CC038: Casey Allen // building the Twin Cities enterprise SaaS community

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Casey Allen 0:00
Here’s my take, here’s here’s how it breaks down. Starting a company is already going to be hard enough. It just, it’s like every aspect of it is brutal. You’re doing everything. You’re doing 110 things for the first time, every day, and the world is conspiring against you. And so maybe, just maybe it’s in your best interest to take a look around and try to identify the cities or the markets that seem to have a ton of success in what you’re doing.

Jay Clouse 0:28
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.

Jay Clouse 0:56
Hello, hello, hello, and welcome back 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 Job, Who Dis, Eric Hornung?

Eric Hornung 1:07
New job, who this? Oh, that’s me. That’s Eric. How’s it going, listeners? I have a new full time job. I know you think that I do Upside full time all the time. But it turns out, doesn’t pay the bills as much as you would like. So I do have a full time job. Really excited to be starting a new one.

Jay Clouse 1:28
And what is that? Tell us about it?

Eric Hornung 1:29
Oh, you want some details?

Jay Clouse 1:31
I do!

Eric Hornung 1:31
You want the inside scoop? Okay, well, I’m going to be working at a firm called RKCA, stands for Rippey and Kingston Corporate Advisors. It’s in Cincinnati in Mount Adams, which I recently learned is the home of the first vineyard in the United States. Littlle fun fact there.

Jay Clouse 1:49
I thought everybody knew that.

Eric Hornung 1:50
Did you know that actually,?

Jay Clouse 1:51
I did not.

Eric Hornung 1:52
Okay, well, hey, look, I taught you something. My job is going to be a mix of investment banking and direct investments heading into an area that I find particularly interesting. When Jay and I started this podcast, we said that we existed at the intersection of finance and entrepreneurship, and I was the finance and he was the entrepreneurship. I think that’s proving true in my newest role.

Jay Clouse 2:15
Still true. It’s good to get a look behind the Eric Knight Hornung curtain. I feel like we never spend any time talking about what you do outside of Upside. And we talk about my stuff a lot. So, you know, it’s good to, good to see you trying something new, taking on a new challenge.

Eric Hornung 2:31
The world of finance is clouded by agreements and stipulations, specifically when there’s litigation involved or potential funding rounds involved. So a lot of the things that I do you can’t really talk about as publicly as something like a Freelancing School or an Unreal Collective. Plugs. Nailed the plugs.

Jay Clouse 2:53
A unreal collective

Eric Hornung 2:54
Did that bother you?

Jay Clouse 2:56
How do you feel about going from a remote role to an fffice role?

Eric Hornung 3:00
So we talked a lot about the remote workforce here on upside, and specifically the trend in growing your distributed teams or company’s distributed teams, and how that’s going to impact a lot of things. And in the startup space, I think it’s much more common than it was even 5, 10 years ago to have a distributed team. Personally, I like working in an office. I guess, I’d rephrase it. I like the ability to work in an office. I like the idea of separating home and work. And I know a lot of people will say that co-working spaces like work for that, and maybe they do, maybe they don’t. I’ve never really had the opportunity to use them. But for me, I like the idea of having an office, so I’m actually pretty excited about it.

Jay Clouse 3:41
Speaking of starting new enterprises, today, we’re talking with Casey Allen, the founder of Enterprise Rising, which is a conference for enterprise SaaS startups. Casey is also the co-founder and partner of Skyway Fund, which is Minnesota’s first true tech seed fund. Funding exciting early stage software companies doing cool things in b2b SaaS. Skyway fund has made 14 investments and had a couple of exits. We were introduced to Casey from Kevin McArdle, fan of the podcast, Kevin McArdle, who is a big Minneapolis and Twin Cities supporter and supporter of the show. When we asked him of any guest that he thinks we should definitely have on the show, he pointed right away to Casey, said, Casey is the guy for Minneapolis. And finally, we got him here.

Eric Hornung 4:31
And I just want to throw in one little anecdote about Casey. When we got introduced to him, he sent us, well, he first reached out and said, How can I, who can I connected to in Minneapolis? Even before he was going to be a guest on the show. And I said, here’s a list of criteria for the type of people we want on the show. Here’s our bread and butter, our sweet spot. Usually what happens is people send over a list of people in an email, and they say, Hey, here’s this, here’s that, or they just send a list of names. No, Casey sent an Excel spreadsheet with all of the criteria listed across the top of the spreadsheet and notes about each of the individuals based on our criteria. It was the most thorough double opt in I’ve ever seen. So don’t know what that means for this interview, but it definitely means that I was impressed by his connecting abilities.

Jay Clouse 5:17
I’m sure we’ll learn a lot here about Minneapolis. And as we go through this interview, dear listener, you can tweet at us @upsidefm what you’re thinking or you can email us Hello@upside.FM if you want to send a similar list of spreadsheeted potential guests to us, feel free to email that over. And we’ll get to Casey’s interview right after this.

Eric Hornung 5:37
Jay, come with me on a quest. Come with me on an adventure. Are you in?

Jay Clouse 5:41
I’m in!

Eric Hornung 5:42
All right. I want you to start a high growth startup right now. What’s its name?

Jay Clouse 5:46
The Haberdashery.

Eric Hornung 5:47
The haberdashery. It’s a very traditional startup name. Google Zynga Haberdashery. Alright.

Jay Clouse 5:55
Tip of the hat to that name.

Eric Hornung 5:56
That’s a, yeah, that’s that’s a nice one. So let’s say that you go out, and you want to hire some great engineering talent to get this thing off the ground. What are you going to do? Where are you gonna go?

Jay Clouse 6:06
Well, I would probably first go to my own network and realize quickly that I don’t know enough engineers.

Eric Hornung 6:11
Right, and with a name like the Haberdashery you’re gonna have a tough time recruiting.

Jay Clouse 6:15
Tough time. Tough time. I might need some outside help, Eric.

Eric Hornung 6:18
Yeah, I think if I were you, I would go to our friends over at Integrity Power Search. I mean, they’re the number one full stack high growth startup recruiting firm between the coasts. They partner with venture capitalists, private equity groups, and hypothetical CEOs like you to build amazing teams for the world’s most disruptive companies. Since 2012, they’ve successfully executed over 600 searches. So that sounds like you’re starting engineers, Jay, we could get those, all right, we can get those with IPS. And they are on track for over 200 in 2019. Their clients have collectively raised over 2.5 billion with a B in venture funding, and, hey, maybe with the Haberdashery will be counting

Jay Clouse 6:58
If they can help the Haberdashery, they can help you learn more about Integrity Power Search, and they may just be able to help you find your first engineers.

Jay Clouse 7:15
Casey, welcome to the show.

Casey Allen 7:16
Hey, I’m happy to be here, guys. Thanks so much for the invite.

Eric Hornung 7:19
On upside, we like to start with a background of the guest. So can you tell us about the history of Casey?

Casey Allen 7:24
Sure, the history Casey is launching random stuff. Did five startups. And then recently have been all in doubling down on the startup ecosystem where I live in Minneapolis, Minnesota. So really wrapped up in there as Minneapolis and St. Paul, the Twin Cities. And so I’ve been, for the last, let’s say, nine years, I’ve been in an investor. I’m an investor in 14 startups. I’ve been an advisor in dozens more, mentors to hundreds more. I’ve launched a couple conferences and a couple of events. And now wanting something new for 2020 that is focused on helping startups recruit and hire more effectively.

Jay Clouse 8:03
Of all the things that you’ve been involved in, what has been the most difficult?

Casey Allen 8:07
The most difficul? Once a year, I run a conference called Enterprise Rising in Minneapolis. I just had my fourth one last July. And we’re recording this right now in late October. So I, when I first started this conference, it was unbelievably more difficult than I thought. I thought because I had a network, I thought because I had a decent enough following on social media, that I would be able to pack the place without barely lifting a finger. And the hard kick in the teeth for me about launching a conference from the ground up was how hard it is to do without a mailing list. I didn’t have a mailing list. I didn’t have anything resembling a mailing list. And I was gunning for 300 attendees out of the gate. I think I ended up selling something like 80 tickets. Eighty tickets, guys, like what a what a drop from the goal or the objective. And of course, it’s gotten better and better year after year, it’s grown at probably 75% year on year. And it’s now one one of the most amazing or it’s probably the highest quality content conference in the Midwest, as told by other attendees that come from out of state. But the beginnings were very, very difficult, much, much harder than I would have thought with many, many more false starts and failures in terms of things that I thought would fall into place easily but that did not. My first keynote speaker gave me a soft yes. Today, he’s a well known celebrity, whose name I will not drop, but when people talk about tech startups like he’s a top 10 name. Back then he was not. Gave me a soft yes, and said I just need to take a look my calendar, figure out travel. Then continued to go radio silent on me for 10 weeks straight. I followed up with them every five days. Hey, what are your thoughts? Hey, is this going to work? Hey, what about these days? Hey, what about this time? Hey, can we jump on a 15 minute call? Nothing reduce it. Every single time, aand I ended up having to change the date of my conference, which is not the end of the world. But I had to change the date of my conference to accommodate my new keynote speaker. And the new date of the conference ended up being 10 days after my wedding. And I almost had like six nervous breakdowns because I was planning my wedding and planning my first conference where nothing was going right. And everything was on fire, all at the same time. It was brutal. So I took something that was already hard to do, a conference, which is even harder being it’s the first one, and then even harder, because nothing was going right including my keynote speaker. And then if you package that into 10 days after your wedding, man, was that hard. Do not recommend

Eric Hornung 10:41
Why’d you do a second one? By all accounts, eighty out of 300 isn’t a great number.

Casey Allen 10:47
That’s a terrible number. And I lost seven grand on my own pocket, but that’s kind of the cost of admission for me of wanting something new. I’m okay with it because I’ve launched enough things in life to know that the first is always the hardest by an order of magnitude. The first everything is the hardest. I don’t know if you guys remember back like the first episode that you did, but like just getting everything into place was a little more stressful and a little more like, What the hell are we doing, we were figuring everything out, all the tools, all the processes for the first time. You remember?

Jay Clouse 11:20
I do, and I have this mantra generally of anytime I’m struggling with some project that I’m doing, I always tell myself, this is the hardest it will ever be, which is always true. I think.

Casey Allen 11:29
It is always true. That’s like the ultimate fortune cookie with keeping in your wallet forever and ever, because it is so true, and if you can internalize that, then at least you won’t throw in the towel after the first one saying oh my gosh, was so hard. So I’m partially crazy and partially experienced enough at launching new things that I realized like nothing was going to be as hard as the first one. And now I’ve got all these lessons learned, including what is really important and what really is not important. And so I knew that the second one was going to be easier, and in fact, it was a little bit easier and the third was a little bit easier, and the fourth now is getting a little more cookie cutter. And now it’s something I look forward to, whereas before I was a stressed out mess every single time.

Jay Clouse 12:09
You were referred to us by our friend Kevin McArdle as the guy in Minneapolis to talk about Minneapolis. So at the beginning of this adventure in the first conference that you had, was that the beginning of you becoming this guy for Minneapolis?

Casey Allen 12:24
Probably not. Probably me becoming the guy, if I had to pinpoint one thing is when, back in 2009, myself and another entrepreneur started the first ever Seed Stage Tech Accelerator program, an accelerate program similar to let’s say, TechStars. You guys have had Joe, the cofounder of gener8tor on the podcast several episodes ago, which is a great listen. So those that don’t know, gener8tor is a great accelerator program out of Madison. And they operate many, many programs all around the Midwest now. But back in the OG wild, wild west days back in 2009, there were not many accelerators around. And I was really inspired by what Y Combinator was doing, and what TechStars was doing. And now there’s a kazillion TechStars programs all around the world. But back in 2009, there was three: there was Boulder, Seattle, and they were just launching one in New York as as I got started. And so I launched an accelerator program, and there’s probably, you know, there’s no better way to rocket yourself into the middle of whatever tribe it is that you feel like you are affiliated with, or that you have the most in common with then to launch something that is bold and something that is ultimately helpful to all everyone involved. And launching an accelerator program is helpful for everyone. It’s a lot of work, and it takes a lot of credit and a lot of capital, but it brings together all the critical ingredients that help a community go from zero to sixty really, really fast. And so back in 2009, 2010, we launched that. It was a big deal. Back in the US, there was probably only like 15 accelerator programs. By the time we started our second cohort, I think that had blown up to like 200. So it was, it was, it was crazy, like how many accelerator programs were launching back in those days. We take it for granted now. If you’re in the tech world or the startup world or in the investing world, you look around, and they’re everywhere. But it’s hard to imagine once upon a time, there were not that many of them. So if you had the point where I, let’s say, had my coming out party in a fairly significant way, it was by doing something that was really hard, and at the time pretty bold, and at the time, really labor and energy and money intensive, and something that helps the entire community all in one fell swoop, and launched an accelerator. So if you, this is especially true if if you’re in a smaller market, so if you’re listening to me and you, you live in, I don’t know, Bismarck or you’re in Boise, Idaho, and you’re like, Well, how do I become somebody important? Do something really, really hard that helps the entire community. And it’s going to kick your ass and you’re gonna need a lot of reputation, a lot of money. And if you don’t have reputation or money, find people that do. Bring it all together and make it happen.

Eric Hornung 15:09
2009 was like the pit of the Great Recession. Not a lot of people had a lot of money ready to go at that time. How did you raise money for a risky proposition in the Midwest in the depths of the Great Recession? Like what was that fundraising process like?

Casey Allen 15:28
Sure, so we skipped the fundraising process and self funded it. So there was two entrepreneurs, myself and my co-founder, and we didn’t raise a fund. That’s the default these days. And that’s how most accelerators, virtually all accelerators, actually, like 99.9% of all accelerators, that’s the business model underlying it, which is go out raise a fund, the fund will run anywhere from one to three cohorts, hopefully you’ve got a couple success stories. Hopefully a couple of companies have gone on to raise some sizable series A’s, maybe a Series B or two, and then you go back to the same investors or bigger investors to say, see what we’re doing works, give us more money. We wanted to simply prove it to ourselves and prove it to the world first. So we just self funded everything.

Jay Clouse 16:10
If I was going to start an accelerator now and self fund it, how much would I need to self fund to give myself a realistic chance? Is that still possible in 2019? And what were your metrics of success? Three questions.

Casey Allen 16:23
Okay, so our metrics of success back then were simply to get companies to a point where they could credibly raise a seed round. And if they could raise a half million, a million dollar seed round, then we knew that we were preparing them for the journey ahead. Like there’s probably no better asset test quite honestly to afford is an accelerator succeeding. Or if you’re a founder, and you’re looking at a particular accelerator, like huh, this accelerator looks interesting, maybe it’s got some kind of Industry focus. So maybe it’s focuses on health tech or just on transportation or logistics tech, like, hmm, this looks interesting. I wonder if they’re actually good at what they do. We’ll head over to crunchbase and do a little homework, and in 30 minutes, you can discern yourself. Do at least a meaningful amount of the graduates, let’s say at least 10% of the graduates, seem to have gone on and raised defacto seed rounds? So that’s the acid test of successi, is the accelerator actually succeeding? If the accelerator cannot get companies to raise seed rounds, then that probably means one of two things, they’re not very good at accelerating–so something is fundamentally broken and or they’re run by the wrong people–or you’re probably trying to start an accelerator in a market that simply is not set up well for follow on funding. So if you’re trying to launch an accelerator in Portland, Maine, you might want to pause and actually look around and say, well, jeez, how many real angel investors, right? Let’s say three checks a year, every single year in the startup into technology, startups are the kind of startups that we want to accelerate. And if you can’t, like name more than five or six people, then maybe you shouldn’t launch an accelerator in Portland, Maine. And I say this not to be demoralizing, but rather to help anybody focus their effort. You can replace the term accelerator with fund, you can replace it with any other program that is structured to help entrepreneurs. It doesn’t have to be tech. But it’s, it bodes well for you to actually pause and look around and say, is there already some success here? Is there already early stage capital, if that is our goal to prepare companies for early stage capital, and if there is not really safe capital around, then maybe we need to change what our goal looks like. So back then, that was our metric for success or that’s what we were gunning for. If you wanted to launch an accelerator today, the bar is very, very, very, very high. And it should be high. Because now we’ve got a lot of kick-ass programs all around the world that have been operating for years and years and years. They have the playbook refined, they’ve got the network refined, and you are essentially competing against them. So you can run a mediocre program. I mean, have at it if you’re, if you’re perfectly happy being every entrepreneurs like ninth choice,. But if you don’t want to be every entrepreneurs ninth choice on accelerators that they’re applying to, then you need to either pick a niche that you believe that you can crush–and you can probably go incredibly, incredibly niche for an accelerator program, like I’m talking, don’t just focus on health tech, for example, focus on like aging health tech, or focus on, like screw health tech focus on like, technology for pets. Okay, trillion dollar market, and there’s not a single accelerator out there. And I’m throwing out these ideas because if you can be the only or be the best accelerator for any startup in the world that’s doing interesting things for pets and their owners, well, guess what? You’re not competing against YC and TechStars. You’re not competing against anyone. So from a financial standpoint, you need to come pretty prepared still. The table stakes these days is funding every startup probably $75K. That’s going to become $100k in the next two years. So if you can’t seed fund an entire cohort $75k And you can’t gather a team of two or three full time employees, because running these things takes a lot of effort, and if you can’t, you don’t have the reputation necessary that people believe you could pull this off, then you need to find other people that will. But for all practical purposes, if you can’t scrounge together half a million of your own money or from other people, then it’s going to be you, you are setting yourself up, up and everyone else up for failure.

Eric Hornung 20:27
How did you build the reputation to get to the point to launch an accelerator?

Casey Allen 20:30
I’ve been an entrepreneur, been a successful entrepreneur. So that helped, but although it should be noted, I’ve never, I don’t have any exits under my belt. So in a lot of ways, I was proven but not super proven. I had done it but not done it big. All my startups were madly profitable, which was the only way I knew how to build them. But I had, what I had in a lot of ways was the right thing at the right time. I had the ability to connect very rapidly with a bunch of people in the community that were linchpins that would throw their support, throw their time, throw partially their reputation behind what we were trying to do. We had the gift of being novel. So when you’re the first at what you do, and in our case, we were the first seed stage accelerator in Minnesota than that, you can actually get a lot of mileage on that. These days, yhat would not be the case. But you can get a lot of mileage by being the first, you can get a lot of mileage by being clear that you’ve got skin in the game yourself, for example, you know that you’re not taking state or federal money or public taxpayer money. That’s very meaningful to a lot of people that we did not on purpose. And then just knowing that your heart was in the right place, which sounds very mushy, but it was pretty clear to anybody that spent 20 minutes with me why I was doing this and why I was all in on this and why I was focused on trying to launch and put this together and everyone knew is a lot of work. But everyone knew my intentions were pure, versus let’s say my intentions were either just seeking fame or seeking fortune, which are terrible, terrible reasons to launch anything helping entrepreneurs, because it will not bring you fame or fortune anytime soon.

Eric Hornung 22:13
Why do you care so much about the Twin Cities specifically?

Casey Allen 22:17
I like, I’m born and raised here, and I like the area. And I want to live here for a very long time. And I care about helping entrepreneurs because when I think back to my entrepreneurial venture or my days, my journey, when I think back to my journey, I made it so much harder on myself than I needed to. I essentially was on a self imposed island with no entrepreneurial friends and no entrepreneurial mentors. And I mean, it’s so, so, so much harder on myself mentally, emotionally than I needed to, and that’s on me. That’s nobody’s fault but mine. I was not very resourceful. I didn’t seek out other people. So as a result, like my typical week was on Monday, I’d wake up ready to take over the world and by Friday, I’m ready to jump into a bathtub with the toaster. And I didn’t have support, I didn’t have somebody to call, I didn’t have entrepreneurs sharing their stories, like Dude, this stuff is really tough, like you think you have it hard, I just went through this like six months ago, I decided to fire my CFO and, and layoff, you know, two thirds my team because we just lost a huge, we just churned a huge contract, and a revenue now is down 40%. And like, I didn’t have anything to compare to. And I didn’t have any therapy. My only therapy was Andrew Warner, which I watched religiously back in the very early days of Mixergy because it was the only exposure I got to entrepreneurs because I didn’t have any entrepreneurial friends. I had great friends, just none of them were entrepreneurs. And so they all thought I was crazy all the time and always wondered why I just didn’t get a real job. So when I wake up every day now thinking about how can I allocate my finite time and finite energy, finite money, finite everything. I just think about what Archimedes levers do I either have or can I build really, really fast, that help other entrepreneurs have a much lonely time? How do I get the right people in the room to help entrepreneurs get to the next level? And if I can do that and save any founder all the pain and anguish that I went through unnecessarily earlier in my like in my 20s, then I feel like my job in life is done.

Jay Clouse 24:15
Do you think that those support systems and other entrepreneurs, those people that you could have gone to existed or was this just a very different time in Minneapolis?

Casey Allen 24:24
They totally existed and, and I, I should have had the hustle to find them, even though this was pre LinkedIn and it would have been slightly harder for sure. I mean, there’s, this is actually a very common fallacy. When I started the conference in Enterprise Rising is the conference,, if anyone wants to check out what I’m talking about., hundred percent startups, hundred percent Midwest and hundred percent enterprise SaaS. I started the conference largely because I was annoyed at how many people kept trying to compare us to Silicon Valley. Oftentimes we’d be like at an event or a conference, or somebody would raise their hand and ask the speaker or ask the panelists the question that I just hate the most, which is how do we be more like Silicon Valley? And it’s usually at that point, I would just get up and leave the room because everything that follows that is just going to make everyone dumber. It’s, it’s a terrible question to ask, and it’s a very unproductive conversation to have. And so I started the conference mainly just because I wanted to plant a flag on the ground, and try to get everyone to celebrate what we do have and what we are awesome at. And it’s my thesis that Minneapolis, St. Paul, the Twin Cities is quite possibly top 15 in the world of enterprise SaaS, depending on what you want to measure. And it’s still, it still baffles me at times when I run into people, and they…The reason why people bring up Silicon Valley or want to bring up, Why don’t we be more like Silicon Valley, is because it’s lack of awareness that the city or the market or the area of the region that they’re in actually is good at something. And I don’t know what that something is, but it just means that this person isn’t aware or isn’t plugged in at all to the scene. So they’re kind of an outsider or an academic looking in, and they’re not aware of what is, what is succeeding or what is going well. And if they knew what was succeeding and going, well, then they wouldn’t ask those kind of questions. And if they knew what was going well, then they wouldn’t feel like the region has to change or something, something big has to like somebody has to come in and save them. They don’t they wouldn’t be waiting for a savior. Because at the end of the day, I think every region has its own strengths, their own, I guess centers of excellence. We’re great at enterprise SaaS. Chicago is amazing at FinTech, specifically b2b FinTech. Indianapolis not surprisingly is becoming quite the hotspot for anything revolving around marketing technology or marketing SaaS, probably due to its DNA from Total Expert and now Salesforce, and it makes sense. You know, Seattle is always been a big gaming hub. And if you’re a gamer, then it’s in your best interest, perhaps, to pick up and move to Seattle because of the DNA that was created from from Nintendo and Sega and EA over the years. So if somebody isn’t aware of how to get connected, they’re going to have some really bad opinions that they’re going to give to founders, and they’re also going to have bad opinions about their own region.

Eric Hornung 27:14
How often are you telling founders, hey, Minneapolis might not be the place for you to launch your business, if they’re outside of b2b SaaS?

Casey Allen 27:21
More than you would think. And I get a lot of flack for this both on Twitter and just elsewhere. But probably, I would say, two to four times a year, I will say to a founder that this is for sure, if they are raising a, let’s say, a seed round, because they’re at this pivotal point, this juncture in their startup, where they’ve already convinced themselves they need to raise money. So I’m not, I don’t really want to be in the business of trying to convince them they don’t need to raise money. But if they if they decide that’s part of the the roadmap, and it’s not the investor base here is not well suited to it. So for example, there was a, there was a startup not too long ago, they’re a marketplace business, two sided marketplace. And the truth is that we don’t, we are not a big marketplace town, I guess you could say, like we haven’t had any big two sided marketplace successes. We don’t have any, we don’t have a lot of founders running around that have had, that have had exits, and that understand two sided marketplaces. Therefore, like local angels don’t really understand the metrics around that. And what is, what does a successful two sided marketplace look like when it’s succeeding? So if you’re a two sided marketplace, like honestly, I think you should spend virtually all your time fundraising in Chicago if you’re here in Minneapolis. And Chicago, because, a, it’s close but, b, Chicago has a ton of investors that are really, really good at at two sided marketplaces. I call it the Groupon effect. But there’s now so much DNA and so much early stage capital in Chicago and talent that understand how to, how to ramp up the two sides of a two sided marketplace. The chicken and the egg, how to do that effectively. Also any kind of b2c play, if you’re a b2c play I think…Here’s my take here’s here’s how it breaks down. Starting a company is already going to be hard enough. It just is, like every aspect of it is brutal, you’re doing everything, you’re doing 110 things for the first time every day, and the world is conspiring against you. And so maybe, just maybe it’s in your best interest to take a look around and try to identify the cities of the markets that seem to have a ton of success in what you’re doing. And maybe, just maybe, it’s in your best interest to move out there and get things going when you are surrounded by the very people that understand exactly what you’re doing and can add tremendous value. And keep in mind, like founders, you can move to a city and then move back home in like two or three years once you’re really, once you’re kicking ass and taking names. Like once you get to like series A, like you can pretty much you know grow the company anywhere you want once you have the necessary traction where investors are fawning over you, then, then you can you can geographically be wherever you want. But in the early, messy, I still have to prove myself to everyone and I have to prove myself to to investors, like maybe it’s in your best interest to pick up and move. Because if it’s in your best interest, the good news is, anybody that matters will applaud you for making that decision. I mean, if you’re like an insurance tech startup, like maybe, just maybe it’s in your best interest to pick up and move to New York City for two years and make a go of it or more importantly, just join an accelerator program that focuses on FinTech, wherever that happens to be, and just stay and make that your home for the next year as you raise your first rounda and as you hire, make your first two or three key hires. It’s in your best interest like startups are hard enough. Don’t start…You know, nobody moves to Florida to start an oil field. Right? I mean, you go where the action is. There’s a reason why people move to LA to join entertainment or to be an actor. It’s because they’re surrounded by all the necessary ingredients that will help them get to the destination that they want to the fastest and easiest. Now, there’s probably this rare exception of the Bay Area just because the costs are now crushingly prohibitive. But if you take the Bay Area out of that whole conversation that I just said, I still think it’s to every founders advantage to ponder, even if you have a family, even if it’s going to be hard, like to ponder, maybe it might make sense for me not to start this FinTech company in Omaha, Nebraska. It might make more sense for me to go to New York, at least for the next year or two or three, to get things off the ground to really get to a point where I’ve got leverage, and then I can move the company back to Omaha or wherever I want.

Jay Clouse 31:48
What was the pattern that you saw or the the moments where you realized enterprise SaaS is a key part of the Twin Cities DNA?

Casey Allen 31:56
Well, partially I’m just lazy, and three of my companies were b2b, so that’s what I get and I understand. So I, I have a unique appreciation for b2b. And I just like companies that make money from day one. I just, I really do. I really like versus a b2c or some kind of a social play where you’re bleeding money for forever and ever and ever and ever hoping to somehow find a business model down the road. But it’s, it’s also just, this was actually back when I started the accelerator program, my co-founder and I both had b2b backgrounds. And so we just, we just naturally gravitated towards, like all the almost all the companies I think that we accepted to the program were b2b. It’s just it’s what, when you ask yourself the very, very important question, if you are in the business of helping entrepreneurs succeed, okay, which is a privilege and a very sacred job, it’s worth asking yourself like what am I actually well suited to help them with? I mean, there’s probably a lot of stuff that I’m not. I, I don’t know if a gaming, let’s say a crypto founder came to me. I don’t know anything about crypto I don’t pretend to. And I don’t care too. And so I will tell them right off the bat, like, Listen, I’m worthless to you. I’m just deadweight. I’m happy to make an introduction or two for you to people that are much smarter than me, but like, you don’t want to spend much time with me, I’m a waste of time. Same is true of any kind of gaming founder, like I don’t understand gaming, I’ve never been a gamer, I don’t, it’s not a world that I know I don’t hang out with gamers. I’m of zero value, I’m a negative value. There’s a lot of things I’m a negative value for. So b2b though, I actually can add value. I consider myself quite helpful getting a founder from zero to a million in rev. After that, I’m probably not very helpful, or my value wanes very, very fast, but zero to a million, or for sure, zero to half a million, very, very helpful. And so I know that. But there’s tons and tons and tons of stuff I’m not helpful at. So we picked b2b because both of us were comfortable with that. We liked it. And also, if you just do some cursory looking around or asking around of, Well, what gets funded in our region? That’s a very, very worthwhile very important question to ask, like what gets funded. And again, you can spend 30 minutes on crunchbase some evening, just kind of whittling it down. It’s not that hard to discern. And it shouldn’t be a mystery to anybody that’s in the business of helping entrepreneurs succeed. And if you’re helping bootstrapped founders succeed, that’s probably a different conversation. And you don’t have to focus on that; you can focus on other things. But it is worth focusing on what industries are strong, because you’re helping a bootstrap founder that sells to banks, and you are not in a very bank rich environment. Maybe it’s worth asking the founder some other tough questions like, can they go after something adjacent to banks? Or maybe they’re in the wrong market to launch this company.

Jay Clouse 34:48
Earlier, you said that you didn’t have any exits under your belt, but your companies were mad profitable. What happens at the end of a company’s life that is profitable that isn’t an exit?

Casey Allen 34:58
Okay, so I did this totally wrong and no founder should ever follow my path in life. I was very ADHD, and I took a very scattered approach to all of my startups, where I would launch a company and run it for two or three years, and it would spit off, like, 90% margins, and I’d get into like, significant six figure revenue, and I’d hire a handful of employees, maybe anywhere from two to eight employees, and then I would get bored or I would think of something that I thought was bigger or better. And so I would, I would slowly wind it down, that startup, and jump to the new thing. And then two or three years later, I would wind that down and jump to the new thing. Sometimes the employees would come over and sometimes not. But it was, I had no staying power. And that was partially because, and this is the first time I’ve actually admitted this publicly, I was scared to death of success. Actually, this was actually a psychotherapist actually diagnosed me with this. Had to do with how I was brought up and having a dad that never wanted to see me succeed, so he essentially cut me down every chance I was doing something positive in life. But whenever I got to some critical juncture of somewhere around, like, let’s say, half a million in revenue, like I would find all kinds of ways to talk myself out of continuing running the company. So I would literally sabotage myself. And part of the rationalization or sabotaging is like, Oh, you know, this has been going well, and it’s a great I’ve got all these customers and now, things are just rolling, money’s just rolling in. But man, there’s this other idea over here. This industry is so much bigger. Like I feel like I could scale this one up like so much faster, even though the word scale wasn’t invented yet. And then, so I would do that and I rationalized myself. And so I had this fear of failure, but it was also a fear of success. Sorry, I did not have a fear of failure. If I had a fear of failure, I never would have launched anything to begin with. I had a fear of success. And now I’ve dealt with that in my own ways, but the part around me being lonely as an entrepreneur and being so undisciplined that I didn’t surround myself with anybody that could kick me in the rear when I needed it, like, that’s something I look back with an enormous amount of pain and resentment towards myself that I’d never had any mentors that could beat me over the head and say, Casey, what are you doing? Like, what are you doing shutting down, you know, this startup and starting a new one, like you’ve got the makings of something big. So either hire a new CEO to replace yourself, which I just didn’t have the maturity to do, or like, stick with it and try to figure out what’s, what’s going on inside your head that’s, that’s making you want to bail on this company that’s already working. So I look back and I wonder what I could have built if I actually had the discipline. And I didn’t have the discipline because I wasn’t surrounded by anybody that would beat me over the head when I needed to be beaten.

Eric Hornung 37:55
Now you’re in the position to be able to using your words beat people over the head with this method. Do you see founders having this same fear of success? We hear so often this idea of fear of failure and not getting started. But when you’re advising the hundreds of founders you’ve talked to, is this a common trait? Or is this–are you an outlier?

Casey Allen 38:18
So far, I haven’t come across anyone. And just so you know, here’s, let me try my best to explain what I would look for in terms of somebody that had a fear of success. Fear success means that by every objective measure, what you’re doing is working. So your customers are happy. Your revenue is increasing month on month or year on year, and your employees if you have any seem happy. But you’ve convinced, that you’ve told yourself a story in your head that you need to stop doing what you’re doing and do something else. And that something else could be another startup, it could be I need to go, you know, work for some nonprofit like whatever it is, and I would, if I’d met an entrepreneur that was like that, I would–and I have not–I would probably grill them for a long time with some very probing questions, trying to find out what is really underneath this decision that they’re trying to make. Of course, fear of failure is far more common, and the easy way to see fear the fear of failure is where a founder is stuck in the research stage for like a year. Right I’m going to start this company, I’m starting this company, I’m in the process of launching this company, we’re going to start, we’re going to launch next year. But they’re in this perpetual state of research and planning and coffees and coffees and coffees and coffees. So that’s the, that’s the unfortunately, the American way of being, of having a fear of failure is to look like you’re starting a company even though you haven’t taken a meaningful steps towards starting a company.

Jay Clouse 39:46
Do you think of Enterprise Rising the conference as a start up?

Casey Allen 39:51
Yeah, I suppose for the sake of this conversation, yes. And for the sake of like, Is it a scalable fundable fast growing something or other? No, of course not, but it has a lot of the elements of a startup. So even though I don’t refer to it as like one of my startups or like, when I say I’ve had five startups, I don’t refer to this as one of them. But it’s, it’s got all the elements of a startup, for sure.

Jay Clouse 40:15
So how does that affect how you run this conference or measure the success of this conference in spending what I imagine is a ton of time on it year over year?

Casey Allen 40:25
It is a ton of time. Have you either have you guys ever been a part of launching a conference or organizing conference?

Jay Clouse 40:30
Startup Week.

Casey Allen 40:31
Ah, there we go. I started week is a lot of moving parts, for sure. So yes, the conference takes me 1000 hours a year. So it’s not trivial to me at all. Of all the things that I, all the plates spinning that I have, it is easily the most time and energy intensive thing on on my plate right now. And it will be for at least a few more years. Here’s how I measure success. Totally different than everyone else. Probably different than any other conference organizer. I measure success by how many founders after each enterprise rising conference tells me that it changed their life. I don’t care that much about profit, I don’t care that much about revenue, although it is insanely profitable now, thankfully, my days, the days of losing seven grand out of my pocket or over, I’ve got amazing sponsors that renew at 92% success rate or renewal rate every year. So that’s almost like recurring revenue, which is pretty cool. An I’ved raise ticket prices over the years quite a bit to weed out those entrepreneurs that I really don’t care to have in the room. But my success is driven by everything that I do is driven by validation. So I, I need validation. If I’m cranking away, doing whatever I’m doing, and an awful lot of the things I do are not for money. There’s a lot of things I do that are not creative at all to my financial life. And I’m fine with that. As long, as long as I can keep other parts going just fine. The conference is no exception to me needing to know that founders are getting not just that it was a good time, not just that they learned a thing or two. But I really need to know that the conference really jolted them and really changed their trajectory. And so that’s why a lot of the talks that I have are not the kind of talks that you would find at other conferences. I mean, we had at the last Enterprise Rising conference, I had one very successful founder up on stage, outlining in detail like how he balances his marriage and how he blocks off certain days where he will not fly. And how one day week he ditches his cell phone and he’s all in on his kids and his wife. And he’s got one date night a week. I’ve got another founder, the listeners might be familiar with Ben Milne, founder of Dwolla. I mean, he said on stage like, you know, my days of working 80 hour weeks are over, like I don’t, I don’t need to prove myself worth in this world anymore byhow many hours a week I work. And so I think that was very surprising to a lot of founders in the audience who probably just assumed Ben Milne and every other successful founder that’s backed by Andreessen Horowitz and by high alpha VCs and, and is an industry leader in their industry, they probably just assume these people are working like maniacs, and it’s just not the case. You know, I had Rob Walling from who sold Drip to Lead Pages and now runs Tiny Seed, which is a very, very, very cool new accelerator model for bootstrap founders.

Eric Hornung 43:32
Also been on the podcast.

Casey Allen 43:33
Awesome. And he’s a great storyteller, so if you have not listened to Rob Walling W-A-L-L-I-N-G, he is worth listening to. I had him and his wife, Sherry Walling, PhD, clinical psychologist, who has clients that she gives therapy to including many, many founders, and they got up on stage and talked about burnout, talked about anxiety, talked about how to balance this crazy thing called being a startup CEO with also being a good dad and mom, also being a good husband and wife or boyfriend, girlfriend. This is not the kind of stuff that you hear about at Disrupt or at Launch conference or at Sester Annual–and I’m not bashing these conferences, there’s a lot of value to be had by all of them. But one of the things I’m more proud of is the fact that we’re able to that at my conference I ask very, very select, handpicked successful founders and CEOs talk about topics like this, that I think founders are desperate to hear more about, and need more vantage points on of how, how to how to do the impossible how to build the impossible, but not destroy your life in the process. And so my success metric is how many founders come to me or email me afterwards and say, This changed my life and I’m very, very fortunate, now I’m at a point where I have multiple founders doing that, but that’s my bar. That’s my metric. And the day that that goes away is the day that I would probably lose interest in doing the conference.

Eric Hornung 45:00
I want to zoom out a little bit into Minneapolis, since you are the guy in Minneapolis. If I was reading like the intro two to three paragraphs on Minneapolis, what are the kind of centers of influence, the trends, the industries, we’ve already talked about b2b SaaS. But what are the other kind of things that I should know about Minneapolis knowing nothing about Minneapolis from a tech perspective?

Casey Allen 45:24
We’re a top hub for b2b sports tech, meaning we build software for sports leagues and teams and associations. We have an astonishingly strong record at enterprise health tech, not health tech like fitbits like that consumers use but that we sell to big companies, big enterprises, big organizations, usually to keep their employees as healthy as possible. We have a huge, we have a ton of track record of exits there and lots of funding there, including a couple of very interesting startups right now as we speak that are on the upswing that are focused on mental health. Again, selling to companies or organization saying we’re focused on mental health and making sure that your employees are high functioning and that are missing as little work as possible due to their own whatever kind of mental obstacles or mental health obstacles that they’re running into. We have a long, decades, decades long track record of edtech, specifically k-12. Not sure how that happened to be. I don’t know if you guys remember this, but remember, back in college, we had scantrons, those bubble sheets? Yea, thats a Minneapolis company, like and so I mean, that’s old, we’re talking old school, right 80s-90s. But there’s a lot of a shocking amount of those kind of companies I think paved the way for now a lot of SaaS k-12 startups here in the Twin Cities. So those are, those are three areas where specifically we’re really, really good. And again, across the board, it’s going to be b2b, but health tech, specifically, like b2b healthtech, we’re awesome at b2b sportstech, we’re awesome at, and b2b or not just b2b, but k-12-tech. We have tons of great mentors, tons of great talent, and a decent amount of early stage capital, decent enough where a founder can or should be able to with enough hustle enough resourcefulness raise that first million dollar seed round hundred percent locally.

Jay Clouse 47:19
What’s the opportunity ahead of the Twin Cities that you’re just not quite capturing yet?

Casey Allen 47:24
One of the things that I’m, I spend a considerable amount of time on is guilting more successful tech founders or CEOs into angel investing. One of the things I’m frustrated at is I wish there were more CEOs that had exits under their belt, that have done well for themselves, they got a couple million or 10 million in the bank, the mortgage is paid off, the kids college funds are already set up, the cabin up north is in good shape. And somebody has to be that guy, and I’m happy to be that guy because hopefully I’ve spent the better part of a decade building up the credibility to be that guy, to nag them or to help them or both start angel investing or more, or do more angel investing. You know, let’s say for example, a CEO sells his company for 150 million, and he did well on the exit. And now he’s on to his next startup. It’s very easy for that startup to be so heads down growing the next company where he just, he feels like either angel investing is too distracting, or he just doesn’t want to, like hang a shingle out, or she doesn’t want to hang her shingle out and get like 20 pitches a week. And I get that, I understand that. But I think that for a lot of the successful CEOs that have had success, and now have the financial means they forget that there’s this big, wide open middle part where you can still recycle some of the wealth that you have been fortunate to make back into the next stage of startups. You can be an LP and a fund. And sometimes they’re just not aware of who is actually raising a fund around town. You can invest in and fund also means, you could be an investor in an accelerator fund. You know gener8tor is launching a brand new program here in Minneapolis as we speak. And you can also, you can just, like I personally am happy to be, to send you like, let’s say, five or six deals a year if you tell me very, very specifically, what excites you like what, what jazzes you, what gets you really, really pumped up, what kind of founder, what kind of startup, or what kind of pain are they solving this world like what stage do you feel like you can be pretty helpful at where…One of the litmus tests that I give anyone that wants to start angel investing, or that says they want to start angel investing, is I ask them, you should only invest in companies in which you’ve, after the pitch, you feel like you can make five phone calls on their behalf and massively move the needle for them. And if you can’t, if you can’t, after that pitch, leave the pitch and be like, I really can’t think of five phone calls that I can make, then you should probably pass, and you probably pass because either it’s in an industry that you’re not familiar with, which is fine, but it just means that you’re not going to be, you’re not going to be super excited and can be emotionally bought in, or just means you’re not going to add much value, and if you’re not going to add much value, same thing, it’s going to be tough for you to like stay super engaged as the startup goes through their ups and downs roller coaster over the next three years. So I try to be as super helpful and try to be the gateway drug for anybody that is beginning to Angel invest, or wants to do more of it. And one of the things that, I’m launching two new things in 2020, but one of them is a one day bootcamp that teaches beginner angel investors how to get started. So maybe you’ve done zero investments, or maybe you’ve done one or two, but you still feel like you have no clue what you’re doing, like I want to give any aspiring angel investor, I want to give them confidence and I want to give them direction. And even though I don’t believe I’m the best investor in the world, one of the things that I can do, because according to Kevin McArdle, I am the guy of Minneapolis, one of the things that fortunately I’m in a position to do is I can bring into the room five or six people that have done a ton, hundreds and hundreds and hundreds of angel investments themselves. And they can share stories and they can answer questions. And so the few people in the room that have signed up for this one day bootcamp so they can learn how to be better angel investors, they can be hopefully, at the end of that day, they’re going to leave with way more clarity and way better rule systems for themselves, and then also just a better sense of camaraderie, because it’s shocking how many angel investors actually don’t know any other angel investors. So that’s one of the first things to fix for sure. Because if you told me, you know, Eric, if you came to me and said, I want to learn how to sail, I want to be a great sailor. And I asked you how many sailors you have as friends and you said zero, that’s the first piece of advice I would give you is fix that, start hanging out with more sailors. Otherwise, you’re just gonna, you won’t have staying power, you’re going to get sick. As soon as the going gets hard. You’re going to give up and throw in the towel and say, This wasn’t as fun as I thought it would be. So what is something–this is not unique to Minneapolis or Minnesota, arguably like the only place where this is super duper strong is the Bay Area where there’s this cultural norm or belief that if you have succeeded, you pay it forward. And in a lot of other markets, I’m sure if you talk to founders or investors in Philadelphia and in Dallas, and in Jacksonville, Florida, you’d probably find the same thing, like, yeah, I really wish we had more people that had money to start angel investing. And that’s tricky because you don’t want dumb money throwing money around because that’s catastrophic. But there is something to be said for taking people that come from an industry like software that have had success in that industry, that having enough money where they can afford to lose it, to start writing some checks every year, and they just need somebody to guide them. And so that’s, that’s one of the things that I’m focusing on doing is how do I help guide people that have the the interest and the passion and the money to start angel investing to do it so they don’t screw it up for themselves or for the founders that they invest in.

Jay Clouse 52:56
Casey, this has been awesome. If people want to learn more about you or Enterprise Rising or this bootcamp that you’re coming up with in 2020, where would you direct them?

Casey Allen 53:05
Sure, if the bootcamp sounds interesting to you and you want to travel in for it, the website is seed, S-E-E-D, So seed like you’re planting a seed, But otherwise, if you just want to find more information about me find my Twitter, find my LinkedIn all that stuff., so that’s my angel list profile,, and everything you could possibly need and want there and anybody can reach out to me. You can DM me, I respond to 100% of my Twitter DMs. So if I can help in any way or answer any questions, I’m happy to do so.

Jay Clouse 53:43
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 event and 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 54:23
Alright, Jay, so we just spoke with Casey from up in the Twin Cities. What did you think? Where do you want to start?

Jay Clouse 54:29
I want to start with how quickly we had a rapport with Casey, which I don’t think has anything to do with us and everything to do with Casey. Very quickly jumped in and we’re having fun before we even hit record on this show, which probably is just a another indication of how good Casey is at building relationships, building communities and connecting with people. So that struck me right off the bat. He told us nothing is off the table. Feel free to prod as much as we want and dig in anywhere we want. And we got pretty deep and pretty vulnerable with Casey’s past pretty quickly. So I appreciate that quality in somebody as well. What stuck out to you.

Eric Hornung 55:08
Yeah, I love interviews where you just feel like nothing’s off the table. And a lot of times you and I will ask questions that…I think Ezra Gholston one said that our interview is like being on a second or third date. So you and I can ask questions that maybe are a little bit probing to people who are used to being on a business podcast. And I love when you know that you’re going to get a real answer back, as opposed to sometimes we ask a question, and I guess we’ll kind of dance around it a bit more. Maybe not get into the real side of things, you know, the emotion, the feeling, the just kind of go to a pre canned type answer. I didn’t get that feeling at all from this interview.

Jay Clouse 55:44
Yeah, not at all. He really went in and leaned into his past and how he bounced around between companies because of his fear of success as he put it. He really does seem to be able to build things up quickly to a place of profitability and success to some degree and it’s great to see that Enterprise Rising is now entering their fourth year or fifth year. And all signals are that it’s going to be another successful event. I’ll tell you what really stuck out to me about this interview, or one of the most memorable moments of this interview was when he was talking about advising and talking with companies, and how he only wants to invest in companies where after the call, he feels like he can make five calls and massively move the needle for that founder, because, as he put it, he provides negative value for things he’s not good at because he’s taking away time and attention, which is just a different frame than I think you hear from most people. Some people say I’m not very helpful here. But in being not helpful, thinking of that as actually creating negative value because of the opportunity cost is a new frame that I really appreciate.

Eric Hornung 56:47
Probably the single question that sticks out the most to me in the interview was this idea that hey, maybe Minneapolis isn’t right for you, is a take he has, and I don’t think we hear that a lot. I think a lot of times you have these cities or community builders who are focusing on a few maybe verticals or areas. But if you’re in a different space, they try to be welcoming and say, Yeah, absolutely, you can build this here. And I think it’s kind of honest and refreshing to say, yeah, it’s going to be really hard to do that here. You probably should go do it somewhere else, at least at the beginning, and then come back. So that stuck out to me.

Jay Clouse 57:22
I feel myself leaning more towards that way, as well. You know, I firmly believe that it’s easier than ever to start a company from anywhere, in that you can start a company from everywhere. But that doesn’t mean that you should start a company anywhere, like there may be some advantages to being geographically located in certain places. And that doesn’t necessarily mean Silicon Valley. But if you’re in an enterprise SaaS company, maybe it’s Minneapolis as opposed to Tulsa, you know. I think it does make sense and I’m moving more and more that direction as well. And you see it when you talk to different leaders of communities, you know, they all say, well, we’re really strong in A, B, and C. And those A, B and C are different, wildly different, sometimes from state to state or city to city.

Eric Hornung 58:05
I think it really works across a lot of things as well. I think it’s why the boomerang movement is kind of taking off right now. There is a significant demand for someone who does a job in New York, that–I’m talking out of my experience in finance here–There’s a significant demand for someone who does a job in New York versus that same person who does the same job in pick any city in the middle of the country that is in a major finance hub. And a lot of that has to do with just the increased speed of learning. And I think you hear the same thing from the valley for engineers, like some of our friends who have come back to Ohio who had engineering jobs in Silicon Valley are much higher in demand and command, much different both salaries and equity kind of options than someone who just started a company here in the Midwest. And I think that and I don’t know where I’m kind of going with this as relates to Minneapolis, but I think that that’s just an overall trend that we’ve seen through Upside. Sometimes it’s better to go put your two ears in somewhere and then go wherever you want when you can command that premium, or when you’re in control of your own fate. So one other thing I’ve been thinking about lately is just how bullish I am on Minneapolis. And before we got on this, I didn’t really have a lot of reasons why. I just had felt kind of a vibe coming from Minneapolis and a lot of the numbers and deal flow and everything looks really good. I think Casey kind of reaffirmed that there is this community that’s moving there, and it’s moving in a positive direction.

Jay Clouse 59:29
Some of these things I hadn’t even heard of before, like the b2b sports tech, not an industry I thought about. He didn’t really speak much to the Target Retail accelerator, which we know our friends at Vibe and Upsy went through in Minneapolis. That didn’t actually come up, which makes me think even more, there’s more going on that there’s so much you leave some things out. A lot of communities but we talked to, you’re gonna hit all the major pillars of the entrepreneurial community in one conversation. Now, Casey’s going to launch a one day boot camp for angel investors, 92% of his sponsors at Enterprise Rising renew every year. Sounds like a good place to be.

Eric Hornung 1:00:04
It’s been a while since we’ve had a Minneapolis company on the podcast. So hopefully we’ll have some of those recommendations from Casey on soon.

Jay Clouse 1:00:13
And if you have any ideas for other guests, dear listener from Minneapolis or otherwise, I’m interested in this b2b sports tech, but anything that comes to mind, you can email us We’d love to hear from you or tweet Otherwise, we’ll talk to you next week.

Interview starts: 7:15
Debrief starts: 54:23

Casey Allen is the founder of Enterprise Rising, a Minneapolis-based conference specific to SaaS startup topics. 2020 will be Enterprise Rising’s fifth year, and they pride themselves on focusing on under-discussed or taboo topics related to founding a startup.

Casey himself has started five companies as well as a B2B SaaS accelerator and discusses his personal experience going from one to the next. This year, he will also be launching a boot camp called SeedMN for first-time angel investors with the hopes of teaching successful founders how to give back to the startup community.

We discuss:

  • AD: Finding experienced employees for your new business with Integrity Power Search (5:37)
  • Starting a conference and the first few years of failure (8:06)
  • Opening one of the first tech accelerators in Minneapolis (12:09)
  • Fundraising an accelerator in 2009 (15:09)
  • Building the reputation to launch an accelerator (20:27)
  • The struggle and mental obstacles behind founding five startups (22:13, 34:58)
  • Starting a company in the right community (27:14)
  • The Twin Cities’ DNA for enterprise SaaS (31:48)
  • The pattern of fear of success vs. fear of failure in startups (37:55)
  • Metrics for conference success (39:51)
  • Special markets in Minneapolis: b2b sports tech, enterprise health tech, and edtech (45:00)
  • SeedMN for first time angel investors (47:19)

Learn more about Casey:
Learn more about SeedMN:
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This episode is sponsored by Integrity Power Search, the #1 full stack high growth startup recruiting firm between the coasts. They partner with venture capitalists, private equity groups and CEOs to build amazing teams for the world’s most disrupting companies.

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