The Exchanges

Q 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. Can I ask, how do you, 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?

A Yeah, so a 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. So you have a, 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, like it's, it's very functional. Um, it's sort of like the, the most simplistic, uh, straightforward org design. It's where most companies are going to start. Um, the, a, 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, um, that manage a single P&L and have sort of pockets of each of these functions inside of their business, um, and 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. And almost all of the downsides of a big company that people bemoan, uh, the, the amount of HR, the amount of overhead and decision making, like the, all the over processness, I think it's all a byproduct of that single decision. Um, and I think You, you could not have built a company like Amazon or another large company without doing that, but it has all…

AI assessment note: “a functional org is roughly what I described... a GM-focused org is where”

Q Do you start from a relationship of full trust?

A Yeah, you know, it's funny you ask that. When we were acquired by Amazon, we, we sort of took all of our internal, the equivalent of Amazon LPs, like leadership principles, right, and we tried to mash them up kind of one-to-one with what's the equivalent, like Amazon one, and they actually, like, almost all tracked, uh, sort of one-to-one, like customer obsession and all these things were, were kind of dead on, and the one that was, uh, was the exact opposite was, uh, We had this leadership principle at PillPack, which was my favorite, um, which was assume the best, right? 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 the opposite leadership principle, and I didn't actually think a whole lot of it. Like, we just tried, we mapped them, like, oh yeah, it's kind of the same, earned trust, uh, assume the best. In hindsight, that is, like, literally the opposite culture, right? It's like, It's kind of assumed the worst until you're proven otherwise. Um, and so, yeah, I, like, we built a culture that assumed the best, that, that we, people showed up, we made bets on people, um, and then we assumed that they …

AI assessment note: “we built a culture that assumed the best... and we trusted them.”

Q 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?

A I always think about, like, each round for a classic venture-backed company as trying to be super crisp about the thing you're trying to prove on that round of financing, right? So, like, obviously, like, your first round of financing, you're doing a bunch of stuff. Like, you gotta build a product de novo, you gotta sort of pseudo-build operations, you gotta build all the components, but, like, 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, really thoughtful about what that is. So, for us, we, 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 the product-ish because we had Elliot on the team, and he had built products before. Um, the, the flyer everyone was taking is, can you acquire consumers online for this company, right? And so the only thing that mattered, uh, sort of post that first round of financing was, can we actually acquire customers online for a pharmacy? Which, You jump back to, like, 2013, like, starting a pharmacy is not what starting a pharmacy is today, right? There's Rho, and HIMSS, and PillPack, and Capsule, and TruPill, like, there's all this great activity in pharm…

AI assessment note: “what is the bet your investors are making, and do you have the right team”

Q 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. Can I ask, how do you, 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?

A Yeah, so a 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. So you have a, 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, like it's, it's very functional. Um, it's sort of like the, the most simplistic, uh, straightforward org design. It's where most companies are going to start. Um, the, a, 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, um, that manage a single P&L and have sort of pockets of each of these functions inside of their business, um, and 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. And almost all of the downsides of a big company that people bemoan, uh, the, the amount of HR, the amount of overhead and decision making, like the, all the over processness, I think it's all a byproduct of that single decision. Um, and I think You, you could not have built a company like Amazon or another large company without doing that, but it has all…

AI assessment note: “a functional org is roughly what I described... a GM-focused org is where you've got single-threaded leaders”

Q Do you start from a relationship of full trust?

A Yeah, you know, it's funny you ask that. When we were acquired by Amazon, we, we sort of took all of our internal, the equivalent of Amazon LPs, like leadership principles, right, and we tried to mash them up kind of one-to-one with what's the equivalent, like Amazon one, and they actually, like, almost all tracked, uh, sort of one-to-one, like customer obsession and all these things were, were kind of dead on, and the one that was, uh, was the exact opposite was, uh, We had this leadership principle at PillPack, which was my favorite, um, which was assume the best, right? 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 the opposite leadership principle, and I didn't actually think a whole lot of it. Like, we just tried, we mapped them, like, oh yeah, it's kind of the same, earned trust, uh, assume the best. In hindsight, that is, like, literally the opposite culture, right? It's like, It's kind of assumed the worst until you're proven otherwise. Um, and so, yeah, I, like, we built a culture that assumed the best, that, that we, people showed up, we made bets on people, um, and then we assumed that they …

AI assessment note: “we built a culture that assumed the best, that, that we, people showed up”

Q Man, you mentioned comp as one of the reasons like 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?

A I didn't appreciate this nearly as much as I probably should have at the time, um, but incentivizing your team as much as possible on equity ends up being, like, the biggest lever you have from a cultural standpoint. Obviously, it's a lever from an economic standpoint, but if you take, kind of, PillPack Preacquisition versus PillPack as part of a big organization, PillPack Preacquisition, 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, um, 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. Like, 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. Um, and so everything kind of falls out of that. Like, we, we're gonna win or we're gonna 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, it's stock, um, 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, um, and I, I, I appreciate-

AI assessment note: “incentivizing your team as much as possible on equity ends up being, like, the biggest lever”

Q I also just go kind of 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. I don't think I really have one at all, and that structure I didn't have. Um, how do you think about your parenting today, having had that predictability, and is that what you want to give them, or not?

A You know, 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 I think the, the thing that we're trying to provide for our kids is the ability to go explore, uh, be kids, to be able to have independence, and to grow independence early, which I did have in my childhood. Like, we, we were, like, classic eighties, nineties kids that hopped on a bike and took off and came back before dinner. Um, and so I'm trying to, I'm trying to keep that, um, because for me that was sort of the magic of childhood, was being able to go build forts in the woods and be gone for the whole day. It wasn't, uh, It wasn't sort of like, my schedule's packed, and I, I want to make sure I provide that for my kids. And certainly, hopefully our environment is stable, but it, for me, that's the thing I think about a lot, is how do I, how do I retain a childhood that is, for the most part, now gone for a lot of kids.

AI assessment note: “I don't know if it's As much about predictability versus non-predictability”

Q What do you think is the single best decision you made with PillPack, and what did you learn from it?

A I mean, it's hard for me not to say that it was starting the company with Elliot. I mean, he's been an amazing partner in the PillPack journey. Um, but I think it's hard to learn much from that other than be, it's sort of like better to be, be lucky than smart. Uh, we didn't know each other that well. Like, we had, we had done a couple things together, but we just got incredibly lucky. 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, is that almost no one is actually building for the customer that's, that is using the service, and so we, we effectively put on blinders to everybody else, um, and so 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, um, that's totally fine, we'll do the weird stuff, um, and if, like, a, a provider or a payer is upset about the way we're doing something, but it's better for the customer to 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, um, and it ena…

AI assessment note: “a weird decision that we were only going to focus on the end customer.”

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

A No, it's 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 sort of augmenting the things I thought I understood, um, and it was less about whether they'd say yes or no for me. It was, when you look at the pill pack business, yes, it's a, it's a healthcare company, it's a, it's a pharmacy, um, 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, you know, like 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. Um, 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.

AI assessment note: “No, it's probably a little different than that. I think I thought I didn't”

Q I get you. Um, I, I want to dive into a couple of elements of the story. Uh, which I think are really important. Like, as we said before, it's very easy to look at PillPack and think, ah, 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?

A Yeah. I talked a little bit about that sort of first bet, right? Like we, we started the company, we raised about four million dollars between two quick rounds right out of the, right out of the gate. Um, and the bet people were making is that we can acquire customers. Like everyone assumed we'll start a pharmacy. They assume we'll get in network with payers. Like all that stuff was a given. Um, so if you jump forward, we raised, we started the company in, um, we raised that round kind of middle of, um, and we launched the product in early, um, and for folks that were around at that time, Like, the way you acquired customers was buying Facebook ads, like, point blank, but that's how every DTC company was scaling. And so we assumed, like, we're gonna do the same thing, we're gonna buy Facebook ads, and like, hopefully the economics work, and hopefully we can acquire customers in this category. And we launched, we got our ad, uh, our ads turned on, and I think within, 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, like, 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. Um, and they told us at the time, lik…

AI assessment note: “our account got shut off. We got, like, suspended from Facebook ads.”

Q How do you come to, sorry, I'm so naive, how do you come to a price Do you sit across the table and be like, I want a billion. And they're like, okay, great. Good for, good for you. I, how, what does that look like in terms of that negotiation process?

A It's a dance. By the end, like, yeah, I sat on the phone and said, I want a billion. That's definitely what happened. But, you know, getting to the, the first deal was just, it was a dance and it was about where we think the company's valued, where the investors positions, like 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. Um, 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. Um, and they hit a billion and we were done, but you know, that's the byproduct of lots.

AI assessment note: “I sat on the phone and said, I want a billion. That's definitely what happened.”

Q Man, you mentioned comp as one of the reasons like 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?

A I didn't appreciate this nearly as much as I probably should have at the time, um, but incentivizing your team as much as possible on equity ends up being, like, the biggest lever you have from a cultural standpoint. Obviously, it's a lever from an economic standpoint, but if you take, kind of, PillPack Preacquisition versus PillPack as part of a big organization, PillPack Preacquisition, 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, um, 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. Like, 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. Um, and so everything kind of falls out of that. Like, we, we're gonna win or we're gonna 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, it's stock, um, 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, um, and I, I, I appreciate-

AI assessment note: “incentivizing your team as much as possible on equity ends up being, like, the biggest lever”

Q 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?

A I think the negativity is probably a little overstated. It's more of like an eh, eh, eh. When we, when we sold the company to Amazon, my goal was to build and launch PharmacyN.com 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 an Amazonian that knows how to turn the crank and really build, like, a, a scaled business in a way that I honestly just don't. Um, I don't think Amazon is any worse than any other big company, but it is a big company, uh, and it comes with all the trappings of a big company. Um, 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, uh, predictableness or not, I am so far on this extreme that honestly, like, I don't think I would be super successful at any big company. I'm, I'm a startup guy. That's just kind of how it is. Um, and so no, like, functionally, Throttle will be built, um, and Amazon is a big company.

AI assessment note: “I think the negativity is probably a little overstated.”

Q 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?

A Yeah, I think it's important in the sense that, I think it's really important to understand the customer problem. Um, 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. Um, but I do think if you don't deeply understand the customer problem, it's likely you'll build the wrong solution. So I think that's where we were uniquely, 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 spend enough time in customers' homes that I, 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.

AI assessment note: “I think it's important in the sense that, I think it's really important to understand”

Q What else are you running from, TJ? Personally?

A Yeah, I think maybe to more seriously answer your question, I, I had this conversation with someone a couple months ago that made the comment that kind of stuck with me that we're always probably looking for the opposite of Of the environment that we had as a kid to some degree. And I, you know, for me, uh, if you zoom way back, like, my dad grew up with almost nothing and worked, worked incredibly hard to become a pharmacist, to, to give us a childhood that was, was way better than his. Um, but it was like a very kind of leave it to beaver childhood, right? Very, uh, very predictable, very stable, just very kind of classic. And I think I was always looking for a little more excitement, a little more risk. Uh, in my life, and so I think startups were a great way for me to harness that, um, but probably, probably led to me being very uncomfortable in, uh, very formulaic, stable environments.

AI assessment note: “uncomfortable in, uh, very formulaic, stable environments”

Q going around picket fence, kind of, uh, ecosystems, but I, I want to move from like- That was definitely my childhood. I think great, um, 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?

A I think a thing that I believe now that I did not believe during the early part of the Pillback Journey, or honestly, probably into the last couple years, is that there are folks that are on, like, sort of the extreme ends of this from a personality standpoint. Like, I think there are folks that truly are, like, much more comfortable in uncertainty than they are when things are, 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. Um, but for me, I was way far on the, like, I'm super naturally comfortable Um, in an uncertain environment, it's kind of my happy place. It's not, so like, I don't have a lot of tactical advice on, like, you gotta meditate, you know, Monday to Friday from eight to nine. I didn't, there was not a lot of these mind games that I was trying to play, and so I think the advice I do have is, like, 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, uh, that lifestyle, you'll honestly probably be happier, uh, 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, um, and less about like the tactics of how to, how to sort of manage your psyche.

AI assessment note: “for me, I was way far on the, like, I'm super naturally comfortable”

Q one would ever fucking do it, ever. Um, so that's not good for our business. Uh, but I, the other aspect that you said, as well as being uncomfortable, uh, 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 well?

A Yeah, I think this would actually be way harder for me now. I think, you know, I sort of pulled back, 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, right? There was no, there was no way I knew how to, 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 Uh, 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, in being young and not having experience in this context.

AI assessment note: “I had no preconceived notion that I had any idea how to do the tactical jobs”

Q What can you do to increase your speed of execution?

A It goes back to hiring great people, and mostly getting out of the way, and giving them the autonomy to make decisions. Um, 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. Um, 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, and they'll certainly be, if it's even cuspy on the, on the bigger decisions, they'll be coming to you and you'll be working through it. Um, 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, and go as fast as possible.

AI assessment note: “hiring great people, and mostly getting out of the way, and giving them the autonomy”

Q 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?

A I mean, we'll get into this a bit more probably later in the podcast, but 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 20 14 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, and sort of try to work through this productively before it blows up in our face. And, and like 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. Um, and in reality, we just sat on it and we let it, we let it ride. Um, and we'll, we'll get into the details of it later, but it ended up becoming like the, the, the make or break moment in the company. And I think it was the only way that we could have possibly, uh, pulled off what we did pull off.

AI assessment note: “in reality, we just sat on it and we let it, we let it ride.”

Q When you say a real operator, is that, 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?

A Yeah, tangibly, we, it was a CFO, COO, like one human that owned both of those functions that we brought in, uh, this woman, Yvonne, who was incredible, um, and really brought the business to a place where it was much more scalable, and it was, everything was humming, so she owned both of those functions, which obviously is, is a bit rare, but tactically, we started the business, we had a, we had a head of ops that, um, I had known for a long time, but was young, hungry, like, knew the business super well, Um, it was actually the first person I hired, uh, in the pharmacy when we started the business, uh, and he scaled that thing to four or 500 people, like, zero humans to, like, 500 people or something in operations, and, like, was more dedicated to the business and the customer than anyone I've probably ever met. Like, I, I bet he slept in the pharmacy 40 days in one year, uh, in the midst of this kind of scaling process, and was just able to figure anything out, right? Like, If something was going haywire, like, he would find a way to figure it out. And that was amazing. That's, like, the perfect archetype of, like, an early operational leader is, like, they deeply know the domain. They're happy places, not, like, going and building unnecessary process. They're happy places, like, let's just go figure this thing out. But at some point, that approach breaks, right? At some poi…

AI assessment note: “tangibly, we, it was a CFO, COO, like one human that owned both”

Q I get you. Um, I, I want to dive into a couple of elements of the story. Uh, which I think are really important. Like, as we said before, it's very easy to look at PillPack and think, ah, 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?

A Yeah. I talked a little bit about that sort of first bet, right? Like we, we started the company, we raised about four million dollars between two quick rounds right out of the, right out of the gate. Um, and the bet people were making is that we can acquire customers. Like everyone assumed we'll start a pharmacy. They assume we'll get in network with payers. Like all that stuff was a given. Um, so if you jump forward, we raised, we started the company in, um, we raised that round kind of middle of, um, and we launched the product in early, um, and for folks that were around at that time, Like, the way you acquired customers was buying Facebook ads, like, point blank, but that's how every DTC company was scaling. And so we assumed, like, we're gonna do the same thing, we're gonna buy Facebook ads, and like, hopefully the economics work, and hopefully we can acquire customers in this category. And we launched, we got our ad, uh, our ads turned on, and I think within, 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, like, 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. Um, and they told us at the time, lik…

AI assessment note: “out of nowhere, our account got shut off. We got, like, suspended from Facebook ads.”

Q How do you come to, sorry, I'm so naive, how do you come to a price Do you sit across the table and be like, I want a billion. And they're like, okay, great. Good for, good for you. I, how, what does that look like in terms of that negotiation process?

A It's a dance. By the end, like, yeah, I sat on the phone and said, I want a billion. That's definitely what happened. But, you know, getting to the, the first deal was just, it was a dance and it was about where we think the company's valued, where the investors positions, like 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. Um, 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. Um, and they hit a billion and we were done, but you know, that's the byproduct of lots.

AI assessment note: “By the end, like, yeah, I sat on the phone and said, I want a billion.”

Q 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?

A I think the negativity is probably a little overstated. It's more of like an eh, eh, eh. When we, when we sold the company to Amazon, my goal was to build and launch PharmacyN.com 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 an Amazonian that knows how to turn the crank and really build, like, a, a scaled business in a way that I honestly just don't. Um, I don't think Amazon is any worse than any other big company, but it is a big company, uh, and it comes with all the trappings of a big company. Um, 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, uh, predictableness or not, I am so far on this extreme that honestly, like, I don't think I would be super successful at any big company. I'm, I'm a startup guy. That's just kind of how it is. Um, and so no, like, functionally, Throttle will be built, um, and Amazon is a big company.

AI assessment note: “I think the negativity is probably a little overstated.”

Q You mentioned Amazon now. I, I have to ask, you know, in 2018, I think it was, uh, Amazon, you know, reportedly, uh, attempt to acquire and successfully do, um, for a very large number. Talk to me about the decision making process there. That comes in. What's the decision making like, and how did you get to the deal?

A Yeah, so if you zoom back to that moment, I think it was, like, mid 2017, early 20 17, probably. We had just finished overhauling, like, all the software that powered the pharmacy, so we, like, when we started the company, we just bought everything off the shelf, right, and over time, we started ripping components out and ripping components out. Um, and by early 2017, we had rebuilt, um, and ripped out all of the underlying tech, um, and that powered the pharmacy. Um, and we had this moment where, like, kind of picked our heads up, and we're like, what should we What should we do now that we've done that, right? Almost all our resources have been focused on that for the longest time. Um, and we had this idea of, like, could we offer infrastructure up to other participants, right? So could be another startup that needs to launch a pharmacy experience. Actually, Ro launched on our infrastructure. Um, and we were offering, like, this as, like, a fulfilled by Amazon kind of B to B business based on the fact that we had the tech, the insurance contracts, the licensing, like, the infrastructure. Um, 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, like, a very commercial, uh, uh, conversation to an acquisitive conversation, like, relatively quickly. And by kind o…

AI assessment note: “one of those large retailers went from, like, a very commercial, uh, uh, conversation to an acquisitive conversation”

Q 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 twenty-six-year-old Merfance who didn't know what good looked like and only knew pharmacy?

A Yeah, you know, I do think I felt, I was able to focus on the things that I thought I had to be good at, and I was sort of more naturally inclined 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, so there was no muddiness around what we were trying to achieve, and it was, it was, it was a big vision. As far as understanding who was good and not good, I mean, a lot of it was intuition and trying to read people, and I think it's hard to articulate how to, how to manage intuition or how to be better Uh, at reading people, but it was a lot of that, and then, uh, 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 that, was roughly, like, if you're, if you're a terrible hiring manager, you're right, like, 40% of the time, and if you're an amazing hiring manager, like, world class, you're right, like, 65, maybe 70% of the time, and my takeaway from that was like, well, I better be really good at changing my mind if I'm wrong, and that's the only way to get to, like, 90 plus percent is, if we hire someone that's not going to work out, be really quick at making that call and trying again. Um, and I took that to heart, and I definitely, I definitely behaved that way as we bu…

AI assessment note: “a lot of it was intuition and trying to read people”

Q Why did you not have the confidence, and what gave you that confidence in the end?

A Yeah, I mean, I'm a little bit more of a non-traditional founder, right? I didn't go to, like, an elite school. I didn't, I didn't have the sort of normal connections that, uh, 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, uh, a normal entrepreneur in that context. Um, and in hindsight, like, I think it was more my perception than the actual reality, but that was, that was the hurdle for me. Um, I think once I'd Once I made that jump, uh, it was all, from there, it was very natural. It was more like a snowball rolling down a hill. Um, I kinda, I, 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. Um, and it was like that for sure for me. So we pitched it the first time at like Hacking Medicine, which, uh, is an event that we started, so it's kind of wacky, but we won the event, which is very exciting. It was, it was, uh, it gave me the confidence, uh, for better or worse. Um, this is like the fall of 20 12. I'd been a pharmacist for about six months, so like fresh out of school, and I think within a month or two, we were in, we got into Techstars. Quit my job, kind of, kind of, like, January of 2013. Um, but I think that it was, for me…

AI assessment note: “we won the event, which is very exciting. It was, it was, uh, it gave me the confidence”

Q You mentioned Amazon now. I, I have to ask, you know, in 2018, I think it was, uh, Amazon, you know, reportedly, uh, attempt to acquire and successfully do, um, for a very large number. Talk to me about the decision making process there. That comes in. What's the decision making like, and how did you get to the deal?

A Yeah, so if you zoom back to that moment, I think it was, like, mid 2017, early 20 17, probably. We had just finished overhauling, like, all the software that powered the pharmacy, so we, like, when we started the company, we just bought everything off the shelf, right, and over time, we started ripping components out and ripping components out. Um, and by early 2017, we had rebuilt, um, and ripped out all of the underlying tech, um, and that powered the pharmacy. Um, and we had this moment where, like, kind of picked our heads up, and we're like, what should we What should we do now that we've done that, right? Almost all our resources have been focused on that for the longest time. Um, and we had this idea of, like, could we offer infrastructure up to other participants, right? So could be another startup that needs to launch a pharmacy experience. Actually, Ro launched on our infrastructure. Um, and we were offering, like, this as, like, a fulfilled by Amazon kind of B to B business based on the fact that we had the tech, the insurance contracts, the licensing, like, the infrastructure. Um, 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, like, a very commercial, uh, uh, conversation to an acquisitive conversation, like, relatively quickly. And by kind o…

AI assessment note: “one of those large retailers went from, like, a very commercial... conversation to an acquisitive conversation”

Q 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 twenty-six-year-old Merfance who didn't know what good looked like and only knew pharmacy?

A Yeah, you know, I do think I felt, I was able to focus on the things that I thought I had to be good at, and I was sort of more naturally inclined 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, so there was no muddiness around what we were trying to achieve, and it was, it was, it was a big vision. As far as understanding who was good and not good, I mean, a lot of it was intuition and trying to read people, and I think it's hard to articulate how to, how to manage intuition or how to be better Uh, at reading people, but it was a lot of that, and then, uh, 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 that, was roughly, like, if you're, if you're a terrible hiring manager, you're right, like, 40% of the time, and if you're an amazing hiring manager, like, world class, you're right, like, 65, maybe 70% of the time, and my takeaway from that was like, well, I better be really good at changing my mind if I'm wrong, and that's the only way to get to, like, 90 plus percent is, if we hire someone that's not going to work out, be really quick at making that call and trying again. Um, and I took that to heart, and I definitely, I definitely behaved that way as we bu…

AI assessment note: “a lot of it was intuition and trying to read people”

Q Okay, help me out as an investor. I meet, sorry, ah, sounds awful, but I meet naive founders, and I'm like, oh, so naive. When is naivety good, and when is it bad? Because it can be bad.

A Yeah. Well, A, I think you have to be a pretty quick study. You got to figure this stuff out as you, uh, as you're building the company. So I think, I imagine a lot of your job is figuring out how, how able the founder is to roll with things. And so I think if you're just naive and you're going to stay there, it's probably going to be a huge problem. But again, I think it is about like the difference between not totally grokking industry dynamics and, uh, grokking the customer. Um, you know, we took money from exclusively consumer tech investors and We weren't out pitching healthcare investors. I think almost every healthcare investor would have said no, um, because of the fact that, you know, the industry dynamics were the way they were, so the investors were just as naive as us on a lot of the dynamics at play.

AI assessment note: “if you're just naive and you're going to stay there, it's probably going to be a huge problem.”

Q How do you know when it's going to an acquisition from a partnership in a normal conversation? Do they say, hey, we want to buy you?

A Yeah, usually when they call and say, hey, could we just buy the company? It's pretty clear it moved from, like, a Like, an acquisitive thing. Uh, I, you know, like, I wasn't, like, I wasn't reading the tea leaves at the same time, but, uh, but it was pretty explicit at that point. Um, and, you know, I think we looked, we looked at where we were, and a couple things had happened. One, like, we, we were now, like, a, a, 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, like, 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 capitally intensive to scale this thing to the extent that we wanted to, right? Like, it was doable. Like, we could have definitely built an independent company, but it was going to be, uh, capitally intensive. Um, and then probably more, uh, importantly, like, when we started to pull back, like, it was a very simple vision, which was 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 the best way to do t…

AI assessment note: “usually when they call and say, hey, could we just buy the company?”