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Matt Knight

"Fundings, VCs, News, Podcasts, Data, and (brief) analysis on the technology changing our built world" verticaltech.substack.com

  1. Aug 11

    The Alpha GP: Ep #1 featuring Dwight Dunton of Bonaventure

    Series: The Alpha GP Show Notes Summary: A deep dive with Dwight Dunton of Bonaventure. Special mentions * Company: Fannie Mae, HUD, Verizon, AT&T, Comcast, Gemini, Grok, Claude, OpenAI, Amazon, Azure (Microsoft), and Google. * People: Eric Sharpe. Transcript (Disclaimer: Please be advised that this transcript may contain unintentionally confusing, inaccurate, and/or amusing transcription errors.) [00:00:00] Matt Knight: Hey guys, kicking off a new series here around innovative and interesting GPs or deal sponsors. People that are fundless sponsors or have a fund and are investing in property around the US and around the world really, that are doing things in a unique, innovative, or maybe just a paranoid way where they think AI’s gonna take their job. And so this first one, we’re gonna have Dwight from Bonaventure. He is in the DC area. Their portfolio, I’ll let him tell you about. But we don’t even talk about AI till two-thirds of the way into it. So just know we talk about lots of other stuff. But this is Dwight from Bonaventure talking about their take on innovation and tech strategy. Hope you enjoy Matt Knight: All [00:01:00] right, Dwight. Glad to have you here, man. Excited to get to know you a little better and have you on the podcast. Thank you for being here. And I think it’s always smart to start with where’d you come from? What is Bonaventure? How did it get started? How long have you guys been around? Give us the key stats, and then we can start chasing rabbits. Dwight Dunton: Yeah. Matt, so excited to be here. Thanks for the invitation. Bonaventure got started because we needed to solve a complex real estate problem. Our family was fortunate to own a piece of a building from the 1960s. Our partners became a huge REIT, and they one day in 1999 told us the property was in a C location and needed $5 million of capital improvements just to keep the lights on, and we didn’t have $5 million. And so that was the birth of Bonaventure, and the rest is history Matt Knight: What’s Dwight Dunton: that lead you Matt Knight: to now? I was gonna say, what’s the portfolio look like Dwight Dunton: and where- yeah. So that, over the last 25 years, what started off as helping one family, our family, has now grown to [00:02:00] about 500 families who are all trying to build long-term wealth. We help them. We have five platforms, about 400 employees, $3 billion of assets under management. So it’s go- grown a lot from that humble beginning. Matt Knight: And you say asset preservation, I think evergreen funds and REITs that are doing dividends. What’s the structure look like? It sounds like it started as a fundless sponsor, but I think you have REITs now. Walk us through if we were to give you capital, what does Dwight Dunton: that look like? Yeah. So I think our kind of investment thesis across all of our different products is that housing is broken in the United States, that where people want to live and the ability to produce housing are disconnected. And from there you have the real estate cycle and the economic cycle creating opportunities, and we seize those opportunities through a variety of different wrappers because we understand that each investor needs slightly different things. So that could be a single asset investment, that could be a development deal, that [00:03:00] could be an OZ fund, it could be, as you mentioned, a perpetual life REIT. We have a REIT that has about $1.3 billion of assets in it. And so again, it’s all about creating alignment around the economic opportunity and helping connect that capital to investors who are building for long-term wealth to afford their long-term dreams. Matt Knight: One of the things I’ve heard about you from our mutual friend Eric, is you have this ability to think from first principles. Like just because something was done one way doesn’t mean we have to do it that way. And so I’ve, one, I’m curious if you think of yourself and your firm that way, and then two, if so, give us an example of that, something that kind of other people may not do or just take for granted that you guys have reimagined. Dwight Dunton: Yeah. I think that’s a good description, but I don’t know that it started off that way. It was simply, I didn’t have any real estate experience when I started the firm, which is crazy to be 25 years old and buy a 378 unit apartment complex, convince Fannie Mae to lend me, I think it was 17 million, and let me start a property [00:04:00] management company. So I, I had no perspective on this is how we do it or you can’t do that because I had no experience. And we brought that forward, which is we challenged everything. When somebody says, “You can’t do that,” we’d really step back and ask why and really get to the root of it, and have found that so many industry conventions were brought about for one good reason, but then have been misapplied for years and years. And so for instance, we became one of the largest borrowers with HUD, and we would go to conferences and people say, “Why would you waste time with HUD? It takes so long.” It takes slightly longer, doesn’t take so long, and if you run it concurrently with your zoning and entitlements and getting your plans done and your permits, it actually adds no time whatsoever. And so the end result is most people have avoided HUD because it, quote, “takes too long.” We found it’s about the same amount of time, but we got these amazing outcomes, which are loans that have l- are gonna last for 40 years. [00:05:00] We reduced our interest rate risk. We had no personal guarantees. And so that’s a, just a simple example of we challenged the convention conventional wisdom of everybody that, quote, “knows what they’re doing in development” and said, “Avoid HUD at all costs.” Matt Knight: Yeah, I don’t think you know this about me. My first job out of college was lending HUD money, doing the 223and 221(4). So I was- Dwight Dunton: Ah. Matt Knight: I was baffled like you, where it’s like, “Look how cheap these rates are. Look at the amortization.” These are... This is great debt, and people are like, “Eh.” Yeah. Dwight Dunton: Well- Matt Knight: “Okay, whatever you want.” Dwight Dunton: And so I... Good for you. You get it. I think what I discovered, because I’m like, people are fairly rational. It seems overly convenient to say it’s too hard. What I figured out was that most people’s business plan in multifamily development is they build buildings, collect fees, and they collect lottery tickets, and those lottery tickets take the form of promotes, and the key is to scratch it off as quickly as possible to see if it has value. If it doesn’t, you move on to the next deal. [00:06:00] And HUD is not compatible with that because there’s the prepayment penalty for 10 years. And so if you’re in the business of collecting fees and lottery tickets, HUD is definitely not the ideal choice. And and that sounds really self-serving to say that to an LP of why you said, I won’t do a HUD loan,” but it sounds way more convenient to an LP to go, “Hey it just takes too long,” versus, “It’s not in the pr- the sponsor’s economic best interest.” That’s what I discovered as to why people have just continued to throw out this misunderstanding that it, quote, “takes too long.” Matt Knight: Yeah. I think that’s fair. And I think there’s another example you guys have of first principles where you were looking at tenants and their experience with internet service providers, and you guys have built something around that, correct? Dwight Dunton: Yeah. That is a great example. So I was walking one of our properties and, I walk behind the buildings, through the buildings. I wanna see everything. I just don’t want the tour that the staff has decided to prepare for the CEO ‘cause our staff [00:07:00] is awesome, and there’s always something that can be improved, and I wanna help discover that ‘cause they’re there every day, and they might miss something. So one day I was walking at one of our properties, and I saw the side of the building with all of these wires hanging out of this box that was, like, had the door bent off. You couldn’t even close it. And I was like, “Is that our cable box?” And they’re like, “Yeah, the cable contractor comes to hook up and disconnect internet, and then they don’t bring the key back, and then they leave it open, and then some kids open it, and then they rip all the wires out, and all the internet goes down.” And I was like haven’t you asked them to stop doing that?” ‘Cause it ultimately is bad for the internet service provider, which was usually a cable company or a large telecommunications provider. They’re like, “We have, but you know what? They just don’t care,” is what it seems like. And that was the moment where I said, “Enough,” because I had poor experience at my home. Everyone I know has waited for that three-hour window and not had the technician show up, and I was like, “There must be a better way.” So I [00:08:00] spent about a year saying, “How do I find that better way?” And there was a lot of internet service providers that provide internet service in a multi-family environment. Huge improvement to what the incumbent, monopoly had, but still left a lot to be desired. So we finally said, “We’re gonna have to build this ourselves if we really wanna get the best experience for our residents, the best experience for the property staff, and provide the best value to our building,” because, if you look at it, there’s two values to the building. One is these internet service providers make a ton of money. If you pull apart Verizons or AT&T or Comcast and look at how much money they are making and minting, the gross margin on internet, high-speed internet is through the roof, which then makes you wonder how can they not give b

  2. Jul 30

    Into the FIRE: Ep #6 with Stephanie Gubiotti

    Series: Into the FIRE. Show Notes Summary: Into the FIRE with Stephanie Gubiotti, Advisor - Foundation for Innovation in Real Estate (FIRE) and the 2026 Academia Calendar, the next Emerging Manager call, fall events, and FIRE Summit 2027. Special mentions * Company:  RealPage, Cherre, Burns Management, Inman, FIRE, Magic Leap, Oculus (now Meta Quest), Apple. * Events: RealWorld, Blueprint, CREtech, OPTECH, RETCON, HIS, FIRE Summit, * RETTC. * People: Bruce Lohman, Michael Beckerman, Peter Rosecrans, Martin Kelly, Anne Hollander,  Paul McCartney. * Universities: Notre Dame, Harvard, MIT, UC Berkeley, Stanford, Emory, UGA, OSU, Princeton. Transcript (Disclaimer: Please be advised that this transcript may contain unintentionally confusing, inaccurate, and/or amusing transcription errors.) [00:00:00] Matt Knight: So first, let me apologize that this podcast is a bit all over the place, but Steph and I get on tangents, and we just keep going because... In our defense, we have a lot happening this fall, and fall is our busiest season. So another episode of Into the Fire with me and Steph, but just understand we will have more to come in the fall with more names and more specifics. But this will give you a bit of an idea of what’s happening, where we’re going, and if you wanna get involved, you wanna help, you wanna support, or you wanna just see us, hit us up ‘cause we’re always down to connect. Enjoy it Matt Knight: We’re looking at fall, planning our trips. Fall tends to be crazy. I don’t know how much you remember from last year, but fall is just bonkers. So [00:01:00] probably good to talk about what’s coming up, what we have planned, and curious how you’re feeling about it here sitting here in year two Stephanie Gubiotti: first, fall is my favorite season. It’s the best, and I’m really excited to get on campus this fall, connect with students. Yes, it’s a busy time, but it’s also really fun, and I enjoy being able to have those bursts of busy. So for me, it’s nice to have this really busy part that we’ll be having for a little bit, and then we’ll get into the lull of the holidays, and then we’ll pick back up again and early next year as well. Matt Knight: I’m into that. And, I’ll just add in for campus, it looks like Cal and Stanford are gonna happen. It looks like MIT and Harvard are gonna happen. Looks like Emory and UGA are gonna happen. And other than that, it’s a bunch of maybes. Do you have an update on OSU, or is that still TBD? Stephanie Gubiotti: OSU is still [00:02:00] TBD. They’re redoing a lot of their programming, so we’re waiting to finalize schedules. So as soon as they get back to us, we can lock in on some of these things. Matt Knight: Yep, and Notre Dame’s out there. Shout out to Bruce if you’re listening. Princeton’s out there. Shout out to Chase if you’re listening. So there’s a bunch. We have, I don’t know, a dozen now schools that are in our radar. And if you’re listening to this, I think w- what you should know is we have free tickets to all these events in the fall for these students, up to a certain number. So if you’re interested in coming, if you’re a student or if you know a student, send them our way ‘cause we have cohorts coming and we can do things with them, and, hopefully they’re over 21. But if not, we’ll figure out something anyway. But, that’s sort of academia for me this fall is a blitzkrieg of basically October events on campus Stephanie Gubiotti: Yeah, it is convenient with CREtech being in New York though, so, I’m hoping that we’ll be able to get a good turnout from our student population there. You know, they’ve been very, very generous [00:03:00] with giving us a large portion of ticket allocation for students. So, if you’re a student specifically and able to get to the New York area, let us know. Matt Knight: Yeah, if there’s anyone who cares more about students than us, it’s Beckerman, so shout out to Michael and his team at CREtech, ‘cause they do a great job. Stephanie Gubiotti: Yep. Matt Knight: But speaking of events, we got, Real World coming up in a few weeks. We got Blueprint, CREtech, and Optech in that order, and have all kinds of programming around both, right? Stephanie Gubiotti: Yeah, yeah. I’m excited for you to experience your first Real World or your first software conference for a PMS, so it’ll be fun. Matt Knight: If you say so. I, I’m, I am intrigued enough to fly there and spend my money on it. How about that? I’ve- I’ll see how it goes. Yeah. And I’m excited about RealPage. I think RealPage is doing... I think RealPage is trying really hard to do some cool things, and I think the jury is out on what they will or won’t do, but I love where they’re going. I love that they’re making an effort, you know? And there’s a lot of companies that can, [00:04:00] just be big, and I don’t think Dirk and his team, are satisfied with that. I think they really wanna push the envelope, and I respect that. That’s not an easy thing to do with a company RealPage’s size. So I’m... I was being glib earlier. I am interested in going. Stephanie Gubiotti: Yeah, I think it’s gonna be great. I also... They have some really interesting speakers lined up, and I, I also think their acquisition of Cherre is really fascinating. So anyway, I agree they’re doing cool things. And after that, we’ve got Blueprint, where we’re working with Martin and the Inman team to put together some programming there. We’ll be doing some tours, working on some really fun stuff for our group. Let’s see. Next week coming up soon we’ve got our next emerging manager call, which is super exciting. We should have a pretty good turnout for that one. We continue to grow and scale that group, which is also great. Matt Knight: Yep. Peter Rosecrans of Burns Management out of New York is gonna be our guest speaker, and I’ve personally spoken to a dozen of our EMs in the last week, [00:05:00] and many of them will be on, ‘cause we have lots of new things we’re doing with them. So that’s, that is, seems to be accelerating more than any of our programs. Our EM program is really picking up, I think. Stephanie Gubiotti: Yeah, I think there’s just such a need for people, especially those small to mid-size operators who really need that level of guidance and support, and just somebody to say, “Hey, don’t spend your precious limited resources trying to solve a problem that we’ve already solved.” So Matt Knight: Amen to that. Maybe it’s worth updating that I’ve been spending time on comparative tech stacks, just putting people’s tech stacks into a document and saying, “Here’s my PMS, here’s my back office, here’s my tenant screening,” and just showing to where we can compare and contrast and have them compare notes and people that have the same back office or, you know, overlaps or... What’s interesting to me as I’ve started doing this is seeing where AI is replacing vendors. Because a lot of the ones, you’ve seen this, a lot of the ones I’ve started stacking have 40-plus vendors. Yep. And I [00:06:00] wonder if they’re... But a- academically, you wonder if there’s some steady state where we get down to 15 vendors and they’re all AI native and they all do, you know, half a dozen things well. I mean, that’s kind of in the PMS playbook for 20 years, right? Stephanie Gubiotti: Yeah. Yeah, I think so. Matt Knight: Yeah. So anyway, that’s EMs. And like Stephanie said, there’s a lot. We have private tours at these shows. We’re gonna have happy hours. Got some custom intros I know I need to make, but it’s gonna be... We roll out the red carpet at these events, ‘cause there’s only, three of them in the fall, and- Yep Maybe RETCON and HIS in the spring. So it’s not a ton of events we do this at, but since everybody’s gonna be there, it just is a great way to, to concentrate everyone in one place for 48 hours, and then we all go back to doing our day jobs. Stephanie Gubiotti: Yeah. Do you wanna talk about some of our Fire City tours that we’ve been chatting about doing? Matt Knight: Sure. Go for it. Stephanie Gubiotti: So we’re looking at sending either myself or Matt to various cities, sometimes both depending on our [00:07:00] schedules, to be able to meet up with our network and be able to bring people together. We’ll host some sort of a happy hour, and likely after we’ll do some sort of an executive dinner. So we’re still shaping what those will look like, but we’re trying to kind of align timing. If we’re already in cities doing campus tours, you know, and we’ve already got a group of executives coming to meet with us to speak with students, it would make sense for us to kind of do a dinner at the same time. So we’re thinking through those types of things to start kicking off in the next few weeks here. And we also did something super exciting. Do you wanna do the big reveal about what we decided on? Matt Knight: No, you can do it. Stephanie Gubiotti: Okay. I’ll be okay. We decided to do our Fire Summit next year at, in Laguna Beach, California. So we did change locations, and we are planning to ideally, uh, reserve the entire resort for our group. So very, very, very excited about that. I [00:08:00] won’t list the name of it out loud, but I’ll just say that it’s in Laguna Beach May 5th through 7th, and it is our exclusive off the record conference that we do once a year, where we... I like to call it we work on the industry instead of in the industry, where we bring together people from different areas to collaborate, brainstorm, learn from one another, and solve real problems. And we’re also tapping into working on a new housing affordability initiative. So I think it’d be great for you to talk about that and what you’re doing with Anne a little bit. Matt Knight: Yeah, it’s still early. Anne kno

  3. Jul 21

    PropTech Chatter Ep #11 - featuring Dom Beveridge of 20for20

    Series: PropTech Chatter. Show Notes Summary: A deep dive with Dom Beveridge of 20for20 on the three most valuable events this Spring for ConTech. Special mentions * Company: FIRE, PropTech Angel Group (PTAG), John Deere, * People: Steve Lefkovits. * Events: AIM, CES, RETCON, FIRE Summit, Blueprint, CRETech, RealComm, OPTECH, Apartmentalize, NMHC, FLEX Conference. Transcript (Disclaimer: Please be advised that this transcript may contain unintentionally confusing, inaccurate, and/or amusing transcription errors.) [00:00:00] Matt Knight: Hey, guys. Matt here. Another podcast episode, this time with my friend Dom, whose accent is much better than mine. But we’re talking about events. I thought this was timely to reflect this summer on what happens in the spring as we look forward to the fall, and he’s got a really interesting take on it that, is a perspective I don’t have. So listen to this 15 or so minutes of me and Dom waxing on spring and other events Matt Knight: All right, Dom. Thanks for being here, man. I appreciate the time. I know we saw each other a bit this spring, but I thought it’d be good this summer to reflect back on spring events in real estate construction tech and kinda talk about why those matter. How does that sound to you? Dom Beveridge: Sounds great. Thanks for [00:01:00] having me. Matt Knight: Yeah, man, I think this is important. If you’re young or you’re starting up a startup or you’re new to the space or maybe a student, I think it’s good context because, all of us have limited budget most of us have limited budgets, and so knowing which events are for whom and what they’ve... how you can benefit from them and who they’re targeted towards and who shows up I think is super useful, unless you disagree with that Dom Beveridge: No, I I agree completely. I I have quite a lot of conversations about that very thing as well. Matt Knight: And maybe a good place to start is maybe run us through your spring lineup of events, and then I’ll go through mine, and we can talk about overlap and maybe reflect on what each one maybe strengths and weaknesses for the ones and where we think they’re best fit. Dom Beveridge: Yeah. I tend to ration myself to events that I speak at, right? So I’ll usually go to some number of client conferences or, y- just user conferences for companies that I work with. And for the most part, I try [00:02:00] to focus on the public events, the commercial events that where there’s an opportunity to speak, to develop some content and so on. And my... the first sort of big public event I do each year is usually AIM. AIM is a really interesting show. It’s been growing for quite a while. Very, a very tried and tested formula. It, it built its reputation around marketing, but for the last few years, it’s been growing its executive presence quite impressively. They had a really good attendance this year, very interesting audience. And yeah they try to... steve Lefkowitz is the, probably the best curator at event content in the industry. He really pushes to have kind of very current kind of stuff. He wants he wants whatever is new in the industry to be on the stage at his show. And yeah, he’s built a community around that that event. So it it’s fun. It’s a great place to go connect, but it’s also got quite a commitment to [00:03:00] learning about it, and so I like it for those reasons Matt Knight: Yeah, I I’ve spoken at AIM, and I think very highly of Lefkoe and Dennis. And I wanna come back to AIM ‘cause it’s... you mentioned something that I’ve had a suspicion about for a while. But for me, I’m similar in that I tend to filter for things where I either have a direct speaking or content line or I have something unique that I can add to it, versus just I need to go to Vegas again. I don’t have time for that. But on the other hand, I do have things I go to where I’m trying to discover. With what I do with the foundation, I go to CES every year because I wanna see what’s happening in consumer electronics, ‘cause a lot of B2B companies are there and selling their hardware. A lot of countries come to that, and here’s what’s innovation in Germany and Denmark and Korea. And so I do CES in Vegas every January just to see what’s even possible in the world of technology, and then it’s my job to bring it back to the real estate and construction industries. And then the very next month, there’s one called IBS, the International [00:04:00] Builder Show, which is a very similar flavor, but it’s all home building tech. And so same thing, is how can I take what the most innovative home builders and suppliers and OEMs are doing and bring it into multifamily or office or retail or hotel, right? So I do those two generally just to see what’s even possible and how I can bridge the gap between those industries and our industry. And then I also usually go to RETCON, which is a very, I would call it analogous to Blueprint and CREtech to a degree, but it’s in the spring. It’s a different company. It, it would have a similar vibe to those two, but it happens every spring. I think it was March this year. I don’t remember. But it was in Vegas again this year, and I did those three before doing my event in La Jolla right after AIM. So that’s my spring is the two where I go scout. RETCON is a down-the-fairway PropTech company, and then my event right after AIM, which is in May. Those are my four, give or take. Dom Beveridge: Yeah, no, I’ve been to RETCON before. The the problem with that show is I live in Texas, and [00:05:00] they always hold it during Texas spring break which which means it’s it’s less popular with with people from the Lone Star State. But no, I’ve been there before and and have generally good feelings about it. Matt Knight: Yeah, and with, to your point on AIM, I think the world of Lefkoe. He’s been in my angel group. He’s one of the greater minds in our space, and a great... He’s got a great voice, got a deep one. He doesn’t have your buttery British accent, but he’s got a really good speaking voice and a good presence, which I always appreciate. And I was on the board of his MICA Conference when it was in Atlanta, and when he did the FLEX Conference in SF, I went to that. So I agree with you on the top-tier, thoughtful curation of content and people. What I have hesitated is I’m not a marketing person, and of the stuff I touch, 10% of it is marketing. Top of funnel leasing strategy, website content, all of that’s great, but it’s 10% of the stuff I do. And so I’ve held off on going recently, but I’ve heard what you said is that it’s become a lot more than that, and I hear the same thing about Real Comm. But I’d love for you to expand on that a little bit where, [00:06:00] yes, the CMOs and the marketing folks come, but it’s evolved into blank. What is that blank to you? Dom Beveridge: Yeah. I’ve been going to AIM for probably about like 12 years or something like that. And so it always used to be... So when I used to sponsor it as a, when I was the CMO back in the day, like I, I used... When I used to sponsor it, I used to primarily see it as a very good sort of see and be seen kind of conference. Like it was a, there was just this big social network around the the conference. They’re not the people that ink deals if you’re a software company, but they’re but they’re people who are usually in the room when the when w- when your product is being discussed. So I had that kind of I had that kind of perspective on it, and it was worth doing for those reasons. But nowadays, like where I tend to show up at conferences basically just to network, just to keep connected with with people that I work with or who I, who at some point I will need to answer to have them answer the phone to me. That’s the big objective for me in most of [00:07:00] these conferences. What’s really happened over the last probably two or three years is that they’ve been running this C- a COO forum where they do I think like a half day of of behind closed doors meetings with a group of of operational leaders. And that h- is being increasingly successful because, when you flick through the attendee list for AIM, it’s now really good. So again, for someone like me it’s now an excellent place to to go listen to a few new ideas, go to a few events by the beach, bump into multiple of the people that I y- that I tend to build my network around in this very sort of convivial y- event. And so yeah, it’s it’s this combination of they’ve been making the audience more senior. They keep trying to push the envelope on content, so it’s not all about marketing. And the, just the the general level of enthusiasm for the event means that, y- social events are really well attended. [00:08:00] And no it’s it’s a really great use of a couple of days in at the beginning of May each year. Matt Knight: Never a bad time to go to Huntington Beach. And I don’t know if you’ve heard of Real Comm, but I’ve heard the same about Real Comm. Do you know that conference? Dom Beveridge: Yeah, I actually, I spoke at Real Comm last year. I did I did a session when it was in Savannah which is a great place to hold a a conference. I wish we could have more of that. But yeah, that, that was good, but it’s very much commercial real estate. Residential is very much out at the fringes of that event. Matt Knight: Yeah, I guess s- to me, Real Comm started, from what I understand, as an IT conference, right? It’s Excel spreadsheets and CRMs and stuff that’s more for directors of IT. But that was, like, I... 20 years ago. That’s an older conference. Older in terms of prop tech, but not old in terms of all conferences. Where it was procurement and IT best practices, and it’s evolved recently where a lot of startups say, “I gotta go to Real Comm,” which I think is usually in the summer. It might be right

  4. Jul 10

    VC Unfiltered: Ep #3 featuring Courtney Cooper of Alate Partners

    Series: VC Unfiltered Show Notes Summary: This episode of VC Unfiltered covers Founders, Investments, and ConTech Portfolios, with Courtney Cooper of Alate Partners. Special mentions * Company: Dream, VTS, Klick Health, Atticus, PadSplit, Mave, OwnRight, Unity AI, Claude, Gemini, and ChatGPT. Transcript (Disclaimer: Please be advised that this transcript may contain unintentionally confusing, inaccurate, and/or amusing transcription errors.) [00:00:00] Matt Knight: Hey guys, if you don’t already know Courtney Cooper, then shame on you. She’s awesome. I’m gonna talk to her here for a few minutes about Alate and Canadian PropTech. We’ve known each other for a minute, and she’s just working on cool things and is just a wonderful person to know. So enjoy this time with Courtney Cooper Matt Knight: All right, friend. Thanks for being here. I appreciate it. I guess you and I met more than five years ago. It’s been a while, but I’d love, if you don’t mind, can we start with who’s Courtney? What’s your background? Talk to us about Alate. What’s going on now? Let’s set the scene before we get too far down rabbit holes. Courtney Cooper: Yeah, I joined Alate in [00:01:00] 2018. So that, Alate is a vendor fund that invests in early stage prop tech in Canada and the US. Before that, I spent my whole career at the intersection of real estate and tech. I started at Dream, which is a large owner/operator developer based in Toronto, but has assets across North America and Europe. And I worked with them on a big technology overhaul. We were building some of our own software. We were implementing third-party software. And that was really when I got introduced to software development and the opportunity of technology in the industry. And then, led me I took a little bit of detour, but led me back into prop tech when I joined Alate. Matt Knight: And tell me about Dream. What’s the portfolio and scope of Dream, and how did that affect kind of what Alate did? Courtney Cooper: Yeah, so Dream is they do a little bit of everything, and what they do depends on the year that you that you’re looking at them. So they’re about 30 billion in assets right [00:02:00] now. They have, they own offices, industrial. They do, d- they do development of master plan communities. They have land, housing. They do condos. So it really kinda has spanned a bit of everything, and for me was an opportunity to learn about all aspects of real estate early on. And we were... some things we were doing, we built a y- we built a platform, an internal platform for property management and leasing, doing some of the lease workflows that VTS would do now. We were trying to bring together everything that anyone needed to know about the property. We, I helped implement some software on the home side. I think they they’ve transacted large portfolios. They’ve continued to expand the business. And so I think I was there 2011, 2012 until 2016. That was when I was initially involved with them. And then Dream is one of the co-founders and LPs of Alate, so I’ve been working with them since 2018 and seeing the business grow and change and seeing their strategy [00:03:00] on technology change. They, some of the things they built lasted. Others were cycled out and replaced with the new technology providers that had spun up since we started that initiative. And it’s been cool at Alate to actually get to invest in some of the ideas that we had in, in 2012 to 2015 when we were trying to build things ourselves. Matt Knight: Were you involved in that building of things, or were you more tangential to it, just out of curiosity? Courtney Cooper: No. I was core to it. I wasn’t a software developer or on the tech team from the start, but we did it in sort of two ways. We hired a consultant to help us do a big analysis of our processes to understand what we were doing that we didn’t need to do and how we could improve. And so we did an eight-week mapping exercise where we brought all the stakeholders together in all the different workflowsand identified what were the biggest opportunities on the process side and technology side. And so I was in all of those meetings and part of hiring the consultants and project management for that [00:04:00] process. And then we were working with one of the board members who’s the CEO of Klick Health, which is a large marketing company for healthcare and pharma, and they had built a lot of internal software. So we were working with the VP Of corporate services who ran all the operations side of it. the board member helped hire that whole team and help with the strategy, change management, project management, pitching in where there was gaps. ‘Cause as we’re building a team like a startup, there’s a lot of things to do and not people to do it. So I was a product owner on one of the products and helping really bridge the gap there. So that was really my sort of introduction to being around software development and on that team and yeah, learned a lot Matt Knight: Got it. And then, I know we have talked about this a lot off the recording, but how do you think about Alate in the pantheon of real estate construction tech, proptech funds where, is Canada, is Dream, is there a unique angle on here’s how we do it different? Because the thesis, as is we have the users of the technology as our LPs, so [00:05:00] it makes us vet and deploy better. How do you think about what Alate does or did relative to kind of other funds? I’m curious. Courtney Cooper: So Dream is one of our... they co-founded Alate and was part of the initial capital, but then we raised a fund and brought in other LPs. So all of our LPs, for the most part, have a strategic real estate business or focus. And so we do have that sort of lens that we work closely with our LPs, and they can help us on testing out ideas and software, although we don’t have a tied relationship. I think that we try to when we’re doing diligence, we’ll involve people in our network and our LPs to help vet what they’re doing and the ideas and help us understand what the objections might be in the industry. But we’ve generally seen that real estate companies adopt at their own pace, and they have different priorities at different times. And so many of our companies we’ve invested in- involved partners during diligence, but then, some of them adopted immediately, others it took a year or two or three and they [00:06:00] just ended up using them when that project came around. So we definitely work really hard to help our portfolio companies on getting in front of the right people at the right time. That starts with our LPs, but also all of the relationships we have in the industrythrough our experiences and our extended team and LPs. And so we work really hard to try to tap into that and make introductions. But also people like you and being part of PTAG, I think there’s a lot of connections that startups make with other founders, and so we work as hard as we can to deliver on the promise of actually making those introductions and helping with BD where we can and being a good partner. And, I think that other funds have similar approaches. And I think we try to deliver on it Matt Knight: And how do you think about portfolio construction? Being Toronto-based and, there’s been some cross-border let’s say media recently with coming in out of the US, but obviously you’ve built a good portfolio. Atticus is a stud, like I know a lot of your investments, but talk to me about portfolio construction, how you [00:07:00] thought about that, how you’re thinking about that. Lead, co-invest, deal size. Just give us a flavor for what’s in Alate’s portfolio. Courtney Cooper: Yeah. We primarily do early stage, so for us, we’ve entered at pre-seed to Series A. We’ve got some other later stage investments through acquisitions and other sort of unique opportunities. But bread and butter would be a million, 500K to a million and a half first check into, normally pre-seed, and seed is where we get started. We obviously have a soft spot for Canadian founders, and we’ve made investments in a nu- about half our investments are Canadian. Maybe slightly more, but around half i- in Canada, and we love Canadian founders and have seen great companies coming out of Canada. But we also invest in, in the US as well and have built and invested in great founders there. We so we don’t g- geographically, it’s kinda ended up 50/50, but that’s yeah, but it’s much more about the company and the stage and if [00:08:00] everything lines up for us to be part of the round. And we’ve done a mix of residential, commercial and construction, so we haven’t been bound by by a specific asset class. Matt Knight: Yeah, I was gonna ask about that because certain funds have certain strengths. Do you feel like you guys are pretty utility players across ConTech, resi, and commercial, or is there one where you feel like you have more depth than others? Courtney Cooper: touch residential and commercial, and we’ve done a few on, on the construction side, but we’re not as... we’re construction isn’t... There, there’s funds where construction is their core focus, but a lot of our LPs obviously build a lot, and so we’ve been successful in making connections there. But I would say that we have less inve- if you look at our portfolio, we have less on the construction side than the others. Matt Knight: Sure. Yeah, me too. What about wins? Any big wins, gains, portfolio brag you wanna get on the record before we talk about lessons learned? Courtney Cooper: Oh, man. I feel like this year we’re, there’s a lot of momentum in the portfolio. I think that it’s been it’s been an interesting few years. But no, a lot of our companies are [00:09:00] doing well. PadSplit you mentioned. They’re doing awesome. They’re the largest co-living platform in the US, and, it’s incredible

  5. Jun 18

    Into the FIRE: Ep #5 with Skyler Chan

    Series: Into the FIRE. Show Notes Summary: A special episode of Into the FIRE hosted by Stephanie Gubiotti, Advisor - Foundation for Innovation in Real Estate (FIRE) and the Emerging Manager Program, featuring Skyler Chan of GRU Space. Special mentions: * Company:  FIRE, GRU Space,  NASA, SpaceX, Blue Origin. * Events: FIRE Summit. * People:  Matt Knight, Ashlee Vance, Elon Musk. Transcript (Disclaimer: Please be advised that this transcript may contain unintentionally confusing, inaccurate, and/or amusing transcription errors.) [00:00:00] Stephanie Gubiotti: All right. All right. Today we have something a little bit different. Welcome to Into the Fire. We have Skyler Chan, and I’m your host today. Instead of Matt, you’ve got me, Stephanie Gubiotti. Stephanie Gubiotti: So welcome, Skyler Skyler Chan: Thanks, Stephanie. Yeah, excited to join today. Stephanie Gubiotti: Yeah. So for those who don’t know you, I’ll give a little quick rundown. We had the opportunity to meet in person in La Jolla, which was fantastic. Thank you so much for coming and speaking with our group and spending time with us. Skyler Chan: Thank you for hosting. Yeah, it was a great time. Stephanie Gubiotti: Yeah. Super excited to hear about the things that you [00:01:00] have going on. But Skylar is the founder of GRU Space, and his mission is to build hotels on the Moon. So Skylar, do you wanna talk to us a little bit about what the latest things are that you have going on, and any latest and greatest updates about the Moon Hotel? Skyler Chan: Yeah. Thanks, Stephanie. And so as Stephanie mentioned, we’re the company building the first hotel on the Moon. Our mission is to make humanity intergalactic. And so what that means is we start with building cities on the Moon and Mars. Working backwards from this vision, we’ve identified that building a hotel on the Moon is the fastest way to activate this feature. And so right now our main focus is building the technologies and systems necessary to enable us to live off of Earth. One of the key theses is that in order to do this, we need to decouple our dependency from Earth, and we need to be using resources on the Moon and Mars and beyond [00:02:00] locally. The reason why is because it’s very expensive to have to bring all the material from Earth to the Moon. So what we’ve developed is a series of technologies that enable us to use resources on the Moon. We’re starting with a machine that we’re sending to the Moon as early as next year. It’s a payload that our team is developing, which will make the world’s first bricks on the Moon. And really what it’s to do, it’s to prove that we can use resources on the Moon to create products. Humanity has never made a product on the Moon before, ever. And once we figure out how to make a product on the Moon it’s like the discovery of fire. You can argue it’s the Promethean moment. No pun intended here. And that is going to enable a whole Cambrian explosion of technologies afterwards the, after that discovery, and so it’s very exciting. And so one of the other factors in this, which is relevant probably for this audience, is how do you think about lunar real estate? How do you think about what happens once we start building structures on the [00:03:00] Moon? What happens to the titles? Who owns these things? How do you do conveyance? How do you do all these other things? These are all exciting unknowns. It’s very blue ocean. There’s a huge market and potential for this, and the activator that allows this future to occur- is using resources on the moon to construct things, right? Because if you can’t build anything on the moon right now, there’s no value to the surface. There’s no value to the volume of land that sits underneath a certain area. But if we are able to develop the land up, then there’s a certain value that’s attached to it for all kinds of different purposes like landing pads, like data centers, like homes, hotels, hospitals, all sorts of other products. So it’s a very exciting place to be building and, yeah, that’s a bit about us. Stephanie Gubiotti: Very cool. Yeah. Yeah. So I know we chatted a little bit about this. Within our network we have something called our hardware and robotics or our petting zoo program, where we really work with a lot of hardware [00:04:00] and robotics companies. And so there’s potentially some opportunities for some mining and robotics companies to get involved as you’re shaping the future of this. Does that sound right? Skyler Chan: Yeah. It’s a exciting opportunity right now because our payload is going to the moon as early as next year, and it’s going to be making the first bricks on the moon. And part of that payload that our team has developed is we’ve engine- we’ve done some really cool engineering with how do you fit a robotic arm inside this payload? How do you use mechanical systems to allow us to create a brick on the moon? And so part of this thought process is one of the things that we’re, that, that’s different about construction on the moon that isn’t the case for construction on Earth is mass, right? And so the funny thing is, when you’re sending stuff to the moon, or space in general, it’s quite expensive. And you pay for your mass per kilogram. And so one of the ways that we’ve been able to bring down costs is find ways to decrease the mass that we send to the moon. And the second [00:05:00] aspect is power, right? So also similar similarly with mass, power is constrained on the lunar surface too, right? And right now, power would be supplied by the lunar lander. And so what we’ve also been able to do is prove that our system is able to operate in low power environments. And so this is a great opportunity, of course, for folks who want to be involved in the construction aspect or the mining aspect or even the robotics aspect to really enable their brand to be one first on the moon. Stephanie Gubiotti: Very cool. That sounds super exciting. So one of the things that’s probably one of my favorite moments of our time together in La Jolla, we spent some time together on the boat chatting a little bit, and we talked about how mental health is important to slow down, take breaks. It was nice to be able to spend some time kind of outside of offices and on the water and I’m just curious for you, a lot of founders are focused on [00:06:00] solving today’s problems, but how do you also balance taking care of yourself? Yeah. And how do you balance long-term vision with the reality of execution today? Skyler Chan: Yeah. Honestly, I don’t really do self-care or any of that mental health stuff. I think for me there’s, be- there’s a time before GRU and there’s a time after GRU, and the time before GRU I was just really unhappy because all I could think about was how we needed to build this set of technology so that humans could one day live on the Moon and Mars. And so what I found interesting enough is obsession has allowed me to be happy because I’m engrossed and obsessed with this concept and this, the entirety of this company. It’s just been something that I’ve wanted to do my whole life. I’m just naturally happy by default. I think there are days, of course, where say, you’re traveling, internationally for different reasons it’s taxing or it’s a crazy day at work. But I think the way to get through it is just to remind yourself that [00:07:00] the mission is the most important thing, right? Everything is working backwards from the mission. And so in other words, if something isn’t going well today, it’s an opportunity to ask yourself is this still moving the needle towards this end state mission that is, ideally in this, in, in everyone’s case, is the most exciting and inspirational mission that you can think of,” right? Life is too short to work on anything else. I mean- Yeah ... you live once, right? And like, why work on something subpar? And so in other words, what I’m getting towards is being unhappy with day-to-day work on a daily basis is likely going to be a sign of- Of not being happy with your mission, like not being on the right mission Yeah and a tangent to this is burnout. Another thing that I also believe is that burnout isn’t a real thing in the sense of classically people qualify burn- cl-like classify burnout as not being, obviously like just being burnt out, right? You overwork, right? You don’t sleep enough, blah, blah, blah. I [00:08:00] think burnout occurs when you don’t have clear intermediate milestones that are inspirational, that are attainable, that are challenging enough to push you far, right? Burnout occurs when you don’t have ... when the goals seem like way too far in the future and, aren’t attainable. And so what I’m getting at is that I think this is actually good that this concept occurs in real life because it forces you to actually think about what are realistic, not realistic, but like attainable goals to work on every single week and every single month, and therefore every single quarter and year, et cetera, so that you don’t work on things that are just totally unrealistic. I think that’s important when it comes to building very ambitious projects like our company. So obviously when we think about schedule, it’s important to plot out working backwards from the end state. What are the series of milestones that unlock the next phase of the business? And when you think about that, it’s important [00:09:00] to also consider okay, how does this play into execution, right? What ... how does this dial down to week by week? And if you can’t communicate it that this is be- able to be accomplished every week and breaking down week by week, then it’s probably not a good goal. And because of that, because we have that like pretty like this forcing function pretty baked in through our process, that group, it forces us and our team at l

  6. Jun 6

    What Matters This Week - 06.06.26

    What Matters This Week - articles, news, and fundings that mattered this week in PropTech. No hype or marketing. WMTW is free, but subscribers also have access to daily updates, premium content, a private Slack community, and exclusive events. If you’d like to join the community, you can here. Struggling with mental health? We can help. We have free therapist hours & semi-weekly virtual coworking for subscribers. Here’s why. Fundings: * Endra, a Swedish CRE/MF MEP mgmt tech, raised a $50M A round led by a16z. * Honeycomb, an Israeli P&C insurance tech, raised $40M led by Zeev. * FuseEnergy, a UK home energy mgmt co, raised a $30M B-extension led by 20VC. * Findigs, a MF tenant screening app, raised a $32M C round led by RPM Ventures. * Drafted, a 3D home plan generator, raised a $16M seed round led by Buckley. * Zazume, a Spanish Resi rental mgmt co, raised a €2.5M A round led by Nordstar. * HLRBO, land lease marketplace for hunters, raised $2.5M led by Mairs & Power. * Propsoch, an Indian AI home marketplace, raised a $2M round led by Athera. * DevD/ZipupPay, a Korean rent payment app, raised a Pre-Series A via SJ. * BrokerBot, AI workforce for RE Brokerages, raised a seed round led by Grand. News: * Legora acquired Cadastral (Legora) Podcasts/ Videos: * Deep Dive 001: Columbus - Why Is Everyone Talking About It? (Build Order) * Can You Buy a House Without Seeing It? (exchange4media) Articles: * Will AI kill CRE? (The Real Deal) * Real Estate Redefined By Technology (Chicago Agent Magazine) * AI Promises Efficiency Gains But Is Not A Replacement For Brokers (GlobeSt) ($) * Could Tech Replace Traditional Property Managers? (Forbes) * Europe’s Largest 3D-Printed Apartment Building in France (PropTech Connect) * Article Summaries: * Will AI kill CRE?, and Could Tech Replace Traditional Property Managers? Long Reads: * To Boldly Go: The Case for Space Datacenters (Semi Analysis) Other Newsletters: * A New Framework for Understanding Cities (Build Order) * BET Pulse: Issue #7 (BET) * Breaking down Entrata’s S-1 (The Appraisal) * Data Centers, Energy, AI — Oh My! (All About CRE) * Fly On The Wall: A Note from Brendan | Anthropic IPO (Fifth Wall) * Grit:Committed to the Outcome; Stubbornness:Committed to the Path (KP Reddy) Events: “The most dangerous poison is the feeling of achievement.”— Ingvar Kamprad Check this out: Source: TikTok PropTech Talent: * Featured Job - Director of Construction, Military Construction (MILCON) @ICON (Austin, TX) * Looking for a role in PropTech or looking to hire someone? Check here. Thanks for reading! If you think we missed something important, send us a note, and we’ll get it in next week’s edition. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit verticaltech.substack.com/subscribe

  7. May 28

    Into the FIRE: Ep #4 with Stephanie Gubiotti

    Series: Into the FIRE. Show Notes Summary: Into the FIRE with Stephanie Gubiotti, Advisor - Foundation for Innovation in Real Estate (FIRE) and the Emerging Manager Program. Special mentions * Company:  FIRE, NMHC, RETTC, TherapyLab, Claude, OpenAI. * Events: FIRE Summit, RETTC. * People: Michael Beckerman. Transcript (Disclaimer: Please be advised that this transcript may contain unintentionally confusing, inaccurate, and/or amusing transcription errors.) [00:00:00] Matt Knight: Hey, guys. Back with another episode of the podcast with Stephanie, and we’re talking a little bit about the summit we just completed in May, as well as some things that are coming up this fall. And if you don’t know, we’ll explain what our summit was, and, shout out to Michael Beckerman, who started it back in the 20-teens. Anyway, enjoy this time with me and Steph Matt Knight: All right, here we go. Had a couple things happen since we last spoke, one of which was in La Jolla. I’m curious your impressions now that we’ve had a week or two to digest it Stephanie Gubiotti: It was the best. I am so proud of how everything came together. [00:01:00] I loved having all of our friends and colleagues in the room with us, and it was a beautiful location. Was really pleased with how all of the timing of events came together. The content was amazing. I unfortunately wasn’t able to go last year. I was in the thick of running a real estate firm, and this year I was able to be there and help you with running it, which was fantastic. Matt Knight: Had, out of curiosity, had you heard about it last year, or was this new as of this year? Stephanie Gubiotti: Yeah, you invited me last year. I- There you go ... I was one of those people who was like, “I’m so busy running this company. I can’t get away. I can’t pull away.” I was, I actually was in New York at the time so I was not able to come last year. But I did hear about it and knew about it. Matt Knight: Good. Good. Yeah, and for anybody listening that doesn’t know I am not an event planner, which Stephanie can attest to, and I do not like event planning, but this is something that Michael Beckerman started pre-COVID that [00:02:00] just was incredible. And it brings together people that don’t get together. And so home builders, and we have VCs, and we have brokers, and we have startups, and we have owners, property management companies. We had two space guys there that are building in space. And it’s just such a unique group of people that I thought we should keep it going. And so we call it FIRE Summit. Michael called it Trailblazers. Whatever it is, it’s this way you get together and off the record talk about hard things with peers. And so maybe it’s worth mentioning who’s in the room and why before we get into our takeaways for another couple minutes. You think so? Stephanie Gubiotti: Yeah, for sure. I think that’s really important framing, ‘cause we’ve gotten... people are like, “Hey, am I can I get an invite?” Or they’re not sure if they’re able to be in the room. So I think framing it would be great for the, for those l- listening. Matt Knight: Yeah. What I took away when Michael did it was there’s so much power in peers, and you see this at Davos and the Sun Valley thing. We’re not the only ones to do this. There was one actually called [00:03:00] Summit out of LA for a while that Garrick Hirshenberg or somebody did. But it’s kinda if you have this burden of running a company and all the decisions are on you, that can be pretty lonely, of which we’re gonna talk about mental health for May and being Mental Health Month. But having people like that in the room that are your peers that have nothing and cannot sell you anything, it’s just, “Here’s the stuff I struggle with. How do you process it with your company?” And so it’s an executive C-suite only group where it’s like we have the burden of leadership and decision-making. How do we make sure we are thinking through this in the wisest way, in the most efficient way? We’re incorporating AI, all that. Does that ring true with who you saw in the room? Stephanie Gubiotti: Yeah, absolutely. And I think because of the quality of who was in the room, everybody’s guard was down. Everybody was super honest and transparent talking about their own shortcomings or challenges that they’re facing. There was a lot of people who, were able to interact [00:04:00] that otherwise may not have other- met each other. It’s if you go to a conference and there’s, a handful of people that you really wanna meet with, these were those handful of people. Instead of having to go through, three miles of walking down a Vegas hall and then hopefully you try to find them, this was a much more intimate event which was able to really lean into a lot of conversation, collaboration. I personally really thought that people... we did a good job, in my own opinion, of balancing content versus experiences and being able to have people connect with one another outside of just the main the main setting. Matt Knight: Sure. Yeah, and maybe one more note before we move on to mental health is y- I... me personally, and I, don’t know if I speak for you, but I would bet you’re similar, is like I have nothing against salespeople. I’m a salesperson myself, junior people, up-and-comer, students, and we have a whole student thing we do. But you can [00:05:00] imagine if somewhere we’re there and we’re like, “Hey Steph, can I talk to you about your insurance needs on your property while we get on the boat?” It would be crass is the word that comes up. Just jarringly different, that we have other programs for that, right? We have happy hours. We have a student program we do. We have a job board. We have lots of programs we do to support that group of people. So it’s not like we’re intentionally not helping those people or excluding them, but this just isn’t the arena for that. Does that ring true to you? Stephanie Gubiotti: Yeah, absolutely. One of the things that, I think of is we have these tiers of our career, and it’s a matter of are they at that tier level in order to be able to provide the value that’s required for that specific room? Because there’s other rooms that we could actually provide them more value that we hold than this specific one. So we wanna make sure that as we’re thinking through the different programs we support people with, what’s the highest and best use of our offerings versus their skill sets, and how do we help [00:06:00] level people up. Matt Knight: Agreed. And it’s probably a good way to... I would tell you mentally being in the room knowing that I’m not the only one wrestling with these things was such a burden off my back to be like, “I know now 50 people I can call and say, ‘Oh, you chose Claude over OpenAI. Interesting. I know we talked about it in La Jolla. Th- can we talk through how it’s going for you?’” That just lightens my lim- mental burden to know that there-- I have peers I can call about that, right? And to be clear, I wouldn’t be invited to the room if I didn’t help plan it, so I’m not sure I’m senior enough. But it feels good to know that you’re part of a group, and maybe that’s how we segue into May being Mental Health Awareness Month Stephanie Gubiotti: Yeah, it definitely does help to be part of a group. We all need we all need support in different ways, and our mental health program is something that really touches my heart very deeply. Mental health [00:07:00] struggles are something near and dear to my heart. I will go ahead and share this. I lost my brother to suicide and it is something that changed me very deeply and continues to impact me nearly five years later. And it’s important for us to, as an industry, provide support and resources as we’re innovating in the space and letting people know that they indeed are not alone. And I can... you and I have chatted about this, Matt, where we’ve had people call us. I’ve personally received phone calls in the last few months of, “Hey, I’m not doing well, and I need some help.” And I’ve been able to be with people in those moments and be able to provide them actionable resources and not just “Here’s a phone number,” which I think is really valuable for our mental health program. Matt Knight: Totally agree, and I think I said this on [00:08:00] LinkedIn recently is I’m, I am ver- I’m almost overwhelmed by how great our partners are in this. And as a reminder, if you’ve never heard this and this is your first intro to it, what we do is we offer free anonymous therapist sessions with four licensed therapists and mental health coaches three of whom specialize in founders and startups, and the fourth, Matt, is a couples counselor for co-founders. And so we say, “Hey, we’ll pay for your first three sessions.” It’s almost completely anonymous. The only thing we know is general statistics like, “Hey, nine out of 10 are females in New York. You might wanna do an event in New York.” We don’t know anybody’s names or company. But our with what Chandler and TherapyLab are doing with therapy and the cutting edge CBT and the things that they do with therapy and mental health is really incredible, and I think with Laura and Sonia being available across different time zones and different countries and having different skill sets, they’re doing a private podcast to avoid burnout. And then obviously Matt wrote the book on, it’s called Co-Founder Clarity, I think, on [00:09:00] relationships between co-founders. That to me, it’s almost intimidating. They’re so much more knowledgeable than we are because, not to the degree you, but with my family having a history of depression and having self-harm tendencies I’ve clashed up against it as well, and this is a personal thing for me, where it’s like I know how hard it is. I know h

  8. May 15

    VC Unfiltered: Ep #2 featuring Dylan Ketcham of Moderne Ventures

    Series: VC Unfiltered Show Notes Summary: VC Unfiltered in Q2 with Dylan Ketcham of Moderne Ventures. Special mentions * Company: Barclays, Moderne Ventures,  DocuSign, ICON3D, Proof (formerly - Notarize), Wealthfront, Trust & Will, Clue, Sigma360, DragonFly Capital, Mesh, Brick & Mortar, Form Labs, Nvidia, Anthropic, OpenAI. * Other: Passport. Transcript (Disclaimer: Please be advised that this transcript may contain unintentionally confusing, inaccurate, and/or amusing transcription errors.) [00:00:00] Matt Knight: Hey, guys. It’s Matt. I’m back with an episode of the podcast Along the Venture Lines. This is my friend Dylan from Modern Ventures, who I think very highly of, and you’ll be able to tell why when you hear from him. But just check out this next few minutes with Dylan Ketcham of Modern Ventures. Matt Knight: All right, Dylan. Good to have you here, man. I appreciate you doing this and helping us talk a little bit about Venture and what Modern does. But if you don’t mind, can we get a quick background on you, like how you got to where you are and what led you into our industry? Dylan Ketcham: Yeah, of course. So first of all, thanks Matt for the invite on, and it’s great to speak to you and all your listeners. My background is a little different than a lot of folks in Venture. I basically started my [00:01:00] career in corporate strategy at a large bank, moved into investment banking for the better part of a decade, and in the latter part of that helped build an emerging FinTech practice at Barclays. So it was based out in Menlo Park. Was really focused on mostly growth stage businesses called Series B and later helping with things around fundraising debt m and a and IPOs and covered FinTech PropTech and Web3. What most people may not understand when you think about someone coming from FinTech into the real estate world is, the largest assets held on bank balance sheets. Around the US today is mortgages, right? And that’s it’s home, home mortgages. It is CRE mortgages, et cetera, first and second lien, all those great things. Not to mention like loan servicing books and some of those other fun esoteric types of assets. But that was what drove us into the quote unquote PropTech space at that point. And I joined modern about five years [00:02:00] ago as a principal or. On the team and do everything from deal sourcing, portfolio company support working closely with our founders with, to try to help them grow their business and think strategically about what the future of the business can look like. Matt Knight: So how long have you been at modern? How many years is that now? Dylan Ketcham: Five years, Matt Knight: dude. Dylan Ketcham: Yeah. It’s flown by man. It’s flown by. When we, when I joined Modern, we had about 90 million under management. We’re now at about 600 million, I think it was the fifth member on the team. We’re, and we’re bumping up against the, sort of 20 ish people here. So it’s been quite a ride. So Matt Knight: I know people get offended when I use the word PropTech. So why don’t you tell us how you define the modern investment thesis? How do you say it to people? Dylan Ketcham: For sure. I wish it was that succinct. I wish it could just be a one word response. But we’re generalists is really the answer. Our LP base, like many others that invest in the built world includes folks across. Real estate, [00:03:00] financial services and insurance. Real estate really is the heritage of our LP base. So our founding partners started a predecessor fund that was an in-house corporate venture group at a large real estate firm. And spun this out about 11 years ago at this point. As a separate business. And so our heritage is very firmly in real estate, but in that prior fund, even though it was within a real estate organization, her big investment was in DocuSign, which most people wouldn’t think of as PropTech. But it was actually the largest reporting vertical for them from a revenue perspective. And so we always think very much about these things that we call outside in, which is how can we bring generalist technology into this industry and into the LPs that we have that operate in these industries that are both the two largest contributors in real estate and financial services to GDP but also, tend to be further behind on the technology adoption curve than let’s say, like a Salesforce or some of the sort of tech first [00:04:00] firms that have been built in more recent years. Matt Knight: I am curious what, what’s evolved? If you started with spinning out of that real estate and doing DocuSign who is not real estate, as biggest revenue s real estate, you and I share an investment at Icon, like what does it look like today? How does portfolio construction in the past versus what does it looking like going forward as a generalist? Dylan Ketcham: So it’s also one of the things that you, that is unique to modern. Many firms that operate in our ecosystem have these strategic LPs. We actually have a devoted team that sits between our LPs and the startups that we work with to act as the connective tissue from the sales organization to the innovators at our LPs. And that’s called our passport program. So the thing to know about modern is. Every fund cycle will take about 50 passport companies in that works out to be somewhere around 15 to 20 per [00:05:00] year. And basically it’s. It’s just us helping companies try to accelerate their sales. And for that, we take a small warrant in a company and help them to try to grow. So that’s every fund we have roughly 50 of those companies. Of those companies, we tend to make core investments in around 20 of those firms. So really thinking about. Our bread and butter here is series A and B. We also have a growth sleeve that we invest out of. And so really thinking about how do we put wood behind the arrow on some of these companies that we’ve worked with, where we really see the opportunity both within real estate and outside of it and really think that we can help them grow in a lot of different directions. And yeah that’s how we think about portfolio construction. Is again, like a broader portfolio of about 50 companies that we’ve helped in passport and have some economics on. And then about, 20 of them that sort of fit our core buy box. Whether that’s from a deal stage, perspective, size, perspective, [00:06:00] revenue growth, all the other things that we are looking for in any discreet investment opportunity. Matt Knight: Anything recently that’s come up that’s surprisingly not real estate, but in your wheelhouse or surprisingly could be real estate, like you said, DocuSign, notarize comes to mind. There’s people like that years ago clearly should be in real estate and I know a lot of companies like Wealthfront are starting to have mortgage products. Yeah. Anything like that comes to mind that recently is either surprisingly inside or outside of, but could become inside? Dylan Ketcham: Yeah, I’ll give you, I’ll give you a hand. Full of examples, both within the portfolio and outside of the portfolio. So within the portfolio you named a couple of them but, think about proof, which was formerly known as notarize. Started as an e notary solution. It’s a broader it’s actually a broader identity solution today. So that’s one Trust and Will is another one that I think many people would be familiar with. So it’s a digital online trust and will service our belief at Modern is every home belongs inside of trust. So we’re [00:07:00] helping to them to deploy through realtors to make sure that happens. There’s another one in the portfolio called clue, which is a personalization agent. That’s and if an LLM ingests data and then needs to, better understand consumer trends to make a more personalized recommendation. That’s where clue sits. And then we also did a deal at the end of the year in the compliance and KYC space called Sigma 360 which, you know, a lot of. LPs operate funds and more and more of the KYC burden is being pushed from fund administrators into funds themselves. And so that’s one that we backed that we think can really help with that. Also one of our, probably best performing companies in, in more recent months is a company called Mesh which we invested in a little over a year ago now. It’s a a crypto payments gateway. So they started by building the plaid of crypto, so connecting 400 plus wallets and exchanges. And then they layered on psps, like Shift Four and PayPal to actually let people pay directly with Crypto. They’re performing incredibly [00:08:00] well operationally from a fundraising perspective. They just closed a big round at the end of the year at a billion dollar valuation that was led by Dragonfly. But they’re also working in the real estate world, helping folks buy condos in South Beach and in New York. And for a lot of folks that are offshore that have. Money in volatile currencies, but would prefer to have it in US dollar denominated assets. They have stable coin wallets and wanna be able to use ‘em. And mesh is helping people to do that in addition to a bunch of other things. So that’s one that I would say is, probably the furthest flung as well and one that people wouldn’t really think about us as investing in a crypto payments business. But we certainly did. And then similarly, looking forward, there’s a lot of stuff that’s going on in, in broader agentic commerce, which is a space that I’m spending a lot of time in and. Really this intersectionality between crypto and blockchain and ai. I think that those two, if we fast forward 10, 20, 30 years will be mutually reinforcing. And it’s a really interesting what’s happening at the intersection of those two technologies. Matt Knight: [00:09:00] In the small World Department. I literally just set up my trust for our house through trust and Will last Friday. Dylan Ketcha

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"Fundings, VCs, News, Podcasts, Data, and (brief) analysis on the technology changing our built world" verticaltech.substack.com

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    Matt Knight
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    2026
  • Episodes
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