SPEAKER_01 0:02

Welcome to the Future Adventures podcast. I'm Skelly McClary. Today's guest is Andrew Ackerman. He's a zero entrepreneur venture investor who has spent the last two decades advising startups of accelerators, adventure studio, and corporate innovation platform. He's invested in more than 70 startups who previously helped build Dream Adventures, Urban Tech, and Prop Tech platform, as well as Reach Labs for second-century ventures. He teaches entrepreneurship, writes extensively on venture capital innovation, and recently authored the Entrepreneur's Odyssey, a story-driven guide to building startups in the real world. Andrew, welcome to the stage. I'm super excited to uh to have you on the pod and talk about your journey, but also I am hearing that you're starting something new. So why don't you take it away, kind of tell us who is Andrew and what you're cooking?

SPEAKER_00 0:57

Sure, sure. And I'll let you choose if you want to save the big reveal for the end or not. Um, no, your intro is great. I've been doing this for a long time. Been on, you know, there's that phrase like both sides of the table. I think I've been on like five or six sides of the table over the career. It's a round table for you. Yeah, no, we have to have sides, everyone's got to have sides. But I've been on I've been in a lot of the chairs around the table, so it's given me a kind of uh interesting and fun perspective, sometimes a little cynical, but you know, always with a smile.

SPEAKER_01 1:30

And so how like walk me through kind of like your journey. How did you come to doing what you're doing? And like what is the what is the passion line?

SPEAKER_00 1:40

I feel like my resume should come with a big stamp on top. Do not try this at home. Uh it only really made sense in retrospect, but it was kind of meandering. So, you know, when I got out of business school, uh, if you said you're an entrepreneur, they're like, Oh, poor guy, unemployed. It didn't this whole culture of entrepreneurship exist? I mean, it was, there were always some people. But like, what are you doing in business school if you want to be an entrepreneur? You don't need to go to school for that, just go do it, right? You know, your uncle will teach you, dad will teach you. Uh, now it's very different. Now you have whole centers of entrepreneurship as part of the business school program. It wasn't like that. So coming out of uh, you know, I went to the University of Chicago, so before it was called Chicago Booth, you know, there are two doors. It's like, you know, you got consulting on this side and you got i banking on that side. And if you're interested in marketing, you came to the wrong school. You should be at Northwestern. Uh, I know I didn't want to do i banking, so I went into consulting. And by the way, you want to go full circle? My daughter is now a soft, and she's looking at uh consulting for her summer internship. So this this summer she's got, but she's already looking for Nest Summer. If any of your listeners are like, Oh, I like consultants, I can hire a couple of them.

SPEAKER_01 2:54

Um you have any influence in terms of what she's choosing, you know, it was all on her own.

SPEAKER_00 2:59

Yeah, you know, like it's very interesting for for you and and any of the listeners out there who have kids that are at that stage. It's a really cool um coming back, right? It's where when they leave, all of a sudden, like a flip switches, and they're like, God damn it, he might actually know something. Uh so we're having a very it's a very interesting phase in our relationship, yeah. Where we vacillate between dad, come on, and like, you know, so what do you think about this? Did I write my follow-up letter nicely or not?

SPEAKER_04 3:29

Yeah.

SPEAKER_00 3:30

Uh and I'm I'm really kind of enjoying it. Um, you know, but I digress.

SPEAKER_01 3:36

Yeah, no, I I I I hear you. I have two girls and uh two and fourteen. And for them, oh we got three uh three girls, yeah. Three girls, two girls, uh where girl dads. Um it's I'm just kind of going with the flow most of the time, just trying not to offend anyone. Um I hear you, I hear you. Um so so you went to University of Chicago. Um, what what what draw you I mean to your point? What um it it's a similar background for me. Like I went to university um and then pursued entrepreneurship. I actually finished university in three years and then started my first company uh in my third year university. But to your point, it's not a common path, at least wasn't a common path. Now we celebrate entrepreneurship, but back then it wasn't. So kind of like what prompted you to go down this path?

SPEAKER_00 4:32

Yeah, so it's interesting. So both my grandfathers were entrepreneurs, small business, uh one owned like coffee shop, not coffee shop, sorry, candy shops. We didn't have coffee shops back in the 70s, so candy shops or stationery or toy stores, and the other one had done everything from zip ho lighters all the way up to designing like travel insurance products. So, you know, they were um sort of role model for me, but they also died far too young. Uh so they weren't around when I came out of business school. And uh, you know, my dad wasn't uh a doctor, so like it wasn't that's not a very entrepreneurial mindset by and large. So when I came out of business school, the idea of consulting appealed to me because I could find out like I can be on a bunch of different projects, work with a bunch of different industries, maybe find out something that speaks to me. Uh, and it was okay, they're very smart people. I enjoyed it, it was very good finishing school for business school, but uh you know, it wasn't really resonating. And you know, sometime in 1999, I was on this project, and you know, the the internet was new and shiny, and we built this with the help of another actually built it, uh, intranet application for two of our clients who are merging so that they could share data without contaminating the other teams. Because you know, if you share all that data and then the antitrust people say, Yeah, no, you can't do that, uh, anyone who knows the information from the other side can't go back to their regular job anymore. So it's kind of career limiting. So that's to be on that. Uh, so the system we built actually solved that problem because no one got to see anyone else's but us, and we could kind of push a button and then see pro forma financials. And if you remember the internet back in 1999, push a button meant push the button, let's go out to get some curry, and as we were in London at the time, and like uh in um my my blanket for the neighborhood, it's uh coven gardens, and then come back 30 minutes later and you get your results. Yeah, but it was enough, right? I looked at it and I'm like, that's it. This didn't exist four years ago, but it exists now, and this is where I need to be. So within probably six or nine months, I'd uh resigned from my position as a consultant, I'd moved back to New York. Yeah, I took a job at like Kaplan Test Prep because they needed help, they needed a consultant internal to help them get on the internet, and then within nine months after that, I was at my first startup.

SPEAKER_01 7:05

Very cool. Was the first startup uh one that you started, or did you join somebody else?

SPEAKER_00 7:12

Um so I'm one of the first three founders, though they had started with the they had come up with the idea before I joined. It was uh what we would call now SaaS or software as a service for some reason.

SPEAKER_01 7:24

Yeah, yeah, it was a wild time. Um my second internship in university was in with it was in '99, uh, and it was with a company called iMagic TV. It was the first company to to do digital television over copper wires. No, I think I knew one.

SPEAKER_00 7:47

Um yeah, there's there was a lot of like waiting for that hourglass to keep turning over.

SPEAKER_01 7:52

Yeah, I mean, I remember like in the lobby we had uh plasma screen at that time. Plasma screen TV were with a rage, and one was ten thousand dollars, like just insane. Um, but like I mean, we're talking 99, the ability to skip commercials, the ability to record. This was like very innovative at the time. Now it's it's kind of a standard feature of any kind of digital television. Um, and it was a really interesting time. It was my very first startup. I think we were, I can't remember, we were probably at about a hundred and fifty employees. It was backed by one of the telcos uh and battle, which became a line, which a line got bugged by Bell Canada. Um, it was a wild time because we were really hoping and praying we're gonna go public in 2000 came along and September 11. And toop, toop, toop, toop, everything just kind of went down. Yeah.

SPEAKER_00 8:45

So we actually had a term sheet from a uh a VC whose offices were in the World Trade Center. So the person we spoke to whose final wasn't there that day, but our term sheet and the VC behind it literally evaporated that morning.

SPEAKER_01 9:03

That's crazy. I still remember to this day, like where it was when it watched it on TV.

SPEAKER_00 9:10

Like it just very much so, and I still remember it was if you were in New York, it was this clear blue sky, not a cloud in the sky, crisp all day. So anytime I walk outside and it's like that blue, and it's about you know 65-70 degrees, and like that's deja vu.

SPEAKER_01 9:28

Yeah, yeah. Crazy. And and so you you you joined two other co-founders, you guys worked on the company, kind of what what was the the outcome? What was the success of the company?

SPEAKER_00 9:38

Yeah, we sold, right? So it's actually um, yeah, no, we we sold uh well, let me rephrase that. I got bought out in OA. Uh, we had gone through a whole process uh to sell it. Uh the founder was like, yeah, that's not high enough. I'm like, I think it's high enough, then you should be thrilled to buy me out. And after some hemming and hawing, we ultimately agreed to like a year where I found a successor and trained them up and so on. Uh the company then went on for another five or six years, uh, and ultimately was acquired by a private equity fund who'd also done other registration systems, uh, and as part of putting together this um portfolio. And then a couple years after that, it was finally sold. So you know the company was sold a little bit after I left, but I had my exit um end of 2008.

SPEAKER_01 10:28

Nice. So first title, first exit. Uh that's fantastic. Um then then what what carries on in terms of the journey?

SPEAKER_00 10:39

Well, that that's actually where um one of the first life's lessons I learned. Uh this one's not in the book, but like I had been so head down, like heads down, like I'm the COO, I gotta make everything work, um, that I didn't really spend a lot of time um networking or promoting myself and getting out there. So uh you know I exited and then I thought, well, okay, I'm an exit entrepreneur now. Like, you know, ideas should be like not ideas, but like authors should be coming to me. And I'm like, yeah, we don't know who you are. Plus, also I exited like this was the end of 2008. So if you thought you know 2001 was bad, like 2008, welcome, we're back, right? It wasn't a great time. Um, so here I am like through 2008, like looking for stuff, and like I realized like, oh, I should have been building my profile and my my network a year and a half ago already. Uh so that was one of my first big lessons learned about uh the need to like you know be thinking two or three steps ahead and to always be building my personal brand.

SPEAKER_01 11:45

I can't emphasize this enough. Um, just for context, future ventures is a boutique capital advisory firm. Um and so one of the two primary reasons why companies or founders come to us is like they're either stuck on the growth side or they're unable to raise money on their own. And um, we're like, well, what have you done in terms of building up building out your brand, getting the investment community to know you, or getting other uh people in the ecosystem to know you? Um have you engaged, like have you developed an investment relations strategy? Are you executing? Because like if you're trying to just raise money off cold emails, it is very, very hard. Very hard.

SPEAKER_00 12:32

Don't waste your time. And this is stuff I cover in like the last third of the book about how to raise the round. Um, you know, the warm intros are key, right? So hopefully you've been building them along the way. I tell all my founders, I think this is I don't remember if this particular piece is in the book or not. You know, you ever hear a founder say, you know, we're not fundraising. I'm like, that's cute, you're wrong. You are always always the difference is am I spending 10 to 20 percent of my time kind of cultivating these relationships and then 80 plus percent of my time on the startup, or am I spending 80% of my time trying to get that money because I actually do need it right now? And then 20%, you know, making sure the founder the startup doesn't fall apart while I'm busy fundraising.

SPEAKER_01 13:14

Okay. So, Andrew, you've been a founder, you've worked, you've been an accelerator operator, you've you're an investor, you're an adjunct professor, uh with the National Realtors Association, Institutional VC, kind of like which role gave you the clearest understanding of how the startups actually succeed?

SPEAKER_00 13:35

Uh, probably the accelerator, to be honest. Um, like listen, at every stage, at every stage you learn more, and you also learn how little you really do know. So after the first startup was a success, I'm like, okay, I kind of get this. And then you know, I started I had started to do some angel investment along the way, and then start seeing like all different models, and you're like, well, that's very different. I don't know what to tell these guys.

SPEAKER_04 13:58

Yeah.

SPEAKER_00 13:59

Uh, and then like you think you got some startups that are going to do really great, and then like they tank. And I got lucky, my first startup did very the first startup that I invested in, my first angel investment did very well. But I realized in retrospect that I I didn't invest wisely, like I didn't really know what I was doing, I just got lucky. Uh, and you know, the curse there is if your first investment goes, well, now you're hooked. So I had to learn what I was doing wrong and get better at it before my luck ran out. So, you know, once you start going from say founder to angel investor, you realize that like what you learn with your startup, that's only pieces of it, right? It's like only knowing how to play one hand in poker, but a lot of other hands. Uh and then when you go from angel to like a VC or an accelerator, an accelerator. So I'm like, I should probably define some terms here, right? So an angel investor is just you know, you're investing out of your own pocket, right? If you see a good startup, you got the money, you can invest. If you don't see a good startup that month, like, hey, you don't have to. Yeah, no big deal. When you're a VC, a venture capital fund or an accelerator, which is often a structure like a VC behind the scenes, but has like you know, regular programming that begins and ends, you don't have the luxury of being like, Yeah, I didn't really see anything this month, let's wait for another. You actually have to have you know, you need to deploy the capital at a certain uh speed. You need to have like I need 10 startups in my cohorts, I gotta work backwards. I gotta look at, I kid you not, over a thousand startups to come up with like 50 or so I want to interview, and hopefully 10 that'll actually take into my program. Yeah, so I went from like, oh, I saw two good startups this month, that's awesome. But like, yeah, I have two months to find to look over a thousand pictures. Yeah. So, you know, then I realized like, yeah, I knew nothing about that. So I don't learn how to do that.

SPEAKER_04 15:56

Yeah.

SPEAKER_00 15:56

Uh, and then I spend like once we have startups in the program, I'm working with 10 startups, I'm meeting with them for an hour a week, every week, sometimes more, just really running them through this this this um I won't call it boot camp, it's not bad, it's pretty bespoke, but pressure testing and stress testing, every link in the channel that makes up their startup. More I find stuff's weak, we work together to forge something stronger. Um, you know, then all of a sudden, like some of the things that I learned for myself, I was able to start generalizing them. Uh, and more importantly, I was able to start thinking about like I have the knowledge, but I'm not getting it across effectively. How do I get the lesson across better? How do I get a starter to realize this is really what they need to do? Um, so that and we can talk more about the you know the evolution beyond that, but those were like the like the big step level, you know, like oh my god, I guess I don't know what I'm doing, but now I'm learning parts of my life.

SPEAKER_01 17:01

So I I mean after having exposure to to this many companies, and um you you can't help but develop pattern recognition. So from from what you've observed, what consistently separate companies that scale from the from the ones that stole? Kind of like what are the patterns that emerge that you say, huh? This is a company that I think is they is going to be very successful.

SPEAKER_00 17:30

So I'm gonna give you a non-answer first, and then I'll give you a specific answer. Sure. Okay, or a two or three specific examples. So I talked about the startup as a chain, I use that analogy right uh a lot. Um like let's say you've got the startup as a rope and a couple of strands refrayed, like enough of them are strong, we're good to go. Doesn't work that way with the startup, right? If one link is bad, you got nothing, right? So you have to think about it that way. So on the one hand, when you look at it, um, all the startups that fail, like it's a different link in the chain. Or you don't know, maybe the market size is too small, maybe you know the team sucks, right? It's a different link in the chain. Uh so they're all kind of different. Now, that's my non-answer, but it's true, right? So you have to understand like all the links in the chain. Where pattern recognition starts to come in is where I can look at a startup and like, I gotta test this link first, right? So when you're first starting, it's like any sport, right? You have to break it down, like understand the individual motions and like train your muscles to do it, and you start getting well, it becomes instinctive a little bit. So let's say, for example, uh I'm dealing with a startup that sells to architects. I happen to know there's something like 200,000 architects in the US, and depending on what you're charging, it's very likely that that's not a large market by venture standards, right? You see, we're looking for billion-dollar total addressable markets, like you gotta charge a lot for that product to just 200,000 people. So I know that that kind of startup, I gotta go look at the chain, the link in the chain that is the total addressable market first, because if that's broken, I don't have to look at anything else. Yeah, I don't that I don't get bonus points for figuring out five other links that are broken. I need to be like, This is broken, go back, say hey, that's why. Thank you very much. Good luck. And then I need to use my time better by finding and looking at other startups. So that's what pattern recognition starts to come in. Um, I gave you a non-answer, I gave you kind of a specific answer. Yeah, you want me to go even deeper?

SPEAKER_01 19:37

I I I would love. I mean, um, I often ask this question of uh of my investor guests because uh I'm I'm curious, and and and and I I appreciate the different nuances that could exist depending on on what the investment thesis is, but I'm kind of looking to to get uh investors' perspective around what they see or is are there nuances? Because everyone can talk about well, I'm looking for the size of the market, the opportunity, the the team, like but kind of like but what specifically would make you invest in a company versus I'm gonna wait out.

SPEAKER_00 20:12

Yeah, so there's um there are a couple of ways to look at it, right? So one of the things that a lot of founders don't appreciate, uh maybe don't believe it until they're on this side of the table, is just how often we will see startups that are virtually identical except for the logo. Now you're laughing. Later in the cycle, it happens a lot. There's a lot of imitators like, yeah, okay, you know, you see a blockchain startup now. Of course they're copying, they're late to that party. Yeah, but what they don't realize is even like at the very beginning of that wave, they're already seeing it. So let me kind of break that down and explain why that happens, right? So there are underlying problems, whatever it is, it's do this, um, and they're to a certain extent uh insoluble at the moment, and then something changes, and it could be technology, now we have blockchain, now we have AI that's like available like for the common user. Machine vision now works, speech to text works, whatever it is, it's usually technological, it could be regulatory, but they changed the regulations. Now we can do this, we couldn't before, now we can't do this, right? Um, those are kind of I call them discontinuities. Those are like now is very much different than the way it was before. Now, what happens in those discontinuities is some problems that were very painful but were insoluble are now suddenly soluble. Now you can solvable, I should say, not soluble, solvable. Right? So uh wow, it's like the gates just opened up. Now you might think I just figured out the great opportunity. Here's my startup. You have to understand there are 10. If not hundreds of thousands of hungry entrepreneurs out there. Some of them are looking at that same problem. And when the ice breaks, they're like, I just figured out how to solve it. So that light bulb goes off in a couple of different places. Sometimes, you know, a couple dozen different places, because what was insolvable is now solvable. So and sometimes their solutions are different, but sometimes they're actually pretty close to each other. So it's not uncommon, especially when you, you know, like me, if you if you focus on a certain industry, so people come to a certain type of startups, you end up seeing a lot of a similar deck. So I didn't appreciate that as a founder. Uh when I appreciate it, I don't mean like I resented it. I mean I didn't understand it fully. Uh, but I get that now. But what that means is when I look at the investments, you know, sometimes it's a genuinely new solution to the problem. Wow, that's interesting. These guys have figured it out before anyone else has. Now I have to ask myself, is that true? Or have I just not seen the 12 other people who are toppling the problem? But that's okay, right? That means that, I mean, assuming I'm on top of my job, that means that this is pretty cutting edge. That means that it has a good answer to the question, why now? Right? If there's no good answer to why now, it's like whatever, there's a lot of people ahead of you already, or you know, this isn't the solution that works. They've tried it and it's failed, and I'm not gonna give you money to fail the exact same way again. But at least that means like they're in the running. And then the question becomes do I believe that this is the team that's gonna do it? Like, I don't believe in fighting fair. I want to like I want the heavyweight fighting against the welterweight, like okay, that's not what I'm backing. I'm not backing fair, I'm not the winner in this one. Yeah, I'm diving into the team. Sometimes it's the experience, sometimes it's the sales ability and the connections, but it can be other things. But I just want to feel like there's something in that team that even among like the dozen of people, dozen of startups that are coming up with this idea right now, yeah, these are the ones that are going to eat the other 11 startups much. So that's how I look at that.

SPEAKER_01 24:22

Understood. Um, do you primarily invest in real estate and prop tech?

SPEAKER_00 24:27

Yeah, so not the real estate itself that I don't do, but I'll invest in startups that are involved in the real estate or construction process. So anything from owners and developers to general contractors, architects, uh uh, you know, subcontractors, uh, you know, you know, anyone involved in that uh process. So if they sell for perhaps software to that area, or if they've selling hardware or a mix of the two, as long as those are the customer base and it deals with like building or operating buildings, I'm interested.

SPEAKER_01 25:03

What um what are you seeing in the space that you're really the most excited about? So if you're to project five, ten years out, kind of like what do you think is going to win? Is it gonna be software, is it gonna be hardware? Like, how is the real estate industry evolving? And and yes, I understand it's not the physical underlying asset, but anything that's supporting the underlying assets.

SPEAKER_00 25:24

So you may find this surprising, but I actually I don't I don't love that question. I'll tell you why. Most of the people, when they get asked that question, either their answer is so blindingly obvious, it's like, yeah, okay, fine. I've heard that a zillion times before, or it's kind of out there and thought provoking, but like you know, 99 times out of 10, they're wrong because like we're predicting the future. So it's um it's kind of a tough question to ask and be interesting. Uh, but I'll I'll do my best, right? I'll do my best. So uh specifically with uh real estate.

SPEAKER_01 25:58

Can I just jump in? Uh sure. I I want you to be comfortable with the answer. So I'll rephrase my question. What areas are attracting the most investments right now?

SPEAKER_00 26:08

Oh, that's AI, but that's a boring answer, right? Yeah, everything's AI these days.

SPEAKER_01 26:13

Even in real estate, the words are.

SPEAKER_00 26:15

Oh, yeah, every everything is is everything is AI these days. Okay. And it's not AI, it's robotics, right? But it's tricky. So actually, let me let me drill into it because yeah, there's interesting implications here. Um actually let me give you something that maybe the casual listener is not aware of. So we when we think about like building a building, sometimes we think about it, it's like it's kind of like a manufacturing plant, except what they're building is a building, right? You have a lot of people with heavy equipment, you know, and hard hats and you know, dirty, you know, dirt under their nails, uh, and they're they're creating something physical, right? In this case, something physical that'll last a century or more, yeah, unless somebody screws up. So uh we tend to think about that analogy, but it's actually an analogy that's been holding the industry back. There's these uh these comparisons between manufacturing and construction and manufacturing's got really nice productivity gains. Yep, it's looking good, and they look at construction and it's down, like you know, we are less productive now than we were 50 years ago in construction. I argue part of that's because we've taken those gains and like fewer people dying, right? Say it's a lot safer, but straight productivity is lower, and uh, I think the problem is we're looking at it the wrong way. So let's say you, Maxim, owned a factory, yeah. Everybody in your factory reports to you, you pay them salary, right? You control all of that. Anything that comes into your factory, you ordered. Anything that leaves your factory, you're selling, unless it's trash, they have to pay someone to haul it away. But even then, you're paying for that. Yeah, none of what I just said is true for construction. Let's say, Maxim, you're the owner, right? Or the developer. 99% of the people who work on that building don't work for you, right? So you hire an architect, yeah, they have different incentives. Then you put it out for bid and you get a GC, they've got different incentives, and even the GC, they're barely 20% of the people, if that on the job site, because most of the people that work for them are subcontractors, they have different incentives. So if you want to try to get someone to use the same software, you have to have five or six parties to compete, and they're like, I'm not gonna use your software, I'm on three other projects, I have to use three other software packages. The hell with you, I'm gonna do it my way.

SPEAKER_01 28:45

I I I get that, I get that. And um I I guess my my question then, my follow-up question to this is uh a few years back, we we used to work with a prefabricated home, and I'm not talking mobile homes, I'm talking prefabricated high-end homes, uh, primarily second residences. I'm like lower cost of production, higher quality, uh, lower wastage, lower carbon footprint, um, like faster delivery. I'm like, why hasn't the prefabricated market taken off, especially given the demand for housing, both in Canada and the States?

SPEAKER_00 29:24

So demand for housing uh sometimes is stymied by zoning. So that's an issue. Like, why hasn't it why has demand not been met? It doesn't matter whether it's traditional construction or or modular, there are other barriers in the way. Um modular is actually not new, right? I didn't I was kind of astounded to to find this out. But after World War II, I think the majority of the houses that were being built and came back from the world were modular.

SPEAKER_02 29:52

Yeah, right.

SPEAKER_00 29:52

And they were a little cookie cutter, but and I think that's part of the issue. What happened was it wasn't that modular got worse, it's that what we call traditional, meaning kind of customer bespeak, the cost of that just got better. So it got to the people where for the same money I could have, I'm talking about single family homes because modular for like large buildings, that's a little different, but you know, I could have the same money, I could have my house my way, right? I could look different, not like every other house on the block. You know, that was like a no-brainer. Uh problem with different modular, depending on you can modular units or you can do modular full modular, in part is supply chain. And so if I'm in a if I'm building like a large office building and I want to get modular wall panels, uh, if my supplier is late, the entire project grinds to a halt. So that kind of scheduling risk is very big. Uh and modules just not that um not that robust yet. In other countries, it's a little bit more, in certain sectors, it's a little better. Like, for instance, if you were in California and you wanted to put like a mother-in-law unit in the in the back of your yard, there are actually some I mean, though there's been some big failures there too, but I mean that that's an easier use case. Um it's been tough to get any to take off. And the other thing is I've looked at a lot of them. Uh, remember we get back to like, is this the team that's gonna win? Yeah, they all kind of look the same.

SPEAKER_04 31:23

Team Okay, okay.

SPEAKER_00 31:25

So, you know, I'm like, I don't know which horse to back in this race. And when I look at the like their go-to-market, it's all the same, right? You they're not it's not that they're wrong, it's just ideally I'd like a company that I look at their go-to-market strategy. I'm like, wow, that is as clever as the product itself, yeah. Right, they are zagging where the people are zigging. This could really work, yeah. I didn't see that. Uh never chased the bet on module.

SPEAKER_01 31:54

Yeah, interesting. Um you mentioned a lot of the capital at the moment in the real estate industry, where it's always kind of flowing into AI. What have you seen if you're like just absolutely full of excitement, jazzed up about kind of like what's coming and how that's gonna shape the industry?

SPEAKER_00 32:14

It's kind of funny. Like, you know, a lot of the people in real estate and construction are a little conservative. I and listen, it makes sense, right? If I'm building software and it breaks, I can send a patch, right? If you know my software company goes out of business, I'll find another software vendor. Yeah, yeah, that doesn't work with buildings, right? You know, if like, oh, that new concrete we tried turned out to be a bust, like that's a problem, right? If I have a new elevator and the company that, you know, whatever the software that runs the elevator is gone, yeah, like that's mission critical. So they tend to be a little bit more conservative, the customers in my sector. Um, and with AI, you know, they're in this kind of hope and fear like combination right now. They realize everything's changing, they don't really know what they're doing, and they're just trying to experiment. Some are doing better than others at it, but their inherent conservatism, like a lot of them, like for them, AI is Microsoft Copilot. Yeah, and some of them are even like in the in the construction side, they're pulling back, right? So they they just realize sort of um everything they upload into chat GPT or Claude becomes part of the bigger LLM. Uh oh, we can't do that. So they've taken it out of their people's hands. Now they may be overreacting, but if you think about it, use different industry. If you're a law firm and you put anything into it, you've automatically violated attorney client. So, and and forget about that's just when I'm uploading files, I'm trying to do things manually. If I try to implement AI that's in my workflow, that's automatically scanning the emails coming in and out, and like doing really interesting stuff, like forget about that. So there's a there is definitely a we have to figure this out, but also some you know, some very legitimate fears here. Uh, on top of that, uh, everyone who used to think, oh, it's SAS, SAS is the best way to do it. Now AI is kind of killing a lot of that because now, you know, on the lower end of the market, I can whip something together, single quotes, it's not that easy. But for the people who have more like you know, uh elbow grease than money, yeah, what really matters, they'll whip up something that works, you know, they used to be well enough. Well enough used to suck compared to the software, but now well enough is getting pretty damn good. Right, and then you get a lot of people think, well, I can go build like this SaaS product, and I can start selling it at a 10% cost, which is maybe true, except now like there's like no differentiator, there's tons of new products coming out that they're not great investments for me, they're great for the user, maybe. So we're in this really disruptive area where uh like the customers are kind of looking at they're not sure what it is, but they know that whatever they're doing, like you gotta either be generating top line revenue, which is a little harder for them to find, or you gotta be ripping cost out, which you know that they seem to be figuring out. Uh but again, they don't kind of know what they really want to do. So it's it's a very interesting, exciting, scary, all those adjectives time right now in the real estate and construction space.

SPEAKER_01 35:39

I hear you, I hear you, and and um a lot of the things resonate. Um we uh we internally, for one of our portfolio companies, build a mini RP within three months that does everything that they need to do. Um it's so good that now we're thinking about turning into a product. Um, but uh like again, we have a dev team, so it's not like we just live coded in our cursor. It's like we we did proper proper databases, we react and next.js and like proper proper infrastructure, it's intended to be sort of type two compliant, so like security risk controls, everything is uh incorporated, but it's become affordable, it's become approachable. Um, so we're constantly if the work that we do, it's kind of like um did you say that the cobblers uh kids work barefoot? We we eat our own child, like we uh optimize everything that we do, and then portfolio companies they have to do this, and then um that it in my mind can be I think you said it you either grow revenue or rip costs out, like that's really the only way that you can drive a sustainable business. What are you seeing now in the real estate industry is is opportunities for people to either grow the top line or drive the the the bottom line now?

SPEAKER_00 37:01

Um sorry, I thought you were gonna go slightly different uh direction. By all means, veer off. Yeah. So I was gonna tell you, like it, and this is something that you know I am one foot in, one foot out. So I I was approached by an old friend, uh, and he's like, So what are you doing these days? And we got to talking about what he's building, and I've been working with him and his team now for almost two months, and you know, we're we're in the process of making that kind of more official and coming on board. So the the interesting thing when does the official announcement come out? Uh I'll let you know, and you can add it to the show notes when I have it. Yep. Awesome. So, and that's also why I'm being a little cagey about the name, but I'm gonna give you the idea. So, back in the day, meaning a year ago, uh, if you said you were a tech-enabled startup, it's not really venture back, right? So for the guys in the artist are like, well, that sounds like words I know, but I don't know what that means. Yeah, it's like instead of selling software, if you're just like, hey, I'm a company, I do this work, I built this own tech for myself, it makes me better at it. Um, you know, it's generally not the kind of thing that a VC loves because it scales slowly. And the underlying economics aren't software economics, right? Software economics are uh zero cost, like 20 more people using it, or 2,000 more people using it.

SPEAKER_04 38:25

Yeah, yeah.

SPEAKER_00 38:25

Like service businesses, like you gotta sell, you gotta put bodies on it, like you know, so you're getting 60% margins instead of you know 40, or you're getting 40 margins instead of 20. So you're better, but like it's a different kind of animal. So we normally be like, Yeah, I'm not interested. But I think in real estate, especially, but I would argue in a lot of other places, um, there is another play to have. So there are, and this part's I think I think this is public. Um, I believe that General Catalyst bought Amex Travel. Like, I didn't know if any of you knew the Amex travel. I don't know if you knew this, but there's still travel agents out there, they're just mostly in the business. But they bought it, and why would you buy like you know, that kind of sleepy little business? Because they realize that the potential to deploy AI in that business and to change economics is so great. Instead of trying to sell software to them, yeah, let's just own the customer, rip the cost out, and capture all that all that benefit. So there is an opportunity uh to really just take over the large players if you have that kind of money, yeah. And uh employ and do your own kind of internal AI, and the value is big enough you don't need to sell it. So the project that I'm working on, the company that I'm kind of working with right now, it takes the same approach within the whole kind of construction process, uh, and it solves the thing that I talked to you about before, which is like you know, you don't those people don't work for you, those people don't work for you, those people don't work for you. Yeah, so instead of dealing with that, yeah um, we build we're actually buying a bunch of those service companies, and they're all kind of small, and um, but we're we've built the AI tools that apply to all of them in-house. Oh, nice. So we're a bit like a holding company, almost like a private equity fund that owns a bunch of folio companies, but we also hold the technology at the parent level.

SPEAKER_01 40:28

And as we bring So you do in a value chain integration roll-up where you like, yeah.

SPEAKER_00 40:32

So we may we may we may not even roll them up, right? So if if we own 10 owners' reps, they they might just continue to operate under their own brands in different parts of the country or in different sectors, but behind the scenes we've deployed our tech, so the margins are much better. So it could be uh a holding company with a bunch of different brands, it could be consolidated. Uh not to be a little morbid about it, but like funeral homes are like that. Like you think the funeral home is like this mom and pop or this you know, father and son local business, I think like 80% of them are owned by corporations behind the scenes, yeah. So we can do that, but the key play is it's kind of like private equity, except instead of economies of scale or whatever else, we're using the AI that we've built to change the economics of the company, and that works in the construction world because, like, hey, don't tell me what tech I want to use, right? I will use my own tech. That's fine, we'll just play well with you. We're just focused on doing our job better. So, as far as you're concerned, Maxim, you just keep doing what you're doing. Yeah, you're just gonna find us like better and faster and more fun to work with.

SPEAKER_01 41:42

We um uh one of our companies relies on logistics heavily, and so we're actually building product for this because um it's just the process is so antiquated. I mean, so antiquated, and every freight forward or curry or shipper has their own processes, and some of them don't have anything, some of them are on EDI, some of them are on have API, it's just old, old school. Um, so what we're doing with them is part of the customer discovery interview is we're not forcing them to use our platform. We're just saying, how can we make it easier for you to do business with us?

SPEAKER_00 42:21

Yeah, so it becomes a little bit more like a consulting sale.

SPEAKER_01 42:24

Absolutely, absolutely, yeah.

SPEAKER_00 42:27

But actually, it's interesting as you mentioned it to go back to one of the questions you asked earlier. Yeah, like some of the companies, like some of the big red flags that I see when you know 12 different companies that are similar come to me. Because if I, when I'm talking to people, I can come up with you know four or five or a half dozen or a dozen things that they could do right now without getting my money that would help de-risk the startup. Like that's a problem, right? Like, you don't come to me until like you don't have any other way to like reduce the uncertainty. And customer discovery is one of the big ones. So for example, um, and I use this one in my book actually. Uh, you hear of the index card app or the index card website?

SPEAKER_01 43:11

No, it haven't.

SPEAKER_00 43:12

Okay, I I may have made that term up, but it's not a um, you know, I it's not an actual website. No, I mean it might be. I don't know. You can Google it later, but it's it's a concept that is out there, uh, just not as well done as it should. So let's say you have an idea for you know an app, you know, your tech is just start coding. Like rookie founders, we're just gonna start building or hire someone to start building. Yeah, yeah. Uh, and the problem is like you end up you know building what's in your head in that bubble. It's not necessarily what the market as a whole wants. And then all of a sudden come back later and realize I build all of that stuff, no one touches it, and like I can't get people to use it because I'm missing these four things that they do need. So the index card website is kind of a very simple but powerful idea. So it's number one go to staple. And buy a pack of index cards. Quests maybe. Then go get yourself a pen. I like to steal them from the bank. They're free, right? Um, so that costs you nothing. And then you take your pen and your index cards. I don't have that as a visual, and you draw each screen on an index card.

SPEAKER_04 44:20

Yeah.

SPEAKER_00 44:20

Don't worry, be sloppy, right? Because the goal is not to get people hooked up on the you know, the look, oh, it's a very nice photo. You want them focused on the functionality.

SPEAKER_04 44:30

Yeah. Right.

SPEAKER_00 44:31

So you're sketching it out. It should be legible, but don't worry about you know everything should kind of be where it's going to be. But don't worry about making it pretty. That's not the goal, right? It's a call, it's a wireframe, basically.

SPEAKER_01 44:42

Yeah, you're doing the analog version of Figma.

SPEAKER_00 44:45

Yeah, oh, I'm sorry, better this, better this guy, right? Yeah. And then you come up to your by the way, I use balsamic sometimes for this, but then you come up to your customer. I should do this in person, right? Let's say it's a consumer-facing app, it's easier. You'll say, Hey Maxim, listen, I I'm building this website or building this app. Um, you know, the whole idea is it's basically to do X, one sentence, right? Um, I've mocked up my app on a series of index cards. I would like you to pretend you just downloaded the app and you're seeing the screens. Just interact with it, right? If you're pressing a button, press the part of the index card. If you swipe, do it. You know, don't ask me questions. I'm not gonna be there when you download the app. Yeah, uh, the only thing I'm asking you to do differently is whatever you're thinking, say it out loud because I can't read your mind, right? I just want to watch how you interact with this and what you're thinking, hear what you're thinking, and then just sit back and let them do it. So what you'll notice is right in the example I gave before, they don't touch two-thirds of your site, right? But you didn't have to build it now, it's just like hand and paper. They don't touch it. So then after they've done it, like you can ask them, well, why didn't you touch that? Or you can break character at the end. Yeah, but yeah, I don't need any of that. Well, guess what? You just saved yourself two-thirds of the dev time. Well, they got to a certain point, and they're like, I want to click that, but I'm afraid that if I click that, something will happen. Well, you've learned a lot there, or it's like, oh man, I really wanted to do X, but I can't get to that. Yeah, and then you know you've got to build it, or if you've already built it, you have to make it more obvious that it's there. And it cost you 20 minutes of your time and eight dollars worth of index cards and a free pen that you stole from the bank. And you multiply that by 20 or 30 people or 50 people. Yeah, and now instead of going down a six-month blind path, in a week, you've actually figured out this is what I need to build, this is what I don't need to build. Yeah, super powerful tool. I don't know why everyone isn't doing it. It should be standard, it should be standard in every entrepreneurship class out there.

SPEAKER_01 46:52

Yeah. Um, I I mean, I couldn't agree more. Um it's it's it's like it's like customer discovery is is an anathema for for founders, like like I just want to go and build. Like that's a that's a first-time error. Yeah, exactly. Exactly. Go and figure out is is this a problem that if uh other people are having and and their hair is on fire, or is this nice to have kind of like the other saying is like is this a vitamin or is a painkiller? How big is the problem? How acute is the problem?

SPEAKER_00 47:27

Let's let's let's dive into that. There are actually three dimensions to pain, and I talked this over. So one is I usually did I just you know hit my nail, hit my thumb with uh a hammer, or is it a hangnail, but hair on fire, some idea, yeah, intensity. The second one is prevalence, right? It hurts me a lot. Does anyone else have this problem? So a lot of founders like they just assume that since it's their problem, it must be everybody's and they go out there and talk to people like, yeah, I don't really care. Uh and the third one is frequency, yeah, right? So like college admissions, I went through this. I have two kids who are juniors in high school, like they it's a very stressful decision. So it's like hair on fire times 10. Yeah, uh, and it's pretty prevalent. Like most people in the country do go to college now, but it happens once in your life, so it's tough. Like you really want to score ideally high on all three dimensions. Uh, you can maybe do it with two dimensions, but you just realize that certain things are going to be harder, you know, especially in the example I gave, because it's just not frequent.

SPEAKER_01 48:31

Okay, okay. What um I mean, we we we spent the last 50 minutes talking about kind of like um the entrepreneurial world, but like what prompted you to write the entrepreneur's odyssey and why do you choose this format rather than uh the standard conventional business book, like you know, that kind of like you've seen with I mean maybe your previous answers give me a clue in terms of how you're thinking, but uh yeah, I mean there's a couple of answers, some are kind of deep and some are kind of flipped.

SPEAKER_00 49:05

I'll start with the flip ones first, right? Most boring, most business books are just boring. Like if my eyes glaze over, I fall asleep 10 pages in. It's the same random chipper guy in the Midwest. Uh he's like, yeah, you know, it's like anecdote, anecdote, anecdote, name drop, name drop, name drop, you know, five pages of filler and then a couple of bullet points at the end of the chapter.

SPEAKER_04 49:27

Yeah, right.

SPEAKER_00 49:28

You know, if you ripped out those end of chapter bullet points and stapled them together, you'd have a great 20-page PowerPoint. Yeah, but it's not that interesting. Yeah, um, so that's part of it. That's kind of the flip answer. The sort of deeper answer is that people remember and are more likely to act on stories than they are on uh just instructions. So I I give this example sometimes, like I had a company, uh, you know, they were up against this issue, like they had a freemium model, so like there was a free version of premium, and companies like that live and die on you know what percentage of the people decide to upgrade and pay. You know, so I can just tell them, like, hey, this is what you got to do, test it, and I did, and you know, okay, that's very nice. Thank you for your advice. Or I could tell them a story about a different startup that was in a similar situation, uh, same problem. And they were like, So, what are your plans? Well, this was like week two of our accelerator program cycle, it's gonna take us another month and a half to build. So, probably about two weeks before demo day, we'll be able to flip the switch, turn it on, and see what happens. We're like, No, yeah, if you don't like if the number's wrong before demo day, you got nothing in two weeks. What are you gonna do? Stand up on stage and like what's our alternative? I said, Well, you just put the screen up, put the page up, yeah, yeah, right, and then like put a buy now button. And if anyone clicks it, pops up is a coming soon. We'll tell you when it's free, but at least you'll know like the assumption that X percent will convert. If you put that up there and test it for a week or two, then it goes from an assumption to prove it. Because the people on the site, they know, like they know that they think that they're buying. So this other company, and I will reveal the name in this case, I'm saving it for the end. Uh, so that's a great idea, let's do that. And they come back a week later, and they're like, Yeah, we're screwed. It's like, why? What are the numbers? They show us the numbers. Like, well, that's about a tenth of what you needed. They go, Yeah, tell us about it. So, well, what are you gonna do? And they said, Well, we had this other idea to do this. It's like, you know, one part of our site, lots of people like it. We're gonna go sideways with that. That's okay. Of course it's okay, like this is a dead end, go down the other route, we'll do it.

SPEAKER_04 51:36

Exactly.

SPEAKER_00 51:37

And then in the remaining like eight weeks, they came with a totally new direction, raised by, and that company is now called SeatGeek, and they're unicorn. And they came very close to not being through the next initial instinct of finish building our premium features and then see what happens. It's a similar idea with the uh index card app. It's like, what can you do now quickly? No work, yeah, little work, no money, or little money, and move an assumption into proven. So I have two ways of doing it. I could tell the story, or I could just tell them what they need to do. It's actually a little faster just to tell them what they need to do, but to tell them the story, they're like, oh man, I gotta go do that. Right? They identify with the founder that gives them permission. Like, I guess if they were wrong, I could be wrong. I should figure this out. So I realized over the course of running the accelerator, it's just a more effective way to get the point across, not to mention more interesting. Uh, and then this occurred to me just recently. Uh, and I I promise you, this isn't me being like full of myself, but do you realize that no religion starts their like their book by saying, Hey Maxim, this is what you can do or not do? Right? You should just tell me what I can do. Don't kill, that's great. Why don't we start with the Ten Commandments? No, yeah, they all start with the stories, the Genesis story, how the world was created, how the founders came about. And when you think about it, it makes sense because that's how we remember things. I didn't come up with this idea. Yeah, I mean it's been around a long time, but the idea of using it in um to teach entrepreneurship, yeah, uh, there were very few kind of models to base it on.

SPEAKER_01 53:21

I couldn't agree more with you. Like there's a couple of videos pop to mind while we were speaking. One, the most underutilized hack are paid ads for customer discovery. Because you can do ABC and see what works. Uh you haven't even built anything other than some vaporware for for the outscript.

SPEAKER_00 53:44

Well, you go up on Wix or SquarePage, you put something whatever. You use a different brand name. Maybe if you're worried about ruining your company name, just do it, it costs you a couple hundred bucks.

SPEAKER_01 53:56

Yeah, I agree. And and the other thing that that came to mind is like my favorite. So I spent 13 years between Iwa and Deloitte, and uh with Deloitte, I think it was we had a session with a guy by the name of Dan Rome. And Dan Rome has written a book called Back of the Napkin. And the whole premise behind the book is as follows Our human brain is wired to process visual information seven times more effectively than any other what it's uh auditory information or whatever, seven times more. And so we did an experiment like flip cue cards uh with um uh like we we listened to the words and then we did cue cards with the words or or images. We remembered seven times more words than what we heard. Um, and and so it's the same thing, like storytelling is probably the most undervalued or an underappreciated skill that found us need to develop. What are you selling and what are you erasing? It's all storytelling. What are you engaging or inspiring a team?

SPEAKER_00 55:01

Yeah, uh it's harder. It's harder. Like, you know, I teach the course, I teach entrepreneurship. In part, uh, I got kind of roped into it because I was asking um his name's Noel Masterman, he's a professor, uh, used to run one of the business schools, uh, and he wrote a great book called Innovators, uh, sorry, the uh founders' dilemmas about like you know different choices founders have to make and how it affects their um you know their startups ability to succeed. And like I actually just want to hit him up for introductions to publishers. That's like when I was first starting to write. Yep. But he did something that was very smart, right? And and like he's a surprisingly good salesperson. He said, Andrew, if you're gonna write a book that could also be a textbook for teaching entrepreneurship, you should teach entrepreneurship and run the draft past these students.

SPEAKER_04 55:51

Yeah. Yeah, yeah.

SPEAKER_00 55:53

Okay, and then somehow I twisted my arm and I had to teach two other courses first. But uh yeah, he's really good. But it really makes a difference, it really made a difference.

SPEAKER_01 56:03

Oh, 100%. He gave immediate feedback. Um, I we're at time, Andrew. Any closing thoughts that you have, where should people follow you? Um, in the show notes, we'll drop uh links to your book.

SPEAKER_00 56:15

Um just yeah, so there's a couple of things, right? It all depends on what you need, right? So if you are a founder and you're working on a startup right now, you're thinking about quitting your day job, get the book, right? I know it sounds very self-serving, but it's like, you know, 220 pages or something like that. You'll sit down in five hours. I guarantee you you'll come up with a half a dozen or two dozen things you're like, oh damn, I would have made that exact mistake.

SPEAKER_04 56:44

Yeah.

SPEAKER_00 56:45

So there is literally nothing else I can think of that you could put five hours into that will move the needle on preventing failure of your startup and maximizing your odds of success. So if that's all you want, and you're like, okay, I'm tired of hearing Andrew speak, just go on to Amazon or go in the show notes, you'll find it.

SPEAKER_02 57:02

Yep.

SPEAKER_00 57:02

If you're kind of curious about the stuff that we didn't talk about and what I've done, and like the corporate innovation side or the other stuff, uh you can go to my website, it's Andrew, the letter B is in boyacerman.com. There's more information there. Uh, you know, read it to your heart's consent. If you happen to happen to have a startup that is in the prop tech or construction tech space, and it's not just your cocktail napkin, you know, you and like your buddy and maybe one person from your ex-employer who's your first design partner customer, uh, and you want to reach out to me, reach out to me on LinkedIn. Just uh, you know, in that outreach, just say, you know, I'm with you know the future ventures podcast, I saw you on it. Uh and like I really do have a startup that's got some revenue or some traction. Here's what I do like concise three or four sentences, uh, and you know, I'll take a look at it. I do respond to all of them, even if it takes me a little bit of time.

SPEAKER_01 57:59

That's awesome, Andrew. Thanks for your generosity of time and for the insights. Highly appreciate it.

SPEAKER_00 58:06

Thanks for having me. It was fun.

SPEAKER_01 58:08

My pleasure.