From $0 - $1 Billion Company: How this Founder went from suffering Migraines to Building in Nutrition

26:18You know, if your view is that it's happening to me, to your point, like instead of, you know, what can I do in the situation? Like I always struggled with the people that would come to me and be like, well, you know, I tried, but I can't, I can't figure it out. I'm like, what are you talking about? Like, I'm not going to do your work for you. Go do stuff. Have agency, like you said. I think that attribute or trait, whatever you want to call it, is maybe some people get a little bit better over time, but I don't think if you don't innately have it that you will just gravitate there. There's like something, and we meet these people and now you've met them and there's There's a different spark that these great people have than the other ones.

27:12And I will also say that depending on the company, what's not a spark at your company could absolutely be a spark at a different company. Like I think about a lot of folks that we hired who were really successful at Apple, for example, but then would come to Netflix and be terrible. Right. But they were amazing at Apple. Right. But it was just what that thing was, the je ne sais quoi, I don't know, at each company, what was different. And so it doesn't mean that they're not great. They're just not great in your context. Yeah, exactly. Yeah. It's a hard thing to do. I think that kind of comes back to some of what we talked about earlier on.

27:54Having that kind of conviction or taste in the type of team and the type of culture you want to build is then in the interview process or in evaluating team members. like um yeah you can you can understand what works well at your company or with that team or with that manager with that leader um that might not work elsewhere because um yeah you know if i if i think about you know a lot of the you know the best teamers we have who've driven forward you know amazing results like it's not always like perfectly clear sometimes it is from the resume but sometimes it isn't and so it's also we do a lot of kind of like we just did our kind of 2025 recap 2026 planning and we're kind of doing some more just like retro on on on the folks that you know have succeeded the most and what are their kind of what are their qualities or skill sets or or whatever and it's often it's very humbling because you realize like how hard it is to predict as as a thing you have like a less of a hit rate then if you ask a manager when you're making the offer like what how do you think this person's going to perform in like 6-12 months like i think it's uh less easy to predict than most people might think and that's a hard thing because it it's humbling because it is it's the skill that probably i would most want to have buying like uh undervalued talent is like maybe the most important skill to have is just a yeah it's a it's a really hard thing to do and you know like we talked about earlier like if you can do it it's it's the highest leverage thing and it's often again like really humbling where maybe you'll be working on something like i'll be working on something i'll be banging my head against the wall and i made some progress in six months and then i hire a great person to that role and they make more progress in their first like two months than i did in six months or someone else on the team did in six months and you're you're like really like oh my god wow i'm like really lucky to work with you and that you were willing to work for our team and our mission and so on, because talented people obviously have a ton of options of what they can do with their time.

29:35So when they committed to your mission and your team's mission and they really make a difference, it's like there's nothing you would rather do than, A, retain those people at all costs, but B, go try to find more of those people, which is a hard thing to do. Yeah, no, it is incredibly hard. Well, you mentioned you have some questions that you use to identify. so what what are what are these questions that you ask in the interview i'm i'm curious so i've had this this notion pay we use notion for everything that was like kind of my my i it's like my values interview if i'm a hiring manager on a role it's uh it's a little bit different but i do i still try to interview almost everyone in the in the company who joins although not able to do that anymore and my co-founders and i split up all the the final rounds but i've kind of been iterating on it for four years essentially like what questions work and and what don't so i think one i like i'll start on the one we talked about around cherishing feedback and you know i talked about that's important um i like to ask about like the number one thing they're working on improving at professionally going forward and i find that's i find if you like ask someone like what are your weaknesses or like mistakes you've made like you can get value out of that but like they often kind of know how to do the like quiz the answer to be a positive thing thing and which which is fine.

30:53But I think the higher signal is like, I'm basically trying to get at what I described earlier of like, is someone self-aware about like the gap between where they are today and where they want to get to? And I found that's the highest leverage is like, basically a great answer is like, they cite something that actually is a real weakness and an important thing. Like, not like the Michael Scott, like, I work too hard. Yeah, basically. I'm such a hard worker. That's my biggest weakness. Yeah, exactly. I care too much. And then they're actually able to give kind of like tactical examples for how they're looking to improve at it.

31:19Because basically like skill development is a meta skill like you can actually get a sense of like like it's one thing to be self-aware which is important and understand it but it's another thing to actually like to improve like it's a hard thing to do and like even if you just like read about the best people in like any field or an athlete or an artist like a lot of what they're doing that makes them great is kind of those like very deliberate like unsexy you know it's like the swimmer is working on like their flip turn like a thousand times a day it's like so you're kind of trying to get a sense of like or like a pianist is like working on their scales or whatever like you're kind of trying to get a sense for obviously it's different on different roles like do they have that sort of like natural curiosity and like self-awareness and way of deliberately improving so i like that one i really like asking more about feedback that they've had to give others um if it's a manager it's like you're getting a sense for like their their manager skill set but if it's like uh if it's an ic it's almost even higher signal because you get a sense for like oh are they are they willing and able to get feedback upwards sideways cross-sectional influence even though it's like maybe not necessarily a part of their role and then you also indirectly get a sense for kind of like what they it kind of like shows what they care about like if you're giving someone else feedback on something to improve like obviously you're kind of saying like i think you need to get better and this is an important thing and so you kind of get that one uh really indirectly and yeah i really like that one and then maybe the last one that i think you get both kind of the cherishing feedback and more like overall first principle strategic thinking which is something we look for is you can essentially ask someone i like asking basically like what would you do differently in your current company if you were the ceo like if you had the magic wand and and you could do anything it really is obviously like strategic thinking because you're basically asking them like how would you run the whole business that you're a part of but um you could also build built into the answer and if i don't get it i kind of ask a follow-up so you can see like did they do anything about it like kind of getting at the agency part we talked about like okay you just said like that was the biggest mistake the company's making it's the most important kind of thing in the company like have you done anything about it or told someone about it and like yeah i think you get a lot of signal from that one too so yeah those are a few of my favorite ones that we've done yeah no i love i love i love those and yeah you i mean you know you learn you learn this over time and i think uh and i'm not realizing if people watch this they're gonna get my questions we'll see i know you're gonna come up with if you prep that if you prep that well by finding this I know, right?

33:39I'm sure very few people will. We have a big, big community that listens, but, but, you know, you never know. Somebody may be interviewed like, I got your questions, Aiden. But I think like, you know, the trick with interviewing, and this is what I was trying to coach people on is that you kind of are like a detective, right? Like, and I think a lot of times people ask these questions and then they're okay with like the surface level, like answer, right? But they're not like pulling in on the clues and like dig it. Well, why? Tell me more about that. Why did you make that decision? And who did you make the decision with?

34:20And what were the circumstances? And you just kind of keep digging. And so there's no right or wrong question to ask. But I think you have to keep going as far as you can go so that you do understand how they're thinking. And not just strategically, but emotionally. And there's so much. But you never know. Even if you do all those things, it's always a bet. AI has not figured out this hiring thing yet. Yeah. Yeah, no, it's interesting. I mean, it's back to what you said earlier, but we were talking about the importance of like the talent evaluation skill set, I think. Interviewing is one of those things, you know, I talked about like how it's humbling, like when you make an offer, how well you could predict, like how well that person performs.

35:05I think probably if we have the data, which probably we should cut the data of like what you said in your scorecard or your yes, no recommendation and like how that person, I'm sure it's equally as difficult. And I'm well aware of ones that I've had false positives and false negatives, both of which are painful. But I think it's an interesting tension between like, on the one hand, as you scale it back to like the conversation about operating system, like you do want to add some more like rigor and sophistication to your interview process. You want to have clear competencies you're testing when you kick off a role and like a template for the kickoff document of what you're looking for and what the ideal candidate has.

35:38you want to tie your kind of people on your interview panel to different competencies and like give them a sense for the questions they should ask to standardize it to be kind of like you know fair to everyone and try to get the best signal but on the other hand there is a huge art to it to your point and there is a je ne sais quoi and i don't know how my pronunciation was

35:59but that you want to leave space for yeah maybe the competency you're testing is whatever their manager skill set but like you have a 45 minute interview and you realize pretty quickly on like actually they they're pretty good at that but what i'm really worried about is like insert other thing and so actually probably the best use of this time is to go really deep on that thing that wasn't on the kit but like yeah it's kind of a natural tension between like standardizing and scaling it with also kind of like leaving room for the art part of the art and science and the intuition part of hiring that um is a hard one but uh we try to kind of leave space for in the in the process.

36:32Yeah. And I think, you know, to your point, you do as much as you can to figure out, you know, asking all the questions, digging, you know, looking at the validating, not validating. But at the end of the day, you're a human hiring a human and you're going to make mistakes. And so I think you have to be equally aggressive on the back end as you do on the front in when you get it wrong and be honest about that. But, you know, I don't know. I wish, I'm sure you see this with your team and the leaders underneath you, but there's almost a myth with managers that having somebody is better than having nobody.

37:12It's just not true. We were literally just having this conversation as we're doing 2026 planning of that. Those are the hard ones. I think if it's a clear mistake that you made and it's very obvious it's not a fit. Everyone's, or not everyone, but most good companies are pretty good at kind of correcting and those mistakes. It's a very obvious decision. And then if someone's amazing, it's pretty obvious, like give them more responsibility. And yeah, it's all the people in the middle. It's the middle and like really differentiating between like, there's a part of the middle that's like, if you have a really high bar of talent in your company, then the people in the middle should be great.

37:42And that's like actually great and okay. And like, you want to reward those people and have them retained for a long period of time. And there's some people in the middle who will become your top. And that's like, obviously even better. But there's some people in the middle who will just like stay in the middle and that's that also is actually okay i think you basically have to have to differentiate between like the middle of the middle and the bottom of the middle essentially and like that's kind of where we where we have yeah can they move up yeah and if and if you don't have conviction that they can move up like obviously these are hard conversations but it's it's the right thing to do it's it's what i would want is like i would want someone to tell me because to your point earlier like they're that person most of the people everyone we hire is like you know very talented like i truly believe that they can succeed in a lot of different places it's just It's like, it wasn't the right role.

38:23It wasn't the right company. Whatever it was, you owe it to them to kind of like get to that decision more quickly and not kind of dance around it or do these kind of like, you know, putting off the decision. And it can be painful because in a high growth startup, like it does feel like something is better than nothing. And often, sometimes it isn't and you're just being hesitant, but like sometimes it legitimately is, but you still have to force yourself to kind of have those hard conversations sooner because I think ultimately it's kind of like it gets you to the best overall answer faster and and there's a lot of addition by subtraction and it kind of almost like forces you as a team to address the problem and say okay now we have a hole on the org chart like now we need to fill it or switch people around or hire a great person and almost like forcing yourself to have that conversation sooner rather than like oh this is fine for three months and then three months turns into six twelve eighteen and now like the opportunity cost of what you could have achieved with someone amazing is like massive.

39:18And so I think that's the hardest thing to do well that we're trying to get better at. But yeah, it's really not easy because you have to kind of, we do one to five for performance ratings. Like it's really fuzzy. Like what's, what is a two? What is a three? What is a four? You know, it can be hard and roles are really different. And so you kind of just have to like be very clear with managers and the team about these sorts of frameworks that you and I are talking about, which honestly is something that we still need to get a lot better at. I don't think we're great there yet. Well, if you want some help, let me know.

39:46I will. I'll help you. I have one last question for you before we kind of get into the ending of the show because we're running out of time. But is being a founder what you thought it was going to be? Do you get lonely? Like, how is it? Yeah, that's a good question. You know, I honestly had, I almost like had so much. You don't know what you don't know. Like, I had so much of that that I don't even know what to think of it. Like I was one of those like weird people who I feel fortunate about this, that I did for a reason when I was growing up, like have an idea of what I wanted to do. And obviously when you're young, you don't really know what that means in practice.

40:23But like, you know, I grew up with, you know, my co-founder Sam and we always had kind of different side hustles that were entrepreneurial. And then, you know, my other co-founder Stephanie through Sam, they went to college together. And so we always kind of were like hacking on side projects together. And it's not like I had a perfect plan of like, I want to do A, then B, then C, but I kind of did know what like C was, you know? and so like i i always felt like i i didn't know if it was gonna be one year into my career or 10 or or whatever but i did know that i just i really don't like didn't know what i i didn't know um like it's i think everyone always says this but it is true like it's much much harder than you think it's going to be and that's kind of like a healthy thing because it causes you to be willing to do this i'm sure i'll feel the same way in like three five ten years and i think the part that I didn't fully appreciate to your question is, um, there's obviously a lot, a lot of hard kind of like tactical things and skills you have to learn, but at least I found for me personally, like the hard thing is kind of like managing your own psychology.

41:23Like the highs are high, the lows are low. And you know, if you're not careful, I found that that has gotten to me at times and whatever you want to call it, like stress management or like, um, whatever it is, like, I think it is a really important skill that, um, honestly I really struggled with for, for a while, I would just kind of like, let it get to me. And I think I've gotten better at that. But I still have, you know, a lot of room to improve. Funny enough, it's very ironic for obviously the problem we're working on in our mission is I found the highest leverage thing is actually just taking care of my health, you know, my nutrition, my sleep, my fitness, meditation and mental health and, and so on.

41:58And again, ironically, at times I have like let those things slip while working on the healthcare company and the mission that is that but I think I always just try to when I'm feeling that kind of like return to the basics and really focus on those things. I often find like, you know, taking care of those things for a few days often makes all your problems seem easier, especially as the company scales. Like often what you're doing is just you're trying to like make a handful of important decisions. Well, you're trying to attract and retain, you know, the the best people and you're trying to like, you know, you know, lead people in both the kind of like tactical, but also the subtle things towards like your your mission and vision i find that if you're not showing up like with your best self you know mental health your best physical health like that's just a lot harder to do and um you're kind of shortchanging yourself and so often back to like high leverage things that we talked about those the high leverage things but honestly it's hard and it's like a it's a constant thing and i have a lot of obviously there's many levels and orders of magnitude above of what we achieved and we hope to achieve.

43:02And I really, I really respect the people who have achieved those things because I do realize how hard it is. And I know it only kind of like gets harder. And I think that's a lot of what we coach the team on and leaders on our team too, is that one of our values is have that dog in you, which is like a fan favorite. And that's really what it's about. It's just kind of that resilience and running towards hard problems and kind of like, yeah, managing your own kind of psychology through challenges. It's important, but it is hard. It's been the part that I've, I think, come to appreciate a lot more doing it.

43:33Yeah, no, thank you for sharing that. And I think, you know, a lot of founders, I think, struggle with this. And because there, I mean, there is just an enormous amount of pressure, right? Like you have employees, you have investors, you have customers, and it's kind of all on you. There's nobody, I mean, you're lucky that you have some co-founders, right? But there's really nobody else that you can talk to about some of these things. And so I think it can get overwhelming and lonely. And I'm glad that you are taking care of yourself because I think that that's a lot. Because again, if you're not, you're not going to show up to these things well.

44:16So I'm glad you're doing that. And you can use your product. Yeah. Yeah. No, exactly. It is always helpful. We talked about the culture as a product and I am, I'm a user of the product. I work at the company. And so I can learn from that. And I like, but the same obviously is, is awesome with our, with our product itself. And so yeah, it's really exciting. And I think I also just try to return to like the parts that are the most exciting and rewarding, which is really, you know, our mission and like what we're achieving for patients, for dietitians, for the system, for our, you know, pair partners, health system partners, like it is really motivating to see those in Slack, we have patient success stories that come in and it's it's really cool to to see you know even if you if you have a really hard week and even if you like see that you change one person's life for the better i really feel like it's all worth it and then and then the second is what we've talked about which is just you know the team i think there's just like a really great kind of camaraderie of working with a really amazing group of people and on a really hard problem you know i think there's this kind of like concept of of imposter syndrome that like you know founders talk about and it's like i i i don't really get it i think in the way that people talk about which is that like um you know i i like i feel like you know my competitors and i like we are the right people to kind of like lead this company and and the mission and we're very passionate about it but i think when i feel like a correlation of it sometimes is actually in a very positive way which is like i'm just surrounded by so many amazing people on the team day in and day out we're like i'll look and we'll be in whatever a meeting with 15 people and I'll just look around and be like wow you guys are all like really really good and like yeah this is you know really really humbling to be a part of and like many people who have like skill sets that are very different than mine and they're very they're much better at things than I am and I'm I really just like wow we we really legitimately could not do this without you and I'm just like so thankful that this person is is dedicating their time to this because great people have so much uh so much like opportunities and options for what they can use their time on but I think I think that kind of like compounds our time whereas I think everyone in the company is feeling that to some degree where they just really respect the people around them and care about the mission we're working on.

46:15And no matter the success of the company, obviously, we have a lot of ambition for what we want to do. I think that's just worth it to show up day in and day out and work with those folks. I love it. Well, listen, we're at the end. So we always ask for our guests to give one piece of advice to the listeners. So what's the one piece of advice that you want to leave them with today? No, I want to give good advice. I think it kind of comes back to if i had to say something like we talked about that that idea of like um agency and and that concept and how valuable that is you know there's like a you know there's a steve jobs quote i really like that's you know essentially like i think it's everything around everything in the world uh around you that you call life was built by people that were no smarter than you and you can change things you can influence it you can build things and once you learn that like it's really shapes your mindset i think that is kind of what what agency is which is like you can look at whatever you're passionate about whatever you feel are are the problems that need solving both on like a macro macro level for the world or like in your your company or or it doesn't have to be business you know your family art music like whatever is your health like whatever is important to you like you actually can change that and like you can influence that and shape that in the way that you want.

47:35And that like, yeah, a lot of what the world, when things change, it often is like a really small group of talented people or an individual or whatever it is that are changing that. And so I think sort of trying to kind of like foster that mindset and realizing just as you go about the world, whatever it is, that like you have more control and more influence than you think. And it'll be really hard, obviously very hard to do hard things, but it's not impossible. And that, yeah, that's kind of the highest leveraged skill set kind of that you can develop. Love it. Love it. Okay. Will you join me in a career confession?

48:09Sure. Okay. It'll be easy. I promise. Depends what it is, I guess, but I already committed. Yeah, you're committed. No backing out. Okay. So here's a little context and then we'll get the question. When a company grows fast, decisions that were simple early on can become heavier. more stakeholders, more structure, more process. So here's the question. How do you keep decisions human, fast and clear, especially in a clinical care at Nourish where people are the product? That's an interesting question. I kind of always come back to, there are trade-offs. It's a very real thing and tensions between speed and quality and between scale and quality and scale and speed and all these things.

48:56But I think whenever I kind of related to the agency point, we talked about like, whenever I see something that's kind of an either or or a trade-off, I kind of try to say like, well, is it actually impossible for us to have both? You know, like, is there actually any law of physics or anything that's preventing us from doing that? Not that it's not hard, but you know, for example, the example you cited of like kind of the quality of the healthcare, yeah, you know, it obviously gets harder with scale, but they're also our advantage of scale. You have a lot more data, you have a really amazing team, you have more resourcing.

49:27And so what I often come back to related to the operating system conversation we talked about is, can we actually just build that into how we work and try to measure it and optimize it? And so if it's quality of healthcare, it's obviously not an easy thing to measure, but there are a lot of metrics you can look at on someone's, their metabolic indicators. If it's a more behavioral thing, like an eating disorder or gut health, you can measure things. And so we really just tried to kind of like build that into how we operate and both like at the tactical level of that, but also at the high level, kind of like define more of kind of the vision of what we're trying to do.

49:57I mentioned is like to reach scale, to help a lot of people, but also to deliver great care, which is outcomes. And we can actually measure both. You know, something like the quality of decision-making or how human a decision is, I think is harder and these things are hard. But like, I think if we were kind of having a conversation and you were part of the team or this person was and we're going through it, I would really try to kind of push in that conversation to work together to kind of like define what do we actually mean by like that decision being human like is it yeah is it actually is it considering the end patient and their outcomes and so like i think we can actually measure that by the patient mps and their outcomes and and whatnot and i'm not saying everything can be measured like we should leave room for the more qualitative but we can also define what that qualitative is like let's talk to 20 patients a month and see what they say about the quality of our care or or if it's more of an internal thing like can we measure employee mps or retention or happiness but again there's a space for the kind of more qualitative intuition let's but let's let's do that let's actually just go ask everyone on the team like do you feel we're better at this than we were three months six months ago and and learn from that and you know i i think if you do that you it's again it's not easy and they're always uh trade-offs but i think you can i think you can do that that well and that kind of is what gets at kind of uh to kind of tie bow on the conversation like treating these things like a product which is like you can't actually like constantly iterate over that time and it doesn't mean it'll always improve like most metrics don't always improve but if you have a bad three months six months year whatever it is which even the best companies in the world inevitably do like you at least can be aware of that and then act to to change it over time yeah i agree and i am so glad you came on the show and i'm so glad we got to hang out because we should hang out more and thank you for just all the valuable advice i am a big fan and i'm rooting for you all and what you're doing is so important You're helping millions of people get well.

51:50And so thank you for all of that work. We really need it. No, thank you so much, Jessica. I appreciate the kind words and appreciate the great conversation. I really enjoyed this. I think, you know, as we talked about, like, I think this is something that doesn't get enough kind of conversation and thought and focus compared to other parts of building a great company. But I think, you know, right back at you, I've really learned so much from you and what you all, you know, built and really look up to you and it a lot. So thank you for all of your help and support. Thank you. Thanks for listening to TruthWorks.