Ryan Rutan: Welcome back to the episode of the Startup Therapy podcast. This is Ryan Ran joined as always by my friend, the founder and CEO of Startups.com, Will Schroeder. Will, you've been an ad guy, a member of a typist pool, a salesperson, a carpenter, let's not forget multi-time startup founder, but like in a world where, you know, we were told like, pick your path. Pick your trade, go learn it and do it. Like, how do we even end up being founders, right? And how is it like somehow we keep running into all these founders who are like, well, but I don't feel like I'm qualified for this or I want to do something else, but this is what I know how to do. How do I reconcile that when that is kind of how we got here in the first place, right?
Wil Schroter: I agree. It's it's fascinating because, fun fact, most of The people that come to startups.com that are starting whatever company, a consumer products company, enterprise sas company, you name it, didn't come from that industry. You would think it would be part and parcel. You would think like it'd be 10% or something like that. But I want to give like two layers of abstraction for the folks in the audience. Number one, almost no one was a founder before because that, that actually isn't a job that you just get, it's one you create. I'll say it again. A founder isn't a job you get. No one gets the no one interviews for the founder job. You create the job, which means you always get hired.
Ryan Rutan: I was just thinking about like how many times has somebody had a headhunter called them and be like, hey, we're looking for founders, right?
Wil Schroter: Right. Exactly, exactly. So, but the second part of that is because you create the job, you are by definition inventing yourself in. case is reinventing yourself. Yet there's a massive amount of uh pushback that folks have on the idea of reinventing themselves. You know, you've got this kind of hardcoded feeling that we are this one thing, you know, I, I went to law school. I'm a lawyer, and that's what I am. No, that's just something you did. And so I think what would be, would be fun today is to talk about where this comes from, this notion of I can only be this one thing. Uh, what it takes to reinvent yourself and and we've done many, many,
Ryan Rutan: many, many times, even with a single startup, like within a single startup, I think that's something super important. It's like, how many times have we had to morph and evolve just because the startup did so, right? Like by nature, we know, like if your startup pivoted, which a lot of them do, you likely had to reinvent yourself at that point to survive the pivot because the business completely changes, likelihood. You need to change at least something at that point, right?
Wil Schroter: Absolutely, and I think what's important to understand, and I, I, I want to make sure we get into this, is every one of those pivots, those changes, those, you know, those reinventions becomes part of a bigger thing, right, becomes part of a bigger thing, and we become this sort of Swiss Army knife of capabilities and experiences. And personally, I embrace that. I've got a list somewhere. I'm gonna, I'm gonna see if I can, I can bring it up while we're doing our episode, but I've got a list somewhere. Job and role that I've ever had. It is hilarious. I made it for my daughter years ago because she was talking about what she wanted to become, and I said, uh, give me a day cause it would take me a minute to turn out, and I'm gonna come back to you with every job that your father has had in his life. And Ryan, I could, it was like 50
Ryan Rutan: things. Yeah, yeah, yeah, that's the thing though, but that's, that is our resume. Right, and all of those things come forward, right? Like, yeah, are you a carpenter every day? Well, right now, yes, so bad example, but like, you're not a carpenter every day, but you still bring your measure twice cut once mentality, the tools, the things that you've learned through that to what we do at a at a startup, right? It's, it's all of these things have their place. We don't stop being one. I think this is the thing when people get really caught up and scared about like reinventing themselves, like, we'll have to. Stop being that, you may stop doing that on a daily basis, but you're gonna stop being that person. I will always have done those things and so that will always be part of who I am.
Wil Schroter: All right, I, I, I gotta share this list. I'm not gonna go through all of it.
Ryan Rutan: I, I hope a big part of me hopes that you're actually just gonna start singing That's Life by Frank Sinatra and and go through the, I've been a poet, a popper, and
Wil Schroter: so I feel like this is in no particular order in this actual list. I, I actually put all the, the date stamps and where I did this, OK? Uh, you ready for this? I'm gonna read it fast. Commercial actor, podcast host, what do you say? basketball coach, high school teacher, telemarketer, sandwich chef, parking lot bouncer, casting director, college lecturer, digital art museum curator, creative director, database engineer, dungeon master, hockey player, radio DJ, triathlete. Uh, public company board member, school mascot, head of business development, BBS CISO, dude we go our reality show finalist, middle school teacher, children's book author, carpenter, CFO, nightclub owner, receptionist, president, SBA Young Entrepreneur of the Year, professional speaker, RPG game designer, 3D modeler, architect, nightclub promoter, interior designer, general contractor, software engineer, field hockey goalie, and this list goes on. I'm not. Like
Ryan Rutan: I, I feel based on, I, I think you missed one, and this is all very recent, a crash test dummy. I feel like with your luck with vehicles lately, that that you absolutely have you've at least been doing some engineering testing for a couple of major companies.
Wil Schroter: Hey, by the way, you know it didn't make that list? I mean, it's on the list, but say, founder. Oh yeah,
Ryan Rutan: I, I was waiting for it, yeah, didn't hear it. Yeah,
Wil Schroter: that was without even saying like what you got
Ryan Rutan: that one yeah, parking lot bouncer, rumor has it it was a Chuck E. Cheese. Is that accurate?
Wil Schroter: No, that was my first job. My first job was, it was for a pizza place in Connecticut. They had a parking lot situation where everybody kept using their parking lot. So the owner, uh, Lino paid me like a few dollars an hour to kick people out of the parking lot. We weren't supposed to be parking there. And I was, I, I was like 12 years old at the time, you know, trying to, trying to be a bouncer and knock people out of parking lots.
Ryan Rutan: Um, but there's some interesting lessons learned there, I'm sure.
Wil Schroter: But let's talk about reinventing yourself, OK? Because every one of those were jobs I had, mostly jobs I got paid for, and all of those required me to have some learning or expertise in order to have those jobs and do those jobs, but that's not even all of them. Like I said, I only got like halfway through the list, right? And I'm laughing because I haven't looked at that list in years. I just brought it up right now. I thought that would be fun to see. But it tells a story of how we are both what we make ourselves, but as importantly, a composite of all the things we try and, and, and taste test and get into, but we're also not limited. I don't have like any special capability that anybody else doesn't have, right? Like I'm just very willing to try everything, but to just say, cause I feel like, I don't know, Ryan, like. At some level, yes, I have the identity of a founder, but to me that's like saying I have the identity of a creator.
Ryan Rutan: What I, yeah,
Wil Schroter: right, it, it just says directionally like to build stuff. When you think about yourself, and you think about some of the different directions you've gone, what are some of the highlights that that come out?
Ryan Rutan: You know, it's interesting. I mean, the, in in terms of the directions I've gone. I have to give that some more thought in terms of like the the the highlight reel there, but there's an interesting thing that I found, and, and I think it was like the point at which I started to want to reinvent myself, were places where all of a sudden I realized that like, it had become really familiar and maybe safe as a result, like this this sense that like familiarity equals safety, right? Like, I'm a lawyer, I'll just always be a lawyer and that's somehow safe. And and what I realized was that it was just sort of complacency or wrapped in inertia. And, and I didn't like that. I, I didn't like that. So for me there have been these like these triggers where it's like, if I haven't been pushed or haven't had to try something new, or I haven't failed at anything in a while, like I get really uncomfortable. I'm like, I get, I get uncomfortable with the comfort. It's like, OK, this has just become commonplace, right? Like, you know, the minute I, I, I, I master something on a relative basis, I'm like, I'd like to move on. I wanna try something else, and that's probably part of the founder ethos in in general.
Wil Schroter: You know, I, I think what's interesting is, um, a lot of our career is shaped by what we have exposure to, OK? So, so let me give you just a a a quick little vignette that's always just inspired me. Years and years ago when I was pursuing one of my job titles, which was board member of the Rock and Roll Hall of Fame, um. Super random people like, wait, what? Yeah, they they they had recruited me to become, to join the board of the Rock and Roll Hall of Fame and the the most flukish opportunity ever. It made no sense for anybody, but the reason I'm telling you that is because as part of the recruiting process, they would give us tickets. To these private concerts. So like when someone got inducted into the Rock and Roll Hall of Fame, there was a public concert, there's also a private concert. One of the inductions we got to to be at, which was amazing, was Metallica. Oh wow. It was unbelievable, right? It's like 200 people in a room. And me and my wife, like two idiots from Ohio, like, what, what are you doing here? Anyway, that's the point of the story. So Lars Ulrich, who's a phenomenal, phenomenal drummer, right, and, you know, just like a a rock god in his own right, went to Juilliard, by the way, like, like not a, uh, and I think they put out classically
Ryan Rutan: trained rock god,
Wil Schroter: yeah, yeah, I was like, but I think like, like they put out their first album, I think they were 18, if my memory serves me anyway, he's sitting up there. And he's like kind of teary eyed, and he's he's giving a speech directly to his parents sitting in front of him, and he said, uh, you guys were always playing music in the house, uh, when I was growing up, right? You made music a a part of things, and Ryan, I I always think of you and your family, because I know there's music in the house, etc.
Ryan Rutan: I've got an anecdote I'll share right after this. It just happened last night.
Wil Schroter: But, but here's what he said. He said, Mom and dad, I'm here. Because of you, not everybody wants that. Heather could be a drummer of all things, you know, I've
Ryan Rutan: actually resisted that one specifically because it's
Wil Schroter: drums. And so he said, but, but I'm here because of you. And I remember when he was giving that speech that like everyone's like teary eyed because like it was one of those amazing things to turn to your parents and genuinely thank them for the highest achievement you've ever made. Like it was incredible. But, but beyond that, I just kept thinking as he was saying it. I was like, what if, what if his parents were a bunch of dicks and they were like, no drumming, right? You're gonna be
Ryan Rutan: on stuff, Lars, it's noise the shit out of me.
Wil Schroter: Like, back to the abacus and like, and but, but what if his parents, you know, again, talking about like how we could become anything, we're just like, no, you're not a drummer, you're an accountant, and I'm not not an accountants, but I'm just saying like, but like
Ryan Rutan: if you can be large. Or an accountant belars please just like God's sake.
Wil Schroter: What was your vignette? You said you had an idea.
Ryan Rutan: Yeah, so last night, and it's, it's interesting cause it's a nice illustration of this. So yeah, we do a lot of musical stuff. The kids, the kids by and large like to perform a lot, but kind of your point, his parents weren't stuffing drumsticks into his hand either, right? They weren't like, you become drummer, right? They weren't Tiger Woods' dad was like, you will play golf or die. Uh, I think that's how it went. I don't actually know, he's probably a great guy. So last night, for the very first time ever, Jack decided, I was out playing piano and the girls come out and we're singing a little bit as I was playing, and then Jack shows up. Now Jack loves to play piano with me, loves to sit down, he's he's learned to accompany me, he's he's 7, he loves to accompany, and then all of a sudden he was like, Dad, you know the song that won the Eurovision this year? Wasted Love. It's like, yeah, yeah, do you know it? I'm like, no. He's like, can you find it? So we found it, we started playing it. He wanted to sing it. He's never done this before, but the girls love to sing. My wife is amazing singer, and so just like he all of a sudden wanted to do this, and we have this beautiful I I will share with you. I will not put it out on on broad social, but I will share with you the week Nargis just grabbed like a little clip at the end of him singing. It was so beautiful, but one of the most beautiful parts of it was she recorded this, and dude absolutely hits the notes at the end, which like, I love that and it made me really proud. What made me more proud was the entire family erupted into like just full on joy at him hitting that note. The girls, you hear the girls in the background, you hear me shouting, you hear Nargas screaming because he just crushed it. But it's such a cool thing like that is now part of of Jack's fabric, right? Like that is part of what he was. exposed to, and it will become part of who he is. Now, does he become, uh, you know, a Eurovision star? I have no idea and I don't care, right? But because of that exposure, but also because we didn't force it on him, like I, we all had the friend who's like, couldn't come out to play because he had to go to piano lessons and hated his parents. Great pianist now, I I they love to hear him play, but like, it was a very different thing. So I think this this this notion of exposure is super important.
Wil Schroter: Well, I I also think there's this conditioning. That we all come up with you, you mentioned it just when you're saying, you know, the parent who makes the kid play piano, whether whether they love it or not. I say this to say we've all been conditioned and have a bias of our of our upbringing, um, that comes from wherever it comes from, but how we choose to manage that bias makes us who we are. I grew up thinking that I would become nothing. But I wasn't willing to to live with that bias, if that makes sense. Right? Like expectations for me were at an all time low heading into life.
Ryan Rutan: I think that's super important because I think that, and look, we can, we can assume we're gonna become nothing, we can assume we're gonna become something great, like whether our parents are the ones driving that discussion or we're the ones driving it, and somehow we like from a really early age and relatively speaking, could be the start of your career, could be start of your recreation, but we start to pretend that we can draw these like really straight lines. Around what happens, when in the reality life and career is just like this series of scribbles that are really hard to connect until you can lean back. Sometimes you see a pattern. But I think that's, I think that's a big part of it, right, which is being willing to say that like, look, all these things are gonna form who I am. I don't have to accept it because I took piano lessons as a kid, I'm going to become a pianist. I also don't have to decide that I'm not going to do that, or right, that it isn't part of who I am, right? It it's all, it's all in the batter at the end.
Wil Schroter: Well, so, um, like I said, we easily get stuck, and I think as we get further into our careers, it hardens. That that concerns me the most. Somebody believes, you know, they're 32, which isn't that old, especially within your career, it's like the first quarter of your career barely.
Ryan Rutan: I thought you were gonna say it, which isn't that young, because I was thinking about how young I was, I was like, no, it's not that young.
Wil Schroter: You're early in your career and like, oh, you know, this is all I've done I will pick out accounting. Um, all I've done is accounting, and now I want to do this thing in consumer packaged goods. I've I've been done. Into this new new
Ryan Rutan: product, but I'm an accountant.
Wil Schroter: It's like, no, you did accounting, you're not an accountant, right? Like it's, that's not how this works. And I know for myself at first I didn't realize like I didn't think I was meant for anything, so like any work I was taking was good enough for me. It was like if it was paying, that was my job
Ryan Rutan: parking lot bouncer, fantastic. Done,
Wil Schroter: done, like, oh, OK, so hold on, let me pause there for a second. I just gave a kid his first job this past weekend, a family that that that we're we're real close to, and they've got a 15 year old son. He's actually been previously in my entrepreneurship class in school, uh, great dude. He was trying to figure out what he wants to do for the summer. And I said, well, hey, on the weekends, if you're free, I'm building a house, if you want to come learn carpentry, etc. I happy to take you out and pay you. But, but here's what he said, and he's right, by the way, he's. Like, what does it pay? And it's so funny, Ryan, because like it's a very reasonable question, but I would have never asked that at 5. like what I would have said is, do I get paid? Yeah yeah
Ryan Rutan: yeah its
Wil Schroter: fantastic. Like, like my credo was if it pays the answers, yes, then you can tell me what it is or how much I get paid, right? Just different era, but, but I thought that was funny, but he shows up on Saturday. And, um, and, and I'm have him do work around the house and he said, hey, Mr. Schroeder, it's weird that he calls me Mr. Schroeder. I was like, What's up, man? He said, What was your first job? And I told him, you know, this parking lot bouncer. And I was like, uh, Tim Cho, what's your first job? He said, uh, this is it. I was like, bro, this is your first job? Yeah, yeah. He's like, yep, this is my first day of my first job. Like, man, that's a lot of pressure. I'm gonna have to, I'm gonna have to drop some nuggets, some golden nuggets of
Ryan Rutan: that's right. This is, this is no longer, I'm no longer an employer. I'm a mentor. Damn it, yeah, damn
Wil Schroter: it, you made my life harder.
Ryan Rutan: Anyway, you can add to your list of 50 now. You can uh child labor crew manager. Oh no,
Wil Schroter: this is, this is so funny because when I, when I was working with him, I was showing him how to do framing, like doing framing, and I said, Tim, have you ever seen the Karate Kid? He's like, oh yeah, the Will Smith movie. I'm like, god damn, dude. He said, oh yeah. Old movie with Will Smith. I was like, no, it's like no, and I was joking to him. I was like, my fear here is that I'm gonna teach you all these cool skills, but you will not know karate at the end of it, and he totally lost on him. He didn't understand my Mr. Miyagi at all. But the whole point of that story is that right now he's figuring out who he wants to be who he
Ryan Rutan: thinks he wants to be right for today.
Wil Schroter: But you know what I'm explaining is that. The field is wide open, man. And here's what I say, be lots of things, be lots of things, so so that you can counterbalance,
Ryan Rutan: which is so funny, right? Like we sort of understand that at the beginning because we're not bound by anything, right? At the earlier stages, at the early stages it's like, well, OK, I can, I can be whatever I want because I'm not anything yet, right? So this is where like we we know that like. Curiosity starts to die, Creativity starts to die as we get older, like on a relative scale. Some of us are still very creative, some of us less so. But I think that like, we have to start thinking of those experiences and that resume as an inventory, but I see so many people, particularly founders, because they want to make a big change to your point. They come from one industry, they want to do something completely different. But instead of treating that as like a tool kit and an inventory, they treat it like a chain, right? And it and it holds them to this place that they're in, which I think is super, super painful to watch.
Wil Schroter: Yeah, absolutely. Let me expand on that. We tend to think who we are as solely uh put toward our um our career, what we get paid for, right? When I tell people I'm a carpenter, they're like, oh, you do carpentry for a living? I, I was like, I don't get paid for it, but I probably do more carpentry than most carpenters. Like it it doesn't like me getting a check for it doesn't doesn't like make me a car.
Ryan Rutan: It's not what defines it,
Wil Schroter: yeah.
Ryan Rutan: Yeah,
Wil Schroter: exactly, right? Any more than your wife getting paid to perform, um, makes her a performer or not. I mean, she's she's she's great at what she does, but the, the, the paycheck doesn't change it. Exactly. I say that to say most of us only have one or maybe two things that we can do, the capabilities we possess that are payworthy, um, again, like because we understand accounting or law or something like that. But that doesn't define the constrictions of of who we are, or who we can be. I've had like 50 careers, some of them paid, you know, some of them pursuits. Me choosing to go, uh, professionally with it, or, you know, you get paid for it is incidental. The reason I bring this up is because I think a lot of people associate their identity. With what they get paid for.
Ryan Rutan: 100% they do, right? Uh, it's again, some people, I would argue most founders do, at least at the point where they're making decisions around what they're doing with their lives as founders, right? because they're they're saying I'm now gonna go do this other thing that's completely different than what I've ever done. Go back to that whole like safety, familiarity dynamic that we talked about. Earlier, I get all feeds together and they start to say, well, because that's what I did before, it's what I, I should keep doing and and now that's who I am because that's what I got paid to do, which I think is relatively easy to understand, like why it happens, right? This is, this is how the world values you monetarily.
Wil Schroter: I get it. I, I, I think early in my career by accident. I got pulled into lots of things that I somehow got paid for because I was like hustling, right? I was just trying to figure anything that would make money. And so if it made money, I would figure out how to do it. When I graduated high school right before I graduated high school, I got two full-time jobs. During the day I was doing telemarketing essentially selling mainframe computers, and at night I would go make sandwiches. And so neither of those was a career that I wanted to have forever. But they were the first person that offered to pay me anything and so I just became that.
Ryan Rutan: I don't have a job now. I don't have money now. You have a job that offers money. OK, that'll work. That those were, you checked both my boxes.
Wil Schroter: You know, something that's really funny about everything we talk about here is that none of it is new. Everything you're dealing with right now has been done 1000 times before you, which means the answer already exists, you may just not know it, but that's OK. That's kind of what we're here to do. We talk about this stuff on the show, but we actually solve these problems all day long at groups.startups. Dot com. So if any of this sounds familiar, stop guessing about what to do. Let us just give you the answers to the test and be done with it. But what was interesting about it, and this is really what kind of set me off like I'm just this chain of events, was that it didn't occur to me that I couldn't do something, and that wasn't because I was bursting with confidence. I it was just more ignorance. I just it. I didn't know enough about what that thing was. I'll give you an example. So I'm 17 years old, I get this job, I'm selling mainframe computers. Now it just so happened on this bizarre chain of events going through the 80s and what would now be the early 90s, that I knew way more about computers than most of the people at this company that I was working for, right? Cause I just got into it early, right? Another chain of events. And so I get on the phone. And mind you, I'm 17 years old. My voice is like this, but I'm talking like this, right? And but it's all over the phone, so no one knew. And so I'm calling what used to be considered MIS managers. If you can think back to your Ohio State MIS was and I'm basically saying, hey, do you need, um, memory. Boards for your DPS 9000 bull Honeywell machine, whatever it was, right? And they're like, yeah. And so I'm like, OK, well, I'll just, I'll go write up a quote for it for $20,000 and, um, I'll send it to you. And my boss is like, what are you doing? You're, you're supposed to call, you know, and see if there's a lead and then pass it over to me. And I'm like, well, if he says he wants the product and we have the product, we have to sell it to him. Like that isn't that what we're doing here? Yeah, right. And, and I remember that the, the president of the company of this this computer company was like, wait a minute, you just closed all your own sales. I was like, yeah, what else would I be doing here? Why else on the phone, right? And, and I wasn't saying it I like being cocky. I actually just, I was, I was like,
Ryan Rutan: Hi, you wanna buy something? Yeah, OK, we'll call you later.
Wil Schroter: And so, president of the company and it took took me under his wing. And he was like, I, I'll never forget, he's like, I'm gonna make you the deal of your life. I'm like, Oh, Donald Trump, what, what have you? He's like, I'm moving you get this right. I'm moving you from $5 an hour to $10 an hour. You will now have a sales quota,
Ryan Rutan: your income, but you'll now have a sales quota at $10 an hour.
Wil Schroter: I had no idea that I could ever make $10 an hour, and number two, I actually didn't notice. Sales quota was
Ryan Rutan: Yeah, didn't matter. I, I know, I know what the doubling in in my hourly pay is and whatever it needs to happen, I'll do that.
Wil Schroter: You had me at quitting my sandwich job. What was fascinating about that experience, and I say this because these things come in such like non-specific random ways. Ryan, next day I wake up and I'm computer sales guy, and I'm like, how the hell did this happen? What happened? Yeah. And I, I started to watch this pattern in life of what it takes to reinvent, OK? And it always started tiny. It was never this big thing, and I think this is important. It was never this big like overwhelming commitment, right? I'm now a dancer, right? It was never that. It was a tiny event, you know, the, the whole idea of how do you move a mountain one pebble at a time, a tiny event. That just imperceptibly at the time shifted me towards something and became something more. Have you gone through the same thing where like, I mean, think about it like what you did here, like when, when you're doing, uh, sales initially and we needed help marketing and you're like, yeah, I can help marketing. Right, you started to chip in and now you're a CMO. Yeah,
Ryan Rutan: I think it's been largely the same thing for me, man. It's like you, these little opportunities come along, right, to maybe kind of stretch things a bit. Step into a step into a room that you you haven't been in in the past, like there's just little tiny things. And, and I guess in my case, a lot of it came from some of it just came from necessity, right? Like something needed to happen. I'm like, well, I'll try to do that. Do you know how to do that? Well, I'll try to do that, or things where it was like maybe even personal necessity like I want to go do something else. I want to be somewhere else, but In in most cases, going back, it was less about necessity, more about curiosity, right, and desire. Like it was like things that I I wanted legitimately wanted to try and and I think that like kind of in your own case, you know, in that one a little bit more opportunistic, but in the story you're telling. It came from prior knowledge of computers, right, which came from your curiosity, right, and at a time where you were a kid and you could just explore, kind of the same thing for me, and we were both kicking around, you know, TRS 80s or whatever back in the uh uh back in the early 80s, and
Wil Schroter: so like, think about your journey here. Yeah, right, you didn't join as our CMO? No.
Ryan Rutan: No, no, no, no, I, no, no, started started on the phones talking to folks and doing some consulting work, then went over, we realized we needed to to kind of reframe the entire consulting division, jumped in on on that side, and then uh that led to, gosh, what were they like that's actually pretty funny if you look back through the the LinkedIn, there was like content, innovation. Uh, I feel like there was another, another one in there somewhere, uh, and then, and then eventually, you know, CMO, and so, but, but this is like it's, it's so common, right? Like it doesn't that, it's funny to me that it doesn't feel funny. I think other people that and go like, what the, right? That just feels totally normal and natural to me, like, well of course I've done a bunch of different shit. We've been doing this for 15 years. What do you think like, I'm not an accountant.
Wil Schroter: Yeah. Well, OK, so think about it like this, the more we realize that we can take on something else, the more it exacerbates that feeling. I'll give you an example. You know, you've watched me through this journey becoming a carpenter, now a general contractor, architect, 3D modeler, like, you name it. And you know, when, when I walk people through this house that we're building, I'm highly specific about all the different parts of the house, about how like I designed the electrical systems or the network map or like you know how we did the architecture a certain way. And they're like, how do you know all this stuff? Right? Like how are you the GC of this, the general contractor this thing? And I was like, I didn't, I didn't know any of it. That's the point. The, the point is I knew none of this going into it, not even a little bit, and no one schooled me on it either. But you know, like as we were getting into the architecture, I had this idea, this caveman painting of what this house would be, and I brought it to an architect and the architect gave me something totally different than what I was looking for. And so I brought it to another architect. And after months and months and months, he gave me something totally different and I'm sitting there getting frustrated. By the time we're at the 3rd architect, if you remember this right, and this is like years into the process. I, I see this, this, this guy on the team and he's doing like a 3D model of, of the concept of what they're trying to put together. And I asked him, I said, hey, how, how are you doing that? I said I'm using a program called Sketch Up. Sketchup, right, right. And I was like, I was like, you know, I, I've used that a little bit for woodworking in the past. Let me figure it out. Now, nobody in their right mind would sit down and say, I'm gonna learn how to do 3D modeling architecture. I'm gonna design my literally design my own house, and it's a good sized house. So like, it's it's, it's a lot to take up. The same person wouldn't say. And I'm going to build it myself and I'm gonna learn how to build cabinetry and I'm gonna learn how to, you know, do all these things and do it all myself. The reason I was able to do all that stuff is because I started really small every single time. That's been my super like secret move to that long, long resume that that I read off. What I learned is you can do almost anything. If you start with the 1% at a time, that that's what I think is fascinating, and I, and I try to teach my kids this. I try to explain to them that that the journey through everything starts with a single step that's the most basic, unintimidating step, and I'll give you an example there cause I shared this with you earlier today. My son comes to me in in in one of you were talking about Jack coming to you and so I you know Will comes to me and he says, Dad, I found these nunchucks in storage, right?
Ryan Rutan: The fact that that was even something he could say makes me really happy. I found these nunchucks in storage. Of course you did, son, they've been waiting for you.
Wil Schroter: Anyone in our audience that may have been so fortunate to grow up in the 80s, likely went through the same ninja training that I did, whether it was foam rubber, stars, nunchucks, bota skills, computer hacking skills. Yeah. Anyway, he comes to me and he's like, Dad, do you know how to use these? I was like, buddy, if you knew and we put on Bruce Lee video. I was like, this is where this is supposed to go and let your father show you how to use the nunchaku. So I'm, I'm whipping him around doing all this crazy stuff, like literally living my eight year old self again. And he's like, Can I learn to do that? And I said, yes, yes, one step at a time. Ryan, what does he immediately do? Spins it around, hits himself in the
Ryan Rutan: eye right in the face. Yeah, I mean like that that is lesson one. That is lesson one. None. Comes back, right? that's what you learned that that that which is spinning comes around.
Wil Schroter: Dude, almost on cue, my daughter Summer picks up another pair and spins it around.
Ryan Rutan: Wait, you had, you had enough for full combat? You had the combat set. You had more than 11
Wil Schroter: does not only hold one pair of nunshots, true, true. It's clearly you need backup. anyway, thankfully they're phone padded. Point is, you know, even in something as silly as I tell the story just because it's a funny story, but when I tell him whenever. We're getting into anything is you can absolutely do this, you can absolutely reinvent yourself, so long as you start with one tiny step, little bit little bit and let those build progressively. And I've used that technique to get into a dozen different industries that I had from pharmaceuticals to entertainment, you name it, right? I've used that technique, especially now combined with AI to be a learned stuff, I should have no business even 1%. No. Right. Right. Like when I had to do all the electrical engineering for this new house, you know, it's it's there's a lot of house there, there's a lot of electrical engineering. When I was doing all the load calculations and everything, the electrical engineer is like, how the hell did you do any of this? I'm like, I don't, I don't even know what it means. I just went to chat GPT. I, I put in all my inputs and, you know, and and I got load calculations. He's like, it's spot on. I'm like, well, you don't blame me, play chat GBT. The point is I can now do stuff that I would never. Be able to touch before. It's awesome and I think it's an important fundamental skill for founders to have.
Ryan Rutan: It's probably one of the most important, right? Because again, like if you're setting out to build something that's never been done, forget about like all the kind of requisite skills you have to have. Like you have to know how to code things, you have to know how to design things, you don't have to, you have to understand finances, understand management, leadership, all that stuff. That's great, but there's always gonna be that layer of, but no one has ever built exactly what we're building right now in the way that we've built it. So it is a process of invention, and so like I think again, to your point, having that muscle that says anytime I want to do something new, I'm gonna start with what's the most basic step I can take, and then how do I build that into 23. 45, right? Like, how do I go from just being Nanchakka to Bostaff and knowing how to sharpen my own cow traps and, you know, all that stuff, right? So it's it's important, but you gotta, but you have to take it, you have to take it stepwise just like building the startup. We are building ourselves. In parallel as much as we are building the startup and it it requires reinvention. I know very few founders who've built something that I would say is like super interesting or like of course like if you were an accountant and you're like, I'm gonna go start an accounting consultancy. Yeah, right? Like, of course you knew how to do that. You were already in one. But if you're an accountant and you're like, I'm gonna go build an auto optimizing personal finance widget, um, that listens to household conversations uh through your Amazon devices to figure out how we could better manage your finances. That's something totally different, and just because you have an accounting background and understand the financial piece of it, doesn't mean you know how to do any of the rest of it.
Wil Schroter: But right, let's talk about how all these stack. What we've been talking about is, hey, you're doing this, but now you're gonna do this thing. What I think is most fascinating, I, I think what has been the the cornerstone of our careers has been how all of those different Facets and personalities and job titles have come together to make us the Swiss Army knife that we are today. My curiosity across so many different disciplines and industries, etc. has actually made me a really good start-up advisor because 90% of the time when I get in front of a, a founder, the world that they're in. I have some direct connection to, right? It's very rare that they say, hey, this is what I'm working in, that I haven't had some experience in that field, not making me an expert, just having some sort of connectivity. And when I look back, I would probably tell you that it wasn't until like my 5th career change, that all the pieces started working for each other. Let let me explain. I told you I took that job, uh, telemarketing. In that job. I was learning sales, but it turns out I was already great at sales because in the, in the previous roles that I had throughout high school, they were always presentation worthy. I was always person on stage. I was class president. I was always person like pitching, so to speak, right? And so, so that kind of helped me in what would become a formative sales role. Well, that sales experience that I gained from a job that I really didn't even want, which was the telemarketing job was. Paramount in when I started one of the first interactive agencies, I'd be able to go in in front of clients and pitch right at 19, how many 19 year olds have pitched anything? I've been pitching for years, right? Like I was actually pretty good at it.
Ryan Rutan: I pitched a couple fits at that point. I, I, I too had had a lot of those same kind of roles where it's like I was responsible for pitching stuff. I was the ideal person. I had to go and go convey the the ideas to the powers that be to make them do what we needed them to do. But yeah, most, most people will not have gone through that at that age.
Wil Schroter: And then when I started the agency, yeah, you started one as well, so you can appreciate this. Yes. All of a sudden I had 3 disciplines, technology, marketing, and design that I needed to be good at all of them cause I was the only person working there. God,
Ryan Rutan: I, but man, how much more did you love that phase? Then I literally felt like I was being drawn and quartered or whatever the hell drawn into three pieces would be at some point that that was literally when like the impetus for me to, to stop. Having the agency came. Luckily an opportunity to sell it came along, but like, there came a point where just having to manage those three distinct disciplines, being able to speak their languages was the core skill. Like, I knew the job, I knew all three of the jobs, so I could keep them from killing each other. That was, that became my role.
Wil Schroter: But, but who would have guessed that technology, marketing, and design are the fundamentals of being a startup founder, right? It just so happened that those three disciplines around. On product in UX design around customer acquisition, and of course around technology for a lot of what we build, would become the cornerstones of being becoming a startup founder. Like, didn't see that coming.
Ryan Rutan: Back to my straight lines versus scribbles thing, right? Like this is exactly where that starts to come into focus.
Wil Schroter: And and I guess because I embraced all of these different roles, if I were to like kind of peel this back to to at a core what I've always been, I've always been a creator, right? I'm just a creative person. I like creating things, whether I'm writing, whether I'm building. where they're designing a new company idea, whatever. I just like it in creating and inventing stuff. And it didn't really matter what it was, still doesn't, right? I don't care if I'm building a house or I'm building a company. I just like building stuff.
Ryan Rutan: Yep.
Wil Schroter: And because of that, I never really tried to pigeonhole myself to say, well, I'm just gonna build technology. I'm just a coder guy, right? Or I'm just gonna do UX design. I'm just that, that person. I was like, I don't know, I like to create. I'm just gonna do
Ryan Rutan: everything.
Wil Schroter: I
Ryan Rutan: want as many ingredients
Wil Schroter: as possible.
Ryan Rutan: For,
Wil Schroter: yeah. And and I would say, Ryan, at this stage in my life, uh, now that I'm in my ripe 50s, I am more open-minded to exploring how to learn more stuff than I have ever been, because now I realize the value of the composite, you know what I mean?
Ryan Rutan: Yeah, yeah, well, and what a lovely time to come to that discovery, given that we've got more ability to learn at our fingertips than ever before. Like, I've been having this challenge lately where I keep running into people who I would say are like underinformed, under-skilled, like they just don't seem to to know how to do things, and I keep, I'm just like, but how? Like you've got all of this, like, if, if I could get one more thing out of life right now, one more thing, if somebody was like, OK, we will grant you something, what would you love right now? I'd be like, could I have 5 more hours added to the day where I can just lock myself away. And learn things and nerd out. Like, I literally want to go back to like, and I'm sure you remember this too, like when I was 1516, 17, I could direct a lot of my time. Now, we, we had the farm at that point, so I was working hard for sure. I was also building the, the, the, the first tiny tech company, and so there were a lot of things, but the part of that was the exploration, like the tech company came out of me nerding out about databases and connectivity and and and accounting systems, right? And so, like, part of me, like that's the thing I would really love out of life right now. If you just have a little more of that, like, lock myself in a room, and I did this like 3 Sundays ago. I was like, all right, family, normally this is you time today, it's this guy time. I just spent the day with NAN. I was just like, I want to sit down and really just like figure out how to build a couple things that I, I think are possible, but I haven't had a time had time to do. And that's it, like, because there's so, there's so many tools out there right now, so many interesting ways to connect information, so many things we can go build, and the ability to do it's never been, never been higher. So great time to come to that realization, will.
Wil Schroter: But I say then also comes with um a freedom of letting go. The the the freedom of of stopping and saying, wow, I'm actually not just this one archetype. I'm not, you know, just, just this one thing, and I don't think for a lot of people that's heretical like like. What are you talking about? Again, I, I'm an accountant, I'm a lawyer. I mean, no, you understand law, that doesn't make you just a lawyer, right? You're not this one thing. And when you let that go, and you say, hey, the past is the past, you know, uh, my, my future and my resume is when I make it. That opens up incredible doors. And I think as founders, Ryan, like, can you imagine a founder that that doesn't give themselves that latitude? That's dangerous to me. It
Ryan Rutan: it's, it is dangerous and and we do see it, right? And like, to me it's, it's always like, I think it comes some of it goes back to that safety thing, right? They're like, look, this is what I knew, this is what's gotten me to here, so this must be the good thing, right? So I can't fully let go of that. And at some point you're just watching what's happening as a result of that inability to let go, and I always see the same metaphor in my head, which is like they're holding onto the anchor thinking it's the ship, right? This is the thing that's gonna get me where where I'm gonna go, and it's not, it's the thing that's gonna keep you where you are and in fact it's gonna, it's instead of keeping you safe and keeping you above water, I think it's gonna sink you. I see this all the time. Talk to a founder either late last week or early this week, absolutely suffering from exactly, so I hope they're listening. I will definitely send this episode, but the same kind of thing. It was like, well, because this is what I already know, I need to lean on this because this is what people know me for, this is what they believe. I was like, but it's not that connected to what you want to do, right? And they're like, yeah, but I've got to find a way to make this the foundation. Why? Like, and because I think it just comes back to safety.
Wil Schroter: I, I agree, and I, I, I think safety is not a luxury, uh, in, in our business, right? The nature of being a founder, when, when people say a couple words that come to mind, safety is never one of them,
Ryan Rutan: not the polar opposite.
Wil Schroter: But let's say it like this, Ryan, if we're in the business of inventing, creating things that have never been created before in markets that have never existed before, teams that have never existed before, it would stand to reason that the thing we should be most concerned about reinventing and creating is ourselves. And I think if we can't put ourselves in the mentality that anything is possible for reinvention, that anything can be changed based on what the the markets are or what our passions are, then that's not really synonymous with being a founder. So I think for all of us, being able to to zoom out and say, what I've been isn't who I am, what I want to be is who I am, which is the fundamentals of being a founder. Then we set a path, then we set a course which allows anything we could possibly imagine to be possible, especially with ourselves.
Ryan Rutan: Overthinking your startup because you're going it alone, you don't have to, and honestly, you shouldn't because instead, you can learn directly from peers who've been in your shoes. Connect with bootstrapped founders and the advisors helping them win in the startups.com community. Check out the Startups.com community at www.startups.com to see if it's for you. Could be just the thing you need. I hope to see you inside.