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The "No BS" version of how startups are really built, taught by actual startup Founders who have lived through all of it. Hosts Wil Schroter and Ryan Rutan talk candidly about the intense struggles Founders face both personally and professionally as they try to turn their idea into something that will change the world.
TST EP 272_Should Kids Follow In Our Founders' Footstep
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Speaker: [00:00:00] Welcome back to the episode of the Startup Therapy Podcast. This is Ryan Rutan joined, as always, by my friend, the founder and CEO of startups. com, Will Schroeder. Will, we've spent nearly 300 episodes talking about the journey of a founder. We have walked miles and miles and miles in the shoes as founders.
Is that a journey we would want our children to follow? We want them to follow in the footsteps of these worn out old shoes.
Speaker 2: I want to say yes. And then I'm also thinking, why, like, why would I bring them into this hell?
Speaker: It's all every time I'm, I'm in that little, I'm in that Looney Tunes moment where I've got the devil on one shoulder and the angel on the other.
Right. And I'm just like getting kiss on one side, jab with a pitchfork on the other. That's like, it's, it's tough, right? It's a really, really tough thing. I mean, clearly we've made a life out of this and I think I love most of it. There are times where you think back and you're like, Is that really what I would, I would wish for these little souls?
Speaker 2: Let me be the set up on this one. So, Summer, my 12 year old, and I are sitting, I [00:01:00] have an ice cream, uh, over the weekend. We're talking about like, there was um, some shops in this little downtown that we were at. And we were talking about how the fact we're building a new house right up the street. And Summer was saying something to the effect of like, Hey, maybe she'll end up going to work at, you know, one of these little shops.
And she's 12 now. You know, so she's got a minute. Right. And then I asked her, I was like, Oh, you know, would that be a cool first job for you? Like, what would you want to do as, as your first job? Cause you're not that far off, you know, from having a job. And she looked at me deadpan, like without any question, she's like, well, I'd want to work for myself.
Right. Yeah. And like, you know, right. As who we are and like what we do, it's like, like greatest moment ever. I would say there was definitely a little
Speaker: swelling of pride in that moment. You're like, yes, that's what I wanted to hear. Not just what I want you to do, but it's what I wanted to hear.
Speaker 2: Yeah, exactly.
And like. And obviously I love that answer, right? Yeah. But there was this really weird kind of like hallucinogenic catharsis that I went through immediately, right? Like as she's saying that, and I'm about to come back with like this high five moment, I went through this series of emotions that started with best news ever.
[00:02:00] Absolutely. This is what you want to do. Are you nuts? Like this is the most dangerous thing you could possibly do. Is this really even my call? And like, I'm so used to like dispensing advice and like, especially, you know, help my kids out and whatever. And like, I was dumbfounded. I was like, what am I supposed to say here?
Because. I don't know that my kids are supposed to follow in my footsteps or you yours, right?
Speaker 3: Right. And
Speaker 2: I, and I started thinking about it, I'm like, I'm gonna have to give that some thought. And so, you know, so here we are wondering whether it's even a good idea to bring people through, you know, what we've done, particularly our kids.
Speaker: You know, I, I think of it in, in, in the same way that we talk about fundraising, right? Which is that like, when you raise funds, it does help you get to a particular outcome, but it also cuts off a lot of other options, right? You no longer can do all these other things. And so for me, I think the, the thing that I'm always trying to instill in the kids is exploration of all sorts and just keeping the optionality open, right?
So the, the, the bootstrap path, right? So how do you bootstrap your career? How do you bootstrap the rest of your life? And [00:03:00] I think that's really important for me that they, they keep those options open. I had a similar, similar moment. Uh, we were in Madrid over the summer and we had fallen in love with this little coffee shop cafe across the street, really sweet, young owner.
And she was super nice to the kids and they were constantly making her gifts and she was giving them stuff. And like, she knew her names, all that stuff, like just charming little, you know, uh, European cafe feel. And at some point. We start talking just about, about business and startups and like what we're doing.
And I mentioned that I had built a cafe at one point in my life that I needed a break from technology. It was like, I just wanted to do something that really, really short satisfaction cycles, just make people happy and enjoy my time for a couple of years. And so we started talking about that. And then as, as we walked away, Hannah, my oldest, uh, 12 year old, she said, you know, I'd love for that to be my first job.
And I said, what? She's like, I'd love to go work for her as, as my first job. And I was like, Oh, okay, cool. Why? And she said, he's like, well, look, I love the idea of, of being an entrepreneur like you are. [00:04:00] Um, but I also want to work for some other people and learn. She's like, I think I would really enjoy the job.
I was like, I'd be great. I think it'd be great. I'd really enjoy like the interaction with the people and, and all the things you told me about why you loved your cafe. She's like, but it would also show me like at a different level than you're at, what it would be like to kind of start and do my own thing.
And I was like, Oh damn, that's, that's better advice than I would have given you if you'd asked me.
Speaker 2: That's what I get. So go ahead.
Speaker: Yeah, go ahead.
Speaker 2: So Summer almost said the exact same thing. She's like, uh, I really want to do my own thing, but I think I can get valuable experience by working somewhere else.
And I was like, you're damn right you can. The only way you'll ever learn how to lead is by being led. And I said that it teaches you so much. It teaches you generally what not to do.
Speaker: Yes. There's also that. Yeah. You will find out. It's got me right where we're talking about parenting day anyways, but it's, it's one of those things.
Like we, half of the things I know about parenting were the things that I didn't want to replicate that I saw my parents do. I'm not saying they screwed everything up. I'd say they did everything right. It was neither. It was a mix of both, but certainly like you look at those things where you're like, man, [00:05:00] I'd never want to do that with my kids.
And you try to avoid those behaviors, right? It's that is how we learn leadership for sure.
Speaker 2: And I remember every detail of that experience. Now, mind you, I've been my own boss since I was 19, right? I haven't had a boss since. But I had five different bosses. Up until that point, I also worked a lot of jobs.
And I remember every single detail about how I felt, how I was treated, where I felt like I was capped versus where I felt I was, you know, underemployed, things like that. And I thought to myself, I'm like, okay, My daughter has an opportunity to avoid all of that bullshit. In other words, like, like being capped by her age or, you know, by her education or anything else like that.
I'm like the cool thing about being a founder, and this is where, you know, my mind just about to explode on it is you can do whatever you want. Like there are no limits, you know, our daughters, particularly summer and Hannah are freakishly smart. It's not like our kids can sort of throw a football so to speak and we thought maybe they should get into it Like our kids are like exceptional.
[00:06:00] I also saw that as like a heavier weight Because summer is so exceptional and like everybody says that about their kids. I mean my kid's got a 100 GPA like she literally has never gotten anything but an a plus in her entire life. Um, And all she cares about as far as if she does go career Is she only wants to go to harvard and she only wants to be a cardiologist?
How she that dead set at 12 years old. I know right? I mean she reads medical books for fun Which is crazy. And then she can be an entrepreneurial cardiologist, right? You know, so it's not worth it. Anyway, that actually created a lot more weight. In my response because I'm like if I deter her Ryan and if I say yes, you should go do a startup So to speak, you know nothing to do with cardiology nothing to do with medicine, right?
I'm like well shit. Did I just deprive the world of a great cardiologist or specifically selfishly myself?
Speaker: Standards, we're going to need those someday and probably sooner than later.
Speaker 2: I'm going to need those like probably sooner than later. Anyway, what a lot of people don't see, [00:07:00] especially if they don't have kids in, you know, you and I only so recently fathers in the grand scheme of things is how weighty that decision of should you follow my path is.
Because we could thumb the scale either way, right?
Speaker: For sure. And you see it. I think, yeah, that's the big question, should you? I want to circle back to something first because I think it's, it's an interesting one to ponder a bit. And I think that's what today's about. And that's the, the notion of like these caps and limitations and, and, you know, like the, the pressures and pains of having the boss and being told you can't do this or being arbitrarily held back.
For me, you know, and I think this comes from, comes from the competitive spirit and nature that I have. I think that some of those experiences help to really galvanize. Thanks. Now that I'm saying it out loud, I don't know if that's good or bad. , right? Yeah. But like that did sort of set the thing where like, I don't wanna do this, I wanna push myself against that.
So then, then there's something to be said for that too. It's like, well, what if I had continued on that same path and gotten to a point where I was the one setting the limitations, but in the corporate environment instead of, right. You taking that, taking the founder path. But I'm just wondering like [00:08:00] how different would that have been?
Right? Like had you not had some of those negative and limiting. Experiences. Do you think that would have changed your desire to be a founder or would it made you a better or worse founder?
Speaker 2: Well, let's build on that Because also, I think it's the person, the archetype of the person, right? Me and Summer are very alike in a lot of ways and we're very different in a lot of ways.
We're very alike in that we both have the ability to learn something quickly and just get after it. Summer has so many hobbies and interests and she goes so deep on all of them, right? Oh man,
Speaker: I remember the last time I was up there talking to her about meditation and crystals.
Speaker 2: Yes, let's go.
Speaker: Let's go all the way.
Take me as far as you want down this rabbit hole. I, we will not hit bottom.
Speaker 2: Right. And so she wasn't like, you know, when she was 10, she wasn't like, Oh, crystals are interesting. She's like, mom, dad, I want to become a certified Reiki master. And Classes with all these other old ladies basically as a 10 year old, right?
Cause she wants the damn certificate, right?
Speaker: Yeah. Yeah. Those women had cats older than she was.
Speaker 2: [00:09:00] They really did. And so I look at that and the reason I bring this up is because. What defined me, let's say like in my high school years, like, you know, pre college, et cetera, was that I never had an opportunity to go all in on something I really cared about in a way that I was rewarded for.
I want to restate that. I never had the opportunity to go, like, play a sport, so to speak. Not literally a sport, but like, you know, something, a passion, pursue a passion, where I was given, like, straight A's in it. Like, I was a strong writer, but I didn't care about English. And that's, like, kind of all you had.
I didn't care about the assignments. So I didn't excel at it. I loved creating things, but I didn't like creating the things that were offered to me in high school. So I just didn't do it. Forced upon
Speaker: you, not just topic wise, but then the entire framework around it. It's one of the things I talk about a lot, right?
Because I had that period in which I was homeschooled between first and eighth grade before I decided to go to high school. It was one of the things that really stood out to me as I was able to contrast the differences later. And I [00:10:00] know probably not a fully fair comparison, but homeschool was a lot more like entrepreneurship and regulated school was very much more like a corporate environment.
And it was one of the things that I realized later was that I was Um, given the freedom to chase down things. I was super interested in and I was rewarded for it. I got both. And it was, it was really amazing. There was this time where I came like super nerdy at like, I don't know, 12 bacterial division and just the, the, the way bacteria could multiply so fast and how generations could pass all that.
We arranged a trip for me to go up to the stone lab up in Lake Erie and work with a couple of environmental biologists doing exactly that study. Right. And it was, it was such a rewarding experience. Let me go as far down that rabbit hole as I wanted. And did I have to give up a couple of other things along the way and like maybe not do as much as something else?
Yeah. Didn't matter because. That's what I was passionate about. That's what I wanted to learn about. And I certainly made up for those things later. And like, that is to me, that's, that's entrepreneurship, right? Chasing down a passion often with an opportunity cost for something else you could or should, or would have done, but, but getting the outcome that you want to [00:11:00] get to and being fully empowered to do so, right.
It's just a beautiful example.
Speaker 2: The thing is though, like I think for folks. That have the archetype where they perform best when the limits are taken off.
Speaker 3: Yeah.
Speaker 2: There's a whole bunch of folks, majority of folks really, that perform best when given constraints. When they say, this is when this is due, this is exactly what you need to get done.
And they're like, bam, bam, bam, I, you know, hopefully knock it out,
Speaker: right? Philosophical question now. Well, not, maybe not philosophical, but do you think that's because, do you think that's environmental or, or do you think that's, is that, is that, is that nurture or nature? Yeah. Do you think there are just, I mean, surely there's some that are, you know, there's some natural tendency towards that, but I feel like a lot of that is just the system you come up in, right?
You, you become comfortable in the environments you grew up in and when you're in an environment that's highly regulated, highly regimented, and there are rubrics to measure everything you're doing, you're going to feel comfortable staying in a position like that.
Speaker 2: When I went to college, the first reaction I had from college was, this is it, right?
Like, I mean, you weren't allowed to have that reaction, right? That was [00:12:00] very antithetical. It was like, no, this is this amazingly rewarding and enriching experience and you have to appreciate it and all these things. And it wasn't that I didn't appreciate it, I was like, am I literally paying someone to tell me to read a book?
Yep. That's kind of what it feels like, right? That's what it was. Like, like, the lectures were like barely 10 percent better than what I had just read it out of my book. Generally written by the same person.
Speaker: Yeah, exactly.
Speaker 2: The experience was lame. I'm like, dude, this makes no sense. It's a bad product. And I am paying a fortune.
To go read a book. And again, I'm sure there's plenty of people that are like, Oh, my college experience was totally different. I'm sure yours was, I'm not, this isn't everybody's. This was definitely mine though. It was boring as fuck.
Speaker: Yeah, mine was exciting, but that was because I was building a business at the same time.
Had nothing to do with the, the university experience, right? Uh, the, that was stuff I did when I wasn't running the company.
Speaker 2: And so like in college, like as soon as I got there, I was like, This is boring as hell to me. Now, again, it's not an indictment on college. I'm saying what it was for me. And so I was like, what can I do that [00:13:00] can like fire me up?
And never in a million years did I think I was going to start a business like back then, back in my day, it wasn't the thing that it is now. Right. And I stumbled into it. I happened to do it and it happened to become something. But the reason it stuck with me in defined me was because I had no constraints.
So when I think about giving that advice to summer, And I say, Hey, you are an extraordinary talent. The worst thing you can do is apply yourself in anything that constrains you. And that's a bit of nurture to remind her of that. When she, my, my, my daughter's a voracious reader, right? When she reads, she's like, Daddy, I'm picking this book because it's at this reading level, et cetera.
She's also a massive rule follower. And I was like, I was like, sweetheart, like you could just as soon read a college textbook. Yeah. Like you're, you're already smart enough. You're
Speaker: capable of it. Yeah.
Speaker 2: Yeah. She's like, well, yeah, but I'm only in seventh grade. I'm like, no, you're physically only in seventh grade.
Speaker: Yep.
Speaker 2: Right. Like you can read whatever you want. Like you, you've already mastered reading, but you got words [00:14:00] down. Right. And so when I think about like having her pursue entrepreneurship, it's with that idea that I had this extraordinary talent in my daughter and just taking the reins off. And I always tell my wife, I was like, the best thing we can do is stay the hell out of her way because she's that stallion.
Speaker: Stay out of her way. And I think my, my philosophy in this is like, I try to stay out of the way and I try to eliminate, hurdles that I think would be that are either unfair or would be something beyond her resources to do so herself. The challenge there has been to try to be completely unbiased about that.
And regardless of what the, what the thing, right. And it's hard, right. It's hard because you look at something like a paperback. If they're excited about something, right? Like if she, you know, when, when they came and they, they wanted to start playing soccer, which has been my lifelong sport, of course, like I wanted to break down any hurdles for them and I wanted to give them access to whatever they wanted and, and did so, you know, if when they came with things that I was slightly less excited about or weren't my area of expertise, I tried and I'm, I'm sure I wasn't fully [00:15:00] successful, but I tried to apply the same level of diligence and care there.
But I think to your point, And in most cases, I think probably in the beginning, I didn't do a good job of it. And I realized it was so important to do so, which was not to make it terribly obvious that I was out there knocking down walls or opening doors, because I think again, part of it is that, right?
Like I guess truly, if there is to be a path forward in entrepreneurship and to become founders of their own businesses, you and I both know nobody's opening those doors for you later. Nobody's knocking down walls for you later. And so, you know, the, the last thing I would want to do is create this very streamlined, low friction path towards in that direction and then have them get there and go, well, shit, this is really different now that, now that I don't have a blocker.
Exactly. Exactly. Now that all the tackles in the world are coming at me, what do I do? Right. So I think that's been the very hard to strike, um, but kind of constant balance that I'm trying to create.
Speaker 2: And I look at it right and I can't think of another passion that you could pursue or career, I guess, that you could pursue.
I mean, entrepreneurship isn't really a career. It's a [00:16:00] structure that leads to lots of careers, right? I can't think of anything that's more open ended and for an extraordinary person, more suited to that open ended task. And that was kind of where I was about to jump on to the high five festive. Your dad is so proud of you.
Let's go start a company right this second. Right?
Speaker: Yeah. I already formed an LLC for it's waiting. I've got Michelle company all set up go
Speaker 2: and then something happened I had this flash right before I was about to respond that was Hold on a sec. I kind of do this. I do do this for a living and it all sunshine and rainbows Yeah,
Speaker: I was like, yeah, hang on a second.
There there are more than rose colored lenses to look at this through You As you
Speaker 2: were describing it, the devil on my other shoulder is like, dude, are you really going to lead her into this hellscape? And I was like, Oh shit. I kind of forgot about that. And then I started to think about all of the things that we go through as founders.
Cause you know, Ryan, you and I are sitting and talking to founders all day, but we've also been through an extraordinary journey ourselves to get here. And I was like, Whoa, wait a minute. Is this really, it'd be the equivalent of being a [00:17:00] war veteran and saying, you know, serving your country is the most important thing you can do.
And look at the glory that comes with it. And then being like, Oh, wait a minute. Everybody in my platoon did, did get killed. So like maybe it didn't be like pushing someone so quickly into all this glory because it ain't all glory and that started to drive me the other direction. You know what I mean?
Speaker: Yeah. And again, it has to be approached with a very, very careful balance. I think the, the thing that I've tried to do, and it looked at, we look, the good news is we have a lot of practice with us because we talk to people who've already decided to become founders every day and we're helping to guide them through exactly these decisions.
Right. So some of the same things. And so one of the things I've started trying to do is when I have important discussions or interesting kind of like philosophical or emotional decisions with founders, I'll talk to the kids about it. And I've started trying to be as balanced as I can, right? Because sometimes, you know, as a dad, you know, we're biologically predisposed to protecting them from the world and it's easy to overshare the good stuff.
Like, Hey, this happened, this happened, this happened. High five here. High five there. High five here. High five there. I've started trying to be much more open about. [00:18:00] Both sides, not just my own experiences, but those of others, because I think that's the other important thing is that everything that I do is always going to be viewed as something a bit more magical than anything anybody else does, because I'm their father, right?
And that it carries more weight. And so rather than just, lean on my own experiences and stories. I'm trying to introduce a lot more. And I'll give you, I'll give you one that, uh, was, uh, something that happened last year that I talked to them about probably a couple months ago now, but it wasn't when it was still very fresh.
And I think that was important for me, but it was this, um, thing that happened. You remember when we were doing tons and tons and tons of one on one office hours, like 30, 40 a week.
Speaker 2: Yeah. And
Speaker: I, um, About three, four months into doing that, I started to get a little depressed and I couldn't figure out why same thing.
Couldn't figure out why. And I was like, I I'm like, you know, everything in life is good. Family's good. Love what we're doing with the company. Like everything feels okay. Right? Like what is going on? And then I started to think back to [00:19:00] like all those conversations I was having, I'd started to internalize.
All of the struggles of all these other founders. And at some point I was like, I'm going to have to back off this a little bit until I can figure out how to develop a healthy relationship with other people's problems and not carry their water for them when they don't need me to. Because I'm not really just carrying anxiety, which doesn't help at all.
And so I had to talk with them about that. About, you know, the collective nature of, you know, what a wonderful and amazing thing it is. And, and how excited I am to saddle up and do this every day. And the, the other side of it as well, which is like, there is a lot of, a lot of tough decisions, a lot of hard outcomes, a lot of failures, and so, you know, being able to recognize that and develop resilience around all that stuff's really important too.
So it's, I think again, it's about pitching a balance to them and not trying to make it look one way or the other, and just being as objective as I can and unbiased, which not my. I definitely do love entrepreneurship, so it's, so I've had to be careful not to do the opposite, which is like, I find myself like, have I been negative enough lately?
Have I?
Speaker 2: You know, [00:20:00] 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 a thousand times before you, which means the answer already exists. You may just not know it. But that's okay. 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. 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. Here's where it gets tricky because we live this all day long.
We talk about this a lot. Like we're not just reflecting, like when we do this podcast or, you know, when we help people, we do a workshop on startups. com, things like that. We're not just talking about our own experiences. We're talking about the experiences of thousands of other people.
Speaker: Thousands. Yep. That we talk
Speaker 2: to real time all day long.
And guess what? When people book time with us to talk to us or, you know, we have lunch or dinner or something like that, it's generally not a high five fest that people think it is. Like, I think [00:21:00] from the outside, people think, Oh my God, your job's like Shark Tank. Like people come to you with great ideas and you talk about how great they're going to be.
Sometimes, rarely.
Speaker: Most of the time they come to us with a giant stack of problems they need help solving, right?
Speaker 2: Exactly. If I were to like stack rank what I actually talk to most people about, most consistently, top of that would be my life is going horribly. Like forget the startup, right? My life is going horribly.
Like I'm going through divorce or I'm having some like knocked on drag out fight. My health is terrible. Like there's a reason this podcast is called startup therapy because 90 percent of what we do, maybe more is actually therapy. It's what people go to therapists for. It's hard to do that job. And if you care about it, you have empathy.
Speaker 3: I
Speaker 2: think that's what makes us good at our job. I think that the folks that we have at startups. com, the reason like we're particularly good at this at helping startups isn't because we're some geniuses or we're so successful or whatever. It's because we care. We're just very empathetic. All the [00:22:00] way. All the way, right?
To a fault. And I went through the same thing, like, as we started to ramp up all these one on one sessions with folks, and I was spending time in person, uh, you know, over Zoom, et cetera. I was like, damn, dude, I just went through, like, 50 people's, like, end of life problems this week.
Speaker: Big problems, right? It's not, it's not like catching up with that high school friend who wants to dump about the relationship.
Like, it's big stuff, right? We're trying to decide whether to wind this down or not, right? Like, I have to choose between my marriage and my startup, right? These are big, heavy questions. And like, uh, you know, both of us, we do, you carry it around, right? At least some residual of that. It hangs on you generally until I hear what the outcome was.
All right. So you end up carrying that stuff around.
Speaker 2: Usually by the time I get called in. Things have, have long since gotten too bad. I I'm the surgeon that gets called at the emergency room. I'm not the, the GP that comes in for a checkup. Right. Right. It's very, very true. Tell me about vitamins,
Speaker: Will. Yeah,
Speaker 2: we're past that.
So anyway, we have this really kind of jaded purview, if you will, of, of how [00:23:00] founder stuff goes. Now, part of that, you can say, no, that's actually how it goes. But that's my point. I'm like, okay, I kind of know how the sausage is made and it's pretty gross. Do I really want to drag my kids? Into that same thing because here's the problem from my kids perspective What they've seen up until now is the good part.
They've seen the super bowl win They haven't seen what it took to get there They haven't like, you know, my daughter's 12 as as his years like they haven't been around for the parts where we never came home Thank you. That's sort of the point. Yeah, luckily we
Speaker: had that fixed before before their arrival More or less
Speaker 2: they didn't see the part where I was Essentially bankrupt and starving, you know, for years and years and years and years, right?
Like they didn't see that. So the way they see it is like, Oh, entrepreneurship means you get to live in a big house and go to private school. Exactly. Sometimes, right? Sometimes, but generally, no, that, that, that's not the outcome. I was saying, so, you know, they've never been there through that tough part.
They've only seen the part at the end. So the challenge with that [00:24:00] is if I'm saying, Hey, you should get into entrepreneurship, I almost feel like I'm selling them the wrong product, right? Like I'm selling them the upside of, of how awesome it is. It reminds me of when people say, Oh, you should become a doctor.
And like, they forget to mention the fact that you're going to be in school for half of your life and be in debt for the rest of your life, right? Like they kind of probably should have mentioned that one. Or the incredible rate of depression that comes with being someone who takes care of people all day, right?
I
Speaker: can speak to this one first hand, and actually this is where a lot of those lessons, so as I said before, right? You're not going to repeat those things that your parents said. My dad took path B, right? Which was to staunchly, and fervently turn me away from following in his footsteps as a physician and a surgeon.
And right, like to the point where he was like, yeah, cool. Uh, yeah, go pre med if you want to, uh, expect zero support from us if you do. All right. Like he was that, he was that against it. Right. And he, you know, bear in mind, like he started, medicine in like what I think was probably a golden age of medicine where money was good.
The care was becoming [00:25:00] amazing. The technologies were awesome. And then enter HMOs, PPOs, managed care, insurance companies, all that in group practice. And it just went to hell in a handbasket. And he was like, look, you want to do medicine for all the right reasons. You want to heal people. He's like, they don't let you do that anymore.
Right. So you're, you're going to hate it. And so he talked me out of it. Successfully twice and then the third time I talked myself out of it. And so so here we are
Speaker 2: But but that's that's sort of the point though Like on the one hand I see a lot of parents and I don't begrudge you for parenting every parents their own way I'm just saying this is my perception of it I see a lot of parents basically try to copy and paste what they did on to get to me is dangerous Because it makes a giant assumption that I just don't think is true, which is yes.
This kid has my DNA that makes them the same person. No, it doesn't. They have totally different experiences. And by the way,
Speaker: unless you're Ken Griffey. Yeah. Okay. Then it works. Then do that.
Speaker 2: Yeah. One, one case. Um, but like, you know, I look at it and I'm like, yeah, you know, my kids share a lot of my traits, good and bad, but there are other people, they're not [00:26:00] me.
And so this is where I take it back. My experience in my journey. It was my journey, right? Like entrepreneurship made sense for me because I was a super poor kid that needed a way to be able to do something that had no constraints, right? So it checked a lot of boxes that I didn't even know I had.
Speaker: Yeah.
You pointed that asymmetry, right? Doesn't matter where I started. I finished where I decide I want to
Speaker 2: finish. And I look at it and I say, okay, I could dissuade her. I could say, Hey, you know, honestly, like, yeah, things worked out okay for dad, like, in the end. But if I'm being honest, like, it could have gone the other direction.
I spend most of my time with the other direction and folks that are in that. And honestly, I think, I think it'd be something you'd probably want to avoid. And, and I think that would be worthy advice. I wouldn't be untrue, but I didn't feel good about giving that either. How about you?
Speaker: Yeah. You know, it's, I'm actually trying not to give advice at all.
I'm trying to just give perspective and, and to let them have as, as realistic a look almost as if I'm treating it as if they're shadowing me, right. In some ways, right. Where, where they're not actively shadowing me, [00:27:00] but they're around me enough that just through osmosis, they can kind of pick up on, on what I'm doing, the good and the bad.
I think. The thing I'm trying to do where like, I definitely don't want to do the thing where my father discouraged me from, from doing something. I definitely don't want to go the other direction completely. And I am encouraging them. I'm encouraging them in a very specific way, which is when they're interested or passionate about something, I want them to, to chase it.
What I'm specifically trying not to do, and it's difficult because I'm sure you do the same thing. Every time I see like a passion or something, like somebody actually has a passion. I immediately start to have ideas around how they could, they turn that into a business. Right? It's, it's impossible. Right?
I can't go on vacation somewhere without sitting down and being like, Hmm, here'd be a different way to monetize this. Right? Like ached in my DNA at this point, it's what I've become. And so I'm trying to help them explore the passions without saying things like, no, imagine if you could do this as a career, imagine if you could get paid to do this.
Right? Like, and I have done that in the past. I have stopped myself. I've stopped trying to turn everything that they think about or do into some financial outcome for them. I can think it. I can think it. I can hope that they end up doing [00:28:00] something. And I look, it comes from the right place. It comes from a place where we want our kids to be able to do something extremely meaningful in their lives without any limitations that fills their cup in all the ways, right?
Of course we do. I realized I don't need to view every single thing they do through that lens. I Not good for me and sure as hell won't be good for them, especially if I start, you know, letting that spill out of my cup and into theirs.
Speaker 2: And what's interesting about that is like, I looked at it and I was like, man, and you know this as well.
I could thumb the scale on this one. Oh, a hundred
Speaker 4: percent.
Speaker 2: I could absolutely like put a tremendous amount of deliberate encouragement into go start businesses, et cetera. You know, and to be honest, I quite specifically don't in our house. Right. Like my kids love startups. com. In other words, they love the idea that daddy works at a company that they all have lifetime
Speaker: memberships,
Speaker 2: but I love that.
Like, I love the fact that they love entrepreneurship. Like both of my kids have started businesses on their own, you know, without my help. And I think it's awesome, but I'm not pushing it in any way. And people go, well, maybe you are in deliberately if I am. So, [00:29:00] so be it, but here's the bigger thing. I don't want my kid's life decisions to be my decision.
I think that robs them of their agency. And I think it's, it's just straight up inauthentic. So a lot of times you'll see, uh, you know, the most traditional version of this is, Hey, son, daughter takes over business, you know, after dad started. And there's nothing wrong with that. I'm not knocking it, but I'm also saying like, was that really their dream?
Was there a dream? To make whatever the fuck you made. It's not that they couldn't want to do it. And again, I'm not knocking. I've seen great cases of it. But I feel like if I force them into that channel just because I believe in it, I'm robbing them of their own path. And I find that to be very unsettling.
And I look at it and I say, okay, my son, Will, my daughter, Summer, whatever they want to do, my job is to help, you know, like you said, like shed light on, on opportunities, but then get out of the way,
Speaker: get out of the way.
Speaker 2: Like that's your life. Not mine.
Speaker: Go back to something else that we said at the very beginning, which is that they're incredibly intelligent, incredibly capable kids with a lot of resource behind them.
Speaker 3: Right.
Speaker: And so [00:30:00] at some point, like, I also think I am 100 percent sure in my case that I'm thinking about this far more than I even need to. Okay. Because I do trust them to make their own decisions. And, and what I'm trying to really do, here's who I actually want to raise. I want to raise a kid who's so self assured and so self empowered and so, so understanding of themselves, that whether I pushed them towards entrepreneurship or told them never to do it in their lives, That they would still make a completely objective decision about that regardless of what I do.
So I think that really the best thing I can do is eliminate myself as a variable in that by just empowering them in all the ways, right? It's going to have less, it should have less to do with what I tell them or how I approach it. Then how I helped them to cultivate being the type of people who can make their own decisions and feel good about that.
Right. Not feel like, Oh, I should do this because that's what I think dad would want. Or I should do this because that provided us the lifestyle that we had. And we'd like that too. Right. To know that like, there are a lot of ways to skin that cat. I'm not sure why we still use that phrase. [00:31:00] I hope we don't skin cats anymore.
Speaker 2: That is the most bizarre phrase ever, but we're not going to end up that. A few months ago, we're having a conversation, me and my wife and my daughter, about what my daughter wanted to do. It actually doesn't come up that often, it just happened to come up. And my wife said something like, you know, find something that makes you feel financially secure so you can do the things that you want to do.
Summer, who, you know, is smart beyond her years, just looked at her and said, Mommy, that's not what's most important to me. And my wife was like, trying to be supportive, but she's like, Yeah, but
Speaker 3: yeah,
Speaker 2: sweetheart. Like, you know, you got to find something that can support you. She's like, first off, mom, the decision about what I'm going to do is my decision and no one else's.
And she didn't say it defiantly. Like, no, no, no. Just matter of fact, very matter of fact. I know this. I know this to be true and she's
Speaker: right
Speaker 2: and she's right that's the worst part where like my wife couldn't push back and she's like I don't want to do anything that that sacrifices my well being and I was like okay here we go and I said look I get that please you know don't put your well being before anything else like that yeah but doing extraordinary things has some well being cost to it in some ways I get that she's like like I [00:32:00] I do things far above and beyond what I'm required to do now which is why she has like the GPA she has she does but I do it because I want it and I do it with respect to my well being.
First off, what 12 year old talks like this, right? Like I'm just getting that perspective at frigging 50, right? What happened here? Which
Speaker: again, great reminder that they'll probably figure this out better and faster than we will. So we don't even need to have this podcast. Well, I think, I think that's it, right?
I know. But it
Speaker 2: was moments like that where I'm like, No, I pretty much need to get out of the way. Imagine for as much as you and I spend our entire days helping people, helping founders, et cetera, like helping them through things. The big difference is they came to us and asked for that help. We didn't show up in their living room and start telling them what to do.
Right.
Speaker: Yeah. Yeah. We're not their older roommates who pay for their food.
Speaker 2: Yeah. And so I guess, you know, I looked at it and I was like, damn, dude, it's hard for me to wrap my head around this again, given the scope of what we do, Ryan. But I was like, It's not my place to tell her what to do. She was looking for my response, my [00:33:00] validation, like my understanding.
In the end, I was like, I'll support whatever you want to do, but I'll never try to make a decision for you in her face. It was so cool to see, and I have to mention this cause you and I talked about this yesterday. For all these podcasts, you know, uh, we write an article about it and then we can kind of talk about it.
And so, I drafted the article for this episode and I texted it to Summer, uh, when she was driving home from school yesterday and she wrote me back, I'm just reading it now, it says, Daddy, that is perhaps one of the most moving writing pieces I have ever heard. You couldn't have done better. And I was like, this girl, like,
Speaker: I was like,
Speaker 2: oh my god, this is the best thing ever.
I love her to death. And it's really interesting to me, like, now that our daughters specifically, our oldest daughters, are of age, where we can start to have that dialogue. And I guess here's where it comes down, Ryan. We have some consequence, right? In these discussions. For the first time, right? You start
Speaker: to really feel it.
Yeah. I mean, I'd argue there was probably consequence all the way back, but like it's the point at which the consequence will manifest is so much closer now. Because they are, they're at the [00:34:00] age now where they're starting to, they're starting to not necessarily truly like write decisions in stone, but they're starting to make decisions or they're starting to test decision making.
If I don't become a self employed, I'm going to become a cardiologist who graduated from Harvard, right? Now, that's not a decision that will necessarily, you know, come to be, but it's a decision, right? She's making decisions. They are starting to make decisions around what they want to do with themselves.
And that starts to dictate a lot, a lot of actions. This is a really, really important point where like, if you go, Oh, you know, Harvard, that's for, uh, that's for blue bloods or, Oh, you know, becoming a cardiologist. Yeah. It's, it's all going to be done by machines the next 10 years. Why would you do that?
Right. Right. Right. Like That can have all of a sudden, it's like, Oh, well, I hadn't thought of that because I didn't need to yet. Cause I'm 12, but now I will. And so, yeah, you're, you're absolutely right. We're at a point now where I think unlike, you know, the early conversations, having these early philosophical conversation, there's six, seven, eight, nine.
It's a bit like steering the Titanic. Yes. There will probably be some course changes as a result of this. It's going to be so far off that we don't see it. The [00:35:00] discussions we're having now are steering speed boats, right? Yeah, there's a, there's often a very immediate change in behavior and direction based on that.
Speaker 2: And so, so here's what I would say. I haven't given all this thought, Ryan, right? All this thought and all this consideration and in staring my daughter in the eyes, you know, someone that I just love so deeply and knowing it's your own kid makes it so much harder to have this conversation. But here's essentially what I told her.
I left her with this. I said, I talked to founders all day long and I, and I always give them essentially the same disclaimer with my advice. I say my job isn't to tell you what to do, right? Your job is to decide what to do. My job is to give you the benefit of my experience in some new tools in your tool belt.
So you can choose if you want to use them or how you use them to make your own decisions. And I think when we're talking about how we want to raise our kids, we want to talk about how we want to raise this generation of founders. We're not going to raise a generation of founders by telling them what to do.
We're going to raise a generation of founders by giving them the tools and letting them go build what exactly what they want to [00:36:00] build with their future, not ours.
Speaker 4: 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 bootstrap 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.