Kyle O'Hehir, CTO of Constitution Lending - Real Estate Open Season - The Michael Girdley Show Episode 43
21 Jul 2022 · 66 min
In this episode of The Michael Girdley Show, Kyle O'Hehir, CTO of Constitution Lending, walks through his unconventional career path—from a commodities desk on Wall Street to a hands‑on real‑estate investor and credit provider. He explains how he identified his first short‑term‑rental (STR) opportunity in Savannah, Georgia, using data‑driven screening and regulatory due‑diligence, and how that deal yielded a 40% cash‑on‑cash return. After leaving the hedge fund, Kyle built a portfolio of affordable‑housing multifamily assets in Connecticut, sourced distressed loans at judicial auctions, and launched a hard‑money lending operation that now originates $10 million a month for equity‑focused investors. He discusses operational challenges (self‑managing versus third‑party property management, in‑house general contracting, and the “hit‑or‑miss” nature of external GCs), capital‑stack strategies (partner capital, bank relationships, credit‑hedge‑fund facilities), and the decision‑making framework he uses to allocate time across multiple ventures. The conversation also delves into broader entrepreneurial philosophy—effectuation versus VC‑style big bets, the importance of a translation layer for blind spots, learning from mentors, and the role of gut instinct versus data. Kyle shares advice on saying no, focusing on high‑leverage activities, and how he balances domain‑specific expertise with transferable business skills. The episode ends with contact information for listeners interested in debt financing.
Chapters
Hey, Michael here. Welcome to another episode of the Michael Girdley Show. I was joined this week by my new buddy Kyle O'Hare, who is actually out of Connecticut and runs a lending and real estate business that he has bought dozens, if not more, different units of real estate with his own money and partners' money. And really pretty inspiring, high-energy guy that I met on Twitter. So he's been pretty quiet on Twitter because he's been really busy lately, but came in, we talked a lot about his story, leaving the hedge fund world, becoming a real estate investor buying a property sight unseen in Savannah, Georgia, having it turn out to be a huge home run and then parlaying that into a bunch of additional units that he's bought, done a bunch of other things on top of that in his career. So it's been cool to talk to him. And then we spent a lot of time talking about a lot of the differences between my age, 47, and his age, 29, and the career in business and how to think about different things and really enjoy talking to him. Super curious, smart guy and somebody I learned a lot about and was excited to hear his story. So Uh, with no further ado, we'll have a quick word from our sponsors and then on to the episode. Thanks for being here. Hey, Michael here. Uh, sponsor for today's show is actually, uh, a product that I'm a part of called DMBridge. Uh, and what DMBridge is, uh, is a service that we built, uh, to solve the problem that Twitter's direct messaging functionality is a total mess. So we built DMBridge to help you fix that. Um, a lot of the other solutions, uh, do things like requiring you to install a whole nother inbox. We didn't want another inbox. So we created DMBridge, and what it does is it takes all of your Twitter DMs and has them appear inside of your email inbox. So you can reply to them just like it's a regular email. You see them just like it's a regular email. You can search them later like it's one of your regular emails, all just by using DMBridge. So, uh, we're currently live with the product. Uh, would love for you to sign up and become a customer, uh, and check it out. So you can find that at dmbridge.app. And go on there, put in your name and be either part of the beta or join us as part of the live use of the product. And again, check it out, dmbridge.app. Dude, Kyle, thanks for being here. I'm like super excited to chat with you after getting to know you on Twitter. Really glad, really glad you're joining me today.
Yeah, man, thanks for having me. You're a, you're a legend on the SMB, real estate, etc. Twitter. So it's, it's an honor to be here and yeah, really fired up for this chat.
Well, you're my first official shitposter guest, um, so I think it's gonna be fantastic. I'm really excited about going down the path of that.
Oh wow, I am really fucking honored. That's, that's huge. Thank you, Mike.
You're welcome. So, uh, I, I know you, I think, pretty well, but, um, my audience likely does not, so I'd love to get the— love to get the brief life history from you, and then, uh, let's go from there.
Yeah, definitely. So I, um, I started my career right out of college on Wall Street. Um, I was a commodities trader at a fund, um, here in Connecticut in Greenwich. Um, did that for, you know, I guess 4-ish years. Um, I kind of alongside that was looking for things I could do with my personal capital that wouldn't, uh get compliance up my ass. And in reviewing the compliance handbook, it kind of had a section that said real estate open season. I was like, real estate open season. All right, let's see what this is about. And so from there, the first real estate I bought was actually STR. I always— it's a, you know, compliance. You got to take compliance seriously. I even— even though I'm on my own, we still take compliance real fucking seriously. You can, you can, you can get hurt if you don't. So, you know, I'm trying to follow the rules here. And so, you know, my first foray into that was just buying STR in Savannah, Georgia. And that was a crazy learning experience for me, right? As a guy who worked at a hedge fund, you know, the whole point of working at a hedge fund is you don't deal with operational shit. It's not your thing. That's why, that's why people go work at hedge funds. You know, you get to, you kind of, you get to be a speculator. You get to, you know, wear boat shoes to the office. It's, it's awesome. It's really fucking good. But you don't get your hands dirty, right? That's the whole allure of the, of the thing. And so, you know, me like an idiot, I was like, why don't I, why don't I get my hands dirty? And so I did and quickly found out that, you know, Main Street is not like Wall Street, um, but, but I liked it. I liked it a lot. Um, in particular, I was a huge fan of the feedback loops, right? I would do something dumb, or, you know, my team would do something dumb, and immediately I would get kicked in the ass, and I would have to figure out how to be smarter the next time, right? Whereas public markets, you don't have such a tight causal feedback loop, right? You might have— as an example, right, so my desk, uh, was, was, um, the fund I was at, 20% of the front office gets canned every year. So in 2018, I was in the 20%, my desk was. Um, and that year, right, the, the Trump tariff stuff happened, and we got ran over on some things that, um, you know, in the absence of that nonsense, we probably would have done all right on, right? So you— to me, private markets, there's this really tight causal feedback loop, which I loved, right? And so from there, I was like, all right, um, you know, One of the things that I found challenging about the Savannah stuff was that, you know, operationally it was, it was pretty high touch. And I wanted to do something, you know, I want to do something sort of closer to home that I have more control over. So in 2017, I started buying real estate in Connecticut with an emphasis on affordable housing. So, you know, buying in areas that were distressed, you know, renting to folks on HCVs, Housing Choice Vouchers from Section 8. You know, it's probably the only thing that draws more ire from the community than STRs. So great choice. And so today that piece of the business is about 300 units. And, you know, as sort of an extension of that, I got into buying bad loans from local and community lenders and foreclosing on, you know, slumlords who'd sort of run some of these assets into the ground. And then, you know, branching off from the credit investing, I got into actual, you know, just straight up originations, right? So we do $10 million a month today of origination to, you know, basically guys who were kind of like me back in the day, right? Equity side real estate investors who are looking to do some kind of a portfolio assemblage kind of thing. And yeah, that's kind of the— it's kind of the story, sort of, sort of start to finish.
Yeah. So your first— you're working at the hedge fund desk. And your first— you decide to make your first real estate investment be a short-term rental. And you're in New York, you decided to do it in Savannah, Georgia. Like that. I understand that, right?
Yep. I had never— yeah. So I hadn't been— after I closed, I went there. And I was like, that's a pretty cool town. But the reason for that was I did back in the— this is back when like, AirDNA was literally a dude selling like fucking spreadsheets out of the pickup truck. And so I found them somehow, and I was like, this was like 20— I think this is 2015, 2016. And I hit them up and I was like, bro, I want to buy some— I'm gonna buy some spreadsheets, man. And so I did that, and then I just, um, I'm a, well, self-taught. I studied math in, in college. I'm a self-taught, you know, programmer. So most of this— most of the stuff I did at the hedge fund was, you know, data science kind of stuff. Um, I, I'm a big Python guy. I'm not bad at JavaScript. Um, but so what I did was I took that data and I lined up, you know, what they were showing in terms of, you know, revenue, um, kind of by MSA, and then lined that up with— um, Zillow has a cool API that'll give you like median home price per zip code. And so lined those up, kind of said east of the Mississippi, sort on kind of like this gross yield metric. And Savannah and some other places kind of came up through that screen. And that was sort of how I— that was kind of my first screen. And the second screen was, you know, where is this actually legal? And not— not where is it a gray area, where is it actually legal? And so one of the cool things about Savannah is that, you know, been a tourist town for a long time. They had a very well-established, very well-thought-out licensing process, which they did end up changing. But, you know, when I started buying there, it was a very straightforward thing. And so those were kind of my two screens. I sort of had this, you know, does the math make sense screen, and then this kind of regulatory certainty screen. Yeah.
So you, you sorted— well, it sounds like you were able to kind of get an estimate of what your, your yield would be. And then you could decide, okay, I'm gonna do more or less. Yeah, yeah. And then is it legal was the other check. So, so you bought it without actually going to visit it first? You closed on the property?
Right? Yeah, no, I, it was the first, the first was, was just a condo in downtown Savannah. And I, you know, I did a home inspection, which I do not, I don't, I don't pay for inspections anymore. I just run through it myself. But Yeah, back in the day I was doing that. And so, you know, the thing was, the thing was a concrete box, really. So there wasn't that much that could be wrong with it. And so the inspection came back clean, you know, and I said, all right, let's, let's do this thing. And then I flew down there and, you know, it's a cool— it's actually, I proposed to my fiancée there last year. It's become a kind of a cool place for me, a place that I enjoy and I go back to. But yeah, I mean, I had never been there before. Before I closed on this thing and flew down there and figured I should probably, you know, see what it was that I bought.
So, and what was your plan to like manage the condo? Like, did you hire a, is there like a short-term rental property management company or did you just start doing it yourself?
No. So that was one of the first lessons I learned, you know, coming from Wall Street, right? If you don't have the operations solved for, it's going to be you. And so the, you know, the, it wasn't, it wasn't like a huge operational lift, but when it got to like 10 units, then it was, right? And so, you know, I, I was more or less self-managing from here. Had a great, great cleaning— a lot of the STR guys are like, you need a killer handyman, you need a killer cleaning crew. So I had those two, and so it wasn't terrible, right? I mean, the worst thing that would happen is I'd, you know, I'd be out to dinner with, uh, with my girlfriend at the time, and, you know, some drunk person would call me being like, I don't know how to use a door. And I'm like, it's like every other door, man. Like, what the fuck? Like, just 'Come on, you can, you can do this. I have faith in you,' right? That was the— that was— so that was the, you know, that was kind of the worst part of it. Um, but when it got bigger, you know, we, we did end up hiring professional, um, management who, um— well, I mean, that wasn't— that was another great lesson. Third-party management is, uh, is hit or miss.
Uh, it seems like a real messy kind of thing. So anyway, so for the, the first one you did Um, did your, did your actual returns match kind of what your model showed, or have they done better or worse?
Not at all, not at all. It was a total, um, I think, and it's crazy to think that I was okay with this, but I had underwritten it to, you know, a 12% sort of, not, not IRR because I don't know anything about what my exit's going to be or whatever, and it's, it's a consumer good, right? It's not an investment thing, so Who knows? But, you know, the cash-on-cash returns I had penciled in, um, they were something like 12%, and they ended up being more like 40%. Um, I didn't, I didn't appreciate how— I thought there would be some seasonality to it. Um, there wasn't. I mean, me, I'm from Minnesota. I, I went to Georgia in July, and I was like, fuck, man, why would, why would anyone come here? But then, you know, I start to see the bookings come in for July and August, and it's all people from Central Georgia who are trying to get out of Central Georgia. I'm like, all right, all right, it makes more sense now. But yeah, it, it ended up being a thing that was, you know, 97-ish percent occupancy year-round. And, you know, at a point they actually capped the licenses per neighborhood or per ward, and that was massive for us too. So the supply got cut. I mean, there was a lot of Yeah, there were a lot of wild things that happened that really made that sort of a— I kind of got spoiled by that, by that first, by that, you know, first foray into this, unfortunately.
So, so that was 40% cash-on-cash returns. And I assume you used some debt to buy it. There was a mortgage on the property. So it's 40% on your return on invested capital.
Yeah, for— yeah, levered. Yeah, levered 40%. Yep.
Yeah, that's amazing. Well, congratulations. Um, okay, so this is really cool. So you do one and you're like, holy crap, I'm making a lot of money doing this. Also, I'm in Savannah. It's in Savannah. Um, by the way, did you— at what point did you get there and you're like, these people all talk so slowly? Like, Has it— has that ever struck you as—
So I had a local lender. Honestly, every one of the closings, I was like, I'm going to kill all of you. I cannot believe— I mean, it was for me as like a Yank and, you know, the guy in the Northeast. I mean, like, I— yeah, there were multiple points where I was like, I don't understand this. How are you people in the same fucking country as me? This is nuts. But, you know, I got accustomed to it. I like to— I like to think that they got accustomed to me. I mean, it took some— it took a couple of yelly sort of phone calls. But now I think at a point we kind of, you know, we came to an understanding of sorts.
Yeah, I dealt— we own some property in Alabama once, and I dealt with a broker there, and literally he talked so slowly. That I would do emails in between my opportunity to talk when I was on the phone, because it would take 3 minutes to say like, how's it going? And, you know, a normal person is like, hey, what's up? You know, great. How was your weekend? Great. Okay, cool. And we move on, right? That was 3 to 4 minutes of him talking. And eventually I was just like, oh, I know how to deal with this. I have to multitask. That's the only way to get through it because they just talk so slowly. It's just unbelievable.
So my, my, so my favorite kind of cultural Southern clash story, I, I bought a mixed-use building and I needed a— my resi broker, you know, wasn't really going to be much help leasing the commercial space. I said, that's fine, I'll find a commercial broker. So someone gave me a rec. She seemed to have her shit really together. And then, you know, we're kind of like 3 months into the thing, 6 months into the thing. And I'm like, hey, I don't remember what her name was, but I was like, hey, you What's going on with this? And at like month 6, she's like, yeah, you know, I, uh, I lost my CoStar login, so I haven't had a chance to list it. And I'm like, lady, are you fucking kidding me? We're 6 months into the listing agreement. You haven't listed it? No wonder we haven't gotten any fucking calls. And so that was, I mean, that was one of the ones where I was just like, damn, this is a different world. This is not New York. This is not New England. This is something else. So yeah.
So you said you were from Minnesota originally, did I hear that right?
Yeah, yep, I'm from the Twin Cities.
So at what point did you make the transition from decidedly not being a Midwestern person anymore to being very New York? I don't mean this as an insult, but like, why do you say that? Your whole vibe and everything is like New York.
It's a vibe thing.
Yeah, exactly, that's what you mean. Yeah. Well, I mean, if you told me you were New York— if you told me you were New York or Philadelphia, I'd be like, yeah, okay, yeah, totally. Um, you're not angry enough to be Boston.
That's great.
Um, but yeah, at what point did you make the transition to full New Yorker?
That's a, that's a good question. Um, it was honestly, it was probably in college. Yeah. So like, I, um, I, I, I tweeted a bit of this story at one point, but, um, I went to a state school and, you know, it became clear pretty quickly that what I wanted to do was not something that people from that school did typically. And so I just got really, really aggressive about it. Right. So, I mean, I was hopping on— I went to Maryland College Park. And so, you know, I was hopping on the Megabus out of D.C. to New York on like a Thursday, skipping class Thursday, Friday. Doing that, you know, coming back sort of Saturday morning, right? Sleeping on a buddy's floor so that I could meet, you know, some of the people who did end up going into Wall Street out of Maryland. And I think that was kind of the— that was the time where I sort of had to make the shift, right? From sort of reserved Midwest, you know, inoffensive, very, very nice to like, all right, if I want to fucking do this, like, I really have to do it. It. So that was probably when I— I mean, I still identify as Minnesotan and Midwest and whatever, and the people are great. I mean, I love the people, but yeah, I think you're right. That was probably the breaking point for me, was in college.
Super cool. Yeah, no, it's— I mean, look, I appreciate both. I love going to Minnesota too, and the people are just like— I can't even do the accent, but they're just like, hey. We go to the lake on the weekends. So chill.
Don't you know, Michael Girdley, they're so nice. You want to go to the lake? We'll go up to the lake.
Hey, hey, we're going to go to the lake. Anyway, okay, so how do you go from one basically YOLO investment in Savannah and then you get fired from the hedge fund desk, right, when it's yank, rank and yank? And then, so what's— then what's next? What do you do for number like 2, 3, and 4? How do you— how do you keep going?
Yeah, so I had— we had got the thing to about, uh, I think it was probably 8 when my desk got the axe. And at that point I was like, well, it's, you know, it's— it's not anomalous for the style fund I was at, right? I was at a multi-strategy fund, um, you know, they're— I think they're probably $40 billion at this point. And so they're doing a bunch of different shit, right? And so it's pretty— it's, it's well understood in the industry that, you know, sometimes you're, you're just in the bottom, you know, decile, and then you gotta, you know, you're gonna get the ax and you got to do it again. So I had interviews to basically do the same thing again, um, you know, at Point72, um, Tudor, some of these kinds of operations. And I had 2 months of kind of non-compete I had to burn through. And some of my crazier friends, uh, God bless them, said, you know, why don't you just do this other shit? Like, you seem to really enjoy this other shit. And so I had time, I had kind of this transitional period where I had gotten the stuff in Savannah to somewhere between 8 and 10 units. And they had— that's actually when they made the regulatory shift and capped the licenses. So it wasn't really feasible to do more of that. And so what I started— so what I ended up doing was I started buying, um, in Connecticut on a— and, and still a very yield-centric, um, similar to the, the, you know, kind of data approach I took down there. Very yield-centric, you know, what's— I mean, Connecticut's not a, not a hot market. I mean, it is now, but it wasn't then by anyone's imagination. Um, and so, you know, what's a way that I can kind of do the same, do similar returns, but, you know, close to home, and I'll have a lot of operational control. And, um, yeah, so I kind of took those 2 months and played around with it and candidly had a lot of fun. And I was like, eh, fuck this, I'm not going back. And, uh, that was, that was a big— I mean, it was a wild thing to do because like I had seen myself and totally, you know, enjoyed being, yeah, hedge fund guy in Connecticut. This is nice. But, you know, it was, it was ultimately not as me as, you know, picking up crack houses and, you know, eventually buying distressed loans and etc.
So yeah. And so how are you kind of funding all of that? Because that's a pretty capital-intensive endeavor, right? Like, are you— I mean, you're— I'm sure you're making good money at the hedge fund, but at a certain point, like, you're living too. So like, how, how did you start to build that portfolio you know, is it buy refi type, type place or what did you end up doing to kind of grow that capital base?
Yeah, no, it's a great question. So the first property I bought in Connecticut, very similar to like Chris Power's story or someone else's, right? I, I picked up a 4-family property for just short of a buck and lived in one of the units. And that was, that was kind of my first Connecticut deal. And the returns on that thing were wild. Um, they still are. I still own it. It's one of my favorites. Um, a buck— uh, sorry, yes, a buck is a million, a yard is a billion.
Okay, cool. Sorry, I don't speak— I don't speak hedge funder.
No worries. I love— that's the— that's probably the first time in a long time someone's asked me that. I love that. So yeah, a buck is a million. So yeah, so it was— I mean, it was a— it was— it was a stupid— I, I saw it, so I got my license because I I hate brokers. I know this is like a big Twitter taboo thing, but like, man, fucking broke. Like, a good broker, hey, listen, that's awesome. But like, most of them are not. Like, fuck, no, they're not. Um, so I got my license so that I could kind of see the market and like chase shit down myself. Um, and I saw this one, this thing was like a 10-cap. It was ridiculous. It didn't make any sense. Um, and, and, and that was at list. And so I was like, all right, this seems obvious. And so, you know, I bought it, and I obviously haven't seen a 10-cap since then. But, um, So that, that was kind of the jumping off point, right? And then from there I started— well, for one thing, I couldn't find any more 10-caps in the town, in Stamford, where I lived. And so I started looking in some, uh, uh, should we say, up-and-coming areas. Um, and there were a lot of opportunities. There were— there was stuff where I was just like, holy shit. I mean, this doesn't— I mean, this is so Connecticut, right? I mean, the rents are high. It doesn't matter where you are, the rents are ridiculous here. Um, and so, and the asset values at that time in a lot of the places where I was kind of sniffing around, they, they were not that high. Like Connecticut, outside of Fairfield County, which is, you know, the— which is effectively a New York suburb, um, they didn't really bounce that hard after the crisis. And so, you know, I was picking shit up for— I paid $20 grand for a duplex I paid $8,000 for a 3-family that literally rents for $6,000 a month now. I mean, just hilarious, hilariously cheap shit. And I also got pretty good at sourcing, right? So I went to a lot of foreclosure auctions, which Connecticut's a judicial foreclosure state, so they happen Saturdays at noon on premises. I went to a lot of tax deed sales. Yeah, just kind of built out like this sourcing apparatus. And in answer to your funding question, the gurus sort of tricked me on this. I was under the impression I would make a shitload of money doing this out of the gate. That's not how this works. And so, you know, I got into— I got into spots on some of this shit where I was like, oh, fuck, like, I own a lot of real estate, but like, I have no fucking money. Like, this is— this sucks. So it was great that the first deal was, you know, teed up housing and that was handled for a long time. And then from there, you know, I— one of my buddies from Wall Street joined me And so, you know, we kind of pooled our resources. Other than that, I did some deals, some one-off stuff with like friends from college. But for the most part, it is, it is his capital and my capital.
Right.
And so the strategy is very much we were doing some pretty heavy value-add stuff and we still do heavy value-add. So we brought general contracting in-house a couple of years ago, which really helps us just kind of mitigate that, that risk broadly because it's probably the biggest one that we face. But back in the day, we were hiring third-party GCs. You know, for the most part, I wouldn't say— wouldn't say YOLO investing necessarily, but definitely paying a price for something where it was like, I don't know how much it needs, but like, this is cheap. Um, so yeah, that was— that was kind of, um— and then today, you know, on the funding side with respect to lending, I have— I have bank relationships, um, I work with a couple of credit hedge funds that I have facilities with. Um, so yeah, the— the capital stack has gotten a lot more interesting In the early days, it really was my partner and I and, you know, $100 grand and God, let's hope everyone pays rent next month. Yeah, totally dig it.
All right. That's, that's super good. And so there's the own, the own-operate side. And then you mentioned you're also doing credit, right? So you're doing hard money loans to people. Is that basically what that is?
Yeah. So we saw on the, on the, on the lending side, I got into credit investing via distressed credit investing. So, you know, I think 2018 I bought my first loan from a local lender. That was, it was interesting. I knew a lot about the foreclosure process just by virtue of being, you know, Joe Schmo who shows up to the auction. But, you know, it's a different thing playing as the, as the plaintiff. So, you know, that was kind of the starting point for that. And then there came a point where I was doing more like special situations lending because, you know, a lot of my banks didn't really have bad paper. And so, you know, someone would come in, they inherited a property, they've got some other big bill coming up, but they own the property free and clear. And, you know, basically a hard money loan at 50% LTV, super safe stuff, right? And so, you know, did that for a bit, but that flow is really sort of flaky as well. And so then that was when I was like, you know what, we're not bad at lending people money. And back when I was like really hitting the acquisition side of the business hard, the equity investing side of the business hard, I really fucking hated all my lenders. And so like, maybe we can give people— maybe as a guy who's been on the other side of this table, we can give people just a better experience, right? Because if you think about lending broadly, and a lot of these alternative lenders popped up post-Dodd-Frank, right? A lot of the community lenders, a lot of the regional lenders pulled back from the space. And so all these alternative players popped up. And so you would think, hey, I'm paying a premium for this, I should get a better product. And that's generally not how it works, um, you know, sort of strangely enough to me. And so, you know, as an example, like, I've never closed a hard money loan where I was the borrower with any of the— and I borrowed from all the big national guys— in less than 45 days. And to me, that just seems wild. Like, if you're not looking at my tax returns and you're really just doing kind of an asset FICO underwrite, how does that take 45 days? It's fucking crazy. And so, you know, as an example, right, last quarter I closed a guy's loan in 4 days, right? And so it's turning on its head the idea that— and, and the reason they do it like that is because their ultimate client is capital markets. Their client is not the borrower. They couldn't give less of a shit about the borrower. Don't care. It's just, you know, if— listen, if you don't do the loan with us, some other dickhead will do it and we'll sell it to Wall Street and fuck you. We don't care. So we're taking— we're kind of turning the thing on its head and saying— and a lot of finance is like this, right? If you ask someone in finance, finance loves its acronyms. No one in finance knows what NPS is. No one knows. No one gives a fuck. Doesn't matter, right? Because you need it. You need money. You need a bank account. You need all this shit. So they don't care, right? And so our entire model has been from the beginning, what happened if we said, let's make this not suck for who we think the actual client is, i.e., the borrower?
Yeah, I like it. I like it.
Cool.
So where do you think you take all this? What's your— what's your bigger vision? Or do you— or this is just fine. That's also a fine vision.
Honestly, Mike, this is— so this— I want to ask you a question because you— I look at the shit, you do a lot of shit. How do you pick what shit you do?
Yeah, like, how do I do it?
Like, what's your process? Like, do you have an algorithm? Do you have a dartboard? Like, what's the— how do you do this shit?
Well, some of it I have no choice because I, like, inherited it. So that's just the way life works. But I mean, other things, I think that the core of the algorithm, believe it or not, is, you know, I look at a ton of stuff and then the things I end up continuing to work on are ones that I just can't let go. Like if I'm looking at potential opportunity or talking about something like I'll talk about 10 or 15 ideas and explore different stuff, or the people I'm working with will go explore it out of that bucket, like the one that I'll really go deeply into and pursue and just make a reality is just the one that every fiber of my being tells me that it's going to happen and it's one I need to work on making happen. And so, you know, it's that way when we started the education business CodeUp. It was that way when we, you know, started the software company Dura. That way when we— like the coffee thing, I talked about that for a year until I finally just said, I'm going to make this happen. So that's the core of the algorithm.
So it's you— you would say that of the different dimensions that one of these, you know, that an opportunity could exist on, right, you put above all the other dimensions, are you having a good fucking time?
Um, I trust my— I trust my gut as a, um, as the best distillation of all the data points that I'm looking at.
Got it. So there are other inputs, but it's, it's ultimately Okay, so there are other inputs, but it is ultimately you kind of taking them all in and being like, yeah, this is the thing, I'm going to chase this down right now.
You know, the, the breed of entrepreneurship that I practice is different than what other people do, right? So I've talked a bit about this thing called effectuation, which basically, basically at its core, you go and run a lot of experiments around your hypotheses and then see what kind of sticks to the wall. So everything is like an incremental bigger bet. So like when we started Dura, which has grown into like a 300-person software company, we knew that the core bet was okay, like, like the core bet here is can we— if we're going to grow by acquisitions, we need to go find our first acquisition. So like that was an incremental small bet before like I made a bigger bet later on and before like my co-founder went full-time. We make incrementally small bets and develop conviction over time rather than making like, like the opposite, which is like the VC path where you make like this huge conviction at the beginning and say, okay, I'm going to go raise a bunch of money and work on this vision. And 5% of the time it's going to work out like the brain of entrepreneurship. I practice is the opposite of that.
So it's sort of a— it is kind of an MVP sort of thing. So you like to see some product market fit. If it works, you'll add to it. Um, in terms of capital, and I assume in terms of your time, right? So, okay, that makes sense. I mean, I think that's— I think— I honestly think that that's— I think that's one of the hardest things about, about this, is that there are like— the markets that I play in are not huge. Um, so, you know, like, I, I did a bad debt deal that was around a buck, you know, it closed last week. And that's something that I personally am going to do quite well on. I don't, you know, there's no outside capital, it's me. And so like, it's a worthwhile thing for me to do, but it doesn't really— it doesn't, you know, there's a point at which that might not make sense, right? And I think continually sort of looking at it and being like, is this a thing I should do? Is this a thing? You know, there was a point in the pandemic where nobody was paying rent, and I was like, oh shit, I mean, if I could sell this thing for anything I would take it, right? I feel like it's a, it's a, it's a, it's an evolving thing and trying to figure out, you know, what you do in particular on the time front, right? What you do with your time and what is sort of, you know, worthy of you spending time on. I feel like that is the, that is the biggest challenge of this thing. And in particular, the way that you do it, right? Where you do so many things and, you know, they're, they're all experimental to an extent, but you know, now and then one of them really catches, right? And you got to figure out which, which ones you can kind of put on the back burner while you chase that one down. I feel like that allocation problem is one of the— for someone who's not, like you said, right, VC-backed, head down, super myopic, chasing down this one thing, trying to figure out if it has product market fit— okay, it does— and then building that, right? I feel like that's I, yeah, I feel like this sort of portfolio approach to it and, and the allocation of time within that problem, right? I feel like that is, that is, I don't know, it's a, it's a massive problem that I think about every single day. It doesn't have a nice closed-form solution, but, um, it's awesome to think about. It's awesome to, to, to talk through with you how you think about it.
Yeah, well, I mean I think to add to what I said, you know, I hear you talk about it, it's like, oh, there's something I didn't mention. Like, I have like a 10-year vision of where I want to take things. And like, like I'm looking for reasons to say no to do stuff, right? And so that gut factor also gets impacted there, which is like I'm often having to say no to things that are not direct line path towards that goal, right? Like they can't scale big enough or they're going to take too much of my time. Like it might— it could be super fun and super engaging and I might be passionate about it, but I have to have self-discipline and say, okay, well, here's my net worth goal for 10 years from now. And like say no to a lot of stuff because it's like, oh, like that's going to take— that's going to— that's going to preclude me and it's not straight path to where I want to be.
Yeah. Now I think you had a killer thread at some point about saying no. And it's, yeah, it's a huge, it's funny because when I first started doing this, I never said no. And now, you know, I've shaved quite a few points off my IQ and I am somehow still alive. And now I say no a lot because there are things that, you know, my metric. So you've got the kind of mosaic and you take it in and then there's kind of a feeling around you know, go/no-go with respect to this thing, right? For me, a lot of it comes down to— it's similar. It also comes down to like, do I enjoy it? Um, and I actually just hired a COO to run real estate/construction here. So, you know, increasingly I'm trying to find ways that I can do the things that I'm actually really good at. I mean, let's be clear, like, I, I— there are a lot of binary things that kind of anyone can do. And the sooner you can delegate those and get to doing the things that are actually kind of high leverage that you're good at, the better. And so, you know, I like to find things that are— I like to find things where I can do those things. Um, but there's also a component to it which is, you know, I think about in terms of like dollar per brain. Like, is this— how badly is this going to hurt my head doing this? Um, and I've found that, you know, that's another big thing coming from Wall Street that you don't appreciate until you get here, which is that the fucking spreadsheet can say whatever. Spreadsheet could say anything. But it's not even that the numbers are going to stray from that reality. It's that there's things that are not in the spreadsheet that are going to hurt you way fucking worse than the numbers missing. And if you don't think about those things and try to anticipate them, you're going to be on the receiving end of a lot of bullshit. And, you know, do you want that? Right. Do you want that? I mean, I think it's funny because I'm, you know, I'm at a place where I mean, if I did this again, I probably wouldn't have built the affordable housing portfolio because I would be like, it seems too hard. Do I really want to deal with, you know, some homeless dude starting a fire in one of my buildings and in January to stay warm? Not really. That sounds terrible. But now that the infrastructure is there, you know, now that the infrastructure is there and my team is accustomed to shit like that, right? It's like, all right, I'm kind of stuck. Like, I kind of have to do more of this. Um, so no, it's an— it— that allocation problem, I think, is so— is so interesting because it is so multifaceted, and it— and it's always changing. It's just— it's just always—
yeah, I mean, I'm a huge believer that the multi— you know, really tough kind of multivariate and kind of indeterminate decisions like that, like, especially when you only have You know, you have 50% of the information, you can't predict the future, there's 80 different variables you have to consider. Like, your subconscious in your brain is actually really good at distilling those down into the right answer. And I think people make a mistake in trying to— especially where their personal life goes— like, like, try to be rational about that and try to use your top-tier brain to solve that stuff, because it's just beyond our cognition. So I just learned to really trust that stuff. So anyway, soapbox, soapbox of why I make the decisions around that stuff the way I do.
Well, here's something I want to get to. You said you have a 10-year plan. I think I remember you, you had a thread about, about planning, right? And I— you definitely had something, something in the thread. And this is, this is kind of my beef with planning. So like, I used to be a huge planning guy. I used to be like, oh shit, you know, I'm doing this now. I want to be doing this, especially in college, because when you're in college, you know, the, the, especially for what I wanted to do, it was a very, very cut and dry path, right? You say, all right, if this is going well, I'm going to be here at this point in time. If it's going like shit, I'm going to be here. But by the end of it, if I want to get here, I got to do this, this, and this. Pretty, pretty linear sort of step, you know, gradual incline sort of thing. So, you know, with respect to a 10-year plan I mean, that is one of the things that like me getting out and doing this shit, I mean, I might have a year plan, pretty loose, pretty loose year plan, but like 10, I can't imagine that. So I mean, how do you, and I think one of the things that's most challenging for me about something like that is that I know, you know, it's T0, I know at T12, T24, T36, I'm going to have learned a lot of shit that I don't know today, right? Future Kyle hopefully is smarter than current Kyle, hopefully. And, you know, shit that I thought was smart, shit that T-0 Kyle thinks is smart, right? Maybe T-12 Kyle's like, that's fucking stupid. What was he thinking? Why was he doing that? So how do you— how do you account for the fact that, you know, especially someone like you who is so multifaceted, you're going to learn shit, right? So, so how do you, how do you formulate a plan that's so long-term but still accounts for the volatility and, and you learning shit? Yeah, yeah.
How old are you, Kyle?
I am 29. Yeah, yeah.
So, so I think that—
wait, why was that relevant?
No, no, I think it's— well, I'm going to try to make a point here. I'm trying to make a point. Sorry. Um, So I think that you are, I think you are pursuing, in my opinion, the optimal path for high achievers, especially in entrepreneurship, right? Like you go out and you try a bunch of stuff. You play jazz, right? In a world of people that want to play Bach and like you go out and just try a bunch of stuff, right? And you're doing that, like you're doing it with the lending, you're doing it with the, affordable housing, like you're doing with the STRs, like that is totally normal. Like, and I think, I think that's great. Like, I think you're doing it the right way. And I think you're totally right on to feel like you're still learning so much and that you haven't seen a lot of what's out there in the world. Like, and that, that it's premature to go and develop those kind of decade-long plans or whatever. Like at my stage in life, like Like, I'm to the point now where, I mean, I'm almost 20 years older than you, and that's 20 years being an adult. And then, you know, I'm well into middle age now. And it's a situation where, like, by this point, like, I've experienced, like, a ton of things. Like, I know I don't like the beach very much because I've been, I've been to the beach a lot. I like to go to the mountains. Like, but that kind of stuff, like, like, I didn't know those things when I was in my 20s. And the same thing applies to kind of the professional side of stuff. And to where, like, I think it's okay for you right now to be saying like, like, I can't really— there's so much, so much like kind of blank space that you haven't seen because you're still in that process of getting exposed to so many things, both externally and internally. Externally seeing the things in the world and then internally, like understanding who you really are because, you know, we're all wired very differently, but it takes us time to get to know ourselves. Through observation. So anyway, that's my way of saying, like, I think it's relatively easy and, and to, to say, okay, I'm 47 and I can set a 10-year plan because, like, I've gotten to know myself. Like, I feel like I know the world enough to where, yeah, I'm still learning things, but, like, I'm not seeing stepwise change in terms of direction or exposure to different things. Like, I know enough now to where at middle age it's like, well, this is who I'm supposed to be, this is what I'm supposed to do. And go from there. So anyway, I think we're— I'm trying to say, I think we're both right.
So, well, okay. So I know— so I like one of the cool— one of the awesome— okay, so one of the awesome things about that, right, as an answer is that it's— and I— so let's, let's talk about advice for a minute, right? Advice is one of my favorite things because I think that I've, well, I've been on the receiving ends of all kinds of it. And so most of it is complete shit, but some of it is not, right? And I think, and I think in particular, in particular, right? The hardest good advice to give is this kind of advice. It's this kind of stepping back, domain agnostic. What are you trying to do? Where are you trying to go? Forget about what exactly the domain is in this shit, right? But let's, let's talk about what you want to do and where you want to go. That is such fucking hard advice to get because the people who have really crushed that, number one, probably not going to talk to me. And number two, a lot of them, a lot of those people who have crushed it, who I have talked to, right, they're going to condition their advice on them giving advice to the sort of the median person, right? And that may or depending on who you're talking to, right, that may or may not be applicable. And so I found that that kind of advice, domain-specific advice, A lot of people can do that. Not that fucking— you just have to know something about domain, which I'm a big— and I'd love to know where you stand on this, but I'm a big seller of domain knowledge as a big value thing. I think that in a lot of domains, you spend 6 to 12 months in it, you're going to know a shitload about it. And then it comes down to the more generalizable skill sets, the more generalizable just business problem-solving abilities that you have, right? And, and that's going to tell whether or not you win or lose, not whether or not you're the biggest fucking nerd about, you know, drive-through coffee or whatever the hell it is, right? That's, that's my view. I'm a big seller of domain, so, you know, and you can look at my fucking background and say, yeah, this guy doesn't give a shit about domain, um, which is true. I think, I think, I think if you're smart, like, you can figure shit out, right? So number one, Where do you stand on that domain question, right? Does domain matter? Does it— you know, maybe you haven't— I'm somebody who doesn't have an affinity for domains. I don't give a shit. I just love playing the game. I want to know where you stand on that. Um, oh shit, what's my other question? Yeah, let's do the domain thing first. I want to know about the domain shit.
Uh, well, yeah, so the question is, to make sure I understand what you're asking, like, how, how important is it that Somebody has domain knowledge or that they stick to a single domain.
So yeah, I mean, how— yeah, I mean, do you— how do you— how do you think about domains, right? So like you did the drive-through coffee. I mean, as not as fuck-all to do with fireworks and software. So like, how did you— how did you pick that? Did you pick because you like coffee? Do you pick it like— how do you think about domains and how did you— how did you get confidence charging into it, right? I mean, okay, you got retail experience, right? But how did you get How did you get confidence going into it as somebody who wasn't born into it or hadn't worked in it or etc., right?
Yeah. You mean, I think so for their— so hilarious story for you. I'm actually not allowed to touch any of the coffee machines in the shops because the first time I tried to make myself a cup of coffee at one of our shops, I broke the machine. So they don't let me come back in because I haven't gone through any training. But that's actually by design. So I think that's point number one. Like, I think there are a lot of times are domains that are the same, but people don't really even think about it like as being the same. And people look at what I do as being really different. The things I do for each one of those companies is pretty much the same shit over and over again, right? Like I go to board meetings, I support the CEOs and make sure they're the right CEOs in there. When they have hard problems, like we talk and I help, right? Like that's, That is kind of this business tastes like chicken idea to me. And like, so I really see myself as focusing in a single domain of like small business, private equity, like that's what I do. So anyway, that's, that's kind of point number one.
So you think that business as an endeavor has enough commonality across domain, the problems generalize well enough, the skill sets generalize well enough If you've got an operator who knows the domain, you're going to be there when they bump into sort of maybe the harder, higher, higher level shit. And that's your jam anyways, more so than the ops perhaps. And that's, and that's, that's your approach.
Yeah, I would say so. But I mean, I think there's 20 to 30, sometimes higher percentage where there's domain-specific value that you create being in that that stuff, being in that industry. But I, you know, I think, I think that's different depending upon the industry. I mean, for example, if you're in construction, you know, or something where reputation really matters with subs and that sort of thing, um, you know, that can be more valuable than if you're just some yokels walking in and doing drive-through coffee. But, you know, I think the other thing that happens there is when you go through a new endeavor like doing a gap analysis and saying like, where do I need help? Is really important. So like everything I do involves partnerships. So like I'll look and see like who, who are what people can really do things well that complement what I need in order for us to win. So like when we started Dura, like I know I'm not a good operator and I don't— I know I'm not the right CEO for the business. So like my business partner I started with is a great operator. So it's like, okay, I'm going to go I'm going to go find the right people and kind of put that quilt of kind of people together and resources together to make it work. But no, I mean, I agree with you a lot. I think that domain is like super important, but to some extent it's easily hacked and commoditized to where like, you know, if you're smart and you care, you can be pretty good about learning some stuff really quickly. The core stuff of what business is like is pretty similar across all businesses of a certain size and type. So that's my experience, at least.
Yeah. Now it's, it's fascinating, right? Because when I, when I started doing this, I actually, I really didn't appreciate that. And so I was kind of like, oh, you know, I'm doing this thing, I'm buying crack houses and renting them out and refinancing them. And this is— I don't know. I don't know. I don't know if this is going anywhere. Like, eventually I have a bunch of crack houses. Great. But it wasn't clear to me, like the, and I think, I mean, you say it so well, right? The idea that business itself is sort of this thing and, you know, there are these skins, if you will, that these flavors, these spins you can put on it with respect to domain, but by and large, right? I mean, a lot of the problems and I see this now that I, you know, do a few different things, right? It's definitely, it's, yeah. It's right, you know, I'll look at a problem and, you know, like, like my COO who's probably been with us for 3 or 4 months at this point, right? He doesn't have the, the cross-domain stuff, but I'll be like, oh wow, this looks a lot like that other problem. We have to stay the fuck away from this, right? And he's like, oh, why? And I'm like, because this, this other thing, look, look what happened over here when we did this. He's like, that's totally different thing. No, no, bro, it is not a totally different thing. We're all people. You know, these are all businesses. This is the same— this is the same shit at the end of the day. I mean, unless you're— unless you're doing like some really heavy lift deep tech science stuff, which is crazy to me that people do that. I mean, I love all the VCs bitching that not enough people are doing that at the same time as they're funding just a bunch more shit apps. But, um, you know, it's— it's hilarious because I'm like, all right, I mean, I don't know if you guys can solve the business problem, and I don't know enough about science to know if you can solve the science problem.
Them.
So I don't know if I can write an angel check for this one, guys. Sorry. But, um, yeah, I think, I think it's right. I think if you're playing in sort of pretty established arenas, you know, and you're not trying to totally blow the world up, um, yeah, I think, I think there is a lot of commonality. And that was one of the— honestly, that was one of the coolest sort of, you know, fun sort of revelations for me was just being like, wow, a lot of this shit is the same. I can, I can literally, and I'm doing my own thing, so, you know, I don't have to call up the guy who runs my desk or compliance or risk or somebody. If I want to fucking do it, I'll just be like, tomorrow we're going to do it, we're going to try it, we're going to see what happens.
Yeah, I think that's great. I think it's, I think that's actually super optimal for this stage of your career.
So, and so for the, for the, um, to come back to, we made a little domain tangent there, but to come back to the what I was saying before, right, which is that big picture, high quality big picture, honestly, you know, pseudo philosophical advice, right, for people who want to play the game, want to play the game well, is fucking hard to come by. Um, and so for me to get a chance to shoot the shit with you, somebody who's ahead of me in the game, and you know playing it well, it's fucking awesome. It really is. Because that, that color— no, no, that color that you gave me earlier, right, where you're like, your shit is going to be more figured out in 20 years. Okay, I don't, I don't know that. That's awesome color. That's awesome color. That's really cool. I mean, if you could tell me like other bad shit to avoid, like how I'm gonna die or something like that, that'd be cool too. But like, you know, I, I don't know. I, I have a huge amount of appreciation and respect for that kind of advice because it is so so fucking difficult to get. So yeah, that is awesome. I love that.
So here's one thing, an anecdote that will blow your mind. So I, you know, I felt like my learning curve kind of hit a little bit of an inflection point, you know, a few years ago where just the number of moments per day where I felt like I learned something that was groundbreaking or anything more than anything more than just kind of a situational, like, educational— well, here's what's going on now— anything non-topical.
So stepping back from domain, things that you think— yeah, cracking nuts that you think are big generalizable solutions.
Yeah, like, I could only discover EOS once, or, you know, like, right, reading, you know, How to Win Friends and Influence People, that kind of like stepwise change things. I just wasn't, you know, I wasn't seeing those for anything except for kind of topical situational stuff.
Do you think that you get most of those from life or from, from reading or from other sources? Like, where do you think most of those come from?
It has shifted for me in the past 5 to 7 years to Twitter and one-to-one conversations. By and large, books, books are written for people who are I've read all— I've read the ideas in the books, let me put it that way. Like, once you read the books, like, they run out of ideas, uh, novel ideas. Um, and I kind of draw a 2x2 matrix of novel to me and useful. Like, there's a lot of shit that's in books that's just like whatever. Like, and there's people who love to read that stuff and they find it fun. I find it totally impractical stuff and unuseful stuff is totally boring. Um, so Anyway, yeah, that— the number of times I would get stuff like that from books is— it's few and far between. My consumption of books has gone way, way down.
That's fascinating. That's— yeah. All right, sorry, had to ask. On to the anecdote.
Well, I was texting with my buddy and I was like, I was, you know, I was talking about my experience at like a conference and I was like, well, it felt like it was 90% of the time what I was talking about or learning was the other person was getting more out of it than I was, right? And it was just like— and I was like, let's talk, talking to them afterwards, and I said, well, like, okay, yeah, this kind of makes sense. After doing nothing but nerd out on business for 25 years, eventually you learn some things, right? And you're just— that asymmetry is going to happen. So I'm not, I'm not, not pissy about it, but just that it's just the nature of learning. Um, eventually you kind of reach the extent of, of what's out there. And not that I know everything, but like I've seen a lot of stuff. So anyway, so I was so excited about all the stuff I'd learned back to my anecdote from like 30 to 45 that I was like, okay. And I started to go talk to some of my buddies who were in their 60s, which, by the way, it's also cool to be 47 because the 67-year-olds stop treating you like a kid. They just treat you like a peer even though you're 20 years younger. Whereas right now, I think when I would go in my 20s and go talk to a 67-year-old, they treated me like a kid still. It's really fascinating. Anyway, so I go talk to these buddies of mine And yeah, I'm kidding, table chili. And, uh, and I asked them, I was like, oh man, like, I have learned so much in the past 15 years from 30 to 45. Like, what am I going to learn from 45 to 60? Like, tell me, what are all these things going to learn? And I remember being at lunch with these two guys that were in their late 60s, and they just looked at me like I was an alien. Like, that's just the craziest question. And one of them thought about it for a while, and, uh, he told me, he's like, look, you're— you don't learn that much. Like the learning really slows down, but you do, you do learn that you're mortal. I was like, oh man, that's so depressing. Anyway, it was pretty much that. Well, yeah, it's just, it's pretty much that. I mean, my parents are going to tons of, tons of funerals. It's rough. It's rough.
Yeah, no, that's Yeah, shit. Well, I guess of the, of that sort of prime, that it's got dark, um, of that prime, um, you know, kind of learning per time period, right? What, what, what are the big things out of that where you're like, oh shit, that, that would have saved me so much pain a decade ago. And one of my favorite things about these kinds of lessons is someone in my seat might be like, oh, fuck that. I don't need that. And then obviously I'll hurt myself and I'll realize I did need that. But what do you think are like the big 1, 2 things where you're like, that was fucking game-changing for me figuring that out?
Yeah. So, so the one that comes to mind for sure is, you know, you run into topics sometimes and like you read it and you don't understand it, or somebody says something to you and you just don't understand it. And you just— it's like a black box to you. And let me— I'll give you an example of what a black box to me is. If somebody said, Michael, go set up a strategic partnership with this big corporation, like, I just— like, that is just something— like, if you ask me to go do that or talk to me about how it's done, like, I've read the books on it, like, I just do not understand it. Like, I cannot do that. It's not how I'm wired. Like, I'm just like, okay, when are we gonna make a deal? You know, like, I just do everything exactly wrong because I just don't understand it. Um, and what I started to see was, you know, there is— if you kind of draw a 2x2 matrix, there's known and unknown, and then there's understandable and not understandable for you. And there's like that quadrant of stuff that are unknown things that are just like a total black box for me. And there's lots of them, right? It's just like things where somebody tries to explain to me something I'm doing, like say a business coach is trying to tell me something I'm doing in a meeting and I just don't, I just don't even understand what he's saying, um, because it's a black box to everybody else. Their lens on the world enables them to see that thing. But like, there had— what I learned is there has to be a translation layer, like, for those things to unlock understanding for me. Because no matter what book I read or YouTube video I watch, unless somebody's there to kind of coach me through understanding those things, like, I'm never going to get it. And so there's lots of those things where You'll see CEOs, for example, who do things to piss off their employees. They have no idea they're doing it right. You know, and those are the things where it takes somebody to act as that translation layer, whether it's a CEO peer group or a CEO coach to kind of watch what you're doing and then tutor you through those things to really actually understand them. And that's one of the things when I look back on, man, I wish I was doing that in my 30s and early 30s and late 20s. Like I wasn't because like I was like, I'll just learn it all from books. And it's just there's things that you just can't understand unless you look at— unless you have that kind of translation layer to make it happen. So that's one thing that comes to mind.
Okay, and so, so it's, it's, it's the idea that, you know, you're not omniscient, you got blind spots, there's things you don't understand, and, you know, you should tell people you don't understand them, uh, that you're not—
you, you're not equipped to understand them unless somebody is going to really work with you to reach into your brain and help you understand them. And you may not even know you don't understand them. Yeah. So it's that level of— it's almost like coaching, coaching slash psychology is required to unlock those things.
Got it. It's interesting.
Yeah.
So that's, that, that's, that's an interesting one. I think that my, my version of that is that I used to, like an idiot, I used to ask why a lot.
Right?
Like some— like a counterparty, someone would do something that I consider to be real fucking dumb. And I, I used to say, oh, what the fuck? Why? Why would you do that? Give you a quick construction example, right? This is from a few years ago, but I had a— I had a killer electrician. Just amazing dude. I mean, so, so, you know, carpentry, sheetrock, flooring, painting, roofing, all this stuff we do in-house. But, you know, there are things that we sub out mechanical contracts, subcontracting, right? So heating, plumbing, blah, blah, blah, right? So electrical. And the dude, I mean, the dude killed it. I mean, he was— every time I went to the job, he was there. He did everything, you know, he was priced super competitively. And then I'd probably given him 6 or 7 jobs over the course of the year. And then we roll into the next year and he's not answering my calls.
He's—
and so finally I ask a buddy of his who's a plumber. I say, man, what the hell is with this dude? Where did he go? He's, he's a ghost. He's, he's not answering any of my shit. And he goes, he looks at me, right? And this is— this did not compute for me at all. He looks at me and goes, you gave him too many jobs. He has too much money. He has to go and spend it now. And I was like, I was like, I don't even, I don't even know what the fuck you're talking about, man. He went on some multi-month vacation. He was gone, right? I mean, I'm sitting, I'm sitting over here being like, what are you talking about? His business is crushing it. I'm giving him all this business. This is amazing. He should love it. And he, no, nope, nothing. And so, you know, I used to ask why. I used to say, why the fuck? And now I don't, now I don't. I said, there's some shit I'm never going to get. It's just not my, not my style, not my thing. I just, it just is. So I love that. That's, you know, so yeah, I feel you on the translation layer. I think one of the big, you know, one of the big, one of the biggest differences and I think just culture shocks for someone coming from Wall Street, which, you know, let's be candid, Wall Street's a bunch of Type A aggressive douchebags. Broadly, and coming from that world into, you know, the— this— the real world, let's be honest. Um, yeah, no, it's shocking because, you know, you, you, you step back and you go, listen, I, I actually have no fucking idea what animates people. I mean, why do people do this shit? I, I— and you just have to look yourself in the mirror and be like, I don't know. And what, you know, once I was able to do that it was way better because then I stopped wondering about it and I was just like, that was stupid. It happened. Let's figure out how to get around it now. But yeah, I definitely used to. I used to. Yeah, I used to wonder a lot.
Yeah, I dig it.
Well, cool, man.
Thanks for spending an hour with me and talking. It's good to get to know you, and I look forward to you being back on Twitter soon, putting more shit posts out. The world needs them.
Yeah, man, I've, I've been a little Twitter fatigued of late, but yeah, I'm definitely gonna— I'm gonna get back out there. Um, I appreciate you taking the time to, to do this thing, Michael. I mean, it's— yeah, like I said earlier, I mean, it really is awesome to sit down with somebody like you who's done all this stuff and has this breadth of experience and, and success, um, cross-domain, and yeah, pick your brain and see, you know, how you think about some of this shit like allocation and And, um, no, it's, it's, it's been awesome, and I appreciate all of the, all of the advice and all the wisdom. It's, it's invaluable stuff.
Yeah, I have no idea what I'm doing. So, uh, so people can find you on— people can find you on Twitter at Finance Guy 725, is that right?
Yep, that's, that's me.
Super cool. And then I noted your profile, it says—
closely spelled name.
If you need debt for your deal, DM me.
So they can DM me. They can. Yeah, DM, DM is sort of the more exciting route because you get to talk to me, which is— I'm biased, but I think fucking awesome. But yeah, otherwise you can go to our site and check it out. I'll actually drop a link to that in my bio so that people can do that. If you don't want to talk to me for some reason, I won't be offended. But yeah, this, this, this was great, Michael. I really, really enjoyed this. And yeah, you have a great rest of your week.
Yeah, man. Awesome job. I'm excited to watch your journey. Like, you're super smart and got a lot of grit, so you're going to do great. So really, really cool. You took an hour out of it. So thanks, man.
You're welcome.
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