Between Two Hedges // building companies with one foot in and one foot outside Silicon Valley [CC067]

In Coffee Chats, SaaS, VC by Leydis ManjarresLeave a Comment

view episode transcript

Trent Hedge 0:00
As you look at Columbus and you look at Root, if you look at Olive, if you look at CoverMyMeds, whoever it might be. Anyone who’s achieved a $250 million valuation or over has appeared to raise outside capital, yet they sort of bolster talent from within Columbus. And they take what I think is very unique to Columbus, while also again, sort of reaching outwards.

Jay Clouse 0:23
The startup investment landscape is changing, and world class companies are being built outside of Silicon Valley. We find them, talk with them and discuss the upside of investing in them. Welcome to Upside.

Hello, hello, hello, and welcome to the Upside podcast, the first podcast finding upside outside of Silicon Valley. I as always am Jay Clouse and I’m joined as always by my co host, Eric, The Browns finally won a playoff game Hornung.

Eric Hornung 1:05
If we did them in. Browns playoff game. I was going nuts last night, man, especially after that first snap. It was. It was great. We’re recording this on Monday. So we won’t know if the Buckeyes are winning tonight. But what I do know is I am a Browns fan and I am a Ohio State fan. significantly less than a Browns fan. But this feels it feels good long time coming Jay.

Jay Clouse 1:33
We should have just pretended as if this was Wednesday when it’s airing. And we could have said, Wow, what a great game that Ohio State won, you know, by three touchdowns 40, 42 to 21. Great game on Monday night.

Eric Hornung 1:47
And just been so wrong.

Jay Clouse 1:49
But what if we were right? What if we manifested it.

Eric Hornung 1:52
Then that would be pretty cool, I guess. Speaking of manifesting and the Buckeyes, we have a couple of Ohio guys on today who manifested their own careers by moving out to the Bay Area. It’s not often, Jay, that we have people from the Bay Area who have companies headquartered in the Bay Area on the show.

Jay Clouse 2:11
Yeah, this doesn’t break our rules, per se, but we’re getting a little lenient, but I think it’s for a good purpose. I think it’s a really good story to tell here. Actually two stories to tell here in conjunction because as you mentioned, Travis and Trent Hedge are brothers. I’ve known Travis for quite a while the Hedge Fund as he’s called on Twitter. They are based in San Francisco. But as you said, Eric, they have a lot of ties here to Ohio and Columbus in particular. Travis is the co founder of Vouch Insurance, an insurance company designed for startups. It was developed by founders for founders redesigning everything about business insurance from scratch. The company offers a platform that works with clients to manage, mitigate and avoid risks. Vouch Insurance was founded in 2016 has offices in San Francisco and Chicago, they’ve raised $94 million to date, Eric.

Eric Hornung 3:02
It’s quite a lot of money. Especially compared to what we’re used to hearing on this podcast. You know, like I know if you were talking about the unicorns of the world, that’s not a crazy amount. And it’s very impressive what Travis is doing, but compared to what we hear on Upside. Where it’s in the 1.5 to $5 million range, 94 million is, quite a lot of money.

Jay Clouse 3:26
Vouch went through Y Combinator in the summer of 2019. Previous to Vouch, Travis was at Silicon Valley Bank and previous to that he was at Nationwide Insurance here in Columbus, Ohio. His brother Trent previously worked at Root insurance. Travis is actually an investor in Root and a company called Olive here in Columbus. Trent worked at Root insurance is now the co founder and head of ops for Atmos and other Y Combinator company in the summer of 2020. They have the entire home building process in one place from design to move in. So a couple interesting industries here, a couple of really impressive brothers to have on the show. And I’m looking forward to hearing their stories as they’ve continued to maintain quite a bit of connectivity to Ohio and Midwest despite being in San Francisco and Trent gets a headquarter for Atmos in North Carolina.

Eric Hornung 4:16
I think one of the themes of Upside is that geography is important, but it’s becoming less important. And in this discussion, I think we’re going to talk a little bit about how bridging geography works in practice and how it worked in their lives.

Jay Clouse 4:32
Speaking of their lives, our friends at Ethos Wealth Management can help you live the one life you have to lead the best way that you can. You can learn more at, and I think it’s safe to say that the Hedge brothers here are living a very interesting life what the one life that they have to lead. We’d love to hear what you think about this episode. As you listen. You can tweet at us @upsideFM or email us Hello@upside.FM. This is the first time Eric and I’ve been back on the mics interviewing A couple of guests in several weeks. So be gentle with us. Let us ease our way back into it. Thanks for your patience. But we’re excited to get back in. And we’ll get to that conversation right after this. Hey, listener, have you ever wanted to get a message in front of the Upside audience but weren’t sure how to sponsor the show or weren’t able to do a long term sponsorship? Well, now you can just go to And let our audience know anything that’s going on in your world, whether it’s an event, an application, a special coupon, or deal, or just letting them know who you are, what your company does, all you have to do is go to And you can place an ad on this show. That’s

Eric Hornung 5:53
So let’s start here. Trent, Travis, how long have you guys known each other?

Travis Hedge 5:57
Well, I’ve known Trent for almost exactly 21 years. I know it turns 21 here next month. So yeah, we go back boys.

Eric Hornung 6:04
And you guys are brothers. That’s what I’m calling out here. Where Where are you guys from? What’s your backstory, you can kind of tell it in tandem or separately, we diverge.

Trent Hedge 6:14
So we’re both originally from outside of Columbus, Ohio, both kind of grew up there and lived their entire lives. And then, at some point, we both ended up in San Francisco. So myself, I had started working in tech in high school, and then ended up going to college in San Francisco, then stay in college for long to be honest with you. But Travis had had also made it out, but I’ll let you talk.

Travis Hedge 6:39
Yeah, so I’ll tell a little bit maybe longer story on that the parents had a small business in Columbus, small Insurance Agency, they did payroll benefits insurance for, you know, your typical kind of small businesses throughout Ohio and the Midwest. And, you know, we were constantly growing up that we only had those, like our opportunities in life, because our parents were able to start a small business you needed to graduate from college, our dad liked to remind us that he grew up with dirt floors are classic kind of, you know, walked uphill both ways and snow kind of story. But he, you know, really pounded that in us. And I think, you know, grew up wearing a sweater vest a career day saying I wanted to be an insurance broker, like my dad and all that. But it up actually really passion about entrepreneurship, innovation, and kind of the intersection of government. And so I ended up working on some political campaigns and starting a bipartisan political platform at the end of high school, beginning of college, to kind of gamify the experience for young people on both sides of the aisles for the kind of the issues and ideas not just like the political parties, I was 19 I had no idea what I’m doing. I think my the idea of building a team is like going around my dorm, asking who wanted to help. And so you can imagine why that didn’t work out, but ended up you know, kind of trying to get a bunch of other experience to become a better entrepreneur someday, over the next few years and ended up at Nationwide Insurance, where I helped out the corporate innovation on there, there’s a maybe a more interesting story to tell behind that in terms of the journey at nationwide and kind of convincing them to get into venture capital for the first time in 10 years, and that end up leading to investing in SMB capital, the first, the first mess we made was into was an LP and one of their funds. And I was fortunate that they had an opening on their team and my boss at Nationwide, you know, was was very supportive and encouraging, and be making that leap. And that gave me the opportunity to kind of keep one foot in Silicon Valley, one foot in Ohio, you know, and led to investing in all of Root Insurance. And I think that connective tissue actually between the Bay Area and Ohio and eventually these other kind of capital markets and technology markets over the world. That connective tissue is actually what’s like, made my career today. And so you know, excited to talk more about that. I do remember though, my first like, my first couple weeks here in San Francisco, I came out use my idea to get into a bar and the bouncer goes, Columbus is that is that a suburb of Toledo and that was what I that was I knew, you know, wasn’t in Kansas anymore.

Jay Clouse 8:54
Oh my gosh, I want to dig into this part of the story a little bit going from college to Nationwide and then being in a position to help encourage them to get into venture capital. It for people who who aren’t familiar nationwide, huge Fortune 500 company, but based here in Columbus, Ohio. So how did you get the opportunity to have that type of influence at a high level so quickly, on your your job at Nationwide?

Travis Hedge 9:20
To be honest with you, I was just bored out of my mind. In my first job there. I was in the rotational program. And the first six months was an internal audit, which gave me a chance to like learn a lot about how the business worked and how, you know, ratings agencies worked well, it was, you know, really good experience, but I was bored out of my mind. And so at the same time, my then girlfriend now wife was doing a like semester in Silicon Valley as part of her college experience at Miami of Ohio. I had friends like Andy Sparks in the Bay Area, and you know, had spent time around folks in college. And so I just started at the same time I saw that Nationwide, had really changed the landscape in Columbus by investing in the arena district and the time they were building out Grandview yard. And they were leveraging their balance sheet to not just, you know, invest in assets, but also develop the community. And there was a, it also made it a better place to attract talent for the company, right. And so that sort of virtuous cycle got me thinking a lot about well, why can’t we apply the same lens towards technology and innovation, venture capital, and I wasn’t the first person to think of that. It’s a pretty well, well, well trodden model. But I put this little deck together and rotational program, as I’m sure other folks can, can relate to, like your job is to go get your next rotation and like kind of pitch pitch the managers in every group, I probably talked to 30 different people across the company. And like 29 of them thought I was crazy. But I found that one guy who he was the head of the private equity group, and was like, Look, I’ve been looking for somebody like you to help me with this for a long time. And I got really fortunate that he gave me way more leeway than then I probably should have gotten. But it was just a really interesting experience. I mean, this, the CIO, was fortunate that he was kind of intellectually curious about this space. And so, you know, we put the pitch together and got approval to go make our first investments. And it just so happened that that first investment was STB Capital, and bo lasky. The partner I mean, these, this is where I just I keep coming back to the connective tissue between these markets, Bo started calling on nationwide as an LP because he was from Michigan, and had launched his venture capital career in Michigan. And so he was familiar with the Midwest and capital markets here. And even though he’s a Michigan guy, Alum, you know, he that I ended up bonding over kind of those shared experiences, even as an Ohio State guy, and I was fortunate that those dots kind of all ended up connecting.

Jay Clouse 11:38
I’ll ask one more question on this point, because we haven’t really talked about corporate venture capital very much on the show. It sounds straightforward. And it sounds kind of obvious. If you’re listening to this, you don’t have a ton of experience into it. But when you’re inside the machine, you’re inside this company that has existed for so long and has so much at stake. What are the considerations that push back on corporate venture capital happening within a large Fortune 500 company that you had to fight against?

Travis Hedge 12:01
First and foremost, I think anytime you’re working with a group like that, you have to understand like what’s in it for the people involved? Right? The CIO and Nationwide is responsible for managing $100 billion balance sheet with an A rating from the credit agencies. And so that stability, I mean, that capital exists not to make interesting investments that exist to be there to pay out claims eventually, and the amount of crisis and so, you know, they have to be a steward of that capital, and every single institution lost their shirt, not every single institution, the elite colleges in the making a lot of money, I think it is temporary, but that’s a different story, lost their shirts in the late 90s, early 2000s. And so there was a ton of scar tissue to overcome from that. I mean, I saw the investment returns, they were not pretty. And at the time, I remember you got it, this is 2000, you know, 12 timeframe, people, the most popular book on the investment floor was this time is different about the you know, boom and bust cycles. And so there was a ton of the first thing I had to do was actually show cyclicality within this asset class. And I think specifically within venture it every you know, is pretty well known that you have to be in the top quartile of investment managers to make any money because it’s the top quartile outperforms every other asset class, the bottom three quartiles underperform every other asset class. And so the conversation was, it was less about, Hey, is this interesting? It was more, why can we get into that top four tile, if everybody else is sitting there camped out on Sand Hill Road begging for allocations, and loyalty decide was if we can bring the full force of nationwide and its assets to bear, then I think we have a chance. And, you know, ultimately, as an insurance company, as large buyer, etc, we help you know, we started kind of making that case. And I remember our first trip out we met with Lightspeed and Redpoint and NEA and ultimate invest in an SMB capital. I think that’s a really interesting, interesting story there. Those Lightspeed funds ended up being spectacular with Snapchat and much others. But anyways, that was kind of the the story, you know, we had to tell him the pitch we had to make, but they weren’t to be very clear, like I was making the decks and making the pitch. They weren’t just listening to me as a as a, you know, 22 year old kid. This is a consistent pattern, I was fortunate to lean on the credibility of those around me. And they we sort of, you know, propelled each other towards that goal.

Eric Hornung 14:20
So Trent, your brother, he’s stripped off the sweater vest, he doesn’t want to be an insurance broker anymore. He’s working in Nationwide going out to San Francisco. How, how aware, were you of what he was doing? And what were you doing in the meantime?

Trent Hedge 14:34
Yeah, good question. I was really lucky to have Travis at that time. So our parents were actually kind of going through their own battles. And Travis had kind of stepped in as this father like figure to me. So I was really interested in what he was doing. I remember I was probably in Early Middle School, the time and I would go down and stay with him in the arena district and I just wanted to kind of learn what what he was up to. I wasn’t super satisfied with what I was doing in school at the time, when I was about 12. I started this landscaping company. And we ended up doing about 60,000 in revenue over a summer. And I kind of taught myself how to build websites. And I was curious and just what I could do when I release something digital to the world, after like putting enough shovels into the ground, I’d kind of realized that I was doing things the wrong way. So I did that for a couple years. And as I continue to talk to Travis, and he was eyeing investments within Columbus, he had just moved out to San Francisco. I thought what Root was doing was really interesting. So I ended up going and talking to Alex at Root. And I found this it’s funny. He mentioned gamification earlier, I found this intersection of teen driving and insurance policies and sort of bundling really interesting. So when you think about it, bundling is sort of the best defensibility as it relates to LTV for any given customer in the insurance industry, whether it be like home and auto or even on the business line. Travis could probably talk more about that. If you look at it, there’s a strong correlation between the riskiest asset classes and auto insurance and teen driving. So the idea was that we could gamify it. And that’s something that I think like my generation Gen Z can kind of get behind. And at the same time, kind of backdoor our way into family insurance policies, which at the time Root was actually kind of struggling with they were dealing primarily with individual drivers.

Travis Hedge 16:13
I mean, this be this was like, three months after it launched or something like that.

Trent Hedge 16:16
Yeah, it was very, yeah. This is very, very sad. So funny enough, we, my school, of course, have no support in it. They thought I was crazy. And I tried to get them in, but ended up doing it anyways. So like, I remember, I pitched a grill and our parking lot at the school. And I started flipping pancakes. And I made the entire school late, which like didn’t go over super well. 2400 Kids late to school and drove the the highest app download day in any given day to date for Root. So that was funny. Anyways, worked for them. For a little bit after that. I ended up going and working for a real estate tech company in Columbus. So I was in my senior year, I was actually playing.

Travis Hedge 16:55
Can we, hey Trent? Can we actually can we tell that story a little bit?

Trent Hedge 16:58
Yeah, go ahead.

Travis Hedge 16:59
So because actually, it’s it’s it is back to this like intersection. I actually think the best thing that ever happened, my career was the Southwest direct flight from Columbus, Oakland. There’s more behind that. But in this case, entrepreneur was out in the valley, raising capital. He and I went to go get drinks one night, I’m telling about Yeah, my younger brother, he’s got the potential, but he just got a little trouble at school. He can go, he can go one or two directions from here. To his credit, my friend was like, Look, man, I’ve been there. Like, let me talk to your brother. And that was it. It was just like a coffee chat. And Trent took it from there. But funny how the world works like that.

Jay Clouse 17:32
Amazing. And so Root Insurance just IP owed, you guys are talking about probably like 2015, 2016 timeframe. Travis, as you’re starting to, you know, take hold of Silicon Valley Bank and move out to San Francisco and in Root Insurance is just being incubated. Columbus probably looked a lot different even then than it does today. Can you help talk about like the the Columbus ecosystem then and set the context for how that might be different to today.

Travis Hedge 18:00
Well Trent. I would, I would actually want to share a quick story on this because I remember at the time, he was going to meetups in Columbus, and he never talk in all the time about the differences. And there was one quote that always stands out to me. Trent, you know what I’m talking about?

Trent Hedge 18:12
Yeah, I would always hear that, that Columbus is going to be the next Silicon Valley for X. So be at FinTech, insurtech, whatever. And I kept hearing this over and over again, it kind of stuck in the back of my head, because on one hand, I really appreciated the whole chip on the shoulder mentality. And I think that that’s something that Ohio does really well. But on the other hand, I was sitting there thinking, why are they kind of shutting themselves out from people who have already done this and done it really well. I found this kind of like a defensive approach of we’re going to do it on our own. As you look at Columbus and you look at Root, if you look at Olive, if you look at CoverMyMeds, whoever it might be. Anyone who’s achieved a $250 million valuation or over has appeared to raise outside capital, yet they sort of bolster talent from within Columbus. And they take what I think is very unique to Columbus, while also again, sort of reaching outwards. And so I when I asked myself, fast forward a couple years, and we can go back to this but fast forward a couple years and I was working as a product manager as at a startup my senior year of high school. I was sitting there contemplating if I wanted to go to school or not in San Francisco, it was ultimately that one phrase that kind of drove me out of Columbus, I thought that eventually Columbus would learn and that you’re not going to replace Silicon Valley but rather, if you can pull in as many people as you can, then that will be great. So I remember the year I went to school, there were people now being recruited from Twitter, for instance, to leave and come to Root and I thought that really that was the right approach. So anyways, I ended up going to San Francisco and now I’m happy to have the one foot in one foot out just like Travis had said earlier.

Travis Hedge 19:50
Yeah, and I think for like that, that phrase just stuck in my head a lot. It’s a mentality and I came across it a ton as well. So when I was at SCB, we took a runner by raising a fund to funds and investment vehicle, specifically for the Midwest, we I mean, we really spend a lot of time on this. But the challenge I kept running into was this almost. I mean, look, I think this chip on the shoulder mentality that Ohio has, it’s Ohio against the world mentality. It treats us very well in sports. It treats us very well and a lot of walks of life. But it can be too insular sometimes. And so a couple things happen. One, I mean, look at Drive Capital, you guys have told that story, you know, a ton of times, but I don’t think it’s coincidence that one of the first things he did was hire Robert, Robert Hatta and invest in their talent network. And you know, pretty much anyone with a semblance of connectivity to the Midwest. Our one mutual connection on LinkedIn is always Robert Hatta. And I think that’s, you know, that was a really smart move on their part. You know, secondly, I mentioned that that direct flight between Columbus and the bay area that was critical to getting investors on the plane, you know, for both Root and Olive, I saw that firsthand. And it’s hard to overemphasize how important that is. And then And then thirdly, so I used to also cover Europe and Israel from a fundraising perspective, we have to raise capital from institutional LPs, and then invest in those regions as well. And I started taking some Ohio investors and friends on these sort of roadshow trips to Europe. Because what I would see there was actually a completely different mentality. I think Denmark did the best job of this of any other mark, and Israel, Israel is the preeminent example of we know what our local strengths are, we know how to leverage them. But we also know we’re competing in a global market. And if we’re going to compete in a global market, we have to we have to tap into the global talent and capital markets. And it’s you know, I think it’s it’s not just how big can Columbus be? It’s How big can we all grow together by leveraging those resources? And I think we’ve all seen that that trend that was already underway, obviously get accelerated over the last last year.

Eric Hornung 21:42
Do you think this concept of communities not just Columbus, but communities that are what some people would call like tier two, tier three, tier four in the startup community development cycle, are going to permanently be dependent on Silicon Valley for capital and talent? Or do you think that this is a point in time and a changing landscape?

Travis Hedge 22:02
It’s a point in time, I think, permanently reliant? No, absolutely not? Um, do I think do I think that Silicon Valley will continue to be sort of at the heart of the global, you know, innovation economy for sure. Yeah. But if you go back 10 years ago, it was the the node in with a maybe a few small offshoots, right. Every other node is getting so much more important now as well. Right. So I think what we’re what we’re actually building is a more robust system overall, right? So that such that the local issues related to the Bay Area aren’t, aren’t as much of a threat to the overall innovation economy. And I think, you know, you build you, you drive more opportunity. You guys have told that story. I don’t know why are we ever going to go back to a world where, you know, you have to be in Silicon Valley.

Trent Hedge 22:45
You know, it’s interesting, as you saw kind of a rise in specialization as it relates to tier two, tier three, tier four markets. So we’ve seen a rise in specialization over the past 10 to 20 years as it relates to economic models, but more generally, you also see, for instance, I mentioned inshore tech and FinTech in Columbus, that was a big thing due to some of the local corporates. But you see the same thing across a lot of these different markets. So I’m in Charlotte, right now, Charlotte, North Carolina. And you see, same thing with big banks, right Bank of America is headquartered here. And that kind of bleeds into the rest of the city. In the past year, though, you’ve seen a general rise in the tides due to people leaving places like San Francisco and New York, which I think is generally bringing in more sort of generalized capital. And I think we’ll see how it goes post vaccine, and when once things kind of restored to normal if they go back to specialization, but I think generally people are seeing these places is now a place where they can live and can establish a home and can grow companies, and they don’t have to be on the coast.

Travis Hedge 23:39
Well, and I don’t think it’s a coincidence that this is happening on the backs of software’s eating the world, right, that we are now you know, technology. If you go back and look across history, right, these sort of waves of innovation happen every 50 to 70 years, technology is becoming the established industry. And we’re you know, we’re reinventing every other every other category right now, that talent does not exist in Silicon Valley. And that was part of, frankly, the opportunity we saw in Root and Olive, you know, you had local, you had a lot of ton a ton of healthcare talent in Ohio, when it came to Olive. And I remember that was the first, the first non barrier investment that I made yesterday capital. And I just felt like, Look, I met dozens of entrepreneurs per week. And, you know, they look the same to me it I felt that the entrepreneurial talent was equivalent. And if you can tap into the local expertise there, that’s a really special mix. And I think the best example of that, that I’ve ever seen was Alex and Dan, at Root where you’re combining Dan from Braintree, you know, he had that experience and I can’t overemphasize enough that that unique experience of having lived that hyper growth curve. There’s only so many people in the world that have that experience. And the more you can pull them into your local community into your company, it’s huge. And so I think there’s a Reed Hastings quote around it’s no longer enough to just be a great, you know, technology company. It’s no longer enough to just be a great x industry company. You’ve got to be both and I think we’re I mean those two things together is where the magic happens. And it’s not a coincidence that markets like Columbus, Indianapolis, Minneapolis, you name it have that talent, the better they are bringing it together, I think the more successful they are

Trent Hedge 25:09
Earlier this year, I guess in 2020, we had Travis and I started angel investing a bit together over 2020, we always want to start a company together can’t do that right now, as we’re both running our own, but I thought we could do something. So we invested in this company called Dwelling. And it’s a great example of this. So the CEO was pretty early on at Uber, Ritual, a bunch of companies like that. And he ended up moving back to Toronto, where he’s originally from. And so you have him who’s kind of been on the coasts a part of these hyper growth companies. And then he recruited his co founder, who was early at Shopify, and actually has never really left Canada, but has really strong roots there and has a lot of them to go recruit. And they’ve, I think half their team now is from Shopify, they’ve been pushing them like crazy, but that’s another story. So now you see them, and they’re kind of they’re spanning across Toronto and Austin, they’re gonna be launching their company here as a first market in Austin. And I think it’s a great balance. So we’ve seen this kind of time and time again. And we’ve since invested in a few more companies, and I think you see a similar mix.

Travis Hedge 26:10
Yeah. And just on that real quick, like, I think it’s really dangerous to like, get distracted as an entrepreneur, but like, Trent and I are passionate about helping founders, like, I mean, there’s a founder, we just back spinning out of Root, starting our own company. And if we’re gonna invest our time, might as well invest a little, you know, a small check alongside that. But I think just, we we benefited a lot from that connectivity. And I know that like the pay it forward thing is really cliche, but I think it’s really important.

Trent Hedge 26:34
Travis has an insurance company with big reinsurance, so you can’t make it sound like he’s distracted.

Jay Clouse 26:41
I want to ask one more kind of looking back question. And I wanna hear from both of your perspectives individually, when you first got to the Bay Area, what was surprising to you, because it didn’t match your expectations, whatever that meant, whatever those expectations were,

Trent Hedge 26:56
When I decided to move to San Francisco, back kind of working in tech in Columbus, I felt like a bit of, I don’t want to say an outsider outlier. But I definitely felt a little strange amongst people my age, I was trying to get everyone to also work in tech. And they all prefer to like party and do whatever else, which I totally respect. But point being I got shot down pretty hard on that. And so when I moved to San Francisco, I thought I was going to find a bunch of people like myself, it turned out it was really easy to find interns that were working at Google and Facebook, but not really young people building interesting companies. And so I ended up having to start this online community in which we had people in London and Africa and Asia, and they were all still sitting like in their parents house in high school 15, 16, 18 tinkering on things, building interesting, early companies. Mind you, a lot of those companies may have since died, a few of them have gone on to raise like institutional seeds and series A’s. But at the time, again, I thought it would be really easy to meet those types of people in the Bay Area, it turned out to not be the case. I think these these sort of younger, exceptional folks don’t just reside in one city anymore, there was right across the world.

Travis Hedge 28:02
Yeah, for me, I had an added somewhat similar experience in that I had friends that were out here and my trips out here, I would, you know, it felt like you just stumbled into like an interesting conversation about a startup or, you know, like these happy hours, parties, whatever, I was fortunate to be able to have a couple opportunities to either work at a friend’s startup here in San Francisco, or work at SMB capital down on Sand Hill Road, I went with SP capital and Sand Hill Road. And I think that was, you know, the right choice for me. But that also introduced me to a entirely different part of this world that I don’t think I was I was expecting, which is, you know, the sort of peninsula South Bay, Sand Hill Road stop. I mean, we were our office was across the street from the Rosewood, like, it was just completely different than I think what I had anticipated. And my job was very explicitly similar to Nationwide, like, where I was born out of my mind early on, like, my job was very explicitly to like crunch numbers and build decks. And I was told, like, your job is not to go as far as companies. So I started going to these like AR VR meetups at night, and like, hosting my own insurtech dinners and these things and like, I kind of ended up having to just create it myself, like driving an hour back and forth each way down the Sandhill road. It was it was different than what I expected. I don’t think people like it a lot of ways they look at like the show Silicon Valley and think it’s all just like, fun startup stuff, but that the average age when entrepreneur hears in their 40s like it’s, it’s it’s not, I don’t think it’s you know, quite the, the young person’s game that everybody thinks it is.

Jay Clouse 29:30
The other thing that I wanted to ask you guys, you know, a lot of people when they make the move to San Francisco, it’s like, I can’t find what I’m looking for in my home city. Like, I’m just gonna go where the action is, and they kind of, they kind of build a new identity for themselves as a San Franciscan, and this is like their life now. And you guys have continued to maintain ties back to Columbus and now Trent with Durham and Charlotte. So I want to hear how you guys thought about your identity and why you continue to to consider and visit and invest in other cities outside of the valley?

Travis Hedge 30:01
Well, it helped that Ohio State won the national championship here in San Francisco But seriously, there was this like a local prize. I was known as the Ohio guy in the office like straight straight from the gate. And you know, when when Shawn Lane came out and pitched Olive and then six months into being at SCB, I was like, you know, that insurance thing is really broken, I should go spend more time, I was really lucky that the first person I called was Alex Tim, and he was just leaving nationwide and starting Root. And like, I think the was I always gonna be passionate about Ohio and kind of Yes, but it also just so happened that like, I got exposed to some really talented entrepreneurs, and I saw it as a as a business opportunity. I mean, you look at the investment returns in the Midwest, I ran the numbers that STD, we’ve seen the numbers now from pitchbook, and others, where there’s great opportunity, there is an arbitrage opportunity. And I think I was fortunate to have a foot in both worlds and see and see for myself that people are under estimating what’s possible, and seeing what drivers doing, etc. I mean, my two most successful investments ever, I think, pretty sure they’re svb capitals to most successful investments ever, if not root for sure is all of it’s up there. Now, both were immediately following rounds that drive led. And we took advantage of an arbitrage opportunity, a company I think would have been much more highly valued had been here in the Bay Area. And so I would love to say it’s like entirely altruistic and born out of passion. There’s a lot of passion there. But like, it was also I just saw an opportunity that I think others were under estimating.

Trent Hedge 31:28
So for me, I ran into a lot of other young people who when building this online community, you had these people across the world, they were all talking about when they were going to move to San Francisco, that was the continuous topic of discussion. People seemed like it was all or nothing, it wasn’t really a Are you going to move to San Francisco? It was a when are you going to move in San Francisco question. I guess I didn’t think of it as like a zero sum game or even binary. In that sense. It was more like supply and demand, where to your point, I didn’t have the resources that I needed in Columbus. And so I needed to go tap that market, in order to meet the people that I need to at that point in my life. I think that at the time, Columbus was kind of too early stage of an ecosystem to to support people who didn’t necessarily want to fit the mold of maybe necessarily working at a local Corporation, not too distressed or anything. So at the time, I when I moved out there, I was like, wow, this is a really polarizing place, like you see people defecating on the streets. And at the same time, you see people going and raising, you know, 100 billion dollar rounds that they wouldn’t be able to raise in the Midwest or elsewhere. And so my thought was, I want to get the most out of San Francisco, I want to get what I need out of San Francisco, which sounds a little transactional. But most importantly, I just wanted to meet the people that I couldn’t meet elsewhere, people like myself, or people like I would consider myself and I didn’t always think that I’d be in San Francisco forever. I think if you tell yourself that you’re going to live in San Francisco forever, there might be something psychologically wrong with you. Because it’s, it’s, it’s tough.

Travis Hedge 32:53
I mean, my wife and I are both from Columbus. And we debated here. She’s got her dream job here. I feel really lucky. But we talk about all the time, you know, when when would we move back to Ohio and, unfortunately, that our company is split between San Francisco and Chicago. So I get to go back to the Midwest quite a bit. Well, until COVID spend a lot of time back home. But I think one of the things about that came to mind here as we were talking was the story of like, how we invested in Root. I initially so like first, Alex needed to get regulatory capital become a carrier. So worked with the bank. And actually I set up this insure tech dinner and brought the chief credit officer or one of the one of the lead credit officers to get them excited about what’s happening insurance. At the end over whiskies were like whiteboarding, hey, here’s what like a debt structure could look like they could get this done, etc. And so you’ll notice like this repeated pattern of I knew I didn’t have the credibility to do myself. But if I brought others to the table that did we could get something interesting done. So we got the regulatory capital, but still, I remember talking to partners on the equity side of the business where I worked. And we’re like, Look, we’re not going to do another Ohio deal. Travis like sorry, but like, we only get so many baskets for fun. I can’t have two Ohio companies. This is ridiculous. I was like okay, all right. All right. So but I knew Ribbit capital is very interested in this space. And they are the the preeminent fin tech investor, right, the Robin Hood, wealthfront Coinbase, you name it. And I’ve been talking to my friend Nick Shea, like there for a while about about the inshore tech space. And so took Nick took Nick golfing and we talked a little bit about this and ended up jumping on a plane to Columbus and going to a blue jackets penguins game. He has a big penguins fan and like, Yeah, really, like pulled out all the stops to try to try to sell Nick on Root. And I didn’t have to I mean, I didn’t need all that extra dressing like Alex and Dan did it all themselves. But you know, we ultimately ended up doing the Series B there not because like i was i was able to convince our team to do another Ohio deal. Like I failed in that. But it was because Ribbit did it and we were able to lean on their credibility as one of the leading investors in the world regardless of the geography. And I think, you know, the only reason that Nick was able to get there was because he could take a direct flight to Columbus for every board meeting. And I remember speaking of change, I remember going to when I first started SCB, one of the partners was going to Columbus for a drive capital LP meeting, like the next week. And she’s like, Oh, I got to connect through Chicago. And she complained about her like pizza. And then the like, there was a tornado siren and the crappy hotel, she had a terrible, terrible experience. And like, I promise you, it’s not that bad. Well, fast forward a few years, and I got to go together with her, we went to Jenny’s ice cream, and she had a great experience. Having that local kind of eyes in the ground really helps. But also, Nick and I would go to the Root board meetings once a quarter. And actually, I think they’ve been a little more frequently than, and we’d stay you know, at, we started staying at the Lobeck. And, and like getting getting drinks there. And I remember there was this one time, we’re sitting there, and I’m listening to the conversation in the in the, in the bar, lounge or whatever. And every single person in that in that room was from the Bay Area, or New York or some other technology market coming to visit Columbus specifically for technology. It was like the whole Facebook group coming to visit Root. It was I mean, it was it blew my mind. And I was like, Okay, this is this is different. And this was like late 2017, early 2018. And it’s only accelerate from there.

Eric Hornung 36:13
That’s amazing. When I think about the Bay Area, I’ve gone out there a few times. And every time I go there, I feel like I’m sitting in a cafe and everyone around me is talking about the things that I’m interested in. And it’s something that you don’t really get in Cincinnati, you have to kind of find your people here. And maybe that’s just a hyper, maybe I got lucky a few times. Right. But it’s interesting that you heard that same kind of conversation in Columbus. I like that, that parallel. I want to pivot to we’ve we’ve talked and alluded to the fact that you guys are both cofounders of separate companies, not the same company yet. But how did you decide where to headquarter? Your company? You understand this kind of opportunity, as you’ve alluded to Travis and Trent, and you still both of your head companies are still headquartered in San Francisco, can you talk me through those decisions?

Travis Hedge 37:01
Yes, I’ll tell you for us, you know, we’re building an insurance carrier for the technology industry. And so we thought it was important to, you know, have a really strong presence. And what, like I mentioned before, will continue to be, I think, the hub of the technology world. And so we started selling Cisco, but very intentionally from day one, my co founder, and I knew that we wanted to be a multilocation company, you know, he had taken his last company public company called funding circle. And they he felt that they actually waited a little too long to open up their Denver office, which ultimately became a big, big presence for them. And so that was one of the first You know, we’ve, we’ve mapped out our core values, we mapped out a lot of things, but that was one of the early conversations of Hey, where do we want to have our second really not even second HQ, like we were going to be fundamentally split from day one. So we ran this big analysis, we looked at insurance, talent, and you know, migration trends and, and which development languages people were writing in these markets. And we narrowed it down to Chicago, Denver, Columbus and Madison, for different reasons. Obviously, I was pounding the table for Columbus. But often what we found there was one, there was a ton of personal lines, insurance talent in Ohio, not as much commercial lines, insurance talent, which is what we’re building five of the top 10 commercial ends carriers are based in Chicago, they had 20, like two direct flights per day versus the one or two back to Columbus. And so I ultimately didn’t end up end up winning that argument internally. Venture guy has been fantastic for us. We found amazing people there. I’ve really, you know, there’s a got a lot of friends and family, though. So that’s been great. And I think that that decision to be to be slipped into cities for day one, you know, frankly, coincidentally helped us build the muscles that it took two to thrive in the current environment.

Trent Hedge 38:39
Yeah so Travis mentioned that moving out to the valley wasn’t quite the like, everyone’s young, and they’re all living in like these hacker houses experiences that he thought they would be. So for me, I actually ended up in one of those experiences.

Travis Hedge 38:52
I say, Trent trade, living the quintessential experience, I was a little jealous.

Trent Hedge 38:56
So I ended up living in this house with my co founders. And we were just starting to build what is now Atmos. And for us, it was actually really great for recruiting purposes on the engineering front. I think now, I mean, it’s super competitive. And in terms of engineers, and we’re now looking elsewhere. But at that time, it was kind of all we knew was was building a company in San Francisco, which sounds very naive at the time. But it was kind of just the default. Now we are transitioning to what we would consider remote first company. So it might say on paper that we’re headquartered in San Francisco, but the majority of our team is outside of San Francisco. So we have folks in LA we have folks in Canada, we have folks in Raleigh, we have folks in Columbus, and we actually have an office in Raleigh, North Carolina. So for us, we think a lot more about kind of this hub and spoke model moving forward. And because we have such a physical presence, for context, we’re building homes, we have to have some sort of probably physical office and each one of our markets, so I don’t necessarily view it as as we’re a San Francisco company.

Travis Hedge 39:57
Yeah. And then to take it one step further for us. It wasn’t about, Hey, where are we based as a company? But where do our customers sit? About 50% of our customers sit in the state of California and other 20% sit in New York, and so like that, that obviously drives a lot of the business. But we also felt that entrepreneurs and other markets were even more underserved or less well served in the insurance world. And so part of our launch strategy was actually to go spend a ton of time and our initial launch markets were Utah, Illinois, Colorado, Oregon, Ohio, Indiana, Minnesota, etc. We weren’t in California until I think it was maybe our 10th 11th 12th state. And I actually think that was one of the best things we ever did. You know, not only was I just, again, passionate about these markets and building that connective tissue, but it was just, I think, a smart business move, because, you know, we weren’t competing against the digital brokers, so much there as we were the legacy offline brokers. And so that gave us a chance, you know, Eric, to your point about like the right coffee shops, the right, what have you, like, I was able to go post up in CO working spaces in Lehi, Utah and go door to door, and, you know, talk to folks about insurance. But that what we also did was intentionally created extra space in our San Francisco office, because I knew entrepreneurs from all those markets would come out to the valley to fundraise. And so when Calvin Cooper from rove came out to to the Bay Area, he would work out of our office, and there were dozens monomers like that. And those are some of our closest, you know, most loyal customers today. And so again, it’s all kind of came back to that connective tissue

Trent Hedge 41:32
To be clear, and no one likes that guy who knocks on their door to talk about insurance.

Travis Hedge 41:38
Not the business to make friends.

Eric Hornung 41:40
So you mentioned customers, you mentioned employees, how much do your investors care where you are? And if you said, We’re leaving San Francisco today, what would be the sticking points or friction? If there is any.

Travis Hedge 41:54
I can say for us? I don’t think I don’t think it would matter all that much. To be honest, especially today. I mean, if we were to have this conversation 1218 months ago, maybe it would have been a big deal. But I think we’re fortunate to have a bunch of investors, our investors have made a lot of investments outside the area, whether it be Y Combinator, ribbit, svb, or the other like, it was not a sticking point for them. I think we got some challenging questions. Hey, how are you gonna address these talent issues? How are you gonna address these managerial issues, but I don’t think it would have been a showstopper by any means. Now it’s every board meetings on zoom out. I don’t think they really they could care less.

Trent Hedge 42:26
I mean, for us, our our investors just care about us having some sort of FaceTime with our customers and they don’t care. We’re where we’re based. Our lead investor and our latest round was Khosla and Evan Moore at Khosla was previously pretty early on an open door and a door bash. But at open door, they had a very similar model where they had first launched and Phoenix and Dallas, but they were headquartered in San Francisco. And so for us, we have a very similar playbook.

Eric Hornung 42:52
Real quick, tactical follow up there. Trent, are your board meetings in San Francisco? Not not this year? Because they’re on zoom but.

Trent Hedge 42:59
Yeah, so funny enough, we still don’t really have an investor base board. So it’s just the founders on the board. And so we’re able to do it from anywhere.

Jay Clouse 43:08
Let’s say you’re talking to an entrepreneur in Des Moines, Iowa, would you recommend that they go and visit San Francisco if they’re working on fundraising? And if so how should they present themselves and the company that they’re trying to build?

Travis Hedge 43:23
Yeah. 100%? No, I mean, look, it depends on I think, the kind of business you’re building, because I think it’s whether you’re investing in venture or real estate, you name it. It’s about matching expectations in capital markets, right? What from a duration perspective, from a risk perspective, you name it. And I do think that things have changed in terms of a lot of the investors who’ve seen the Midwest are taking a Bigger, Longer term view. But I still think there’s a lot more singles and doubles focus investors there than there are home running Grand Slam focus investors. And so if you’re building a single or double business, like you should know who the right investors are, and where they sit for the kind of business you want to build. And I think it’s great that there’s a lot of alternative financing coming around like pipe and, and others that I’m really excited about. But I talked to entrepreneurs all the time about, you know, how do you how about your fundraising strategy, and I think, as much as anything, the feedback the muscle of putting yourself, you know, you’re competing in a hyper competitive market? Well, you should want to have your business challenged by the smartest, most sophisticated investors in the world that have seen as many of these opportunities before, right. I’m not saying they all exclusively sit in Silicon Valley, but it has the highest concentration. And so I tend to subscribe to you know, the, the strategy around putting your list together, you actually want to talk to some of your kind of second second tier investors are not investable, like your secondary group list first, to kind of get those reps in build your pitch, right? build some interest in market before you go after kind of the the top the top of your list, again, depending on how mature your pitches, how mature your businesses, and there’s a whole separate conversation around how to build a great pitch and I think the pitch that works in the Bay Area is different than the pitch that works in Cincinnati. For instance, investors are looking for different things. And so like any pitch, it’s understand your audience, put yourself in their shoes and kind of craft the right narrative. But I absolutely encourage it, because I think it, it helps build that muscle and actually talk to, I talked to Alex Tim about this, like, he’s, you know, he and I are now fortunate to be like helping some new entrepreneurs kind of get off the ground. And he actively encourages them to go through that it was yet you talk to him, it was two or three of the worst months of his life. But adversity is what makes or breaks you. And you either grow through it or you shrink. And if you want to continue growing as a business, I think putting yourself through the wringer there can be a really, really worthwhile experience.

Trent Hedge 45:35
My opinion on this is that it actually comes down to timing as to it’s not really, if you should go talk to people on the coast, it’s more so when which I’m not saying every company has to go raise, you know, coastal capital. But I do think to Travis’s point, you should go ahead and get reps on goal. So to me, and I’m still trying to figure this out, because I’ve seen companies now do one of two ways. One is you are taking pre seed checks or Angel checks locally, you’re not really wasting time, in a critical point your company in which you’re trying to figure out what do we even do when you’re trying to go spend more time with customers than you are investors on Sandhill road? And I think that, frankly, that’s probably a better time spent. But the other the other side of this is I’m an investor, and I’m looking to invest them. I’m kind of unfortunately, you know, there’s a lot of signal based investing. And so you have folks who are looking at, let’s say, an a company that we invest in, had had taken money from from Raleigh, North Carolina. And I know that this was a struggle of theirs when they went to go fundraise. People were like, Who are these investors? We’ve never heard of them. Is this even an interesting company? And so typically, when sort of investors are doing their initial flyby, they might see that and just kind of pass. Luckily, they had gotten into Y Combinator. They were in my class for that. So I think that had kind of helped them cross that curve. But I think for a lot of people, unfortunately, that’s a reality, if you don’t start with with sort of high quality, unfortunately, high signal based investors, it actually hurts you and going to raise your more institutional seed. I think it’s this fine line. And I’m frankly, I’m still trying to figure that one out.

Travis Hedge 47:06
Yeah, unfortunately, I think like, I’ve learned over the years like pragmatically, that you have to value that signal, right? Whether it be with the individuals involved in the business, the investors, the customers, you name it, like, those things do ultimately matter in the marketplace. And then the other thing Jay that to answer your question more specifically around how to position your geography, I don’t think you need to include your geography and your pitch anymore. Now, if it comes up, what I hate to see as folks getting defensive about it, I think more you should lean into it as a selling point, like we are building a FinTech company. And this is why we have amazing access to talent expertise here in this area. And why this is not just you know why I chose to build the business here. It’s why this is the the best place to build this business. And if you don’t believe strongly in that, then then maybe you should revisit where you’re based. But the last thing I would want to do is be defensive about it.

Eric Hornung 47:53
I think taking your guys answers together, it kind of you were talking about the pitch Travis, and it made me think that the strongest pitch is probably like Sequoia is leading our round, doesn’t matter how many times you pitch, you just say that and you’re good to go. Anywhere anywhere in the country.

Travis Hedge 48:08
The data around Sequoia follow on rounds. It’s just you’re very right about that.

Eric Hornung 48:12
I want to take Jays question a step further. So we talked about the transactional idea of going out to the valley to fundraise which you go out there a few times a year, whatever, but you’re not changing anything about your life other than spending a few weeks in the valley. If there was a 15, 16 year old Trent, who’s sitting in one of these cities or a 22 year old Travis, would you we talked about this, this mantra earlier this motto of the next Silicon Valley, how that put a chip on your shoulder, and it kind of insinuated this insular thought pattern. Would you recommend that that younger newer version of Travis living in today’s world, that younger newer version of Trent living in today’s world, go out to the valley for a few years, and then figure it out or stay local for the next few years and invest in their local community?

Trent Hedge 49:02
I think so for people, let’s just call it ages, like 16 to 22. I can think about myself. And yeah, it was awesome being in San Francisco. And there’s kind of this like feeling in the environment. Much like how if you go, I was talking about this with travel Saturday, if you go to New York, it almost feels like money, right? If you go to Boston, it feels like brains. And if you go to San Francisco, it feels I would say like change in a world in a way in which people are thinking about things that I’ve never heard of in Columbus. And so to me, that was awesome. But at this point, most of the people that I found interesting, who were my age, and also doing interesting things, again, were online. And so I think before I even moved to San Francisco, what I would first do is go and find who I would consider my tribe online. And if it happens to be that a lot of those people are moving to San Francisco, that I would love to be there with them, right? If it happens to be that we’re staying in our respective communities and figuring out how to grow ourselves. munities alongside whatever we’re doing that I would love to be able to, to kind of learn alongside them in doing that. So I have this opinion that it’s always great to learn from people who have more experience than you. And I think the Bay Area is great for that. But I think it’s at an early career stage point, more valuable to learn alongside people who are doing similar things. And so I think it just depends on on really what you’re trying to accomplish there. And nonetheless, it takes a good balance. But for me, when when trying to find other people who are doing similar things, I don’t think the first, the first step should be, let’s just hop on a plane and go to San Francisco, I think it should be more thoughtful than that.

Travis Hedge 50:36
At the end of the nail on the head there, and I would echo what I said a few minutes ago about you know why it’s important to go pitch your business and these other markets, it’s about challenging yourself. It’s about growing, I was listening to this podcast on brain health yesterday. And it talked about you know, if you’re, if you’re consistently doing the same thing, and exposing yourself to the same thing, you’re you’re building a lot of deep neural pathways that are really smooth and like you’re gonna get really good at those things. But that is, you know, less than 1% of your overall brain capacity. And if you’re not constantly exploring new ideas, exposing yourself to new things, and new people, you’re not growing. And so I think, you know, whether it’s Silicon Valley or New Yorker, you know, I remember trying to get Trump to go spend a summer in Israel, like, I think exposing yourself to those new things, new ideas that people like, that’s, that’s how you grow. So I would, I would 1,000% encourage anybody to go get out of your comfort zone for a little bit, especially early in the careers.

Trent Hedge 51:30
For the record, if you live in the Midwest, or some other sort of emerging market, per se, or or even less than that, I would definitely recommend getting out, at least at you know, week or a month at a time and just experiencing the world. Part of what people ask me a lot of founders, my age being again, like 16 to 22. They’re all building sort of these moonshot type companies, whether it’s like cube satellites, or AR VR, or whatever it might be. And they’re like, how, how are you building a company in such a boring industry? And now looking back, like I’ve worked in insurance and real estate and homebuilding all boring industries, and yet, you know, you had gone ahead and raise coastal capital, you guys have recruited a really great team. And I think it’s this mix of again, having one foot in one foot out. And so I think if I would have just fully said, Let’s go to San Francisco, I would also be building a moonshot company, which are not great, which is not that a portion of those ended up working out, but maybe just not my style.

Jay Clouse 52:33
All right, Eric, we just spoke with the brothers Hedge. What stuck out to you about this episode.

Eric Hornung 52:39
I think that thing that sticks out just first and foremost is bam, Trent’s idea, that of finding your tribe is something I think that you and I have both talked about, on and off the mics. finding those people that you kind of just jive with is probably the best place to start. And his kind of tactical idea of find them online first, and then figure out where they’re going. I’ve never thought about it like that. But it’s so it’s so simple. It’s such a low risk way of finding your tribe.

Jay Clouse 53:08
Totally, I think it’s it’s incredibly timely, I mean, everything obviously accelerated in this way. But I think that actually trends generation, the younger generation is, is more akin to doing this because they are fully digitally native, you know, you and I kind of grew up one foot in the old world, and then learn how to use AOL Instant Messenger and everything else like that, and kind of got our way into it. But I think that’s becoming way, way, way more just a part of growing up now is finding and building your communities online. I think there’s a lot of risk that goes with that as a young person. But I think that’s incredibly timely. And I think a really good thing, I think, a net positive, I do think it’s actually a lot harder to build safe, comfortable communities digitally than it is in person. Because there’s just walls of anonymity and it’s easier to be a jerk. It sucks, but, but I think it’s I think it’s a good idea.

Eric Hornung 54:02
What do you what do you think about there? I’ll summarize their their answer to that last question, which is should people move to San Francisco? I kind of summarize Trent’s idea there. Travis’s was essentially, Yes, I think so. If you are the younger version of Trent, or Travis, I think you should go do it. What do you think that means? As someone who stayed in Columbus pretty much since since he graduated, and watch the community evolve? What do you think that means for community? Did you have first hand experiences with people leaving and coming back or leaving and never coming back? And did that hurt or help the community?

Jay Clouse 54:35
Yeah, 100%. I mean, I think from like a startup community, or really any community, if you have people that are at the core and a huge part of it, their connective tissue between a bunch of other people, when they leave for whatever the reason it really hurts that community because that’s like, almost like a beating heart of that space that has gone that has to be replaced. I mean, we talked about this before, but I think it happens a lot with community builders in places Across the country, because it’s mostly a thankless job and you realize that you have opportunity, and why don’t I just go look out for me for once, and you go and you go somewhere else. But I think, you know, if I’m thinking about their answers, I think we can simplify it even further to say, be a global citizen, you know, and whether that means physically moving there for a lengthy period of time, or just being well traveled, being well read being well connected to people across the country and learning from them actively. It’s, it’s easier than ever to be a global citizen and use that to impact your life, your business, everything.

Eric Hornung 55:31
Did you ever think about moving out to the Bay Area?

Jay Clouse 55:34
Yeah, I did. I, there was a time right after college, especially when I wasn’t sure what was gonna do. I mean, you and I interviewed for management, consulting jobs, we didn’t get second interviews, we didn’t get the job. And so I was thinking, Okay, well, I guess I’ll do this startup route. Everyone tells me that I should be doing anyway. And I was looking at the bay area for sure. I don’t know, I don’t know if it was a fear of the unknown. I don’t know if I felt comfortable here. I don’t know if it was just the opportunity of textures that fell in my lap. It felt like a leap. And I just didn’t. I didn’t know if I really identified with that. I didn’t even have the language of identity at the time. I don’t know. It just it just felt like going there meant every part of my life was startups. And I don’t think I was ready to make that leap. Did you?

Eric Hornung 56:15
Yeah, I when I lived in Chicago, I applied to hundreds of jobs out on the West Coast trying to get out there. It’s actually where I wanted to go. Following college. It’s like, it was my goal to either live in San Francisco or New York. And I ended up in Chicago, which is the one city that I didn’t want to live in. Nothing against Chicago, just I’m from the Midwest, I wanted something new. And I remember, there was a new app called Robin Hood at the time, and they had eight employees heard of it and heard of it, okay. And I was super excited about it. And not knowing much about finance and investments and brokerage, I asked a bunch of people from the Midwest about this idea of zero fee, brokerage and what it would mean, and everything was negative. Everything in terms of that’ll never work, it’ll just be a money loser. It’ll never make any money going forward. It’ll never have evaluation. So didn’t end up applying to Robin Hood, probably, you know, first 20 employees. So sometimes you win. Sometimes you lose some.

Jay Clouse 57:18
Sometimes you lose some. Well, I think it’s really interesting to hear from both these guys because they their careers in tech are just so closely tied to the timeframe of growth in Columbus, Ohio, where they’re they’re rooted from Root rooted, ha ha,

Eric Hornung 57:34
Ha ha. They have been a while since we had a good pun on here.

Jay Clouse 57:37
Good pun zing. They really had a front row seat and kind of like a, like a time capsule of this is what the community was like then I moved out to San Francisco, here’s what’s going on now. And they were really involved in every step of the process to at least for route and drive capital. There’s a lot of growth there, I actually didn’t realize that Travis was one of the core driving forces between nationwide getting into corporate venture capital. That was a really interesting bonus of the discussion that I actually wasn’t expecting.

Eric Hornung 58:02
It goes back to what we did when we created test city USA was the time capsules are important. The history is important. The trajectory is important and you can’t really know where you are. At any given point of time, you can feel like you’re on an upward trajectory, but you don’t really know where that’s going to go because we underestimate what a city a person a company can do in 10 years. So things can move faster than you think.

Jay Clouse 58:24
If you guys listen to this one to learn more about Travis’s company Vouch you can visit And if you want to learn more about Trent’s company Atmos you can visit I would love to hear what you think about this episode. You can email us Hello@upside.FM or tweet at us @upsideFM. Otherwise, we’ll talk to you next week. That’s all for this week. Thanks for listening. We’d love to hear your thoughts on today’s guest. So shoot us an email at or find us on Twitter @upsideFM. We’ll be back here next week at the same time talking to another founder and our quest to find upside outside of Silicon Valley. If you or someone you know would make a good guest for our show, please email us or find us on Twitter and let us know. And if you love our show, please leave us a review on iTunes. That goes a long way in helping us spread the word and continue to help bring high quality guests to the show. Eric and I decided there are a couple things we wanted to share with you at the end of the podcast. And so here we go. Eric Hornung and Jay Clouse are the founding parties of the Upside podcast. At the time of this recording. We do not own equity or other financial interest in the companies which appear on this show. All opinions expressed by podcast participants are solely their own opinion and do not reflect the opinions of Duffin Phelps LLC and its affiliates under a Collective LLC and its affiliates or any entity which employ us. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. We have not considered your specific financial situation nor provided any investment advice on this show. Thanks for listening and we’ll talk to you next week.

Trent and Travis Hedge are brothers from Columbus, OH, who left for Silicon Valley. But since that time, both have continued to visit and advocate for Ohio and other parts of the country.

Travis Hedge is the co-founder of Vouch Insurance (YC S19). Vouch Insurance is an insurance company designed for startups. It was developed by founders for founders and redesigned everything about business insurance from scratch. The company offers a platform that works with clients to manage, mitigate, and avoid risks. Vouch Insurance was founded in 2016 and has its offices in San Francisco and Chicago.

Trent Hedge is the co-founder of Atmos (YC S20). Atmos offers the entire homebuilding process all in one place—from design to move in. Atmos was founded in 2019 with a presence in SF, Raleigh, Durham, and Charlotte.

Learn more about Vouch:
Follow Travis on Twitter:
Learn more about Atmos:
Follow Trent on Twitter:

Follow upside on Twitter:
Advertise with an upside classified:


This episode of upside is sponsored by Ethos Wealth Management. Managing wealth with an eye toward the future demands vigilance and skill in today’s global economy. Over the years, Ethos Wealth Management has worked with clients and their other professional advisors – including attorneys and accountants – to create comprehensive wealth management plans designed to make the best use of their wealth today and help ensure its endurance for future generations.

They can do the same for you.

Visit to learn more.

Want to share information about your company, or an opportunity with the upside audience?

Book a classified advertisement and your advertisement will be read in an upcoming episode of the show.

Classified ads are priced at $100, and are:
read by Jay and/or Eric on upside
linked from the show notes
linked from this website,