Overview
This episode is a first for the hosts: an in-person recording after more than two years of podcasting together remotely. That setup becomes the entry point for a wider conversation about career optionality, building a business without outside funding, and what they have learned from running Insider Loops together.
A big thread through the episode is the difference between choosing your own game versus joining one that someone else designed. They compare full-time roles, venture-backed startups, and bootstrapped businesses, then get specific about why their current way of working feels more aligned with the lives they want.
Key Takeaways
The strongest idea in the episode is that optionality only helps if you are honest about what you actually want. Both hosts talk about being tempted by shiny paths - working at a company like Anthropic, joining a generational winner, or starting a venture-backed startup - but they keep coming back to the same question: does that path fit their values around freedom, pace, accountability, and life outside work?
They make a clear distinction between bootstrapping and venture-backed building. In their view, raising money can give a company more room to operate, but it also changes the game. Once investors, boards, and the next round enter the picture, founders can end up serving a system that looks a lot like traditional employment, just with higher stakes. Bootstrapping is harder at the start, but it forces contact with reality. You need customers, cash flow, and tighter feedback loops.
Another useful point is their take on planning. They argue that long-range plans can become stale fast when the business is changing every week. What works better for them is strong judgment, short planning cycles, and tight scoping. A week is treated as a long time, not a short one. That lets them ship, learn, and change direction without getting trapped by plans made under old assumptions.
Their partnership is also a major theme. They describe a setup where one brings speed, ideas, and instinct for zero-to-one moves, while the other turns those moves into repeatable systems and handles operational structure. They see this complementarity, plus direct communication and shared standards, as a big reason the business is working.
Practical Steps
- Ask yourself what game you are playing. Write down the rules, rewards, and tradeoffs of your current path. Then ask whether you chose that game or inherited it.
- When a new opportunity looks attractive, go past status and surface appeal. Check it against what you want your days to feel like, not just what the logo or outcome might signal.
- If you are exploring your own business, start with something that gets you closer to the market fast. Focus on what people will pay for and what feedback you can collect quickly.
- Plan in shorter cycles. Pick the most important thing for the next week, scope it so it can actually ship, and resist building the second or third version too early.
- Protect working relationships by clearing tension early. They repeatedly point to direct, respectful conversations as a reason their partnership stays healthy.
- Pay attention to what is already working. They suggest that one of the easiest mistakes is ignoring a strong signal because some other path looks more exciting from a distance.
Notable Quotes
- "When you join a company, you are signing up to play a game that they've designed for you." - Mark
- "I don't think people, I think businesses die because of competition. They mostly die because of suicide." - Mark
- "Having fun in isolation from the market is a hobby." - Ben
Full Transcript
All right, Mark, we're live. First in-person recording. Amazing. I don't know what took us this long, but the energy just feels different. I can see your full body, and I know where to look. That's a huge, huge win. There's still like a Riverside frame around you in my head, and I can't mute myself if I take a sip of water or cough. There's no bed under me, behind me, which is an upgrade. So yeah, I'm excited, man. No, it's also cool to be able to do this after, you know, like we had coffee earlier and did like some co-working here in the city. And it's kind of cool to shift vibes and shift context from that to this. We've been doing this podcast together for over two years. I just saw some friends of ours out there recording as well, and it's kind of surreal to think we've gotten to this point without ever doing it in person at the same time. So I guess I'm really excited for it. And as we were thinking about how we wanted to get started, I think, you know, usually we kind of align with guests on like a trailhead for a conversation, or you and I figure out what we want to talk about, and we decided that we wanted to keep today's conversation as authentic as possible and just like meet each other where we are. And that's kind of like a hard-to-have conversation scheduled out into the future. So what we do, as you know, obviously, in every episode is we do a little bit of an intention-setting exercise with the guest to try to understand how they think about success for the time together. And then we put that lens on throughout the whole conversation. Yeah, and that never makes it into recording. It never does. So, you know, you actually, I think, brought that idea from something you heard on a podcast with Tim Ferriss. So yeah, I was listening, someone interviewed Tim Ferriss, and one of the questions that they were asking him was like, hey, you were one of the OG podcasters, and you probably have learned a lot about the art of podcasting. What is maybe like the best question that you ask? And he was like, actually, it's funny that you asked that. The best question that I ask never makes it into the interviews, which is this intention-setting exercise that I do, which is basically, before we hit record, I'll ask the guest, you know, let's take a step back. Let's pretend it's six months from today. It's the morning, you're in a reflective mood, you're maybe drinking coffee or tea. And for some reason, this conversation that we're about to have pops up, and you're feeling an immense sense of gratitude for that conversation, and you're just so grateful and excited that it happened. And then the question is like, what would need to be true for you to feel that way? So Ben, what would need to be true for you in six months to be excited that we shared this live moment together? Yeah, so I think, you know, I'll say that one thing that comes to mind is that just being fully present and, you know, putting away the phones, putting away the screens, and just, you know, engaging in genuine dialogue is always the thing I, you know, kind of want out of these conversations. But I'd say today's kind of special because we're together in person. And I think that, for me, what I want to be able to look back at is a sense of getting some signal about each, about getting clarity about myself and about you and about our partnership and how we think about things in the highest fidelity way possible, in ways that would be hard to maybe reproduce virtually. So to me, I would say I want to look back and feel like that conversation was a moment where I feel like Mark and I really kind of like calibrated or like understood each other better about how we're thinking about the rest of this year, next year, and feel understood, too. I love that. Yeah, I think for me, there are a couple of things that were top of mind. But all the things you said resonate, and I think we should definitely get into that. But I think we're in a very unique moment in time where I think a special lot of people in product all of a sudden feel like they have unlimited optionality because AI, especially if you're high agency, AI is like giving you all these different potential paths. You could start your own thing, you could do more consulting, you could do more with your time. And I think one of the things that come up for these people a lot is like, should I live my safety net of this job that's paying me well and maybe bet on myself? And I think now, you can do it without raising money or just you can get to idea to product very quickly, right? And so the question here is like, just should I go for it or not? And I think we're, in our own way, we're both examples of like, kind of taking that leap. And I think we've learned a lot of lessons along those two years or four years almost, which I think probably also shape the way we're operating and what we're looking in the future, right? And kind of like we probably made some mistakes, we probably had some lessons that probably will, is going to encourage us or think about differently how we want to do things in the future. So I think maybe those two topics are connected in a way. And my hope like in six months, if someone is listening, be like, hey, like, first of all, like it's, I love the way you, the way you think about your career or your life and how intentionally you're about it, that'd be amazing. But also if we can help someone kind of give them that push and that confidence to just like, to go for it and bet on themselves. And that would feel extremely fulfilling and gratifying if we can do that. Yeah. So what I'm hearing is something like, there's a lot of options right now or high agency people are feeling a lot of optionality and are wrestling with the trade offs associated with the different paths. And we might be maybe like the wrong people to talk about what it's like as full time employees at the moment, which is for sure true. We work with a lot of full time employees and people in that market. We have a lot of perspectives on it, but as kind of like outsiders, insiders, depends how you look at it. And then the second thing I'm hearing is if maybe one of those paths that someone's considering is going off of the full time employment life into something more like betting on themselves in a solopreneurial capacity or entrepreneurial capacity, whether there's anything we could share that we've kind of like solidified as our learnings or principles or ways that we just like think about this stuff, and maybe that'll be that'll be helpful for people. Yeah. And I think tying it back to your intention, I think just what we've learned through that journey informs how we behave today, right? And in a way, even though maybe we're a few steps ahead in the journey, we're still dealing with a lot of the same questions. I think we have a lot of optionality to still in a different way, right? And that's what I love about how we've done things is I don't think we feel like we've figured out the quote unquote answer to anything. I think one of the things I actually love about the way we do things is we have this kind of like growth mindset, and we question assumptions regularly, and we don't fall prey to sunk cost. And we're just constantly re-underwriting the story based on like, what's happening. So yeah, I love I love that. Let's dive in. I mean, like, you know, you mentioned the people that are looking at what came to mind for me is like the grass is greener. For sure. I'm located where I'm located. I'm seeing these AI native companies, I'm seeing the Anthropics and the open AIs, and I'm seeing whatever the Mark and Ben's of the world and like, you know, there's all these people doing different things. And like, and we're obviously projecting also us watching all of these other paths as well and asking ourselves, like, is the grass greener versus what we're doing. So I want to start by like, just talking about you, like, are you do you look at, like the field of optionality right now, and feel that there is something shiny, that is not what you're doing right now that kind of you're like, hmm, should I be exploring that? Like, you know, curious, curious of how much of that's going on within you. Yeah, I think there's like, layers of it. And the more you sit with it, and the more like the options start to narrow up, like actually what I would consider, I'm like, what's, like the hard optionality. And I think there's almost like three paths that I'm always kind of like thinking about is like, okay, I could go back into getting a full time job. I think like, probably if I went back to get a full time job, like the only thing that's like really attractive is like, first of all, like, working at Anthropic, like I look at that, I'm like, sometimes I'm like, hmm, like, is it stupid of me to not try to work at one of these companies that's clearly going to be one of those like, generational companies, right? It's like, it's like, imagine joining Google when it was like a few hundred people, right? Like, that's what Anthropic probably feels like right now. And that's kind of what we'll look back. And I think from a financial perspective, it's probably like a huge, huge win from like talent density and the networking deal make is huge, right? And from learning to like, you're like literally like, with people that are developing the cutting edge models. So you're like, really, just people are trying to figure out how to write, how to work in like the people who are defining how to work in this new environment, how functions operate, what is like the boundaries. So from all these perspectives, like, the story is very compelling. And at the same time, you know, I know people that work those companies and is so from a professional point of view is like, the argument is very strong. But from a personal life, and, you know, I, people here, people that work really hard, right? Like, and I think everyone, it's a company that's full of missionaries. So I think everyone feels like they have to work hard to not let each other out. So I'm like, I don't know if I, that's kind of what I want in my life right now. You do work hard, to be really clear. Yeah, you and I, you know, I jokingly sometimes say we're workaholics. But yeah, I think we fit the work into our life, totally. But the work, we still fill a lot of hours with work. And I think we pride ourselves on that. So what do you think is the, when you think about like that fully loaded equation? What it's I don't think you mean, like, you have to work harder, because I think we work harder. But I think you're on to something. What do you mean, specifically? Okay, yeah, I think you're a good point. And there's almost like the total number of hours. And then there's also like the one, there are things like flexibility, like when I work, right? Like, if I decide I don't want to work on Monday, I don't work on Monday, but then I might make it up on a Sunday, right? And I don't have anyone on top of me that's like, that I have to like, make happy. Like, you know, like, if I don't have like, you know, the CEO of Entropic put a meeting in my calendar, I'll probably be like, I cannot move that. Like, I'm not in a situation right now where I don't feel the pressure for anyone in my team to not cancel or move a meeting, or say no to something. So I think that's another thing of like, just like the, I don't know if it's perceived, but I think the freedom of being able to do whatever I want with my time and decide how I work and this style of work, like I made to put it succinctly is like, my ability to design my environment, like I have full agency over my environment. And if tomorrow I decided I don't like the way we're doing work, and my company operates, we can radically change it, or, you know, me and you have that conversation, and usually, like, we'll get somewhere and we'll make a change pretty quickly. So that's another thing. And then, there's also something really intoxicating for me around having full control over the controllables, and knowing that almost, like radical accountability, like, if something goes wrong with any of the projects that I'm working with is because of my fault, something goes well, it's because I played a key role in it. I think there's something just really beautiful about that. It's almost like this incredibly transparent mirror of yourself, which there's really any other very hard to find other experience where like, I've experienced so much like personal growth, because like, there's no excuses, there's no dependencies, like, it's just me and this thing. And of course, there's like external factors, but like the controllable, controllables are all up to me, in a way. Curious, like when you were, when you were, that last point, first of all, I'd like I really resonate what you're saying, because I think, you know, for me with like a three year old, and like, you know, you know, we like to visit my wife's family in France in the summer, and sometimes daycare calls in the middle of the day, and they're just like, you know, guy has a fever or like, like yesterday, I told you the electricity went out, you got to come pick up the kids. There's just like all these curveballs that come up in life now that I remember, because I did have Gaia already for, I think the first year of guys life, I was continuing, I was at continuum and a full time gig is still a 15 person series a company, but still, you know, like, you know, very ambitious co founding team, you know, strong, strong work ethic, high expectations, responsiveness is valued. And so I remember feeling like I was always kind of like letting someone down or like, not carrying my weight, if these things came up that required my attention, and it sometimes was just self imposed, you know, self flagellation, but sometimes it was like straight up like, hey, like, you need to get your shit together, because we need you like I remember I took some time off in Europe, you know, one summer, and just likes time zones and travel days. And it was like, I just couldn't work as much as I thought I could. And I felt like in a like, there's some difficult tensions, right? I'm like, this work is literally interfering with my life. So I definitely resonate with that. And then I think the the point around like full agency over the levers, I, I definitely feel like, I'd like to think I'm a high agency person. And I feel like I found myself personally. There felt kind of like, you can only move as fast as people will, like, approve decisions in a company. And as you know, like, I like to move fast. I can't always articulate exactly why. But, you know, I think in hindsight, we've looked at a lot of the things I've pushed us to do. And we're like, we're happy we did those things. I look at that even in my own personal kind of solopreneur stuff, like my course and my co pilot and various like advisories and fractional stuff. I've just been like really prolific over the last couple years. And I look at the output from this phase, and I look at the results. And then I look at the output and the results from my full time employment. I'm like, man, like, I feel like I accomplished 20% of what I was capable of accomplishing during my years of full time employment. And I'm kind of like, man, am I is that like, am I giving myself an easy out? Like, could I have done more, but I'm using excuses, like, other people got in the way or whatever. And the truth is, like, these days, I don't think about that. Like, I'm not, I'm not whether, whether I could have done more, or I couldn't have done more. And whether I'm making excuses, or these are all valid explanations. Like, the truth is, I just feel more empowered, I feel like I can move faster and get more done. And to your point, role, like, it's not even that it's not even gambling, it feels like just calling shots, it's like, we're gonna, we see an opportunity, we're gonna move fast on it, we're gonna do it this way. Let's see how it goes. If it doesn't work, let's kill it. If it works, let's double down and just like, play the infinite game of doing things that way. And being able to do that with you. And I think we've found that we actually have a very good way of navigating speed without trading without without trading off like quality or our standards or values or ethics or anything that just feels like so compelling. I'm curious, did you feel similar? If you have a follow up, you can ask. I was curious if any, what I was saying about how I felt kind of like hamstrung a little bit in the full time world resonates. Yeah, you too. I think for me, the thing that felt in the full time job too, is whether you like it or not, when you join a company, you are signing up to play a game that they've designed for you, right? And that game is codified in culture, it's codified in career ladders. And, and for me, I'm someone that I tend to focus a lot. And I did tend to put my blinders on. And sometimes I lose perspective. So what I found too, is that I would just get sucked into the game. And then it wouldn't happen enough where I would just like, take a step back, like, okay, like, is this really the game I want to be playing? Like, am I like, am I questioning things often enough? And I think because I know I'm now I'm the game creator, I get to question a lot more things often. And then I feel like I'm able to like course correct. And I feel like the empowerment and the agency to, to make to make those changes. And but yeah, I fully, I fully agree with you that a lot of times. And when I worked at a full time job, I felt like I was doing a lot of work about work, and right of like, getting the right sign in, like the right, like, you know, sign on an initiative that I'm trying to get, or like getting maybe like a difficult stakeholder to agree with me or to make like do the pre meeting to see like, well, their concerns and in a big company, that's kind of what needs to happen. But like, a lot of times, I'm like, is this really useful? And I think the one thing that I've learned from actually, like, my experience working solo and super on working with you, with a podcast and started loops is that I think one of the benefits that you lose when you go solo is that so I think some of that, like, call it, you know, checkpoints or, yeah, or like, process or whatever, it's helpful to maybe identify some gaps in your thinking, or enhance your work in ways that maybe you couldn't get there on your own. It's like, almost like kind of like the additive ideas or flagging things, I mean, you missed or risks. And the feeling that you go to place that's better, and that you could have not gotten alone. And I think like, there's something really energizing about that, right? I've like, hey, like, I've created this first version. And then, you know, Ben gave me feedback. And now the B2 is like, like 10 times better. And maybe I could have made it two times better, but like not 10 times better. And I think like that riffing and that like, kind of back and forth, and was super productive. So I think that's a part of that. And I felt I was missing when I was doing like, I'm still like some of the super awesome work that I do. And but that feels very energizing with the insider loops work that we do. Totally. Yeah. And the fact that we're like 5050 partners on both, right, like the podcast insider loops, I think, and knowing that we both care equally about things like reputation and like integrity and long term positional game, and that we're kind of in the same space of like helping PMs accelerate careers, like there's so much that I think we've had in common that when we navigate the decisions, it becomes clear that like, we're good at holding each other accountable for the things that we know, we care about, where it's like that we're playing the same game. Yeah, right. And, and in a corporate environment, it's not always obvious, you're playing the same game, there's a lot of like, you know, one thing I took away from my time at Metta, for example, or back then Facebook, is everyone is playing their own game. Everyone's got their own way that they think they're going to get the promotion, the promotion or the rating or the the goal, you know, everyone's like, and look, like, I respect that. Like, we're playing our own game right now, too. Right. So it's not I'm not judging them. I'm not judging their choice of which game to play. But I found myself realizing you to succeed in these environments, I think you have to be very intentional about the game you're playing. And I kind of was like, man, like, is my heart in this game? Yeah. Like, do I care that much about this? And, you know, lately, I've been feeling, you know, as part of the coaching and teaching work that I do in, like, the product, career space and interview space. There's like so many people who were super committed to playing that game. And just given the environment with layoffs, and companies reconsidering headcount, the companies were like, you don't get to play that game here anymore. And it wasn't their choice. They just. anymore and it wasn't their choice they just had to leave and a lot of people have to re-redefine what game they seek to play and I think we've found this is the first time I think in my life where I am extremely excited to play this game and that winning winning the game feels almost like it's happening along the way like every day that we get to play this game feels like a win to me every week every month every year and so I don't think I'm playing a game that requires a bunch of you know shitty days and like false trade-offs every day where like I have to hate what I do today and tomorrow and Tuesday so that like six months from now or twelve months from now there could be like this reward or this milestone instead I think we're actually designing this game to be like is there anything that you don't like right now about how we're working and we have that conversation with each other like this feels slow this feels like it's holding back this feels like it's unnecessary and we're like yeah you're right like let's cut that and so we make these improvements together and then I think each of us also do it in our individual businesses that we just try to like design the game to be enjoyable and there's that that seems like it's hard for me to think about like why every person shouldn't try to find I don't give a lot of like generic umbrella advice but like if we were trying to frame an idea that is something people you know either listening or just that we tell we try to keep reinforcing for each other's like be really clear about the game you're playing think about the trade-offs associated with the game and it's important to just like ask yourself is there a game that I could be designing or playing instead that would just be better overall for life yeah and I think that the hardest step there in my opinion is the intellectual and personal honesty with yourself something like I and I struggle a lot with this right it's like what do I actually want and I think sometimes I I I'm like oh fuck I should be more ambitious right like I should and I would want to build a billion-dollar company like you know like that's what would be really cool and like what success looks like because I'm seeing all these other people do it and actually like do I want anything any of the strings that come with that and often the answer is no right and something with like the anthropic thing I was like man like it would be so cool to work at this company and it's like be like such a cool logo to have but then I like start you start going deeper into okay like what are the things that I figured out that I value in this new life and a lot of times doesn't check those boxes right and same thing with like you know another thing that I've considered it was like yeah make sure I start a venture-backed company and one of the things the values that I care about it's freedom right and autonomy and an accountability and I feel like you know you even though you feel like you're in control when you have a venture-backed company that you have investors you have a board that that you have to report to something like yeah when you start to get a little bit deeper and peel the onion and realize actually no those things don't really fit into like my values or what I want but I think getting to those values and what you want it's actually like really hard and and one of the hardest things is like just really being honest and accepting that honesty because I think some people are like yeah I feel like I should be should be more ambitious or this my friend is doing this or I'm doing this or like this is what I think my parents want me to do right like there's all these and I want to call it a chip in your shoulders but like all this like kind of yeah and baggage influences yeah and I think sometimes it's really hard to kind of taste that bags like what do I want and you know sometimes that I think you made just such a good point about the venture-backed founder thing like people people might not agree with me on this but like the longer we've so I've been I've worked at like several venture backed companies directly with founders I've been an advisor for some and then obviously we've been doing our own kind of bootstrapped stuff let's say for last for me a little over two years for you coming up on four three and a half four and one of the things I've been thinking about is like how some people might think of like bootstrapped bootstrapping as a fast co-founders is just like a degree off from like VC backed but you know like hustle like it's like your founders your entrepreneurs so just one chooses to bootstrap and one choose to raise money right like you know that's kind of one way to think about it and then there's like all these people in full-time employment world that are like doing a completely different thing right and but why do you think that they what do you think they feel that way because I I could almost make the opposite argument that's what I'm about to say is like lately I've been thinking that that I've actually I actually think that the day-to-day life of a venture-backed founder is increasingly looking to me like it's closer to like the way you operate with in a company then as a bootstrapped founder and the reason is that I've talked to so many founders who are like sure if you're a certain founder who's like had an exit before and you can like totally dictate the rules of the game and yeah like Elon yeah like VCs are just happy to be able on your cap table right like you know there's there's like an elite class of venture-backed founders who can run their companies with the same level of the same degree of freedom and agency that we read on our bootstrapped company right but for a lot of first-time founders or less experienced founders that are maybe a bit more insecure need that need the win or they're worried about losing money or they're worried about losing or getting fired by the board right they do operate from a place of like there's some things that just don't feel like the right decision but it's almost like they have to do it we're not gonna name a company but there's a company and that we talk about sometimes that we're like those founders would probably do something very differently if they were bootstrapped versus if they were venture-backed but because they raise VC money they have to take certain swings and compromise certain user experience bars that were like that's not their their entire infrastructure is built for an experience that will not be able to deliver what's best right because they have to justify this massive valuation and so I think I've yeah so that's all a long way of saying I actually think that someone's thinking about starting their own thing and one of the reasons they want to start their own thing is because they want full agency and they want to be able to really move fast zigzag a lot minimal overhead for decision-making no one can fire them then bootstrapping or just like building a profitable cash flow generating business feels like it's like we're so much opportunity is right now yeah I'm so I'm so happy we're not even we never talk about raising yeah it's like never come up yeah not neither of us wants that I would yeah I think I'll be like then I'm out no like I'm I have zero interest in that and yeah I think the disclaimer that I'll say here is that I think it's way harder to start a bootstrap business than a venture-backed business and because I think venture-backed businesses are more forgiving because you get like that security almost you get like that safety net when you raise your seed round or your friends and family right because you have and basically you're able to pay yourself a salary maybe it's not a lot but you know it kind of gives you like that breathing room versus if you're bootstrapped like your safety net is your savings and so it almost feels like the risk is higher and and he's also with less resources it's it's hard to kind of get all the bill like you know you raise a seed round or from the family you maybe can hire one engineer or once someone to help you with sales and but you're unless you have you have a lot of high net worth as a bootstrap founder you don't really have the resources you have to get a lot more scrappy and and I think that that can be difficult the good news is that I think AI is changing a little bit the equation because all of a sudden like just it's just a tool just a tool yeah but but I think I think the thing that makes that that kind of like energizes me about the lack of funding and about the lack of extra resources is it forces you to understand the market it forces you to sell to understand what people want to buy how much they think it's worth yep what would need to be true for it to be worth buying what would need to be true for someone to recommend it like there's all these like fundamental questions about business building that it's hard to get those signals when you have the cushion of raising money right when you have the cushion of raising money it's like okay like we'll find product market fit bootstrapped companies almost by definition have to like I'm not saying venture-backed companies don't have to find product market fit but bootstrap companies almost like have I think tighter feedback loops that require that get them more swings or get them they minimize distractions because you're just focused on like build product put product in front of people sell product repeat build systems for doing more of that add more skew you know it's like that the way we've been approaching things feel so focused and not having extra people around like what do we do with these people or or what do we do with this money and that's one thing and then the second thing is like because we don't have to work our way towards a long-term like insider loops doesn't have to be a billion-dollar company for us to be extremely successful by our standards we get to focus on the levers that make it like 10 percent 20 percent month-over-month growth for five years will get us very far very far very far and yeah yeah there's so many good things here and I think like constraints lead to creativity so I think that's one another advantage of bootstrapped like you know you have constraints you have to get creative about how you do things and the other one is like when you don't have when you haven't raised money right then your most precious resource is time and that's the limited asset that we both have and what that means is that that's like choosing what we do with that time is by far the highest leverage thing and that we can do because we cannot hire people we don't have like we cannot like spend a team of like 20 contractors and why I think that's like beautiful is because it always feels like we are working on super high like impact priority work and and then because there's tighter feedback loops we see the impact of that it's just like this like intoxicating kind of like feedback loop that's that's amazing and and we keep finding ourselves in a new in a new place with more optimality one like we take these things are like one or two weeks of work and it's like before you know it we're like wow like the the board has changed like we can do more things we can do better things we're working on some stuff right now like the the you know like SSO and stuff like that like we we talked about like there's gonna be new moves available to us that are not available to us right now once we do that and it's like we always feel like we're at a moment in time that's getting better and better and more strategically positioned with every one of these sprints that we do I think the other yeah and I think the other advantage I think I'm very proud on the way we operate is that we have the luxury and I'm gonna call it luxury because I think it's the right way to frame it to think long-term and I think a lot of these venture-backed companies don't because they only think of the next round right like the moment they finish raising their series a then you start thinking about all the things I need to do to raise their series B for us like you know we need to hit like a minimum and I guess you know like a floor of revenue that we need in order to sustain our life but beyond that like we don't really like what we care about is like building a business that in 10 years we're gonna be excited to run and that's gonna be hopefully bigger than what it is today and I think being able to think not just in five years or two years or six months ten years ahead and I think allows us to make I think decisions that eventually will put us in a very unique position that maybe other people are not thinking and yeah like maybe like bring it back to like you know I want to call it advice or or like for me like I've been like in a simplification kick for the last like year or so and I think like the key of businesses is just like that I see with funders is not dying right like because like I do think like the more time you spend business the better you get like I just feel like I'm a much better like entrepreneur that I was like four months ago and I think like if you keep getting better in every aspect of like kind of defying opportunities and it's fine like just your skill set the people you work with how you work on things like you'll eventually hit a point where an amazing opportunity comes by and you're gonna knock it out of the park but you can not get to that point if you die so I think like like time in the market beats timing of the market like which again it's like all kind of coming together I think tiny back to what you're saying and you know one of the ways to not like I don't think people I think businesses die because of competition they mean they mostly die because of suicide right and one of the biggest ways that that you commit suicide as a business is when you start having fun and you start hating your your days and like things start to implode maybe you I think like co-founder fights are one of the biggest reasons why businesses fail and I think what you were saying of like just getting up every day and having fun is such a key important part and of what we do and I think because we have full agency what we're doing we can we have a vehicle for having fun right like we obviously are also just like it's not just fun but then again you know I actually I think people trivialize fun too much what do you mean like fun sounds frivolous sounds not not not heavy it sounds light and lackadaisical you know like fun like privileged almost it's like oh look at these people just having fun over there they're not doing yeah they're not having they're not serious they're not serious people right yeah and I think that's kind of bullshit I think if it's actually quite hard to do work that feels fun if people think it's it's easy to find work that feels fun I challenge them to fight to find work that feel like if they're not having fun at work and they're like I want to have fun at work good tell me how easy it is to find that right it's not easy yeah it's not easy at all to find a way to have fun while working and so the fact that we have found that to me means fun is a emergent having fun is an emergent property it's an outcome it's a byproduct let's say of some more complex set of inputs that generate the feeling of having fun but and I and I think that is a worthwhile goal I think it's worth it's worth having a life is short we sleep let's call it eight hours a day we have 16 hours waking hours we spend some of that time with our loved ones family health whatever eating you get you get like eight hours let's say a day to like actually like do work you know like honest hours of work maybe 10 and some more more busy days and that's a third of your life and so it's like it feels important to me that that time generates the sense of having fun and I have fun doing the podcast with you I have fun doing like working on insider loops I have fun helping people achieve their goals super rewarding to me and so yeah like what better yeah you know what better way to spend time and then you know but but I don't think it's possible for us to have the sense of fun without feeling the feedback of from the market like having fun in isolation from the market is a hobby yeah do you yeah I mean do you think it would be like let's say like something happens and like everything that we do together falls apart do you think you would be able to like back in like back engineer having fun like I think there's almost like two parts of it one is the and like feeling like you're contributing to the world and that like you're building something that people want and you're helping people like that's one part I think the other part is like kind of creating the environment where you can operate in like design of genius meaning you're doing work that you enjoy that you're good at and then maybe there's like a third bucket of like doing the work with people that you enjoy working with like is there I don't think there's a separation between the second and the third okay like I think that the environment design like what we talked about with heat and yeah right you've got people come together with vibes they create an environment behaviors and actions happen within that environment before you know it you have culture within that environment and and that culture has a vibe because it's a mixture of both of the people's vibes and when a new person comes in they bring their own vibes etc you and I have been bringing we we've been creating our own I think at this at this point we can say we have a culture we have a way of there's an it's certainly an environment that's an opinionated environment that we are both I think thriving in and and it's got everything to do with the way we make decisions the way we communicate the way we prioritize the way we execute so so I think those are the same like the second and the third thing I think are like the people you work with and like the the conditions I think are very very like the same the first thing you said is interesting because I was generally in the space that we're in on my own before we started inside loops I would say you were successful at it and yet it wasn't it didn't have the staying power or the it wasn't as fun and so I think you know if we were to unpack why you know we're in the same space making the same kind of impact but I never saw what I was doing with my course or with my co-pilot or with my coaching as things that I could like you know it's almost like as the as I got further into the future in my head the questions were not like the prospects of where the path goes was probably more daunting than exciting mm-hmm it's like how am I supposed to do this for 10 years I was supposed to do this like where does this go five years from now right and I was just finding myself kind of like uninspired about where where the path would go alone and then when we started jamming on insider loops I actually think the short-term prospects of insider loops were not that exciting relative to what I was doing on my own but as we launched and started iterating and started building and I started we started build some momentum and I started to see what was possible teaming up with you specifically right I got more and more bullish on Wow like five years from now if we keep executing every week the way we're executing now and we're having fun and it's working and revenues up and we just keep playing a tight game and hold each other like same fucking thing right like let's keep doing exactly the thing we're doing we will find ourselves forget about five years six months from now we're gonna find ourselves in unrecognizable territory yeah that we will have designed there will be no interference from other people if we found ourselves in a place that we don't like it's because we fucked up and I got excited it feels more exciting it's like every week we get into every month we get into it it feels more exciting because as I throw out ideas for where we can go or why we're creating certain types of optionality you are riffing on top and building on top or poking holes and like you're I'm like yeah you're right about this and I'm doing the same for you Yeah, you're right about this, and I'm doing the same for you And we're both constantly in touch with the market both vis-a-vis our customers as well as I mean like we know both hiring managers And we know candidates we know Like we basically talk to all the people that are in the space that we are building our business in so we Were able to like sanity check all of our assumptions on a regular basis And it's impossible for us to get delusional like we're we're like so fucking plugged in to like what the market is thinking about and what? people want and So it feels like grounded it feels ambitious it feels like there's network effects that we're developing And it feels like every step we take forwards opens up more Optionality and then we're not compromising any of the things we care about outside of work to like enable that So that that feels like a great game to be playing. Yeah, I think maybe there's like an implicit Factor there, too that I think I think we both have the advantage that we you know have worked on multiple companies but also have done businesses and ourselves like you know independently and I think that here. There's like In the case of insider loops, but I think it's worth being in it's like. I think there's like a very good like Kind of like opportunity founder fit kind of kind of situation Not just in terms of like skill sets reputation expertise Positional game, but also in terms of skill sets right like anything like what you're really good at what I'm good at and It's actually become more clear that we have company entry skill sets over time right and it was in the beginning because in the beginning We're like oh wait like we should all be 2 p.m.. We're two solo. Yeah founder p.m.. X p.m. Guys yeah, how much could we possibly complement each other and we found? I mean, I'm curious like what you're what you've learned about that over time yeah, we think like a meta lesson here that I just want to like throw out see if it resonates is and I I Think one of the ways that I think it's very productive on how we work together Is that we don't really? we prefer action over planning and I think Even though like current really feels like it might be more efficient to plan first because like you know like kind of where you're going I think actually you get too much of our place when you like take action See what happens, and then like kind of let the dust settle and like because you just have things You just exact more, and you just know where you're going, and I feel like we've done that with The podcast we've done that we've started loops We've done that like like what are areas or responsibilities within the company right like in the beginning? We're like we're like let's just both kind of do a little bit of everything I'm like we'll see kind of where like we naturally land And I think now we've we're a place where like we haven't even explicitly had a conversation of like what you do What would you say to like if you had to like verbalize yeah, like what what are I don't think it's like perfectly clear No, I think what are the yeah, we haven't actually talked about this. Yeah, what do you think are starting to emerge is like the different areas of Where your superpowers are and where mine are yeah? I mean I Think you I mean like there's like the obvious one of like you're just like more of an expert in the interview space something like kind of you like I when it comes to like evaluating like some interview guys or the validity like I think like you're just I Just trust your perspective over mine, and I feel like I've learned a lot through it And I think I'm gonna get closer and closer, but for now I think you're you're definitely like there, so I think that's like really helpful, but from I got company building perspective and I Think what are you really good, and I'm just man What you really enjoy is like that kind of like zero to one of like hey I have an idea and I want to run with it, and I just like I'm just like Scope it very well right I'm like get something out of the door. I'm like getting that energy running and I really enjoy kind of taking that energy and That first version. I'm being like hey How do we make this like work in a way that's like? Sustainable for a long period of time in a way that we can do it consistently, but it doesn't break and that allows us to maybe and Clear our headspace So we don't have to that so so we can do other things right, so I think like I really enjoy like the operationalizing these systems and I'm kind of taking you're really good at that stuff. Yeah, I enjoyed yeah, it's it's it's fun on But I think I hate it. I hate that stuff. Yeah, so I think like that's like Yeah, it feels great. Yeah, but then it's like in a way like I needed it, but it like kind of like and then you're I think you're very and you really like speed and I think and For me. It's really fun to like create systems like even allow you to move even faster, right? and I think like it's just like you can like seeing the whole machine and like because then it's like in a way it's like The machine that I'm building is getting used more because like Ben is like putting that velocity into it and So I think that's that's one thing Yeah, I I really enjoy like in dealing with difficult customers, like I just something that like I Have through Supra. I mean, I just we deal with people all the time. So I'm just like I've I've learned how to navigate then I think so that you you enjoy like So the positive tracks of the negative ones are like I and I by the way, I think we It's emotional for me, too But I like I think I've like been able to like okay like detach myself and like kind of think how to do a lot Something like that's been a fun. I think I think you're better at like the boundary setting with customers Yeah, I feel like I take every every customer interaction kind of personally. Yeah, and then I think you Have a way of kind of like making it objective a little bit more objective and trying to get to like what's actually going on here Do we want to like if we respond to this customer about this thing? Does that now mean we have to like answer all of these things from other customers or do we draw a line and say? Like that's this kind of like service is not offered as part of like buying the buying these guides, right? Yeah, and I'm like Yeah, yeah, like we should have we can't we can't possibly do this for everyone. Like it's not gonna scale at all If you're enjoying this conversation, please check out the links in the show notes to support the podcast Mark, and I do this out of love but to keep it going. We also need your support. Thanks and now back to the episode Yeah, I think also the other thing too is like you're very You said prolific or generative like I think you have a lot of ideas. You're very creative you're always like connecting the dots like you're you're I think like your brain is always like kind of seeing opportunities and stuff and I I'm very different in the way that like when I commit to something I block everything and like I just I Really enjoy operating out of some I can be creative but like I when I'm committed to something I know like I need to block distractions. Like I just like execution execution execution and I think that's helpful like it's like I think we're you're able to bring more of like the expansive thoughts and I'm able to bring more of like the like Discipline like, you know focus of like hey, this is actually like the an opportunity worth pursuing and kind of back to the How we started the conversation right of like Optionality like, you know, I I Do have those thoughts about on tropic. I sometimes do have those thoughts about venture-backed companies, right? I got friends that have raised millions of dollars like like the companies are worth hundreds of millions, right? I'd so and But yeah for like I don't really go that deep into a rabbit hole until I realize like yeah I don't want any of that But when it's really hard, I think when we're in the path that we are right now, right? where we like have cash flow we are have a growing audience is and Deciding what opportunities we go after and You know, I think by the nature of humans is The grass is always greener, right? So like and sometimes we think like hey Actually, maybe this opportunity is more exciting or maybe like we need to supplement it right and I think That's actually the part that's really really hard I don't like even just like how much time I spend with super ever since I lose like Or like, you know, we we get pitched ideas or you like come to me like hey, should we do this too? and I think those are just thinking really hard because like, you know, like six months ago inside it loses nothing and I don't want to share like numbers publicly, but like It's how to lose right now. It's decent business like so So you can always like when you have seen that happen You're like hey, what if there's another business that's like even bigger, right? so like it's almost like it's hard to it's hard to commit when fully when you have so much optionality and And I think we both feel that a little you know in a way I don't I don't want to put words in your Mouth, but that's interesting. Like I feel like I've learned to not underestimate the value of something that's working. Yeah, true and And Because insider loops feels like it's working and because I think we see a path At least in my head I see and I think you know, we've discussed it enough that I think you see it too Oh for sure We see a path for where it goes. So then to me I I It's like once I see that it feels like everything else starts to quiet down like I'm not thinking I'm Thinking like that like this deserves as much water and sunlight And I guess carbon dioxide As it can get good soil good soil and like Because we're controlling the inputs like I just don't want to feel like I think we've talked about I'm not motivated by like beating the Competition like that's not something that motivates me. It's like we have an opportunity to build something pretty unique that's like very valuable that I wish I had when I was interviewing that We've talked about the company side like that that as a company I wish Existed for candidates like I can't tell you how many times I was interviewing people at meta and they just came in and like it's clear They just were not prepared for that for the interview and it's like that sucks for them because like that was a pretty high-stakes moment for them that could have led to Something really meaningful and they they fumbled not because they didn't want it But because they just didn't know how to how to approach it. Yeah, so I've seen I've seen the problem and then And and I think we're like there's no one better than us to build this I think I think we're like the right guys like build this business and And so that feels so energizing. It's like it's ours to lose like I think we Keep making good decisions. We'll get to a good place. I don't feel Distracted I think the way I think about opportunity you talked about how like a more creative Oh by the way, did I miss anything you feel like I miss anything that like how we were like or like how we like You know compliment each other. Yeah Yeah Like sometimes I'll just come in hot with an idea and I think I can or even like Bring my headspace into an idea and I just think because you're better at Tuning out the noise You're you're you're good at being like actually This could come off the wrong way for this reason or like, you know here's how someone else might see this and to be honest like I Haven't had that trusted voice for a very long time like someone I could come to with like high-stakes Comms or like, you know, we literally like go back and forth on email address It's like what do we do we say it like this do we say it like this? and so the ability for you to like do that for me is grounding I wouldn't underestimate the value of that and then it's funny because you you don't like If I get excited about an idea and you think it's a and you like the idea you will add velocity Right, and if I come up with an idea That's not a great idea or you think it's not aligned with what you know I care about or what we've talked about you'll you'll like slow down the momentum of that idea and I know that if I if an idea loses momentum for me It's usually because it's like the beginning of the end of that idea or that seed of the idea but the moment that an idea comes to me and it gains momentum it kind of fleshes out and Reasons that are kind of hard for me to to imagine when the when I have the kernel of the idea So all that's to say like I view you as a very helpful partner for taking my gut feelings and Literally like manifesting them, right? Like I I look at what we've built and I'm like I couldn't have built this on my own for sure There's like no way I could have built and so I look around and I'm like I recognize what we've done and I understand why everything is the way it is and I feel like it's better than it would have been without you and then the other thing I would say is like You are Very comfortable with Difficult conversations and kind of like managing conflict and I think neither of us lets things fester So the air is like always clear, you know, there's never anything that's really nice like there's like no drama. Yeah and the relationship Like it you've said I've done things that rubbed you the wrong way and you called them out and like you've said some things that rubbed me the wrong Way and it's like we're getting to know each other by like understanding those those pushing the edges Yeah, like understanding what those yeah calling them triggers right? Yeah, but but I think we're really good about like Just communicating respectfully with each other and Pushing each other. It always feels like we're sitting on the same side of the table There never feels like there's any like your success is my success. I genuinely think we celebrate each other's success And then when we are going through busy periods or something, there's never I never feel guilt about it I always feel like like if you're going through a busy period I I feel like I'm just gonna I just feel motivated to like pick up the weight and then same here I've noticed the same with you when I'm in a busy period or something so yeah, the the desire of keeping things moving forward and then the other thing I love is like When I do stuff without asking you first and I just tell you about it after It's like 99% of the time. You're like awesome Like I'm so happy you did this and then I feel the same way about you So it's like there's a sense that things will move forward in a productive way without having to approve or ask for permission and It's very rare that we have to like walk back something because we're like, oh you did something. I don't like agree with I think we have this shirt Judgment understanding of what both of us value and I think we both also understand what's high stakes and what's not high stakes, right? I guess like we wouldn't do anything that like feels high stake without checking with each other, right? Yeah, like we talk like every day. Yeah, we talk like multiple times a day every day I mean Carol like we joked in the podcast calls you my work husband and I think it's I Think we've created the environment where like we're happy to share good ideas and bad ideas with each other but we don't know the difference at first between like what a good ideas and what a bad ideas but like we trust that if If I pitch you on a 50-50 idea and you're like, that's really good I'm like, okay Let's do it And we were very good about like documenting it adding to the list and executing and then if I bring up something It's not a good idea. We just don't we you know, I'm like, okay like that that version is not great so as a result of that we move really fucking fast and To kind of come back to like just so you understand yeah, like so when I when I think about like ideas and connecting the dots, it's like I Think a lot about us building You know we talked about the positional game but like let's define what that means because like I think it's so it's such a critical piece of why This asset that we're building and why this game we're playing is exciting. So the idea is that We we we launched with three guides and we're like Let's figure out if anyone wants this let's figure out if we can do it Okay, and then we did and we got lots of good validations like okay now Do we focus on driving more traffic to these guides or do we focus on adding more guides does it like what's the best way to like Go and we we've talked we literally look at each of those options. We're like, okay, let's add another guide So we had a door dash right and then we did the same thing with open AI and it was the same thing with Google And then we said the same thing with anthropic and so now we have seven guides and We're like, okay, let's do this. Let's do this. Let's do this. Let's do this And so now we have seven guides and And when we're building the open AI guide, we're like hmm It was actually right around the time. We got a difficult customer Yeah feedback and like they were looking at one of our guides and they're like I had certain expectations and like well We didn't advertise those expectations but like Good to know that those are the things that you care about and then we started thinking about like if we did wanna at some Point address some of that address some of that incorporate it and we were delivering our guides on gamma as presentations like password-protected gammas We're like what if we started to build our own guides like what if we actually used Fod code and all these AI tools that are now available and what if we built our own guides and we were like Let's do it and within like what a week We had our open AI guide built natively and then we're like, yeah We should probably bring our other guides and now all of our guides are built natively and we've migrated them so we have no dependency on that and Now it's like okay now that we fully own the code for all of our guides and under design system and design system And like now it's like what should the experience of a guide be is entirely up to us Yeah Full another level like full autonomy and agency right if like customer experience user experience entirely up to us literally if it's if it's possible in code we can do it and and that felt Like we would not be able to do what we do today without that We wouldn't be able to even think about the moves available to us without that SSO for example But but we don't get to that decision without chewing without literally taking a difficult customer Customer conversation and being like shit. There's some truth in this We the exact claims are not what we agree with but like reading between the lines like do we Like yeah the way we're delivering our guides like they should be better right like we could do better than this and so what I love is like the the sense of craft that we could get into this and now they also be then realize hey like this Makes us way more excited to update the guides, right? And like we it's all integrated into like our Code base we now we now can go from getting an email in the morning From a customer about going through an interview loop that had a variation or like a slight difference on maybe a certain interview type Relative to what was said in that guide, and they're not it's not sending us to us because they're upset They're like just so you know I think they're changing this thing So you might want to reflect that for other people that buy the guide in the future And we're like wow like these people are generous with these insights And then we started growing this we had a growing backlog of these like You know things we need to incorporate in the guides because it was so heavy to incorporate them into the guides We're like sitting on maybe like a week or two or sometimes three weeks or four weeks of delays And incorporating them into the guides, and then we're like let's solve that problem, and then you put your Blinders on and built a system that allows us to go from you know getting an email Like if we got an email right now while we're recording this I think within maybe assuming the first like we can basically have a proposal ready from an agent For how to incorporate into the guide using our guide updater skill that we have I'll review it in github as a PR if I like it. I'll be like Ship it and then the next time the script runs. You know it's gonna be in the guide I'll get notified. It's been merged production and the task that we used to track that ticket is resolved and Boom yeah, it's done right so now we've built our ability to incorporate feedback in a way that makes the guides better and better and better Faster and faster, and that's the kind of system that will work for us We would have never been able to do that if the guides were still being built in gamma Yeah, so like the entire machine is getting better as we're moving What's really interesting about kind of working with you on the experience over the last three months. I would say is You've really helped me change my mind about Long-term planning versus short-term planning like I think I used to be a believer that like you need to have a cohesive strategy that you're working towards and and then like And then you have to be like a plan to execute towards it and like that plan should be like a few months Long, and you should be like you know like you should never lose sight of that big picture and I Think we had done that three months ago like we would right now, and we had like stayed committed I'm disciplined to that plan. We would be building complete the wrong things, and I think that Like actually have gone like full swing the other way actually like if we plan more than a week ahead I'm like what the fuck are we doing or like? Like I actually think like every day it almost feels like every day like we should wake up and be like what is the highest? Priority thing that we should do based on like all the color priority thing that we should do based on all the collective knowledge that we have about this company. Because things are just changing so quickly, and I think because you build that skill set to hold up that context in your head, but also detect what signal from noise, and also your world is constantly changing, and the system, and we would have never predicted what would have happened when you create a native guide, and then you have a skill that updates them every hour. That creates a fundamental new universe that we would have never been able to predict two months ago, right? So I think, yeah, I actually think it's way more exciting when you wake up like, you know, I don't know what I'm going to be doing next week, but it's going to be like the highest priority thing. And the reason why that is true is because our world, like we're changing and moving so quickly that we just cannot predict what that high priority thing is going to be. And I think that's part of the fun for me, that I think I'm actually trying to bring that to different parts of my life as much as I can, and I realize that like, we're very privileged to do that. And I think when there's more coordination and more like dependencies, you do have to plan a bit ahead in advance. But yeah. I love that you like, you like it. Yeah. Because like, this has been, this is kind of just like my main, my default mode of operation. But as we talked about earlier, like in large companies, or like any corporate environment, you just can't, it can't. No one would want to, I mean, maybe not no one, but like, I don't think, I think it's so rare to find an employer who wants to hire someone that will only think one week at a time. But. But in a funny way, that's what CEOs operate like, right? Like, I think like the best CEOs, like, in my opinion, like, they get up and they're like, hey, like, I have a limited bullet for today, like, what is the most important thing that I can do for my company? And I'm sure that changes. So often. I'm sure every CEO is different. Because they're just people. Yeah. I think the reason it works for us, it's not, it's not, it's not an attribute in isolation. Like, if you, if you told me all you know about someone is that they plan one week at a time. That's not a very, like, you're like, no, I don't know if that's gonna work. Like, there's a million reasons that shouldn't work. But the reason I think it works for us is like, a week is a long time. We view a week as a long time, right? Many people will look at a week as like, it's only a week, right? But I look at a week as like, that's seven fucking days. We only have 52 of those a year. It's but like, we have if you have 300 bullets, a year, every day is a bullet, got to spend that bullet wisely, wisely. And if you think about companies, they operate like a one month plan, or you get 12 bullets a year, you do six month planning, get two bullets a year. Like, if you operate at a weekly clip, you get I mean, if you cannot get shit done, like important shit done in a week, there's something wrong with like the planning, there's something wrong with the scoping, there's something wrong with your understanding of the opportunity. Yeah, I think that's a key part. It's like, I think the reason why our weekly planning works, because we're really good at scoping. Like, we will only scope things that we can deliver at the end of the week. Super good at scoping. Yeah. And I think that is the really energizing piece, because like, I hate like finishing a week and be like, what, what did I accomplish? Like, I know for Insider Loops, I want to be able to look back, but I hate these are all the things that we accomplished. And not only we accomplished, like, they were delivered to customers. I mean, we're here at the end of April. Yeah. And we look, we literally the other day, we're like, did we ship Anthropic this month? Because it feels like a long time ago. I was like, no way, man. I was like, it was definitely March. No, I know. I know. We shipped Anthropic less than a month ago. Yeah. First week of April. And it feels like we cannot imagine, like, the Anthropic Guide has been so successful for us that, and it's opened up options for us that has allowed us to dream a bit bigger than we would have otherwise, and to build conviction in ways that are fleshing out the future of where we're going. That we're, I mean, when I talk about, like, a month from now, us being in a different place, I think we would both agree we were in a very different place a month ago. And so how many people can say that? How many teams can say that, like, that in month six, like, let's say we're coming up on month seven of Insider Loops, roughly, since launching in September, that at month seven, they felt dramatically differently about the prospects of the company than they did at month six? How many people can say that, right? So I think, like, the reason for that is, like, even a week sounds long. I think sometimes we, like, check in with each other same day, and it's like... We're done. What are we doing, like... Yeah, tomorrow. Like, we just got done, let's say it's, like, Tuesday. We talked on Monday. We thought Monday's priorities would take the whole week. Tuesday comes around. We're like, we're done with the week's plan, like, what's the next thing, right? And we will set arbitrary goals or arbitrary deadlines and hit them early, right? Like, we do these things to hold ourselves accountable for speed. And then the scoping conversations are, like, the best conversations, because it's like, no one wants to work on something that has fat on it. No one wants to work on something that's not essential. Even as, like, we're doing this big, like, you know, we're trying to do, like, the authentication stuff. Like, we had a great conversation yesterday about scoping, and we're like, we're going to build something that's going to have a lifetime of, you know, probably, like, three to six months before we have to, like, do the next version. That's right. But that's, like, the right move. Like, it's, like, three to six months to our earlier point. Who knows? So, not overbuilding and not overengineering, considering the tradeoffs. I mean, that's, like, super, like, that's why I think this company is better being run by two ex-PMs. Like, we're bringing in our PM superpowers, but we have the tools of a full-stack EPD trifecta. Yeah. With, in a lot of ways, because of our positioning, like, unfair go-to-market advantages or distribution advantages, we're doing a, we have a podcast, so we have, like, our own audience, and, you know, it's not as large as we'd like it to be, but it's growing. And I think we're, like, full-stack, you know, like, we don't need anyone else. Yeah. Like, we don't need anyone else to operate this business with us. We're building, we're doing really well the way we're building it. Yeah. And I think we, as long as we keep, like, the one thing that I think is, like, super important to keep in this industry is, like, reputation and trust. And I think we're both obsessed with those two things. Like, we both, like, our biggest fear is to compromise on that. Because you don't, it's hard to recover. No. I mean, I don't think, I actually don't really think you can recover. I mean, in a short period of time, maybe in 10 years, like, there's, like, redeeming stories, but, like, it's, there's always going to be people that, hey, like, that will kind of look back and be like, that was the person. And we're seeing it pretty light with some people that we won't name. I'm not going to tell you, like, I don't want to make this into a planning question. I want to be more of, like, how do we want things to feel in a year, right? And, like, I think that means we need to look at what feels like it's working and what do we hope maybe will be different or, and it doesn't have to be different because, like, we don't like the way we work, but, like, maybe, like, how we're spending our time. Because one of the things that is true is that we're two people and, you know, there's a lot of things that need to happen when it comes to building a company, right? And that means that, like, in a way or another, like, we both have to eat glass, right? And I think we've designed in a way that, like, we're minimizing that amount of time and we're a lot of times questioning if that's true. But I think there's always some unsexy parts. Yeah. Or, like, there's things, like, you almost wish that you were doing, spending most of your time doing the things that you actually, like, love and reduce the amount of time that we spend doing things that we absolutely love and that we're having a blast with. So, yeah, I'm curious, like, how, like, in a year, like, what do you hope to be feeling? What do you, like, if we're having this conversation again? I hope to be feeling that we cracked distribution and traffic generation in a way that is not something we have to actively think about. I think we still think about how to drive traffic and how to grow distribution. And it doesn't feel like a distraction, but it feels like it's certainly something that I wish was a bit more kind of, like, on autopilot so that I could do the things I'm more excited about. The things I'm more excited about are, man, like, product. Love product. Like, I love... And how do you... I'm a product builder. Like, what got me into product management is it seemed like it was the best job to do my favorite parts of having been a founder, which were designing interfaces, talking to customers, iterating on designs, creating delightful user experiences. Like, so as I think about, like, a year from now, if we can execute on the things I think we care about, the user experience of Insider Loops will feel a lot more fleshed out, feel a lot more robust. It'll feel complete. It'll have the right feedback mechanisms at the different touch points that allow us to systematize improvements across different product offerings that we have. Yeah. It'll feel like the system's working for us. Yeah. The thing about product is there's so many... For Insider Loops, there's so many layers to product. There's, like, almost the content that's a product in itself. Then there's the manifestation of the content, right? Like how the guides look. And the models will keep... Who knows how good the models are going to be in a year? And we're actually one of the kind of companies that are... We're AI. I would consider us AI native. For sure. So I would say, like, as the models get better and the capabilities get better, the guides will... Like, talk about magic being delivered to us and having to bring it to market. Like, we've learned about OpenAI as they think about their PMs. Like, hey, here's magic. What would you do with it? We're actually getting the same gift. It's like we're getting it a little bit more delayed than the people at the Frontier Labs are getting it. But they're still giving us new magic. And, like, if we're well-positioned to incorporate the magic, then, yeah, like, I'd like to look around and be like, we are continuing to be AI native and getting... I would like it to still be the two of us, honestly, a year from now. I don't think we... Yeah. Maybe contractors for the stuff that we don't enjoy. Small things. Like, I think, like, maybe having someone who, like, reviews the copy and, like, making sure that, like, the writing is beautiful and, like, concise. The guides should definitely be less text-heavy in a year. I think we should have more visuals. More images. Yeah. I think we should have more practice tools for people to leverage the content of the guides. I think we should have more of a full-stack offering for, like, a full-service offering for people getting ready for the interviews of the companies that we support. And I think we should still feel the way we feel about building it. Yeah. I agree. What would you like to be doing more of, if you could? I think all that would keep you pretty busy, if I'm guessing, with me. Like, we're both doing product. You know, I think, like, being very real. One of the parts that I love about this space of interviews is that you have the potential to transform someone's lives. Like, I deeply mean that, right? Like, if someone lands a job on OpenAI Anthropic, like, what the equity is worth, what the base is worth, like, that can change the trajectory of that person for the rest of their life. Not just financially, having that logo there. And feeling that you have, that you've played a small or significant role in that, like, is extremely energizing. At the same time is one of the areas where there's a lot of people that are hurting, that are, like, are in need, because they maybe lost their job and they're, like, eating up their savings. And I wish I could do more for those people. Like, there's almost, like, a weight to give back, right, and be, like, and me not feeling we're monetizing on desperation sometimes. I don't know what that looks like, but I feel like we almost kind of, like, could do something about, like, yeah, kind of helping those people that really are just, like, in a bad place. Because I think there's, you know, in the market, there's always people that are just, like, the top 1%. Those are people that are getting paid really well, and just jump from one great company to another great company. I think those people, like, you know, happy to help them. And I think they should be, like, you know, we should be charging them for what we do. I think there's, like, at the bottom 1%, there's people who are just really lost. And I think some of them maybe don't have the talent or the skill set, and they're in the wrong job. And maybe, I don't know how we can help those people. Maybe it's, like, helping them ask the hard questions. But I think there's some people in the bottom that are just, like, maybe don't have the resources or just never had the right mentor or the right guidance, but have the right skill sets, the right raw power, the right attitude. And I don't know, that's something that would be really cool, like, if we could get to a point where it's, like, we're so expansive, and we have the luxury to just find ways to help those people. Like, that would feel, like, very beautiful and, like, almost... I think it also would help, like, our long-term positioning, too, right? Where it's, like, hey, this company just cares, right? That's something that I think a lot about. Yeah, no, I love that you're bringing that up. I mean, a lot of people are struggling. And you can't build something for everyone. So I think we've made a decision to build Insider Loops for, call it, the top 10% of the market. It's kind of who we're building it for. But you know, there's, like, 8 billion people on the planet. Financial and economic opportunity is not equally distributed. So I think, on one hand, I agree, and I think that content is probably the most, the best way to help people who cannot purchase our guides or cannot access the paid offerings that we plan to deliver. And I think we've done... We should give ourselves a pat on the back. I mean, this podcast has not been bringing us any income. And yet I think we aim to create content that is extremely useful for people, and it's free as long as you have an internet connection. I think we try our best to put out content, like, trying to offer some insights. I mean, I think the work I was doing before Insider Loops on my, like, my Lenny posts, my interview templates, my talks that I've done, my lightning lessons about interviews. Like, I regularly get emails from people that didn't pay any money for any of my stuff, and they're, like, thanking me for the resources. I would love to get more of that through Insider Loops somehow, for sure. And I think we're well-positioned to do it. Yeah. I think we... The way I think about it is, like, we're still finding out who we are as a company. And I think as we feel, like, more secure in, call it, like, the paid offerings, it will be clear to us what are the things that we can kind of, like... Open source might be the wrong term, but, like, things that we could make available more publicly, either for free or for much, like, smaller price points, without having to compromise our ability to, like, build, like, a valuable long-term. Because we're not going to be able to help anyone if we go out of business. So... I don't think they're mutually exclusive, right? But I think it's, like... I think of companies like Tom's, for example, right? Like, you buy a shoe and they get, like, a shoe out, right? But, like, I think about this podcast, I mean, it's, like... I'll bring it up, but, like, you know, I've asked myself the question of, like, should we use our podcast more for the audience in the space of what we're building Insider Loops for? I mean, it's, like, we're... Sure, we're talking about product management, which is... It's, like, the podcast is technically marketing for us individually. It's a vehicle for having fun. Like, we love doing this. But, like, should we bring additional intentionality to, like, what we talk about on the podcast and make it more related to, like, job searches and careers and interviews? I can make both cases. I can say, you know, it's overly constraining on one side and maybe it kills some of the fun and the expansive nature of what we can talk about because we can't bring people on that can't talk about those topics. But on the other hand, if it's, like, hey, if we want to go deep in the interview space with every asset we have, then the podcast is obviously, like, something we could explore going deeper on interview content and it would be free. So I think about that, too, and I haven't pressed on it, but, you know, we have lots of options for, I think, creating resources. I'm just excited to spend more time thinking about that. But I think to wrap it up, maybe, like, I think there's a good topic you brought up on, like, what is the role of the podcast, right? And I think maybe what I don't get super excited and hope this doesn't come back to bite me live is that about, like, just doing, like, interview content is that I see this podcast in my life as a way to, like, have really interesting conversations with people that I find interesting or that I know or that you know and to be very present, right? And I think I enjoy, like, the wide range. I mean, you know, it's still very focused on product management, but I do enjoy the range from, like, interpersonal to AI to career, perhaps. I think it's naturally going to go, it's naturally going to, we're naturally going to have conversations about kind of interview prep or how to land jobs. But I wouldn't, like, I never want to feel like I'm not excited to come into the virtual studio or in-person studio to record because I've pigeonholed myself in a topic that maybe it's not what I'm most excited about at that time. So I think that's, like, the only risk and, you know, I still just feel very protective of this space that we created and to have these conversations. And I still mean it when I say, like, this is probably my favorite time of the week. So I think that's how I think about it. And I'm, like, maybe it's, like, supplemental or maybe it's, you know, there's going to be points where we learn something or we have some learnings or, like, hey, like, we need to get this out. But almost, like, I think the excitement needs to pull the content out of us instead of, like, having a force and function to pull the content outside of our bodies. Totally agree. I think following our energy, following our curiosity, it should feel like play. And I think, you know, it's funny because we're obviously building a company that is in the PM interview prep space, and yet we don't, we view this podcast as something different. And I think it's kind of cool to have two different things that we do. And you know, that's actually something that's probably just worth touching on for a second is, like, the fact that we run a podcast together that is not about our business, and the podcast precedes the business, is really cool because we have this outlet for just, like, hanging out together and doing stuff together that is not related to the company. And I think if we weren't, I'm always worried about fucking up the podcast by forcing it to be something different than it was before Insider Loops. Totally. Because, yeah, like, Insider Loops can die, but it's kind of almost comforting that we know that the podcast, if Insider Loops dies, like, the podcast probably doesn't need to die. Insider Loops won't die. Yeah. No, but I'm just like, I'm just, like, kind of being, like, you know, a doomer. Like, we're saying it's, like, the podcast supersedes, like, we've always said the relationship first. Exactly. Podcast second. And then now that we have Insider Loops, Insider Loops third is kind of what it feels like. And there might be a point where maybe that changes. I just don't see them being at odds with each other. Exactly. And I think they build on each other. As long as we, our relationship stays healthy, that's going to feed everything. The podcast, you know, it's hard for me to see a world where we choose to stop doing the podcast. But, like, I still view the podcast as being a battery of sorts that energizes us. And then I think Insider Loops is, like, our ability to, like, play ball together. Right. Like, we're building something together. We're doing work together, having fun. And you know, the cool thing about that is, like, we don't have to force the podcast to become something that it isn't. If we don't have to. If we don't have. If we don't have to my if we don't have to monetize our relationship through the podcast that keeps the podcast What it what we want it to be yeah? You know it's a crazy thought that Inside our loops is like a almost a byproduct of us caring so much about the product about the podcast That we were like hey We don't want to much like we don't want to get like a shitty sponsor for the podcast so then But we're itching of making money together yep So then inside of those was born so in a way we have the podcast to thank or Inside of loops because like it was like this thing that we cared so much about they were like hey like we should find another way and So yeah kind of kind of a cool full circle moment cool full circle moment. Yeah, I mean, man. I don't know if anyone's In this conversation, but I really enjoyed it and actually that's one of the last kind of things I'll say about the part of the school is like we had a lot of these conversations life I think it's gonna be such a cool artifact and like when you can show a daughter in like 10 years But hey, this is what I was thinking about when I was younger or us It would just be like you know it's crazy. How we sounded in 2026 now over here, so I don't know It's a moment in time. Yeah, it's just it's cool to be able to do this and to have an honest conversation that flows and Have fun while we're doing it And I just want to thank the team here at 28th and park for letting us use this beautiful studio it's so fun to do this in person so fun and Alex Pavlo and the team here are working on some really interesting stuff and I just want to say like thank you for for letting us use the space and Hopefully every time you come visit New York. We'll be able to Yeah, make a make an occasion out of this Yeah, seriously if you have a podcast if you're thinking of hosting an in-person event and the space is absolutely beautiful Yeah, they will come and book it so you can you could you know pay pay? I think it's for the hour for the session The team here has an awesome setup audio video cameras Lighting yeah, so we'll include a link in the episode notes to come and grab some time and You will not regret it. We saw some actually awesome people recording Yeah, they have multiple spaces here in the in the and they have like a I think like three different places You could record here. There's also a different dark background if you don't like the light background, so yeah anyways Yeah, that's our sponsor today is letting us use the studio yeah, and we also might have found two new podcast guests from that Triple win yeah amazing. I think that's a Rob man boom boom boom appreciate you man appreciate you, too If you enjoyed this conversation, please share it with someone who you think would benefit from it as well We really appreciate it. We'd also love a follow or a rating on substack Spotify or YouTube that's gonna let other people find us and if you have any topic recommendations for a future episode Please send myself or mark a DM on LinkedIn. We'd love to hear from you. Thanks