Tom Cottingham of Flyover Future // building a news organization covering innovation in 20+ cities across the midwest. [CC075]

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Tom Cottingham 0:00
The thing that makes us really optimistic is our open rates are really high. They’re in their 40s. And our engagement on social media is really high. Which tells us that people want the content, and they like what we’re doing.

Jay Clouse 0:15
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. Welcome to the Upside podcast, the first podcast finding upside outside of Silicon Valley. I’m Jay Clouse, and I’m accompanied by my co host, Mr. New C-Change member himself, Eric Hornung.

Eric Hornung 0:57
Just getting imbedded in the Cincinnati community Jay. I’m meeting people I’m getting out there. We’re post pandemic, and I’m trying to dig into my community.

Jay Clouse 1:07
Tell me a little bit more about C –Change, C the letter not the body of water, by the way, dear listener.

Eric Hornung 1:13
Right. There are no seas in Cincinnati. There are seven hills, but there are not seven seas. Cincinnati Change. Hence C-Change is a group that’s put on by the local Chamber of Commerce. It is rising young professionals in the region. And when I say young professionals, it’s not just your lawyers, bankers, etc. There’s a pretty diverse group of people here, Jay, there’s healthcare workers and artists. And I feel like it’s getting me outside of my finance and tech bubble, which is awesome.

Jay Clouse 1:47
Love that. Yeah. 56 people representing various career and life experiences desiring to develop into civic leaders. What is the curriculum of this look like? What’s the format look like?

Eric Hornung 1:57
So we meet once a month, and there’s a formal formal structure. We have a project, I’m actually working with Finley market here in Cincinnati, which I am stoked about. Because Colleen and I, when we used to live down in OCR, we used to go to flea market every week. Still, actually, I’m heading down there today to drop Hank off. That’s where he gets groomed. Hank is my dog for new listeners. The best part of it is what happens after the meetings and in between the meetings, there’s happy hours and get togethers and there’s a base camp group where we can all connect, and it’s meeting people one on one, it’s meeting people and having conversations, we’ve already had some like really deep conversations that you don’t normally have with strangers, some hard conversations, some societal conversations, cultural conversations, everything. And because it’s like there’s this element of trust in the group, you’re able to talk freely with, I feel a level of comfort, but not so much so that I won’t be challenged.

Jay Clouse 2:54
Sounds like a really positive thing for your future for the future of Cincinnati. It sounds like you’re living this one life that you have to live the best way that you can.

Eric Hornung 3:04
I think I am Jay and dear listener, if you want to live the one life you have the best way you can, you can reach out to our friends at Ethos Wealth Management. If you want to learn more about Ethos, you can go to Now let’s get to the future of this conversation Jay.

Jay Clouse 3:23
Yeah. Speaking of futures, today we are speaking to Tom Cottingham, the founder and CEO of Flyover Future. Flyover Future is a digital newsletter covering innovation and startups in the heartland. They cover the investors, the innovators and the ecosystems that help innovation thrive and help their readers discover the amazing companies and initiatives throughout the Midwest that make flyover country a vibrant center of 21st century innovation. Eric, you met Tom and the team over atFlyover Future before I did and it’s fun to finally have them here on the show because pretty obvious to me that we are kindred spirits care about similar things going about them slightly differently, but could learn a lot from each other.

Eric Hornung 4:03
I was connected with Tom after speaking at Matt Hunklers Unvalued Event, that event is awesome. I highly recommend if you’re a listener of this podcast that you would enjoy that you can go to unvalued powderkeg comm to figure out when the next one’s coming up, Tom reached out and said, Hey, we should talk I heard your panel seems like you’re doing some really interesting stuff seems like it resonates with what we’re doing. Let’s connect so we connected they’re connected again. Now I’ve been meeting with more of the team over at Flyover Future. Love what they’re building.

Jay Clouse 4:37
Previous to Flyover Future. Tom also started insider Louisville in 2012, which I’m excited to talk about here on the show. But I won’t get ahead of myself here. We’d love to hear what you think about this episode. Dear listener, you can tweet at us @psideFM or email us and we’ll get to that interview with Tom right after this.

Eric Hornung 4:58
I hate that we’ve demonized scheduling links Jay.

Jay Clouse 5:01
Scheduling links are actually one of my favorite things. I love the ease of someone saying, here’s where you can book a time with me. And then I can choose when it’s best for me too.

Eric Hornung 5:09
Whenever I get an outreach, and someone says, what time looks good for you. I asked them, hey, do you have a scheduling tool, and you know what scheduling tool I wish they had.

Jay Clouse 5:18
Which one is that?

Eric Hornung 5:18
It’s a new scheduling tool called SavvyCal. SavvyCal makes it easy for both parties to find the best time to meet.

Jay Clouse 5:25
SavvyCal makes the scheduling process even more savvy than any other scheduling tool that I’ve seen and I mean that. It makes it so easy to personalize your link, you can say, Hey, this is a meeting time for Jay and Eric. And it just looks so professional, so sophisticated.

Eric Hornung 5:42
So much so that we’re going to be using it for Upside going forward, and maybe even rolling it out to the Upside network.

Jay Clouse 5:48
You can use SavvyCal as well. You can sign up for a free account at that’s And when you’re ready to upgrade to a paid plan, you can use the promo code Upside for a free month. This episode is sponsored by Fundboard. Fundboard makes free tools and content for founders. Fundboard beta helps you to quickly uncover investors that write checks for startups like yours. Building a Fundboard is really easy. But getting one built for you is even easier. And for a limited time. They’re offering to make a Fundboard for you rebuild with five investors that are a good fit for your startup so you can hit the ground running. This is an incredible offer for listeners of this show. So make sure you take them up on it, you have absolutely nothing to lose in five potential investors to gain just visit That’s The link is in the show notes.

Tom Cottingham 7:00
My first real job was working for one of the very first computer book publishers. There was Osborne and there was Que which was in Indianapolis and I had an English major with a biology minor. I didn’t know anything about tech. I mean, I learned out a program on a PDP 1170. Right. And the PCs have just come out and rode that wave met a guy up there named Doug Cobb, we came down to Louisville started the cob group. Again publishing newsletters and books about technology, ended up publishing dozens of newsletters sold that business to Ziff Davis, which back in the day was a really big computer publisher, mostly magazines, that was really interesting and really fun, sold that business twice. I mean, I didn’t get anything for it. It was privately held, but I was on the team. And the last time was to masayoshi son at SoftBank, then left there and started a company called TechRepublic. And TechRepublic was one of the first online sites that was a community site for IT pros. And we were early and rode the wave and sold out to the gardener group, which was interesting, did another company around technology that was a leads business. And then several years ago was looking at local media. And now I’d never been in the news business per se right? And realize it that the business model was just not working. And we tried to start we did start a digital daily newsletter here in Louisville. And, you know, the good news is we had huge readership, the bad news was there’s just no business model. And we tried every which way. And there were several other people trying to do it too. And just no one could figure it out. But during that time, we spent a lot of of our time looking at economic development, what drives transformation, what attracts talent, and when insider bool will didn’t work. My partner and I who’d been with me through this whole journey I just explained back to the cob group days, we were very frustrated by the fact that middle America was just not telling its story very well. As you guys, you know, well understand, right? And two years ago, when we started this thing, we thought we were entering into an inflection point. We work was kind of part of that for me. And the coast had just priced themselves out of the market. You know, when I started working in tech, the first tech show was the home grown computer fair at Moscone Center in San Francisco. And it was a bunch of geeky dudes with tables, right and literally, and so we watched the the evolution of that ecosystem and a bunch of others, Austin, but, you know, Austin started 30 years ago with Michael Dell, right? I mean, the whole tech movement. Anyway, so we started Flyover Media to focus on telling the story about the amazing things, the amazing things The capital that’s flowing in, and this great opportunity to sort of generational inflection point for flyover country.

Eric Hornung 10:07
How did you get buy in early on on the internet? I feel like there was the still legacy media situation.

Tom Cottingham 10:16
So the TechRepublic business plan. I don’t think I’ve ever said this publicly. So we had a whole print side of it. And we were like, yeah, and we’re gonna do this web stuff on the side. But the intention was never to do the print. But you needed to do that to make people happy. And we really understood print. And we were using, the thing for us was, the internet was very clearly just this ginormous database. And if you’d come out of publishing during the print days, circulation, all that was just database marketing, right? But no, we had a business plan, the first TechRepublic business plan had a hole, we’re going to do all these newsletters in print component to make some of the investors feel a little better about things.

Jay Clouse 10:58
Well, before we dive deeper into the digital side, actually want to spend some time exploring print given that your your history with it here. So you, you are part of a company that sold at least one of these print businesses, what is the evolution of print media been like, that as you see it? And where do we stand now?

Tom Cottingham 11:15
I mean, I don’t really know, right? However, most of the data shows that, you know, we’re getting our content online now. And print for a long time, you know, the tactile thing was important to me, you know, I was a big, I was a huge reader, and I used to travel a ton. So I would bring a stack of stuff, right? And go through it, and you have changing that behavior took a while. I don’t think print media has a solid future at all,

Jay Clouse 11:45
Because of the business model or because of trend changing trends and how people are consuming.

Tom Cottingham 11:50
Both, both. You know, content providers made a huge mistake a decade ago, when they stopped having people pay for content. And now, I mean, the numbers just aren’t there, right, you can have, you know, 10,000 readers, and know that only a very small fraction of those people will ever pay for that content. So it’s just, it’s a bad model.

Eric Hornung 12:16
What’s exciting about the new model, because content’s free. Free is now the anchor price for content. But you launched a media company two years ago.

Tom Cottingham 12:27
Right. Because for us, and I think my feeling is is this is going to become the trend, which is that the internet is going to continue to slice and dice itself in a narrow interest groups, right. And that’s always been our thing. IT professionals back in the day was a narrow interest group. So you know, how do you find high value readers, get them to trust you, and believe your brand and open your emails? Once you do that, then the readers kind of start to tell you what else they need. Me you throw things against the wall and see what how they respond, right. But the the classic media model was always, what else can you provide those subscribers? Can you do events? Can you do data, right? And that’s really the model. It’s so you don’t get the paid subscription part, although you can create paid subscription products, right? data products, primarily. I mean, SaaS is essentially, you know, a subscription product, right. And events is a big part of most media models, right. So as podcasting, you know, as we all try to figure out, you guys are getting pretty good at this. So I must say, you got the whole advertising banter really great. I might. They practiced this before. Did it just come out of I bought a new house. And oh, by the way.

Jay Clouse 13:51
This is very validating. This is very validating. And it’s completely ad libbed.

Tom Cottingham 13:55
It’s well done. Though you guys have a really great interplay back and forth.

Jay Clouse 13:59
I’m glad we kind of touched on insider Louisville already too. Sorry, Louisville, you’re supposed to Louisville level like you’re trying not to say.

Tom Cottingham 14:06
Rocks in your mouth.

Jay Clouse 14:07
Yeah, Louisville.

Tom Cottingham 14:07

Jay Clouse 14:07
Your your description on LinkedIn says tried to find a viable business model for hyperlocal news. But it says you did that for almost nine years. So for a thing to exist for almost nine years, there must have been some business model there. So talk to me about what was working, what wasn’t working. It’s not like you stopped trying to find.

Tom Cottingham 14:27
No, no look.

Jay Clouse 14:27
Business model for a local news.

Tom Cottingham 14:28
I mean man. We really believed and I still believe that it’s a super important thing that we got to fix. And if my LinkedIn profile says nine years of what it was about six, so I may have messed up a date there. But it was a long time. We did not give up right? So we started with myself and another guy basically funding it. The real challenges that if you want to have a robust newsroom, that’s expensive. And so it was kind of getting from a nice little boutique news thing, to are you really going to be the news source of record? And that’s actually a very specific term of art. But, you know, are you going to be the go to news source? And we were, to the extent that we could build a staff that could provide that news, but we just we, we couldn’t do it all. And on on our budget, right, so we generated revenue, several $100,000 a year, but the newsroom itself was a couple million bucks if you wanted to do it, right. And that was kind of minimum viable city newsroom.

Jay Clouse 15:35
And you’re spending everything from like lifestyle, to sports to technology, you’re doing the whole gamut? I’m guessing.

Tom Cottingham 15:40
No, we were really focused on business. And we did lifestyle. And here’s the other thing, right. You’re gonna have two or three or four serious business stories. One of them’s a big deal. We’re gonna have a restaurant review. restaurant reviews get by far the most clicks. The biggest story we ever did was a store and and remains to this day was a story we did on how to get Pappy Van Winkle.

Jay Clouse 16:04
Oh, my gosh, I believe that.

Tom Cottingham 16:06
Right? It went viral. It’s crazy. And then so then we we went nonprofit. And really the challenge there is in these midsize cities, if you make the wrong people upset, you are dead to them. And their entire their entire network. And so it’s hard to have a newsroom when you’re not getting people upset. If you’re the monopoly paper, right, if you have one of the limited licenses to broadcast, people don’t really have anywhere to go. Right? If you’re the new kid on the block, and you upset people, you just get cut off. And it’s not because you’ve written the stuff that was wrong. Right? It was because they didn’t like the characterization, or they wish you had done the story. Except, you know, the first thing you always say is, did we get anything wrong? Tell me now. I’ll fix it. So that made it really, really tough. And then of course, you know, Google and Facebook and all that and their business model. And they’re really good at what they do. I mean, you know, evil geniuses, right?

Eric Hornung 17:07
Take me into something you mentioned earlier, which is this idea of curating high value readers in the niches, I think about kind of what we’re doing here at Upside and how our audience is broad. There’s, there’s no one specific like job title that everyone has. But then the niche kind of IT professional that you mentioned earlier. How are you thinking about with Flyover Future with insider Louisville, whatever it is? How are you thinking about curating your reader base?

Tom Cottingham 17:40
Well, we actually have a database of all of the, I mean, I hate using this jargon, but the stakeholders and the innovation economies in each of these cities, right? So that is curated by us, and updated every quarter. So that’s, that’s a good place to start, right? The great thing about online is, you know what people are reading. And so you can kind of look at content, and say, this segment of people is reading this kind of content, this segment of people’s reading that kind of content. And so what else can we provide them? Right? We’re really interested in talent right now and kicking around a lot of ideas around talent, and how we help our audience. I mean, we have we have kind of this global tech stack competition right now, right? You’ve got China tech stack, and you’ve got the western tech stack, right. And they’re very separate. And they, they obviously have different capabilities. Everybody’s got a personal stack as well. And we look at I mean, the education business model is not working on a lot of levels. They used to be you graduated with a four year degree, maybe you got a master’s degree. And that was it. And, you know, you took a Dale Carnegie course or something, some point or went to a sales seminar. And those days are over, right? First, you really need a four year degree, do you need to get that four year degree as a resident at a at a university somewhere? and pay? You know, because the ROI on that just doesn’t work for most people, right. And the really sad thing is that a lot of people drop out in their sophomore year. So what do you got? You got two years of college debt and no degree. That’s a tragedy, really. So anyway, we think that people are going to be adding modules of capability to their personal tech stack. And that each city has a dominant tech stack or two, that if you want to work in that city, you better understand those ecosystems and you better be able to use that tech stack, right? So that’s part of how we’re mapping so we’re going to map the region that way. And then events, I think is going to be a big thing for us. The radar will turn in what this database, we call it the radar, because we’re Flyover and we’re very clever. I see.

Jay Clouse 20:10
I like it. I like it.

Tom Cottingham 20:11
People in the Midwest, we’re not all stupid. Anyway. So, you know, we hope to continue to add value to the radar. And that becomes a paid subscription product at some point. But yeah, it’s media has changed dramatically. And you know, you’ve got to be looking for the other sources of revenue. If your basic advertising business can kind of cover your costs than the rest of it is what adds the juice. But it’s tricky. And people, I’ll tell you what, the thing that makes us really optimistic is our open rates are really high. They’re in the 40s. And our engagement on social media is really high. Which tells us that people want the content. And they like, what we’re doing. As you guys know, it’s harder with podcasts to track that stuff. And which is why it’s a kind of a long haul kind of deal, right? But we have a pretty good sense of what our readers are interested in what they’re doing what they’re reading.

Jay Clouse 21:07
So when you moved from Insider Louisville to Flyover Future, what was the 80-20 of what you kept from what you learned in that experience moving over to Flyover, like, What do you say, well, we’re gonna cut all this out. But these are the things we really need to focus on in this new.

Tom Cottingham 21:22
Well, cost got to be low. So you can’t have a $2 million newsroom. Maybe someday, but not right away. Honestly, that was I mean, besides all the things we learned about what we think drives economic development, and things like that, I think the big thing was keep the costs low. I’ve always been a big believer in once you find talented people don’t let go of them. So we brought on people that we knew, and that new startups, and that we knew could think on their feet and not completely freak out when nothing happened the way you thought it was going. Hey, sometimes it’s better, right? But it’s rarely the same. So you know, you’ve got to keep costs low. You can’t compete with Google. And you’ve got to come up with really compelling content, because people got so many options, right? So the big thing is, make sure they’re open in the mail. Make sure they’re engaging in the content on social media.

Eric Hornung 22:21
How do you think about the network of brands that you have now? Specifically, are the game of Cinci, Indie and Louisville future under the greater Flyover brand? What was the strategy behind going city based as opposed to topic based.

Tom Cottingham 22:38
When we started, you know, this, this lack of a media strategy was acute in the cities as well, right? In fire, where we have a few challenges that are that are very distinct. One of them is our storytelling. And the reason why storytelling is so important is people do not believe what’s two reasons. First, people don’t believe are your data. I mean, so you just can’t go out and say, Well, we’ve got you know, this is our workforce. And here’s the data. And here’s how awesome we are, right? everybody’s like, whatever, what they want to hear what people believe are other people’s stories, don’t tell me how great you are. Have someone else tell me how great you are, right? Have a customer or an employee. So the cities need to tell their story. In the last couple years, many cities have gotten a lot better at it than the city’s got to talk to the region because talent and capital are much more fungible within the region than they are from outside of the region into the region. Right. That’s where there’s a big breakdown. And then the region’s got to talk to the rest of the world. Because the you know, for a while we had played around with a tagline The world is watching. And it just sounded too creepy, but right, just does. But the sentiment behind it is true. Everybody is kind of looking at middle America right now, as places to invest as places to move as places to start businesses. And this is, you know, like I said, this is a generational opportunity. But we do a terrible job of explaining to people why this is so great. And it’s not just because it’s cheaper. For every middle sized city in America goes out and says we’re cheaper than whatever. So the story has to be a very specific story. Top talents, once people feel they’re they’re paid fairly. The most important thing to the top talent that people were you know who live right now in a seller’s market is to work with other top talent, number one. Number two, believe in a mission. Number three, trust senior management, and is a term as far as cities go, they want a city where you can get engaged and make an impact quickly. All these cities have all those things. And we just got to tell those stories. We got to say yes, there are world class people in Cincinnati, Ohio, in Cleveland, Ohio, in Louisville, Kentucky. And now, then you say, but it’s we don’t have the breadth that Silicon Valley has, right. So those world class people exists in a couple of pretty well developed ecosystems. So if you’re going to design the next jet engine, probably don’t do that in Cincinnati, go to Wichita, because there’s no ecosystem. And the other thing top talent wants to know is, what’s my next job? And usually people are bringing along someone else, what’s their job, and technical people tend to pair up with other technical people. So explaining that is super important in attracting and retaining people. We have amazing research universities, I mean, the big 10 and Carnegie Mellon, we export that talent every year. You know, I really?

Jay Clouse 25:53
You mentioned earlier, you know, when you’re doing news in a small city, it’s really difficult to make a go of it, if you pissed the wrong people off. And I think about even the middle America opportunity, right now, there’s probably a few incumbent players in that narrative. And if you piss those wrong people off, you might have a similar issue. Do you think about that at all? We thought about that at Upside.

Tom Cottingham 26:16
Well, like I said, right, people get upset, because they don’t like the color of the story A lot of times, right, we don’t like how you shaded it, we wish you would have said this, or that that’s always gonna happen. And it’s kind of like, get over it, you know? Sorry. I mean, it’s funny how people will complete you’ll write what you think is a glowing profile somebody. And they’ll come back and say, you know, we you said that I was a party guy in college? Well, you were, I know, but I don’t know, why did I, you know, why do you have to bring that up, you know, kind of stuff. But in general, our job is not to point out mistakes. Our job is to say, what’s working, let’s do more of what’s working. Now, the radar is gonna allow us to compare cities, and we’ll do that, you know, as objective as we can. And some cities are going to look better than others in some areas, right. And some will look better, you know, and I imagine that’s going to generate some heat, but a little heats. Okay. Little heats good, actually. But it’s way different than, you know, looking at what the school board is doing, which is hugely, hugely, hugely controversial.

Jay Clouse 27:22
Yes. To say, how do you think about, you know, in a previous life, you were doing very journalistic things, where there’s no, there’s no spin or bias or flavor on this type of stuff. But when you’re talking about storytelling for middle America, because you think that this isn’t being done in a certain way, and even you know, Eric, and I talk about this a lot. It’s like, we’re partially doing entertainment here.

Tom Cottingham 27:44

Jay Clouse 27:45
So how do you think about that line for flyover media?

Tom Cottingham 27:49
It’s funny, we do a quiz at the end of most of our issues, or know your city kind of thing, right? super popular. That’s how right I mean, you throw in a little entertainment and and you try to write about stuff that that has, you know, kind of an interesting curiosity factor to it that people think is cool. And whiz bang, I mean, mostly what you want people to do is go like, I didn’t know they did that Louisville. I didn’t know that, that rockets, you know, that that amazing woman was teaching at University of Cincinnati, right? That’s kind of what we do. And we hope that every day we give you you know, a little happy surprise, because as you guys know, there’s no shortage of really cool stuff going on. But yeah, I entertainments important, we do a little entertainment, that’s informative, and people really like it. But context is super important. It was interesting bills. If, who was the guy that owns Ziff, Davis, when they bought us had invented was father really had, he had blown it out the special interest magazines, so yachting, sailing, skiing, car and driver, all that stuff, right? And the car companies and the liquor companies, advertised a lot and those things, because contextually it made sense, right? The demographic for the computer magazines was exactly the same, heavily male, high income, college educated, blah, blah. And the liquor companies and the car companies want to advertise in, you know, PC Magazine. And he was like, No, contextually, that makes no sense. Right? So context is important. We want to entertain you. But that is not the main thing we’re doing. We’re trying to give you information that you’ll find engaging and interesting and useful, and that we’re doing it with as little friction as possible, and alive for too long the way.

Eric Hornung 29:39
You mentioned earlier, this generational opportunity, referring, I think, more broadly to the middle of the country. But I’m curious about how you think about the generational opportunity as it relates to media like what’s what’s Flyover’s vision?

Tom Cottingham 29:53
Well, the vision is people are going to still and increasingly get more and more common Content digitally, that telling stories distributing content on multiple platforms is important. I’m actually pretty bullish on podcasting, and think that’s going to happen. And I think back to this sort of narrow casting idea, right? So it’s people have to trust you, whatever you’re saying you’re going to deliver, you got to back that up. That’s really almost the most important thing. Right? And then I think this whole storytelling is important because people become so skeptical, right? I mean, they want to know, they want to hear from, like I said, are your customers, your employees, the people that live in your city, they don’t want to hear from the CEOs and the mayors.

Jay Clouse 30:43
When you are going into new cities, Eric mentioned that you have Indi, Louisville, Cincinnati right now, how do you know when you can support a new city? All these cities across the country have stories to be told. For sure.

Tom Cottingham 30:56
For sure.

Jay Clouse 30:56
We both. We both know that. So how do you know that a city works for your model.

Tom Cottingham 31:01
The way we’re doing it now is we’re launching radars in each city first. So in Indi, we don’t have a newsletter yet. But we do have radar up. As that starts to get tricky. And you have to sign up to get access to the radar, it’s free. But we’d like you to register. So that to us is our indication of are we going to be able to launch in that city, right? We get you know, 1000 or more people that are starting to engage with the radar, then we start thinking seriously about launching a newsletter in that city.

Jay Clouse 31:33
And you know, you said you don’t want to have that $2 million newsroom. So in a mature or at least as far as the spectrum goes for Flyover right now and a mature deployment of your team into a city, what does that look like? Do you have a whole person on the ground that’s pushing the newsletter?

Tom Cottingham 31:51
It’s it’s different. In each city, we have freelancers who are on the ground that live in that city. That’s important. And we develop relationships with those institutions and organizations that are female, important players in this whole innovation economy world. So central fuse, Cincy tech, university Cincinnati, right. And since the end, we get to know those people, we interview them. The interesting thing for us is, the people that we write about are also the people that read us, who are also potential advertisers, who are also potential people to attend our conferences. So you know, we go into a city with a relationship building already in place, freelancers on the ground, a radar that’s up and running.

Eric Hornung 32:41
How do you think about who’s important in a city? You mentioned the big names, there’s obviously the centralized people, but how do you define importance?

Tom Cottingham 32:48
We go into the city we ask people, right? I mean, you just ask because right? The the big ones are obvious. Then you start saying, Who else should we write about who’s busting a move? You know, what organizations in your city are really having an impact? And that’s how you find, you know, the people that don’t make the top of the list when you’re normally thinking about, you know, who those players are? Universities are huge, right? And I think universities are just starting to kind of figure out how to move to the next level of tech transfer and getting their IP out into the market, right. But you think about pick one, right? I mean, we’re talking to the people at University of Michigan, who are gradually, you know, exactly the people everyone’s trying to hire and these kids. So here’s what’s interesting. They want to stay in the Midwest. And like this pandemic is accelerated all this, right. I mean, there literally was a rule. Literally maybe a little strong, but it wasn’t just made up that Silicon Valley VCs, were not going to invest in any company, where they had to drive more than 20 minutes to a board meeting. And there’s stories, I’m sure you guys have heard from entrepreneurs all over the place, who said, investors said they would invest if we moved to Silicon Valley, right? So the past year, these guys have been having zoom meetings with people that are, you know, two blocks down the street. And it’s working for him. They’re having board meetings on zoom. So those old networks just got blown up. You went to Silicon Valley, because procs physical proximity mattered, right? Because that’s how the network was built. And those relationships were your shortcut, right into getting stuff done, and meeting people, and you could, but you don’t have to do that anymore. And oh, by the way, it’s really hard to hire technical people in San Francisco and in Boston, and in Austin. It’s a seller’s market. And you look at, you know, look at the Salesforce tower. It’s not going to be occupied. San Francisco is going to have to reinvent themselves. There, they’re no longer working sitting me when I was young. San Francisco was a hardcore working city, right. It was a port city and Oakland was and there was manufacturing going on and all kinds of stuff, right? But no one’s going to very few people are going to drive an hour and a half into work and park and eat lunch downtown and get back in their car and drive an hour and a half back when they can save three hours and resume. And even though zoom isn’t optimal, that three hour delta is pretty important. And the cost. So I mean, the other generational opportunities, I really think that millennials are rethinking life priorities, being at home for the past year, and having kids and not having to go into work and driving to work and all that is been really transformational. When you guys see that?

Jay Clouse 35:40
Oh, for sure. I’m sure we’re in that right now. Eric and I just recently got engaged.

Eric Hornung 35:45
Very literally right now.

Jay Clouse 35:46
We just bought houses like we’re things are things are definitely changing. And you know, I follow some folks on Twitter. And it’s funny now that I’m seeing these people who we’ve really looked up to, because they built really lean online businesses that can work from anywhere are talking about how excited they are to now buy a home and a piece of land and do home improvement projects. Like it’s, it’s really interesting.

Tom Cottingham 36:09
We’re all, everybody’s nesting now. They’re cooking more, right? I mean, it’s just interesting. And I think there’s a lot of a lot of good things that are coming out of that.

Jay Clouse 36:18
Tom, if you were to look into a crystal ball, or not even a crystal ball, cuz we’re not necessarily making a prediction. But what does what does the success story of Flyover Media look like? And on what timeline.

Tom Cottingham 36:28
The success story is that we are one of the major connecting hubs for the innovators in our region, right. So part of what we think is important is for people in the region to start building networks between cities. So we hope to have city specific newsletters in a dozen cities, we hope our radar is up and running and valuable enough that we can charge for it. And then we have a really interesting and active events business. And that, you know, there are lots of different kinds of events. And we’ll play around with a couple of those different types. But when people think about innovation in the Midwest, where we want to be one of the names they think about and will start to promote pretty aggressively to the coasts because the coasts are looking at us. And they are internationally just farmland alone, right? I mean, you know, Bill Gates is buying up farmland Iike crazy. That’s not accidental.

Jay Clouse 37:24
Well this has been a great time. If people want to learn more about Flyover Media? Where would you send them?

Tom Cottingham 37:29
I would send them to, and they can see all of our newsletters. They can see the radar sign up. It’s free, and I think you’ll enjoy it.

Jay Clouse 37:39
Eric, do you know what I love to have for breakfast?

Eric Hornung 37:43
A big ol bowl of Jay-O’s. I just imagine you have a box of cereal with your face on it.

Jay Clouse 37:48
I was going to say reviews on Apple podcast. They give me more sustenance than anything else in my life. They bring me energy. They get me ready for the day ahead. And you know, Eric, it’s been it’s been a minute since I had a good bowl of reviews on Apple podcasts.

Eric Hornung 38:03
Sometimes I read my reviews right before I go to bed just so I can dream good dreams at night.

Jay Clouse 38:08
If you want to help me start the day right and help my self esteem while also helping us in the eyes of apple. Please leave a review for upside on Apple podcast. If you have an iPhone, even if you don’t use Apple podcast, we would love for you to submit a review about why you love Upside. And if you don’t have an iPhone, if you’re an Android user, that’s okay too.

Alright, Eric, we just spoke with Tom Cottingham of Flyover Future. What stuck out to you about this interview.

Eric Hornung 38:39
Sometimes, Jay, I’m just like really impressed with how you answer questions. You didn’t know this was gonna be about you did you?

Jay Clouse 38:45

Eric Hornung 38:46
And when we premiered the film Test City, USA, we did a audience Q&A after and someone asked you what do you want to see more of in Columbus. And if simplication as the ultimate form of sophistication, you simply said more, more everything, more investors, more community more whatever. When I think about what Flyover is doing, I think about what Powder Keg is doing. When I think about what Upside’s doing. When I think about all of the kind of startup media storytelling that’s happening around the middle of the country. I think that that same answer makes a lot of sense. I want to see more of it. I want to have more founder stories told. So I’m stoked about what they’re doing. I liked it. They’re going about it through the newsletter medium. I think it’s a boon to the business culture of the middle of the country.

Jay Clouse 39:38
What a kind start to this outro. Eric, thank you. I agree with with what you’re saying here. What stuck out to me was Tom’s podcast voice just absolutely phenomenal. Wow, I should be doing way more on the mic. But also, you know, his history in print journalism in print media adds a lot of context to what we’ve now learned and understand about the opportunity for localized media. You know, he, he ran Insider Louisville, and they had a very large editorial team with a huge p&l sounded like basically, I’ve never thought to that level of scale with what we’re doing at once I never, but I haven’t thought about like hiring full time writers in that way. And so it’s interesting to kind of see more about where people have pushed the boundaries, what they’ve learned from pushing that boundary, and now where they’re coming back to. And obviously, he and the team are trying to do things at a much more lean capacity now. But I agree that the opportunity in written journalism for localized media is very prominent, like you and I talk all the time, mostly you talk all the time, this is your, your vision, that there’s there’s a huge opportunity for localized startup and early stage business journalism. And we’re starting to dip our toes in that water with one pigs fly and lay the land and the Cleveland tech newsletter. But Flyover Future guys like Tom, they’re doing a similar thing in different regions. And there’s probably good ways to collaborate.

Eric Hornung 41:07
It’s funny that you bring up the word journalism, because I think we throw media and journalism into this bucket of they are the same thing. But I actually have a strong view that there’s different types of media journalism, whatever you call the parent category, there’s news, there’s analysis, there’s investigative, which I think is what, when we hear journalism, we think more around the investigative piece, there’s profiles, which is what we do here on upside, and then there’s opinion, which is, this is my opinion. And a lot of times, those five kind of categories aren’t perfectly segmented. So a lot of times you can have opinion masquerading as news. I think that’s the one that gets the most clicks, and is the easiest to get eyeballs. There’s also opinion masquerading as analysis, there’s, I don’t know, I feel like there’s this world of media is more nuanced than we, as a society kind of give it credit for. And Tom kind of brought that up around what they were doing at Insider Louisville, and how hard it was to get sponsors because they were journalism, not media. And now that their media, it’s easier to get sponsors because they’re not being critical of anything. So it is a hard act to balance when historically, all of that has existed in newspapers, which were journalism.

Jay Clouse 42:35
Yeah, totally. I feel like journalism is rooted in this ethos of being totally unbiased and just telling the facts, which is just so innately hard to do, because everyone has inherent biases of some degree. And it also seems that culturally, we have devalued that type of media. And you know, in our recent history, we’ve even villainized it to some degree. So, yeah, journalism is a tough game probably underappreciated, both for its difficulty and for its impact. But lucky for us, Eric, we’re a podcast and we can do whatever we want. We can we can throw some bias out there.

Eric Hornung 43:15
We are not journalists. You heard it here first, and second, and third, fourth, however many times you need to hear it. We are not journalists.

Jay Clouse 43:23
We love to hear what you think. Do your listener are we entertainers? Do we entertain you? You can tweet at us @psideFM and let us know.

Eric Hornung 43:30
Do I amuse you? Am I funny? Huh? Like a clown? Am I funny to you?

Jay Clouse 43:34
Started laughing? You laughing at me? If you have some longer thoughts as to the future of journalism or the opportunity for localized tech journalism, you can email us and we’ll talk to you next week. That’s all for this week. Thanks for listening. We’d love to hear what you think about this episode. So tweet at us @upsideFM or email us Hello@upside.FM and let us know. You can learn more about us and browse our entire back catalogue of And if you love our show, please leave a review on Apple podcast that goes a long way in helping us bring high quality guests to the show.

Interview begins: 7:00
Debrief: 38:33

Tom Cottingham is the founder and CEO of Flyover Future.

Flyover Future is a digital newsletter covering innovation and start-ups in the heartland. They cover the investors, the innovators and the ecosystems that help innovation thrive. We help our readers discover the amazing companies and initiatives throughout the midwest that make Flyover Country a vibrant center of 21st century innovation.

We discuss:

  • Print Media 10:58
  • Launching a Media Company 12:16
  • Louisville’s Business Model 13:59
  • Curating Readers 17:07
  • City Based vs Topic Based 22:21
  • Generational Opportunity 29:39
  • Who’s Important? 32:41

Mucker Capital was founded in 2019 and based in Louisville, Kentucky.

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