Conversation No. 024 w/ Ryan Shank | From Validation to Vision...

Mycore is on a mission to be the world's most people-centric company. The purpose of this podcast is to get to the core of people. I'm your host, Nathan Bourne, and I invite you to join me as we deep dive into the personal and professional lives of our guests. We're going to learn who they are, why they exist, and what they do. We're going to hear their stories, the good, the bad, and the ugly. In other words, we're going to talk to some really cool people. Welcome to the Mycore Podcast. Coming to you live from New York. It is Tuesday. I am pumped to be here with the one and only Ryan Shank. Welcome to the Mycore Podcast. This is Conversation 024. I'm obviously outside of my usual studio because I came up to NYC for both New York Tech Week, but also to hang out with my boy Ryan Shank from Sharewillow. And today we're going to be talking to him about his wild journey as a founder, as a leader, and talk about how we go back many years. We've known each other a while.

Yes, sir.

Do you remember when we first met?

Freshman year of high school.

Gym or football?

Football practice.

So you remember we sat on the bus together? Yeah. Made fun of that dude. No, he's cool. We didn't make fun of him. Yeah. But like, we were making fun of him, but not to him. Anyway, we're like good people.

Chill.

Um, I think that was probably when we realized that we were silly and, um, like to have fun. And then we've been friends since. So today we're gonna get into some good stuff cuz, um, Ryan has an awesome story, a lot of highlights, but there's some lowlights. And I, I think it's important for people to hear and feel that entire journey. So I said this in preparation, um, your life is a movie, dude. Do you know that?

I would disagree, but why? I feel like right now I am, uh, I just work. Like, I'm pretty just on the grind. I'm pretty locked in.

Yeah, I don't know what—

I don't know what— I don't know what movie you're referring to.

Well, okay, maybe for those that live in New York in like West Village and are building tech companies is like a day in the life. But there's like a bunch of people that live outside of New York. I don't know if you know that. Like a lot of them. And they do not live like this, which is, I think, important because if people see the way you live now, the way that you are now, both like your capabilities, your lifestyle, you're off the chart, right? You're an outlier. And to be an outlier, you can't just be like a normal chill dude. Something traumatic had to have happened. I mean, like, have you ever met like a normal chill dude that's like doing the things that you're doing in the world?

It's funny, I, uh, if you look at like Elon, like tons of trauma. I think a lot of, uh, I think a lot of people who are chasing chasing something have a lot of trauma.

Yeah, and it's almost like something's chasing them and they're chasing, you know, it's like, it's— are you chasing it or are you running from it?

Yeah.

Um, it's like rhetorical, but you could answer it.

I don't know. So, so, uh, one of my therapists back in the day was saying, you know, it's like a lot of times you are super, super heads down. You're like, all right, I'm gonna like create validation through work, you know? So like, that's kind of what you're chasing. Um, and I actually have a lot of friends who are founders who were kind of on that journey in the beginning and then have since like done a lot of self-work and sort of realized what was happening and then have like now lived these like more fulfilled lives. But I think especially in the beginning, in the younger days, um, that is a thing. Like, if you don't have a lot of, like, self-worth, or if you have, like, low self-worth— like, a lot of people are chasing that self-worth through validation and through, like, success with, like, business and work and stuff like that.

Would you say that's true for you?

It definitely was.

Tell me about that. So why, in your background, in your story, would you say there is not validation?

I think, um, well, I think, I think most wasn't— yeah, yeah. I mean, I just think a lot of the, a lot of trauma stuff, a lot of like self-worth stuff, I think comes from like childhood, comes from, you know, parent-child relationship, whatever it is. So I think a lot of that stuff sort of forms at like a younger age, and then you are like, all right, like I'm gonna go out and I'm gonna get this sort of validation, I'm gonna get this, uh, self-worth through success, through money, through whatever it is. And I think, um, yeah, I think that definitely was the case with me.

And, um, I was gonna ask you, do you feel comfortable sharing some of the specifics of that? Yeah, I mean, I think, uh, because I, I, we've known each other a while, I know some things. So like you mentioned the parent-child relationship, so mom, dad, like, tell me about that.

Yeah, I think, um, I think, uh, I don't know, I'm not your therapist, but I mean, I think, look, at the end of the day, I think, um, if just generally, like, if you don't feel like you're, like, wanted and, like, loved and you didn't, like, receive that love— and by the way, it's not, like, a parent's fault or anything because they're also parenting for the first time they might be going through their own stuff, that parents are parenting for the first time.

Well, that is like fact. But do you believe that's not their— like, you actually believe that's not their fault?

100%. 100%.

I don't.

I think I have like a lot less sympathy for my parents.

My premise is like, get your fucking shit together, because every level has its devil. And like, you didn't know how to start a company before you started one. I didn't know how to be a parent, and I definitely was not good at it right away. I'm certainly still learning. Yeah, but like, at some point, if we're being real, both of our parents are pretty fucking selfish. Maybe not your dad. Your dad's held it down. Yeah, yeah, my dad is selfish as shit.

I fucking love my dad.

Yeah, he does, man. Dude, I fucking love that dude. Um, miss him. How's he doing? How's Gary?

He's good, good. He's good, he's good.

But your mom struggled, dude.

Yeah, and look, I don't want to go super, super deep into it, but I think also knowing now what I know later, I think like she also is struggling with her own stuff, and that gives me like tremendous amount of empathy. Like one of my life coaches, actually, he like doesn't have a good relationship with his dad, but he's actually super grateful, right? And that's why I would say I'm almost super grateful for that relationship, or like lack thereof, or you know, whatever it is, because that gave me so much like drive, it also like gave me so much— like, I had to like look inward. I think people who are super happy, who are just getting like flooded with, you know, oxytocin through like the love drug from their parents, and they're like getting the emotion from their parents that like they're supposed to get, like, are kind of just chilling. Like, they're just happy. They're like probably in relationships. They probably have kids by my age, like probably grandkids by my age.

At the end of the day, we're not that old.

Um, You know what I mean? But like, but I kind of like that, like, I have this fire and drive. Like, I think it's like done me really, really well. Like, I really like my life right now. Um, I think I had—

you had like your life— like, I had to go through like 48 hours.

Like, I had to go through all of that stuff and like there was like terrible times in there and stuff where it was like really, really hard. But like, I, I actually am really proud of a lot of the stuff that I've like built and accomplished. And I think like I wouldn't have that level of pride in my work if I wasn't so dialed in, so locked in, so driven. And I think like to even get that level of drive, like the thing is like the stuff that we're doing, building companies like it at some— for some years it sucks. Like it's not fun. It's actually irrational. If you think about like the risk reward profile of it, it's like, dude, you're going to like try to do this when like all odds are against you. It makes no rational sense to like financially, you know, give up like a comfortable salary for, for no salary. Like it's actually quite irrational. But the thing is, like when you do it and you pull it off, like you have so much pride, like you're so prideful. So it's like when I am posting about stuff or I'm like, look, look at what I've built, it's like, dude, I did that from nothing. So you— and not me, because there's a team and, you know, all of that.

But it's like you had to dream it up and you had to set it in.

And I don't think I would have gotten that if I had proper, uh, parent-child emotional stability.

So let's, let's set the stage for this though, because, you know, I, I mention my story and people— it's like, if you know, you know. You and I have this in common. So, um, I'm the fourth of nine children, different but similar, and I think this was our bond that even from day one, we kind of recognized that, like, well, you're a different creature. And we would have been 14, so I don't think we probably had— well, we definitely didn't have a lot of perspective on it because we were, like, in it, like, in the middle of it. So I think that was part of our connection, you know, to, to think, like, yo, I think you're built different, you know, than, than the, the person, the people around us. Um, so a lot of trauma in both of our background. Um, I would say, again, not a psychiatrist, but like major abandonment issues, major, um, lack of nurturing. And I think something you and I share is that we just had to grow up like really early, like make money, uh, fend for ourselves, kind of learn even to like self- soothe, self-soothe, like, so emotionally and physically, like, had to take care of ourselves. And I think that built a resilience in us. It probably built, like, dreamer, you know, and wanting to, to, like you shared, have things that we can be like, I did that, you know.

And yeah.

You might not be proud of me, or you might not even understand it because it's like out of the scope of your understanding if you're in survival to build something that's worth millions of dollars, or that people think is tens of millions of dollars, right? Geez, tens of billions. But, but really, like, the, the delta between where you came from and where you are is off the chart. It's not even like, you're doing good for yourself, son, like all things considered. It's like, now I'm doing good for you. Like, I'm doing good for a guy that came from where you came from, bruh. So you're doing these off-the-chart things, um, and, and kind of the, the parallel I want to draw here, just like the reality, is that you can't have one without the other. Like, people want to be you you in the sense that they want to be as quick-witted and as capable to inspire and influence and, and like just make shit happen, you know, like bend the universe. But it's like, bro, you didn't have the trauma that I had. You didn't have to survive the way that I had to survive. You didn't have to navigate the world the way that I had to navigate the world. And I think it's important for people to recognize that, not just because we love the arc of the story but because it's like, don't break the 11th commandment, thou shalt not kid thyself. Like, you're not gonna do it, dude. Like, find a guy that's fucked up like a Ryan Shank, like a Nathan Bourne, and nurture that person. And that's like, that's kind of weird. It's like, no, come alongside and take your stability and like mix it with our nutty ways. And that's where I think the magic can happen. So I've surrounded myself with really stable people typically that are older too, that can like love on me because I just need that, you know. I need that like nurturing. And it's not like in a weird way. So I'm curious, like, do you ever feel hidden in plain sight where like you are doing it and you're all up in it and you're like vocal and public but at times just feel lonely?

Um, so it's interesting, I kind of view myself as like pre-therapy and post-therapy. So I started going to therapy basically the end of 2020, beginning of '21. So call it— call it '21 is kind of like this like point in time where like I look at like pre-therapy Ryan and he's so different than like post-therapy Ryan. Um, pre-therapy Ryan, like I didn't let people in, I wasn't like vulnerable, I was almost like afraid to show people like my real self, like they're not gonna like love me or want me or something like that. And I think like because of that, I kept people at a distance. So that, in that scenario, like pre-therapy Ryan was like very lone, like lonely, like on the inside, right? You know what I mean? It's like I would have all these people sort of like right on the edge but not really let them in, right? Um, and that creates a lot of loneliness, a lack of connection. Like there's tons of downsides there.

Yeah.

Post-therapy, when you start to like really have confidence and understand who you are, um, I'm letting people in now and I don't feel that level of loneliness. I feel like I can let people in. I feel like right now I feel so confident in like who I am, what I'm doing, my true self, my full self, like everything, that I'm like, there's nothing to hide. Like, I, I'm— I feel really, really good. So I feel like pre-therapy Ryan, kind of before I did a lot of the like work for sure, but right now I don't. Now I'm like, I own it, I embrace it, and I like think it's one of my superpowers.

Cool.

And so I'm like, let's fucking go.

Nice. I like the way— yeah, so I'm like, let's fucking go. Yeah, well, let's talk about that a little bit because one of the core values of my core— and I'm writing this book, Lead With Who— it kind of touches on, on what you're speaking to, which is this idea, this premise that like you are who you are, you know, you were born the way you were born. That's nature. You have your nurture, your environment, your childhood, your upbringing. And at some point you choose a path, you choose a journey and a process. And I think a lot of times, particularly when you come from nothing or you're— you have a background that maybe is, is hard to face, you, you can stuff that away. And like, that's what I did, right? Like, my story being that I grew up dirt poor, big family, then worked my butt off to be a Division I wrestler and an Ivy League student. And that's all well and good, and now that story is kind of nice to tell, but at the time I was just denying that I came from where I came from and just acted like I was a prep school kid that was destined for, you know, the Ivy League, when in reality it was because of the trauma that I built the very drive to do the deal. So I try to understand sometimes, like, where my drive comes from. But even the story you told, your narrative, there's a lot of people that have messed up. Like, most people stay there. Like, it's not like 'Oh, you're super successful. Yeah, I came from shit.' It's actually like, 'Oh, you're a loser.' It's like, 'Yeah, I came from losers.' So the rich get richer and the poor get poor. So somewhere along the way, somebody put something in your mind.

I know exactly what it is.

I realized at any point— I realized—

yeah, I was gonna say, I'm not interviewing, we're fucking talking. Yeah, I was gonna say, uh, I actually realized it recently. So like growing up. So firstly, we talked about Jesse Itzler earlier and we talked about how like words are so important. And I think like words and saying positive things, like one of the Jesse's things, like he basically was trying to run a 100-mile race or something and he couldn't get past mile 36. And he hired this Navy SEAL and he basically— the Navy SEAL was essentially like, what you're going to do is you're going to tell yourself, I don't get tired, I don't get tired, I don't get tired. And you're basically just going to say these words. You're not going to— give negative thoughts a voice, like even in your mind. Um, so that, and then just like believing in yourself. And I think like, I, I didn't realize it until later, but the first person to like speak belief into me was Hailey in college. Like she was like, you're like so talented, like you can do it. So I think being around her— so Hailey was my college girlfriend, we're still— we broke up in 2012, we're really, really close right now.

And we do another episode Of what? About that? I'm joking. I know, but you guys have a really cool relationship.

Really, really cool. Yeah. And she was the first person that like spoke belief into me, and then that made me start believing in myself. I didn't come— like, my parents were never like, you can do it, like, you're so talented. It was more of like, you're bad. And then you start to— like, when you feel like you're being perceived in a certain way and you hear those words, you start to believe it. You're like, I'm being bad, I guess. Like, this behavior is kind of bad. Like, maybe I'm bad. Fuck, I guess I'm bad. And then you like believe that shit, you know what I mean? Whereas like, if you're like, dude, you are so talented, like, oh, you're, you know, you do, you're so creative, like you're just so not in that, like you're going to do amazing things. I know you're going to do amazing things.

College to really feel that, to feel belief.

Yeah.

So I want to give some context here because you and I did.

But the thing is, the thing is, I think I was right there. I think I like, you're on the brink. I was on the brink. I was like, I think I can do it. And then I never did it. I think I can, boom. So I would like have all these like starts and then it's like, I don't know, not really sure. So there was a little, there was doubt. Whereas like once I, once I felt belief from someone else, then I started to like truly believe in myself. And that's when I was like, that's when I know I can do it. And that's what I talk about now, how I was like, I'm going to be a billionaire. And like, I know I'm going to do these things because I like just believe it. And I've— and now I've had like the feedback loop has closed and I've like got the value. I'm like, oh shit, I did that. Oh, I've done that. And it's like, dude, this is happening, right? 100%. I start writing it down, all of that stuff. But it's like the self-belief is, is the critical piece. And it didn't come— it wouldn't have come, I don't think, unless I got it externally for the first time, someone speaking belief into me.

Oh wow, there's a lot there. So I think I'd like to like drill down on that because to give context to our listeners, um, Ryan Shank was not always 6'4". You— there was a time—

most people who are 6'4" weren't always 6'4".

That's fact.

Yeah, yeah.

But there was a time where you were like heavyset-ish, chubby, I don't know.

I was like—

just own it.

I was like, um, plump.

Plump.

Yeah, like a plump, like a rounder, like rounder, like soft.

But like you weren't this— like you didn't have the stature that you now have. Like when we met Yeah, you were like as tall as I am now, probably like 5'11", and you were plump, and then you like shot up. So that obviously is gonna lend to your confidence. But you were always the life of the party, right? Like, and maybe some of that partying is where you got your being bad. Like, is, is that where your parents or your mom was like, you're doing bad things because you're having a party and people, right?

Right. Yeah, yeah.

So like, what I think is really fascinating about your story, and that I think can inspire others, is that you had this like stored trauma. It was like on a hard drive somewhere, and I don't think anybody would have known like unless they knew, which you create such a force field of charisma that most people can't— they get so caught up in it that they can't like discern and decipher through it to get to you.

Yeah.

And I'm sure there's times where like, or I wasn't letting them in.

Well, right, right.

I mean, you created it, you create the force field. I would imagine if you, if you took that further into like dating, then it's probably even more of like a—

so, so quick interesting story, uh, so I actually really like Scooter Braun and he did a bunch of work. He talked about it on a podcast. He did a bunch of work. He went to the Hoffman Process Um, and one of the things that you do to protect yourself is you create these like personas. He said— so, so his thing is like he created this persona that's Scooter where it like protects little Scott. Scooter is like this larger-than-life music manager, celebrity, right? Super wealth, all of this. And it's to protect Scott. But then what he realized is Scott was actually so capable that Scott created Scooter. So then Scott is actually capable. So it's like you you are actually capable. And I think like a lot of people, myself included, like will do certain things like that. It's like, I'm gonna protect myself, so I'm gonna like use humor, I'm gonna like kind of like keep everyone on the outside, I'm gonna like not really like let them in. But like at the end of the day, like you are capable of creating that persona to protect you, so you should be confident in your actual person.

I like that, that's good, man. Yeah, and one of the things I'm trying to kind of unearth in this conversation, like in this moment of the conversation, is this fact that when you're doing big things, people that aren't doing big things, they convince themselves that there's something special about the— those people, right? There must be something special about Ryan. Now, there is something special about Ryan, and we could sit here for hours and hours and hours and dissect every bit of it, but at some point you took the bad and the ugly and the good. The good, the bad, and the ugly. And you concocted it, created an elixir that has been a fuel source and a resource for you to keep going. I mean, you made money at a pretty early age in your journey, right? I saw it. The first million-dollar wire transfer you got was 2016. 14. That's what I said.

Yeah, yeah, 2014.

Yeah, yeah, 14, right? So you're what, I think it was you're 26 at the time?

I was 26.

Okay, so you're 26 years old. Yeah, right. Like you're getting off of your parents' health insurance.

I was never on my parents' health insurance.

I know, but that's what—

that's like what normal people—

exactly.

Yeah, like normal people who like still have a childhood home are on their parents' health. Can you imagine that? That's crazy.

Like a—

like a home, like to have like a Thanksgiving to go back to. That'd be wild.

I mean, everyone like, like their own room. Oh my God. So yes, like according to Obamacare, the average 26-year-old's like, I gotta get off my insurance and you're right, getting mills. Like, but the thing is, most people, if they knew what you had to go through for those 26 years, they wouldn't, they wouldn't take that trade. You know, they were kind of like, nah, like keep them.

They don't take the trade. That's the thing. No one takes the trade. No, like I have so many, I've written about this so many times. It's like, to join M Help Desk, like, I quit my job with $50,000-$60,000 in student loan debt. I rented out my bedroom. I took no salary. Like, no one would do that. Like, everyone's like, like, when it comes— push comes— even now I'm hiring people and I kind of give them like cash versus like equity, and like most people just take the cash.

It's like no one's really down to actually like give it up, delay the gratification.

Yeah, I mean, look, at the end of the day, they're probably more rational. Like, the risk-reward profile is pretty misaligned. Line. Like, you do have to take on a substantial amount of risk in order to get the upside, but like, they're just not willing to do it. And by the way, tons of people make money without doing this crazy stuff, uh, right? But just in general, um, 100%, like, you have to take the risk, and a lot of people aren't willing to take the risk, which is fine, right? Right.

Yeah. So I, I don't know, like, I've not met a person that's building anything interesting that is not an interesting person. And I've never met an interesting person that doesn't have some kind of wild origin story, whether it's fourth of nine children growing up poor, you know, single, uh, mom that can't put it together. The thing that's really fascinating to me about your journey too is your brother, because Brett took like a very straight and narrow path in the sense of like has his shit together. It's like a pilot now.

Uh, he has his pilot license.

Yeah. Okay. But that's not what he does full-time, right?

Right. No.

So he's like also a pilot, right? So you guys have this brotherly bond, but you couldn't be like any different, you know, in like, as far as like personalities and, and life paths. And I'm always like amazed by people that grow up to the same, in the same house, to the same parents and like relatively the same circumstances. Why are you like you and Brett's like Brett? Why not flipped?

So I've actually thought about this a lot. So firstly, my brother's awesome family, 3 kids, stable job, amazing wife, um, cool hobbies, like does motorcycles and planes and like just cool, like some, like lives in a house, you know, and like a neighborhood, like very like normal and awesome. Um, so I was thinking, so firstly, I'm not 100% sure this is accurate, but one of my therapists got— had me read this book, um, Children of—

by the way, you have like a team of therapists or is this like a sequence?

Whole team, whole team.

Like a board of therapists?

Yeah, yeah, yeah.

You can say like one of them.

They're like, my therapist spend— my therapist monthly spend is like pretty outrageous. Um, So it takes a village.

Yeah, yeah.

So it's like, I got my therapist for this, you know, specialized. Um, but basically she had me read this book, like, Children of Mothers with Borderline. And like, my mom hasn't even been diagnosed with borderline. We're just diagnosing her like over here. So I don't even know that that's real.

Like, I could diagnose it.

Um, but a lot of times what happened— so, so my— one of my speculations is if you're the first kid, you get all the attention and all the love. You feel the love, right? If you're the second kid, your mom— especially I was only a year after, so like— and by the way, this is like unintentional, and like I'm going to be pretty thoughtful about this like when I become a parent, but it's like, okay, so you have no kids, you have your first kid, you can give that kid all the attention, all the love. The kid, by the way, just from feeling the parent's happiness, it has these signals, right? If you're the second kid and now you have a 1-year-old over here, you're stressed, you're like, holy shit, I got this second kid. Second kid, again, unintentionally could feel like you don't love them as much if they're distracted or if you're like upset and stressed when you're taking care of that kid. Like at age zero, you know what I mean? Not even— it's subconscious, but like the kid might be like, oh my God, anytime my mom touches me, she's upset. I'm making her upset. I'm not wanted as a child. So I think like that could happen. So like on the surface, all you guys were raised by the same people. But yeah, but like if you got different signals, I— again, I don't even know that this happened.

This is just some thought that, you know, like, every day I try to figure out what the fuck.

Yeah, yeah, this is like a thought that I've thought through. Um, so like, you could totally like feel a certain way as a kid and have these like trauma that like unintentionally got like sort of zapped into you, and it's like stored.

It like lives there, right?

Yeah, because you're like, this is— I guess I'm unloved, I'm unlovable, because like anytime my mom like touches me, she's all stressed. But she's only stressed because she has this 1-year-old over here who she's also trying to like take care of and stuff like that.

Right.

So I, I, I could see a world where two kids that you think they grow up similarly, but like as children they were getting like different messages like from the mom to the baby.

Now this is super touchy, man, so I, I just, again, I appreciate you going there. Um, did your mom treat Brett differently like throughout most of your childhood, not just the early stages? Because I feel like she was a little bit hard on you?

Um, I think, I think we're relatively similarly treated, um, through, throughout it. But the thing is also, if you think about it, if you, if you're a parent and you have one kid that's like super like obeying— what's the word? Obey?

Yeah, like obedient.

Obedient. Yeah, yeah, I knew there was a word.

He's like compliant.

He's like, yeah, if there's one kid that's like compliant and then another kid that's like not compliant, it's also like throws you off as a parent. You're like, whoa, I'm not used to that. I don't really know how to act. And then if you as a parent, if your parent didn't like give you the playbook, if you don't have the resources to understand, like, I think like now as like a leader and like founder and stuff, I understand like different people have to sort of like get managed and treated different ways. But like if you didn't come from like that kind of background, tools like, yeah, it's like you don't know how to almost like manage your kids in that sort of way. So you're thrown off. So I think a lot of times, like if you're, if you're getting different inputs from different kids, you might like not know what to do, you know? So I think like—

so here's a pretty crazy thing, I think. Your mom kicked you out for like not that crazy of a thing, right? I mean, like, you weren't like doing heroin, dude. You were like going to like high school parties, right? So it's like, that is gonna fuck you up. Like, my parents never kicked me out. They just didn't have a place. So I like went and lived with Mike Darty for like 6 months and crashed at your place and just kind of was transient. But like, did she like say, get out of my house?

Again, I don't love talking about it because I'm sure this is awful.

Let me tell you that. And again, by the way, we don't even have to publish this. It's more important to me that I'm talking to you, Mike. Get emotional— my friend, because I love you, man, and I'm impressed by you, and I've— I fucking know you. Like, they may— they know the West Village version of you. I know the fucking Cameo Court version of you. And the thing is, a lot of our peers, they might think you're like enamoring, and you are, because your, your life's a movie. But they don't fucking know— like, they don't know what you paid, like the cost that you paid. And like we said earlier, they wouldn't take one day of that shit because they get to go home on Thanksgiving, you know, for like a normal loving experience. So the, the whole point of today from my point of view is to honestly honor you for the shit that you've done and continue to do. Like I mentioned the thing, the money thing earlier, because you could just have played the money game, right? Like if you said it was like about the money because you didn't come from money, well, you made money and then money makes money, right? So you've been investing and you're, you know, sort of like quasi VC. But the fact that you're going back into the throes of being a founder and building a tech company from scratch and navigating all the things, that's like once again a different human being. Like that's a different creature. And obviously there's a part of you that loves the grind of it.

Mm-hmm.

But I just want people to understand this profile because I don't think people talk about this enough. I think they just put the name in lights.

Yeah.

And they give like some of the like arc, but yeah, so like you don't have to talk about it, but I just know some shit about some shit that I think people should know, and it'd be weird if you told them first party, so I'll fucking tell them or get you to tell them live in this podcast studio. So like your mom kicked you out in high school? It's fucked up.

Yeah, it's not— most moms don't do that, I would say.

Yeah, right. So you were like— but the thing is, here's the thing, like, but you weren't like doing anything crazy, right?

I, I think a lot of times, like, correct. And I went and lived with my dad, and my dad, you know, moved an hour away so that I could, you know, still attend the same high school. Because I think that was one of the things that like really started to— like, essentially what happened with that is that I realized like someone could take something away from me. And it wasn't like oh, you're kicking me out of the house. It was like, I'm gonna have to move high schools, I'm gonna have to lose all my friends. So I was like, you're able to then take away my friends, my sports, like everything that I've grown up with. I'm gonna have to live like in this random like lower Delaware town? Like, are you kidding me? See, for— see, for Delaware, like that's crazy. Uh, people— zero people on this podcast know Seaford, Delaware. Like, that's crazy. Um, So I think that, like, firstly, just in general, the idea that, like, the person that is supposed to, like, not do that will, like, kick you to the curb, kind of could whatever, like, arguably, like, fuck you up, right? Um, and then it was like, they can take away everything from you. Like, one person has the power to, like, take away, like, the thing that you care about the most, your friends, all of this stuff, right? So I think with that, then it's like, I don't want anyone. So this is the other thing that I've worked through post that is like, all right, I went on this thing where it's like, I don't need anyone for anything. Like, I'm gonna fucking do it on my own. Fuck all of you guys, you know what I mean? And then so much—

like, every bit that we share is like this pile of Ryan, and then there's like more and more. And I think the fact that you're sorting it out now as you're maturing as a man Yeah, yeah, it's just, it's just fucking beast mode because this is like a concoction for like a fucked up person, but you're finding ways to like tap into this part of self-reliance but then go like, well shit, I can't just like not trust anyone and not be interdependent with anyone. But it sounds like this was a moment in life where you said you're not gonna take my life from me because that's friends, sports, girls like everything that was Stephen Decatur High School class of 2006 was up, and it got like hardwired into you in that moment. But then that probably stuck with you for a while and didn't entirely serve you in some ways, is what I'm hearing you say.

Yeah, yeah, of course. But just to go back to it, so like then I went on this thing where it's like, all right, I don't need anyone, I can't be dependent on anyone because like I have to do it on my own because like people can leave me, people can like take everything away from me, so I, I can't give people leverage like that. And I find myself even now thinking of ways that, like, people have leverage over me, and then I try to, like, de-risk that. Yeah.

Um, but I just think that's funny. What a funny way to think.

Yeah. So it's like, well, it's like, you know, like my last company PhoneWagon, Twilio, we were like completely built on Twilio. It's like if Twilio had gone down, I was like, our whole company has gone down. So I was like, all right, we need to, like, de-risk that. And we built, like, our own, you know, SIP stack, our own telephony basically. So, like, we weren't reliant on, like, one party. But that's like a business example.

But I love the connection there because it's, it's like these things don't just happen. Like, we, we normalize them in our life. Like, whatever day that was that you woke up and were like, guys, we're not putting all our eggs— I mean, heck, even in this moment right now, I had a similar experience in, in my court where I did that, was like, dude, all of our eggs are in Gusto's basket. Like, but I'm realizing even right now, I'm like, oh yeah, that's because I've been in situations where I'm like That went to hell in a handbag. Like, I want to change that. So you're saying that some of those early stage, like adolescent at this point, because you're not a child, it's not like baby, you're like teenager, later that almost surfaced in this like very meaningful business case, which is, yeah, sure, like to de-risk and don't have all your eggs in that basket. But again, that wasn't just like an idea of the day that had to come from somewhere. And I'm drawing that connection there. So that, that's pretty cool.

Yeah. Yeah. And even people, right? Like if you're too dependent on, you know, like a CTO or something like that and you're like, all right, if this person walks, I, what am I going to do with the code base? And, you know, I can't do this deal without the CTO. And then if they don't want to go along with it, like I'm screwed there.

So let me ask you a question on this note. How do you balance, cause I struggle with this. How do you balance that? And the too much of that, which could be perceived as— and maybe even if you're being real, like, times where you're opportunistic. Have you ever felt tension between those thoughts where you're like— I'll just speak for myself for a second, like, because I think I default to not trusting. I will think sometimes that, well, while this person is here in my life, in my business, I guess I'll squeeze as much juice out of it as I can. Like, not in like a take from them, but just like in exchange. But I'm kind of always waiting for them to leave me, and I'm like kind of teeing up like their departure. I don't know if you can relate to this, but like, I'm like, yeah, we're killing it, it's gonna be like forever, dude, we're gonna do this forever. I mean, I'm like, I'm like, I have the bench is deep, dude. Like at any point that you dip, like I got 3 people that will replace your ass before the door hits you. So it's kind of a weird thing in leadership because you have to be like locked in and be like, we're going to the promised land together. But if they dip for whatever reason, hard times, life calls them, they fall in love and they move on.

Yeah.

You have to be ready to immediately put in their second string or draft from another team. So I think How do you balance that?

So I think with, like, psychologically, with my last company PhoneWagon, which again is pre-therapy Ryan, I was super worried about that. Anytime someone would ping me on Slack like, yo, can we chat? I'd be like, dude, they're definitely— dude, I deal with that shit all the time. Yeah, can we talk? Like, talk about what? Don't say that. Be like, I love you.

Yeah, I'm here, we're good.

Yeah, also forever.

Talk about this thing in business, right? Right.

So, so I used to be like that, and again, I feel like I kept everyone at a distance, didn't bring them in, didn't do a lot of team stuff. This time around, like I'm way, way, way better. I'm not as paranoid that people are gonna leave. We just did a trip to Costa Rica as a team. I would have never done that at my old company. We do a lot of like team, we do team sauna sessions at Othership, which is a great sauna and cold plunge spot in New York City. They just launched their Williamsburg location.

He may or may not be an investor.

So like we'll do team sauna sessions. Like we'll do like, we just did a dinner last night. Like we do a lot of stuff. I never used to do like team stuff like that. We work in the office. Um, like, so I— right now I feel like I have a better relationship. I think like you're paranoid like that when you don't have a great relationship, and you, you almost, you almost are like— like right now, like my team is good, like we're doing great work, like it's interesting, the customers are there, it's a huge opportunity. So like in my head I'm like, that'd be like crazy for them to leave. I think like before, if you're like, ah, this is like maybe not really working that well, like you're, you're kind of like, you know, I wouldn't blame them if they left, you know what I mean? Like, you almost are— well, you're projecting on—

sounds like you've leveled it up too. And like, I know we're talking about some weighty things. To just kind of create like the timeline, so you go from this very challenging childhood with essentially a broken family and a very challenging personality in a mother. You then go to college, and then you transferred, which I think is a cool thing too, because that— I remember freshman year, you at Towson and then going to Clemson, and just like, that was probably when I realized, damn, Ryan can just manifest like whatever, like he just does it, like he just makes it happen, you know, like no matter what. Um, and then you and I start a clothing company together going into our freshman year of college, which was a really juvenile but like awesome experience. I know we look back at that and think like we had no clue what we were doing, but we were obviously pulling from like these natural faculties that we had, these like— it wasn't even like back in childhood, like we were in childhood practically, we're 18 years old and then you sort of entered like a relatively normal path, right? You join a fraternity, you graduate from college, you take this job, and you're like stable. You mentioned it earlier a little bit, but like what made you flip and sort of say, this is not me, like I'm, I'm gonna risk it all and I'm gonna join this company And like, if I have the story right, didn't you like hit up the founder and kind of like create a partnership with him pretty early stage with mHelp?

Yeah, yeah. But here's the thing that I think like gets missed in that. So it's like, oh, you went to Towson. And then I was like, all right, let me lock in, like got straight A's freshman year. And then I was like, I'm transferring out. Like, I want to go to like college, college, because Towson's in Maryland, 2 hours from our hometown. It just was like Not what I wanted. Not what I wanted. Um, went to Clemson, but here's the thing, like, I joined a fraternity which is, you know, kids come from like, uh, decent amount of money. Like, everyone's kind of just having fun. I'm working every semester. No one else is working. Like, there was like one other guy, Monaco, who worked at like Chili's, but I worked at like Olive Garden. I worked at this other restaurant in Seneca. Then I worked at a bar downtown. So like, I never even really did game days. Like, I a few game days, but it's like, so I'm there, but I'm like paying rent, I'm like working, and so I'm like in college, but then I'm kind of watching everyone else have a good time. And I think that also like kind of drives you crazy because I'm like, bro, you guys just get to chill. Like, you guys just get to do like baseball tailgates and football tailgates. Like, I'm working on football games, you know what I mean? So like, that shit also drove me fucking nuts because I was like, this It was fine. Like, I— it was actually fun bartending, like, downtown Clemson, because like then I became the man, right? But here's the Tiger Paw.

But here's like, maybe one way to describe it is like being in it but not of it. So like, you were in it, like you were there, you were a student, you like saw it all, you like had a passport into it. But they're like of it, right? Like they don't even know that someone else has been their benefactor for them to have this experience. And that's a normal thing. Like, I have children, I want them to be able to do that. I want my daughters to go to college and enjoy the experience and not—

yeah, like, my kids are not working through college. No, fuck no.

Like, dude, I had to leave Penn to come home because my parents were fucking homeless, and I moved them into Westo, paid the first month's security. Yeah, put them on my freaking cell phone. I'm 20 years old at that point. So like, I think this is a, a, a thing that you and I have in common that is very rare, which is—

by the way, by the way, I, I don't want it to get lost. Like, a lot of people work, a lot of people come from way worse. So I, I want to just say that. I don't— I'm not like, I had to grind and it came from like the most broken—

helped. But like, when you're hungry later and you're thinking about the kids in Africa, it doesn't change the fact that you want to go get food. So like, I wish the law of relativity helped. It just doesn't. So I'm not like disagreeing with you, but the reality of it is, relative to where you were born, in what part of the country, in what part of the world, in what part of history, it was super fucked up. And then you, you made it great. Like, you, you decide, you willed it into existence. And there's skills that you learn when you're in hospitality. Like, that video that went kind of viral with that date you went on is hilarious. And like she claimed you were flirting with the waitress, which like maybe you were, but I don't think you were because when you grow up in hospitality you have a lot of empathy for the person. It's not like, oh my God, are you like, here's an extra tip, you're working hard. It's more just like, I see you, I'm going to interact with you as a human being. You're not there to fucking serve me at this table because how—

I actually do that with everyone. I actually think that is like such a great trait. So like even, even like in our office, like the cleaning people, like if you just ask the cleaning people like like, you know, like, what's your name, where do you live, like, just talk to them like normal humans. I think like if you just talk to like people that other people aren't talking to, because you're like, like, I just went to this restaurant the other day and, uh, just talking to like the, the coat people, the host people, like, just talking to people, right? I think is, uh, well, you love people.

I think you've always loved I mean, you and I do the things that we would do, like we would sell water on the beach, which was like illegal, but we would every morning go to Walmart, $3.98, get a 24-pack, throw it in the cooler, and we were like, we're not gonna get rich on this, but if we sell these, we can make like $30, $40, stay in shape. We then—

we did that in like an hour too. We actually should have grinded it harder, way harder. We could have made like hundreds of dollars.

That, and it was hand delivered to them.

Yeah, like as you're on your chair. We should have charged $4, bro.

We should— we charged a dollar. It was bad.

Yeah, that was crazy.

No shit. Yeah, we were way off.

And then senior week, cold water as I'm there getting hand delivered for a dollar. Get it? That's 6 bucks, bro.

Do you remember the, um, bracelets that we sold? Yeah, yeah, this is pretty awesome. So in Ocean City, Maryland, the month of June is like senior week, and to ride the bus every day it's like $2, right? And then there was this organization called Play It Safe, which was all these activities to try to get the team, the senior weekers, to not just party and come do like fun things, but they would give them these bracelets to ride the bus for free while they were there for the week. What we did is we got— we had an inside with, uh, Danielle Jackson. We had the inside, an inside, uh, hookup. We got like sheets of them and then we would go—

we controlled the supply chain.

We had the full— and we had no cost.

We were vertically integrated.

We were fully vertically integrated. No freaking cost. And then we would go sell them to the European people that come ride the bus to work in Ocean City for the summer.

And it was to the point, man, we were selling them for like $20, bro.

It was diminishing marginal returns because it was like, there's like 2 days left, they're only good for June. But I can remember, man, vividly going down there and like, they were these like fluorescent yellow bracelets.

Yeah, yeah.

And it would get to the point where we would just be like, we just flash it like we were drug dealers, and they would like meet us in a back alley. We'd like exchange cash for it. It was pretty wild.

That was sick.

That was sick.

That was, that was, that was a really good hustle. Really.

And I don't think anyone else thought to do that. No, you'd have to be borderline criminal in your mind. Yeah, yeah.

I'm sure it was illegal for sure.

So we've done all these like crazy things independent of each other and together. I know we've talked about like the heavy-duty childhood shit. I'm not your therapist. I just want people to know that like living in West Village and taking the heli to the freaking Hamptons, like that came at a cost. And it wasn't privilege, it was work. And not just work like I worked really hard, but I became a person that you will never fucking be because you would have to endure what I've gone through. It's like the classic Batman: The Dark Knight Bane quote where he's like, you merely adopted the darkness. I was born to it, molded by it. I was a— I wasn't— I didn't see the light till I was a man, right? So I, I just mainly wanted to like go there. Yo, now you make money and you've solved this thing.

The thing is, I don't, I don't actually like framing it as like you made money. It's like you've built something that other people find value in that they want. You built the team, you've built the product, you've found product market fit. It's not even actually about the money at all. It's more of you've built something that people want. That's where I get the pride from. So I actually like kind of bothers me when you just talk about the money aspect because the money is only because people are rewarding or paying for something of value.

You, right? And I think that that's such an important distinction because you can get money. Like, there's like a lot of ways to get money. And then even if you did that one time, like you brought value to the market, you built a team, a brand, a culture, you get acquired, you exit, like you have the thing, I think that's a good moment to check in and say, is it about the money? Because if it is, then you probably just start to play the money game. But to go back into the value game, which, yeah, the output is money. That's nice. You know, that's how we the people exchange in, in this country and world. It makes the world go round. But there must be something that keeps driving you because you wake up like ready to go every morning and you have the resources where you could absolutely not do that. Like, nobody has a gun to your head that's like, you better freaking found Sharewillow and go back into a co-working space and get the team in there and take them to Costa Rica, motherfucker. No one's got, to my knowledge, no one's got a death note against you. And this second time around, so just to kind of fill in some blanks there, you go for it. You build this partnership. You have a successful exit. Then you found your own company, PhoneWagon. You build that up. You get acquired. You went through a season there for a few years because when did PhoneWagon get acquired?

2021.

2021, and then Share— so you had like 3 to 4 years of not being in the throes of—

no, '21, I started Share Willow in '23. So like, it was just 2 years, almost 2 years.

What were those 2 years like for you?

So those 2 years—

so again, like therapy, post-therapy, this is post-therapy.

Um, I was trying to figure out what I wanted to do, to be honest. And you know, I had the luxury of time to figure it out, but like in general, like we're not getting younger, we actually don't have the luxury of So like, we are still firing. So I think I was trying to figure out like, what is really, really big? Like, I want to go really, really big. I want to build something big. So I was looking at a bunch of different ideas. Crypto was really hot in 2021, '22, went down that rabbit hole. I like looked at doing a bunch of different ideas. I just never had conviction enough to like fully commit, right? So I was kind of in this like phase where I would like tinker and I would like, hey, do I— I mean, I really wanted to do— I was about to do, uh, put small cell towers on rooftops of like multifamily buildings because like cell towers and now like data centers, especially back then crypto, but now with like AI, like the need for like data and data centers and cell towers is like actually tremendous. And with 5G anyway, I went down this whole rabbit hole where I was like very much about to do that. I was very much about to do a few different ideas. So it basically took me like almost 2 years to be like, Sharewillow's the thing. I'm going to go all in. And there's a few things that happened. I can tell like that story.

Please do, man.

But like, basically, so basically with Sharewillow, I was looking at the idea. I thought profit sharing was interesting. I thought small business were— small businesses were interesting. That's the only thing that I had done for the past 2 years. PhoneWagon sold to small businesses, Mhelpdesk sold to small businesses, and particularly most small businesses in home services and construction. So when I was looking at Sharewillow and it wasn't Sharewillow, it was like, oh, profit sharing is interesting. Basically, like, people aren't, you know, just growth at all costs. People want to have profitable companies now. And also, like, the rates in the market were so high, people were like looking for yields. People were like investing into small businesses back then as well. But really the tipping point was I went to this wedding in 2023 in Italy. I sat next to this guy, Chuck, him and his wife Stacy. Chuck owns the largest independent moving company in the United States called JK Moving and Storage. They do $200 million in top line revenue. He started it from his garage 25 years ago. And I was like asking him all these questions.

This is like the light bulb moment.

This is the light bulb moment. Yeah, yeah, yeah. Because I was like tinkering and I was like looking at this idea and he's there. He's a billionaire. He has 100 kids. He is the man. His wife is awesome. Like everything about— he actually randomly has a house in Ocean City.

That's sick.

Like, what are the odds? Like, no one with money has a house in Italy. I mean, Italy. No one with money has a house in Ocean City.

No.

And he like takes his helicopter there. Like, he is the man.

He's a home in Ocean City.

That's in South Point.

Nice.

Anyway, basically long story short is he does profit sharing. He does profit sharing for his guys. He now distributes about $2 million a year. He poses with them with a big check. He does coffees with Chuck every morning and he's like, this has like our, our whole team is dialed in. And he's like, look, moving couches up and down stairs sucks. He's like, so you have to get these guys. And he's like, we'll take anyone, anyone that wants to work, we'll hire them. He's like, so anyone who says like they can't find a job, he's like, that's bullshit. He's like, we'll hire them. For them.

Yeah.

And to like motivate them and to like get everyone aligned. He does profit sharing. When, you know, the company wins, they win. And I was like, oh my God, if Chuck is doing this— and then there was a few other companies that I looked at that I admired that were also doing this, and I'm like, there's something here. Okay, what's the playbook? Where are people using— what are the tools? There's nothing. There's no carta for profit sharing. There's no standard. There's no benchmark. Should I do 5% of profit? Should I have a threshold like, all right, I need to do 20 moves per person per month in order to even get the payout? Should I do the payout based on tenure or my role? Like, there's none of that. There's no platform that helps you do it or anything. And I was like, this feels like it should exist in the world. And then I like started talking to some people and everyone was like, dude, yes, this should exist. And that's where I got like just so much conviction. I was like, this is an SMB. This is like a huge market. I know home services, like I'm ready to get back in the game. So that's when I was like, all right, I'm going all in.

Dude, good stuff. I, I love when you're sharing that story. It made me think about the empathy that you have for the rank and file. Like, most people that would need the acumen, that would have to have the thought energy to be a founder, to build an enterprise, to go get venture capital, to just do like all the things that you have to do to take an idea idea and make it real. Which, by the way, people grossly underestimate that season, right? Like, when you go idea and you're vibing in Italy, you're like, I'm gonna do this. There's a time lapse between then and when it's real. Not real like you form the entity or even got the safe note, like we have an actual thing now.

Mm-hmm.

If you can do that in under a year, good on you. Like, you You got it. It might take 3 years before you even hit. And I think hindsight being 20/20, you look back and go like, yo, I was selling nothing. Yeah, I literally had like nothing, like a concept within a concept. So one, I'm curious if you have any thoughts on that, like how you mentally and emotionally keep going even when you're— because it's like this, it's like a little crack in the, you know, you're almost like on this journey of like, I gotta just keep walking out, keep walking out. But I think something that's special about you and why you, you seem uniquely suited for this venture is that you have the ability to be an enterprising employer, but also understand the life of that employee. Like, we come from an area where it's the working class, and mainly it was hospitality, but it's that, or like in my family painting, construction, you know.

Yeah, yeah, yeah.

Fixing up the vacation homes for the wealthy, or, you know, not they're that wealthy, but coming from Baltimore and New York, we thought they were wealthy, dude. I thought Mike Doherty was the richest person ever. Live in Ocean Pines, they're like an old jet ski. I think he's the richest people ever. So it's relative. But I think that's really cool because you have a way, like, with real life experience to know how big of a deal it is when the employees of your customer get their first incentive check, right? So they're gonna like— they're, they're living paycheck to paycheck. Then there's a course correction in their behavior, right? Like they go, oh wait, I probably could have buttoned that up a little bit better so I don't have to go back and fix it, or like pull off the blue tape or whatever their, their thing is. And they see like an extra $200 in their paycheck. That's like the moment that Sharewillow exists for, it seems from what I've gathered. I think you have a really unique perspective on that, that uniquely equips you to build this company where I think a lot of people that maybe would understand that moment wouldn't have the faculties to build an enterprise in New York City as a tech founder. So that's, have you drawn that parallel in your head?

100%. I actually think that's why we're gonna win. Um, so recently I've been like really admiring the CEO of, uh, Savannah Bananas. Oh yeah, I think his name is Jesse. That guy's awesome. Um, if you listen to any of his interviews, he is solely focused on the fan experience. He doesn't care about anything else. It's like 30— I know they all sell out and the tickets are more expensive on secondary, but the actual tickets from them is like $30, all food included. Like the players interact with the fans. Everything is about the fan experience. And I think when you are solely focused on the customer or like the customer, like the employee of our customer, right? Like that's when you win. It's like, it's like I don't care about any of the other bullshit. It's like I'm solely focused on how do I make this employee feel motivated to act like an owner? How do I make this employee feel like he loves working there? He loves coming to work because at the end of the day, If that employee feels like that, he's going to give their customer a better experience. So if I'm a customer of— and I'm like, I need to call an HVAC company because my air conditioner is not blowing cold and the employee like doesn't care. They're just an hourly employee. They show up late, they have dragged their dirty feet, they smell like their shirt's ripped and like they take like 5 hours to do a job that should take 2 hours. Like, that's a pretty bad experience from the customer versus like if this guy is like buttoned up, he cares about his employer, he cares about the customer, he does the job faster, he does it better. They don't have to come back. There's no callbacks. Like, if you can win the employee, the customer gets a better experience, which is ultimately just better for the business. So the world—

like, yeah.

And the world— it's like I am solely focused. Yeah. On our customers and on the employee. And it's like, how can we make them, like, have a better experience? And like, yeah, I do have a lot of empathy for them because I feel like I've, like, not been like a home service employee, but definitely been like an hourly employee, an hourly worker. And again, I've been working with these guys through the past, like, you know, 10, 15 years, like through like my last companies. And yeah, I think that's when you win. I think people who are like, you know, I talk to founders all the time, they're building AI this for, you know, home services and they sit in San Francisco or New York and it's like I actually tell our team, I'm like, we need to be out of the office. And also like most of our customers are in like the Southeast, Florida, Texas, like we need to be in the mud. Like we were actually going to get shirts made with like mud on it. Like, dude, we are like in the mud. Because I don't want to be just in an office. I want to understand deeply the minds of our customers.

That's awesome, man. Yeah, so you have this uniquely equipped experience in your life to build this. With mHelpDesk, with PhoneWagon, it felt like either it just happened and that happens, or maybe you set out with an exit in mind. With Sharewillow, is the plan to build it up, sell it off? Is it to create a legacy company? Like, where do you see yourself in the future, you know, 10, 5? Like, what do you want to do with this?

This is a 20-year journey. I, I said that to our employees. I said it to, you know, when I was raising. Um, it's a 20-year journey. Like, I don't want the quick flip. Like, um, I also, again, this might go back to sort of childhood and like I need to prove it to myself, but like I want to take this one all the way. I feel like like the previous ones, you know, were like acquired early after basically like M helped us.

We—

I did for like 2 years before it got acquir— like really a year and a half before it got acquired, stay there an extra 2 years. So I was there for like 4 years. PhoneWagon, 4 years. This, like, I want to take this all the way. I think also like I'm going to— you start to level up too. Like I, I used to say, and I've kind of changed like my words around this, like, oh, I don't like managing people. Like, I want to become like a better manager or like leader of people because like I just want to— I like, like doing. That's why I actually like the early, early stages and then like the later stages kind of— not later, but there's like a weird gap where it sucks. And then now the stage that we're in right now, it's fun because our product's getting good. But like I like actually doing. Um, and so it's kind of such a different skill set when now I need to like go through a manager to then go through the person that's doing— like, I'm not even going directly to the person that's doing right now. Um, so you're starting to develop, and like, you got to do a lot of decks and storytelling and internal stuff, and some, you know, like, you know, what's your weekly priorities, and, you know, like, EOD meetings and one-on-ones. And it's like, dude, some of that to me, like, naturally, I, I— like, you could ask my team, I always want to cancel them. Like, oh, these weekly one-on-ones suck. But then it's right, then everyone's not aligned and all this stuff. So like, I want now to just kind of become like a better, bigger version of myself that I can take this like all the way.

That's great, man. Yeah, it seems like you're in a moment where you're kind of slowing down to speed up. Not necessarily the company, because you're at like hyper speed, but like you, like you're being more present with who is right in front of you and stewarding it versus maybe kind of bulldozing and being like— it kind of what I touched on earlier, it's— it can teeter on opportunistic because you're sort of like, this is going to happen with or without you. And then it kind of creates this dynamic where you can be like, maybe, maybe better without you, in fact, you know. And then there's like this unsaid tension of like, I don't even give a fuck if you're here. That's like super toxic, right? Even, um, if it's true. Even if—

wait, what do you mean?

Meaning like, give a fuck if who's here? Like, I think highly driven people that are what I call high caliber humans, they have an ability to lock in on a goal or a vision or a future state, and their strength is they're like an ant. They, they will go over, under, around, through, like nothing's going to stop them. No setback, not the elements, like not the economy. Well, in that like drive, they can sometimes like plow over people, like literally mow over people.

Yeah.

I don't know if you've done that in the past, but I have. And slowing down to like be a better leader, to be with people and develop them, and, and do it from a place where you're like not even concerned if they're with your company anymore. It's just like, I actually give a shit about Jack and I want him to live a great life. And if it's at Sharewillow, awesome. If he becomes his own founder, cool. If he decides to part ways— so I think that that's a big part of leadership is like, because why I think is that you, you have to get into this trust factor that we've established was not really set up well for either of us. So it's like How do you hold that space and kind of have like faith and trust and belief that that person is going to choose to be part of your vision? Not because you've just like either bulldozed them or created such a great life for them. And sometimes you can get this like God complex where you're like, but look, I've provided this job and I've provided this lifestyle and I've provided this role for you. So, there's just a lot in there. And it sounds like with a 20-year plan that— and it could be 20+ because we're not young, but we'll be in our 50s in 20 years. A lot of CEOs are older than 50. So, it's not like you'd even have to stop at that point. You could ride it out another 20 years. So, I guess my kind of question in there or what I was just sort of validating was that it sounds like this go-around this progression of your journey, you're slowing down to like really develop your people and leadership skills and then cascade that and create like overlapping leadership. So what will happen in a relatively small organization is there's this person and there's this person, you're only one degree of separation and they're like literally right there. It's really hard when you're trying to develop this person to transfer that to this person, to not be like, just get the fuck out of my way, I'm gonna go tell him, right? So like, there's this weird kind of like sitting on your hands and waiting. It's like watching your kid fall off a bike. You're like, oh, that was messy, you know? Or you're watching somebody do the demo and you're like, bro, like, really?

You know?

And I'm not saying that your people— like, this isn't you. I'm just saying that that happens, right? Right. And like, your team will never be as talented as you. They will never be as capable as you. Again, we've established they couldn't be. They didn't go through every single Slumdog Millionaire moment that equipped you for this, like, time and space to be this person. So one thing I have a question for you— I know we're, we're rounding third base and landing the plane here, um, founderhood, entrepreneurship, it is such a mental game, right? Like, you don't dig ditches. You're not like all these construction workers or a lot of your clients where you have to get up and like do hard work, right? It's mainly here, it's mindset. What are some ways that particularly in these early stages that you like keep the faith, you know, when either times are challenging or even if you are well funded and it's not like financial struggle, but it's just like almost like patience, you know, and being like, well, it takes time to develop that part of the platform and it takes time to course correct that. Like, how do you not drive yourself crazy? Do you have exercises that you go through? Do you do meditations? Do you like have mind release? Like, what are some of the ways? Because I think there are people that are listening that might be in a similar season. They might not have the background of success that you've had, but they might just be like year 2, year 1 of their business. And they're like struggling, like emotionally. Do you have any cheat codes or just like methods that you go through on a regular basis to like keep the vision alive?

So I think, um, so firstly, I think sort of writing down where you're going to be, um, gratitude. Like, I'm grateful for our team. I would actually disagree that a lot of them are more talented than me. Danielle on my team a fucking rock star. Like, she's ridiculous. Um, Navrat, like, people on my team are way more talented than me. Yeah, I definitely wasn't saying to the point where I have to get out of the way. Um, I also think, uh, you know, and I definitely don't have the God complex because I feel like we, we, you have to—

you're paying—

I'm almost grateful that they're choosing to work here. There's so many places they could go, and it's like I'm almost competing with the market. Like, you know, I have like pay up. I have to pay market or pay up to get them because these guys are so talented. And like New York City, like they could go well-funded startups. The AI companies have unlimited money, you know what I mean? It's like hard to compete for talent. I think talent is where you're gonna win. And I saw Sam Altman wrote this thing and he's like, basically the elements of a successful startup. And it's like, one, the idea, two, the team, and then three, the product. And it's like, the idea has to be big and grand and it has to create a lot of value. And then you have to have the team to build it and then you build it and then you have the product. And sort of that's where we are now. We're sort of on, I think, step 3 and we're still perfecting the people part. I think the idea is like there, it's nailed. I think like getting the right people in the right seats, which is about the book Traction, which I thought was over there.

Yeah, it is.

Oh yeah, it is over there. So anyway, so I just wanted to say that. And then like, you know, I think saying like where you're going to be, having a plan, you know, I look at, you know, our numbers and again, I'll look at like our burn versus our cash and I'll be like, all right, we have this much runway. And the thing— so I don't look at just the cash. I'm like, how much runway do we have? And all I know is I need to buy us enough time to get there because I know that the product will get there. And then once it's there, there's going to be all these other things. So it's like, do we have enough time if we're burning $100K a month and we have $3 million? It's like, all right, we got 30 months. You know what I mean? And we're burning $150. We have 3, you know, it's like we only have 20 months. So it's like, how long do you have? What's your runway in order to figure it out? And how do I buy us enough time in order to— in order to actually get there? Because that's what we need. We need time, right? Time to build the product, to figure out how to sell it. Exactly. So I think about runway a lot. I write down like where we're going to be. A lot of times I'll write things down and like they'll freaking happen, like almost to like, right, super, super—

you're a manifestation master.

Yeah, it's crazy.

It's uncanny.

Yeah, you're—

it's wild.

Um, so there's that. And then I think, like, again, this time around, way different. I do, like, just going into, like, tactic stuff, like, I'll do a lot of breathwork stuff. I'll do a lot— I, I wish I did more meditation, but recently I've been doing a lot of saunas and cold plunges, mainly at Othership in New York City, which is a sauna and cold plunge in, uh, Flatiron. And then, um, that's awesome.

But like, sponsored by—

so I'll do stuff like that.

Um, so that's where you kind of find your grounding, your centeredness. Yeah, because it is challenging, right? Like, on one hand, you never want to let them see you sweat, so you have to kind of come into the space and not be neurotic or, or, you know, a bull in a china shop.

So by the way, that's something I have to get way better at because like, I know that teams need their like leader to be like safe and like have their shit together. And sometimes I, I do come in hot and I am scattered, and like I will kind of like come— like, that is something like I have to get way better at. Like, I think sometimes I, I do, uh, like react emotionally to something. A lot of times though, like, I, I also think I'm really, really self-aware, so I know like I did that. And usually like later in the day, be like, look, my bad, my bad. Like, but I'll be like, but you can see why I felt like that. I did feel like that at the time. And a lot of times it's like, yeah, I get it. And it's like, I'm sorry too. Like, I don't want to be a crazy person. Like, I want to not do that. So like, I do apologize how I came at you. But like, you know, and then it's like opens it up for a conversation. Like, you know, I was feeling that way because of this. And it sort of like goes into that like deeper conversation, which again, I never like used to have those conversations like that.

So you would just do it and then be like, that's your problem, like you carry that now. Yeah.

And like, I would be like more avoidant where it's like, all right, I'm not gonna like tell you how I felt. Yeah, like, you know, it's like, I fucking felt like that, but like, I'm not like that now.

Well, it sounds like there's an opportunity there. It's the classic, like, instead of using the word 'but,' you just replace it with 'and,' and it does this wildly powerful thing where you say like, hey, I, I felt that way, and I'd like to talk about how we can improve. So that— so like, by saying 'but,' it's like but like, get your shit together, you know? So you can just switch that word. I've learned that where I'm like, damn, that's like a colossal change in just being like, this happened, I did it, and now let's move forward. Or I've heard it this way, it's like kick, kiss, kick, where you kind of like give them shit. Or kiss, kick, kiss, where you're like, hey, you're the man, like, you're doing it. Let's talk about what is not going well. And by the way, Hey, you're doing it. Um, okay, final couple questions for you as we, we close out, and you kind of just answered it, but what right now— I'm gonna ask you a two-part question. I want to know what right now, as a company, as a leader, is just kicking your ass? Like, you are just getting like hammered every day to the face, because that feeling never goes away. It's just going to be a different thing. And then where's an area where you're like killing it, like I'm just slaying right now. You can choose whichever you want. Maybe end on a positive note. Um, yeah, what's just like whooping your butt every day right now?

Product velocity. Like, I want to move so much faster on product. Um, so product velocity is something that we need to improve on. And I think we're doing a really good job at go-to-market. I think we're doing— again, I think we can do a better job. Yeah, all of this stuff, right? I think like our funnel right now is like pretty healthy, you know, getting, call it, 1,000 leads a month. We're doing 80 demos, closing 40 sales. Like, you know what I mean? Like our funnel is like pretty good within the funnel. Everything can improve. So I don't even like saying it's good because I'm also unhappy with a bunch of areas, a bunch of things within it. But I think think in general when I tell people sort of about our funnel and all of that, um, all things considered, I think like go-to-market and sort of, uh, marketing and sales funnel is, is pretty good.

Yeah, you and I were talking about this at dinner the other night and it feels like you're— you, you proved this is— there's an appetite, like there's a, a real need, like it's not fabricated by marketing, or charm, or enthusiasm. It's like, objectively, the market needs this. You've gotten that both in your MRR, your customer base. You're way out of the, like, is this going to work? Right, right, right, right. That season we kind of alluded to.

I think your first 20 customers, you're sort of in that. We're at 200 now. Right.

You can't fool 200 people into giving you money every month.

Right, right, right. Exactly. I don't have 200 friends. They're not my friends.

No new friends. Friends.

Yeah, yeah, but I'm just saying, like, these are like people unaffiliated that like saw the value and like, you know, paid real money for it, right?

And continued to, right? It wasn't a one and done, like, I don't know if I'll go back to that, recurring. So now your, your game, your, your, your play is to like— I like how you laid that out with Sam Altman, right? Is it's like you had the light bulb moment there in Italy with Chuck, you built the team, you went and did what you had to do to get the capital put it together. Now it's like making Sharewillow undeniably the most badass platform for incentive plans, for profit sharing. And I love the connection between the fact that your client experience is their employee experience. That EX-CX, like, combo is, is really, really cool. So I appreciate you, man. You know, I love you. We go back many years, and I've always enjoyed watching your journey. Um, not your therapist, you know, didn't want to go too heavy there, but for the people that aren't familiar with your background, I'm glad that we got to cover some of that. And, and I appreciate you for being vulnerable in that and sharing some of those details, because I, I think it has informed who you are and made you this unique leader, this unique founder. And it's why I think you're going to build Well, not gonna, you are building a billion-dollar company. Yes, sir. Love you, bro.

Thank you.

Love you.