Go and stuff. And I was just so passionate about building stuff for consumers. Never really enjoyed building stuff, enterprise, and I moved out to the West Coast and joined Strava. I was an avid cyclist, like, just loved it. I loved California. I loved just getting on my bike and riding, and Strava felt like such a natural place to work, and I was lucky enough to be employee number seven there, the first sort of design and product hire, and built out those teams over the years at Strava, and helped grow that company …

AI assessment note: “I started as an engineer early on in my career, and kind of actually all”

Q Facebook and Google there, bluntly, I always question CACs, especially I get very nervous when it's so predominantly focused on Facebook. For you as a media subscription business, does it work from a unit economics perspective to have, like, customer acquisition strategies centrally focused around Facebook, or do you find actually bluntly the CACs are just too high now on these platforms, given just how kind of proliferated they are?

A We have had an incredible amount of success using platforms like Facebook, Instagram, Google to acquire users, and the cool thing that we're doing is And I think that this is where hopefully more companies will go, which is how do you use your content to grow your business? Well, mastering these platforms in terms of you controlling your destiny there is how to do it. And we pay these companies. We advertise. And the way we do it is we look at things like in the first 20 minutes of an article being out to the public, how's the conversion? How many people are clicking on the paywall? How many people are looking at our plans page? How many of our subscribers are scrolling down the article? How many subscribers are clicking the article in their feed? Right. All these little signals, they all add up to information that we can then use to say, well, this article is worth putting money behind. And then we can go put more money and we're starting to automate a lot of it. So within minutes of an article being out, we can learn, is it worth putting money behind? And then it's automatically posted to Facebook. And we learn in the first couple of hours, if it's working on Facebook, these are examples. And like, we have an entire team dedicated to this. And this is what I believe is like, what's necessary to survive. And grow in a world where Facebook, Google, other platforms own the custo…

AI assessment note: “frankly, the CAC has been very workable.”

Q Can you help me understand the margin element? Is that in terms of, like, analyzing cost of content creation and then, you know, subsequent, like, consumer acquisition on the back of that piece? How do you think about margin on a granular basis? I'm really interested.

A Yeah, I mean, if you think about when you build a platform, and I'll use Substack as the example, Substack takes a cut of the revenue and From the folks using their platform, and I think Apple has proven that model to be very, very lucrative if you can get scale, and you're taking a cut, but you need scale to build a venture scale business. Incredible scale, frankly. On our side, we own the entire experience, and so we're capturing a lot more of the value of our smaller category. We don't cover everything, we just do sports, but we own every penny from the customer, and so To us, it's like about margin from the customer, as opposed to building out a much bigger platform that is cutting or skimming a part of that revenue.

AI assessment note: “we own every penny from the customer, and so To us, it's like about margin”

Q Can you help me understand the margin element? Is that in terms of, like, analyzing cost of content creation and then, you know, subsequent, like, consumer acquisition on the back of that piece? How do you think about margin on a granular basis? I'm really interested.

A Yeah, I mean, if you think about when you build a platform, and I'll use Substack as the example, Substack takes a cut of the revenue and From the folks using their platform, and I think Apple has proven that model to be very, very lucrative if you can get scale, and you're taking a cut, but you need scale to build a venture scale business. Incredible scale, frankly. On our side, we own the entire experience, and so we're capturing a lot more of the value of our smaller category. We don't cover everything, we just do sports, but we own every penny from the customer, and so To us, it's like about margin from the customer, as opposed to building out a much bigger platform that is cutting or skimming a part of that revenue.

AI assessment note: “we own every penny from the customer, and so To us, it's like about margin”

Q With the centrality of communications, I'm really intrigued. When you look back over the scaling of the business, what's worked in terms of those communications, and what hasn't?

A I look at this and say, I have to be myself. And so the way I communicate is passionately, honestly, transparently, sometimes to a fault, directly, sometimes to a fault. So all these things, I think it has to be natural. If you're faking it, if you're trying to be someone you're not, it's just not going to work. And so all those aspects, and my co-founder Adam, you know, we share a lot of these aspects, which is wonderful, in that We are really, really transparent with our staff. We keep them up to date. When the pandemic hit, for example, every other week, we're doing deep all hands where we're showing them the metrics of the business right away, giving them insight. And folks in journalism have never been given this access. And we're just including them in for the ride so they understand how we're thinking, why we're doing X, Y, or Z. And those are just some of the things that have really helped me just be me.

AI assessment note: “We are really, really transparent with our staff. We keep them up to date.”

Q With the centrality of communications, I'm really intrigued. When you look back over the scaling of the business, what's worked in terms of those communications, and what hasn't?

A I look at this and say, I have to be myself. And so the way I communicate is passionately, honestly, transparently, sometimes to a fault, directly, sometimes to a fault. So all these things, I think it has to be natural. If you're faking it, if you're trying to be someone you're not, it's just not going to work. And so all those aspects, and my co-founder Adam, you know, we share a lot of these aspects, which is wonderful, in that We are really, really transparent with our staff. We keep them up to date. When the pandemic hit, for example, every other week, we're doing deep all hands where we're showing them the metrics of the business right away, giving them insight. And folks in journalism have never been given this access. And we're just including them in for the ride so they understand how we're thinking, why we're doing X, Y, or Z. And those are just some of the things that have really helped me just be me.

AI assessment note: “every other week, we're doing deep all hands where we're showing them the metrics”