Transcript

[Harry] TJ, I am so excited for this. As I said, I feel like I know so much of the PillPack journey from the wonderful Fred Destin, so thank you so much for joining me today first.

[TJ] I am thrilled to be here. This is the first public thing I've done in five years. And obviously I owe a ton to Fred as well. He bet on both of us when we were super young, so thrilled to be here.

[Harry] I am so grateful that this is the first thing you've done in five years, but I want to go to PillPack in that kind of founding aha moment. Obviously we see the incredible journey today and we see the exit, but in terms of that founding moment, what was that aha founding moment for you? Take me there.

[TJ] Yeah, so I think if you go way back, like I grew up in New Hampshire in a family that owned and operated a classic mom and pop pharmacy, so I grew up in and around pharmacy. And I'd worked a ton of different jobs at my dad's pharmacies, worked behind the counter, helped check people out, actually was delivering meds to people in their homes and saw that experience. I just knew there was a lot of opportunities to make it better. It was super frustrating. It was really complicated. So I was in pharmacy school in Boston doing the classic, going down weird rabbit holes in the internet as a college student and buying and selling sneakers, got really obsessed with design, thinking about furniture and architecture, and I was just very interested in kind of aesthetic. And then very separately, got really interested in startups, snuck into MIT and they were super gracious. I didn't go to school there, but helped for the MIT 100K, which was like their business plan competition at the time. When I showed up for the sort of first meeting with all the students and they're like, you don't go to school here. And I was like, nope. And they're like, we're not paying you. So if you want to do some free work, I guess that's fine. And then I actually started this thing called hacking medicine at MIT with Elliot, my co-founder, which was getting just doctors and designers and physicians all together to work on stuff in health care. And through that period, 2005 to 2010, my dad started this totally new pharmacy that was sorting and packaging meds actually very similar to pill pack, but they were selling into nursing homes and assisted living facilities. It wasn't a consumer business. And so I always had this idea of could you take this kind of core product, but then offer it to consumers and do it in a way that was really designed forward and aesthetic. I think for me, the big challenge is getting the confidence to think I could actually go do that. Could I actually raise venture capital? Could I find a real co-founder? Like getting the inertia to believe that I could do that.

[Harry] Why did you not have the confidence and what gave you that confidence in the end?

[TJ] Yeah, I'm a little bit more of a non-traditional founder, right? I didn't go to an elite school. I didn't have the sort of normal connections that a number of founders do. At least that was my perception. That's probably not a hundred percent correct, but it was a wacky background, right? I'm a pharmacist. I'm not like a normal entrepreneur in that context. And in hindsight, I think it was my perception and the actual reality, but that was the hurdle for me. I think once I made that jump from there, it was very natural. It was more like a snowball rolling down a hill. I think it's a lot like if you've ever been skydiving, like jumping out of the plane is really scary. But like once you're in the air, it's actually pretty chill. And it was like that for sure for me. Yeah, I mentioned for the first time at Hacking Medicine, which is an event that we started. So it's wacky, but we won the event, which is very exciting. It gave me the confidence for better or worse. This is like the fall of 2012. I'd been a pharmacist for about six months or like fresh out of school. I think within a month or two, we were in, we got into Techstars, quit my job. It's kind of like January of 2013. But I think that it was for me, it just wasn't an aha moment. It was like, how do we combine like my expertise in pharmacy with my interest in design, with my interest in tech? It was like, how do we put all these things together? And it was a very kind of iterative, natural process in hindsight, right? Obviously, that wasn't intentional going into it. But it really was the combination of all these things I was doing and I was interested in that ultimately became PillPack.

[Harry] When we hear your background there and the parents' roots in pharmacy and having their pharmacy, your father kind of iterating on that model, it just seems inherently like this founder market fit. How important, I'm just intrigued, how important do you think founder market fit is given the lens that you come from and the experience that you have?

[TJ] Yeah, I think it's really important to understand the customer problem. I think it's less important in understanding like all of the nuance of the industry and dynamics and other things that are going on. But I do think if you don't deeply understand the customer problem, it's likely you'll build the wrong solution. That's where my expertise was unique. I don't think it was that I was a whiz kid on how pharmacy worked. I think it was that I'd spent enough time inside the pharmacy. I'd spent enough time in customers' homes that I did deeply understand that problem. And I looked at all the solutions that were out there and I felt like we could offer something that was a lot better.

[Harry] TJ, I think we're all, despite whatever we kind of project, I think we're all running from something and we're all the function of our histories. And so before we get into the journey and entrepreneurship, I do just want to touch on this, which is what do you think you're running from when you think about all being a functions of our past?

[TJ] I had this conversation with someone a couple of months ago that made the comment that kind of stuck with me that we're always probably looking for the opposite of the environment that we had as a kid to some degree. For me, my dad grew up with almost nothing and worked incredibly hard to become a pharmacist, to give us a childhood that was way better than his. But it was like a very kind of Leave it to Beaver childhood, right? Very predictable, very stable, just very classic. And I think I was always looking for a little more excitement, a little more risk in my life. And so I think startups were a great way for me to harness that, but led to me being very uncomfortable in very formulaic, stable environments.

[Harry] So I think one of the reasons the show is done very well, TJ, is because I have a schedule and I say fuck it. And I also just go with my heart. I listen to your predictability and stability there. And I'm very envious of children that have predictable parental guidance and predictable childhoods, that structure I didn't have. How do you think about your parenting today having had that predictability? And is that what you want to give them or not?

[TJ] I think for me, it's really about giving them an environment to be kids is probably the biggest thing. I don't know if it's as much about predictability versus non-predictability. But the thing that we're trying to provide for our kids is the ability to go explore, be kids, to be able to have independence and to grow independence early, which I did have in my childhood. We were the classic 80s, 90s kids that hopped on a bike and took off and came back before dinner. I'm trying to keep that because for me, that was a magic of childhood was being able to go build forts in the woods and be gone for the whole day. It wasn't like my schedule's packed and I want to actually provide that for my kids. And certainly, hopefully our environment is stable. For me, that's the thing I think about a lot is how do I retain a childhood that is for the most part now gone for a lot of kids?

[Harry] I have the most wonderful imagery from US films of jumping on a bike and going around picket fence ecosystems.

[TJ] That was definitely my childhood.

[Harry] I think great, but I want to move from the stability to uncertainty to instability. And you've said to me before, you have to get comfortable in an environment of uncertainty if you want to be a great entrepreneur. Why? And how did you get comfortable in uncertainty?

[TJ] I think a thing that I believe now that I did not believe during the early part of the PillPack journey, or honestly, probably into the last couple of years, is that there are folks that are on the extreme ends of this from a personality standpoint. I think there are folks that truly are much more comfortable in uncertainty than they are when things are certain. And I think there's obviously folks way on the other end of that spectrum. And obviously, a lot of folks are more in the middle. I'm super naturally comfortable in an uncertain environment. It's kind of my happy place. And so I think the advice I do have is being really honest with yourself about where on that spectrum you are as a human. Because I think if you like certainty and you like predictability and you like that lifestyle, you'll honestly probably be happier at a big company. And if you like uncertainty, you're going to be miserable at a big company. Maybe it might make sense to go do something that's a little riskier.

[Harry] Do you think most entrepreneurs today are uncomfortable with uncertainty? I'm giving a data point here. But from our portfolios, which are quite broad and diverse now, we've had six founding people from founding teams leave in the last month. I feel there's a real breaking of founder partnerships as times have got hard. Do you think founders are uncomfortable with uncertainty today?

[TJ] I think it's plausible that there are a number of founders that are in the role and might be more comfortable in a different type of role. In a broad perspective, mine is very narrow. But I have come to terms with the fact that I think it's very hard for the classic overachiever that sat in the front row in every class and always delivered papers on time and always got A's into every one of their classes. To go from that reality into a startup, which honestly rewards a very different type of behavior and a different type of tactics. And I think there are some folks that got swept up in sort of perceived glamour of being a founder rather than the reality of that job. And so I do think there is a big like founder fit in the gig. And I think being super honest with yourself about who you are and what you really enjoy and what environments make you happy is, I think, super important.

[Harry] I think terrible podcasts like this glamorize entrepreneurship and that if we showed the true brutality of it, no one would ever fucking do it ever. So that's not good for our business. But the other aspect that you said, as well as being comfortable with uncertainty, is that as CEO, you have to set the vision and get out of the way. I thought this was interesting. Can you expand on this and your biggest kind of lessons on doing this?

[TJ] Yeah, I think this would actually be way harder for me now. When I started at PillPack, I was 26 and I had no preconceived notion that I had any idea how to do the tactical jobs better than the folks I was bringing in to do them. There was no way I knew how to acquire customers better. There was no way I knew how to run operations better. There was no way I knew how to be a finance lead better than the people I was bringing in. The only technical training I had was in pharmacy, which had very little relevance to most of the things that a founder's doing. So honestly, there was a beauty in being young and not having experience in this context.

[Harry] How did you bring them in? You're young, you don't know their space better than them. How did you know what good looked like? Why do you think they joined a 26 year old, Mer fans, who didn't know what good looked like and only knew pharmacy?

[TJ] Yeah, I was able to focus on the things that I thought I had to be good at, which was things like raising money and setting the vision and everything external. And we did have a big vision. And it was a clear vision as far as understanding who was good and not good. A lot of it was intuition and trying to read people. And then it's plausible that I completely made the statistic up. But at one point, somebody told me that the difference between the worst and the best hiring managers was roughly like, if you're a terrible hiring manager, you're right like 40 percent of the time. And if you're an amazing hiring manager, like world class, you're right, like 65, maybe 70 percent of the time. And my takeaway from that was like, I better be really good at changing my mind if I'm wrong. And that's the only way to get to 90 plus percent is to hire someone that's not going to work out, be really quick at making that call and trying again. And I took that to heart and I definitely behaved that way as we built the team.

[Harry] How do you determine whether someone just needs more time? This is something I struggle with. I think a lot of founders struggle with. People can take a while to get used to new environments, new decision making structures. How do you determine between TJ enough's enough and hey, we should give them another two weeks?

[TJ] I was incredibly impatient is probably my biggest flaw is being pretty impatient. Once I was on that trajectory, I made the call like I didn't dilly dally around these things a whole lot. The only delaying was really because it's hard, right? But I was very decisive on this stuff. I think it came from the fact that I was just generally impatient as an operator.

[Harry] No, I totally get it. I think impatience is really important. And the trouble with Europe is we're very patient tomorrow. We'll get on to the execution.

[TJ] Americans are quite impatient folk.

[Harry] Oh my God. Nightmares. But what I want to ask is you mentioned like your naivety bluntly across many aspects of the business when he was starting. Naivety is often said to be a good thing, a bad thing by others. Is naivety good or not? And if so, why yes or why no?

[TJ] Yeah, I always say that I think Elliot and I were in the perfect place personally when we started PillPack and we got very lucky in that sense. I think we were absolutely not naive about the customer and about what the customer needed, what the customer wanted. Like we deeply understood that, but we were incredibly naive about the broader industry dynamics. We had no idea around incumbents and what they cared about and why all the things we wanted to do wouldn't actually work. And, you know, we looked at it and said, of course, we're going to make an awesome product. We're going to make this way better for customers and we're going to put it online and we're going to require customers online. This is going to be super straightforward. Then we were just woefully ignorant about all the reasons it wouldn't work from an incumbent and industry standpoint. And I honestly think that's the perfect balance. It's like you got to understand the customer, but if you understand all the reasons it's not going to work, you're never going to start the company. If I had been working in pharmacy for a decade as an adult, there's no way I would have started PillPack because there were very specific reasons it shouldn't have worked. And I think that's where the naivety is really powerful. If you don't understand the customer, you're hosed, so you can't be naive there. But I think important to not know all the reasons that the thing you're trying to do might not work.

[Harry] OK, when is naivety good and when is it bad? Because it can be bad.

[TJ] But again, I think it is about like the difference between not totally grokking industry dynamics and grokking the customer. We took money from exclusively consumer tech investors. We weren't out pitching healthcare investors. I think almost every healthcare investor would have said no because of the fact that the industry dynamics were the way they were. And so the investors were just as naive as us on a lot of the dynamics at play.

[Harry] Can I ask, when you got no's from, did you think that healthcare investors didn't get it and like they didn't see the future in the way that you did?

[TJ] No, it was probably a little different than that. I think I thought I didn't really need the help of healthcare investors. I think I thought I needed the help of consumer investors. And so it was augmenting the things I thought I understood. And it was less about whether they'd say yes or no for me. It was, when you look at the PillPack business, yes, it's a healthcare company. It's a pharmacy. We interact with payers. We do all the things that healthcare companies need to do. But I at least thought I knew how to do that. I'd been pretty involved in the space for a while. And the things I didn't know how to do were how to build a consumer brand, how to acquire customers, how to build world-class kind of consumer tech. And so it was more about augmentation and the people that I wanted to be pushing me on the board. And it was less about getting to a yes or no.

[Harry] Can I ask, you mentioned impatience earlier. As we said, impatience is important because it plays a role in how fast you move and your speed of execution. How important a role does speed of execution play, do you think?

[TJ] In this game, it's the only thing that matters, right? It's like, how fast can you figure stuff out? You think about the game that venture-funded founders are playing and they're taking money and they've got roughly 18 months to figure something out that's really critical to getting to the next round of financing.

[Harry] What can you do to increase your speed of execution?

[TJ] It goes back to hiring great people and mostly getting out of the way and giving them the autonomy to make decisions. I think it is also being really explicit about which decisions are things that can be changed and need to be made really quickly and which decisions can't be changed and are really high consequence. And I think if you find the right leaders and you build the right exec team, they'll mostly be able to parse those two things. If it's even cuspy on the bigger decisions, they'll be coming to you and you'll be working through it. But for everything else, like people should have the autonomy to go, like you should be hiring real doers that know how to execute and then they should feel like they have the autonomy to make the call and go as fast as possible.

[Harry] Can you start from a relationship of full trust?

[TJ] Yeah, it's funny you asked that. When we were acquired by Amazon, we took all of our internal, the equivalent of Amazon LPs, like leadership principles, right? And we tried to mash them up one to one with what's the equivalent like Amazon one. And they actually like almost all tracked sort of one to one, like customer obsession and all these things worked dead on. And the one that was the exact opposite was we had this leadership principle at PillPack, which was my favorite, which was assume the best. So almost all your best relationships in life are about assuming the best in someone, not assuming the worst. Right? And so if you start from that frame, like you'll get rid of 90% of conflict by assuming that people are trying to figure it out and everyone's doing their best. Amazon's equivalent was earned trust, which is literally like the opposite leadership principle. And I didn't actually think a whole lot of it. Like we just tried, we mapped them and go, yeah, the same earned trust, assume the best. In hindsight, that is like literally the opposite culture, right? It's assumed the worst until you've proven otherwise. We built a culture that assumed the best that people showed up, we made bets on people, and then we assumed that they were going to execute and that they, and we trusted them.

[Harry] Did you ever make a big fuck up because of assuming the best? I listened to that and I think that's naive. I don't mean it badly. I'm an earned trust.

[TJ] Yeah, never backfired on us in a meaningful way. Certainly there was a lot of goodness that came from it. So no is the short answer, but certainly could have been burned.

[Harry] Speaking of kind of the goodness that comes from it. Ultimately, you want to achieve rapid decision-making in terms of achieving that culture of rapid decision-making other than assuming the best from day one. What works well in creating a culture of rapid decision-making and what really messes it up?

[TJ] I think if you're making really critical, irreversible decisions rapidly, that will really fuck it up. Like I think you'll make a lot of really bad decisions. Honestly, like I took as long as like humanly possible to make those critical decisions. And honestly, to some extent, to the frustration of my exec team throughout the course of the business, but a lot of times, like in a very kind of mutually agreeable, productive way. Honestly, like the best articulation of this out of every one of my team was Elliot, who's my co-founder, who is amazing. And I'd say the bigger decisions that we made over the course of the business were a byproduct of going on two hour walks three times a week for six months. Like we were just batting these things back and forth for a very long time, sort of reticent to make the call. And I think that's super important too. It's like a bifurcation of decision-making. If you can change your mind, just make those decisions as fast as humanly possible. Honestly, don't even bring them to me. Just let go. And if you're wrong, we'll change your mind and we'll do it the other way. That's totally fine. But if it's something that's irreversible, we're going to, we're going to work this one out until you're so frustrated that you feel so confident that it's the right decision that we'll know it's the right decision. I think sometimes people make all the decisions in the median instead of bifurcating these things. And I think that's super critical.

[Harry] Can you take me to a decision where you decided, uh-huh, we need to go slow on this? I need to spend time on this. And the exec team and everyone around you was going, oh, TJ, what was the decision that sticks out when I asked that?

[TJ] We had a number of run-ins with incumbents around our access to their networks over the course of the business. And I think we knew this was going to be a problem back in probably like middle of 2014 or something like that. And Elliot and I would just wrestle with nonstop. Is there a way to get in front of this? Is there a way to like get meetings and try to work through this productively before it blows up in our face? We batted it around nonstop. And I think if you let your anxiety get the best of you, you would have made the call and just done something because you felt like you had to do something about it. And in reality, we just sat on it. We let it ride, but ended up becoming like the make or break moment in the company. And I think it was the only way that we could have possibly pulled off what we did pull off.

[Harry] What do you think is the single best decision you made with PillPack and what did you learn from it?

[TJ] I think that probably the more useful answer to your question is we made this, certainly at the time, a weird decision that we were only going to focus on the end customer. Like we, in healthcare, you've got payers, you've got providers, you've got other constituents, you've got the end customer. And honestly, it's the reason that most of healthcare is as fucked up as it is that almost no one is actually building for the customer that's that is using the service. And so we effectively put on blinders to everybody else. We said everything we're doing is to make this easier for the customer. And if we've got to do weird stuff to make that possible, that's totally fine. We'll do the weird stuff. And if like a provider or payer is upset about the way we're doing something, but it's better for the customer, sorry. Like we're, we're building the thing for the customer. We're not actually building it for you. And that ended up being both incredibly critical and it enabled us to build an amazing service. We never strayed from is that the only thing we care about as a business is building for that end customer.

[Harry] I totally agree with you in terms of the importance of that focus and also what it does for you in terms of product marketing and messaging, having that concentrated end profile. If we think about the flip side, what was the worst decision where you're like, Oh no, that we fucked up that one.

[TJ] I think one of the most difficult things as a founder is finding the balance between doing things that don't scale and having less experienced folks, just cranking away and figuring things out versus when it's time to bring in some adults and when it's time to bring in kind of real operators. And I think we messed up that balance and in bringing in a head of finance, bringing in a head of ops at the right time. And it was incredibly painful. We're a deeply operational business and we probably waited nine months to a year longer than we should have to bring in a real operator.

[Harry] Well, when you say a real operator, is that an exec team or is that a CFO? What do you mean by that? And what would you advise founders having had that experience and bad decision?

[TJ] Tactically, we started the business. We had a head of ops that I had known for a long time, but was young, hungry and knew the business super well. It was actually the first person I hired and he scaled that thing to four or 500 people, like zero humans to 500 people or something in operations and was more dedicated to the business and the customer than anyone I've probably ever met. I bet he slept in the pharmacy 40 days in one year and was just able to figure anything out. And that was amazing. That's like the perfect archetype of an early operational leader is that I deeply know the domain. They're happy places, not like going and building unnecessary processes. They're happy places. Let's just go figure this thing out. But at some point that approach breaks, right? At some point you just get too big. It doesn't work anymore. Like you have to have the right systems and the right process and all that stuff. And I think he was so good. Like we just went too far with that approach. It's a funny story, actually. Probably the worst board meeting we ever had was the board meeting before Yvonne joined. Everything was breaking, but at that board meeting it was like, Oh no, everything is like really breaking. But the problem was that we had hired Yvonne, but she hadn't started yet. So she came to the board meeting. And so it was this hilarious dance between the investors and me and Yvonne where everyone knew it was broken and the investors were pissed. But they didn't want to freak out Yvonne because if Yvonne didn't show up, like we were way more screwed. So it was just like this hilarious, like emotional dance of how do we say all the things we need to say in a way that like makes Yvonne excited to fix all these problems and not so scared that she runs away. But for sure, that was like the most operationally painful moment in the business.

[Harry] I love it when you have a multi-stage fund on the board early and you want them to do the next round. And so you're like, I know it looks bad, but I see this as an opportunity. Speaking of Yvonne and the timing there, when you think about exec teams, what should we front load first? Why? And how do you think about that?

[TJ] I always think about each round for a classic venture backed company is trying to be super crisp about the thing you're trying to prove on that round of financing, right? But what is the bet your investors are making? And do you have the right team to achieve like that single bet, right? Like you kind of have to put blinders on and be really thoughtful about what that is. So for us, we raised the first round of financing. Like it was taken on face value that like, I knew how to open a pharmacy. I knew roughly what the economics were because we were in a similar business before. I knew how to build a product ish because we had Elliot on the team and he had built products before. The flyer everyone was taking is, can you acquire consumers online for this company? And so the only thing that mattered post that first round of financing was can we actually acquire customers online for a pharmacy, which we jumped back till 2013. Like starting a pharmacy is not what starting a pharmacy is today, right? There's row and hymns and pill pack and capsule and true pill. Like there's all this great activity in pharmacy in 2013. There were not pharmacy startups, right? So that was a weird thing to begin with. And so I think that was the bet we were making is to come back to your question at that moment in time, it would have been weird for us to go hire, like a really killer CFO and like a really amazing head of ops. That would be like awesome to build that exec team. It was like, we can ignore that stuff actually. Let's go find the best folks to help us figure out customer acquisition. And I think you have this journey in any startup, right? So like you get customer acquisition working and then all of a sudden ops are imploding and now you got to go find a really killer operator. And I think you, to some extent have to be in reactive mode and less about we're going to go find like a amazing exec and they're going to build all this process and this function and be comfortable. Or this is the only thing I care about for right now. And we'll figure that stuff out later.

[Harry] I totally agree with you there. I think the hard thing is when it comes to selection, who do we decide to have on that team to help us? And you said before, I love this, be very selfish about who's on the exec team. What did you mean by be selfish about it and how do you advise founders on that?

[TJ] So I think it's less about being selfish in the sense of who you're recruiting. It's more be selfish who shows up in that weekly meeting that you spend three hours going through the business. Because a good rule of thumb is if you bring your head of HR and your head of legal and your head of finance and your head of ops. And if you bring every one of the leaders on the team into that room, you should take the three hours you have and divide it by the number of humans in that room and assume each one of them gets that amount of time to talk. And so do you really want to spend a seventh of your meetings talking about promotions and leveling and HR stuff? Being really thoughtful about who's in that room will determine what are you spending your time in that sort of most critical moment debating. So for us, and this honestly wasn't intentional, it was just it was a byproduct of who was on the team. But by the time we sold the company, we've got a thousand people, we're doing a few hundred million in top line. The entirety of that meeting was me, Yvonne, who was COO, CFO, legal HR, kind of all those functions, Elliot, who was product and tech, Jeff, who was BD and growth, and Colin, who was marketing and design. There was five of us in that meeting. And if you look at who the five were, like you're going to spend 85 to 90 percent of your time talking about product and growth. The combination of HR, legal, ops, like all the tertiary functions get 10 to 20 percent of the time in the meeting. It just made us focus on the things that are ultimately going to drive a startup's success. But a startup is about product and growth. That is the only thing that matters. And who on that team shows up I think determines what you're focused on as an entire organization.

[Harry] You mentioned the functional leads there and you tweeted before about kind of the difference between an org with kind of functional leadership versus an org with kind of GM leadership. For those that don't know, what's the difference between functional leadership or functional org versus GM org? What's the difference there first?

[TJ] Yeah, so functional org is roughly what I described, right? So if you look at the CEO and their exec team, each leader on that team is going to have a function. You have a head of engineering, you have a head of design, you have a head of product, you have a head of operations, a head of finance. It's very functional. It's like the most simplistic, straightforward org design. It's where most companies are going to start. A GM-focused org is where most big companies end up, right? So a GM-focused org is where you've got single-threaded leaders that in theory own a P&L, and under that leader they have a head of finance, a head of ops, a head of product, a head of tech. And so you end up having like hundreds of these GMs that manage a single P&L and have pockets of each of these functions inside of their business. Maybe somewhat controversially, I think the second you go to a GM-focused org, you're not a startup anymore. Like you are a big company. Almost all of the downsides of a big company that people bemoan, the amount of HR, the amount of overhead and decision-making, like the all the over-processed-ness, I think it's all a byproduct of that single decision. You could not have built a company like Amazon or another large company without doing that, but it has all sorts of negative repercussions. And I think if you're a startup, like you're so far on the other side of that extreme, that I think it's like more of an unnecessary intellectual exercise to think about going to GM than it is actually going to do any good for you. And you can build huge companies that are functional. Apple is like a functional org.

[Harry] Yeah, that's my question. I've interviewed functional leaders from Snap and LinkedIn in the last few days. These are big companies and public companies. How should founders determine whether they should run a functional versus a GM-led org? What's right for me?

[TJ] Yeah, I'm far on this extreme, but I think stick with functional until it's so obvious that it can't possibly work, that maybe there's an excuse to go to a GM-focused org. And certainly if they've got like a manageable number of product lines, I wouldn't even have the conversation. It's just not worth the debate. It is going to make your business worse and it might not do it right away, but it is definitely going to do it on the long term. Yeah. If you think about all the extra process that that creates, right? So if you have a GM-focused org, like you now have to do all this work to make sure that all of your eng 2s are leveled at the same level because one's in this team and one's in that team and then don't talk at all and they have no idea what the other team is doing. And so if they transfer from this team to that team, you have to make sure that they're both as competent and you have to make sure that everyone's compensation is identical across 15 different businesses for the same level. It is what creates like an enormous amount of HR work, an enormous amount of like overhead because you're trying to do all these weird backflips to make sure that there's consistency in the business instead of just having a whole org of engineers and a whole org of designers where that stuff just comes in kind.

[Harry] I also feel like you're creating this kind of dysfunctional decision making because you have CEOs on top of CEOs. Your GM who runs that segment isn't actually the ultimate decision maker. They can still get overridden by the CEO up top or the CPO who's ahead of them. And so you create this very strange chasm between power ultimately.

[TJ] And you just don't have your best people on every product, right? If you've got your head of product and your head of engine, your head of design working on every product, they're going to be better, just like de facto going to be better products.

[Harry] Man, you mentioned comp as one of the reasons it can be challenging. What are some of your biggest lessons on comp and equity and how it can be used most effectively by founders?

[TJ] I didn't appreciate this nearly as much as I probably should have at the time, but incentivizing your team as much as possible on equity ends up being like the biggest lever you have from a cultural standpoint. But if you take kind of pill pack pre acquisition versus pill pack as part of a big organization, pill pack pre acquisition, like I don't think I ever once had a conversation about leveling someone or promoting someone in a meaningful way that was going to dramatically change their comp. Like we bet on people, we gave them a big equity package the day they started and we expected them to deliver on that equity package. And so like everyone either won as a team or we lost as a team. There was no point in trying to go carve out some way for you as an individual on that team to win in a way that mattered. And so everything falls out of that. We're going to win or we're going to lose. We're all aligned. Like from an economic standpoint, you get to be a big enough company, even if it's technically equity and it's stock, it is rational to care far more about like your own career pathing and the next promotion and all of those things than it is to care about winning or losing. And so it is like the biggest lever a startup has culturally.

[Harry] You agree with that in a macro turn, though. And what I mean by that is like, bluntly, what I see now today in particular, people want cash. When times get tougher, they want the cash, equity not so much. I see that in Europe as well. Do you think that's fair?

[TJ] They should go work at a big company then. It's fine. That's not the game we're playing. Startups are about like pulling something off that's incredibly difficult and everyone doing incredibly well if you pull it off and that's not cash. So it's just a different game.

[Harry] Yeah. I want to dive into a couple of elements of the story, which I think are really important. As we said before, it's very easy to look at PillPack and think, oh, all up and to the right, billion dollar sale. Life is good. There's always early hiccups. What were the single biggest early hiccups you really remember and stick out to you?

[TJ] Yeah, I talked a little bit about that sort of first bet, right? We started the company, we raised about four million dollars between two quick rounds right out of the gate. And the bet people were making is that we can acquire customers. Everyone assumed we'll start a pharmacy. They assume we'll get in network with payers. Like all that stuff was a given. So if you jump forward, we started the company in 2013. We raised that round middle of 2013 and we launched the product in early 2014. And for folks that were around at that time, the way you acquired customers was buying Facebook ads, like point blank. But that's how every DTC company was scaling. But so we assumed like we're going to do the same thing. We're going to buy Facebook ads and like hopefully the economics work and hopefully we can acquire customers in this category. And we launched, we got our ads turned on and they were working, right? Like we were acquiring customers at a number that was lower than we promised. And we're like, oh my God, it's working. This is great. And out of nowhere, our account got shut off. We got suspended from Facebook ads and we're like, uh, this is not good. Uh, and you know, their wonderful customer service was very helpful as you can imagine. And they told us at the time, like, actually you can't advertise pharmacies on Facebook. Sorry. Like you can't do that. It's a picture of this, right? Like you're, we're a new e-commerce pharmacy. Like we're going to build an amazing digital experience and you lose like the single digital channel that every company is building their business on the back of at that point. And we had us all this back and forth. And finally we got them to agree that if we got this thing called VIPs, which was like this, which was this accreditation for online pharmacies that then we could advertise on Facebook, which is great news. It's now, I don't know, March of 2014 or something. And we go, we contact VIPs and like, Hey, when did you get this accreditation and accuse who we are? And it's like, cool. Yeah, here's the process. And they sent us this long, like overview of all the things we had to do to get the accreditation. And on average, it takes about 12 months to get this accreditation. We're like, Oh God, like we don't have 12 months to figure this out. From a financing standpoint, we got incredibly lucky because, and this is not usually a lucky turn of events, but Fred at the time had been at Accomplice, which was a fund in Boston and led the series A from there. Fred left Accomplice and went to Excel and he knew the company super well. Obviously he liked the business and he just knew that this was going to work. When he took a flyer and he made a bet on, on PillPack in September of 2014, before we had any real customer acquisition working, like we were hacking our way to get some customers and the product was working. He then led the round in 20, in the kind of backup of 2014. We also let in the folks from Slow Ventures into that round to our early Facebook folks for this reason. We got VIPs probably September, October of 2014. So a bit faster than normal, but it still took six or eight months or something like that.

[Harry] Once you got it, was Facebook as impactful as you thought it would be? The customer acquisition.

[TJ] So we raised that $9 million round in September, ads on in probably like October or something like that. And I'd say within three weeks, it was a whole different situation. We turned the account on, customers were signing up at a CAC that we were happy with and we just started turning the knob and the business started growing. It was that straightforward. And from the back half of 14 through the middle of 15, it was just scaling and we raised a $50 million round six months later or something.

[Harry] There's nicely, but like $9 million when you didn't really have any customer acquisition going, did you get an absolutely torrid structure to that deal? Like dilution wise?

[TJ] I think the practical answer to your question is we raised like a nine on 30 post or something. So no structure, but you got to do what you got to do. Yeah, I think that was market-ish. This was not 2018, 2019, but it was fine. Like I've never once looked back and be like, Oh my God, I got so diluted. Like I could have so much more money right now. That's just silly. It worked out great. We raised the round and we moved on and then we raised around a couple hundred pre, nine months later. And so that one was probably way too frothy and the one before was low, maybe, but like at the aggregate, it was fine.

[Harry] I have to touch on the element that you said earlier being kind of incumbent responses. Incumbents respond in varying ways. I hear there's an interesting story here. How did the incumbents respond to you when things started to hum and take me to that story?

[TJ] So I think the place we were woefully naive at PillPack when we founded the company was this, right? We didn't really understand why there weren’t more e-commerce pharmacies. There's all these big winners and pharmacy, there's basically, there was no e-commerce player before PillPack. Like that didn't exist, right? CVS and Walgreens, there's PBM owned mail-order pharmacies. There's no e-commerce business. Well, that's weird. We should just build this. We'll be great. We'll build a great customer experience and it's going to be awesome. And there are the things called PBMs, which stand for pharmacy benefit managers. And they are companies like Express Groups, CVS Caremark, OptumRx, and they're the equivalent of insurance companies, but only for your prescription drugs. Historically, they were in two different businesses. One was managing your benefits. So how much is your copay? Which pharmacies can you use? How much is your out-of-pocket? Which medications are covered? Like all the things an insurance company does. And then the other half of their business was owning and operating mail-order pharmacies. So they did home delivery for consumers. And so obviously they weren't particularly thrilled about other companies competing with them in that second category, right? They had a captive market on doing home delivery in pharmacy.

[Harry] Aren't you fked? Because if they're the ones who are saying, hey, we'll own the transaction mechanism, we're the insurers of these prescriptions and we're not going to give pill pack advice, aren't you fked?

[TJ] Yes, you are f**ked. This is why I say you would have never started this company if you knew how the industry dynamics work. It's why no healthcare investor would have invested in this company. This is idiotic. There's no way.

[Harry] But I'm a tech investor and respectfully, that's like the most core thing. The core supply side can't engage because it cannibalizes their own business.

[TJ] Oh yeah. I was horribly confident that this would be a non-issue. I've run pharmacies before you just how you fill out the paperwork, you get in network with the insurance companies, like it's fine. And that's actually what we did. Like we started a pharmacy and we got in network with all the insurance companies and it was totally fine. So like 2013, 14, first half of 2015, like we were in network as a small little independent pharmacy, like any other independent pharmacy. And they didn't care, right? Like why would they care? We're doing like very small amounts of volume. They didn't even know who we were, frankly. We filled out like very administrative paperwork to get in network. And then we got our Facebook ads turned on and the company started scaling and started growing really quickly. And of course they see every transaction that you process because they are the transaction processor. And then things change quickly, right? Like we get to the middle of 2015, we went from $10 million run rate to a $70 million run rate in six months, nine months, something like that. Then they started really caring, right? And so now like everyone knows who PillPack is and we got very lucky. We got this guy, Jim Messina, who was Obama's deputy chief of staff joined our board and he joined our board, especially to help us navigate regulatory and incumbent issues like this. And he's very good at this. Through 2015, but we got termination notices from all of the major PBMs very obviously. And I would say every one of them, but Express Scripts, we worked through in a very kind of private, professional way with them. And NetNet, we maintained access. We maintained coverage mostly because we were already serving the customers and their customers liked the product. And it would have been very painful for them to take it away was the sort of base of that.

[Harry] Do you not have been more aggressive and just taken vertical ownership and done the payment processing yourself too? And then actually really?

[TJ] Like literally impossible. Yeah.

[Harry] Why? It's not just payment processing.

[TJ] They're the equivalent of you can think about a PBM or honestly a payer in general as like the demand aggregator in healthcare. They own that demand. They own the employer relationships. They have the Medicare relationships. As a startup, you could not have built what they had built unless you're building an entirely different company. You can't do it when we're building the equivalent of a retailer, like literally impossible.

[Harry] So what happened then?

[TJ] So early 2016 Express Scripts sent us a termination notice, honestly looks the same as all the other termination notices we had received and we had managed quietly and figured out. And we reached out to them the same way we did with the others and try to get a meeting and try to help figure it out. We had two weeks, right? So termination notice states like in two weeks, you can no longer serve Express Scripts customers. Like you can't process transactions. For context, they are the largest PBM. So this was like 40% of our revenue. And as far as we knew in two weeks, like that revenue goes to zero. We spent a week just trying to get in touch with somebody and they were just radio silent, would not even engage with us. And so we made the pretty aggressive decision to start a public war. And so Colin Rainey, who had started like three days before, designed a full explainer video that talks about what a PBM is, what they do, why this matters. And that we filmed a customer testimonial of one of our customers. And I think within two days had 1400 or 1500 like customer testimonials. And these weren't like, oh, like, it'd be so sad to lose PillPack. I love the packaging. It was like, if we lose PillPack, like I'm not to put my mom into a home and we don't really know actually what we're going to do. And it was 1500 of these. Right. And so we built a whole website, fixpharmacy.com had all the customer testimonials on it, had the explainer video, the customer video, and then we had all this wonky stuff or regulators if they want to drill into what was going on. And then we just did a massive PR blitz. So we launched the site. I think we had 40 articles in two hours and we leaned super heavy on this actually is going to be really bad for these customers. This isn't like a David and Goliath, like hopefully one of the businesses wins and one loses. This is going to be super bad for the customers that are using this service. And then we ran a regulatory process and tried to do what we could do. And I think within 24 hours Express Scripts was at the table and then it gets even crazier. So we're now like, let's five days later, we've got two days to get this contract fixed. Now it is a business negotiation. We're trying to find a path forward with Express Scripts. I don't think anyone's heard this story ever, but Elliot and I were sitting in a conference room with Colin. I'm sitting on my laptop or like the war room, right? We've got all the site design on the walls. It's just like a classic war room. I get an email from like the equivalent of our GPO for all of the other PBMs. Like you have a, like a GPOE type thing that sits between you. And they're like, Hey, like we sell this Express Scripts. This seems bad. Like actually we're going to kick you out too. And so we were 48 hours from going from, I don't know what it was, a hundred million in revenue to zero, like zero. We have to now both, I have to go figure out how to fix the Express Scripts thing. And we've got to go figure out how to like fix all of the other contracts, like at the exact same time. And so I'm sitting there, I get the email, like I don't say anything. I just turn the computer around to Elliot who looks at it. We say nothing for probably three minutes and Colin's sitting like, Hey guys, like what's going on? The two of us walk out and I'm like, Elliot, you got to figure out this GPO thing. I don't know how we're going to deal with that, but you got to figure it out. And I was like, I'll figure out Express Scripts and we'll figure it out. And by Friday night, that was the end for both. Elliot had found a new GPO, done all the tech work and administrative work to flip into it. And I had signed a new contract with Express Scripts and we had not lost a single contract and we had solidified ourselves like publicly. As a company that was going to exist in the space, like in perpetuity. So it was as live or die as you're ever going to see. And yeah, that was what that sort of make it moment for the business.

[Harry] Are you panicking at that point? That is a holy shit moment. How do you keep your cool like TJ?

[TJ] I have a personality that when things get really intense, like I get calm. I don't, the opposite doesn't tend to happen. So it was incredibly stressful, but I also felt like I was in my element. There was like an enjoyment. It's a battle and we're going to figure it out. And we're like, we're playing a chess match here and certainly was stressed. It certainly was not sleeping well. But at the same time, like there was like a, an enjoyment to it. And obviously when we pulled it off, like it solidified the business in a way that we couldn't have done any other way. And similarly, like this is one of those decisions that like, I think if you were a little too anxious and you want to make the decision, like you would have wanted to get ahead of this one. Like you would have wanted to like, ah, we should go do some BD deal with them. Like, let's figure this out. And I was like, nope, none of that felt right. It's not going to work. Let's just play this out and see how it plays out. And I don't think there was any other path to pulling this off than the one we took, but you could have also never like architected this path. It was just building something great for customers. And when it mattered, those customers came and defended the access that they had.

[Harry] TJ, why on earth did they relent? What, what made them pull back?

[TJ] There was no excuse from a customer standpoint, right? Like it was all in fighting between businesses.

[Harry] You mentioned Amazon. Now I have to ask in 2018, Amazon reportedly attempt to acquire and successfully do for a very large number. Talk to me about the decision making process there that comes in. What's the decision making and how did you get to the deal?

[TJ] Yeah. So if you zoom back to that moment, I think it was like mid 2017, early 2017, probably. We had just finished overhauling like all the software that powered the pharmacy. So when we started the company, we just bought everything off the shelf. Right. And over time we were ripping components out and ripping components out. And by early 2017, we had rebuilt and ripped out all of the underlying tech and that powered the pharmacy. And we had this moment where we like picked our heads up and we're like, what should we do now that we've done that? Right. Almost all our resources have been focused on that for the longest time. And we had this idea of could we offer our infrastructure up to other participants, right? So it could be another startup that needs to launch a pharmacy experience, actually Row launched on our infrastructure. And as part of that, we were meeting with all the large retailers and other potential customers to build on top of that. Right. And one of those large retailers went from a very commercial conversation to an acquisitive conversation, like relatively quickly.

[Harry] How do you know when there's going to an acquisition from a partnership in a normal conversation?

[TJ] Yeah, usually when they call and say, Hey, could we just buy the company? It's pretty clear it moved from like a commercial thing to an acquisitive thing. I wasn't reading the tea leaves at the same time, but it was pretty explicit at that point. And I think we looked at where we were and a couple of things had happened. One, like we were now like a version of scale, right? Like a couple hundred million in run rate or something like that. And we had a very good sense of what our economics were and what it was going to take to build what we really wanted to build. And from that standpoint, like it was going to be pretty capital intensive to scale this thing to the extent that we want it to, right? Like it was doable. Like we could have definitely built an independent company, but it was going to be capital intensive. And then probably more importantly, like when we started to pull back, like it was a very simple vision, which is just made this as easy as possible for consumers. And I think as we started pulling on that string over the years, like we had all these incumbent issues and everything else, we were more ambitious, right? Like we wanted to fix the supply chain. We wanted to fix a bunch of other stuff in the industry. And we had gotten convinced that the best way to do that was to make pharmacy a shoppable, like e-commerce experience and a bunch of stuff falls out of that ultimately reshapes the dynamics. And so the combination of those two things, like the best place to do that is at a large retailer that already exists. And so it was pretty straightforward. And we made the decision assuming that the terms came to a place that made sense that we would probably sell the company in like the back half of 2017.

[Harry] Okay. So you decided that you're going to sell a company in the back half of 2017 and needs a lot of cash to get it to the scale that you think it can be. There's a process to run. How did you think about running that process? You mentioned that the early interest, I'm sure there was many other interested parties. How did you run that process? And what was that decision making on Ultimate Acquirer?

[TJ] That same initial kind of retailer that had flatly wanted to buy the company got to terms that we were comfortable with. And we spent some time with other acquirers, but it was clear that they were the lead horse and it was probably the right fit and the best option. And so this is early 2018 and we had, I don't know, six months of runway in the bank or something. And so normally that's when I would have raised around, right? Like raise 18 months, then probably raise when you've got six months of runway left, something like that. And so we had started a fundraising process in January of 18. And then within a few weeks of that going, we got to terms with a potential acquirer and we assumed we were going to sell the company to that acquirer and we shut down the fundraising process. We sort of full steam ahead on getting the deal done. Honestly, we were days, like not weeks from being done, like announcing like this thing is done, like definitive agreement done and it hits a snitch or it hits a snag and it's going to get delayed. The whole board thinks we're selling the company in three days. I think we're selling the company in three days and now it's not going to be three days. It's going to be some unknown amount of time. And now instead of having six months of money in the bank, I've got two months maybe because like we're selling the company in three days. Like I had two months of money is great. You've perfectly timed it. I had to tell the board, obviously, as I got a phone call Thursday night, I tell the board on a Friday morning, I picked back up the fundraise, like I'm flying to San Francisco Monday morning. I'm going to New York on Wednesday and then maybe I'll go to see if I can get a meeting in Seattle with some other potential acquirer by the end of the week. And that's what I did. So I got on a plane and I went back and met with all the potential funders, not acquirers and told them what happened. I thankfully, like we'd shared all our numbers in December, January, and we'd beat all those numbers in like April or whatever this was. And that's better than if we had missed them for sure. And it was kind of like, we're up for anything. We'll figure something out here, but we don't have a ton of time. So let's just be creative. Then I had the meeting with the company in Seattle and it was definitely the best pitch in my life. And at that point, I knew we were selling the company to Amazon, like all of our vision around what to do with pharmacy and how to make it shoppable and all those things. We were just super aligned. And at that point, I knew we were going to sell the company to Amazon and ultimately we did. And it was a great outcome.

[Harry] How did it come to a price? What does that look like in terms of that negotiation process?

[TJ] Yeah, it's a dance. By the end, yeah, I sat on the phone and said, I want a billion. That's definitely what happened. But getting to the first deal was a dance. And it was about where different companies valued, where the investors positions, what's an economic outcome that's good for everybody. And if we can't get there, we're just not going to do a deal. It's not like we had to sell the company. We could have raised another round and kept going. And so that was more of a dance. By the time I got to doing the deal with Amazon, like ultimately it was a phone call that was like, if you hit a billion, we're done. And they hit a billion and we were done.

[Harry] When you have a deal like that, and you can tell me if I'm offering too many questions, is it like a billion and you get the cash? Is it like a billion and earn outs? How did deals get structured?

[TJ] So we had three potential buyers. Each structure was different, whether they bought the whole thing or most of the thing, or whether it was all upfront or there's some earn out. And they were varying degrees of those things. But I would say by and large, every deal is going to have some of the money upfront and some of the earn out. And so I think we announced in June, no money then, because like you haven't closed yet. There's this whole like regulatory process and everything that takes some time. So I would say like for entrepreneurs, that moment from announcement to close, it's a relatively stressful period of time.

[Harry] It's also weird though, because your friends think you're loaded and you're like, no, no, I don't actually have any money.

[TJ] Yeah, you're definitely not loaded yet. There's plenty of deals that blow up in closing, not typically for diligence, but more for government oversight reasons. But then we close in September, then yes, like a lot of money hits your bank account.

[Harry] Does it hit your bank account in one go? And can you just take me to the moment when you saw your bank account? Like were you in the garden with the kids? Where were you when you saw it hit?

[TJ] For me, the moment that was more like endearing was like, was it telling the team, which is the same exact time, right? No, that isn't the same time. That's later. Okay. So we told the team that was better. My dad was there. My mom was there. Like all of the companies that traded in pharmacy and the public markets dropped by 15% in three minutes. So it was the very, that moment was honestly for me was like, was better than when the money hit my account. It was just like such a moment. When the money hit my account, it was just a lot of refreshing. Like is any time lots of money hits your account.

[Harry] Where were you? Were you at home? Were you in the office? Were you with your wife?

[TJ] I actually don't even remember. I don't remember crazily. I certainly remember where I was when we announced the deal, but I don't know where I was when we, when the money hit the account.

[Harry] I've heard quite a few people say bizarre, you're a weird bloke, TJ. I'd be like, I was here. I remember my heart rate, my temperature, but that's why I'm a VC.

[TJ] At that point, it was like such a given. It was going to happen. I don't remember.

[Harry] I love that. Can I ask, I've heard people say like, it's kind of a shame, like TJ's once in a generation founder. The company could have been 20, 30 billion reinventing healthcare on its own. Do you have any regrets about selling?

[TJ] No, I really don't. That (selling the company for more) might be true. It's not, I'm not saying that's not possible, but when we set out to start PillPack, like we just wanted to make pharmacy better. That was the ambition. And we sold the company to Amazon. Like I deeply wanted to build like a shoppable pharmacy experience. And we did that. The thing we built and the work we did at Amazon, it's the only big tech company that's actually providing healthcare and doing real things in healthcare. And so that's a legacy that I'm super proud of and really happy about. And economically, like I don't ever look back and wish I had kept going and it all could have been so much bigger and so much better. Just super happy with the outcome.

[Harry] Two things. We always hear money doesn't make you happy. Money doesn't make you happy. Does money make you happy, TJ?

[TJ] Time makes me really happy and money provides you a lot of extra time. So I'm pretty happy. It's hard to parse. Like when I started the company, I had no family, no kids, none of that. And now I've got three little kids and an amazing family and a super happy with where we live. So I'm super happy. I don't know how much of it's the money or the time or neither. And it's just the family, but I'm quite happy at the moment. No regrets for me.

[Harry] Can I ask you what's been the most lavish purchase since TJ?

[TJ] I have an expensive taste, but I'm not going to go through a laundry list of things I bought. Probably the most, technically the most lavish is we bought this, we bought like a 12 acre farm in the middle of Park City, which we're building. My wife is building like an amazing farm here. We're going to have a bunch of animals and a bunch of fresh produce in the backyard. It's a practical, but quite lavish purchase. And one that I'm excited to build.

[Harry] When you look at your Twitter, it seems like Amazon maybe wasn't what it seemed. Is that an unfair response? And do you think your negativity online fairly reflects the experience?

[TJ] I think the negativity is probably a little overstated. When we sold the company to Amazon, my goal was to build and launch pharmacy on dotcom and make all those like very non data driven, like nuanced decisions, like intuitive decisions to get that thing off the ground and then hand it off to Amazonian. That knows how to turn the crank and really build like a scale business in a way that I honestly just don't. I don't think Amazon is any worse than any other big company, but it is a big company and it comes with all the trappings of a big company. And I think for me, given like the very beginning of our conversation where it was like, do you like stability and are you comfortable with authority and do you like predictableness or not? I am so far in this extreme that honestly, like, I don't think I would be super successful at any big company. I'm a startup guy. And so no, like functionally thrilled to be built and Amazon is a big company.

[Harry] So quickfire round, following what we just said there, what's the single best thing about being an Amazon?

[TJ] Exactly how happy it's made me to now not be at Amazon.

[Harry] I love that one. Listen, next one, what do others not know to be true?

[TJ] That I think that customers are ultimately going to shop healthcare like they shop everything else and that until that happens, like healthcare is going to remain as fucked up as it is right now.

[Harry] What's the biggest advice on effective board management?

[TJ] I think be a normal human, create normal relationships with your investors and your board members, text them, call them when things are good and bad, get breakfast, make David Tisch buy you sushi, like do all the things that you do and great relationships in the rest of your life with your investors and your board members and it'll probably be fine.

[Harry] What's the strongest belief you had, which turned out to be wrong?

[TJ] I used to think that people could like float between different types of companies and jobs pretty seamlessly and it would be fine. And for some of the earlier conversations, I think that like, you should really optimise for what your personality is best at. The likelihood that you're both really successful and really happy in a huge company and then also really successful and really happy in a startup is unlikely. And so I think I've changed my tune on that one.

[Harry] Who's the single most impactful angel of the Pill Pat journey?

[TJ] I think you got to give it to the first person that ever bet on you, which for us is Katie Ray and Zen Chu and Katie was the one that was running Techstars when we got to the Techstars, like she bet on us before anybody else. And so it's hard for me to not give that to that kudos to Katie.

[Harry] What would you most like to change about the world of venture?

[TJ] I'd really like for 20 somethings that have never built a business to stop like pontificating on how to build a business. Just kidding. Love you, my friend. My son's name is Harry. It's named after you. I love you. I'm just kidding.

[Harry] I love it. This is what people think about me and I'm like, do you know what they're teaching? And it is the most frustrating thing for me, which is like people who think that, which I totally understand from the outside, but it's like you don't see two 10 million a year revenue businesses with 80% margins. I've got 100 people.

[TJ] I bought some really terrible business with 20% margins, so you're better than me.

[Harry] Yeah, I'm not saying that, but it's perception and reality. And tell me, my friend, you can have one board member who's the best and why them?

[TJ] I got to give that one to Elliot Cohen. He was definitely my best board member. We were always perfectly aligned.

[Harry] What about another board member that's not a founder?

[TJ] Hey, this is rapid fire. There's not time for, to go deep on any of these questions here.

[Harry] Don't tell me what to go deep on in no rapid fire. Oh, I love it. Okay. You know what? I'm going to let you off on that. We're going to do TJ in 2033.

[TJ] Hopefully get the opportunity to keep being involved in building things that make people's lives better. I think it was super rewarding to build PillPack. I'm still young, got a lot more in me. So hopefully still building and helping build things that make people's lives better.

[Harry] TJ, I love this. You sass master. That is brilliant. Honestly, I love doing this. I'm so touched that you chose to do this as your first thing, speaking publicly. Seriously, it really meant a lot to me. And so thank you so much, my friend.

[TJ] Of course. It was my pleasure. I mean the sass at the end there.