Pod Insights The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch 20VC: The Biggest Trend Of Our Lifetime Is The Decentralisation of Entrepreneurship Away From The Valley, The Biggest Lessons From Learnings The Craft of VC at Sequoia & The Benchmarks Required to Attract Growth Investors with Chris Olsen, Founding Partne About this episode Chris Olsen is the Founding Partner @ Drive Capital, the venture firm that believes the Midwest is the opportunity of our lifetime with more entrepreneurs building billion-dollar companies in the Midwest than in the last 50 years combined. Since inception in 2012, Drive have built an exceptional portfolio including the likes of Duolingo, FarmLogs, LeadPages and Udacity. As for Chris, prior to founding Drive he was a Partner @ Sequoia Capital on the West Coast where he learned the craft from some of the very best in the business. Before that he spent time at both TCV and UBS. In Today's Episode You Will Learn: 1.) How Chris came to found the largest venture fund in the midwest, Drive, from being a Partner @ Sequoia Capital and learning the craft of venture there? 2.) Why does Chris believe that the biggest trend we will live through is the decentralisation away from Silicon Valley? What are the essential ingredients an ecosystem requires in order to foster this thriving tech hub? What does Chris believe it is fundamentally essential for companies to be in close proximity to? 3.) How does the lack of venture funds in the Midwest affect Chris' views on pricing? Would Chris agree with Peter Fenton, "never turn down a company based on valuation, it is a mental trap"? How does Chris look to differentiate between expensive and too expensive? 4.) How does Chris think about reserve allocation with Drive? What framework does Drive adopt to determine where to allocate reserve dollars? How does the shortage of follow-on investors in the midwest impact Chris' approach to follow on financing? What level does a company need to be in order to attract attention from larger growth funds? Items Mentioned In Today's Show: Chris' Fave Book: The Old Man and The Sea Chris' Most Recent Investment: Duolingo As always you can follow Harry, The Twenty Minute VC and Chris on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Cooley is a global law firm built around supporting start-ups and the venture capital firms that fund them. Now we have spoken before about their forming the first venture fund in Silicon Valley, and forming more VC funds than any other law firm in the world but Cooley also represents more than 6,000 high-growth startups across the globe – through the full company life cycle. They are the #1 law firm for VC-backed exits (M&A and IPO) ranked by PitchBook, and since 2014 has represented more companies in their IPOs than any other law firm. Simply head over to Cooley.com or you can check them out at Cooleygo.com.
Transcript Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:00 Harry Stebbings? We are back for another week in the world of the 20 minute VC with me, Harry Stebbings. If you'd like to suggest questions for future guests or suggest guests themselves, you can do so on Instagram at H Stebbings 1996. It'd be great to see you there. But to the show today, and I'm super excited for this one because as you know, we always tend to focus on San Francisco or New York VCs. Well, today we're totally changing that up. With that in mind, I'm thrilled to welcome Chris Olsen, founding partner at Drive Capsule. For those that don't know, Drive is the venture firm that believes the Midwest is the opportunity of our lifetime, with more entrepreneurs building billion dollar companies in the Midwest than in the last 50 years combined. Since inception in 2012, Drive has built an exceptional portfolio, including the likes of Duolingo, Farm Logs, Leadpages and Udacity, just to name a few.
0:45 Harry Stebbings? As for Chris, prior to founding Drive, he was a partner at Sequoia Capital on the West Coast, where he really learnt the craft of VC from some of the very best in the business. And before that, he spent time at both TCV and UBS. And I do also want to say a huge thank you to Lewis Von Arne at Duolingo for the intro to Chris today, without which this episode would not have been possible. But before we dive into the show today, our new sponsor Ring first made a splash when they were on Shark Tank a few years ago. The concept genius. If someone rings your doorbell and you aren't home or don't want to come to the door, you can respond to the person using just your smartphone, adding a level of both security and convenience. Today, over a million people are using the Ring Video Doorbell to help protect their homes. And now Ring has a great new product
1:26 Harry Stebbings? called Ring Floodlight Cam. Just like Ring's amazing doorbell, Floodlight Cam is a motion activated camera and floodlight with HD video and two-way audio that lets you know the moment anyone steps onto your property. And you can see and speak to visitors, even set off a built-in alarm right from your phone. So for me, spending my life in the studio, I have my Ring at home and you can instruct deliveries, check security and just feel much more comfortable all for me from the studio. Simply put, with Ring, you're always at home. And now as a listener, you can save up to $150 off a Ring Security Kit when you go to ring.com/20vc. That's ring.com/20vc. And speaking of providing security and comfort, that's what happens when you work with a firm like Cooley. Cooley is a global law firm.
2:10 Harry Stebbings? around supporting startups and the venture capital firms that fund them. Now, we've spoken before about their forming the first venture fund in Silicon Valley and forming more VC funds than any other law firm in the world. But Cooley also represents more than 6,000 high-grade startups across the globe through the full company lifecycle. They're the number one law firm for VC-backed exits, both M and A and IPO ranked by PitchBook. And since 2014, they've represented more companies in their IPOs than any other law firm. So to learn more about the number one most active law firm representing VCs and VC-backed companies, simply head over to Cooley.com or you can check them out at Cooleygo.com. But that's quite enough from me, so I'm so excited to say for the first time ever, we will be going to the Midwest and I'm delighted to welcome Chris Olsen, founding partner at Drive Capital.
3:01 Speaker 01 You have now arrived at your destination.
3:04 Harry Stebbings? It's such a pleasure to have you on the show today. A huge thanks to Louis at Duolingo for the intro, but thank you so much for joining me today, Chris.
3:11 Speaker 02 My pleasure. Thank you for having me on the show.
3:13 Harry Stebbings? Not at all, but I'd love to start today with a little bit on you and how you made your foray into what I always call the wonderful world of venture capital.
3:20 Speaker 02 So for me, it was really the concert of good luck and hard work. And when I first came out of college, I decided I wanted to be a venture capitalist. But I graduated from college with a degree in political science and had tried my hand in professional squash career that didn't go very far. And so I just decided my backup career could be in venture capital. So I figured the only way to do that was to go out to Sand Hill Road and start cold calling on the VCs and knocking on doors. And eventually a couple of them would meet with me. The unfortunate news about the meetings was that they consistently said, hey, A for effort, but you gotta go and you have to be relevant and learn something and you haven't got any experience. And with nothing but a college degree, they were absolutely right.
4:02 Speaker 02 So I went back and just started to find jobs in business, trying to figure out what business meant. You know, as a poli sci major, I didn't know what that even occurred. I hadn't even taken an accounting class before. So to me, to figure out what a balance sheet was or what a product model was or anything like that meant starting from scratch. And the only place that we're hiring at that time out of college were these programs in New York, these investment bank programs. I was able to worm my way into one of the programs and then kept in touch with a bunch of the VCs and then was fortunate enough that a lot of the later stage VCs valued that cold calling model of the outreach and was able to get into one of those cold calling programs at a venture firm called TCV. And that's really how I started getting into Indian investing.
4:47 Harry Stebbings? Now, I absolutely love that as a story. It resembles mine in many ways. The question I always get, and not in the schedule, so I'm sorry for this, but it's what made you so intrinsically excited about VC from the start, kind of pre-entering the workforce?
5:00 Speaker 02 When I was in high school, I had a disagreement with my father. My father wanted me to be a doctor. I didn't want to be a doctor. And so I decided I had to teach myself about business. And the best way I could do that was starting to read the newspaper. The very first newspaper I got was an edition of the Wall Street Journal. It was in print still at the time. And the very first article I read in that newspaper that day was about this firm in California that was sending back a hundred million dollars to the University of Michigan because they needed to disclose who it was they were investors in. And this was, if you know your VC history, this was the story of Sequoia sending back a hundred million dollars to the state of Michigan because, through the University of Michigan,
5:42 Speaker 02 because they ended up having to disclose things through FOIA requests. And Sequoia had, at the time, made the decision to no longer accept public funds. And because of this disclosure, they wanted to protect the stealthiness of their businesses. And I didn't know anything about VC. I certainly didn't know anything about FOIA, but I knew that if you could send back a hundred million dollars and not miss it, that had to be a good business, even I could figure it out. And that kind of tipped me to this whole world. And then from that tip, I just got my hands on everything. I met with everyone I possibly could to try and understand more about what it was that VC is.
6:19 Harry Stebbings? My word, Chris, we do have similarities in our approaches. You mentioned Sequoia there, a firm that you later ended up working with. I'd love to hear maybe the big lessons for you and takeaways from that experience, working with truly One of the world renowned leading firms. Maybe what were those takeaways for you?
6:34 Speaker 02 Well, I'll never forget my first partner meeting at Sequoia. My very first reaction was, oh my gosh, I've made a huge mistake. I should have gone to business school. I'm completely out on these guys are some of the smartest people I've ever run across. And now there's a whole room of them. And I'm afraid to even talk. But what I learned very quickly was that the partnership at Sequoia is unique. Because almost everybody there is a story of an entrepreneur and many times an immigrant founder. Who came to America to start their company and they are a bizarrely approachable group of people who really value. Young people who are willing to work incredibly hard. And I was the beneficiary of that. Part of it was being the right place in the right time.
7:17 Speaker 02 But the lessons from having the experiences of working with some of the very best companies that Sequoia has been able to work with. Was one of those once in a lifetime experiences that went on for six years for me and. Learned very much about all the fundamentals of what it takes to be a great founder, of what it takes to be a great board member, what it takes to actually. Generate returns for for limited partners. And I don't think there's any place you could learn that. Other than in the workforce itself, that you really, they believe you have to learn by doing. It's it's an apprenticeship model. And so that meant that there's no book that you can read, there's no class you can take. And I was given a lot of arguably maybe too much runway in the beginning to try and figure these things out.
8:01 Speaker 02 And I made a ton of mistakes, but the partnership there was probably the best training ground I could ever imagine.
8:06 Harry Stebbings? No, I absolutely agree in terms of that willingness to help. But I do want to move on and discuss your thesis today with Drive. And the very exciting times ahead and discuss maybe three specific elements. Because first, maybe where you invest, the geography itself. Then dive into how you invest, kind of discussing that investor psychology and then finish on maybe some themes and verticals you're excited by. How does that sound, Chris?
8:27 Speaker 02 Yeah, sure. So to tie back one last story on Sequoia was in that exact same first partner meeting where I was incredibly intimidated. There was also something remarkable that happened in that meeting and that was that there was. A company on the agenda that was based in Petaluma. And the partnership decided not to invest in that company because it was too far away from Silicon Valley. Now, Petaluma is about 10 miles north of San Francisco. It's not like it's a faraway place at all. But the theory of the firm and the investment practice of the firm was rooted in investing in a bicycle ride to the office. Because when you're investing in technology through these companies that were in the 90s, early 2000s, what you were really investing in was groups of people that were highly specialized
9:11 Speaker 02 and really only located in one corner of the world in large quantities to build these next-generation technology companies. Well, fast forward a few years and the advent of cloud computing really led us down a path where suddenly these infrastructure-level engineering, a lot of those tasks were suddenly being commoditized. And the value flipped from being invested in where those few engineers were. It really flipped from being in technology to the enablement of technology as it kind of sneaked into every single business on planet Earth. And you see it today where, you know, the most valuable startup in the world is a taxi hailing application, right? So the remarkable thing about that is that, you know, we believe that you really,
9:53 Speaker 02 to be successful as an entrepreneur, you need to get as close to your customers as possible. Ultimately, your investors aren't going to make you successful. It's the amount of revenue you can convince your customers to give you. And the folks who have a tendency of doing it best are the ones who really spend the time to be in close proximity to their customers and get to know them. So Sequoia's reaction to this phenomenon was to set off around the world and start investing in other geographies, China and India, Israel, their growth fund, their global growth fund. And today, Sequoia and many of the other venture firms, they invest more money outside of California than inside of it. And while we were there, we were looking at faraway places. And at the time, one of my partners at Sequoia, Mark Kwame,
10:36 Speaker 02 was tapped by John Kasich to come out and run a job development program in Ohio called Jobs Ohio. And in the process of doing that, Mark was a storied Silicon Valley person who had really grown up there his whole life. He tells a story that he discovered Ohio. And in the course of discovering Ohio, what he found were all the wrong ingredients to make successful companies here. The more customers here in the Midwest, there's more universities and engineering grads here in the Midwest. Piece that was missing was a venture capital firm that was dedicated to prosecuting that opportunity with the same vigor that the firms in Silicon Valley were prosecuting Silicon Valley. And I was out visiting a company here.
11:19 Speaker 02 We caught up over dinner and he floated the idea by me. He said, why don't you leave Sequoia and why don't you start the largest VC fund in the Midwest? And I immediately was dismissive of it. But I was so kind of intrigued by it because it was such a far out idea that I went down this path to try and prove it with the data. And it was interesting because usually when you meet with a company, you know, the very first meeting, you meet with an entrepreneur, that's usually your highest point. You know, after that, you're left in this very dreamy state. You believe everything and as you get through diligence, you go through this, you return to normal or you get back to reality. And the investment is rarely as attractive in the second and subsequent meetings and diligence as it is in that first meeting. In this instance, this idea had the opposite effect.
12:04 Speaker 02 Every piece of diligence that I found actually validated this idea and said that there was a disconnect in the perception of how the Midwest is today versus what is reality. So you look at the number of engineers who are here. There are more engineers graduating from Midwest universities than any other corner of planet earth. It has the economy that would be the fifth largest economy in the world, bigger than Brazil, bigger than Russia, bigger than India. And it's on top of that has 150 of the Fortune 500 companies here. So we were looking for this customer set that was here, fueled with engineers and felt like ultimately this was the opportunity of a lifetime to do in Ohio in the modern era, what Sequoia and other firms had done in Silicon Valley in the 1970s, that that would
12:49 Speaker 02 be something we're dedicating our lives towards working on and solving those problems. So in 2012, we set up the firm and started down this path to building a firm in the Midwest. That aims to invest in all of these technologies that are today being built by companies in the Midwest.
13:05 Harry Stebbings? Can I ask, you said that about it being kind of the truly radical idea in the beginning. I mean, it really is and still kind of is today almost. I'd love to hear how the LP reaction was when you set about raising for a fund completely out of their traditional ether in the geography that you are.
13:21 Speaker 02 Well, so when we first started, radical is one way to describe it more favorably. I'd say my friends were like, dude, this is stupid. What are you thinking? You know, this is, you're going to the Rust Belt. You're going to this old manufacturing economy that has been the albatross around America's neck for the last two decades. Why in the world would you ever do that? And I think that the LP reaction was similarly mixed. And what was intriguing was, you know, we had a lot of LPs who said, hey, if you guys do this in Silicon Valley, we back you. And our reaction to that is, but I don't understand why. Like, well, it's Silicon Valley. And we're like, but, you know, Silicon Valley is kind of already figured out. Like, we're not going to go out Silicon Valley, Silicon Valley. Like, where's the innovation?
14:05 Speaker 02 What we're talking about is going to a place where there's hardly anybody investing. And if we can go there, then we can really build a competitive advantage that nobody has even in Silicon Valley. You know, the LP is kind of bifurcated. We had, we had some who, they would take the meeting because it was two former Sequoia partners and they didn't want to miss anything and they were nice and they were polite, but they wouldn't invest in the fund. And then we had other folks who would really dig into the diligence and they would really dig into the data and they spent a lot of time with us and looking at our analysis and the research. And those are the LPs who, who ended up committing into Fund One. And the interesting statistic was, I understand the bias. I get it. I live through it every single day.
14:45 Speaker 02 The interesting thing is when you can actually get people on an airplane and they come and they visit, they see it and it's obvious. So 100% of the LPs in Fund One who came to visit us all invested into the fund.
14:57 Harry Stebbings? What did they see that made them convert, do you think?
15:00 Speaker 02 Well, I think what we would do in the beginning is, you know, we didn't have an office. We just had a, we had a suburban and a laptop and that was really it. What we would do is we would drive the LPs around. To what we thought were some of the most interesting startup companies that were here and you know we would take them to go see guys like there's a guy here called Sean Lane and Sean is the founder of a company in Columbus called Crosschecks that he moved here from Baltimore and you know Sean would talk to them about this is a guy who came from the NSA learned all about technology and then started a healthcare technology company artificial intelligence company and said where in the world can I put this that would give me the best advantage and he picked Columbus because it had a great density of
15:41 Speaker 02 healthcare it had a access to an engineering pool that he could afford and then it simultaneously put him in a place where he felt like he could get those early customer wins that early customer adoption so when we would take LPs around and they would meet folks like Sean or or some of the other entrepreneurs what they would see is this is no different than having a lineup of meetings in California so if the founders are here and these raw ingredients are here then this should be a great place to invest and the raw ingredients of talent and engineers and like we would show them these pockets of of really smart people where you've got this giant knowledge based economy that's emerged in the Midwest that people don't necessarily appreciate but when you go and see it and you can see
16:24 Speaker 02 you know companies like Nationwide Insurance they have more engineers than Facebook has and the ability to harness that engineering talent in startups is something that is really powerful.
16:35 Harry Stebbings? Can I ask if you look there and you kind of go back to kind of 101 economics you've got this excess supply of startups and this drought of capital so to speak going into them what does that do in terms of valuations and and how do you think about price sensitivity being in this kind of inherently less competitive market to the 10 term sheets per deal of Silicon Valley?
16:54 Speaker 02 So when we first got here there was another VC who turned to me and said you guys are gonna love it it's great I love investing here you get to invest in B plus companies at half off prices and I was kind of like that's not what I'm gonna invest in and you know my attitude and our attitude here at Drive is I'm gonna pay the market price for A plus companies because the B plus companies they hardly ever get acquired and they certainly never go public it's the A plus companies that the valuations you pay Should look on a relative basis like they were incredibly cheap, no matter where they're based. So, you know, it's interesting, even though there are fewer VCs here, the very best companies are getting priced at a very similar level to those in Silicon Valley.
17:34 Speaker 02 You know, it's harder to get those rounds closed, but when those rounds are closing, you know, they're closing at very attractive valuations for the businesses.
17:41 Harry Stebbings? I'm super nerdy on one element of kind of the picking stage, which is the secondary picking stage, the reserve allocation. How do you think about that? And the thesis around reserves with Drive today, is it a one to one? And is it a stack ranked quarterly and kind of allocating according to kind of achievement? How do you think about that?
17:59 Speaker 02 Well, there is a big difference here from Silicon Valley in that, you know, if you're a founder in Silicon Valley and Sequoia does your A round, you're pretty much guaranteed you're going to get your B round done. There are venture firms that have gone out and built strategies and raised funds that say, "Look, I'm only going to invest in the B rounds of these top five firms." And they put those in their prospectus and the LPs are excited about that. You know, the difference here is that we don't have that yet. Those follow-on investors don't yet exist who are saying, "I'm just going to invest in Drive's companies." So we're aware of that. And so we do end up reserving more heavily for our early-stage investments than you would typically in California.
18:40 Speaker 02 But that doesn't mean that all of our companies get those follow-on reserves just because we've invested in the A. And so we've had to spend a lot of time making sure that we could keep our heads about us and be rational about when companies are working and make sure that we're piling in those reserves versus when we're in a situation where it hasn't quite worked out and we need to use the reserves for other companies.
19:03 Harry Stebbings? I'm intrigued, you said that about kind of using your reserves because there's maybe not the growth capital that there is in the valley. When do you think the handoff is for you? And handoff being a very harsh term, but when is the kind of introduction of external capital into maybe the undefined geography of your geography? When do you think that is?
19:19 Speaker 02 Well, what we see is that there is a construction of capital in the venture world that is bifurcated, where you've got a lot of seed capital, so, you know, in the Midwest and everywhere else too. Specifically in the Midwest, if you want to raise less than three million dollars, there is a very robust pool here of angels and incubators that are willing to invest in those companies. I think that where there's this trough is from, if you're raising between three million dollars and forty million dollars, it's really, really hard. And you've got to get either an exceptional founder who really aligns from central casting for Silicon Valley, or frankly, you've got to work with us. And those are kind of the only two choices.
20:00 Speaker 02 So what we find with our portfolio of companies is if we can get them to a level of about a million dollars in revenue a month, depending on the industry and depending on the type of business, but as a rule of thumb, a million dollars a month, then you've got a business that will be able to raise forty million dollars from the venture community. And if you can do that, then now you're tapping into these growth funds that are on the coast and they're highly, highly mobile. And they're looking to fly in and come in with their teams and they do their diligence and then write a much more sizable check. So that's, I would say, the lowest rung of run rate revenue to be able to get to.
20:35 Harry Stebbings? Before we dive into the quickfire, I do want to stay on this theme and go, what do you kind of depict as the next ten years for decentralization of VC and entrepreneurship, so to speak? How does that look to you?
20:47 Speaker 02 So I think we're in the very beginning. I think we're in the first or second inning here of what is a massive trend across the globe. It's not just in the Midwest. You see this in China and India and other places too. But I think that what we're seeing here is that fundamentally, harnessing technology with domain knowledge lends itself towards very, very strong products and services for end customers. And I'll give you an example. So we're investing a lot right now into the robotics space. Well, if you look at who the customers are of those robotics, they're mostly small-time manufacturers or mid-scale manufacturers. And a lot of those folks are located outside of the coastal areas and in the middle of America.
21:30 Speaker 02 We've seen companies now that are taking advantage of Moore's Law, dropping the hardware costs, putting software on top of it that makes these robotic hardwares super, super Accessible and now you can go in and you can start to automate different pieces of production such that humans can spend their time doing the more complicated tasks. But the stuff that people are doing today with next generation robots, it's basic stuff. I mean, it's just put the piece of metal in the machine, have it stamped, have it come out and then move it to the other side. As you start to look at how much more complicated and how much more sophisticated these robots will get, you will start to see customers applying them to more complicated tasks. But the kinds of things that, you know,
22:13 Speaker 02 where you can get to a world where a robot can simultaneously spit out a smartphone and then spit out a, you know, piece of gym equipment is a long, long way off. The hardware is still specialized. And I think that as that trend starts to continue to grow here, you're going to see this emerge to be a very, very exciting market for the next several decades. And I think the same is true of what I just described to you in manufacturing as well as in other verticals that are, you see in these other places where you've got deep domain expertise in things like healthcare or in insurance or financial services. These are industries that are just at the beginning of getting the technology to, to build better products and services.
22:53 Harry Stebbings? No, I couldn't agree with you more in terms of that excitement for the times ahead, but I would love to dive into a quick fire round. So I say a short statement and you give me your immediate thoughts. About 60 seconds per one. How does that sound?
23:04 Speaker 02 That'd be great.
23:05 Harry Stebbings? So what's the favorite book and why, Chris?
23:08 Speaker 02 My favorite book is The Old Man and the Sea. I, I love that story as a metaphor for all things related to building technology companies where you're out in the ocean, you have no idea what's going to happen. And suddenly you hook on to something that you think is possibly the biggest thing you've ever caught, but the ability to pull it in is going to nearly kill you.
23:28 Harry Stebbings? Now, tell me a story about a time that was transformational to you as an individual.
23:33 Speaker 02 The biggest thing for me was when we were fundraising for Fund One. And in the process of doing that, we had a lot of people that were telling us no in the beginning. And we had been fighting and scraping and scrapping to get to our first close. And we had gotten to a point where, where we thought we were there. So so much so that I called the the movers to come to my apartment. Well, the movers come to my apartment, they are packing up the boxes. And in the midst of all that they're packing, I get a phone call from my partner. And one of our very largest investors in the first close had changed their mind. It was no longer going to be able to come into the fund. So here I was, my whole life on a truck and heading out into something that was now unknown. It was something that was, you have to make a choice.
24:18 Speaker 02 What do you do to do this? And in the process of doing that, I now put myself in a position of saying, well, I got to fling my whole family into into the abyss. But we decided to do it and, you know, we've gone on. And in a funny turn of events, my wife actually was able to, she captured that moment on on video because she got a picture of my daughter sitting in front of the boxes crying at that very moment in time.
24:40 Harry Stebbings? Oh, that is, that is one incredible story, my word. I would love to ask, what do you believe the most around you disbelieve?
24:47 Speaker 02 I believe that the decentralization of Silicon Valley is the biggest trend that we're going to live through in the next 20 years.
24:55 Harry Stebbings? Okay, so what's the biggest misnomer of the valley then?
24:58 Speaker 02 It's a belief that the only place you can find smart people is in Silicon Valley. And it's just not true. And, you know, I think that that's a real bias that we need to get away from. And, you know, it's funny, you travel around to other places, it's perceived very differently. You have a friend of mine who said it best, he was like, I think San Francisco is great. It's a land of opportunity for the 1%. And I was like, whoa, it's a pretty harsh view of it. But I think that the way he describes that encapsulates a really, a really strong misnomer about the place that is popularly held.
25:27 Harry Stebbings? Absolutely, and then let's finish on your most recent publicly announced investment and why you said yes.
25:32 Speaker 02 So the most recent investment that has been publicly announced was Duolingo. And the reason that we said yes was because when we met with Luis for the very first time, it became clear that, number one, this was a world-class founder who was in a world of education that sorely needed technology. And just as we talked about these things earlier around how this is, you know, technology is infecting insurance and education and other things. Language training and language learning was was certainly on that list. And Luis was demonstrating a massive consumer following of people who were able to use his platform to learn English and other languages to provide better economic opportunities for themselves and their family.
26:16 Harry Stebbings? Chris, as you can tell from my voice, I've so enjoyed chatting today. Liz told me it would be an incredible interview, but thank you so much for joining me.
26:23 Speaker 02 My pleasure. Thank you so much for having me on the show.
26:28 Harry Stebbings? What an incredible guest to have on the show. And what can I say? I'm sold on the very exciting times ahead for the opportunities in the Midwest. And if you'd like to see more from Chris, you can follow him on Twitter @ChrisOlsonCMH. That really is a must. Likewise, we'd love to see you behind the scenes here at the 20 Minute VC. You can find more from us on Instagram @HStubbings1996. It'd be great to see you there. But before we leave you today, our new sponsor, Ring, first made a splash when they were on Shark Tank a few years ago. The concept? Genius. If someone rings your doorbell and you aren't home, or don't want to come to the door, you can respond to the person using just your smartphone, adding a level of both security and convenience. Today, over a million people are using the Ring Video Doorbell to help protect their homes. And now Ring has a great new product called Ring Floodlight Cam.
27:11 Harry Stebbings? Just like Ring's amazing doorbell, Floodlight Cam is a motion-activated camera and floodlight with HD video and two-way audio that lets you know the moment anyone steps onto your property. And you can see and speak to visitors, even set off a built-in alarm right from your phone. So for me, spending my life in the studio, I have my Ring at home, and you can instruct deliveries, check security, and just feel much more comfortable, all for me from the studio. Simply put, with Ring, you're always at home. And now, as a listener, you can save up to $150 off a Ring Security Kit when you go to ring.com/20VC. That's ring.com/20VC. And speaking of providing security and comfort, that's what happens when you work with a firm like Cooley. Cooley is a global law firm built around supporting startups and the venture capital firms that fund them.
27:56 Harry Stebbings? Now, we've spoken before about their forming the first venture fund in Silicon Valley, and forming more VC funds than any other law firm in the world. But Cooley also represents more than 6,000 high-growth startups across the globe through the full company lifecycle. They're the number-one law firm for VC-backed exits, both M&A and IPO, ranked by PitchBook. And since 2014, they've represented more companies in their IPOs than any other law firm. So to learn more about the number-one most active law firm representing VCs and VC-backed companies, simply head over to Cooley.com, or you can check them out at CooleyGo.com. I do want to say a huge thank you for all your support. It means so much to me. And I cannot wait to bring you Friday's episode with James Reinhardt, founder and CEO at ThreadUp.
Previous 20VC: Thumbtack's Marco Zappacosta on The 3 Core Elements To All Board Meetings, Raising $250m from Sequoia and Why You Have To Win Supply Side Acquisition First For Marketplace Success Next 20VC: Why Your Board Are Right 50% of The Time, Biggest Lessons From Being Mentored By Reed Hastings & Raising $130m in Funding and The Balance Between Growth and Capital Efficiency with James Reinhart, Founder & CEO @ ThredUp Page updated October 26, 2026 · transcript and summary are machine-generated