122: The Kettle & Fire Founder Is Fixing How America Pays for Health | Justin Mares, Co-Founder and CEO of Truemed

One of my biggest takeaways from Kettle and Fire and TrueMed is I would frankly never start a non-mission-driven company again. I just think getting a startup to work is so hard that you really just need someone to feel a strong reason and a strong why as to like why they're spending an inordinate amount of time, energy working on the thing that you care about. That's been a very, very big learning.

Welcome back. This is From Startup to Grownup. My name is Alisa Cohn, and today I'm thrilled to welcome Justin Maris to the podcast. Justin is a 4-time founder and the CEO of TrueMed, a health payments platform that's helping consumers use their pre-tax health account dollars for preventative health products. Before TrueMed, Justin co-founded Kettle Fire, the bone broth company that helped bring healthier food into the mainstream. We had a fantastic conversation. We talked about what it was like for Justin to leave Kettle Fire and start over an entirely new industry. He walks through the simple experiments he used to validate TrueMed before building the product and what he learned. We also talked about why founders should launch before they're ready and why building momentum matters far more than chasing perfection. We also got into hiring exceptional early employees, building a mission-driven culture and why that's so important, and deciding when to bootstrap versus raise venture capital. And he also talked about what his venture firm, Andreessen Horowitz, has brought to the table beyond funding. We also talked about leadership lessons that he's learned through the highs and lows of building multiple companies. There is so much practical wisdom in this conversation for founders, leaders, and anyone trying to build something meaningful. So please enjoy my fantastic conversation with Justin Maris.

Justin, welcome to the show.

Thanks for having me.

I'm so excited that you're here, and I'm so excited to get into all this with you. You're a 4-time founder, and I'm considering you a health expert. You're now building TrueMed, which is a health payments platform that lets consumers use their HSA or FSA dollars to pay for preventive health products. Which is kind of very unique, right? The idea is that most people pay for so-called medical things, and these are like preventative things. And I know a passion of yours has been for preventative health. So walk us through kind of the inspiring story that you used to create TrueMed.

Sure. So I previously started a company called Kettle Fire. You know, it's a bone broth company that's in probably every grocery store that many of your listeners will go to. And throughout the years, I saw two things growing that company. One, that there's an incredible demand people that they just want products that make them healthier. Like, this health thing is such a real trend. There's so many problems that arise from people eating foods that make them sick, that, you know, having a lifestyle that's not appropriate. But the second thing that I noticed is there's a lot of demand for this. And when we launched the company, we were selling it like $14 a box. Now it's in most grocery stores at like $6.99. You can get it at Costco for like $5 a box. And at every level, the company grew revenue, we reached more people. But everyone is like, this is expensive. And fundamentally it is true. If you want to invest in your health or you want to be healthy in this country, unfortunately paying for a gym membership, buying healthier food, doing any of these things is expensive. And so for many years growing that company, I was thinking, how could you incentivize people and how could you fix some of the incentives so that people are actually incentivized to invest in prevention, invest in exercise, invest in like healthier food, all these sorts of things. And you know, when I came across this idea, one, the HSA and FSA accounts exist, not something I knew about. They're basically buckets of pre-tax funds. $175 billion in these accounts. But the second thing is what really grabbed my interest, which was that if you get a doctor's note, basically where you are trying to treat, reverse, or prevent a condition, a doctor can basically prescribe you the ability to spend these tax-free HSA/FSA dollars on things like exercise that studies show can treat, reverse, or prevent many conditions. Things like food interventions, things like supplements or sleep aids, or many of the things that Americans are spending like hundreds of billions of dollars a year on. Many or all of these things can be bought using tax-free dollars if you are at risk of chronic disease.. And unfortunately, almost every American is working to treat, reverse, or prevent obesity, cardiovascular disease, like many of the chronic conditions that are just decimating Americans' health. And so that sort of like insight of how do we make things cheaper for Americans to invest in prevention? And then this idea that, wow, this mechanism already exists around writing a letter of medical necessity to help drive more dollars towards these root cause things. I kind of put those two ideas together and came up with the idea for TrueMed.

I love it. Let's define our terms a little bit because I myself only found out about HSA like 2 or 3 years ago. And by the way, I'm a CPA, so like, that's weird. Okay, I should have known such things. So let's define what an FSA and an HSA is so people understand. Sure.

So an HSA, health savings account, basically they are the most tax-advantaged account that exists in the US today.

It's remarkable.

Yeah, it's crazy. So they're triple tax-advantaged, which means you can put in money tax-free, it can compound tax-free, and if you pull it out and spend it on eligible health expenses, you can also pull money out tax-free. Why does this exist? It's basically because the government, you know, 25-ish years ago when they created these accounts, they recognized that medical bills are the number one cause of bankruptcies in the country. Paying for healthcare is expensive, and you are likely to accrue and spend more on healthcare as you get older. And so if you can start saving for healthcare-related bills specifically when you're younger, the idea was like, these can compound, and you know, when you get sick and when you need the dollars later in life, you can spend this money on medical care. Flexible spending accounts, FSAs, are pretty similar except they have one thing. HSAs are meant to compound and be spent on medical bills or be spent on like everyday health expenditures that you have today. Flexible spending accounts are similarly like tax-advantaged, similar caps, you know, $4,500 or so a year for an individual, close to $8,500 for a family. Money, but if you don't use them at the end of the year, they expire. And so you have to spend them all within, you know, a calendar year to try and get people to invest in things like prevention and use those dollars on today's medical kind of things. So those are the two accounts.

That's very helpful. And there are rules around them and all that kind of thing. But like, Justin, I have to tell you, I myself, as you know, I have been a Kettle Fire customer for quite a long time. I drink it especially in the winter. It's quite delicious bone broth. And I always say to myself, oh, it's so healthy, look how healthy I'm being. And I will say it was— it still is, but it was when I started buying, it was expensive. It was. And a lot of things that I get, I know that we're also big fans of Maui Nui, the venison. Oh my God, so expensive. Okay, just expensive. But I myself was not thinking, you know, things are so expensive. I know I'll start a payments company, right? So how did you think having like, it's really a direct-to-consumer and then ultimately just a consumer product company, how did you then yourself think, I'm gonna pivot to more of a payments or an admin type company?

Yeah, it's a good question. I felt very strongly that as I got deeper and deeper into running Kettle and Fire, like I started that company company because I felt very strongly that there were almost literally no companies in the food space that I think about what is the product that we are making firstly through the lens of what is actually going to drive positive health outcomes for consumers. We talk a lot about creating a food system and the type of food company that heals rather than harms. And unfortunately, you know, most 80-something percent of Americans' caloric intake goes through roughly 12 publicly traded big food companies. Those companies for 50-plus years at every opportunity where they have said like we can save 20 basis points of margin in exchange for swapping blueberry juice with Blue 40 or something like that. They've done it. And the result is you have a big food kind of space where we have the worst health that we've ever had as Americans. These companies sell junk, you know, in many cases, like in Kellogg's case, for example, they make a worse product that they use with red dyes and seed oils and like all these sorts of things. They make that product in the US, sell it in the US. They also make a healthier version in the US that they can sell to the UK. But because the UK has more strict food laws, you know, they sell the better version over there and they sell us the crap. And so I just had this strong sense that we want I wanted to start a food company that would be better for the country and for the world. And after running that company for 6 years, you know, I kind of got into it, and I think that it's amazing. Like, I'm so proud of the work that we've done, so proud of the team. But I think that I wanted to try and take a swing at the chronic disease crisis, which I think is the most important problem in the country, at a higher level, at the level of like, not can we put a better product on the shelf for people, but at the level of like, how can we incentivize people to actually invest in prevention? How can we advocate for these lifestyle interventions to be a component and be a part of our healthcare system? And so that was really the impetus of like, I was willing to do a lot different things oriented around this mission of chronic disease and basically landed on TrueMed as the idea that would really make an impact at the incentives layer. And that meant moving into tech, moving into fintech, moving into like health tech in some ways. So yeah, it was a big and surprising departure, I would say.

Yeah, I can imagine. Like, how specifically, tactically did you start, right? So you're like, okay, you— by the way, were you leaving Kettle Fire? I know you're still on the board of Kettle Fire, but did you say it's time for me to move on, or were you more like I am compelled by this new vision. And then at some point you left and you're like, I'm going to start and like, walk us tactically through those early days.

Yeah. So I took some space. I basically had a feeling of Kettle Fire has done extremely well and it was not clear to me that the business needed me as the CEO to go from like where it was at the time I stepped back to, you know, the multi-hundreds of millions kind of revenue mark and things like that. And so I basically decided to step back, took 6 months of a fairly like poorly structured sabbatical to try and figure out what I wanted to do next. And when I came across this idea, to me, there were a couple of things that I wanted to test. You know, it hit the mission boxes. It was like, you know, if this works, I can totally see a world in which TrueMed is building the rails that drive hundreds of billions of dollars towards effective lifestyle interventions. And so very, very much believe that the things that were important to validate were we were going to build this as a payment method. But, you know, worse, 3 years ago, no one knew what HSA/FSA was. And so if we build a payment method and you go to Peloton like you can today, Peloton, you can see TrueMed pay with HSA/FSA. If we just put a button that says pay with HSA/FSA on a website, is anyone going to click it? Does anyone know what this is? And so that was like one very, very material risk. The second thing is I was new, had been working in the food space for most of my career. And so we're entering a regulated space. We're talking about healthcare information. We're talking about practice and medicine laws. We're talking about tax-advantaged accounts. So what we're doing at TrueMed basically touches like 50-state practice of medicine rules. It touches IRS rules. It touches like employment. It hits on a lot of things.. It's a fairly complex business from a regulatory standpoint. And so I basically wanted to test those two things. Well, if we offer this, will people use it? And then can we figure out the regulatory component? And so what we did to actually test it is in the very early days, I put like a manual payment method on Perfect Keto and Kettle and Fire's checkouts, which are two brands that I started. And we basically just like put pay with HSFC and just said, okay, will anyone click on this? You know, if it just sits there, will anyone click on this? The answer was yes. And so we were like, okay, that's quite interesting. We emailed people. We would say, why are you clicking on this?

How do you know what HSFC is?

What do you think? Of what we're doing, and we learned a lot about the early customers. And yeah, what did you learn? Yeah, one of the surprising things that we learned is that there are a tremendous number of people that view things like Peloton, things like an Eight Sleep, things like a, you know, like supplemental bone broth as healthcare interventions, and they have research that backs up these things are like effective interventions. And secondly, like, we had a bunch of these people that were telling us that this is like a thing that they get excited about in terms of ways to spend their HSA FSA. So many people are like, you know, I have X thousands or tens of thousands of dollars in these accounts. I can spend these on contact solution, I can spend these on Band-Aids, but like none of that is exciting. If I can spend it on a Peloton or an Eight Sleep and I have a family history of heart disease, I have a family history of sleep apnea or whatever it is, these are actually incredibly effective uses of HSA and FSA dollars. So that was a really, really big validation point. And after kind of interviewing customers, running them through this sort of smoke test, you could call it, got a pretty good conviction that we could drive, get people, that there's a lot a lot of people with HSFC, they're willing to click on a button that they just find and check out for the first time. And then the question was like, okay, how do we build the infrastructure to make it so that this is, you know, compliant and all these sorts of things? And then we spent a bunch of money and a bunch of time with one of the top telemedicine law firms in the country, got kind of blessing and architected, here's how we're going to approach kind of this problem space, the idea, all these things, and then ended up launching 6 months after having the idea, 9 months after having the idea.

Wow, that's amazing. There's so much to unpack there. So first of all, you had some early customers who said, yeah, this is what I would want to do and this is what I would do. And actually, to your surprise, click the button, pay with HSBC, right? That is remarkable. And then you're saying you had to kind of have the regulatory, obviously, blessing and all the rules and figure that out. Plus, I'm sure working through the user experience, right? Like, there's a little— this complexity to work on there, although maybe you had that kind of insight from your Kettle Fire experiences.

Yeah, in the early days, I didn't worry that much about the user experience. I feel pretty strongly— like, we did this with Kettle Fire too. We launched a product, that product was not very good. And, you know, we are like— the landing page, the funnels, like, everything about it was not very good. We didn't know we were doing pricing, we didn't know how to make bone broth. And so we launched a fairly suboptimal product and people were still using it. And so to me, I saw the same thing with— and I was like, great, if we can actually make the product better, if we can improve the website, we can improve the copy, we can improve like the actual product, way more people are going to buy this. And so I felt that very strongly and felt that similarly with TruMed in the early days is like you had a janky like payment method that would show up on the screen. You would go to a janky like other thing where you share your personal health information. There were a lot of ways ways in which our early product and product experience were super suboptimal. And even then we saw some signs that like people wanted this enough to go through the headache of doing all of the stuff that I'm just talking about. And so that actually was an incredibly bullish sign for me and one that I took as a huge win. Not like, oh man, I need to spend a bunch of time thinking about user experience. I was just like, we can definitely figure this out. There's millions of companies that know how to sell things online. Like what are the odds that we're the one can't figure this out. And so yeah, most of my time was on will users think about this, like change behavior to do this? And then what are the regulations and the sort of compliance landscape that unlocks this?

Yeah. So I just talked to Eric Ries yesterday. He's the creator of The Lean Startup, right? And he reminded me that MVP, minimum viable product, was actually part of The Lean Startup methodology. And so it sounds like what you're saying is you're like, we want to get an MVP out there, even like in a shadow way. I think, you know, with Kettle and Fire too, didn't you put up a ghost page on Instagram for Kettle and Fire?

Yeah.

You didn't even have a product.

You're like, we'll go and buy bone broth if we need to. Yeah, exactly. I put up a ghost page and bought like Bing ads basically and drove them to a landing page selling bone broth. And then as soon as someone ordered, I would email them and say like, hey, we don't have any, but I'd love to know why you care about this. And you know, I'll give you 50% off when we eventually do get some. And that worked very well.

That's right. That's right. So you do your market research. So that's very interesting. So I guess I'm curious, like what advice you have for founders or really anybody who's sitting around waiting for it to be perfect before they launch? How can you inspire other people to put out an MVP into the world even if it's a little embarrassing? Yeah.

I think that the hardest thing, especially in the early days, there is this like very human desire to think that the whole world is watching you. And the minute that you launch something, it has to be of X, Y, and Z quality in order to get it out in the world. I think that way more companies die of not having momentum than they do die of like, couldn't figure out how to make a great product. And it is extraordinarily unlikely to me that someone will figure out how to make a great product just sitting in a room, you know, not talking to customers, not launching something, not getting feedback. Like, we learned so much in our first days of launching Kettle and Fire where we found out what do consumers actually care about. Like, do they care about gut health? When we first launched the brand, I was building it because it was something I wanted. I was like 26 and wanted to drink bone broth every day. Turns out that was not at all our audience. The audience was like women that wanted to get more protein, get collagen, improve joint health, and things like this. And I would have never found that out if we had just like iterated and iterated and iterated without actually talking to customers and understanding what is the value prop and what is the thing that they want. So I am such a fan of just launching something, anything, as fast as you can just to start getting the learning cycle moving.

Right. And even like, which I think is even more powerful, I just heard Keith Rabois on, I think on Lenny's podcast, and he was saying, I don't like customer feedback. And the point is, if you send a survey out, they're going to give you answers that don't make any sense. It's like if you put a landing page up and say click here, they're either going to click or not click. Like, that's how you kind of really test, test what they're going to do. That's very powerful. So wait, how long has TruMed been around now?

Almost 3 years.

3 years. So what was that early team? Because you founded Kettle and Fire with your brother Nick, but I know that Nick's off doing something else now. How did you think about your early team, especially because you're a 4-time founder, so you've done this before?

We had our first hire was our now CTO, who actually, like, when I was recruiting him the first time we met and like we're talking and all these sorts of things, he was like, I can't join, but I do want to invest. So he invested. And then over the next like 2 I just kind of kept pulling him and he ended up— Yeah. So he's on the table twice.

That's hilarious. Oh my gosh. So you had your co-founder who's no longer there, and then you had your first employee who's like, you know, again, the founding team. And was that pretty much your founding core? And then how many employees do you have now and how did you kind of build those people? Because again, there's so many different people, like early stage versus late stage. How are you now thinking about hiring?

Yeah, so we now have about 70 people on the team. We made a couple of really key hires early on. One of the people that joined that has been really instrumental to the company's growth. Growth. Actually, I wrote about what we were doing with TrueMed in my newsletter, and she was a reader of my newsletter and kind of reached out and was like, hey, I would love the mission, would love to be a part of this. And she has probably been the best hire that we've made. And so I think that really getting right the first 5 to 10 people on the team is so critical. Like that hire, for example, she's exceptional, and she has gone on to hire 10 more exceptional people at the company, you know. And I think that same with John, like our CTO, we hired an incredible humble, hardworking engineer, and he's like recruited a team of incredible, hardworking, humble engineers. And so I really do think that the biggest thing is optimizing for what are the first 5 or 10 people on your company look like, because you're basically going to end up hiring copies of them over the next, you know, 5 years or so.

Yeah, that makes complete sense. And then for your companies in particular, have to have mission alignment. I would think that's really important.

For sure. It certainly helps a lot.

Yes.

Yeah. And I was just going to ask you, like, what kinds of mistakes did you make, like at Kettle and Fire days or early in TrueMed days, that people can all relate to that what they should be avoiding.

Yeah, I mean, certainly we've made near infinity mistakes. You know, I think that as a company, we— let's see, I mean, at Kettle and Fire, I had like no idea what I was doing. It was my first company. We just made very silly, simple mistakes. Like we waited way too long. There was a period where I just didn't think that like bookkeeping and finance was important. And so I didn't invest in it. I didn't know what a CFO did. I didn't know what a finance person did. And it turns out that when you're running a CPG business, basically that entire business is managing cash flows. And so fortunately, I had like one investor advisor who I grabbed breakfast with and I was I was like, yeah, we've grown 30% 3 months in a row. Like, how awesome is this? He was like, yeah, that's great. You're about to run out of money and like, you're not going to have any cash because, you know, the faster you grow, the more inventory you have to buy ahead. That means you're paying now, you're getting cash later. And that was a thing that I just didn't know because I didn't hire a competent finance person. I didn't know what I was doing. That was one. And I would really recommend— I think finance is underratedly wildly important, and it's an area that I would hire much earlier. With TruMed, I think a learning that I have had is is it's remarkable the type of talent that you can acquire when you feel strongly about what you're doing being tied to a mission. And I have like over and over and over again, I'm very surprised by the caliber of talent that we've been able to bring on at lower pay from better jobs, like all these sorts of things, just because we were doing something that people were excited to tell their friends about, they were excited to be a part of, and they wanted to make a dent on a problem they care about. Like our CRO, we recruited, he was one of the earliest employees at Shopify selling like Shopify Plus very, very early on. And he came on, he left selling another e-commerce software company that he was like, just kind of didn't care about and came into the health world, you know, came on board as one of our like very early sales hires to really push TrueMed and like help us grow. And he's done a phenomenal job all while feeling very, very rooted and tied to the mission. One of my biggest takeaways from Kettle and Fire and TrueMed is I would frankly never start a non-mission-driven company again, like getting a startup to work is so hard that you really just need someone to feel a strong reason and a strong why as to like why they're spending an inordinate amount of time, energy working on the thing that you care about. So that's been a very, very big learning.

Yeah. How do you test for that? I mean, I think that if someone reads your newsletter and reaches out to you and kind of insists on being part of the journey, that's one good test. But when you have people coming in to interview, how do you really make sure they have this mission alignment? And then, by the way, Justin, even if they have mission alignment, which is fantastic, of course that's great, but they're sort of like not that proactive or, you know, not that great at managing projects or something, that's still going to actually be a problem. So how do you kind of think about that when you're hiring?

Yeah, I think that it's skills first. What I would say is it's extremely important in the early days to orient for people that are like 10 out of 10 on mission alignment. Our first 4 people, 5 people at the company were strictly there because they cared a lot about the problem that we were trying to solve. I think from there, like at a certain point, you're just kind of like, okay, we're hiring an accountant a finance person. It's great if they care about what we're doing to some degree, but maybe they are less likely to be hyper mission-oriented. And that's okay as long as they can do the job and there's a cultural fit and all these things. But I really do think that orienting around mission for especially the first couple hires is like a huge, huge thing that probably enough founders like— it's so hard to getting something off the ground. It's so hard getting anyone to convince them to join. I get the temptation to be like, I'll take anyone, please. But as you're building something that compounds and starts working and all these things. It's just such an advantage to have a team that feels deeply tied to the mission.

Yeah, I can totally relate to that. You know, on the topic of hard, one thing that you've kind of, I think, gone back and forth on, and both things are hard, is bootstrapping your company versus taking in capital. I know that for your current company, I think you raised $34 million from Andreessen, is that right?

In our most recent round, yeah. $44 total.

Oh, okay, great. So can you talk about how you've thought about bootstrapping over the years and what you think about it now and why you decided to raise capital?

Yeah, I think it really 100%. So I've bootstrapped about half the companies that I've started. It really depends what you want. Like with Kettle and Fire, for example, I bootstrapped the first 18 months and then it became obvious that we had a big opportunity, then raised a small seed round, then that got us to the next level and it became obvious the opportunity was even bigger than I thought. And so we raised an A. That was in 2018. We've not raised any capital since then. So that company has gotten to like hundreds of millions in revenue with less than like $10 million raised to the balance sheet. So very capital effective. TrueMed is different. Like, we, I think, have a massive opportunity here. And I think what I felt starting out was there's some way in which starting a bone broth company or a company in CPG, you're like limited by the market size to some degree. And, you know, it'd be hard and kind of risky for Kettle and Fire to pivot into tech or something like that. Although Allbirds is now a data center company.

Yeah, exactly.

Exactly. But something that I felt very strongly is like, okay, TrueMed is going after one of the biggest problems in the country. Country. We are at the intersection of a lot of different tailwinds, and I really felt like I wanted to work with the best people. That's what made my job fun. That's what makes my day-to-day enjoyable. And I want to go after a big mission. And so in my view, if you are wanting to hire exceptional talent, you want to go after a big mission, you want to try and make like a big splash, it is really tough to bootstrap a business that satisfies all those criteria and remains bootstrapped. Like many of the discussions when it comes to bootstrapping a company are like, how do we trade off this scarce resource, which is cash, and still try and achieve as much as we can, you know, using the very, very limited resources we have. That's fine. I think that's probably good financial discipline. But almost never are you able to say like, hey, I want to overpay this amazing person because they're mission-aligned, because I think they're exceptional. I think they're going to be the best possible person to take us from here to there. You know, and with Trimed, I wanted to do that. I wanted to build the best team around us that we could. That required in many ways paying like high-end, you know, top-of-market salaries to get the best people. People. And that, I think, felt like the right trade then, and like, I think certainly has been the right decision.

And how do you feel about now having venture capitalists on your cap table, and kind of, you know, how that changes what you need to do in some ways? I mean, it's sort of a— I hate to call it a treadmill, but it's kind of a bit of a treadmill about what your expectations are that you're venture funding a business.

Yeah, for sure. I mean, it changes expectations. Now, that doesn't mean that you have to change everything. You know, these are investors, they don't really want to run your business, especially at seed and series stage, like they don't really want to run your business. They don't really want to fire you, assuming you're doing a competent job and you still have control of the business. And so I think that there is totally a world, although I don't expect it, you know, if we wanted to, we could tell our investors at some point in 5 years, hey, the prize isn't as big as we thought. Here's what we're thinking is the right path forward. What's your thought here? Let's get off the treadmill. Let's build a profitable business. Let's like do this and build a very valuable asset. And they will be fine with that. I think that it is important to align expectations. I think it's very important to feel like, you know, we went with Andreessen Horowitz. We felt like they gave us the best chance to really win and win big.

Because they're such a big name brand, or is that why? Like, why was that?

Partially because they're a big name brand and partially because I think that they have a long history of working with companies that operate in regulated spaces and helping them. And so that was a big thing for us. And I think at the end of the day, there are some things you have to put up with that from an investor that are not as fun. Like, you know, I wish I was a bootstrap thing at certain times when you're doing like financial reporting or whatever. But at the end of the day, I think think that the set of tradeoffs was totally worth it given what, what we got.

Yeah, that makes sense. And then what have they brought to the table that is above and beyond capital? Be honest.

Yeah. So a couple of things like a VC's job is basically to constantly survey the market and understand what is going on. Like in today's world, you know, it's May 2026. We are getting a lot of intel from them around what are they seeing from other telemedicine companies? How are healthcare startups leveraging AI? How are healthcare companies selling into large insurers organizations, selling in hospitals? How are they thinking about raising money? Like, what is the market clearing price for a Series B company? At what point should we start? You know, what are the metrics that we need to hit before we go out and do our Series B? They've also, in our case specifically, made a lot of introductions to extremely key individuals that are very relevant in our space. Like, there is a real way in which, you know, I as the CEO of a bootstrap company can email a public company CEO and will probably get ignored. Whereas like a board member who does healthcare investments for a $60 billion under management venture capital fund, you know, Andreessen Horowitz, he or she is going to be exceptionally well connected with a bunch of the players that over the next 1, 3, 5, 10 years, we need to have our ability to move into a space like healthcare where I have no background. I didn't have any relationships. In many ways, I like, you know, I'm still figuring out the space and we can get very, very good meetings with some excellent people who are very well connected connected in healthcare in a way that like really benefits the company. That's one of the very like useful things.

Yeah, that's amazing. And I can really understand what you're saying, especially around those introductions, which is like me, nothing, but like someone from Andreessen Horowitz, people pay attention. Now, as part of what you said, you just gave— you just said one of my bingo words, which is AI. And so you started your company 3 years ago, kind of on the cusp of like AI being a thing, kind of right then that moment. And now I guess I'm just curious this. So a lot of founders right now who started their companies pre-AI, so 2020, 2022, even whatever, they're going through an AI transformation moment. I'm curious what you're doing, seeing, thinking about as it relates to AI inside of your company.

Yeah, I mean, so we are in a very fortunate position, which is we have a bunch of runway, a bunch of money, we have a great team, we have some product-market fit, but are still fairly early in our journey. And so 70 people, you know, I would say that we're at a spot where we are like, great, we started figuring out how to embed AI AI into our daily workflow and how to build it into how we operate as a company. You know, we had like 25 people, 30 people. And so we have a lot, like our entire engineering team is shipping code using AI. I have a chief of staff who his sole mandate is figure out how to use AI internally to get more leverage for everyone on the team, teach people how to use Claude code, all these sorts of things. We've built internal tooling that allows everyone at the company to build and ship like production-ready code, build internal tools, build things that help them solve like very immediate business problems that they have. I think that one of the things that has historically been true and is becoming less so is that people broadly have been, you know, like people have these desires for building internal tools and improving those and whatever. And those always, always, always slip to the bottom. If there's a customer-facing roadmap versus like improve my internal dashboard or something for a support person, like that almost never makes it to the top. Now, like we've spent some time building our internal infrastructure. And like we have our director of operations is shipping product that is making his experience of running and operating the company much better. That is, I think, a fairly novel thing and something that we're like very big on investing in.

Yeah, that's amazing. I love that. And I love the idea that like you were pretty small when AI kind of took over the world a little bit. So you were able to do that adaptation. What advice do you have for founders and also people in general about things that you have discovered inside of your company That's not just sort of domain related, that's sort of generalizable to everybody about how AI can make people more productive. Like, what has your chief of staff kind of discovered about how to help people?

I think one of the biggest things is, especially as you become a company of like 10+ people, it is important to understand how can you best get leverage out of these tools. For us, that meant like we first started by being like, great, chief of staff, like meet with all team leads and let's figure out how to apply AI across a bunch of their problems. Problems. That was moderately useful, but actually not that useful. Where I think we really started to see benefit was once we built internal tooling that allowed anyone at the company to ship code, to launch something on this internal tooling, to get it actually like working in production, but also to get it working in production and not take down our entire website, not take down our database, like all these sorts of things. And so there was this tension between engineering and, you know, engineering product and the rest of the team of like they wanted people to ship code, but they also didn't want to like manage and, you know, inspect and have that be a drag on their overall productivity. And so a big thing that we did initially was just making sure that we have stable infrastructure that allows individuals to ship internal tools quite quickly. And then beyond that, you know, allow people to build stuff. And that has been a very, very useful thing.

Have you found that people are eager to build stuff once you kind of show them the way?

100%. If you're hiring the right type of person, I think everyone Everyone wants to solve problems, and like, there's 10 million things about everyone's job that can probably be better or less annoying, you know, or whatever, that if you can— like, if you have a full-time software developer, i.e., Cloud Codex subscription, pretty insane tools that, you know, I wish I had when I was starting my career. And so it's been remarkable to see a bunch of people really lean in and learn how to use them.

Yeah, that's so cool. Now, another my bingo words you brought up earlier was maha. So, and by the way, I'd also want to say about the cereal, on the one hand, I agree you. Of course it's better not to have all the red dyes that make kids autistic or give them ADHD or whatever. Of course. Nonetheless, also cereal is not good for you, right? So, so I want to just kind of ask you about what your thoughts are about the sort of the new healthy movement in the US. We sort of call it Maha. It's kind of a lot of different things. It's kind of across party lines. What do you think is good about that push for, you know, more health? And, and what do you think is really falling short?

I mean, I think everything about it is good, frankly. Like, I think that if you look at healthcare costs, you look at healthcare outcomes, you look at longevity, you look at almost any of these things, we're like among the sickest countries in the world and we spend more on healthcare and have worse outcomes than any other nation. That is like fundamentally wrong. And I think that a big reason that we are in such a sorry state is we have lifestyles, we have a food system, we have all these things that do not promote human striving, do not promote a healthy, happy human. And so I think that the focus on health in general that people are now calling Maha. It is like a renewed focus on the fact that the chronic disease crisis is the biggest problem in the country today, in my view, short of maybe like nuclear war or something like that. It affects almost every American. It impacts our economy more than any other issue. And I think that there is like, correctly, an awakening, and people want to have the conversation around why are we having more kids that are obese, why are we having more kids with ADHD, why are we having more depression, more anxiety, more infertility, like all of these things that are happening at record levels. And so I think that the Maha movement fundamentally stems from that desire and that question of like, why is everything that we're doing from a health standpoint both so expensive and not driving good results?

Yeah, I mean, I think it's such a complicated question, obviously. I think one thing that I think a lot about is sort of pesticides, which somehow we have to, you know, not have bugs eat our foods and whatnot, but these pesticides are so bad for us, why are they even legal? I mean, these conundrums, but I'm not sure if they're getting solved. I feel like they get solved at the community level and also individual making choices. Do you feel like this movement is solving them, or do you feel like— tell us your point of view on this and what can bring us hope.

Yeah, I think things like pesticides are tough because on the one hand we have a food system that for decades has used pesticides in great amounts to grow most of the foods that Americans eat today. I think it is probably both true that pesticides contribute to negative health outcomes in a pretty serious way. I think it's also true that if you banned pesticides, that the cost of food in the US would probably go up like 30 to 70%, depending on what you're talking about. And so it is like really a political conundrum. Like, I think that we do not— unfortunately, we don't have that many issues that are so obvious. Like smoking, everyone smokes. Smoking causes lung cancer. People just stop smoking and you're fine. Maybe we have that from a processed food standpoint. Like, I think that you're in the early days of seeing a large percentage of of the population just decide not to eat ultra-processed foods, eat seed oils, eat like things that are super high in sugar, all of that. And that I think is great, and like consumer choice should be there. My problem with a lot of the arguments for consumer choice and whatnot is when it comes to things like pesticides, when it comes to things like having an agriculture system that outputs crops that are 30 to 60% less nutrient dense than what we had like 40 years ago, that's where I think no one can look at a label and see what pesticides were sprayed on buy, like, box of cereal or Apple or, you know, ground beef or whatever. And I think that it is in those areas that the movement has the opportunity to drive transparency and drive more regulation that allows consumers to make informed choices. And once you make informed choices, I think, like, the direction of health will move in a better direction than it is right now.

Yeah. And in some ways, it's almost like the economic, you know, sort of capitalism as a model can't show up if people can't make good choices. And then people can make choices, informed choices, and then kind of the capitalist market can kind of move around that based on what people actually want.

Exactly.

Yeah, I can see what you're saying. Now, Justin, another interest of yours seems to be community. I saw that you're involved with something called— wait a minute— Esmeralda. Yeah, tell me about that. I'm obsessed with community these days.

Amazing. Yeah, so my wife actually co-founded Esmeralda in a company called Edge City. Yeah, and so what they're basically doing is they are building building, she like correctly intuited that like one of the biggest problems, people feel lonely, they feel disconnected, they feel like they move to a big city or they leave, you know, where they grew up and they're like, don't have a deep-rooted sense of community, of belonging. I think that is true for the average person. And that is even more true for many individuals that are like into fringe things. Like if you are into some edgy topic or like a thing that is on the frontier, like brain-computer interfaces or, you know, I don't know, any number of things. There's not really a place that you can go to hang out with other people that are into these types of things that you are. And so what they built is at Esmeralda, it's going to be in June in Northern California. And what they basically built is this like month-long get-together, about 1,000 people kind of come through. And there's different weeks of like on health and longevity, which I'm actually running, you know, tracks on consciousness, on brain-computer interfaces, on crypto, on like charter cities, like a bunch of things that are sort of new and frontier and very, very interesting in a beautiful place with a bunch of very cool people. It's a great time.

And is the vision for this to actually turn it into a full-time village?

Yeah, yeah. So Edge Esmeralda is sort of a collaboration between Edge City, which is a company that does these like 1 to 2 month pop-ups all over the world. They do these like, you know, 1 to 2 month co-living experiments. They did one in Argentina last year and then the one in Northern California. So it's that collaboration with Edge City, and then, which is a new town that is being built basically an hour and an hour and a half north of San Francisco that is in process getting permitted, you know, has raised money and is like in the process of literally building a town for, I think it's like 600 homes or something like that. So it's very cool. I think that it is a thing I'm very interested to follow along and bullish on to see these people kind of building the society that they want to exist, the communities that they want to exist. And in Edge City's case, their goal is to like build a network of, you know, many tens of thousands of people. And as they build and, you know, that network compounds, towns, then they can go into different communities and say, like, build a more permanent structure or a more permanent town and these kinds of things. So it's very cool.

That's very cool. I love that. I do think that, like, health is having a moment and community is having a moment, and so maybe it's not a surprise that you're, like, involved in both of them. Yeah, that's so cool. Now, Justin, over, like, a long career— and you've had now, what, a 15, 20-year career— there are always these highs and lows.

12 years.

Yeah. Is it really? Really? Gosh, you're so young.

Okay.

Yeah. But you've done a lot in that period. You've had highs and lows, you know, especially as an entrepreneur, highs and lows. What are some of the highest highs you've had, and then what are some of the lowest lows you've had as you've been building your entrepreneurial kind of career?

Yeah, it's funny actually, like looking back in retrospect, for example, Kettle Fire, we had a lot of wins through the period of building and growing that company. Almost all of the things that I remember most fondly that are like the highest highs were like like things that we did as a team, either a team retreat or like working through a hard problem, having like a really fun time and getting together with the team when we were like sub-20. Like it was the moments that at the time just looked kind of normal. But those are like the things that are very, very high, even more so than like, oh, I remember when we got Whole Foods National or we closed our funding round or any of these kinds of things. That's like a thing that I would say is always surprising to me is that when you look back on these things in retrospect, it's often than just like the people you work with, the problems you're solving together, and the experiences that you have always end up being like the highlights for me. From a low standpoint, I mean, running a company is hard. I've had to— probably most of my lows have been either feeling extremely uncertain around a decision and that causing stress, having to fire or part ways with people that, you know, were friends, are friends, people that had like given a lot of their lives and energy to the company when just getting to a point where it didn't make sense for the company anymore. Like, there's a lot of hard decisions that go into building something successful and something that works and a team that functions at a very high level. And making those decisions has often— like, those are the things that have caused me some of the biggest stress and that have been frankly just lows. Like, it sucks to like part ways with a friend or things like this.

It does suck. By the way, parting ways with a friend is, especially if they've given themselves to the company and whatnot, is actually very hard. Can you think of an example and how you actually came to the moment of realizing, I have to part ways is terrible.

I think in many cases it feels obvious. In my case, my wife is very perceptive and she like does a good job of just reflecting back to me like, hey, you know, for several weeks, like you've thought about this. This has been a thing that has come up in our conversations. Like maybe you should think about what to do here. And so having like some reflection time, whether it's an executive coach, you know, a partner, I try and take an afternoon off every month and just kind of like put my phone away, think about big problems. Problems in the business, think about what's not working well, what's going well, and having those kind of rituals that help with reflecting and realizing maybe what's not working and what's going well. Yeah, but I probably, because I don't want it to be true, I probably move like 1 to 2 months too slowly on many of these decisions, unfortunately.

Justin, honestly, if you move 1 to 2 months too slowly, which I don't necessarily believe, you're so far ahead of most founders who usually take, as you know, a year or two to make these hard decisions, right? It's just very— they're very hard. And I think we all do this telling ourselves, oh, maybe it's not true, or today was a good day, or kind of whatever.

Yeah, for sure, that we go through.

Yeah, yeah. So do you have any advice? Do you have advice for people?

I think that one of the things that is very helpful is just going through it once and then getting onto the other side and being like, wow, the company didn't die. You think that the team is going to freak out, that everyone else is is going to quit, that your investors are going to be like thinking, what are you doing? And none of those— like when we were raising our Series A, we had a term sheet from an investor. It had not closed. A big reason they were investing is because we had hired the COO from a very high-profile consumer brand and gotten them to join. And between hiring him and going through the Series A process, I basically had decided that he was actually not cutting it and was not doing a good enough job. But he was the best name and brand that we had at the team and like a big reason reason that the investors were investing. So I thought, and so I thought this was just an incredibly challenging thing. I thought the team would think I was crazy. The investors would think everything. And we parted ways with him and the investors, rather than being like, oh shit, that's bad for us. They were like, I'm impressed. You made a hard decision. Like, I think it's probably the right thing if you feel it is. The team was bought in. We messaged appropriately and it just went from this like massive thing in my mind to being much less of a big deal. And I think that is the biggest lesson is like all these things can feel like company-ending, biggest problem in the world. One of the benefits of experience is you do this a couple times and like I have a much stronger belief now that things will just work out. And like we could let go of many, many people on the team, though I obviously don't hope to, you know, and things would like tend to work out okay.

Right, it's not like you're hoping to, but it just makes you realize that you're not stuck. I think that's what's important.

Exactly.

Yeah, that's very powerful. You know, one thing you just talked about was having uncertainty. That's very normal. And you're like, what should I do? And when you're founder, there's like no playbook. There's no one to tell you what to do. There's no kind of well-trod path in your particular business. So have you ever suffered, or do you suffer, from imposter syndrome or severe self-doubt?

Yeah, of course. Yeah, certainly. I mean, I think every— I don't know, maybe not everyone does, but I certainly do. I think I want to build something that is important. I want to build a great company, build a great team, work with people that I enjoy. All these things are frankly very hard to do. And so in the day, it's up to me to make good decisions, recruit the right people, invest appropriately, all these things. And so yes, I definitely, definitely struggle with that. And yeah, it feels hard.

So yeah, of course it feels hard. Absolutely. So what do you tell yourself, or how do you get yourself— what advice do you have for other people to kind of handle their own self-doubt? Because as you point out, many people have imposter syndrome.

Yeah, I think that almost always doubt is a function of like thinking about some point in the future. Almost never am I in a situation where today, this moment, I'm like really really like doubting what am I doing today? You know, it's always kind of like for future thinking in some way. And so I find that when I struggle with that, it's really useful to just find an area of the business and move from this like abstracted, where is this going? What are we doing? You know, whatever, into like a much more tangible problem that we have today. And if you can go from what do I do? I'm kind of doubting myself, which is frankly a bit paralyzing, at least for me, into here's a problem in the business. Let's just focus on this, solve this problem, make the product slightly better, serve our customers slightly better. I think if you can just do that, it creates a lot of energy, it creates a lot of focus, it creates a lot of like, you know, the team feels good about solving problems that are right in front of them. And if you just add that up over the course of a couple of years, it turns out business is just solving problems. And so if every day you're just waking up and you're just like, I'm going to zone in on one problem that's very obvious. What's the biggest problem in the business? Let's go solve that. You know, I kind of like took that approach with Kettle and Fire, and one day I woke up and it was a big company with a lot of people. And you know, you're like, okay, that worked, I guess.

That's right, that worked, I guess. Justin, what's it like to have more money, to have kind of a lot of money, and how has that changed your life or the way you run your business?

It doesn't— like, from a business standpoint, like having a lot of money in the bank?

Well, just you, you personally.

I think it doesn't really— it depends. It changes some things a lot, but most of things, like, doesn't really change. You know, I think that for the most part, I still have many of the same friends, we do many of the same things. I think that it's a really useful exercise if you can, to early in your 20s— I had the experience of living and hanging out with a guy that I was working with from a career standpoint who was very, very wealthy, and I got to see, like, what is the life, like, the inside life of someone that has a ton of money. And the answer was it was very similar to my parents' life, but things around him were a little nicer. And like, that was basically So yeah, I think that money solves money problems, but most of the things in life are not money problems. And so I think that it's been a tremendous gift in many ways. It allows me to be generous. It allows me to like buy back my time and only spend time doing things that I want, you know, but those are like the main benefits. There's this quote, I can't remember who said it, but someone said like the reward for good work is like more work. And that is how I feel. Like I'm not working on TrueMed for more money or more anything. It's just, I like what we're doing. I think it's important and I really love the people I get to do it with.

Yeah. Well, I think especially for a successful founder, doing it again is really— actually, I just had Jyoti Bansai. He's from Harness and he sold his company, his first company for $3.1 billion to Cisco. And he told me, yeah, I went on sabbatical and I did my bucket list. And my bucket list was like 6 months. And after 6 months I was like, well, what the heck am I going to do now? And he was actually sad. And he was like, well, I obviously need a mission. So he kind of, you know, volunteered himself to go back into this, you know, the startup world. And I think it just sort of revealed preference, right? When you start another company, you don't have to. It's like, well, I guess I'm a builder.

Totally. I also think that the type of person that can build a $3 billion company is probably not the type of person that like can happily live on a beach once they have X amount of dollars in their bank account.

Totally.

That's a good point. You know, I think that for me, after Kettle and Fire, like had this feeling of what do I like doing? And in most cases, that is not like playing tennis and going to lunches and hanging out with friends all day. It's like the times that I've most been happiest in my life, I've been working hard, orienting towards a mission, making sure I'm in good health, making sure I have good friends. Like, those are important, but the most rewarding and like energizing times in my life were not when I was doing nothing. It was when I was like working hard at something that I thought was important.

Yeah, totally. That's a good 3-day weekend— playing golf, playing tennis, right?

Exactly, exactly.

Life, right?

Exactly, exactly.

You know, just Just a couple of more questions, Justin. What do you wish you had known earlier on your journey?

I think for me, a consistent thing is learning to— like, I wish that I had known that it is okay for me to kind of trust myself and my judgment and make my own calls. I think very early on, and still today to some extent, I will look to other people for advice and thoughts and all these things. And really, what— at the end of the day, it's up to me. I should like make my own calls. So often I think learning to trust my judgment has been a very positive positive thing, although a hard thing to get used to.

Yeah, and something you have to relearn every day, every week, right?

Definitely.

Yeah, totally. And last question, what advice do you have for other founders as they embark on their journeys to grow into leaders?

Good question. I think the big thing is so many people get caught in this loop, at least I do, of thinking like they have to be perfect, they have to have the right idea, the right thing, you know, oh, I need to start a thing that is on trend, that can be worth $1 billion, that's in a space I'm passionate about, that allows me X, Y, and Z from a lifestyle standpoint. I think that figuring that out from a dead stop is insanely hard. You know, I think it's nearly impossible. I wish that people would realize that so many things, like for me, Kettle and Fire started because I had a random idea. I did the quickest, easiest thing I could do, which was put up a landing page, buy $500 of ads, and that started the whole journey. And I think that people just should internalize that startups are frankly just momentum games. Like, if you can just get started, you start to feel the momentum, you get pulled into something. As you get pulled into things, you start to see other opportunities, you start to see how it can be bigger than you thought from the outside. Like, in everything that I've done, I've basically gotten into a space that looks like it might be small and then worked really hard to make it bigger. And I think that, at least for me, that is something that people probably underestimate. And I think that frankly, it's just get started and, you know, build something great and then work to expand it from there is an underrated strategy.

I love it. It's really iteration. Build something, iterate, iterate, iterate all the way to the end.

Yeah. For me.

Amazing. Justin, thank you so much. What a great conversation. It's gonna help a lot of people and I really, really enjoy talking to you. Thank you so much.

Thank you.

Thanks for listening to From Startup to Grownup. If you like what you heard, give it a review on Apple Podcasts so other people can find it. And if you know of a founder or someone else who is meant to be on this podcast, drop me a line through my website, alisacohn.com.