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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 EP276_Audio Version
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Speaker: [00:00:00] Welcome back to another episode of the Startup Therapy Podcast. This is Ryan Rutan, joined as always by Will Schroeder, my friend, the founder and CEO of startups. com. Will, there's this notion out there that every time we start a new startup, an angel gets its wings. I mean, every time we start a startup, it gets a little easier, right?
There's this myth that like with each progressive foundation that we become better and more experienced founders, and it just becomes easier and easier. Easier and easier and easier. Is this myth? Is this legend? Is this reality?
Speaker 2: You know, I think what's interesting is some of it's true, but a lot more of it's not true than you would think.
That's for a lot of people that come to us. I mean, like literally our business is helping people. You build startups and you become founders, et cetera. So our experience there means a lot. And so particularly first time founders will come to us and they'll be like, you know, tell me just all the secrets.
And in truth be told, there are some secrets. I mean, there are some things where like, if you don't know how to do this, you will fail and we can just teach you how to do it and you [00:01:00] won't fail. I mean, that's some of it. There's other parts where it's like, we can teach you everything and it doesn't guarantee you anything, right?
It's just the nature of life. What I thought would be cool. Is if we talked about, you know, kind of, you know, what our experience set is, how much of that has helped us in successive, you know, startups. Um, and how much of it didn't make a lick of difference, no matter how experienced we got. It was just as hard.
Just as hard time. Yeah.
Speaker: Yeah. You know, it's, it's such an interesting thing too. I think the experience, it's a bit of a double edged sword. As I go back through some of the repeat episodes, right? So the things that happened during the first startup and the second and the third and the fourth, in some cases, there, there was a greasing of the rails saying some cases it was just like, Oh, I know that's coming.
So that's going to feel a little bit better in other cases, because I was experienced, it turned what was a relatively simple decision. The first time. Into a much more complicated onion layered nuanced decision that I [00:02:00] labored over a lot more partially because I knew what the consequences of getting it right or wrong were.
It doesn't mean I did any better with it the second time. It just means that I had to think about it a lot more. So it is, it's super interesting as I go back through, through history and think about like, you know, where, where experience helped, where experience didn't help. But then in the areas where it's a little less binary, where it's just like, maybe just kind of complicated things in some places, maybe for the better, right?
But definitely more complication.
Speaker 2: I'm drawing like when I think about this, my own experiences, but also because we work with thousands of other startups, you know, we get to see their experiences as well. I'm drawing from, I'm going to call it three different experience buckets, I guess, when I'm talking about these.
Um, one would be my own startups and certainly yours as well, right? And we've all done many, many startups, um, from scratch to final resolution, be it good or bad, right? So we've seen the cycle many, many times.
Speaker: Final resolution.
Speaker 2: Yeah. The, the best, uh, comparable I could say would be like having a child, you know, from, from birth to, uh, to, to push you out of the house [00:03:00] and you have all different experiences and how that goes, right?
Yeah. So that's one bucket, you know, we're drawing from, we'll talk about on the show. Um, the second bucket would be, uh, you know, as it happens at startups. com, you and I bought a lot of companies. Right? You know, we did six acquisitions, but, but we, we did diligence on over a hundred companies, right? So we were in the weeds with an awful lot of startup companies.
So we got to see those journeys as well. And then jump into those journeys, take those companies over and see them through. I think that's a unique perspective because a lot of people only know how their stories end. We know how other people's stories ended because they became our story.
Speaker: They became our stories.
Yeah. And it was super interesting to see too. Cause like we would, you know, back into some of the decision making that had been made up until that point. I remember distinctly thinking that there were some points that failure where I was like, you know, I would have done that very differently. There were also some places where they had achieved some success, which is what made them interesting to us.
And I would have been, I would have done that differently too, not for the better. And so that's what's fun, right? [00:04:00] I wouldn't have gotten that outcome, right? I would have done something very different at that pivot point than they did. So yeah, I think that is a super valuable experience that we bring to the
Speaker 2: table.
The third bucket that I think we're going to draw from in this conversation is something that like, I don't take for granted, but But we tend to forget about you and I is that we have the benefit of living the lives of thousands of other founders. It's kind of, you know, what we do at startups. com. We, we work directly in the weeds with all these founders.
And because of that, it's almost like think about in life. If you had like a choose your own adventure. And you have like four different ways things could have gone. We have this unique perspective in being an advisor that we get to see all four paths. Yep. In multivariate testing where we get to see different versions of how people dealt with A, B, C, and D at a massive scale.
So because of that, we get to see lots of repeat founders and kind of how they do things differently and kind of, you know, what goes through their head. So in this conversation, we're going to draw from all of that. We're going to draw from all of those experiences as well as our own and talk about what's [00:05:00] easier and what doesn't get easier whatsoever.
Let's start with what's easier. What's the first thing that comes to mind? You've been doing this for a long time. Both of us are in a 30 year range on how long we've been doing this. What's the first thing you think of when you think about what's easier?
Speaker: You know, well, what's easier? I think it's expectation management, right?
I think it's, it's the fact that we sort of know who was it said it, uh, John Kabat Zinn, maybe you can't stop the waves. But you'll learn to surf something along those lines, right? Which is that you just, you begin to expect it. You begin to know that it's coming and there's nothing you're going to be able to do about it necessarily other than get through it.
And so I think that that muscle does get flexed. It doesn't make the things that suck, suck any less, really. It's just your reaction to it is a bit easier. I think that, you know, you get used to the ups and downs. I think that's the big one for me. It's the one that of, of all of the things that have either.
Gotten better or not. That's the one that's gotten better the most.
Speaker 2: There's this, this scene that I think I've mentioned to you before because it [00:06:00] always plays in my head. The opening scene from Saving Private Ryan. And they're all rushing, they're all rushing the beach and people are getting mowed down and it's, it's, it's, it's
Speaker: Horrific.
Speaker 2: Disgusting. Yeah, horrific in its own right. The fact that it actually happened is like way more horrific. Yes. But, what I remember Is there's like this sergeant or commander. It's just walking confidently around the beach this entire time. Guiding people, telling people where to go. And he's like, dude, I'm either gonna get hit or I'm not, right?
Yeah. Oh, that's absolutely
Speaker: a sergeant, by the way. That's absolutely a sergeant, not a lieutenant. They make a big deal of the fact that that's a non commissioned officer. That's the guy who learned to fight by fighting not at West Point. I mean, they're making a very distinct point there.
Speaker 2: And I remember thinking, That's the
Speaker: third time founder, right?
The lieutenants are the first time founders.
Speaker 2: And it was interesting because, you know, as we've gone through this experience ourselves. We've been running startups. com for over a decade. Our staff, many of them are young just by nature, right? They haven't seen twists and turns, right? And so we see it not only with startups.
com, the company we run, but with all the [00:07:00] companies we work with, all
Speaker: the startups,
Speaker 2: as well as the companies we acquired, you know, things like that. And so. Where like say within our own staff and nobody in particular, but within our own staff where they're like, Oh my God, like this thing's happening. And we're like, yeah, of course.
Right. Like they're on that beach. Happened a hundred times before. Going like, can you believe this is happening? You're like, yeah, no, this is actually how war goes. This is exactly how
Speaker: it goes. This is what it looks like.
Speaker 2: And so I'll give you an example. You know, some people can, can relate to when COVID hit.
Right. Do you remember like the feeling that we had like across the company, like, oh my God, what's happening? Right. Like, the whole world is shutting down.
Speaker: Yep.
Speaker 2: You know, our response was like, name in our first rodeo. Like my, yeah. Maybe this is, uh,
Speaker: maybe the world's shutting down we've Yeah.
Speaker 2: Or it was like, look, we shut down in the.com crash.
We shut down in the financial crash. Yeah. Like shutdowns, like, like, and, and this is what we do about it. When I say easier. The money still stops coming, right? You know, the part where we're saying, uh, it's like all of a sudden, because we've done it before our customers keep paying and everybody else doesn't, right?
That's not how [00:08:00] it works. But I think you touched on something and I want you to expand on it. You could kind of see around the corner. You already knew how this story plays out. What did that look like for you?
Speaker: You just, you start to know that like after this wave, there's going to be another wave or after this corner, there's going to be another corner.
And so you just begin to expect that. I think that the, the challenge early on is that we have So little understanding, like the first time you have so little understanding of how many corners do I have to go around? Right. And the answer is, well, probably infinite number. There's always going to be something new coming.
And so if you got into this, hoping you make it around a couple of corners and then you'd hit the straightaway, it's just not the way it goes. Right. And so I think those of us who've continued to do this thing, despite statistics have understood that, like, look with, with experience, let me go back to the wave analogy.
I'm going to get off the corners, back to the waves with, with experience. All right, comes a deepening of knowledge. But it doesn't necessarily change how turbulent the surface is. The ocean may be deeper, I may know more about what's down [00:09:00] there. It does not necessarily change with the surface. And as long as you're okay with that, and I think that's part of what happens, is you become okay with that.
I certainly wasn't cool with the fact that the minute I put out one fire, there was another fire, and then another fire, and then another fire. At some point, you just realize, Part of my job is firefighting, right? Part of my job is going around corners. Part of my job is riding waves. And that's okay. I think that's, I think that's what happens over time is you just get so used to the undulation.
It's not that you don't notice it anymore. And it's not that it doesn't matter. Cause as you said, like when the money stops coming in, the money stops coming in. That's a big problem, but it's how we react to it, right? It's like, Oh my God, this is the end of the world versus now this is the next fire.
Let's put it out.
Speaker 2: You bet. You bet. I also think you start to avoid what I'd call making duplicate mistakes. Right. There are a whole bunch of, yeah, ideally,
Speaker: but,
Speaker 2: but, but I would say that there are like a whole litany of things that almost all of us have to make this mistake for the first time and kind of have to live through.
It's like a bit of a rite of [00:10:00] passage, first time founders, when they go through it, they go through it for the first time and they can't believe this is happening to them and they can't believe all these things. And the second time founder is like, Oh, Oh wait, that just happens every time. Yeah. I saw this great meme on social media the other day because this always reminds me of like people learning relationships for the first time.
It said my 13 year old son just broke up with his girlfriend and now he's writing her to get his hoodie back. He's about to learn his biggest life lesson, right? It's like such a perfect thing. You only need to learn one.
Speaker: You only have to learn that once
Speaker 2: we have the benefit of being like, Nope, not doing that again.
Right. Cause you had the chance to actually make that mistake and get the lesson the first time. You know?
Speaker: There's some that are pretty obvious, right? I think there's some of the, some of the mistakes are kind of nuanced, but I think if we, if we dig into some of like the kind of the more obvious ones, it'd be things like taking on co founders for the wrong reasons, right?
Like I needed a developer. So I took on the CTO who was just a junior developer who now I will regret later. It's things like just overstaffing in general, raising too soon, [00:11:00] raising too late, right? Like just, or mismanaging capital spending in the wrong places. There's a lot of those things that I think.
You do, you do reflexively learn. I think that was kind of the point I was making really early on, which is that some of those decisions felt really easy the first time through. All right. And not that I made them well, they were just easier decisions because I didn't know any better. Right. So it was like, should I hire people?
I'm here by myself. I should probably hire people. What are they going to do? I don't know. Right. We'll figure that out later. Like that's a second order problem, Ryan.
Speaker 2: And you don't understand that overstaffing is even a thing. No, you're like, Oh no, you're supposed to grow. How could we possibly be
Speaker: overstaffed?
There's no staff, but
Speaker 2: that's funny.
Speaker: That's funny to think about, right? Because you and I know that you can go from one person to two and actually be overstaffed.
Speaker 2: Yeah.
Speaker: Right. That's the thing. It's really
Speaker 2: the case. Yeah. It
Speaker: does not occur to you the first time you're going through that because you think like overstaffed.
Well, that must mean like 10, 20, 30 people or something. Right. Like there's some arbitrary number. That's not the number that you just hired. Um, that feels like maybe that's overstaffed because you're overwhelmed at that point. Uh, but you're overwhelmed with [00:12:00] things that probably won't be solved by staffing up.
Speaker 2: So there are like colossal life lessons that I would argue you kind of have to live through to really get. Yeah. Right. Um, like that hoodie experience to really appreciate what that means to not do it again. So if you have done it again, right, like I'm, I'm nine times deep on starting companies. There are a ton of stuff that I learned in startup two or three that I've never done since.
Sure. And that is invaluable. And I think when people are, are thinking about, Oh, this person has a lot of experience, they must not have to go through these things. We'll talk about that part later. But um, some of that's true. I mean, some of that, I'm just like bad hires. Right. See somebody in an interview, right?
And they check every box in the interview, say something crazy.
Speaker 3: Yeah.
Speaker 2: And they don't even realize they said it. Right. But I'm like, nope, nope, nope. I've been there. We know where this
Speaker: goes. Yeah. Yup.
Speaker 2: Yup. It's things like that, that allow you to essentially avoid colossal mistakes because you've already had that [00:13:00] experience.
The other thing I thought was interesting is in raising capital, but not for the reasons people think. So people tend to think, Oh, we've raised before. VCs must know you and love you and want to invest in you. Ideally. Yes. But statistically,
Speaker: right.
Speaker 2: So you got some explaining to do, but I don't think it's because you have a reputation for having done, done it before that, that could help again.
It could go either way. What I think it is. Yeah. Is you know what it actually is? Yeah, like a hundred percent. You can see through the bullshit. Yeah. And all the pixie dust of like, Oh, investors are going to come. They're going to give you money and so much expertise. And they're going to help you along the way.
Like, you're like, no, they're going to be the biggest pain in my ass ever. And And I'm, I'm going to take it with a grain of salt. Uh, pixie dust is worn off at that point.
Speaker: Yeah. Yeah. I mean, it's rare that we talk to a founder that's raised more than once, who didn't do it at least slightly differently the next time and the next time.
And then at some point say like, Hey, maybe I'm never going to do [00:14:00] that again. Like the next thing I build is just going to be going to be mine. And we see this, I mean, you know, across the board that like it changes over time, just even how we treat things like our cap table, right? Like how much equity we give away.
I was looking at this the other day. I was, I got curious about, I remembered, you know, Elon had an early exit in, in zip two at the time they sold that. And I knew, I knew they'd gotten squashed down in the cap table, but I didn't know how far he was sub 6 percent when that sold. Right. Not to take in 20 million home was it was a bad deal, but they sold the company for like almost 400 million.
And so when you take away. Funny at that point, right? It doesn't, doesn't feel amazing, right? And you can see that you can see the difference in the way he's structured things since then with, with Tesla, with SpaceX, completely different, completely different structures.
Speaker 2: 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 [00:15:00] 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. I think if I reflect back on the things that really stand out to me, like, man, it's way easier than it used to be. A couple specific things to me. Not necessarily categorically to everyone else.
One of them is I'm more of a, I'll believe it when I see it kind of guy, right, particularly with people. Um,
Speaker: we went through this yesterday. We went through this yesterday. Well, we had, we had an example where there was like a proposal that needed to be needed to be made for potential partner. And we're like, we could go super, super deep on this.
Let's just test the waters, right? Let's, let's put a toe in and see if there's anywhere to go from here. Whereas like the first time through you and I would have been up till, you know, three o'clock in the morning last night, we'd have been, you know, crafting that. Like, do you think [00:16:00] this font works better than that one?
Like, what if we were, well, what about, what about, what about landscape? What if we turn the whole thing on its side? Like, you know, you go through all of this shit and you end up doing things that you just don't need to do. Right. So I think that it's, it's an illustration of that. I'll believe it when I see it said differently.
I'll put in the amount of effort that's required for right now, which as a first time founder, no idea. You're like, I guess I'll throw everything at this problem, whether it's that big of a problem or not.
Speaker 2: In all of the, the implied commitments that people make to you as being a startup founder, right? So you're hiring people, right?
Whether it's a developer or salesperson, whatever, they're all making implied commitments vis a vis their resume, what they say in the interview, et cetera. And in, when you're, when you're doing this for the first time or when you're young in your career, you tend to take it at face value. You assume that because they can do these things,
Speaker: that they
Speaker 2: will do these things.
Which you find later is a way, way. Go back
Speaker: to the investor's discussion, right? Go back to the smart money thing, right? This [00:17:00] investor has all these other portfolio companies that could possibly buy from us. This investor has this massive network of people they could turn us on to. This investor has all this stuff they could do, they could do, they could do.
Will they? Probably not. Was it in the term sheet? No. Was it written next to the zeros on the check? No. Then it's probably not going to happen.
Speaker 2: Of all the things I think about that have made my life easier as a founder with 30 plus years of experience in just doing this for a living non stop.
Speaker: Yeah.
Speaker 2: I think I would rank understanding people better than any of them.
Right. In as much as it's not even about being callous or questionable. It's more just not being oversold where I was like, Oh my God, this person is going to be a co founder. So they're going to be so engaged.
Speaker: Yeah,
Speaker 2: maybe,
Speaker: maybe,
Speaker 2: maybe I've seen plenty examples where that was not true, right? So maybe, or, you know, again, you know, we just, we just partnered with this company and they're so fired up.
We're going to do so well together. So
Speaker: I need the quarterly report
Speaker 2: in a quarter, right? Yeah. And, and see how it went. The reason you just, you touched on this [00:18:00] when we started this, the reason that's so valuable is holy shit. Does it save me time? And more importantly, emotion. Right. Like when that developer doesn't work out, I'm not shocked.
I'm like, yeah, okay.
Speaker: The first time, maybe a little, the second, but by the third, fourth, fifth, sixth time, somebody didn't live up to expectations. I realized one of two things. One, maybe I had the wrong expectations to, I have no right to have expectations for anybody, and even if I do, it won't really matter, right.
They're going to do what they're going to do with my guidance, all that stuff. Sure. Right. But I cannot, I cannot let this completely, completely deflate me. Yeah. I think the people problem is a big one.
Speaker 2: And so the other side of it was like, you know, again, with people, I remember early in my career when someone would leave, I would take that as such a massive personal affront.
Yes. Like, what did I do wrong? Like, where's the gap in my leadership
Speaker: bags and said, I'll see you later. Good luck, kid. Right.
Speaker 2: Almost like [00:19:00] them leaving was like them divorcing me. I mean, it's a really, really, really personally what I didn't realize. Like At the time, and it took me many years later to realize this, is people leave.
People leave all the time. Like, um, I've done nine startups, which means I've left nine of my own companies. I've divorced myself. So, like, it took me a long time to get less emotional about that. And I think about how much time and effort and distraction was caught up in not having that muscle. Right now, be able to process and go, Oh yeah, of course.
Right. On to the next one. I'll see you back here in five years. Like, you know what I mean? Like, like circle life, right? Like, I'll see you again. I
Speaker: think that that emotional maturity is one of those things that you, we also learn as founders that doesn't go back, right? Like that, that's one of those things that does become quite useful.
And, and you do continue to flex that. So I think situations that require that emotional maturity, those are all easier by some degrees based on how much you've matured over the time.
Speaker 2: Agreed. Let's flip it. Let's go to the other side [00:20:00] altogether. What is not easier?
Speaker: 30 years in. Hang on. I've got a little bit of devil's advocacy for the people one here because I, I just, I couldn't leave it alone.
I couldn't leave it alone because we have been doing this for so long, i. e. we're multi time founders and we've done this over, over a period of time. You go through some generational changes. You and I have been through this where it's like. Well, but in our day, when you hired somebody, here's what they did.
And then the millennials came along. We're like, yeah, grandpa, it's not how it works anymore. Right. And then Gen Z and now whatever's after that, I've lost the plot. Right. So there, yes, the experience does help, but again, I think we have to be a little bit careful about letting our experience temper. Our, our expectations and saying that like, because this is how all of my previous employees were, this is how all the future people will be.
And that just has not been the case. So just one little caveat to the people getting easier.
Speaker 2: Let's go back to not easier. What is not easier? Um, no matter how many times you do this, Why isn't it easier? Like why? [00:21:00] What's, what's broken that like, you can't master the thing? What's the first thing that comes to mind?
Speaker: Well, look, I think that there's, let's, let's talk about a fundamental reason why it doesn't get easier every time. Because we're not doing the same damn thing, right? We're doing something different every time. It's a variable. Every time we start a startup, we're essentially setting out to do something that's never been done before.
Even if we've done something else before, right? Remember when, I bring this up every, every like 90 episodes or something. Remember when Michael Jordan decided to play other sports? That was neat for a minute, right? Like it didn't make it any easier, right? Like he did not win a world series. I think that's the biggest thing.
So like we can get into some specifics around what's not easier, but I think the reason the core fundamental reason, and this is where we trip up and we're like, boy, but I've done this before. You've done a thing before and you've done a thing that looked a lot like this, but you have not done this thing before.
So let's, let's start with that. I think. Okay.
Speaker 2: So, so let's talk with the product, right? Yeah, sure. [00:22:00] You haven't built this product before. So let's talk product market fit.
Speaker: Sure. Product market fit is just as difficult every single time. And every single time you have experience building really similar products in a really similar space, it's still no easier, right?
Maybe, okay. Maybe it's a little easier. Maybe it's a little easier. Like you already know some of the definition around the audience. Maybe, right. You're like, okay, we know some of the things that they like. We know some of the language they use. So we've got some maybe, you know, uh, communication marketing product fit, but product market fit is always really, really tough because even, even for example, you built something in the same space before that space has probably changed since the time you did that.
Right. By virtue of you having built something for it changed, right? There's so many variables, right? Like, Oh, well then we went through a pandemic. Oh, then AI came around. Oh, then whatever else happened that changes that market fundamentally.
Speaker 2: We want to believe that if we've done it once that we can do it again, whatever that thing is, the thing we built before, et cetera.
It doesn't work like that. It just doesn't. And, and, and [00:23:00] I think it's a bit of an arrogance to us as founders. Thinking, well, I've done it before. So of course I can do it again. And part of that arrogance and confidence we need.
Speaker: It's the same, it's the same as the biological joke that gets played on us when we decide to have children and then more children and then more children, right?
Like you forget what you went through and you assume it'll be easier. You're wrong in both cases.
Speaker 2: Every time, like, like you're saying, Ryan, every time we restart, there are so many variables we change and there's a few we, we can't get around. When we started the one thing at the one time, we can't go back in time and be that same time period.
The world changed, and the world changed in a ton of different ways. In 94, I started one of the first interactive ad agencies. That's awesome, and it was really successful. But that was 30 years ago.
Speaker: Yeah.
Speaker 2: Your
Speaker: qualifications for starting a digital agency today would be
Speaker 2: less. I mean, like, right. And so just because I was associated with that category, it doesn't matter.
Given another more recent example, [00:24:00] you know, I mentioned that the last company that I did before startups. com was a company called unsubscribe. com that I started with Jamie Siminoff, who I mentioned is the founder of ring, the doorbell company, Jamie and I both had like, six companies before that. And Jamie had some success with another company.
I think it was called Simon scribe, but he had like five others that, that did okay. Not great. Right. Same with me. Right. I had some successes and failures, whatever. And we worked together, which you would think would be like more. Like, uh, horsepower and to some degree it was in that company did. Okay. Not great, but, but I guess my point is it's just, it didn't make it any easier in the same way that the, the five companies I did before that are the five companies he did before that didn't necessarily all hit.
I'm of a, of a very certain opinion that as a serial founder, you are starting from zero. Every single time you've got some advantages, some experience, but product market fit ain't one of them.
Speaker: No, no, it's not. Look, in that, in that regard, experience is a great teacher, but there's no shortcut for understanding your [00:25:00] audience in the context of today.
Whatever you learned in the past is a history lesson, right? It's exactly what it is. And it is helpful, right? Like if you've gone through finding product market fit, Then you know, what that process looks like and what it feels like, that's helpful, right? That part of it will be easier, but getting it process wise, but getting it is absolutely no easier because you're starting from that same point of almost zero information, lots of guesses and a ton of variables.
You gotta go make some constants out there and figure out like, what of these assumptions are true and are we close to matching the product with the market need?
Speaker 2: The other thing I found, not just for myself but watching other companies, is every time they restart, you know, build something new. Yeah. Um, what's not easier?
Marketing. I think marketing, I mean, even if you get it, hell, I came from an interactive agency. Like, like I was grown up on this stuff, right? It's a slog every single time. I mean, you're our CMO, you know, better than anybody, you don't get any bonus points, like maybe you have some media relationships or things that worked well in the past, which I also think is sometimes a.
Mark against you because you tend to rely on things that aren't [00:26:00] current anymore.
Speaker: Exactly. You may lean on relationships and assume that those will be the things that get you because they were easier to reach than maybe the one that actually would have been more beneficial. Now, I think there's a, there's a real danger in using past experiences as a crutch.
Speaker 2: Yeah. And with, with marketing specifically, New product, new audience, new timing, et cetera. And by the way, when we're talking about this experienced founders, I'm sure by now we're like, they're next door from nodding their head. Cause they're like, dude, I went through all, I mean, we've talked to all of you.
So we're, we're telling you what you told us, right? So this is no like special thing from us, but the other side is what I want folks to really listen to and lean in on. I want new founders to listen to this. Yeah. I want new founders to listen and go, wait, hold on a second. You're telling me these like super experienced people I'm going up against.
They don't, they don't have like a distinct advantage on me. Yeah. They have some, we talked about some of those, but the ones that really matter that you should be more concerned about, like, are they getting to product market fit faster than we are? Are they going to, they have a massive jumpstart on marketing.
Like we don't, not really. I mean, again, it's better than zero, but [00:27:00] it's not the ace in the hole that people think it is. Talk to enough VCs that have funded enough second time, third time founders. And they'll tell you the same. They'll be like, hit it out of the park on the first one. Second, third one, haven't seen shit since.
Speaker: Yeah, man. No, I, it's one of those things where like, I think success is never owned, right? We don't own success. We rent that shit. We rented and the rent is due every single day. Right? So regardless of what you've done in the past, you got to pay the rent, right? You're going to have to reach. Achieve success.
And in almost every single case, I can think of certainly all of my own experiences, achieve it in a different way. A hundred percent different. No, not necessarily, but enough different that it mattered.
Speaker 2: Another one though, like, uh, no matter how many times you go through this losing sucks, exactly the same every single time.
Now I thought there was like a cheat code on this one. I thought that like, If you'd lost the Superbowl once and losing it again, it would be okay. Cause you're like, Oh, you know what? We get past it. We go back to training. Everything goes on. [00:28:00] Right?
Speaker: Yeah.
Speaker 2: No, I have a callous over my heart
Speaker: right in that spot.
It no longer hurts.
Speaker 2: Yeah. Right. Right. It, that does not work running out of money, going through the part where you've got to let everybody go, going back to your investors and telling them that story, going back to your customers, going back to your friends and family, I mean, everybody, right. Sucks. It sucks every single time you and I had a founder reach out to us last week, shut down the business, you know, we're just doing, you know, a postmortem and stuff like that.
Great guy. Awesome founder. Um, he'll, he'll do it again. It'll be great. Right. But what I shared with them, and I'm, I'm guessing you did too, was dude, I've been there, right? Like, I'm not going to sugarcoat this and tell you that this is, this is great. And don't worry about it. It was actually the opposite advice.
Uh, my advice was, Uh, live in it for a minute.
Speaker: Yeah. Right?
Speaker 2: Stay here. Remember this feeling? Yep.
Speaker: Hold on to this. Right?
Speaker 2: Um, yeah. Hold on to it. Document it. Yeah. Write it down. Go journal it. Because it's, it's easily the most valuable lesson you'll learn. It's a shitty lesson. It sucks how you have to learn it.
But of all the things that will give you really the most [00:29:00] pointed guidance for the rest of your life, are happening right this second. Don't let them go. Yeah. Now that said, Still
Speaker: sucks. It still sucks. Yeah. Yeah. Spoonful of sugar does not make the shit taste any less like shit. It just doesn't. Yeah. And
Speaker 2: you know, like again, I mentioned, you know, top of the episode, like when COVID hit, we're like, Hey, we've been through this before.
I have been through this before in, in the. com meltdown. I was running a very large company. And. Shit just started to fall apart, right? Like our clients, massive, you know, fortune 500 clients just stopped paying us out of, I didn't even know that was possible. Like, right. But we did
Speaker: the work and you signed the contract and my account is empty.
So I think you know what you need to do here.
Speaker 2: We had a, we had a client. I'll never forget this. It was a small project relative to where we were at the agency at the time, but it was a half million dollar bill. We'd done a half million dollars worth of work. Not insignificant, right? And, and we'd sent them the bill.
And again, it's a fortune 500 massive company. And they stiffed us. They were like, yeah, this didn't get approved, blah, [00:30:00] blah, dot com bust, blah, blah. And I was like, and but you're going to pay it, right? Because you're like a huge company. And like, we have a contract.
Speaker: Yeah, and they're like, I have payroll. And yeah,
Speaker 2: yeah.
Oh, my God. Right. They're like, no, we're actually not going to pay it. Take the mulligan on that one. And if you want to work with us again, you just got to let this one go. And I was like, wait, what? Yeah. I had no idea that was even on the table. Like I, I had no idea. I was like 27, by the way. Um, but like I had no experience, but if that happened today, having had that experience, it would not suck less.
I would like, oh, that
Speaker: happened before. Not a big deal. Yeah, no, still, still a half a million dollars full surprise.
Speaker 2: I was like, what is happening right now? I've had multiple companies that I've started that have failed and it hurt. It hurt every single time in the same way. It wasn't like better the second time might've even been worse.
Speaker: Yeah. It's funny, but yeah, stick on that for a second because I certainly, and it's, it's big things and small [00:31:00] things, not even the entire startup sometimes, but like. Anytime I've made a hire, right. And then realize it wasn't the right hire and then replace them with somebody that I thought would be the better hire.
And it still wasn't the right hire. The second one hurt even worse. Yeah. War marketing campaign. Right. And then it doesn't work. And then lunch doesn't work. And it's like, it doesn't, doesn't necessarily feel better. Sometimes the, the, the, the experience of loss can compound into feeling worse. Not like you, you get used to the fact that it will happen.
Um, but I think you're right. There is, there can be a compounding effect. Yeah.
Speaker 2: There is. And so here's what I'd say overall, if we're to take a look at just the whole continuum of experience and how much of it, you know, helps and how much of it doesn't help. Obviously, more experience helps, but what's really interesting about this startup game is how much of it You don't get to reuse, which is why there are so many first time founders that are so successful because Mark Zuckerberg can show up at 19 years old and build one of the most valuable companies in the world.
And you're like, wait, how is that possible? Like, [00:32:00] because his opportunity at product market fit is damn near the same as everyone else's. Yeah. Right. And I think when we, when we consider, um, when we're a first time founder, Hey, do I need to have all this experience? It doesn't hurt and any founder will tell you it doesn't hurt, but at the same time, this is the part that people don't get, it doesn't change the outcome, the big variables that really matter, right?
The experience helps, but the big variables are really around the things that you cannot control. And every time you do it, you're doing it for the first time. You got to hope like hell.
Speaker 3: 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.[00:33:00]