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[00:00:00] Colin Keeley: Hello, and welcome back. This is Colin Keeley here.
[00:00:03] Brent Sanders: I'm Brent Sanders.
[00:00:04] Colin Keeley: We hear two guys buying and building wonderful internet companies.
[00:00:08] Brent Sanders: sir. And over the last week or two, we've had an interesting set of discussions that I wanted to bring over to the podcast. One, one thing we wanna talk about in this episode is, this weird gray area we're playing between venture capital in private equity. So just to frame the discussion, we. We're looking at one of our portfolio companies, that we acquired, sub $1 million transaction.
We acquired it. And we're looking at the growth scale, right? It's like we really believe in the business really believe in the product. And we're kind of trying to, to frame a case for, would it ever make sense to, raise venture capital? If we could get this on a venture scale, like if over the period of four years with our own money and our, our own resources, we scale it to a certain point.
That's great. But what if we could compress that? What if we compress that timeframe down to. I don't know, 18 months. Right. And, and basically we were looking at, is there a scenario where we could raise a precede round for a business that we bought, sub $1 million and a sign evaluation that makes sense for venture. So could we use the resources. that we would spread normally over four years, compress it to 18 months, in the tech world, there's a famous saying of like, the mythical man month.
Like you can. What, what is the, the saying always gives people, you nine women can't make a baby in one month. Like this idea that you can't just add more resources and into it faster. But in this case, we feel like we could, because it, it's just, it's very clear what we need to do. We need to fix our conversion funnel.
That's it. And with that unlocking, that's the, the, the main. Technical reason why this business is not growing currently or not growing to the scale we want. So fix it. And then it's worth something else. Right. And so, I don't know. We, we were talking about, is there a world that exists?
That's like a venture studio, which is the background we come from that could exist for acquired companies, which I get kind of hot on this idea. I mean, what was your thought.
[00:02:07] Colin Keeley: Yeah, I mean, we're kind of in a weird spot. So venture capital is like, you make a bunch of bets, 80% or something go to zero. It's more like a third go to zero. A third are. Middle of the run and like return the money and then, the top 10% return the whole fund. And then private equity is like, basically buy something that's already working, use financial engineering and like operational discipline.
And just, if you keep the company kind of where it is with the bunch of debt, when you acquire it and pay it off, like that returns are pretty amazing there. What we're doing is like kind of a hybrid, like a venture equity of sorts where it's like, the upside is definitely there, but the downside is also there.
Like I would expect we never lose money on a deal. And this is something that, this equity aside is they've done. Like, I don't know, hundreds of deals. They never lost money on a single one. Cuz it's, recurring revenue at software, it's very stable. But the upside is also there. Like, so they do have significant growth potential.
Depending on what you acquire. And like, I don't know if you could really predict that in advance, but there is the possibility that one of ours becomes a home run. We don't have that yet, but if it's in a big enough space, like there's definitely potential there. The, the vertical software markets are getting very big.
[00:03:16] Brent Sanders: Yeah. So we, I think as we look at this of, putting it on a venture track, like sure, financially. And from a tech perspective, a market perspective, like all those things look and smell. Right. But the one thing that I think we struggle with, or I shouldn't say struggle, but like the thing that we don't look like in a typical VC deal is like, it's you and I running multiple companies.
Right? We are, we've put in teams in, we've put teams in place, like. I think, as it relates to VCs that were, would look at a deal like, like this, they'd say, the first thing, well, who's the passion and entrepreneur that's gonna, slave away and, and spend all their nights on, on launching this business and taking it to the next level, which I think it's a fair statement.
I mean, You focused on, on venture for a good part of your career. And I think at, at school it was your focus too. It's like, is that like a textbook thing? You need to have like a, a, a YC backable founder. I mean, that's, that's kind of the bet, right? It's, it's a big part of it.
[00:04:21] Colin Keeley: Yeah. So that's traditionally in venture capital. Yes. You're betting on the horse or betting on the jockey as well as like the market people. But venture studios are a thing. Startup studios are a thing and some have done it very well. Mike SP in Sutter hill, they have like multiple, knock it out of the park, 10 plus a hundred billion dollar plus, outcomes.
So like some people have done it really well and they. He is never the CEO. Like he's always the CEO initially. And then the game plan is whether it's like an amazing company or not an amazing company he's stepping down and he's gonna hire a CEO and give him equity and they're gonna run with it. So is it, it's a model that works.
Some we've been talking to maybe some less experienced VCs or not as good ones and they are not as familiar potentially with this like startup studio model, but it's definitely, I mean, that's what you did. That's what you ran in the past. It's the.
[00:05:08] Brent Sanders: Yeah, and we have, my only regret is just not starting more companies. Right? Like we have exactly what you just described earlier, which is you have some that go to zero and, and the nice thing about the studio is you kind of tend to see that sooner than later. You have some that are okay. And then you have some that are on track to be, billion dollar companies potentially.
So you know of that, like I've seen it work firsthand. I've seen also what doesn't work. Right? Like, and I think that going back to the idea that, something can be like, oh, well we're gonna be co CEOs or co-founders, but we're also doing other things. It's like, you do need a laser focus on if you're going to put something on a, a venture.
Scale. Like, I do think you, yes, you need experience. We also need to fully focus on that. And, and I don't think that, we conveyed that that degree of confidence. I mean, I'm super passionate about diving into this for 18 months and like really, really focusing. But most of that is because it's product stuff, right.
It's all product stuff that needs to be fixed, improved, and changed. And it's like, I don't know. Really like also I don't know if my age is a, a factor, like being a 40 year old dude. Who's like, framing that as, oh, I'm gonna take this preceded company. I think there is a certain amount of ageism maybe.
I mean, I'm not that old, right? It's not like I'm 80 or 70 or something. That's like, what is happening. But I think there is like a generational, like dis oh, you've got two kids, that's not gonna be the business is gonna be number one priority in your life. I, I feel like there, there might be undertones with that, but so it's like, does, if you fast forward in four years, like, there's definitely a way bigger opportunity.
If you, you compress our, our growth timeline, put it on a venture track, that also introduces, the downside and the stability. So it's like, there's also a, a yin and a yang to this. That's like, The positive is yes, you can knock it out the park and put it on a really high growth trajectory. The downside is you can completely destroy a business in trying to do that.
So there is an element of, what we're doing that feels a little bit more like farming, where it's like, okay, we're gonna keep the, the green pastures and be good stewards and not do anything crazy that, you we're not gonna accumulate any tech debt. Which I think is probably. I think if you think about it from a VC perspective and the way that I, I would would frame this deal is like, we would love to put it on this trajectory, but if we don't, we're cool too.
Right? Like I think that the lack of do or die is a part of the hesitation of like trying to, to do this type of studio. But I think that's the question for you is like I put it on you to, to think about is like, what if we, what if we do find. Use acquisitions as a form of like, Hey, they're all gonna be safe bets, but then some of them we can kind of, amp up or raise the risk profile on it's like, does that make sense to pursue?
[00:08:01] Colin Keeley: Yes, I think it makes sense, especially if you have like a pool of capital and we become, we should have that. Capital have become the allocators of it. And we allocate it to the companies that seem to have the most potential. And that makes sense. I think it's when you, spin 'em off and you have to go raise, deal by deal.
That becomes quite a bit of a distraction. But yeah, allocating to the, the companies with the most growth potential definitely makes sense. And that's what everyone else is.
[00:08:27] Brent Sanders: Yeah. Yeah. I guess the, the thing around like compressing timelines is really the way I think about it. Of course, we're gonna allocate towards that. It's like, does it make, there is an element to me of like, With venture you're now on this like 12 to 18 month, like sets of, especially in the pre preceded seed, ranges of things where, you know, that there's a, a cadence kind of built in versus with more of like a PE structure.
Yes. We want to get things done in like a, I don't know, four year period at the, the very, like, be teeing up an exit in four years. And so, know, we, we, we balance this line really well. To me, I, I think where we're standing is, is the right spot, which is like, we have all the upside OFC with none of the downside of, know, with the, the protection of PE, right.
It's like we have that optionality, but I guess that would to a venture investor. Like it's just not, it's not the model. Right. And so I guess the thing that I really wanted to talk about was like, do we think there's innovation in these like to be had in these models? Like, you could look at a studio venture fund, like a studio model, venture incubator or something along those lines, that being an innovation, like, do you, you just don't see the profile for, VCs changing, but if you look at these other markets, like, I don't know, the Midwest, like we're Europe where you have.
Sort of like a, an initial venture mindset and then a company settles into more of a PE like it's a good business, but it's not great. It's like, okay, it's going to return something, but it's not gonna return, it's not going to be a unicorn. It's like the real question is, what do you do with those, a investors?
What do you do with those companies? And like, how can you reshuffle them to fit into one or the other buckets? Or can we do what we think we can and like, keep them in this like middle ground. And then you end up with either great PE and that's my sense is like, if we go to sell these things or if we go to market, it's like, okay, it's a, it's a great business, but it's, it's not going to be like a, either an IPO or, a massive acquisition.
[00:10:31] Colin Keeley: Yeah, I mean, it, there certainly is the potential, like it's kind of. There's untapped upside. So it's definitely possible that you end up with an IPO. There's no like necessarily a reason why you wouldn't. But the downside is like, these things are already working. They already have hap happy customers that are paying.
And they're very unlikely to go to zero. Like, I don't know what could possibly happen, where they would go to zero actually. But yeah, it is. I don't know. You kind have to shift your mindset of like, these things have potential and they're, you're not gonna lose money in them. It's kind of a crazy. It's not a traditional VC bet.
Like maybe the better question is like, who are your ideal investors? And it may be just like these family offices that kind of get real estate. They like real estate, cuz you're never gonna lose money on real estate. But it's recurring revenue, which I guess real estate is as well potentially. But, it's just like a much nicer business model that is way more upside with similar downside protections.
[00:11:21] Brent Sanders: Yeah. And like the thing that's kind of interesting though, that, that attracts me to this is that like a lot of the companies that we look at and that of the ones that we've acquired, it's, it's an opportunity to kind of flush the cat . So basically wipe the cap table, like a new acquirer comes in, you buy a hundred percent of the company.
Everybody else is kind of like the old stories are, are gone, right? All these like promises, whatever. And you gives you an opportunity to kind of rebuild things. And with that, and with what we expect to be, our, our future acquisitions, I think there's going to be a larger and larger number of venture back companies that.
Are, are, are taking the dive and are just going to liquidate and sell to somebody like us. Like that's one of our targets. That's one of our expectations to grow in the next, season, what is, has become difficult in some of those conversations you and I were talking about earlier is like, Getting all the investors to close on a deal like that of like, oh, well, is there something we can do to kinda get the, the valuation back up?
But the reality is, is, it's doing X amount of MRR and, Y amount of SDE and market is what the market is. And it's like, it's that? Or the company's going to zero and nobody's gonna take it. So just trying to, to deal with those types of investors in a different way, in the sense that we're going to be the acquirer.
I, I think it's hard to, I think it's hard to, to really what's the word I'm looking for. It's really hard to encourage those investors to, to just kind of realize what they have versus, hold on, hold on a little bit longer, cuz it's like the cockroach in venture, which sometimes those do turn into, great stories, but it's hard to keep a team on something that's that's not working.
[00:13:04] Colin Keeley: Yeah, I would say good VCs. Like the best deals are kind of obvious, like fairly early on they're they don't require a lot of work. Like they don't require any work from the VCs really. They're just like kind of rocket chips and you're along for the ride for, and then the ones that go to zero or like kind of putts around, they waste a bunch of your time and they don't really deliver any returns for you.
So I think that good VCs get it, like, get a good PR win maybe right off the investment. Let the founders go do something. And like you could back 'em on the next project, cuz it probably walked into a market. That's just, not right at the time. But bad VCs. Yeah. They like fight and claw for every little dollar.
Which is not like how the numbers work out. It's not what you should be focused on, but they're focused on the wrong thing. And those will like push founders to stick around basically zombie companies like they're under so much like of a preference stack from the investors that it's very unlikely that they're ever gonna sell for anything that gives the founder any equity.
So they're just kind of wandering around and we've talked to some of 'em like, they're solid businesses. But their valuation that they raised that before and the money they raised, like. They're not gonna sell for anything that would return money to the founders for like years.
And, maybe you could outrun that preference stack, but more likely, you're just gonna waste years of your life that you should have just sold and walked away. And like, if you're VCs are nice, like they'll let you take away some of the money, like they'll, take the PR win bear metrics is the case.
We always bring up, like they raise money from some good VCs and the VCs just wrote off the investment. And then, Josh walked away with like a good amount of. I think more should do that. But I also think there's just a lot of people that are not great at their job out there.
[00:14:41] Brent Sanders: Yeah. I mean that, that's such a, a defining, like, are you here for more than one seat? Are you here for many, many years? I mean, that's the, the thing. The network within this and just, building a reputation. It's like, they're, they're playing the long game, which is smart. But yeah, going, going back to these companies where, I mean, we've talked to a fair amount where, and it's a terrible place to be where.
Your resources are short. You can't grow sales, cuz the resources are short. Usually goes back to tech. We, we hear a lot of that from folks where it's like, we can't sell because or or we can't sell quickly because the tech breaks and we can't invest in the tech because they're focused on fixing bugs and we can't add more developers.
There don't even more resources and you're just stuck. Right. And it's like, it it's a, it's a good, that's a good. I think to realize is like, as you said, don't waste yours of your life. If you can't raise, give it, give it to certain time consider selling. I think that's a, I think that's like the, the, the place where we can kind of come in and, and really be advantageous to the I'm not gonna lie.
I don't think we're advantageous to the, to the investors. They were hoping for a big win. Maybe they'll get some return, but it's really about the founders. Like the, the folks that are in year eight or year six of. A startup and they're just, they're jammed as you call zombie. But they're, they're basically like just in a jam and you can't undo it without recapping the company.
[00:16:07] Colin Keeley: Yeah, and this is something we could try to do. I don't know how influential we could be is like, try to go to bat for the founder, try to talk to the VCs. And like, I don't know if we could give 'em a PR win. We could 'em on a podcast. We could tell the story about how nice they were to like forgive the loan.
I don't. The other argument is like, these are just so much work and like, it's hard to deal with all the personalities involved that you just wait for these things to crash and burn, and then you pick up the ashes. And then bap founders. We've had just a lot more success with, they have much more reasonable evaluation expectations.
And it's like an amazing outcome for them since they're, they're taken effectively all the money. If they boots out the company didn't raise outside equity. So it's like, those are just easier wins for.
[00:16:49] Brent Sanders: Yeah. This all kind of comes back to mandates, right? When it come, what, going back to the investor said the original conversation, like. You say, you're a, a thing. You raise money on that thing. That's your mandate, that's your thesis, whatever it is. And it's like sticking to the plan, right?
And so, like, I'm not going back to the, the, the whole criticism or discussion. I'm not necessarily criticizing. I'm just kind of pointing to, we are, we have a mandate, I guess, like we've decided B2B SA we decide a certain size, certain like. Structure and profile want profitable companies like that's cool, but I think, between VC and private equity, you, you have like, it would be cool to see a little bit more. Like, oh God, what is the interdisciplinary investment? That's the word I was looking for? Yeah. Interdisciplinary, like, not everything's just black and white. And so I think that there are a lot of people that categorize them in this BC category. Themselves and the vs see that that are really like, they might be okay with a three X return.
Like that might be great. They might be okay with a four X return. Right. That's, that's a huge win for folks that, haven't seen a unicorn, but you know, they haven't seen a unicorn, but they also are still making, smaller bets on, basically deals that are, are destined to become okay.
Companies. Right. It's like, I don't wanna go too far into like the VC world, but it, obviously there is a, a geographic limitation to some of this, like, and that's, I think shifting greatly now, but you know, San Francisco, Miami, Austin being sort of New York being sort of the hotbeds of investment. And if like, if you're not there, you're in like Topeka, Kansas, and you're a VC investor and you're trying to, it has a role in the economy and you're trying to kind of play that role.
I get it. It's not part of the, the playbook, but it seems like we're, we're the tope, Topeka, Kansas VC, right? We're like we, this like quasi, in between VC and PE model might actually be like the right fit versus trying to kind of do something in a market where, the outcomes don't necessarily.
[00:19:00] Colin Keeley: Yeah, I would say they're just, I mean, I said it before, they're bad at their jobs. This is something you come across in like the Midwestern VC, like cities. So like second, third tier cities. And then in Europe, a bunch, where these investors are way, way, way too, risk adverse. So they're never gonna have like the big blowout outcomes.
So the, yeah, they never, they never spot a unicorn in the woods, in their entire life. in the, in the. But. What they do is they invest at like way too low evaluations. And so they dilute the founders, a lot and that kind of just kneecaps the company for life. So the founders are not that incentivized to like perform and then future good investors just won't touch it because of that reason.
And then it's hard to recruit future employees again. So it's like, you've basically. Congrats you own like 50% of the company, but that company is never gonna hit like a great outcome. It's basically kind of dead again. And this is just what you see in like almost all Midwestern cities and E E even in Chicago, this used to be the case.
But you know, as more and more money comes in, there's more like friendly kind of angel or friends and family money. Ore funds like that transforms, and then you have bigger and bigger outcomes, that are more favorable for, know, the founders and the, the investors. They get better outcomes as.
[00:20:16] Brent Sanders: Yeah. It's, it's a fun discussion. Like, your, your point about you. Are they good at their jobs, right. That feels a little, subjective, but objectively, if you set a company up for, a certain, I don't know, crunch in the future and it, like, it seems like it would, it would, if you were doing that, like, for example, if you're a hard bar, let's say you're a good VC you're, you've had great outcomes.
And you were saying about Chicago, which I, I think you mean with like with light bank, like they were arguably good VCs. And the deals were notoriously sort of raw for the, the founders. They would dilute them so far because they were the only show in town, right. So there was all these, kids coming outta big 10 universities moving Chicago, starting a startup and taking, I'm putting up my air, quotes my, a bad deal.
But it's like at the same time, you're also forcing. It's like a forcing function, right? It's like the intention is, if they don't get to where they need to go and they build an okay business, it's an incentive to not build an O okay. Business and rest on your laurels. Right. It has to be an outsized win for, for the founder to, to really do anything, which in turn, I think makes more opportunities for us to pick up. So maybe we should be promoting these practices.
[00:21:31] Colin Keeley: Promoting. So I, I say bad at your job that is completely objective. Like you could figure out what someone is like multiple on invested capital, what their IRR is. And that is how well they performed. So like, light bank performed really, really well. So objectively they were good at their jobs.
Yeah. Like we definitely are picking up some of these deals. A lot of 'em seem to be in Europe where it's like, the original founders own nothing. They got pushed outta the company, some random investor, like the, the local guy in their town with money owns like 70% of the company. And it's like, yeah, I mean, your background is in like running this plumbing yard or something and you should probably, sell it to software.
[00:22:09] Brent Sanders: Interesting. So that's, this has been like a, a wild couple of, of weeks kind of entertaining this idea, this idea of. In my mind of like a studio returning to a studio model with acquisitions like that. That's been interesting. I just think, we're talking about it from both sides and just to be clear, like, I think what's in front of us is doesn't make sense to just, allocate more.
I don't think that, unless there was a, a rare exception that like trying to raise. Venture capital on top of our existing stack of capital makes any sense, like it's, it's just like trying to mix these things is it seems like everyone will be kind of weirded out the, a venture investors is not gonna see what they wanna see our investors.
Aren't gonna necessarily see what they wanna see. I mean, although if we put something on track at a great valuation, I don't think they would complain, but it it's been an interesting sort of deep dive into what are the forms of funding? What are the. The forms of, of doing this and, and the cool part about it.
I go back to like my travels and seeing that a lot of this stuff just doesn't exist in other countries. Like there are European countries, but like for example, in Asia, the concept of venture capital really just doesn't doesn't exist. The, the, the type of funding or, you deal structure just does not exist.
And, and you see that. Hampering innovation. You see that hampering, economic development in a lot of ways and, and those countries are trying to fix it. So, we're, we're kind of poking and prodding, but all in the spirit of like, this is all good, good stuff to have and nice to have the availability of it.
And I think we're getting a, like, getting a little funky in between, dabbling in, in, in both ends.
[00:23:51] Colin Keeley: Yeah, I would say it would be very rare that we would think we require venture capital, like a bunch of capital to really push on something. I, I mean, software companies should be very capital efficient. I don't think, I mean, there's been tons of outcomes that only raise like a small round and we're able to just run from there.
So yeah, take like annual plans up front. You get creative with, contract structures, so you could have the cash flow to continue to invest. and yeah, I don't really see any need that we would need to raise as metric capital on deal kind of going forward.
[00:24:24] Brent Sanders: Agreed. Cool. Well, that was been our, our thought experiment around, an acquisition startup studio and I think we're, we're firmly and I know
[00:24:36] Colin Keeley: yeah.
[00:24:36] Brent Sanders: Anything else going on with you that over the last week that you wanna talk about?
[00:24:39] Colin Keeley: I moved, so that's horrible. I recommend it to no one don't ever move. Just stay where you are. It's not worth it. But, yeah, it's nice. Got internet got moved in. Got my mic set up. So I'm off to the races.
[00:24:51] Brent Sanders: yeah, we were just doing the math. I've moved. I think about 10 times in 15 years when living in Chicago. Like just my wife and I, for some reason we get, we get a bug and we get it down. It does force you to, to clean out the closets, clean out, all the accumulated junk. But yeah, I think, I think we're done.
I think we're absolutely done moving. We've moved into a house and after that last move with kids, it's just like, no, probably not until they're 18 sell this house and, and move on. So yeah, I, I agree with you. So you're still in the point where you gotta.
[00:25:24] Colin Keeley: Yeah, still unpack. And I should say we had movers too. So we had three guys one day, two guys another day, but like, I don't know. I'm like incapable of just sitting on the couch and being like, all right, move this thing here, move this thing there. So I'm like right. Alongside them, moving everything. My body is just so sore.
But yeah, yeah. Still unpacking and everything.
[00:25:42] Brent Sanders: it's done. How's the new neighborhood.
[00:25:44] Colin Keeley: It's cool. It's different. So I moved like three miles north chicago is like the neighborhood, more like, yeah, old 1920s kind of style buildings, which is cool and all new restaurants, super close to the water. So yeah, I really like seeing the water.
I mean, it's just awesome. Not that I was far from it before, but now I'm, super close to go to it every day.
[00:26:02] Brent Sanders: are you a runner?
[00:26:03] Colin Keeley: No, I'm far too big to run. I don't think anyone in my size should run.
[00:26:06] Brent Sanders: Yeah. Yeah. That's what I figured. But that Lakeshore path, I, I hate running, but I actually got into it. I used to, in one of the many houses in Chicago, we, we live right on lake shore, at add. And so we could, hop onto the lake shore path, go running. And it, it really is. One of the coolest parts of Chicago is, is just being on the lake shore path.
It is weird as I think about it, that there's a highway running up and down it, but that's, I guess just part of being in the Midwest, we gotta have a good, good vehicle priority for, for everything, but, enjoy it. Yeah. That that's awesome. I mean, the lake is, is by far the best feature of, of Chicago.
[00:26:39] Colin Keeley: It is awesome. Like people that aren't from here, like, I don't know if they appreciate it. It's more like Barcelona or something. Like, there's not that many huge cities that are actually on the water and, we have pretty awesome water here. Although the highway on the water lake shore is the dumbest thing in the world to me, like I just, if I like ran for mayor, my like, Platform would be, we're gonna turn this into a park, like no more, reserving the best part of the city for cars to race by 60 miles an hour.
I mean, it's super convenient for the drivers, but they could also, figure out another way to be for the people that live in the city.
[00:27:09] Brent Sanders: Yeah, I would agree with that. I. The best time that I've ever had biking in the city is, they do bike the drive where they shut it down and let you ride your bike on it. And man, if they just turned into a bike path, it's too bad. It it's, it is a ma major, major artery. And, but we'll, we can get into Chicago in, in transportation infrastructure another time, but it, it would be so cool if they just did away with that and turned into a beach, just made the park bigger.
Maybe people would be a little bit HAPPI.
[00:27:37] Colin Keeley: Yeah, for sure other cities have done it. I, I imagine it happens in Chicago sometime, but maybe it's like when driverless cars are super common and it's, 20, 50 years out, but it's inevitable. Like it's just an insane use of real. But on that note, we could talk about city planning on the next podcast.
[00:27:52] Brent Sanders: sounds good. Yeah. Stay tuned for that one.
[00:27:54] Colin Keeley: Yeah. All right. Take care.
[00:27:56] Brent Sanders: Thanks for listening.