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The Lead — Nov 9
SUPRA INSIDER · MARC BASELGA, BEN EREZ

#135: Inside a live co-founder money therapy session | Jeff Greenberg (Executive & Founder Coach)

A co-founder coaching session turns money into a conversation about freedom, security and the fear of losing control. Two Brooklyn entrepreneurs examine scarcity, ambition and the intimacy required to build a business without sacrificing the lives they want.

1h 36m / November 9, 2026 /businesspsychologystartup / Transcript sourced from openai
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Overview

Jeff Greenberg, a former Wall Street economist who now works as a coach and therapist, runs a live coaching session on money with podcast co-hosts Ben and Mark, who also run the company Insider Loops together. He opens with a short mindfulness exercise, then has them ask each other three repeated questions about fear, desire, and appreciation. From there the conversation turns to how their shared caution about spending shapes the way they grow the business.

Key Takeaways

Jeff argues that couples and co-founders have more in common than either group admits. Couples underestimate how much they're running a family business, and co-founders underestimate how much relationship dynamics drive the work.

Both hosts ranked freedom as their top money value, but they mean slightly different things. Ben fears being forced to spend time on work and people he doesn't choose. Mark wants room to rearrange his whole life without explaining himself to anyone. He also names freedom's downside: keeping every option open has made it hard for him to commit in dating.

Jeff frames money work around three pillars:

  • Financial lineage: how money worked in your family
  • Financial intimacy: whether money blocks closeness or creates it
  • Financial agency: how much control you have over your choices

Mark's sharpest observation is that the two of them underprice their time and overprice cash. They'll sink two weeks into a speculative project without blinking but hesitate to spend money on something like ads. He also splits money into three skills: making it, keeping it, and spending it. He thinks they're good at the first two and weak at the third.

Ben shared an early memory of tossing coins over a mall railing at about age 10 to show off to friends. He now feels shame about it and suspects he has swung too far toward caution. Mark adds that starting something from scratch feels safe to them because they control every piece of it. Growing past that point means handing real responsibility to other people.

Jeff pushes back on the assumption that they're missing something. Not wanting venture-style hypergrowth may be a legitimate choice. He points to the economics book Small Is Beautiful and the fable of the fisherman who already has the life the investor promises him after an IPO.

Practical Steps

  • Try the repeating-question exercise with a partner: "What are you afraid of with money?", then "What do you really want?", then "What do you appreciate about me?" Say thank you after each answer and ask again to get past the first response.
  • Have each partner name the monthly amount they need to feel they have enough. Any experimentation budget should sit above that line and never dip into it.
  • Write a hard-times protocol before you need it, and agree on the drop in revenue that triggers it. Jeff suggests using whichever partner's threshold is more cautious.
  • Treat new bets like poker. Pay enough to "see the first three cards," then decide whether to keep going. Ask your partner to hold you accountable when you avoid a reasonable bet.
  • Schedule regular appreciation instead of waiting for an outside facilitator to prompt it.
  • Look for things you want but won't pay for, like an in-person retreat or the Hoffman Process (a week-long personal development retreat Mark has held off on), and budget for them on purpose.

Notable Quotes

"I think we underpriced our time, but overpriced cash." (Mark)

"Every time someone asks for the ticket on the train, I will be able to give it to them and not be kicked off the train." (Ben, describing what money security means to him)

"What does it mean to not have money... be an obstacle or barrier to contact or the flow of love or connection? But actually it's something that's a vehicle for closeness." (Jeff Greenberg)

I think we underpriced our time, but overpriced cash; we’re okay trading our time, but it’s way harder to trade our money. — From the episode

Full Transcript

Source: openai 1h 36m runtime

All right, we are live. Jeff, thank you so much for joining us. Thank you for having me. We were talking in the pre-recording about how we have to start recording this because at some point we just need to capture the conversation. But what we were talking about just before recording, hopefully this just feels like a continuation of that. I've been really looking forward to this conversation. We're not going to do a big intro for you. We'll link in the show notes to people if they want to like learn more about your background, You are definitely someone I've really enjoyed getting to know over the last six months or so here in Brooklyn. And we were talking over coffee, I think last week, about how some of the work that you find really enjoyable and meaningful is working with sometimes romantic partners, sometimes business partners, and helping them better understand each other's relationship with money. And I was telling you, this is actually a topic Mark and I haven't properly done a deep dive into yet, just with a coach. We've talked about some money stuff at the surface level, but I don't think we've gone deep and done work on it. And so I asked you if you would be willing to come and do a proper co-founder coaching session for us on air. And I don't know if you're the brave one or we're the brave ones, but all together, we're doing it. So that's how I want to kick this off. And then I want to give you the mic and basically have you do your thing. Where do we start? Yeah. Yeah. So we talked about doing some mindfulness. And why do we do mindfulness? I think of it as so much of us are rushing through Slack messages and other things. And when I meet with an individual or a couple or even a group, I think to synchronize, to remind ourselves of who we are, to remember our bodies, to do all these things, even just a good breath or some stretching can be this opportunity to remember, right? I think of mindfulness is very much that, it's not some great achievement of like clearing all the thoughts of our mind, but it's just this coming back. And that can be being lost in thought and coming back, that can be just being in a meeting, having a moment of pause. And so the opportunity to do that together, I think can even be more potent. And when it's related to money, you've already said, it can be a pretty courageous conversation. And then to do it in this fishbowl witnessed by people can make it even feel more courageous because we're doing something radical by talking about money just openly, right? To not hide it or talk overtly or only talk about a sliver of it. And so that's what I'm going to guide now. And so if you're listening to this, it's an invitation to find a comfortable seat or even lay down and just allow yourself to notice. Ben, Mark, you're welcome to close your eyes, but with any meditation instruction, there's never pressure to close the eyes, right? We're regulating ourselves. And if you're driving a vehicle or something, definitely don't close your eyes. But just allowing yourself to notice, witness, and you can stretch out the body too. So sometimes when we slow down, we notice that we've been holding the body in a strange posture all day, or the keyboard posture has been pulling the shoulders forward. So pushing that back. And so we're just noticing and watching and witnessing just this process. And all the words I use are very passive. They're about allowing and receiving, and I'll use words like invitation, just to be with things as they are, just as they are, right? And so many other parts of our lives, we're trying to get shit done or do a task, and it's very doing mode. And so what would it be like to shift into being mode? Just allowing the breath to be breathed. And as I draw attention to the breath, noticing it first, and then breath oftentimes the object of attention, just allowing it to deepen more fully, feeling it in the belly, in the back body, holding, and then nice extended exhale. And that can be audible. Hearing yourself exhale can be a nice cue. And we're just going to do this for a short moment, just to allow ourselves to shift into a state, and the three of us shift a similar state. And again, just a nice full inhale in through the nose, feeling the belly, feeling the expansion, holding, and then long extended exhale. And the mind can have its chatter. You can notice physical sensations, places of discomfort, ease, and just noticing them and relating to them softly, and letting the muscles soften, and letting things hang heavy, and hopefully finding more stillness even amidst that that chatter. And from here, I just want to surface this notion of money, right? So money and everything that's connected to money, and wealth, and finances, and investments, and debt, and mortgages, and returns, and investors, and burn rates, and all of this constellation of words. All right, so just taking those in. And as you do that, noticing any shifts in the body, right? There can be feelings of bracing, or power, just noticing what any of those evoke. And they can just be felt senses, or symbols, or concepts. Just noticing where all of that sits. And again, not having to do anything with it. And next, I want to just tune into a felt sense of enoughness, right? A lot of money circulates a little bit around enough. Do I have enough? Will there continue to be enough? Am I enough? Right? All of these enoughness questions. And just see if you can allow, even if temporarily, a feeling of enoughness, of sufficiency, that in this moment, the three of us sitting together, or where you are listening to this, some sense there is enough, right? You have just enough in this moment. Enough oxygen to breathe, enough food in the belly, enough hydration, enough presence to hear my voice. And just allowing that enoughness to spread throughout the body. Again, just noticing any physical sensations, and being with whatever emerges. And that can also be resistance, noticing any resistance to this. Maybe the enoughness is hard to contact, and honoring that resistance too. And here, to bring this to a close, just noticing anything relevant that might have emerged in our time sitting briefly. Holding on to that relevant pieces, if you want to scribble anything down, doing that. And then letting go of all the rest. And Mark, Ben and I will wiggle the fingers, wiggle the toes, make our way back into this shared space together. And if you're open to it, so Mark and Ben have provided answers to some questions in advance of this, but I thought we could do a version of repeating the practice that I mentioned. So it'd be three questions, and we'll take turns answering. So the first question is around fear, the second is around desire, and the third is around love or enjoyment. And so the questions that I'm going to instruct Mark and Ben to ask each other is first, what are you afraid of when it comes to money? And you'll ask the question, the other person will answer it, you'll say thank you, ask the question again. We'll do that for a couple of minutes, and then switch from what are you afraid of to what do you really want when it comes to money, right? What are you longing for, what are your desires when it comes to money? And then the third part brings us more into what you're doing together in the relationship, and an opportunity for celebration and love and honoring the co-creation, which is what do you enjoy about working with each other, right? Kind of bring it all back together. So are you open to this practice, Mark and Ben? And that's a way to start it if you were to do this. And this is an adaptation of a couple's practice, which might be, what are you afraid of? What do you really want? Why do you love me? But we're adapting that to this context. Mark, are you going to make a joke? I was going to make a joke. Mark's like, we should just ask, we should ask, we should ask that question. Carol, if you're listening to this, you know, just want to make sure that my intentions are pure. Although I think she does joke that we're each other's work husbands. So I think we're cool. I mean, I was saying to Ben, the difference between couples counseling and co-founder counseling is pretty limited, right? And I think couples underestimate the extent to which they're running a family business together. And then I think co-founders can underestimate like how much the relationship dynamics impact the whole project, right? So I'm just like, I think there's a lot to cross-pollinate there. All right. So here we go. Mark, you can start by asking Ben. Yeah. What are you afraid of when it comes to money? And I'll keep time and I'll say, let's go. Cool. And Ben, what are you afraid when it comes to money? I think for me, it's very simple. I am afraid that I will need to spend my time on things that I don't want to spend my time on and spend my time with people who I don't want to spend my time with because I need to do those things to have enough. And I think the topic of enough is, I think, something that we can talk about later in the conversation. I know it was something I was thinking of in the exercise. But yeah, I think my biggest fear is I just have to do things and spend time with people I don't want to do and spend time with. Ask him again, Mark. Say thank you and then ask him again. Thank you. Same question. What are you afraid when it comes to money? I don't have a different answer. Maybe you could, Jeff, can you remind me what we're supposed to say differently this time? Anything. Just keep digging deeper, dig to different terrain. What could go wrong? What do you notice? Yeah, I guess maybe I'll give you a more positive. So if I told you what I'm afraid of in the more negative sense, like what I'm worried that the need for money would force me to do that I don't want to do, I'll kind of share a more positive one maybe, which is I'm afraid that due to money pressures, I won't be able to maximize the time that I spend with people that I want to spend my time with and doing the things that I would like to do. I think that's a good segue into what do you really want, which can oftentimes be the mirror image of those. What do you really want when it comes to money? Mark, you can ask that. Yeah, thank you for sharing that. Ben, what do you really want when it comes to money? I want money to enable me to spend my time the way that I would like to spend it and with the people that I want to spend it with. At the most fundamental level. Everything else is a double click, I think, into that. Thank you. Yeah, sorry. Sorry if that's light, but it just feels like anything else would be like fleshing it out more, you know? Yeah, I did feel like you were editing yourself, like you wanted to say something and then you stopped. So I would encourage you to go there. The imagery that was coming up for me as we're doing our exercise, which I held on to, which I'll just share, is there was this image for some reason that came into my mind, probably often as it happens for reasons that maybe I don't know exactly why, but it did. And the image that came to mind was sitting on a train and having the guy or the gal who checks the tickets come by and feeling like I will always have a ticket to give that person. Don't know why that was coming up for me, but that's what I was going to add, is this idea that as I move through the world and do the things that I choose to do and go to the places I choose to go, that every time someone asks for the ticket on the train, I will be able to give it to them and not be kicked off the train or accused of riding illegally or something like that. Beautiful. And then we'll finish with, what do you enjoy or what do you love about Mark? A lot of things, but I would say, so I'll talk directly to Mark. Mark, what I love about you is that you are, I think, committed to living a very authentic life that is like your life in an intentional way. And at the same time, having a very rigorous, like I really do value strong work ethics and I think you have an incredible, like I love your work ethic. I love the way that you're disciplined in ways that I'm not. Like you have the ability to do things consistently, which has enabled me to show up more consistently and to kind of like develop more discipline in my life. And I definitely like really appreciate that. I also think that you're committed to like your health and putting health above all else. And as someone who myself is trying to get healthier, that's been a very positive influence on me. I also really love your emotional maturity. I think that I can sometimes be a little like, you know, we'll get a negative customer email or we'll have something go wrong with like one of our work things that we do. And I might, I don't want to say spiral, but like I might go into a little bit of a negative place. And I think you have an ability to bring a lot of objective, you know, kind of discernment and find a productive path forward that maybe I wouldn't be able to get to on my own in the moment, maybe after sleeping on it. But like, I feel like we can get there much, much faster together. And lastly, at least this last thing that's coming to mind right now is I love that you have consistently encouraged me to, you know, bring more of my creativity to the stuff that we do together. So I feel like our relationship in a lot of ways has been a really nice vehicle. Like you don't say no, like a lot to like the things I propose. You always, like I feel like way more often you say the yes and you get excited about the things that I bring up. This podcast, starting Insider Loops together, like these big things that we've chosen to do together, I don't feel a lot of resistance. I feel, if anything, kind of like an excitement or a desire to accelerate maybe even, which feels very motivating for me. So yeah, those are some of the things that come to mind. Super beautiful. Thank you, man. Wish I could give you a hug. Yeah, this practice should end in a hug. So hug yourself to the extent you can, which they say releases similar types of oxytocin and things like that. Yeah, yeah. Right back at you, brother. Ben didn't, Ben did not hug himself. I, I was, I was, I was doing a tummy, a tummy hug down here. Lower, lower hug. Upper body hug here. But yeah, like I think both the giving and the receiving, letting that wash over you. I'll say it's just nice. It's nice to say, I mean, I know I've told Mark a lot of that before, but it's kind of like, it doesn't feel any less nice to say it again or to say it in this, in this setting. Like it feels, hopefully none of that was a surprise, Mark, but like, yeah, it does feel really good to say those things. Yeah. I was saying the same thing. I was like, oh man, like we should do this more often. Like it just feels nice. Like I felt the same way when I was like writing my answers last night of like, man, this is like, this just feels good. Right. And it's almost like what we like to repeat in the podcast. It's like what you appreciate, appreciates type of thing. And so, so yeah, strong, strong plasma on there. Does it feel okay to, to, for you, Mark, to answer the same questions? For sure. Keep some symmetry. So Ben, now you ask him, what are you afraid of? What do you fear? So Mark, what are you afraid of with money? Yeah, I would say to me boils down to two things and freedom and regret. So freedom, I just don't want to lose my freedom. Like I actually, in a way I feel like in a lot of ways I have enough right now. And I just know that I need to, you know, keep making money to like be able to sustain this freedom. Right. And have the optionality because right now like this freedom is like, Hey, there's something that I don't like in my life. I have the ability to change that. And that is like beautiful. And then the regret is that I also feel like I'm in a very unique point of my life. Like I'm healthy. I have a lot of freedom. And I'm just like very aware of the finiteness, finiteness and like uniqueness of this point in time. And I don't want to deprive myself from experiences today because I'm so focused on creating optionality for tomorrow. Thank you. I can ask again, right? I can dig. If you want to know more, yeah. At the chance that there's any more to uncover, Mark, I'm going to ask you again. What are you, what are you scared of with money? Yeah. I think I'm scared of like to wake up in 10 years and be like, it was never about the money. Like why? Like it was just stupid, right? Like it's like, I just, there's all these things that I could have done, things that I said no to, things that I thought about. And that was the true kind of like wealth that I had. Right. But I could do all those things. And I had that option, but because I wanted, I just made a trade that was dumb. Right. And I'm like, I traded optionality in the future. I don't even know if it's going to exist. Like for all I know, like I could be hit by a bus tomorrow. And so I'm like banking on things that are just so out of my control versus like I have things that I could be doing right now. But like my rational mind is like, you know, like, you know, you got to be the king of the marshmallow test. Like fucking, you know, like wait, wait, you know, like, like just like, you know, you don't deserve that gratification now, but I'm just worried that I, you know, my aerial self just like won't be able to forgive himself because just I didn't know now how good I had it. Thank you. Thank you. No. What do you really want? So Mark, what do you really want money to enable for you? Yeah. I just want to keep having the flexibility to continue to like learn and improve and refine my taste and then be able to like modify my life based on that. Right. And I think in order to do that without constraints, I need flexibility. Right. And I kind of connect flexibility to money because yeah, I'm like really happy doing what I'm doing right now. And I don't really want professionally, like I don't know if I want anything like maybe you know, making more would be amazing, but like how I spend my days, kind of the energy that I wake up with every morning. But I'm also like, and I'm happy with like a lot of parts of my life, but yeah, I just don't know whether this will be like how my life will look forever. And I know I'm going to have to make changes and I just want to be able to make those changes when the time comes. So I think just like that, like a vehicle for that flexibility is important to me. And yeah, and I think just, you know, I know like there will be some hard times. Right. And I think just like I want money to give me that peace of mind and one way to figure things out without compromising on like that freedom or just doing things that I don't want to do. Right. So I want to thank myself for doing those things and giving away and just making a trade again that my 80 year old self would be like, that was really fucking dumb. And yeah, and I think eventually like, yeah, I want to have a family. So I want to be able to like give my kids whatever my parents gave me and more and doing that without again compromising the work I do and how I spend my time. And also like having the option, like, Hey, like if I want to be a more involved parent, like I don't have to grind 80 hours or a hundred hours. Like I can choose to maybe do 30 hours and spend and be a more present father or husband or whatever that might be. Thank you. Beautiful. Thank you for sharing that. And I can ask this, Mark, what do you love about Ben and you can direct it to him? Yeah. I love Ben. There's many, many things I love about you as a friend, business partner and yeah, human. And yeah, I think kind of like picking it up where you left it off, right? Like I think you, you do have a lot of creative energy. I think you have a bias for action, you like delivering things to the world. And I just feel like I love that the momentum and the energy that that creates. I think that like, it takes me a little bit of kind of, to me, it's harder to kind of get that like initial starts. I think I just work with someone that like can create that environment for me to do the best work. It's really nice. And I also like really appreciate like your high bar for craft and quality. Like I just like really trust it. And I know like whatever we do together is going to be great and strong because you're just kind of like always kind of on watch for that. And I also love that like you deeply care about the people that we serve and like making sure that we do a good job at solving their problems. Like it's like, it's not about just like getting them to buy our stuff, but like, yeah, how do we help them win? And I think like just seeing how much energy you get from like almost, yeah, almost like feeling their wins as like they're your wins and almost like in a way, sometimes I feel like you have more pride of their wins than your own wins. And although sometimes they're the same thing too, but in a weird way, right? And so yeah, I love, and I feel the same way and I love that we share that and that like we're like super aligned. And yeah, I think also you're very like emotionally mature, which I think makes it easier to just have hard conversations. Like I know like we'll show up in a hard conversation and maybe like, you know, we won't get to the desired outcome or to like a resolution right away. But I know at least we'll be able to have that conversation, we'll be able to navigate it. And like, like it just, I just can trust the process, like it'll work out right eventually. And there's like, like a peace of mind that comes from that. And I also really admire how like, I think you're world-class at communicating, like especially communicating, like what you need and kind of where you stand on things. And I think that like has pushed me to be better at that. Like I think you've like, you're just, yeah, like it's always very clear where you stand. And I think that's always like, just adds a lot of clarity. And sometimes like I feel like a lot of, in relationships, a lot of energy gets lost in that ambiguity. And I feel like there's very little of that in, in our partnership. Yeah. I also feel like you're just a great human, like, and I'm like, I feel like a lot of times like I think you, you get to experience the quality of the human, but like part of it is like how you feel cared for someone, like, like I definitely feel cared for from you. But also I think from like the people in your life, like I feel like one of the cool things about this podcast is that I've gotten to meet other great humans in your life and like Jeff, for example, like, and I think that's like a really cool and to see like, you know, to get to know you through that part of your life. And so, yeah, I just feel very lucky to do this work with you in a way, like I feel like we're also like aligned in so many things, right? Like the way we, we want to build our life, the intentionality that we just not put in work, but like family and health and flexibility and like don't really. We just question things and we just don't really take any like status quo for granted. And I think it's like cool to be like exploring the map on its full fullness and, you know, without any constraints. Thank you. And I'm also sending you a hug. Yeah, very, very nice. Yeah. And apparently, and I got a text while that, well, my dog wants to come in the room. So I'm letting my dog, I promise I'm full. The other part I'm appreciating, you know, beyond money or other things is one of the things we're modeling is just like male intimacy, you know, like men being loving and tender. So you know, like if there's a ripple effect from this, it's like, ah, men can speak to each other this way, you know, you know, the other kind of core of my work is doing men's work and men's groups and men's retreats and other things. It's like creating space, like love to flow between men in a way that's, there's this, I think, deep longing. And then when you hear like, oh, it's so nourishing and beautiful and, and it retains this masculine kind of like drive too, that has a different texture to it. I think we always, I think we've always, I mean, this is one of the, first of all, like I definitely agree. I think of, you know, we're not like Jocko Willink, you know, testosterone, gym heads, Navy SEALs or something, but like, I'd like, I'd like to think we both have pretty healthy masculine sides. And I think that Mark and I have, whenever the choice has been to be vulnerable with each other or to kind of like try to put on some front or some kind that's like put on the armor. I think we are both very good at kind of showing up with the vulnerable energy. And I think that has only brought us closer together and like helped us gain respect for each other. So I think, you know, we don't really subscribe to like needing to show up with like armor on to be successful and, you know, like have good relationships or anything. I think it gets in the way. Yeah. And it, I think it takes one person to model it and then reciprocate and maybe another to take it deeper. And, you know, you're like, Oh, we could just keep going. It seems like you to have a pattern of deepening further into it. And in the context of this work, you know, I've been thinking about like, what, what are some of the pillars of this that we're doing? And so there's the historical or the origin myths and things, what happened in our family, which I was thinking of as financial lineage, right? So like, what was, how did money exist in our grandparents' homes or great-grandparents, right? And feeling that, and how are we inheriting? But then this other more present moment is what's financial intimacy? What does it mean to not have money finances be like, be an obstacle or barrier to contact or the flow of love or connection? But actually it's something that's a vehicle for closeness, right? Which is, I think, a radical reframe. And then the third piece, which you two both circle around, which is, I think it is financial agency as a third pillar. And both of you in the, I had nine values related to money and both of you chose freedom as number one. And so I think of, and the way that you both talked about it is, and I'm curious what you heard about it, like what freedom actually means to you, but a lot of it is agency over your time, over who you're with, how, you know, where you decide to turn or not. And in prior episodes, you talked about like, do you work for someone? Do you take outside money? You know, all of these things are like compromises of that agency or freedom. And that resonates, like, yeah, yeah, Mark, I just wanna share one thought that came to mind, a connection, as Jeff was talking, and then I'm curious to kind of hear what's coming up for you is, Mark and I both kind of expressed some flavor of like wanting the agency to not do things we don't wanna do. And in the pre-recording, we, I'm connecting the dots with something we talked about, which is trying to kind of like tune in to like what's in the body versus what's in the mind. And to me, those, so I'm gonna make a connection there, which is like the freedom to like follow what's in the body and to not do things that feel wrong in some sense, because of the money. Like I feel like those concepts just became kind of like connected for me is like, because in the past, just like contrast that, you know, some high paying roles I've had don't wanna lose my income tied to a single employer, some executive or someone really important is asking me to do something, I feel like it's not the right thing to do for whatever reason in my body. And yet, I have to, or I have to deal with all of the implications of saying no to that, which can sometimes be very destabilizing, but if I rely too much on that one employer for my income. So like that was just what was coming up for me is like that kind of stuff. Yeah, and I think for me, that's part of it too, like I think just like having a freedom on like, on the work itself, like what gets done, how work gets done, who do I work with? Like that is very important, but I also think like the freedom to kind of rearrange the different parts of my life in any way I want, right? Like, you know, if I want to go to the gym at noon every day for an hour and a half, I don't have to explain it to anyone, right? Or if I want to like, spend time with my family from 10 to 11, or spent, you know, like visiting my family in Spain, like, yeah, I just want to never have to think too hard about making those things that like, I feel like feel the right thing to do at that point in time. And yeah, and I mean, I'm sure I could feel like I could find, you know, a flexible employer, but I think there's always going to be like that, like, it just, I'm a firm believer that, you know, like, if you want to do more of something in your life, just trying to remove as much as friction as possible between you and that thing. And I just think right now, like, that's what that freedom gives me, like, any friction like it's my fault. I'm just like telling myself a story, but it's probably not true, versus I think it's much easier back to like my head, like I always rationalize things like, hey, like, if I'm doing this thing, like, it's much easier to rationalize, like, hey, like, I might be like shooting myself in the foot for that promotion, or I'm letting the team down. And or, you know, like, I'm comparing myself to someone who has the same role, maybe different part of the company. I'm curious if I can challenge you each a little bit, knowing each other values freedom, and even knowing that there's some, there was kind of security for you, Ben, that you named as a top two value. And both of you, if I can draw from the surveys, have mothers that are pretty conservative with money. And so we can deepen into that. And I'm almost wondering if you have wishes for each other to fuller express your freedom, knowing what you know about each other. That's a tough one. Like if I can just riff on it for a sec, like as far as I can think of you, Mark, I think you, health-wise, I don't think there's anything else I would wish for you to do beyond what you're doing. I think you're doing all the right things, taking care of your body, and like, I can't think of pushing you more there. I think in your family life, I know you take every chance you get to spend time with your family. You take a lot of time, you visit each other, you go to the important events like graduations and stuff. They come and visit you, like you host them, like you're super, you're a very present. Jeff, I don't know if this was in the survey, Mark has three siblings and he's the oldest one. And so he's like, you know, very caring and loving, like older brother to them. And I think he's really good on the family front, as far as I can tell. Work-wise, I don't think it's possible for me to imagine Mark, you know, expressing more agency at work, given that he's basically running two companies of his own at the moment. And making hiring and, you know, firing decisions and like, you know, he recently made a really big hire for Supra, that has been a very, like, intentional lifestyle design decision for him. This podcast is like a ultimate expression of flexibility and freedom. I mean, this is kind of like a freedom flex in a way, like running a podcast the way we do. And then, yeah, I'd say like romantically and personally, you know, I know how we're not going to get into that, but like, I have all the reasons to believe you're using your freedom to really find the right person and the person to like settle down with and be with. And so I don't think I would push you any more on that. So yeah, Jeff, I don't know if I have a good answer for like something on push Mark to like express more freedom around at the moment. Did I? Mark, am I being too, am I being too, am I letting you off easy? Did he miss anything? Yeah, I mean, I think, I think there's a couple of things that come to mind, I think. And I think it could be. I think I struggle disconnecting, like fully, like in a way, I've, my day, it feels like so balanced that like I don't really need to rest because I'm like, like that's factoring into my day, like go to the gym, sauna every day, get eight hours of sleep. But I do feel I'm really bad at like taking like vacations, like I haven't really taken like a proper, like more than like three days since like February. And for example, and. What do you define as a vacation, by the way, Mark, like if because I have seen you take trips, you've traveled, you've spent time, you know, remotely where I, where you're clearly not working on Slack and obviously with my full support, of course. But like, what do you feel like is not, what do you feel like is a vacation? Yeah, like probably like doing nothing for like more than a week. I feel like I've taken like, you know, like Monday, like, you know, Thursday to like Wednesday, right. And then like maybe one of the days I do check in. Like, so like I feel like I don't fully disconnect. That's one thing that I just like feel like I could probably use my freedom for more than that. And I think the other thing I could probably have the freedom to spend more on the things that I like so I can go deeper in practices that I care about, like fitness or health and things like that. And then in a way, like kind of freedom has like a superpower and a shadow. And I think like the shadow of freedom has showed up in my dating life a lot because I feel like it's hard to commit when you keep optionality open. Right. And for some reason, I'm okay committing on like business things, projects, but like dating is something that just feels like way more scary in a way because I just feel like the weight of like, you know, having a little human with someone and the consequences and the tide that that like puts you to someone, I think like just has been probably hard in a lot of ways. So I think like that's like, to me, it doesn't answer your question, but I think it's like a side where I think my freedom has maybe hurt me more than helped me in that area. And so I'll pause there. Yeah. Yeah. And Bert and you brought in the optionality because it was something that came through in your responses, like money as preserving optionality, every possible future. And yeah, part of what you're saying you're longing for is like agency, but with some maybe like constraints or clear, clear North star or something that is embedded in freedom. But yeah, two of the things I was thinking of is like travel, particular types of travel or like skill building or other things you kind of mentioned, like investing more in yourself in a particular way. By the way, I didn't know that's new to me, just to be clear, like I don't think I've ever heard Mark express that like there's more you want to do on the health side, but you're like holding back from doing, you know, like, so that was interesting to hear you talk about that. Yeah. Yeah. I mean, I think it's just like anything that I care about or that I think it's important that's going to help me be the better version. Like. There's no reason not to, like, I'm just like I have a deep belief that there's no reason to like not do anything you can right now to be better. Right. Like, like another thing, for example, like I'm like, I have three friends that have done the Hoffman process independently and I'm just like, and I just haven't really given myself permission to do that. I can afford it financially, but just also like seven or eight days of like full disconnection, no phone. And so that's like another thing that I'm like, you know. You should definitely do that. Now that I know that you want to do that, like we should like we should get you to do that. And I can like cover for you and stuff for sure. Like it's no problem. Yeah. Thank you. Whenever the timing lines up. Should I do Ben? Yeah. Do you want to flip it back? Yeah. How could Ben be? Based on what you know about him, like expressing his freedom more where money is relevant in ways that might be even, he might be holding back from himself. Yeah. And. Yeah, I'll do. I'll do a similar kind of like process one at a time and. So I think one thing that I think, but like, that's kind of what we got into in the beginning, like I think Ben is a very creative person, right? And I think the work that we do has many options to be like creative, but I almost wonder if like, I think sometimes I feel like a tension between like something that is like, I don't know, I don't know, I don't know, I don't know, I don't know, I don't know, like high ROI versus like something that's just like creative for the sake of being creative. And like, like, for example, like. And like, like, for example, like, I know you love writing, right? And in particular, I think you love writing like long form, right? And I feel like you maybe don't give yourself permission to do that, because it's not clear like what the return on that, because it takes time, right? Like it's like to write a good long piece. It's not just two hours or three hours, it would be 10 hours. And I feel like there's always the cogs in your head is like, hey, like, is this the highest ROI thing that I could be doing with my time right now? So that's one thing that kind of comes to mind of like, sometimes just like, and which was intention was like, the whole point of not being at a job is that you can decide what you do with your time on the creative. And I'm like, what do you Yeah, I'm like, how do you like and what is, you know, what gives you joy and what gives allows you to be the full expression of yourself. And that's like an example where I'm like, you know, it's okay to sometimes not. And I think like, for example, this podcast is like the opposite, like, for the longest time, you know, like, it's not clear what the business value of doing this thing was, but like, we knew, like, just the non tangibles were just so worth it, right? Like the fact that we got closer, that we got to talk to people that we liked, and the fact that we like had this routine consistency, something like, like, whenever I feel like you're in that situation of like, I'm not sure this ROI, like, just I think, probably remembering, like what the podcast felt in the beginning could be, could be like a helpful reminder. And yeah, I mean, I think something that maybe like come to other sites, and that's been really cool to watch, and like an evolution from when we started, is like how you've invested more heavily in your health. And like, I think the fact that you've like decided to get a personal trainer, and like do more of that, like, I think like, just like, I feel like there's probably more you could do that in other parts of your life. And like, I think like, the benefit is so clear. I just feel like from a motivation point of view, from the gains, from like, just how I think that probably translates to other parts of your life, the energy that you have with work, with family, like ability to do more things. Like, I think that's something that I feel like, yeah, I think knowing you, I think you need, like, almost like data points that kind of affirm that, like, that this is a good idea. And I think just like using those historical patterns, I think can be really helpful. And then something that I think you already do a great job is like, trouble with your family, spend time, like with, you know, Carol's family, your family, taking vacation, traveling with Gaia, I think like, just keep doing that. I just feel like it's feels like bring so much joy to you, to Carol, to like, and it's such a cool, I think, just adventure that you get to do that with your family and kind of almost feels like when you do that, you transport like home to whatever part in the world you are. And that's like very beautiful. And I'm like, every time you do that, I'm like, man, that's cool. Thank you. Thank you. Yeah, yeah, I'm very fortunate. I feel very grateful, I guess, right now in this moment, just here, that's what's coming up for me as you talk is like gratitude for being in a position to either act on what you're saying I could do better, because I think there's a lot of good stuff that you mentioned and, and or just gratitude for the ability to do the things that you're already describing. And see, we can savor it for a moment, just allowing yourself to savor that. Breathe into it. Ben, some imagery, the train and thing you shared in the survey, and maybe this relates to your father, parents, but this idea that things are good now. And I don't know where the train fits in exactly, but this kind of feeling of like things are so great now, but it might have an end, you know, like, or inevitably, almost like the good times imply that there will be a bad time. And that was unique to your responses, Ben. So I'm curious if that shows up, like as you almost savor the goodness of your life, the sweetness of it. I want to take a moment before we get back to the episode to tell you about Insider Loops. This is a company that Mark and I started because we just believe this should exist. Companies should be offering candidates the best possible preparation for their loops, yet what they give them is vague and often not very actionable. So we took the matter into our own hands. We've put together well-researched and continuously updated guides for PMs and reviewing at companies like Anthropic, OpenAI, Google, Stripe, DoorDash, and more. If you're getting ready for PM interviews at those companies, go over to insiderloops.com and learn more. It's a lonely time to be a product leader. The role keeps changing, there's AI hype everywhere, and people look to you for answers. And that's why I created Supra, an invite-only community for senior product leaders and the partner of this podcast. And fun fact, I met Ben when he joined Supra. When you join, we match you with seven peers at your level and company stage. You can be honest about the problems you're facing and learn from people who've handled similar challenges in a fully confidential space. That can help you get to a solution much faster. Learn more at joinsupra.com. Now, back to the episode. Yeah, yeah, it does. And I, you know, like, sometimes it feels like this chapter, it's coming up on, I guess, like, three years outside of traditional full-time work, end of January. And, like, sometimes it feels like this chapter has been characterized, like, at every moment in time, I've asked myself, how does it feel now, right? Now, I'm not saying how it feels in hindsight. I'm saying if, but if I look back and I try to remember, and this is still how I feel right now, is it's always been characterized by this feeling that, like, I'm pulling off, like, a high-wire act and I, it can go, it could, it could just, like, end at any moment. Not, like, getting hit by a bus health-wise and, like, although I'm very keenly aware of the finitude of life, and that sucks too, but, like, it always feels like I'm one week or month away from, like, revenue going to zero, like, you know, like that, or, like, I don't know how I'm going to make the money next month, and the truth is, I don't know how I'm going to make my money next month, and that's been the same way this entire three-week, three-year period, and so, yeah, like, when the things are going well, I, I appreciate it, and Mark and I celebrate all the time, like, you know, I think we're really good about that, and then when things are not going well, it's, like, this, this narrative, this voice can creep in and be, like, you know, like, you know, it was inevitable that, you know, like, that was, that was great, but, like, it was inevitably going to come to an end, and then a lot of what I do is try to, like, spend my time battling that atrophy or that, you know, that, the force of gravity, almost. It almost feels like if you look at, like, a revenue chart, not just to bring us to numbers for a second, it's like the x-axis has, like, a pull, like, a gravitational pull to it, and then the y-axis is trying to, like, escape all the time, and so it feels like the only way that the y-axis gets away from, like, the only way that the distance for that line grows away from the x is if, like, I do stuff, and, and if I don't, and if I don't do stuff, it's just gonna come right back down to zero, so, and then the story I tell myself is if that does happen, other bad things will happen as a result. Can we go, can we go back to the high wire? So you're on the high wire, where is Mark in the scene? With me, probably right now, yeah. So you're up there with him? Yeah, and I'd say that's, that's a re, that's, like, as of the last, you know, few months, it's felt like that, but I'd say, because, you know, yeah, because Mark and I have really kind of, like, committed, committed, I'd say, in the last few months to, like, really, you know, this next chapter of Insider Loops together, but I, I feel like leading up to that, even for the first few months of Insider Loops, it has felt kind of like I'm up there mostly on my own. Mark, can you picture yourself with him? How, how far down does the ground feel for you, Mark? In which way? Downward. You're on the high wire, how far is the ground? Like, if you fall, how far do you fall? Yeah, if you fall, how far do you fall? Um, it's funny, like, it depends which part of my body answers. Hmm. Yeah. Yeah. Maybe answer from, answer from different parts. Yeah, I would love that. So my, so my head is like, it's going to be okay, right? Like, like my head is like, you know, like you have some runway and, you know, assuming, you know, something, something bad happens to whatever you and Ben are building, like that will, that could vanish. But what will not vanish is the skill sets that you've built, the audience that you have, the intuition, what, like all those learnings with enough breathing room will allow you to create those conditions again. Like, like I, I like deeply believe that in my head from a rational perspective. From a body perspective, I think there's a little bit more fear of like, and the fear is twofold. It's like, man, maybe I got lucky a couple of times. And like, you know, it's like, there's like a little bit of imposter syndrome and like, and like, you know, maybe what if I cannot crack it and I have to get a job? Like, it almost like starts, like, there's like this fear of like, starts spiraling and fuck and what, like, maybe I need to get it like a job, but like a Google and a meta and like, be, have those golden handcuffs and then like, you know, wake up at 50 and, you know, be like the senior director of BP and, and a zombie. And then just like, man, you just, it was all because you took that fall and couldn't figure it out again. And which is like, you sounded out loud, you said a lot, I was like, man, that, that you sound like a jerk and a douche. And I hope I don't offend anyone like that, but that, that is kind of what I'm feeling. And, and so, yeah, I think there's like that. And then also I think like, sometimes part of me just worries about like, like how Ben and I could navigate that like downfall, like in a way of like, like both, I think like both kind of like feeling that individually, but at the same time, like how do we regroup and build that together? Right. And like, and, and giving ourselves the grace and the spaciousness that I think you need when something like that happens. Cause I think like, I think in general, like I think a pattern that we both have is that when things get ugly, we both go in back into like a scarcity mindset, right? Of like, Hey, like, you know, we need to protect the downside and we need to like lock everything up so we can kind of like, like basically like stop the loss. Right. While also like doing everything in our power to like, you know, get this puppy back in, in the upward trajectory. Right. And I think, I think in general, like I, I'm, I've always been like fearful of like swinging big when it comes to like my own money or my own, like, you know, business, which is like, it just felt safer to, you know, like incrementally increase and get better as opposed to like, just like, you know, bet the house. Right. And then I think part of it is like, it helps me a lot to sleep better at night and that has a price, but I think part of it is just like, I think like probably some money stories deeply ingrained in my family. And. There's, there's so much richness in there and I think Ben you're also eager to speak too, but I was wondering if we'd get to that point, which is, yeah. Under stress, you both seem to enter a similar but different mode of, of, of navigating that kind of scarcity or, and, and yeah, you could see that in the co-founder being like, who, which one is, of us is going to hold out hope or, or particularly growth, right. That seems to be, you know, if there was maybe a missing piece of the co-founder, it's like, you both seem to be very interested in momentum, but maybe there's less of like the expansion voice. And so both on the downside being, and then being like, how might you dial that up knowing that it's like not part of, let's say your lineage? This is our, this is definitely our biggest shared growth area that we talk about openly and we have started to invest our time and like thinking more about like distribution and growth. And I don't think it's a, I don't think it's a problem of like, that we don't have like an abundance mindset or that we don't know that there's like a lot more or that, um, that we're not like injecting energy to get escape velocity. Like it's felt kind of to us, like we, we just don't literally know what it means to like be world-class at like growing something that's working. Right. Like we, like, at like a crazy velocity, like, like Mark said, we know how to do it incrementally, like we can always think about the next 10% or 20% or even doubling, but like, as it pertains to like big swings, like I think one of our things we're literally trying to get better at is finding the levers like for being swing, like, yes, let's pull the big swing lever and, and, but to Mark's point, like we're not willing to compromise on like, like the constraints, I guess, are guiding our decision-making is we don't want to hire if we don't have to, we also don't want to raise money. And we also don't want to, um, compromise the quality of what we, what we do. So it's like, we need to maintain quality. We need to maintain team size and we need to maintain, um, call it like control equity wise, like the cap table structure in order for us to feel comfortable, like just, in order for us to like genuinely want to keep doing this. It's kind of how I want to honor. It may not even be a lack, right? Like it, it may be like, we're saying this is some external high-paying VC led narrative. And what's true for you is like this, we we're doing well, we're compounding, we're interested in 10, 20%, we're not interested in these other ones. We, we know the size, you know, and one of the, one of the more potent economic texts for me is called small is beautiful. And it honors this notion that like, not everything has to be growth obsessed, right, if you're like, you're getting your needs met and the trade-off between, you know, what exponential is like on your time, lifestyle, freedom may not also be true for you. Right. You know, like you don't have to, you know, franchise your idea or if you're familiar with that story of the fishermen and the boat where, uh, you know, the fishermen is out there, you know, fish is doing, they plays guitar, right. And the, whatever VC would says comes in, it's like, come grow a big business. And then you can do this and make all this money and IPO, and then you can retire and go on a beach and fish and play guitar, right. And he's like, I think I'm already doing it. So, you know, finding your own version of we get to fish this much. We get to work this much. We get to play guitar this much also is kind of your unique DNA too. So just to kind of bring it back to that. Yeah. And I think, you know, the way I think about money, like there's almost like I mean, I'm probably correct me if I'm thinking about this or not way, but like when I think about money, there's like almost like three skill sets, right. And related to money, there's like making money is a separate skill set to keeping money, maintaining your wealth. And then there's another one around like spending money. I actually feel like probably Ben and I are probably pretty good at like making money and probably could be getting better at making money, but like, I think we're pretty good and we're definitely good at keeping money. I think spending money, I think probably both on a personal side, on business side is something that like, I think we are getting better, but I think it's like a muscle that I think it's still very new. Right. And I think we're, we're starting to see some, like we've, we've taken some early swings that determine, well, okay, this is a good use of time or money. And, but, but I think that's something that I feel like we still don't have enough data points that there was a, you know, in, in business it's harder to, yeah. Because business is so transactional and in a way of like, you know, money in, kind of return out that I think just like, and it also takes time, but I think that's the muscle. Yeah. The one thing I'll add just to piggyback on that is like, in my life, when I think about, like, for example, you brought up the, the, the example of me spending money on a personal trainer, which for a long time was like an idea. Like, I was like, I want to spend more money on my health. But I didn't know the lever. Like, it's almost like I, in my head, I hadn't seen, it's not like I saw the lever to pull and I was like, well, I'm not going to spend it on that. It was like, I don't know what the levers are. And then by, and then one day I got the courage to like walk into this gym and I was like, look, I don't know what the fuck I'm doing here. I don't know what you guys do. I don't know how people like me work with you. I need to get in shape. I want to work with a trainer. What's the deal. Right. And then like that, that just seeing that place, you know, I finally wanted to like grab the lever. I went inside, they gave me options. I pulled the trigger on paying for the options. And then I started to be able to do the thing. And so like what's been challenging for me with our, the growth side of the business is like, I feel like I don't see the levers and I think I'm happy to spend time and energy mapping the area if, if I think it's going to help us find the levers. And, you know, we are, I think it is working. Like we found some, we found like at least one lever that we're willing to like commit to paying on a monthly basis starting this month. But, um, I want to get, I want to continue to get good at kind of like that skill of like mapping the territory and being able to like waste, you know, some money realizing there's not a lever in this part of the map. Right. And like, yeah, yeah. But I think the, the hard part about that is that you can not know what lever works without kind of paying for the lever. Right. So it's like, it's almost like being like, Hey, like, I want to find, I want to find the perfect wife. And you just like, look at women walking around the street, be like, Oh, she, like, you know, she could be a good one. Or like, like you got to date, like you got to, you got to go a little bit deeper with the lever and like have like a little bit of back and forth to suddenly that's like, I was like, this could be, this could really much get me into, into council territory. But, but yeah, like, I think like you gotta, I think at some point you just like, you know, you get a, yeah. And dip your toes, your, your, your toes in the water a little bit. And otherwise it's hard to know. Yeah. So then it's like, it's a balance. I'm not saying, you know, all of a sudden just like can like diversify and like start going crazy. I actually think like a poker, poker is a good analogy here. It's like, you want to, you, you, there's the decision to put money that gets you to, to stay in the first hand and see the, see the first three cards. And then there's the money that allows you to buy, to see the next card. And there's the money that allows you. And like, so I'm very happy to put enough chips on the table to like see the first three cards. Right. But that, and I'd say like my invitation to you, Mark, is if you ever think I'm not, like hold me accountable to this. If you ever think that we're like considering an area that doesn't have a guaranteed ROI, but like if we do, you know, make some investment in that area, we'll get to see the first three cards or we'll get to see a little bit of like what's there. I want you to like hold me accountable to making those investments. It might feel a little harder for me to like initiate that, but I've actually found it very. But I've actually found it very empowering, actually, when you've said, let's spend the money on this, because I know you're conservative too. So, like, if you tell me, I'm not saying that you're the, like, I'm talking, I'm more talking to like Mark and Ben, not Mark talking to Ben, I'm equally guilty here. I have this tendency, so my awareness can be like, ah, how you kind of know it for each other, this tendency, which I think is part of the beauty of having two people that can see each other, know each other at times better than, you know, yourselves, you know, like, oh, this is a tendency. This might be an abrupt left turn, but I think there's a connection. And Ben, I was curious if you'd be open to talking about the vivid example that you shared in the intake about, about the shopping mall. Um, yeah. So the story I shared, that's interesting. Um, see if there's a connection. I think there's something. Yeah. If your gut's telling you, let's, let's pull the thread on it. I think there's some treasure there. I think there's some treasure. Um, so the story I shared, it was a quick story I shared in the, in the intake. Um, but you asked us a flavor of kind of like, what's your, one of your earliest memories with money? And for some reason, um, I probably could have come up with other ones if I keep thinking about this, but like the earliest story I remember that like vividly had to do with money was, um, like I, when I was growing up in Israel from when I was six to 14 in the, in the early, the first part of that chapter, I lived near a big shopping mall in Jerusalem and, um, I had a lot of freedom as a kid, like my parents were both like out and about working and stuff. So I had a lot of my own, like after school, I just decided what I wanted to do and my, where my house was like, you know, like a five minute walk from the shopping mall. So it was like naturally a good place to go. It was like a movie theater, video game arcades, like bookstores, whatever. So I would often go to this, to the mall in the neighborhood and sometimes friends would hang out with me after school and we'd go to the mall together. And, um, I remember when I would go to the mall, I never had to think I always had, there was always like money my parents provided, not like lots and lots of money, but like enough money to be able to go and keep myself busy at the mall for a few hours after school. Um, and I would use that money in whatever way, like play video games, like I said, go to the movies or whatever. So, um, I remember in that period feeling such a sense of abundance with money because it was available the way I just described and I didn't have to like think too much about getting it and earning it or anything or working. And I'm at maybe like 10 years old in a story, maybe 11 years old. Um, and I remember I was going to the mall with one of my friends and like, I remember like flippantly kind of like tossing some coins like over, there was like a little like fence that went down to like the parking lot. And I just remember that like, I was like jokingly kind of like throwing some money over the fence. And for, and now as I'm like 36 and I think about that story, I just feel kind of like shame, like that's like a shame, like there's like no part of me that's like proud of that in any way. So when I was kind of getting ready for this, I was like, that's a pretty vulnerable place for me to go. Cause like, I, I truly like, like it's like wasteful and it's also because there were other kids there, there was an element of like showing off like about my money security. Um, so yeah, like I'm curious how we connect the dots there, but like that is, that's, that's an early money memory. Some of it, I mean, I'm curious what's showing up as you retell, but like almost you seem to have a reverence for money and how it's earned and how it's spent now and like, and also being prudent and not being flashy, you know, like in that story seems to encapsulate a lot of what you might feel like repulsed by or something when it comes to money, both like the flippant, you know, demonstration of it not being connected to how it's earned, using it to display, you know, feel better than maybe, you know, it seems to be like a hard, like, whoa, whoa, those are not my values. And yet at some point, you know, in my past, that was part of me. Yeah. Yeah. And I don't think I have anything to add to that, but yes, like that's, that's, that's how it feels. Well, and, and I, as I bridge it to the business, it's like, I don't want to be using it in this kind of like, I'm just throwing it over the balcony kind of way. I want it to be intentional. I want it to be like considered, aware that there's a lever there, you know. That's definitely true. Um, yeah, Mark, I'm curious if anything's coming to mind for you, but like what I was just going to add is just that, um, I might, I might have, my pendulum may have swung too far in the other direction. Um, sorry, which direction? Like, can I like, not like being too conservative, like the thing you said earlier about like the ROI, right? Like, obviously there's no ROI to throwing money over a fence. Um, like, I mean, it's literally like the, the, the, it's like burning money on fire. It's like throwing away, like there's zero regard, zero appreciation for money. I also don't like worship money in the sense of like, I spend, like, it's like the only thing, like my North star in life or anything, but what I mean by the pendulum swinging is like, I do wonder if like there's a little bit of more playfulness maybe with money that would serve me in some way, like, like, you know how like some debt, it may be a good idea, but too debt, too much debt might be a bad idea. Like, I'm, I'm, I'm wondering if like maybe some more playfulness with money would be like something that serves me with my broader life goals. Um, yeah. Yeah. I mean, to me, what's coming up to mind is the, like, in a way, you know, like poker, like there's almost like throwing away money, right? There's like almost then like betting, right. And then like, I think betting is like an interesting, like spectrum, right? Like there's games where you're like absolutely like rigged and it's just like dumb to play those odds, right? Like, I don't know, like roulette, right. And then there you have poker. Buying a lottery ticket or whatever. Yeah. Or buy a lottery ticket. Right. And I think, I think what's hard is a lot of times entrepreneurship is fundamentally a betting game, right? Like you're betting on yourself. You're betting on that this thing you're going to put on money will print more money on the other side. You're betting on our time. And I think what's interesting is, and I think this is actually true for both of us, is that I think we underpriced our time, but overpriced cash, right? Like I think we, and this is just like something that's connecting with, with me, like, I think we're both very okay, like going deep into like a, you know, hole for like two weeks because we think it's a bet, right? And I think, and I wonder if we had like the same diligence on how we spend money on how we spend our time, like if, if things would look a little bit different. And because everything that we do is a bet. And I think the good news, I think we're getting smarter as we get more data. Like, I think like we are able to like have a more predictive model. So it's like, instead of like being a lottery ticket, we're coming more of like a quant hedge fund ideally. And so like, but I, but I think we still need to make bets. Right. And I think we're going to be wrong probably a lot of the times, but we only need to be right once or twice to find something that gives us escape velocity. Right. And I think it almost sounds like as we enter this phase of like, let's play with levers, I would want us to be kind of like, not like, I wouldn't want us to be like, Hey, like the, the conclusion here is that we should stop betting because we took the wrong bet like four out of the last five times. And right. And I think, and I think also like if we learned we're not wasting money, right? Like wasting money is throwing money at something without intention and without and just proper thought and articulation of why that might be a good idea. And so that, that whole thing just came out to me and I don't know why. I love that. Yeah. Like when I, what was coming to mind as you were talking is like, when I think of entrepreneurs who seem to be, again, I'm not trying to get into comparison mode here, but if I think of entrepreneurs who maybe like I admire there was this, like, there, there is kind of a characteristic of entrepreneurship that I strive to, which is to, and this is one of my weaknesses maybe, or like my growth areas as a zero to one person is like, for some reason, zero to one to me always feels very safe actually. And even like one to 10 or something like that, let's call that, if we're, if we're now at like 10, right now, like the, that feels also kind of like safe, but the, the 10 to a hundred is where I'm, I start to feel like I don't know how to navigate in that area. And maybe I, I've been telling myself a story about how that's like a skill set that I don't have, right. Or, and maybe Mark, maybe you tell yourself that story too. I think sometimes we tell ourselves, we just don't have that skill set. We have to pay this tax to like learn from the people that have the skill set. But what's coming to mind for me is maybe it's actually just like continuing to treat, continuing to bring like the, the one to 10 energy with just more barrels almost, you know, it's kind of what's coming up for me. Yeah. Yeah. And I, and I do want to fund and I do want to invest and I don't want to get comfortable and I don't want to get complacent because like the moment we start feeling like our, like the most important thing is protecting the core. We're not in growth mode anymore. Totally. Yeah. Yeah. Two things came to mind when you were talking and I'll try to like, they're like a little bit different, but one of is, I wonder if the reason why we're both comfortable on zero to one is because zero to one is fundamentally a skill set where we control every single element of the experience. And I think we're both fundamentally deep inside, like love control. Like, like, and I think when we go zero to one, like it's our time, right? And I, we control every step of the experience, like how we're connecting to customers is there. And I think fundamentally it's really hard to go from one to 10, just the two of us without any help, right? Because otherwise it's just like, so then it's like, we almost have to enable other vehicles to go zero to one and other things that are going to unlock the next phase of growth and I think that's the part that is just like, there's almost like that trust in the process of like this, we're going to give someone the agency to do that and they're going to do it and also like, Hey, like if it doesn't work, we might just lose all this thing, whereas it just would have been safer for us to do it because we know we can do it and we'll figure it out. So I think that's one thing that just came to mind is like, in a way it's like we're going zero to one on other things and we just need to give it to someone else, you know, in a way. And by the way, yeah, go ahead, go ahead. Say the other thing. And the other thing that came to me to mind, it's like, I mean, I'm not a big platitude guy, but like, it's like, it's like the time in the market beats timing the market type of thing, right? And I think for us, like, I think we're able to do the same thing that we've been doing for the last, like, let's call it like two years for 10 years, like it's just hard for me to imagine that we will not crush it and all our dreams will become a reality, right? And I think, but I think that the part that concerns me is like, times will, hard times will come, right? And then like, how do we stay in the market when those hard times come, right? Like when like, it's like, it's been three months in a down spiral and we're like, fuck, like, you know, like we, like, we can not go down this path and like, you know, we need, we have bills to pay. And I'm like, just like, I'm like, we started getting nervous. I'm like, shit, like, what, like, you know, like, how are we going to turn this around? And so that was, I don't know. Those two things kind of came up when you were just like, yeah. The platitude I would throw in to that scenario is also one of my favorite, which is your net worth is your network or vice versa, which I do think about for the two of you and the reach. And it's like, actually you, you don't, and I'm even thinking about it with the, with the high line, high wire, you know, it's like, oh, what if you're actually held up by all of these people around you that you've supported and they're just standing there being like, try to fall, you know, where they're holding you. And so you can't fall without it being like a trust fall into the people you've served and helped. It's arms. Yeah. And what that brings up for me is I just don't have to rely on other people in that way, you know, like I have this, like, I know that if I ever did need money or whatever, I will, plenty of people in my life care about me and love me enough to like, give me money. But so it's like, yeah, it's, or to give me opportunity even, but I hate asking for that. I hate needing other people in that way and relying on other people and depending on them to take care of me. Like I love being able to take care of myself. So yes, you're right. And yeah, I still don't want to fall edgy. Yeah. You don't have to want to fall. I know. So maybe, you know, knowing they're there makes it less stressful to be walking across. They're just there cheering you on. Yeah. Mark, you were nodding. No, I mean, I laugh because I was like, I feel the same way. Like, I'm like, I know that if I'm in a situation like that, there's plenty of people that just would have my back, but I just like, part of it is pride. Part of it is just like, again, like I feel like if I. Have someone help me. I feel like I'm losing my freedom, but it's like, but it's this like almost like this circular, like, you know, like circle, but then it's like, if I don't have their support system, then I also don't have freedom. So it's like, it's like, okay, like, so which one is it, bro? And keep going. Yeah. I was just thinking there's freedom, right? But also, you know, maybe a different axis is interdependence, right? And so it doesn't need to be like dependent, right? You can be like, all right, we're leaning on each other to the same extent that you two are leaning on each other, right? What if there were more self-sufficient but interdependent people that you're starting to lean on, right? So you're not like, Hey, I don't depend on you for, we don't depend on you, but we do, there's an interdependence, right? There's a sharing the load, carrying more together, the whole is greater than the sum of the parts kind of components that, that are almost waiting for you to request. Hmm. Yeah. Hmm. Yeah. What I'm, I mean, Mark and I will, we'll talk about this more, but like, I'll just share it. Um, like the, there's like this thing that's just been like staring at us, which is like spending money on ads. I'm just getting that as an example. And like, for some reason, like, I just feel like I'm Mark, I'm trying to slot that in my head. I'm like, is that buying a lottery ticket? Is that, you know, like, and I know intellectually, I know intellectually that, that it's not buying a lottery ticket. I know that when you run ads, you learn things and you, you know, and it's like a commitment to like a path. And I, but then in my head, like the story I tell myself is like, I'd rather pay someone to do that. You know, like there's, there's like a part of me that just doesn't get excited about that. And so that's an example of like, I do wonder if there's like these limiting beliefs that I, each of us probably brings, but like, that's maybe an example of one that I bring, which is like, I'm literally part of the, like, am I part of the problem is like, is it possible that if we take whatever percent of our revenue every month and put it towards ads and just help us get in front of people, like that will all be good learnings, even if we don't get any sales from it and that we just haven't been doing it. Cause I'm like, I care more about what keeping the cash. Like that feels stupid at the end of this conversation. Like, as I'm thinking about that. Well, I was thinking of it as almost like an experimentation budget. Like you all are like, we're playing poker. We don't know what hands, but also maybe there's a different table we could be playing on. Or, you know, like there's, there's just like, we're, we know this table really well. But if we allocate even, and you can control the allocation, right? Like what's our allocation to experiments, to learnings, to like. Almost feeling like it's a zero or it's an, you know, it's like an education expense almost. Yeah. Or just the price to pay for knowing, knowing, right. Like, like almost like that's the stupidity tax of like, Hey, like, you know, you're, but like another example that comes to mind is like, okay, like, like a lesson, a lesson that we got lucky that we got learned early that was really valuable is like the power of giving a lot of really good stuff for free. Right. Like, I think it's one of those other things that you like hear everyone say like, Oh, of course, marketing 101, right? Like give your Legos up for free and, and then people will still want to buy your stuff. Right. Like I, and I think we got lucky in the sense that like we both, it worked really well for both of us. And, but yeah, but it was also like one of those things that like, it's just like, again, it was more of like a trade of like our time per, which I think for us it's just harder for some reason, like we're okay training our time, but I think it's way harder to trade our money. And I think there's, there's something interesting there. I'm not sure what it is, but, but it's in general. Yeah. It seems like a one-way door, right? Cause you, especially you Mark, you talk about money and time almost interchangeably. I think Ben a little bit, it's money and space a little bit more, you know, apartment, uh, space or office space, or even travel is more space oriented, but yeah, yours especially seems to be very time, but yeah, you're saying maybe it's, I want money to give me time, but am I willing to spend money? Which, which I kind of, it's interesting because I, I think of Mark and Mark, don't take this the wrong way, but given that you don't have kids, um, or a dog or you're, you know, not married, like I, I think of you as someone who's more time rich than me in the sense of like having more hours to like play with. And, but, but it is interesting to me that may, that if what Jeff just said is true, that you, you think of the value of your time, potentially even more than I think of the value of my time. And I wonder if it's because I'm already like, there's literally only like, I don't have any time to play with. It's like, it feels very limited to me. Hmm. I'm curious if that, if you have a reaction to that. Yeah, I mean, I think to me it's more of like the cost, like the cost of not knowing now is really expensive, right? Because like, if we figure some of these things, something out right now, tomorrow, then we can compound on that learning for way longer, right? It's like, why, it's almost like, you know, the best time to plant a tree. Yeah, it's less about your time. It's more about an, an urgency vector that's like the longer we wait to find out, the less compounding it can have. Exactly. And, and the more time, time in market, right? Like the faster you find out, the more time in market. Okay. That's, that's helpful that I understand you much better now. Yeah. Yeah. Do, I know we're, we're landing the plane here. Do you, do you want to fire off any things that feel important for like codifying in your, the constitution between the two of you? And that could just be like nuggets of insight or takeaways that you want to be like, ah, remember this. Hoffman process. Remember that? No, remember. Yeah, I actually, I actually think one thing I would love for us to talk about as a follow-up, Mark, is. Um. follow up mark is, you know, given that we do like almost, you know, like monthly distributions to each other, I am almost kind of curious to know what number each of us would need to get to feel like it's enough for that month. And then the reason that would be a good data point for me is because if we establish that we want to have like a fuck around and find out budget kind of like to test things, I feel like that budget should never dip into like the thing we need to feel kind of like we're getting enough or like we feel safe financially. And maybe part of my fear has been that like in order to do that spending, we would be dipping a little bit into like the don't fuck with this amount of money kind of thing. Yeah, that's super tangible. I love that. And I think for me, one thing that I would love follow up to is like the maybe coming up with like a protocol of like what happens when like, if we have like a bad month or two months, like how do we how do we navigate that together in a way that feels safe, that doesn't put us in like in a scarcity mindset and that like, allows us to like continue to trust the process and to stay in the market and protect this thing that I that that we've built, right? And that this thing being the relationship, the business, our expertise. And so I think that's one thing that I would be excited to just like, go deep. I'm imagining you writing a hard time manifesto. It's like, hey, break the glass. It's time to read the thing like, I know, we knew this time would come. You know, like this is how you're inclined to react. But this is, you know, this is a message from your higher self or yourself in abundance mode. And, you know, providing those steps in case of emergencies seem like they could be really potent to have at hand. And one of you has to remember to be like, wait, we've prepared for this and bring up the document. Yeah, we can train the AI agents to be ready when they get some hints. And I would say like also as part of that, figuring out what is that threshold? Like what? Because like if we have a month that's down 10% or something right now, I'd say we don't break the glass. But like, there's some amount that we'd both we'd be like, this is the time. And that's it's also good to know what we would both consider that. Yeah. And I would use whichever is the lesser of the two, right? Like if one of you is down 10%, one of you down 20, like just honor the lower or the lesser. The 10%. Yeah. Yeah. Yeah. Amazing. Well, I know, Mark, anything else? I think we have three minutes left. Yeah. And no, I think that that was a big one. And I think the other is just like really quick one is like, I think let's keep appreciating each other. Let's not wait to have, you know, our friend Jeff here to force us to do what we like about each other. Like I think let's make it more of like a practice. And, you know, I'm personally like bad at like timely feedback. So like maybe like just like we can like schedule it, which sounds bad, but also like maybe that's okay. And you got to do whatever works for you. But yeah, I mean, that felt really good. And I know it felt good for you too. So I think we should do more of that. And, you know, I think while this was cool to do remotely, I almost imagine like what, like how much cooler would have been if we were in person or like, you know, like we're having dinner or like we're in a mountain, like with no internet, like, so like, just like a reminder for me to like maybe just do this in person. Next, we've got the studio. We've got the studio ready when in the city, Jeff, if next time Mark's in town, you're free and our schedules align, we'd love to do the next version of this in person. That would be amazing. I was wondering if you two budgeted money to do retreats together. It's funny you ask that. We just, we're planning our, I'm guessing January, December, January trip. I'm not sure exactly when. I think we're not going to catch each other before the end of the year, most likely, unless you sneak in a New York trip in like November or something. But like, yeah, I think January and then yes, we're definitely talking about that. And that's actually one of the things we want to spend some money on. It seemed like a place where you both are longing for it, but you might not spend the money on it. And so it fits in that kind of gap that we're talking about. I think you sniffed it out perfectly. Okay. So with that said, Jeff, I just want to say a huge thank you before we do our closing rapid questions, but thank you so much. This was everything I was hoping for and more. And I'm just very grateful to have you in my life now and wish I met you earlier, but hey, better later than, than, than ever. More time in market. I know, I know. Exactly. So a couple of quick questions for you is, you know, if the audience is listening to this, wants to follow you, learn more about what you're thinking about, where, where can they go and, and find out, and then how can they potentially be helpful to you as well? Okay. Easiest is LinkedIn. I'm most vocal on LinkedIn, a mix of effort posting and shit posting. So reach out to me there. I have a website, jeffgreenberg.co. In terms of having to be helpful, I like to be helpful to people. So if people are interested in coaching, that's founder coaching, exec coaching, personal life transition, coaching, and some therapy. I do that. I run a men's therapy group. I host men's retreats. And if people don't know, but think I have something to offer, I also do workshops. That's financial therapy in nature. I do it with individuals. I've got one coming up that is with couples that's for private community, but thinking about how that might fit into an organization or where there's maybe like stickiness around money within an org is a thing that I'm really excited about to create those spaces that people, when I hope those workshops are like, wow, I've never had a space to talk candidly about money. And just that lack of aloneness or more like, Oh, you with a lot of money, you're going through similar things that me who's not had as much money. And that feeling of like, Oh, we're all figuring this out. We're in a culture that almost doesn't want us to figure it all out. And so it can be subversive and radical to create those spaces. And so I love any opportunity to do that. Fantastic. Mark, you want to ask? Yeah. One final question, our gratitude corner. And so Jeff, you've had, man, a fascinating journey through life. And I'm sure it's only, it's only the beginning. And you've, yeah, you've, I feel like you're like kind of found your, your zone of genius. And I feel like, yeah, it's a beautiful expression of who you are. And so I just wanted to take this moment to maybe like thank maybe a few people that have played a key role in that journey and where you are today. A lot of, you know, when I was an economist on wall street and a lot of people, when I started talking about my transition, we're kind of like, I don't know if that makes sense. What are you going to do? You know, they kind of projected their own anxieties, some of them financial onto me. And then other people were like, no, that that's the right way. And so my partner and my wife has been very just like, yeah, go at like, that's what you need to do. A lot of my friends in Brooklyn have like see me far more as a death doula and other things than they do ever as like a wall street economist. A friend and mentor, Seth, who started the men's group I'm in also went from wall street now as a psychiatrist. And he was, he's been an incredible mentor and he started this six person intergenerational men's group that meets every week, every Wednesday. And that's been just like deep in my heart to just see men living in ways that are role models to me has been transformative. And just to have that in my life at the middle of every week and have him take the leap to put that group of men together. So those are three big ones that stand out for me. Beautiful. I love it. Well, we appreciate you. We'll do this again soon, hopefully in person. Otherwise I'll see you in the neighborhood over coffee, Jeff and Mark, I really appreciate you doing this too. Yeah, it was awesome. What an honor. Thank you. Yeah. Such a privilege to do this. I agree. I agree. Okay. That's a wrap.