Can I Hand Off My Startup?

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, I think there's this dream scenario where we build a startup and we get it cranking. You know, it, it achieves some level of escape velocity. And then we can just bring in somebody else, hire a killer operator and, and, and sit margaritas while the money multiplies. Right? So from what I hear, handing off a startup is pretty easy for about 48 hours. And then after that, entropy starts filing status reports. You've, you've done this before though, man.

So like, walk me through how well or not well did this go? It always breaks, like kind of for the same reason, but the problem is. It doesn't break right away, so it looks something like this. Uhhuh. Okay, I'll rewind back. Let's, let's go back like this is, I, I, I've tried this a few times, but I'm gonna cite one specific example.

In the early, early days of startups.com, long before it was startups.com, this is like 2000. Two, 2004. Mm-hmm. We're going way back in the way back machine. Yep. I had started building all of these companies that were all like doing pretty well. Like, you know, one of 'em was swap lease.com and it was making you millions of dollars and you know, whatever. And so I'm building all these companies like biz plan.com, which is, you know, what we have today.

Yep. And my idea was, and it wasn't a bad idea in theory, and I want everybody to hear that. 'cause the theory is the problem. The idea was I'm gonna build these businesses, I'm gonna invest my own cash and I'm gonna get 'em told they're EBIT positive and have a substantive way to keep growing. Okay? Sure. So swap a lease. And for those of you that aren't familiar, I think the company's still around them.

Nothing to do with it anymore, but a lot of you to get in and out of car lease, it's basically, uh uh, transfer your lease to someone else, not literally swap cars. So that got to, I'm trying to remember, this is a long time ago, but that got to like $3 million in revenue, let's say in Ryan, maybe 1,000,005 in ebit. Yep. Makes sense. In like pretty short order.

Yep. And then the next business I did right thereafter, like a year later, had the same trajectory and I was like, okay, well this is, this is at the beginning, right? Yeah. You know, so taking that much now I just need to keep starting as many of these things as I can. And that's where it started to fall apart.

But the, the other part of it was, all I need to do, my value is I'm idea guy. This is like the, the dumbest thing, right? I'm Idea Guy and I just go in, I get it started, I bring the idea together and I let it run. I go start the next one and everyone will just keep. Piling cash on me. Everybody's idea of the startup dream right there. Right. You, you just nailed it, right?

Yeah. Would just, would the idea guy just why would work cocktail napkins hand 'em off and then somebody else turns 'em into cash. Perfect. And, and, and I thought it was an awesome situation for someone else too, because someone else has already figured this thing out. All they have to do is not fuck it up. Yep. Like that is your mandate. Just don't screw this up. Right. Everything's going fine. Right. Don't screw this up, but, but easier said than done.

As countless startups have proven, the second part was, okay, this here, here's my plan. I'm gonna keep starting another one of these companies like every 18 months. And the reason it's gonna work so well is I'm gonna put really ambitious founder style managers, CEOs in place of each of them. So each of them will have their own like quarterback superstar. Right. Right. I mean, this sounded like a really good plan.

When I talk to business founders, you know, like startup founders and whatever, um, business owners, I was gonna say, a lot of them were like, look, I wanna get to the point where the business is working for me and I can go, you know, be the equivalent of sit on the beach and sit margaritas and have it just send you money. Yeah. The chief margarita officer, I never heard that. I love that. And I tell 'em every time I said, it's an awesome dream. And like every dream you wake up at some point.

Yeah, it's what a nightmare you have on your hands.

So what I thought we could talk about in this, this episode is like really, really dig into why it doesn't work, why it sounds awesome. 'cause everybody has the same idea. I'm just gonna hire the super capable person and they're gonna run things even better than I did and blah, blah blah. Right? Like, and it like kind of never works. I'm sure there's some situations, there's someone that's gonna email us, make Oh, not true. I made it work. Yeah. And, and I always say like.

I get that someone did something differently. Like when we say you can't raise capital in 30 days, so is not true. I made it work. Yeah, someone did. Yeah, dude, I get it. Like you made it work, but we're talking to the 99.9995% of people, not you, sir. That, that's like Brad Pitt emailing me. Like, what do you mean you can't just go to LA and become a, a international uh, actor? I did. It worked for me. Yeah, red Pitt, you did it.

That's the point nobody else did anyway, so I thought today would be kind of fun. To talk about, like, like really kinda lay out why we all think this dream can exist. Like kind of what it looks like. Probably talk about why it won't work, right? Like, you know, kinda where it breaks, but, but more specific because I, I like to be tactical in how we give, you know, this advice. I would say let's, let's finish it off with what we can hand off.

Like, you know, what, what you actually can hand off and feel pretty good about it and what you can't, like, you could try guarantee, it's gonna blow up. Ryan. If, if we were to think about. Why this doesn't work? Like why wouldn't this work? Right.

I would say the first thing I would say is we fail to estimate entropy. Yeah. This, this, this concept that that's, everything's okay now. But chaos ensues. You know what I mean? I, I think that's a big part of it. I think that there are so many little things that we're doing as a founder that don't really like, they're, they're not in the job description. Right? Right. They're, they're not. Even if somebody asks you, what did you do today? You wouldn't even remember having done them.

That's a great way to put it. I didn't even think about that. There are hundreds of these things, right? There are just hundreds of these things that we just do nearly out of instinct. Having run that particular business, they just become muscle men, right? It's just, it just, right. It just happens. And so I think that the, the laundry list or laundry list of laundry lists that are those things. A big part of where the, the, the handoff starts to break down. Right. It starts to fail again.

Not for like one big reason. It's like, oh, we hired someone and they only speak Mandarin. Gosh, silly us. The team only speaks English. This isn't working for one big reason. Right. No, it's not that it's like. Thousands and thousands of little things that just go off the rails, one after another and not even off the rails to the point where like, you can even notice it. Right. It's, it's against a death by a thousand cuts. That's the interesting part, right?

Yep. Um, and it happens over such a long period of time. Yep. And so imperceptibly, but it happens at a moment where you're also not paying attention to what's happening anymore. Correct. Which, which is in, you said it a moment ago, I thought that was really interesting. A lot of things you don't even realize you're doing. Right. Like there's probably 20 things you and I will, will do this week@startups.com that we don't even realize that we're doing.

We just had a, a customer issue bubble up a few minutes ago before we got a yes. Got this recording. And you and I both know instinctively what to do about it. Yep. Right. Like we didn't even realize to discuss it. We both, we, we know exactly, but new person coming in that would otherwise do what we do has no history like we do. Right. We have the benefit of over a decade of dealing with this. Yes. Like we know all the outcomes. Like there, there's nothing new to be discovered here.

New person, even if they're experienced, doesn't have our experience. Doesn't have our experience. And, and I think part of it's like, it doesn't even get documented or handed off. The first time they see that is the first time they see that. Right. So it just, it just pops outta nowhere, catches 'em by surprise. And they go like, well, this wasn't in the job description. This wasn't when, like the, the, the stuff that you.

Talk me through, this isn't what you, you told me I was gonna need to have to do. And I think that's just because again, we are so used to doing this stuff, we just forget about it. Right. It doesn't go in the brochure, so to speak. So let me, let me set up my situation. 'cause I said I, I've been through this a couple of times. Yep.

The first time was with the agency, and I've talked about this in previous episodes where I tried to like. Fire myself at least three times and it never took, yep. I kept getting dragged back. But I wanna talk about time after that. And it's kind of what I set up a moment ago where I was talking a little bit more about, uh, having, wanting to run all these different companies.

And so we get a company that essentially became bizplan, et cetera, and we, we get that up and running and that's, that's doing, again, I'm trying to remember, this is like 20 years ago, but let's say it's doing somewhere between. Two and a half to $3 million on about a million to 1,000,005 in net income. Okay? Yep. So, so again, let's, let's just round it and say 3 million in gross, 1,000,005 in net.

Okay. And we got to that point, I wanna say in less than 24 months, which for a self-funded startup is awesome. Is awesome. Yeah. And that's real money. I, I don't care who you are and how big time you want to get with it. Million five net to the founder is a lot of frigging money. Yeah, right. It's good money. So my thought is, you know, what's cooler than 1,000,005, five businesses that are throwing off 1,000,005? Yeah. Right?

And, and so my journey to the bottom of the ocean began, it's, so here's what happened. I, I just wanna lay this out because I, I want folks to hear this isn't theory. This is me saying, here's what happened. And I've watched this happen so many other times. Here's my thought process. My thought process was this isn't that hard. Okay. We have a business that is very straightforward. It's basically a SaaS model, uh, company. There's no service layer whatsoever.

We don't even know who our customers are. I mean, like, other than going into analytics or looking at their account, we'll never meet them. Okay? Like totally blinded. All you have to do this is back in the day, you can appreciate this as the c uh, CMO. All you had to do is feed the AdWords engine. And if you fed the AdWords engine in 2004, uh, it would spit back money. Right? It would, I mean, like it would just puke money all over you. It, it was, it was a beautiful thing.

I was also new like what is Yes. The dawn of pay per click, right? The dawn of pay per click. Yeah. I forget about that. Incredible. So, so I go out. I hire a very good CEO, okay? Mm-hmm. It's a guy, uh, both of you know, we played hockey at his house and, uh, he's just a great guy. He's a CEO of, he's been CEO of multiple, uh, internet companies, and he's, he's a dear old friend and he is awesome. So I, I wanna start by saying he'll probably hear this episode, or I'm gonna mention it to him.

The point of this isn't that he did something wrong. The point is he was really good. And it didn't work, right? Yeah, it didn't work. And so I'm saying this wasn't, this isn't a, I made a bad hire, it wasn't a selection issue. Yeah, yeah. No, that's my point. That's what makes it worse, right? Yep. So here's what happens. This is when I was leaving Columbus Ryan and, and I'm gonna go to Los Angeles, started another company. It was afford it, right?

And, uh, I'm like, listen, and I just started a company before that got cast, which is what brought me to, um, LA. So I get there and I'm like, and I, and I, I tell the c, the new CEOI said, Hey man, you know, just keep doing your thing. You've got, you know, full, uh, control of this thing. I'm gonna be as hands off as possible. And Ryan, I was beyond hands off. Like I, I was like, didn't even know what was going on. Right. Yeah. I think that's the, that's a challenge, man.

It's a handoff, not a hands off. Right. I think there's a very important put distinction there, man. Yeah, yeah. Because like, you can hand it off. Um, but I think the minute you go truly hands off, you're gonna run into trouble. Right. Because it's, look, and it's, it's the difference between founder supervision and supervision, as you said. This guy's talented. He's done this multiple times. He's done it. He, he had done it before. He's done it since. He just didn't do it this time. Why?

Because it's not the same thing. Right? Founder supervision is different than just supervision. And I think that, and to your point before it happens over that period of time, and it's not like this massive implosion. It's an erosion, right? And, and little misses start to compound when you're truly hands off. Right? And I think a, a big part of that is, it's funny 'cause when we go back and look at it, and I'm sure you can do this now. You see those things. You can see those things.

You go, oh well yeah, all the warning signs were there. But I wasn't. And, and the person that took the helm didn't know the warning signs. Right. They, they hadn't seen the canary die in the coal mine, so, right. They had no idea what this stuff meant. And I think that's really where this, this begins to go wrong and why it's so funnily and, uh, kind of obviously avoidable.

Win the founders in the seat like these, the, the same erosion that happens to someone else does not happen to the founder. Now, this isn't to say that founders can't fuck up startups. We do it all the time. We're good at it. Right? But we do it differently. Let me walk through kind of what happens. Sure. So, lots of fanfare. We bring in new person, which always happens. Yep. You know, you want, you know, hype that person up. Talk about what, what a great handoff is.

They wanna say, you know, how you've done this amazing job of leading the company. It's, it's almost like this carbon copy, uh, template that everybody uses. So I'm like, oh man, I'm free to go do other stuff. And I, I was already committed to all these other companies anyway. And so here's what happens. I move, so I'm across the country, whereas before I was there every day. Okay. But now I move from, from Columbus, Ohio to Los Angeles. Now I'm not around anymore.

I'm, I'm like physically just not around. Whereas before we were all in the same office and little things happen. Okay? Now I'm not being specific to, to this company. I just want to, uh, generalize a little bit. Little things happen. Example, customer has a blowup and it's just not handled in quite the same way, okay? Right by itself. Not, not the end of the world. Okay. A not great hire. Okay. So it's, it's, you know, you know, um, you know, what's the issue with hiring?

It's a's hire A's, but B's hire C's and C's, higher D's kind of thing, right? Like, if, if, if you don't get good people, well. A person gets hired, that's like a C. Okay. And then all of a sudden that sets the bar for other people hiring that are C because they don't have that same intensity. Or maybe in some cases you, I'm not saying it here, but like charisma to be able to pull in the, that A level talent and all of a sudden talent starts to degrade, but it happens over a slow period of time.

Right. The other is. Just, you know, um, that urgency or freakishness, and we'll talk more about this as, as we get into this, just isn't quite there. Sure. And, and overall, I think the best analogy I can use is Ryan, given that we're both parents, it's the equivalent of if we left our kids alone, fend for themselves. Right. Fridge is stocked with food. Right. Lately everything is fine. Okay. For some period of time, nothing would go wrong. Right? Nothing would go wrong. Absolutely fine.

And we were like, what have we been stressing about this entire time? But then someone's gonna spill a can of soda, someone's gonna back up a toilet, someone's gonna not mow the lawn. Right? Just stuff we would've paid attention to. Okay? And as every moment of entropy expands as problems, beget problems, we come back to a house that is trashed, trashed. We're like, it was going fine. What the hell happened?

Were there any signs, like were there any specific spilled soda moments that you saw at the time but ignored? Because I wanted, I wanted like more of an emotional reaction here. It was like, yeah, I saw this thing happen, but I was so happy to not have to deal with it, or I was so glad that it was something else, or like, or I just felt like it wasn't that big of a deal. Were there any of those moments that, like you saw that then, like in hindsight was like, yeah, that was.

Probably cost me a fortune while I was hands off. Uh, in most regards, I was still the financial person. I was still the CFO Uhhuh, so I'm watching our numbers and they in shorter, they stopped growing, but they start dropping a little bit. Okay. Then I'm watching our customer complaints. That that was it. I'm watching our customer com Customer complaints grow because our product was starting to suck, right? But our team was just milking what it was.

Instead of improving the product, they just like. How we dealt with complaints, right? Yep. Which is not the same thing. And I was like, ah, damn dude. Well if you just deal with the complaints, I'm sure like it'll fix itself. But here's the thing, Ryan, no one was, was sitting down saying, we need to restart this whole thing and, you know, prevent improve the products so that problems are happening. Mm-hmm. Yeah. Yeah. Everyone was like, oh, the problem is that there's problems.

Do you see what I'm saying? We'll just get, we'll just get really good at tackling people who have problems instead of tackling problems. We need more. Customer support, not more product innovation. Yeah. Right. Yeah, yeah, yeah. And, and that's the kind of thing where little by little, with every day that goes by, that you don't improve the product. You double down on the problems, right? Yep, a hundred percent.

And if your mandate, let's say, as the CE, who's been handed the keys to this thing is just keeps sending checks. Think about this, man. You can keep sending checks for quite a long time for something that's fundamentally falling the fuck apart. That's where I'm so distracted. I'm like, are the checks coming? Yes, I'm good. Move forward. Okay. But I'm not around anymore to really pay attention to what's happening.

So, so was it the case, like when you saw the numbers start to drop and the complaints rise, uh, did you ever consider stepping back in at that point? Or did you just hope the team would course correct? Or was it even more like, just sort of head in sand?

Here's the problem. It happens so slowly. That I, there was nothing to react to. Right. Uhhuh. Imagine this, imagine this, uh, imagine you're doing say $200,000 a month in revenue and that 200,000 goes to 198. Yeah. Not really like, you know, burn the house down. No. Yeah. We not, I'm not, nobody's ringing a bell and screaming about it. Yeah. Exactly. And, but the next month it goes down to 1 97. And again, it's still a big number and your net income number is still huge.

And like, so like overall you're like, huh, you know, like good month, bad month, you know, maybe it was a bad quarter, you know, whatever. You will change our Google marketing, you know, whatever. But here's what happens. And as A-C-A-C-F-O for a long time, I can appreciate this. You lose the memory of what your baseline was. So for example, let's say you started at 200 KA month in MRRA year from now.

You're now at 168, but the problem is you dropped by like a thousand, 2000, 5,000, whatever throughout the course of the year. Yep. By the start of the next year, you sort of forgot that you used to be at 200 K. Yeah, yeah, yeah. Now I can say it's the boiled frog challenge. Yep. It's exactly it. That's exactly it. And so it never gives you this holy shit moment to jump out of your seat and fire alarm, you know, into this thing, and that's how it breaks.

Doesn't break because one major thing happened. I might, right? Yeah. It breaks because all these little things happen. It spilled cans of soda, the un unloaded lawn, and you weren't around to correct for it. Yeah. And because you were so, next thing you know, you got a business up on blocks in your front yard, which just happened. Well, that's kind of what happened. Okay. Yeah. So, so, you know, uh, let me, let me fast forward to that.

So years go by, this isn't like a couple months or whatever this is. Years go by and I fly back to Columbus and I'm meeting with the team, and the team is fully checked out at this point. I I, I bet if they were all on the podcast right now, again, a great group people, they'd be like, yeah, we were pretty checked out. But yeah. Yeah. At that point we're like, Will's gone. We just send him checks. That doesn't feel that great and fuck this, I'm not gonna do any more work than I have to. Right.

And frankly. I get it. I get it. Yeah. I didn't get it at the time. I get it now. So I come back and we're doing like a little strategy session for how things are going, which I rarely did at this point. I'm like three years removed by this point, Ryan, and I remember sit down with him and I said, Hey, let's go over the strategy for next year. And they're like, what do you mean? And I was like, what do you mean? What do I mean?

It's like we just keep doing the same thing and you just keep ignoring us and that's it. Right? Yeah. Pretty much. Right. And I was like, and by the way, it's all my fault, all my fault. I, I, I, I take full responsibility, but never saw it coming and Yeah. Yeah. Uh, remember toward the end of this is when you showed up.

This is, you know, before we had started what, what is now startups.com and so you saw some of the ghoulish stuff we had going on. 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 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 dayLong@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.

I remember thinking at some point, what was it? The, let me encapsulate the thought. It was like, uh, when the room smiles, but the numbers frown. Believe the numbers. Believe the numbers, right? Like, yeah. Because there, there was this sense that everything was fine and right. And like, and it was like, yeah. Oh, you know, we're just, we're just doing what we need to be doing.

Yeah. It was, uh, yeah, it was a sense that there was this sort of a disconnect between like the, the attitudes and the actions and, and like the, the outcomes that were actually happening.

And I think it's one of those things that you, you do realize at some point, which is that founder mode has become a meme. And, and look, I think it's a little overblown. Yeah. Founder mode isn't a meme, it's also doesn't have to be like a full-time lifestyle. I, I think it's become too overblown, but it is a metabolic rate. It's how we process things, right?

Like a, a founder is going to digest information and energy and do something with it at a different rate than someone else who comes in, right? And again, we both have a lot of respect for this individual. We both know him. So this isn't about the, the, that person's capability, but the way they think, feel, and operate within that business is entirely different. All right.

And look, on one end of the spectrum, you could hire somebody, not, not this individual, like hire somebody that's just like, they go full apathy. But let's just say that whoever you hire, I don't care who they are, whoever you hire, they're gonna be closer to apathy than you as the founder were. They may be really close to where you are, but they're gonna be at least some degrees closer to that than, than, than you are because the costs are totally different, right?

The stakes are completely different for that individual, and you can't ignore that babysitter and a parent. Yeah, right, exactly. A babysitter's concerned, a parent's entire life is wrapped, you know, wrapped into the outcome.

I, I remember, like, I'm, I'm fast forwarding to around that time, this is like circa maybe 2011. I'm not always great with my dates, but 2011, uh, we're wrapping up. One of the companies that I had, I had started called unsubscribe.com and we were selling it off to, uh, to trusted id and, uh, Jamie Siminoff, who is my co-founder, who, you know, started Ring the doorbell company after that, and Jamie sat down with me. I'll never forget what he said to me. He said, I'll never do this again.

I was like, what do you mean? He said, this was your idea, the unsubscribed idea. He said, and I basically went all in on someone else's idea. Yeah. And it never felt like mine. I never, um, I, I never felt like the, the ownership, et cetera. And it, and it felt like I was taking care of somebody else's kid. And I mean, to, to Jamie's credit, he is very honest about it. Right. And, and self-aware. Um, yeah. Great lesson for him. Great lesson for him and, and I thought that's really interesting.

I mean, we co-founded the company together. Our names are on the incorporation documents. Right. But he felt it wasn't his. Right. Sure. He felt it was a cool idea that Will had, so let's go, let's go do it together. Yeah, yeah, yeah. But it wasn't like we. Both were at a bar one night and it just, like, the conversation sparked. So, so stick with that for a second because, because I think a lot of folks are, are gonna need to hear this twice. So that was somebody who started as a co-founder?

Yeah, a co-founder. Great point. Right? And they didn't feel like they had the ownership. Right. Now they clearly like the, you know, financial ownership. Yes. But idea and passion, ownership. No. And so if you can't create it at that level. We have to recognize that anybody we bring in to transfer to a new leader, if they didn't originate that idea, it's gonna be some even lower version of, of that level of feeling of ownership for that individual, right? We have to act accordingly.

Most people work for a company who, who wasn't their idea. Right. I mean, like 99% of people, right. So I say that to say, but founders feel a lot differently about this. Right? And, and Jamie, who I, uh, he had started like six companies before that definitely, you know, knew what that feeling was like of being able to kinda like, you know, sell your own thing and notably felt. Not being able to sell something Right. That that was, that was truly, that he felt passionate about.

And I, I get that. I get that. And so, so what I would say there though is, um, there's this really interesting thing where we have to recognize when we're handing something off that who we're handing it to ain't us. And I, I tell you what. I think there's a, there's an opposite argument that people try to make. Like, that's the point, man, I'm not a great CEO, I wasn't cut out for this.

I wanna find somebody who was built for this, that is a career, CEO, you know, you, you name it, has the credentials. I don't have and, and could put the energy I don't have into this. And I get that argument. Yep. And they're still not you. Right, exactly. That. Yeah. That, that, that makes them different. But that doesn't make them you right. Correct.

Correct. So let's talk about what you can hand off. Okay. Like, I, I don't wanna do this, like nothing can be done because you absolutely can and should hand off tons of stuff. So if you're okay with it, let's, let's start with the, what you can hand off and then let's get into what you can hand off. Like, just like danger will Robinson signals all over. Right, right, right, right, right. I think, I think you can very much hand off operational tasks like COO level tasks. What do you think?

I think so I, I think that that's, I mean, like I'm, I'm going through and like, I'm trying to think of why, why I said yes to that so easily and like where it might break. But I think that because by and large those things are, are, are highly documented. They're highly regimented. They're, they're operational, right? So they're, they're repetitive by nature. And so yeah, I think that the, the operational stuff can be to, to a degree. I think it does still come down to some things like.

This is what I'm wondering. I'm wondering if there's a paradox and a bit of a, of a trap here in that those feel easy to hand off from a structural standpoint. Again, like documentation, all that. I'm wondering though if, if that, if that puts us in that dangerous position there when something does go wrong, um, that the reactions are different, right? That yes, you can, you can put somebody into that rule to execute it.

Um, but I still feel like there's, there's always the risk that the, the reactions don't marry up. I remember early in my career I had hired a very competent COO, uh, and, and she went on to do amazing things. And I remember watching her in the room with, with the team, okay. And she's basically talking about, you know, what strategy is and what we're gonna do next. And, you know, all these things. Just like, you know, being a C-level person.

And I remember thinking she has great authority, she has great credibility, and she's got great communication and she's inspiring. No one. I, I just think about that for a second. Yeah. Yeah. She's a hundred percent competent. Competent, no issues there, but 0% as, you know, inspirational, aspirational, I dunno. Um, inspirational, let's say, and I thought to myself, huh? I didn't really see that coming. And lemme give you one more parallel.

Around the same time I hired, um, a, a director of sales who also went on, actually both these people went on to become very prominent CEOs and the director of sales, um, that I'd hired. I was watching him give the pitch. He's wildly professional, like very good, like pitch man, right? But I was like. But there's no soul in his pitch. Mm-hmm. His pitch is accurate. What he's saying is true, right. He's reading the room properly, he's getting emotional signals.

All the things you should do to work a room. Yep. Uh, when you son, good, good sales person. Correct. But it, it's like the difference between Tim Cook pitching and Steve Jobs pitching. Yeah. Yeah. There's just no magic. Yeah. Right. Yep.

And, and I realized when I got up there, the reason I had a certain level of charisma is because I had a belief in something, a religious level, belief in what we were doing. Yep. That it wasn't a job for me. It was a mission. And I think like when, when Tim Cook gets up there, I'm not knocking Tim Cook, I'm, he's phenomenal. This is kind of the point when Tim Cook gets up there, he explains what the new gadget's going to do, right? But it doesn't make you dream.

When Steve Jobs gets up there, by the time he's done, you don't even care if it works. Just like, like, damn seriously. Sign me up. What? You invented the MP three player that was made five years ago. Amazing. I want one. I can't believe I've never had one. Right? One. I can't wait. Yeah, yeah, yeah. And so, uh, so he, he had this, this charisma, but it, it, it really came from almost a religious level, fervor. Sure that he could deliver, that he can't hand off. That's my, he can't.

Yeah. Yeah. And like, and they've tried, right? They hire for IT companies this where they'll like try to bring in the pitch person and all that stuff. And it's just, and again, like they'll give a great pitch, but it is not the same thing because it comes from, it's the difference between seeing a beautiful sculpture, a piece of artwork versus seeing a masterclass done around building a home. Right? This is something you can appreciate right now, right? So like what an architect does.

Where it's very deliberate and very purposeful and very like specific, and it accomplishes everything that it needs to. Not that that's not beautiful, not that isn't amazing, but it gives you a different feeling, right? So when something is constructed in that way, sort of like as it should be, as opposed to how it could be or, or why it is, I think that's where that really just, it's irreplaceable. I I you, you don't see this after once founder led sales stop. That pitch does sort of die.

Yeah. That, that's what I'm saying. And, and, and I think there's, there's a, everybody here can appreciate this that's listening 'cause they're all founders. There's a difference between buying from the owner, so to speak, or buying from the founder or buying for the person, like who it's their baby, than buying from a person that that person hired. It's just not the same thing. It's the same way I feel when I'm in a restaurant, right? And the Mater D comes over and asks me how I'm doing.

I'm like, oh, I'm doing great. You know, thanks, thanks for asking. But then the owner comes over and it just feels special. And I know for a fact that guy doesn't give a shit how I'm doing. Right. But it's, but I just, I, I feel this like sense of like importance 'cause like, you know Sure. This idea of it, and like I said, he, he's not gonna like get me a nicer drink. He's not gonna make sure my bill's taken care of. Right.

Like the mader d might, um, he's not gonna do anything for me, but there's just something about his presence and his delivery that just feels special. Yeah. And I say that to say if that is a meaningful part of your job. Or what, what your company has to offer, you know, where you work with your clients, where you, your outward face of your company, et cetera, and you separate that and just say, oh, now this person is that person. I'm not saying it can't work.

I'm saying you have to recognize you've taken something away. And, and we're gonna get into this in a moment when we talk about stuff you can't hand off. But I think when, when I look at, I mentioned at the beginning like COO level stuff, there's stuff where I'm like, you just need to be competent. To do it well, you don't need to be special. Okay. Yeah. This is a bad example to start with 'cause it's, it's almost not true. But hiring. There's a certain, like there's certain roles.

Yeah. You seem to be competent, right? You seem like not screw it up. Yeah. And there's certain, basically you're hiring like the third, fourth, or fifth version of that same person then that's what I'm saying. Yeah. Right. If you're hiring engineer 23, you just need to not screw it up. But when you're hiring engineer one, you gotta be special.

So, you know, depending on the maturity of the company, and obviously if you're thinking about kinda like hiring somebody to replace you, you've got a slightly more mature company and that could mean for any, any level. I also think that, you know, things that, that you can and should hand off are anything where if you could be gone long enough and it can still get done, you probably shouldn't be doing it. Right. Yeah, that's fair.

You and I play test this once a year, uh, in December when I leave for my little hiatus, uh, once a year and kind of do go do whatever it is that I do and I get to see. One of my responsibilities got done really just fine without me, without me. And my first thought is those are all things I can hand off. But I also see, and this is not just specific to that one month just in life, that there are certain things that, um, if I do hand off. There's a problem. I'll give you an example.

In the last 25 years, I've been the CFO of every company I I've worked at. Okay? Yep. It's like my job I never talk about. Okay? Yep. But you and I have worked together for a long time in this capacity. I will never hire for that position. I will never, ever, ever hire for that position. However, we've had plenty of finance people. People, people running payroll, people doing bookkeeping, people, whatever, people handling the ops side of finance. Not the same thing as it would happen, right?

Not the same thing, because I wanna know at the end of the day when that number goes a little bit off, when it goes from 200 to 1 98, I wanna be the first person that sees it. Yes. Because I wanna be able to jump into it. Now, not everybody else, you know, thinks about the numbers like that, but I sure as hell do. Let's shift gears. Let's talk about what we cannot hand off. Sure. Because I think this is probably the more substantive part.

Um, for you, if you think categorically, if you were to hand hand off the business, what is the one thing you would just absolutely not hand off?

I think one of the places that you do start to see degradation is, is within company culture. And that's an interesting one because it's, it's the kind of thing where like. It isn't necessarily somebody's stated responsibility either, right? Yeah. Depending on how big the company is, how many co-founders there are, how, how, how broad or, or, or or narrow the, the management team is.

But I feel like culture is one of those and I, I think, look there, there's probably three or four for me, strategy and vision. You know, I think that kind of to your point before, right, like. Tim Cook doing a good job running the thing. There is nothing visionary about the guy. Right. Uh, he'd probably say the same thing if he was listening to this podcast. Right. Not his thing. Yeah. And by, by comparison at least. Right. He's not that level of visionary.

Um, so I think strategy, vision, culture is, is a big one for me to some degree. I think you use the example of hiring, but I think like, again, there's a point in time, so I think it also depends on the stage a little bit. But I'd say that like those, those two or three. I think that they're super important in that they also link together, right?

Because if you've got, you know, you may have the right strategy, you may have the right vision, but if company culture has degraded to a point where they're not working together, they don't care. You've lost, you know, passion, you've lost drive, you're not gonna achieve it anyways. And so I think there's, there are pieces of a system that all tend to degrade either one at a time or together, but the impact's kind of the same, right? It's links in a chain.

I had this one of the most fascinating exit interviews ever with a developer back in the day. Okay? And I've never seen someone be so incredibly honest in their exit interview, right? Developer comes to me and he said, listen, you know, it's, it's my last day. I'm going off to another company. He's like, but I need you to hear me out when I say there are two reasons or two things you don't know about. Now that I'm leaving, I, I can tell you, I was like, oh, okay. Interesting.

That's a, that's a big lead up, right? Yeah. Um, he's like, I've been embezzling from the company. Right, right, right, right. Uh, so he says first thing, and this is like way back in the nineties, he's like, work from home is bullshit. Right. And we didn't work from home like long before people could like spell work from home. Yeah. And I was like, what? What do you mean? He's like, dude. All I do all day is sit home and do bong hits and sometimes work. Right?

He's like, it's just an excuse to just fuck around. I was like, wow. Wow. Okay. Too bad you're leaving. Yeah. And so, no, but he was actually very talented. Uh, and so the second thing he said, he said, the reason I'm leaving is because I didn't come here to work for the guy that, that you replaced yourself with. Mm, yeah. I was like, huh? I was like, go on. He said. Listen, I know we're not super close, but you recruited me like you found me. You sought me out.

Like, like you, you, you got me a across the table in a restaurant and you convinced me to leave my job. Yeah. And I believed in you and you're not here anymore. Right. And, and I'm not the only one. That was the thing. He, he really said. He's like, you need to pay attention here because you're, you're losing your team because they feel you abandoned them. I was like, damn, that's a, yeah. Thanks for the heavy stuff on your way out, bro. Right. Um, but, but he wasn't wrong.

He was a hundred percent No, no, for sure. On hearing that, did, did it change anything about just even how you, how you approached handoffs or, or even like, did it change your, your feelings about them overall? Like, like maybe this, this is really isn't worth trying to hand stuff off. It was the first time I, I, I didn't even know it was a thing yet. I mean, I was like 25 years old, right?

So I, I was learning on the job, like everything was new to me and I was like, huh, do other people feel this way? And so I just started to dig in and I started asking a lot of other people, Hey, like, you know, since we brought new guy in, are you still good? They're like, no, it wasn't even, it wasn't even like, oh no, I'm, I'm cool, man. It's fine. Every person I talked to was like, no, this culture sucks now that you're gone.

And, and it's funny, they weren't trying to hype me up, like, you know, you were so great. They were more like trying to like, not attack, but like, like put it on me. They were like, dude, you left us right. Not cool, bro. Yeah. And I was like, wow. I didn't even see it coming. And so to your point, I was the culture. Right. I drove kind of our irreverent culture and kind of like our fast and loose and our, everything else like that.

Ironically, we brought the other guy in to make that go away 'cause we thought it was gonna be a liability, right? Like every internet company of the era. And it turned out it was the reason people that were there. Founders admit culture, right? Like we are correct the culture, uh, to begin with. I think in best case scenario, you know, like the, the, the hired gun, the replacement maybe can maintain the culture. But probably not. Yeah, probably not even.

There's a difference between culture being, it's, it's uh, like wacky Wednesdays, right? Or, or Hawaii T-shirt Fridays. Right. Like, just don't worry. Even though Will's gone, we're still doing Hawaiian t-shirt, Fridays gang, nothing will change. There's just like, there's company party, there's whatever. Right? Yeah. And there's a dramatic difference between some kind of crazy fun just broke out. Because everyone had permission to just have fun, you know what I mean?

Like, because the founder was having fun or the manager was having fun or whatever. It's, it's, it's how we fell into playing hockey. Right? Yep. Like, you know, for those that aren't familiar, that@onepointstartups.com was very serious about playing hockey and on Friday at three o'clock, the entire company would pack their stuff, go out in the parking lot and play street hockey together.

It was incredible 'cause it was a great team building thing that like wasn't intended for team building, it was just, hey, it's nice outside. We get to play hockey in the street. It was one of those things where had we hired quote management in like if private equity came and bought us and put like actual professional management, no one was gonna be playing hockey. Like this is just never gonna happen.

Well, probably not, but they probably would've at least insisted that we start with the, the appropriate safety equipment, which we eventually got to. But if you recall, will, the way we got to proper safety equipment was somebody's finger got slashed. Okay, we'll get gloves. Somebody got a cut above the eye. Okay. We'll get helmets. Right. The goalies are complaining. They don't wanna be goal anymore 'cause they go home covered in bruises. Okay. We'll get some pads.

Yeah. That, that would've been handled very differently.

Yes. I would say the other thing that you can't hand off and maybe the most important thing to me is urgency. Yeah. Man, you can't rent 3:00 AM panic. You cannot Exactly. That stuff. It just doesn't. Doesn't work. Hire the three and panic. Right. And Ryan, you and I get really anxious about stuff that most people would not either see or care about. Okay. Wouldn't, wouldn't even even register sometimes. Yeah. And sometimes it, it leads to nothing.

But more often than not, that little bit of intuition that we have, that something feels off and we start peeling back the onion. More often than not, it leads to something. Yeah, and I remember like in a, in a previous company, one of my co-founders said to me, they said, every time you get that itch, there's a problem. He, he said, I don't know how, like, how you do that, or like, you know what you're tuning fork is, but as soon as I hear you say, Hey, this might be a problem.

Yeah. I now look at it as it's absolutely a problem. We just don't know where it is yet. We, we, you and I even refer to it as like the Spidey sense. Right? Exactly. It's a thing where it's like, yeah, exactly. Yep. I don't know exactly what I'm reacting to. It's something you feel, it's the way that, right. We are consuming the information and energy around us. Yeah. At Lisa, this is part of what I was trying to get at before with the metabolic rate.

It just, we consume and, and digest things differently than anyone else does, and especially where urgency is concerned. You know it, no one sprints after a problem, they don't even know that they own. Right? And, and, and yet with a founder, we own all of it, right? Every single one of those problems is ours fully. And so we sprint after. All of them now. So the question becomes obviously like, does it mean we're chained to this thing forever?

No, it, it doesn't mean we're chained to it forever, but we can't unlink entirely. We cannot that that is, yeah. If you wanna guarantee this thing goes to the bottom of the ocean, disconnect entirely and see how that goes. The key here is to disconnect from as many things. That you don't wanna do, can't do, et cetera. But while keeping tied to the things that matter, maybe it's the numbers, maybe it's the culture, maybe it's just that, that sense of urgency. You wanna be tied in enough, right?

You want, you wanna let the kids alone, and I'm not equating, uh. Fully grown people to kids, but just people that, that are acting on, on their own agency enough so that they can kind of do their own thing and you're out of the way, but you're never that far away. You're never that far away from what's happening from your ear to the ground. What's happening with the culture? Like I was saying a moment ago, the developers say like, Hey, you're gone and it's a problem.

You always wanna have your ear to the ground, no matter how much you feel you need to disconnect. You probably do feel like you need to disconnect quite a bit by this point. You know, you, you, you want to just recharge. Yep. And you deserve that. By all means, get the break. Do not get the break at the expense of being connected to your company because as soon as you sever that tie, you're screwed for the entire time. 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@www.startups.com to see if it's for you. Could be just the thing you need. I hope to see you inside.