I’m Building an Early-Stage Fund with Al Doan and Bo Fishback (Rolling Fun #1)

 
Eric Jorgenson, Al Doan, Bo Fishback podcast recording
 

Very special episode today – with two of my favorite people talking about the early-stage venture fund we are launching together, a rolling fund called Rolling Fun.

My guests are Alan Doan and Bo Fishback. Both are founders, CEOs, angel investors, Harvard grads, and by bizarre coincidence both have climbed Kilimanjaro.

During our conversation, we share our backgrounds, interest in investing and hanging out with smart people building smart things, and how we came together to start Rolling Fun, which will be focused on early technology companies from all over the world.

To join Rolling Fun, you can read our fund letter here and click apply to co-invest with us!

Here’s what I learned from the episode:

  • "Climbing" Kilimanjaro is more like "Hiking Kilimanjaro".

  • Buying a town is a great way to build a brand.

  • Al’s model for e-commerce brands is to have content, commerce, and community.

  • One of the best outcomes of a company (even if it fails) is the success of those who worked together, learned, and went on to do other amazing things.

  • Investing is a great excuse to spend more time around interesting and smart people who are building amazing things.

  • It’s hard to find people who can deal with ambiguity... like startups.

  • Some of the best investments are based solely on faith in the founders, not specific ideas.

  • Starting a company with a big group of founders requires clear boundaries and responsibilities.

  • Individual investing is great, but it is limited; by coming together, we can make bigger bets in more companies.

  • Founding companies and investing is more fun together.

  • AngelList is a hell of a platform, and Bo actually helped provide funding to get them started.

Learn more about Al Doan and Bo Fishback:

Additional episodes if you enjoyed:

Episode Transcript:

Eric Jorgenson: Hello again, my friends and welcome to Jorgensen’s Soundbox. This show is a series of conversations where I learn from smart friends. And today is a very special episode because I'm with two of my favorite people, and we together are launching an early-stage venture fund. It's my pleasure to introduce you to my friends and partners, Al and Bo. Today, we're launching Rolling Fun, which will invest in early-stage technology companies all over the world. You can invest with us or perhaps if you're a founder, we will invest in your startup. Either way, we would love to talk with you. You can visit rolling.fun for more info. We're open for investments now, but we do have a two and a half million dollar a year cap for year one. So first come, first serve on the investor side. If you enjoy conversations like this and want to be a part of more, go to ejorgensen.com, check it out. We write about these startups. We share more things that we're investing in or interested in. Now, please enjoy this conversation arriving at your ears in three, two, one. 

Before we do anything even vaguely related to work, Al just climbed Kilimanjaro and has to tell us what it's like to climb a mountain. 

Alan Doan: Well, listen guys, as the second mountaineer in this group, because it was like the most grandiose thing I could think to ever do, and Bo was like, oh yeah, I did that when I was a kid. Like oh, okay. No, it was a delightful time. It was a delightful time. Use [Ruhollah] adventures. 

Eric Jorgenson: Oh, wow. Shout outs already.

Alan Doan: It was funny because I was talking to this guy about like what are the other trips that they do? They're like an adventuring company, and he's like, oh, you’ve got to go to Ethiopia. I was like, okay, what's going on in Ethiopia? He’s like, oh, well you climb up and you hike or you camp next to a live volcano. So, it's bubbling like 50 yards away. I was like, oh, that sounds awful. He's like, yeah, the sulfur smell, you can't sleep at all, but you get the experience. And then we've got a guy who will go out at midnight, and he'll drive you out in his truck. And he gets out, and he puts some meat on the end of a stick, and he sits out there and like does a call and hyenas come and will eat the meat on the stick. And he's like and then you can get out of the truck and you get like a child's pose and you hold meat in your hand and the hyenas will climb on your back and put their paws on you-

Bo Fishback: I’m a no, Al, on this as a future destination.

Alan Doan: …and eat the meat. And I'm like, huh, okay. He was like, oh, it's fantastic, you have to do it. It's the best one. I was do you have any with like a beach? Do you have any adventures that are like, oh, that looks really cool, not that I slept next to a volcano that could have bubbled wrong and killed me and fed a hyena out of my hand while laying prone on the ground. No, we don't have anything else. No, it's funny because all their stuff- like this great infomercial for these guys, but I was like, what about Petra? And he's like, yeah, yeah, yeah, most people they'll go to the front of Petra. We take you on a five-day journey in the back. We pretend to be like Ottomans in a caravan and we’ll attack you and do the whole thing, and you eat like they did. And then you come in through the back of Petra, which nobody's really allowed to do. And like that's- I feel like if you just take the Statute of Liberty, sure, but we throw you off the boat and you have to swim there, and we have a cheese sandwich for you when you make it through it. You really get the experience. That's like, man, that sounds awesome. 

Bo Fishback: So actually, Eric, you're the only one of this group that hasn't climbed Kilimanjaro. I don't know if that's lost on you, but that’s a tough spot to be. 

Alan Doan: What aren’t you doing on Africa's tallest speak? 

Eric Jorgenson: I have no plans for Kilimanjaro, but I have a lot of time left because I'm the youngest, which makes me feel slightly better about the fact that I am the only person at this table who has not founded a company, climbed Kilimanjaro, and fucking gone to Harvard. So, it is unclear what I'm doing here.

Bo Fishback: Now that I'm thinking about it, do we need Eric? That’s one question about this fund in general.

Alan Doan:  He hasn’t done anything.

Bo Fishback: This may be a two man fund going forward.  

Alan Doan: He is 21 years old. 

Eric Jorgenson: 90 seconds before we started recording, I believe it's not a misquote to say, thank God you brought notes. We need somebody who brings notes.

Alan Doan: Listen, just to stroke your ego a little bit, you're really good at notes. 

Eric Jorgenson: Thank you. I only need to be good at one thing.

Alan Doan: The only downside to not having Eric would be that this fund could never have happened because neither you nor I would have done it.

Bo Fishback: That's correct. He also maybe the most famous one in the room, to be honest, I don't know. He’s done an excellent job brand building despite not climbing Kilimanjaro, pretty amazing. 

Eric Jorgenson: You guys have been trying to get famous by climbing mountains, and it's just not the way to go about it.

Alan Doan: The best I was up there with three people who were seven peak summiteers and they'd done all of them. So, you're like, man, this is so hard. And they're like, oh, I remember one time when I was on Denali and like stuck and we thought we were going to die, hit by snowstorm, and it's like, oh, okay.  

Bo Fishback: That sounds much harder. 

Alan Doan: I'm going to have my porter hike up my backpack. And do you have anybody that could warm my gloves? I just want you to blow on them a little.  

Eric Jorgenson: What is the risk of death on Kilimanjaro? 

Alan Doan: It's as close to zero as possible. It's funny because going, if I were to go again, they make you get like global rescue insurance and stuff. And so, you're reading up about it, and it's like, oh if they’ve got to evacuate me off of there, if I sprain my leg and they got to take me in a helicopter, and then you get there and it's like, oh, it's just a path. It's a path that you walk. I mean, it's a path up. You're going up, but there's no technical anything to it. So yeah, I would've been- I would've packed much less and brought a board game to play would be one of the things I would change.

Eric Jorgenson: A deck of cards.

 Alan Doan: Taco hat, pizza, cat, goat, whatever.

Eric Jorgenson: All right. I feel like we've sufficiently rambled to the point where we should introduce ourselves.  

Alan Doan: That was good banter, guys. That was good banter.

Bo Fishback: I think we should stop. I think this fund is fully subscribed at this point.

Alan Doan: If you're not in by now, I don't know what to tell you. 

Eric Jorgenson: 66% of them climbed a mountain, oh man.  

Alan Doan: And that mountain was our education at Harvard.

Eric Jorgenson: Al, do you want to like tell your story, your introduction, what’s your like people who don’t know you story? 

Alan Doan: Sure, sure, sure. I am but a poor farm boy. That's true. Well, so I actually was born and raised in California. My family went bankrupt when we were wee lads, I was like 13 and Sears came to take away our Packard Bell computers, very jarring for me as a child. But then we moved our whole family out. Like we were fifth generation Californians, moved out to a farm in Missouri that literally my mom found as we were like driving around old gravel roads and she's like, oh, here's a place that nobody lives in. For like 40 years, it was like- the doors were wide open, it was waste deep in garbage. Kids looting everywhere. She got the guy, she's like we can't afford rent, but if you'll let us live here, we'll clean it up in exchange for rent. And he said sure. So, that was our- When we came to Missouri, I literally, I was like we're moving to the wild west. Like I was ready to go to the middle of nowhere here. 

Eric Jorgenson: Not a lot of west to east adventure stories. 

Alan Doan: That’s a good point. Let's go to the wild in the east. But there was no running water. I pooped in a bucket for like months, and we were literally like Little House on the Prairie. We'd boil water on the stove. It's funny, I'm glad they didn't have- when we were kids, they didn't have a child protective services or my sweet mother wouldn’t have us anymore. 

Eric Jorgenson: How old were you? 

Alan Doan: I was 13 when we got here. And it was funny because like California was the land of concrete and strip malls because I lived in like the poor part of California. And then we moved out here and it was like lakes and rivers and streams. For a kid, I was Huckleberry Finn all of a sudden and just like loving life. I had a great time out here. And then, I grew up, went to school in Hawaii. I started in St. Jo, Missouri, if you know Missouri, Missouri Western State College now University. And I was like, wait, I'm going to college? I should not go to St. Jo’s, so I went to Hawaii. I had a good time there, came out and I really wanted to get into startups. I thought that that was going to be my thing. And so, I slummed around with Techstars out in Boulder. I talked old Nicole Glaros and David Cohen into giving me a shot as like a mopey intern out there. And it was great because I got to just hang out with a bunch of cool people building cool stuff. You'd sit in with these like mentor interviews where they're like chit chatting with Dick Costolo and stuff. I'm like, oh, I always wondered about that, great. And on the side, I started this company for my mom, a quilt company called the Missouri Star Quilt Company in our little town of Hamilton about an hour north of Kansas City. And so, I kept hopping around with Techstars, went out to New York and helped Dave Tisch start the program out there and like had a good time with it. Just really built a cool network. And then went and did Startup Bootcamp in Europe with Alex Farcet and just had a blast. Like I was deep in it, spent a couple of years there, and then this quilt company that I started on the side kept growing and that was doing its thing. And so, that's like a hundred million dollars in revenue. It's a great big company with hundreds of employees now, but that kept growing. And I think I started when I was 26 and got all the growing pains. Like we bootstrapped the whole thing, which was cool, because nobody would invest in a quilt company nor should they have. They were wrong but also right. And so, we built this quilt company. But our schtick, man, like we bought the whole town. So, we own 27 buildings in this town because I wanted- like literally sitting through these mentor meetings and stuff, and like all the ideas were going towards the quilt shop. They thought they were giving advice to cool like video internet companies. But no, really I was in the back saying yes-

Eric Jorgenson: Sell more fabric. 

Alan Doan: And so yeah, I Googled what town had the most quilt shops of any town in the world, and it was someplace in Germany had four. I was like, man, we're going to murder these ladies. And we have like 15 quilt shops in our town. We turned it into like the Quilt Town, USA. It was this whole big to-do. It's cool. If you ever get the chance to come see it, you should. But we have a hotel thing that we work out of there, we have restaurants that we had to start and do all this stuff because we had to build the whole Disneyland experience for delighting 40 to 70 women was sort of our MO. 

Eric Jorgenson: And my fiancé who loves Hamilton, and we go up there all the time, and it's super cool.

Alan Doan: During the pandemic, Eric called in a favor. He wanted to give his wife a private shopping tour. So, we opened up these stores that had been closed for like a year and it was a good boyfriend move. Then I stepped back from that. I would call it like a divergence of risk tolerance happened between me and my sister and my buddy Dave. We were the co-founders, and when we start a company, we started a quilt company together and it's like, yeah, man- this is turning into much more than two minutes, I'm sorry, we can cut it down. But if we start a quilt company together, we'd be like, all right, let's do it. You like quilting, I like quilting, this is awesome. Then you add $10 million to it, and then you add $50 million to it. And all of a sudden, you're like, wait, you're not working as hard as I am. Wait, wait, wait, I think we should grow this to be way bigger, and all of a sudden, it's 50 million. You're like, no, we should make sure that we can always pay our rent. Like this is how we should optimize. And so, we had very differing views of how to grow the company at that point and went through the whole process of like, oh, well, what does that mean? And what should we do? And how do we handle that? And then started a very long process of turning a family business into a business started by a family, which is no easy task, but yeah, got through that. And then I sat for a little while and you sort of have the ego voice in your head that's like, nobody thinks you were good. You were just a quilt company. You've got to do more. And so, I went and started another company called Let's Make Art. I was shopping for watercolor paint for my wife because I stepped back from the company and like saw color for the first time and light comes back in your life. And I find my wife on a river. We were river rafting in Wyoming. And I came up out of the water shimmering, and there she was, and just water cascading through my hairy chest. She was in another boat. And I said you woman, come to me.  

Bo Fishback: I like that when I heard that at first, I thought she was shimmering, and then I realized that it was you that was shimmering. 

Alan Doan: In my fantasy, it's me shimmering out of the water. And she's just in the boat. There I was, the sunlight glistening off of my body. 

Eric Jorgenson: Icicles in his beard and paddle over his shoulder.

Alan Doan: So, I get married-  

Bo Fishback: Immediately, they get married immediately. He bonked her on the head and they got married. It was just like that.

Alan Doan: Poor woman didn't know what hit her. And no, it was a little bit like Seven Brides for Seven Brothers, and I'm like, look, I'll marry you, but I've got this town that I have back in Missouri. She's from Utah. She's living in Utah at the time. I'm like I've got this town. It's kind of a weird thing. You are not going to believe this. She's like, oh, okay, it'll be fine, it'll be fine. And then I take her to a 1000-person town, and she was like, so where should I get a job? And I was like, well, we have a Dollar General or a Subway. You can't work for the quilt company. That would just be weird. 

Eric Jorgenson: And there's no other employer- that’s like a 1500 person town and like 800 people work for Missouri Star.  

Alan Doan: I’m glad we're seeing therapists at the time because I had a lot to work through still, turns out. And so, I start this- I'm Googling watercolor paints, and the number one seller of watercolor paints is dickblick.com. I was like, man, what if they didn't call themselves Dick Blick? Where could they go? And it was like nine clicks to get from the homepage to the product that I was looking for, and they asked a bunch of crappy questions I didn't know the answer to. I was like, man, people, good creative people are going to be sucking at this. And so, we started another company, that Let’s Make Art. That went zero to 16 million in the second year. It was a great success that just was really cool. But my wife was very sweet. She's like you're a builder and you just keep building yourself the same dumb box, just shipping stuff on the internet. And so, then I sold that to Creativity, Inc, which is my company. It was an easy sell. I sold it to myself. And then, I started another one called Pretzel, which is what I'm working on now. And that is sort of a Google photos for everything you own. We pull everything in under one roof and organize it and help you know what you're doing with your money. It's pretty cool.

Eric Jorgenson: It is cool. Is it downloadable or is it still in the test flight?

Alan Doan: We're in the app store as of two weeks ago. We're just moving mountains over here. 

Eric Jorgenson: I’ve been playing with the test flight for a little while, It's very cool.

Alan Doan: Check it out, man. It's stable now, which is nice. The connections are stable. So, you can download it and it'll still be there. 

Eric Jorgenson: If you loved it when it was unstable. 

Alan Doan: That's what everybody says. So, I'm married. I've got a beautiful wife, three boys. I got twin one-year-old boys and a three-year-old boy, and we live on a 250 acre farm in the middle of nowhere. They can run and play in the forest and it's great.

Eric Jorgenson: Farm to farm. 

Alan Doan: Farm to farm. I'm delivering children from the farm to the farm fresh. 

Eric Jorgenson: That’s the beautiful circle of life. Will you do like another minute or five on the quilt company itself? Because I feel like it's kind of an amazing- you like it's a quilt company and now we own a town and the transition of like, hey mom, I'm going to put you on YouTube to, oh my God, we actually run an e-commerce giant and sell more fabric than anybody else in the world is like kind of an interesting story in itself. 

Alan Doan: I'll give you a little more on that. So, the idea happened, like I was going to school in Hawaii and I fell in love with these daily deal sites, woot.com, Steep and Cheap, and I don't know if you remember, there's a daily deal site for everything. It’s like are you into mountain biking? Chainlove.com. And like everybody had one and I was buying like weird random stuff where I'd buy like- I bought a feather comforter and had it shipped to mom's house. And she's like you go to school in Hawaii, you don't even have windows. What are you doing? I was like it was such a good deal. Here's three cast iron skillets. I got 'em for $6. I don't need a cast iron skillet.

Bo Fishback: I remember buying the Woot bag of unnamed things. And it's like we're not going to tell you what's in it, but buy this bag, and it’s a good deal, and then you get a bag and you open it. And I was like I cannot believe that is a business. And then I cannot believe that Amazon paid a very high premium for that business. It’s amazing.

Alan Doan: What's the best is Matt, I forget his last name, but like the guy, they put the band back together and went and started meh.com because they were pissed at how Amazon treated Woot. But what was cool about it though is I was like, man, this totally hooks me. Nobody's building this for like my mom. Like nobody, nobody cared about- And they still really don't. I mean, you look at like they're a huge consumer of, I don't know, the amount of television on there, but everything's like Welcome to Travel with Mario Lopez, we’re going to Miami! And you're like, my grandma's the one that's watching this; you really should go to Hannibal, Missouri, and talk to us about the river boats. That's what they’d love to see, but nobody builds content for them. So, I started quiltersdailydeal.com. And I literally, man, I was writing, I was copying Woot exactly. I was writing a big story and the whole thing. Like you look back at the early ones when I was doing it, I’d be like, and then Pinocchio went to the crazy carnival and turned into a donkey and looked up and said, jumbo rick rack, $3.33 cents, you should get your stuff today. Like we’d just go all over the place with this stuff to make this company happen. And so, we started this in the middle of nowhere, just trying to help mom not have to live in our basement, help her pay the bills a little bit. And it started to do a thing. And it was a marketing challenge because we were like, man, how do we advertise to quilters? There's not an ESPN for quilting. What should we do? So, we started building. Our strategy at the time, we just called it like watering holes. We had to build like watering holes where people would gather. And if we did it with different brands, then people wouldn't be mad to hear from the same- like Missouri Star can't talk to you 10 times a day, but if you have Quilts by Me and the Cutting Table Blog and like all these different people can sort of nudge you throughout the week and it's not seen as overwhelming or spammy. And so, we built a lot of this. And then, at the time, this was 2008, we launched our YouTube channel, which it's crazy, YouTube was only two years old at that point. YouTube started in 2006, which is, huh, because they really did a good job. And for some reason I knew them in 2008 and it was obvious they were a winner. But they were just everywhere. And so, we started- the only YouTube channels for quilting were like I'm quilting buck, and it'd be like an old 6 40 by 480 webcam that this guy was trying to do a thing, which is great. It's cool that he was doing stuff. But I was like, man, we'll buy a decent camera and we'll teach people how to do this stuff. We'll give the content away for free. And so, my model for all my e-commerce brands is content, commerce, community. And I have an angle on each of those that we answer, batting a thousand when I follow it. And so, we started with the content there, and it really- I mean, the video stuff was the thing that was our mainstay because we would send out an email every week to people and say here's this new video that we're giving you for free, and by the way, some stuff that you need to make the thing in the video is here. And we'd get like- man, in the early days, we'd get like a 70% open rate on that marketing email going to hundreds of thousands of people, which if you're a marketer, you're very happy with a 70% open rate. And so, it just grew like crazy. And yeah, I mean, the town, that physical manifestation of the brand, became really important because everybody else was a warehouse on the internet, and we got to be like this sort of personality that you'd come visit. You can come see us, come give us a hug and tell us how things went and what you think about stuff. And everybody else was just a warehouse trying to take your money. It's funny because like I work with brands, and literally, I don't think there's a company I've invested in that there's not a part of me that's like you should really buy a town. 

Eric Jorgenson: Do you know how cheap towns are? There are a lot of towns for sale. 

Alan Doan: I invested in Lamba School that's Bloom Tech now with Austin Allred and they're doing great, but I was talking to him, I was like, dude, did you know you can buy a summer camp for like a million dollars and you can get like on a lake in Maine with 250 cabins? Like go buy a summer camp and have people go there and you can like have the whole thing. What's cool about it is like that's worth telling a story. I mean, a PR person's dream is like, oh, you're interesting, thank you. I mean the quilt company, that's been on the front page of the Wall Street Journal, on CBS Sunday Morning, NBC Nightly News. Like we've been everywhere with that. And I thought the family was an interesting angle. The industry was an interesting angle. I thought I was interesting and shimmery. And the reality is all they cared about was the town. The town has been the most interesting thing by far of – what the town's done, that's like 4% of our revenue, but still, it just means so much to the story and to who we are and to our customers.

Eric Jorgenson: And you like revitalized this town. Like I've been to a lot of small towns and like the atmosphere is amazing.

Alan Doan: It sounds great. Honestly, like it's just getting bigger. We just bought this shoe factory in town, which is four acres in a 40,000 square foot building and our own water tower, which a man needs a water tower.

Eric Jorgenson: You can shimmer constantly under that water-

Bo Fishback: Just Al on the top of the water tower shimmering for all. 

Eric Jorgenson: For your birthday, we're going to put a giant beard on that water tower and make it look like Al.

Alan Doan: You’d think you'd want to climb right up that, but it is terrifying when you get looking at it. But yeah, we'll keep building on that stuff. And, I mean, we got a hundred thousand people a year that come through there, which for a town that like nobody really knows about, like it's just in the middle of nowhere, it's an agriculture town. And the fact they get to come and have a beautiful experience and like houses are getting built and schools are getting some revenue and all that stuff, it's fun. 

Bo Fishback: It's really cool. That is really cool.

Alan Doan: That's my quilting story. 

Eric Jorgenson: We'll proceed alphabetically. 

Alan Doan: How are you Bowman? Tell us about your quilting story. What's your relation to this? 

Bo Fishback: My relationship to quilting will be a very short story. So, I think we'll tighten this thing up going forward. No, just listening to that, I think I grew up in a probably slightly less PTSD inducing Huck Finn situation, frankly. I grew up in rural Georgia on a big lake with not a lot of people around. And my first job was working at a marina where I rode my jet ski to work every day, which was like the most fun thing in the world. My dad had started a company when I was a little kid out of our garage and kind of got to watch him grow it. He sold it my senior year in high school and retired I would say probably prematurely given that his plan for post-retirement was not a very good one. 

Alan Doan: Now he’s just desperately trying to get a thing- 

Bo Fishback: Well, he spent the next year thinking he was waiting for a non-compete to run out, and then instead, just actually didn't know what he wanted to do next. And he was in his early forties. He's actually about the same age I am now. And had a hard time picking it back up to get into something. And I kind of always thought, watching that growing up that like I like that company building thing, that seems like a good idea. But I'll never want to retire. Like I want to keep working and building something else and helping people build things. And I think my brother and I were both just like pretty programmed to think like if you could build something useful and valuable, you could kind of make a living doing that. And so, I've started and sold a handful of companies now, which I mean, we can run through or whatever, but mostly I love early-stage companies because it's when you get to see people be the most creative and do insane things like buy towns and actually pull it off. And I think it's when you get people's kind of full self working on things and you just see the best of kind of what is possible. So, I had a social networking company in 2004. I learned only in hindsight that I was one of the first 10,000 users of Facebook, which is pretty crazy for a platform that has billions of people on it now. 

Alan Doan: What was your social network? 

Bo Fishback: It was called [Jao Nai], but we did not launch it in the US. No, it was actually, we launched basically the same product slightly localized in France, Germany, Brazil, and China. Nobody in France gave a shit. Actually, nobody really gave a shit in Germany either. In Brazil, it was actually right when Orkut was coming up and it steamrolled us. And in China, we had somebody on the ground there who was just a real bad-ass and it was a kind of platform that we had built to be localized with the thought being we're going to start all these local social networks all over the place. Only the one in China worked, and 10 months after we started it, somebody bought it. And actually, essentially like a subsidiary of a sovereign wealth fund bought us and the five other fastest growing kind of social networks in China and rolled them all up and basically turned into China's Facebook today. And so, we thought they were massively overpaying. We're growing really fast every week. We sold it 10 months after we started it. It was just me and another guy. And I was like 25, and it was a really cool and hilarious experience that I think was 97% luck, but also a really fun and cool experience. And so, on the heels of that, went to business school at Harvard. And I literally went there thinking that like this seems like it would be a fun place to go meet other people who want to start companies. It wasn't really that actually I kind of learned when I got there. It was a different thing than that. It was fun. I had a great time. I actually ended up meeting a couple of guys at MIT at the time who one was in their postdoc and one was finishing their PhD who'd invented some really cool technology that had been funded $40 million from DARPA money to do some cool laser stuff. And we licensed it. We licensed their technology from MIT, started that company, moved out to Palo Alto, raise some money. It was called LightSpeed Genomics, and it was a human genome sequencing company which was a very hard company to build in the time when everybody's kind of racing for the thousand dollar genome. And we had a really cool solution in the kind of optic space. Spent about five years working on that. We got bought by a large Korean company that is like the largest sequencing service provider in the world. And they were trying to do proprietary technology. 

Alan Doan: Do you guys remember that folding at home craze? Like were you a part of any of that? 

Bo Fishback: No, no, no. 

Eric Jorgenson: I learned about that at the startup weekend where I met Bo, all the distributed computing stuff, which was super cool.

Alan Doan: We had in the early days, there was a website out here called KC Geek that was just a couple of buddies and stuff, but we'd spend our weekends going into like Comp USA and installing our client on every computer.

Eric Jorgenson: You should have tried that for bitcoin mining. 

Bo Fishback: I was going to say, there's a new version of that in the web3 world actually, where it's like, hey, I'll pay you 50 bucks a month if you just plug this little thing in your house for me. It's like also I might steal all your credentials. But I do, I think that is actually like the web3 world is kind of introducing a whole nother version of that, which is pretty wild. So, in any case, that was a company that was honestly a grind. It was like a serious grind.

Alan Doan: You were excited to be out?

Bo Fishback: It was interesting. I probably learned more about founding team dynamics in that company than anything else that I've ever done. It was me and two co-founders who ended up not really being aligned with what we- two of us were kind of very dialed in and the other one was kind of always pulling in a direction that just made it really, really hard to build what we thought the company could have been. And eventually, frankly, we pretty much- I mean, the sale was roughly us capitulating that we were not going to turn it into a billion dollar company, but it could be a tens of millions of dollar company and we could kind of get out and move on, but it's actually one of those things that made me think really hard about founding teams and how to help them work together and how to not get in your own way and how to navigate that stuff. And anyway, learned a lot, also learned that I probably didn't super love really capital intensive hardware businesses, even though they seem really fun. So, we had this cool thing that we had with that company. We had a really neat lab in Palo Alto, and it was like a very Tony Stark experience where you like walked on, it flipped on some switches and they were green lasers that filled the room and reflected, and you just like momentarily felt like very powerful and then like it didn't really work, which made you rethink how powerful you were. But we built some really, really neat technology actually. And that was kind of a fun thing that came out of that. And then I actually ended up spending- I was kind of doing some angel investing at the time. This was 2007 maybe. I was doing some angel investing and learning that like that was not the thing that I love to do full time. So, I ended up starting kind of what started as like an entrepreneur residence at the Kauffman Foundation, which is a big foundation in Kansas City that helps entrepreneurs and spent about five years there as the kind of head of entrepreneurship, and we kind of spun up a little in-house incubator that actually specialized in taking post-doc students from stem labs basically at universities and helping them commercialize what they'd invented. And it was really fun. Like we had 10 to 15 PhD founders kind of coming through these programs and kind of helping to figure out how much was kind of science and how much it was business and how to commercialize it and license it. And so, you just got to see a really, really rapid flow of these things. And some of them actually turned out to be really, really awesome companies that like, in hindsight, I wish I would have just been an angel in all of them- running a program. But they've done some really, really cool stuff in the kind of MedTech world and the surgery world and the kind of biomolecular world. So, we just kind of got to learn a lot fast. And what I kind of realized, I think, kind of five years in I just wasn't done building stuff. Like philanthropy full-time was not the thing that was probably the thing that I was ready for. That's funny in this context of a podcast talking about rolling funds and stuff is like also investing was not the thing that I wanted to do full-time. Like that was not- like I like to build and I like to be with people who are building. And that is actually kind of when Eric came into my life. So, Eric was coming to be-

Alan Doan: He just came of the water shimmering.

Bo Fishback: He was in a Kaufman Foundation pond shimmering like a giant merman. And no, I was actually hiring interns to come and work in this kind of accelerator incubator thing at Kauffman and actually met Eric at Michigan State when I went up there because I just wanted to kind of meet some folks who were working on startups up there. We kind of hit it off and I was like, hey man, you should totally come and spend the summer with me. It'd be really fun, you’d work with a lot of smart people, you'll learn a ton or whatever. And so, he was coming for a visit sometime in the spring to kind of get ready for his internship. And the day he showed up was the day that I told the Kauffman Foundation that I was leaving to go and start a company. And I was like, hey, welcome to your internship. You can have an internship, but I won't be here. And he was like, what are we doing here? And I was like, well, if you want to come with me, I'm going to go start this company and we're going to give this thing a big run. And that was kind of the moments leading up to starting Zaarly which was a company that we had for about 10 years, actually sold it last year in what was roughly like a disaster on some fronts and a hilarious and fun adventure in some other ways. But we did the very classic like blue chip venture backed, Meg Whitman on the board, Kleiner Perkins led the round, raised a ton of money, spent all the money, hired lots of people, fired all the people, the really kind of unadulterated pursuit of scale, where if you don't really scale, then you don't have a company. Like the- and I mean, I went into it knowing that was what I wanted to try because I'd never done something like that. Probably won't do that again. But I learned a ton, met a lot of amazing people. Honestly, one of the coolest things I think about Zaarly is that it goes beyond Eric that like people who were a part of the adventure early on and in the mid part and even more recently have really gone on to do a lot of amazing things. And some of them run their own companies. Some of them run their own funds.

Alan Doan: You are saying you’ve got a Zaarly mafia. 

Bo Fishback: Yeah. Definitely yes, actually like there's a- 

Eric Jorgenson: It’s not in a lot of Twitter bios but it’s underground.

Bo Fishback: It's been like really cool to see the group of people who kind of all were kind of forged in that like go-go fire.

Alan Doan: I feel like that's a dream. That's every entrepreneur like just dreams of having the crew that then springboards out.  

Bo Fishback: I agree with you. That was not the anticipated outcome that I was going for. But it actually has ended up being the one that is probably like- that on the one hand, I'm probably like most proud of, and it is also probably the most productive. Like Eric spends a lot of time talking about leverage. If you just think about making a positive impact on the world leverage, like the group of people who kind of came through that, even, I mean, investors, team members, consultants, like everybody who kind of was a part of that has just gone on to just do awesome things. And I think all of them are like, well, damn, we learned some things not to do in that context. And also, we learned how important and valuable it is to work with people who you're excited to work with. And that is like a really, really cool thing to see. So, in any case, we sold Zaarly last year to an Australian company that is a hilarious owner story that I will not spend tons of time on, but a company called Airtasker that just recently launched in the US kind of on the back of acquiring Zaarly. It's real wild because like they are virtually an identical twin of the original birth of Zaarly in 2011. They started that same company in 2012 in Australia. And they went public last year. And in some ways, they kind of made this thing work that we tried to make work. 

Alan Doan: What was the idea for Zaarly?

Bo Fishback: The original context of Zaarly was kind of in an environment where everybody has a connection to the internet with them at all times, you can basically kind of take the want ads and say like, hey, I am in the West Bottoms in Kansas City and I need somebody who can help me with this. And you can syndicate that out to everybody in the kind of the local proximity network and have people say like, oh yeah, I'm happy, I want to go make some money right now. I want to go make 20 bucks. I want to go make 200 bucks. It was to bring kind of like a transparency to like local economies so that people who needed things and people who wanted to make money could find each other. And we built that and it was crazy because like it's easy when you run the PR engine and stuff to get like a lot of hype and have, I mean, we had a million people sign up and all that kind of stuff, we just never actually converted into a good business. It ended up pivoting a few years in to kind of turn into a different business. But as it relates to Airtasker, that is exactly what Airtasker is today. Like it is literally 70% of people in the country of Australia have unprompted brand recognition with this company where you literally go to their website and you say, hey, I need somebody who can come over tomorrow night and clean after a party, and within two hours you have seven offers from people who are like, hey, I'll come and do it, I'll do it for less money than that other person or whatever. And it is like a thriving marketplace. And so, they're trying to figure out if they can export that from Australia. We'll see. The team that was at Zaarly during acquisition is kind of working on it with them and stuff and kind of helping them try to figure out how to find the right footing there. But it's pretty wild. I mean, it was pretty- and one of the reasons that we went ahead and did this acquisition, because it wasn't like overly material financially, was like, damn, they made that thing work that we tried to make work 10 years ago. What's the magic there? I still don't know the answer. But trying to figure it out. 

Alan Doan: It’s just cheap Australians, that's what you needed.

Bo Fishback: Yeah. I don't know. I think also 10 years ago it was a pretty different time in the internet, like the way that consumer internet has changed is really different. Anyway, all along the way, starting in 2004 probably, I started doing a couple few handful of angel investments a year. Ended up being a lot of angel investments kind of just over time because that's what happens when you do them here and there. And some of them have exited, some have gone to zero. I generally try to invest in companies who I found myself helping not as an investor because I just like to be around the people. And then when it made sense and rounds came together, if that's what they needed, invested. But it was really for me, like a lever to spend more time around people who I like to spend time around. And I had actually never really done anything that was like pure arm’s length investing until much more recently, like directly in companies, because the whole point of it for me was to like meet awesome people who were doing cool things and see if I can be helpful and if not, then get out of their way. 

Alan Doan: It’s an excuse to go bum around the office and get a lunch. 

Bo Fishback: It's an excuse to like hang out with people when they're their most dialed in and the smartest about the thing that they're working on. And I think it's just really- honestly what I think is it’s like great retirement prevention. It's like you don't ever want to retire if you are around that kind of energy. And that's what's fun about it I think for me. 

Eric Jorgenson: Yeah, you get a super broad view. And the thing that you realize is like when you are a founder and when you are in founder mode, you spend all your time with your team, and in investment mode you get to spend time with other founders and hang out and kind of be like, holy shit, you know a lot about quilting. Tell me everything. What's it like to buy a town? Like those stories and learning all that stuff is all really cool. And when you are friends with a bunch of founders you kind of see those seeds as they're planted and emerging. 

Bo Fishback: It is interesting, like that is the thing where like when you think about like an investment that you and I did together, like a Density, where it's like I'd have done whatever to help Andrew as he was getting that company started. Like he flew out to Kansas City and like hung out for a couple of days or whatever. And that was from my perspective, not at all in the context of like, oh, let me get into this angel deal. It was like, oh my God, you just want to help this guy be successful. And it's so turns out that at this moment, they need to raise a round and there's an opportunity to participate in it. And so, that is kind of like the thread to pull when you meet so many founders who are smart and looking for help. Sometimes the answer is like you can write a check and that's the help that they need. And sometimes they just need to meet the right people or whatever it is. But that is like just a great example of like, if he’d have been like, no, I don't want your money, I would have been very, very happy to spend time and energy helping still because it's just the people you want to back. 

Eric Jorgenson: Yeah. And that was a unique one. I mean, like just seeing- I never even heard anybody talk about that problem before. And so, like not only are you learning something about- 

Alan Doan: What is the problem? 

Eric Jorgenson: So, Density builds this sensor that is like a computer vision sensor you mount over a door and it can anonymously count in real time people like coming and going from a space. And so, then you're like- 

Bo Fishback: It’s a people count. They have them in gas stations, but not the Density version because the thing just dings so you know someone's there. It turns out like nobody had messed with that technology in 50 years, 40 years or whatever. And they were like, hey, if you really did this right, you can know how people are using space.

Alan Doan: Every retailer has some version that's trying to count how many people came in and then what’d they convert on. 

Eric Jorgenson: So, the retailers all use these like cameras because it's a public space, so you can use a camera and then sort of count or identify from there. But a lot- like internal companies all need anonymity and airports need anonymity. Like there's a bunch of stuff that it can’t be individually recognizable. 

Alan Doan: You need to know how many people are in there so when the fire happens-

Eric Jorgenson: So, there's insurance compliance. There's, I mean, like every time you see somebody standing at a door with a people count clicker or whatever, yeah, there's all kinds of cool applications of it. 

Alan Doan: It’s a pen. 

Eric Jorgenson: They are jamming as many people as they can into that fire- 

Alan Doan: What about you, Eric? Let's hear the story, man. 

Eric Jorgenson: I should not have let you guys go first. 

Bo Fishback: Postproduction, you can go first.

Eric Jorgenson: No, I grew up just outside Detroit in a like also a family- a business family. Like my grandfather started a business that my dad ran, so it was very normal to kind of like sit around the table and talk about like, oh shit, we have to make payroll. And it was a small business more than tech entrepreneurship. It's kind of like a manufacturer's representative. But I came up with that appreciation. And so, I was always the kid like selling candy out of my locker and getting paid to give kids rides to school and stuff. And by college, that was kind of becoming tech entrepreneurship because Facebook was getting big and like WordPress was coming out and it's like, oh, this is like a global thing. And like true scaled entrepreneurship that kind of changes the world is a little bit distinct from small business and it's tech enabled. And so that was kind of like what drew me towards Silicon Valley. And I started working on, I mean, I met every other student I could at Michigan State that was like starting a company. And then that led to starting a student business incubator. And so, I was like running a little baby student business incubator when I encountered Bo at Kauffman, and was like, oh, this is like the world-class version of what I'm doing. I mean, Alan, the same way that you were like I just want to hang out at Techstars, I was kind of like, holy shit, they have done all the work to collect the smartest people in the world about all of these things. And I can watch this laboratory for companies starting and learn everything. And Bo fucked that plan immediately by just like going and starting his own company. But that was like, I mean, my goal eventually was like, I will work in this place, I will watch all these things. I'll kind of like learn these patterns. And then, it's the perfect place to kind of join one of these companies. And that just happened in a day instead of three years. And I was along the whole Zaarly ride doing a bunch of jobs, like whatever I could that I was vaguely qualified or partially qualified or completely unqualified for. 

Alan Doan: That's why you're in a startup. I’m a CTO.

Bo Fishback: Yeah, I think, I will say that was probably true of Eric. It was true of some other folks too, it was definitely true of Eric that any time we encountered a problem where we weren't sure where to start, we gave it to Eric. And he had the rapid acceleration version of how do I get my bearings? How do I get smart enough about this to be useful? And then either how do I turn it into a process to give it away or say we should never do this again. And those are equally good answers, frankly. 

Alan Doan: Honestly, man, because I was one of those people as well, in my head, everybody is that person. And it turns out that skillset is so frigging rare to track down. Like if you wanted to go and hire that person tomorrow, which all of us probably would, there's very few of those coming out of business school or anywhere that you would actually say, oh yeah, great, you're my guy. 

Eric Jorgenson: Nobody really knows what to call it, but every startup usually has one. 

Alan Doan: Yeah, just the place that problems go to die. 

Eric Jorgenson: Miscellaneous fixer. Jeanine calls it, she's like I'm Junk Drawer Jeanine. I'll just like pick up whatever project there is and handle miscellaneous shit. 

Alan Doan: And it is twofold. One, you let yourself be terribly abused because you'll take everybody's crap and like fix it. And you're the one that stays up till three in the morning to make sure the company doesn't die, not the people dropping the ball. But on the other side, you gain a lot of skills and you become very valuable to the company. 

Bo Fishback: Yeah. I think that's one of those, what happens I think so much in startups and a thing that I have a lot of appreciation for now is that so much of the battle is just finding people who can productively deal with ambiguity, because it is ambiguous, ambiguous, ambiguous until there is clarity, and like not everybody is programmed to thrive in those environments, but like every great startup that I have seen is one of two kinds: Either happy to fight the ambiguity until you get to the other end or is so razor clear about the problem and the solution out of the gate that like they never have to deal with that ambiguity. And actually, those two types of startups just need very, very different people inside of them. 

Alan Doan: Well, it's funny. Cause yeah, I feel like in a medical device company, you're going to be much more laser-focused on like- building a social network, you're like we don't know what it's going to be or how we're going to make money yet, but we're confident. 

Bo Fishback: We will discover our way there. And that is its own kind of like super-duper valuable skillset. So anyway, that's a perfect- those, I know this thing and this orthopedic case is broken, I can fix it is very- but it's also why it's really, really hard to build multi-billion-dollar companies in that space because those are solutions to a thing that you find. You make the solution and then you sell it for 30 million bucks to a big medical company. Whereas in that social networking space and many other spaces, certainly in the web3 world, if you get it right, it's like literally worth many billions of dollars. And that is how valuable it is to be able to effectively deal with ambiguity and work your way through it I think.

Eric Jorgenson: Should we do some like quick track record of angel investments? I know both of you guys are like a decade in. We should both like flex and what's the opposite of a flex?

Alan Doan: Cower.

Eric Jorgenson: Like getting caught changing. My snap image was getting caught changing where you still have your shirt on, but you took your pants off. Like that's the opposite of a flex. 

Alan Doan: When your penis shows. 

Eric Jorgenson: When you are in Winnie the Pooh mode.

Alan Doan: That’s when everybody laughs at you. But when you're fully dressed, they think this guy's impressive. Okay, yeah.

Eric Jorgenson: Yeah. So, winner- 

Alan Doan: So just talking about companies we invested in?

Eric Jorgenson: So, winner, a missed opportunity, maybe something you thought was going to kill it that just died instead.

Alan Doan: Let's see, some of the favorite ones that I've invested in, like my investment strategy is literally just, like similar to what you were saying, I invest in buddies that I like that I think are smart. And I mean, with that being said, I haven't passed on any of them that have like given me an opportunity. There's been a few that I'm like, bro, you know I invest, where was the phone call? What are you doing? You raised a round from famous people and you didn't call me? might be the only ones that I missed out on. But for the most part, my biggest regrets are just not putting more in. Like I invested in- and more into the ones that did good. There's some that I wish I would have put less in than failed and I wish I'd had that back. But yeah, some of the ones that have done a good job that I really like is like Joel Wishkovsky. I've known him for 15 years, don't know if I'm saying that name right. He started Simple Contacts; it turned into Simple Health. Like now their whole thing is they're selling like birth control the same way, like Hubble contacts, it's like very subscription app store. But it's like women's health is what it turned into, but it started out as contacts and they had all the vision stuff they're building. But they're doing great. A crackpot CEO and leadership team now. 

Eric Jorgenson: Is crackpot the word that you meant? 

Alan Doan: I don’t know. Crackpot, that might be crazy. No, she's a smart, capable woman that's doing a great job. I like that I have some exposure to like women's health and the future of that, but it's all accidental and we just stumbled into it. And then what were some other great ones? Austin Allred is one that he called talked about doing Lambda and that was one that I was one of the very first checks in. 

Eric Jorgenson: That's one of my misses actually.

Alan Doan: Wish I would've written a bigger check. 

Eric Jorgenson: I remember meeting Austin. I just saw his Twitter back before he was already Twitter famous. I was like this is awesome. We met in a coffee shop in San Francisco, and I was like this is brilliant, this is going to work, has such a cool story. I think a lot of people don't know like the scrappy startups before this one, but like he was just awesome. And it didn't even like- I had $0. It didn't even occur to me at the time to try to go scrape something together. 

Alan Doan: One of my other stories, Quinten Farmer, he was an intern with me at Techstars in New York and this this dude went and started Even, like a finance company called Even, with a buddy. And that was one that like literally all the dollars I had to my name, I was like here's $5,000. He was kind enough to take my money and they just sold like a month ago and got me a very generous return. But it was one of those where I'm just like, no, of course, man, you're a smart guy, absolutely, take all my money, go knock it out. And I've just been very, very bullish on like people that I know doing cool stuff. It's funny because some of my favorite ones aren't huge yet, but like Loyalty Lion is a company over in the UK that's like the number one loyalty Shopify app. But those dudes, man, they just grinded- their first round was like $74 on a hundred dollar valuation. It was just so- back in those days, you look at some of those, it's like we're raising 200 pounds. But they were solving a problem that I saw from a commerce standpoint where I was like, man, I wish I could reward people for doing- liking my Facebook page, subscribing to YouTube. And they're like we should do that, we can do that. They pivoted whatever they were doing and started building this thing, and now, it's great. It's doing awesome. And it's a cool success story to be a part of. Seis, Trevor came out of the- Trevor McKendrick-

Eric Jorgenson: We love you, Trevor McKendrick.

Alan Doan: Your views on Ukraine are wrong, but you are a nice gentleman. I love Trevor because I knew Trevor from back in my startup weekend days in Salt Lake. And he's literally been out and slept on my couch here in Missouri. And my wife loves him. He's just a cool dude. But then he went and worked with Austin over at Lambda and then came out of there and started- he's like I'm going to build a bank all in Spanish because nobody's built a Spanish first bank. So, it's not press one for Spanish. It's like no, we are for you, and there's 40 million native Spanish speakers in America. Yeah man, checks out. So, I write a check in, again, first check in. And then people that are like, I got people that invested in Pretzel, they're like, wait, can you get me into this deal? And I was like what? He's a popular deal now? How did this happen? And it ended up just being a great deal. Everybody loved him.  

Eric Jorgenson: His newsletter is great. Like he's got a hilarious story. 

Alan Doan: The atheist Bible salesmen story. 

Eric Jorgenson: Yeah, like he is fluent in Spanish because he did his Mormon mission. And then he like came back and he built the number one app in the app store, the Spanish language Bible app in like early iPhone. He is like a Mormon who is an atheist killing it selling Spanish Bibles.

Alan Doan: Well, he left the faith in the midst of this and was like now I make all my money selling Bibles that I don't really believe in. There was actually- I think a Startup did a podcast episode on him. 

Eric Jorgenson: But like, it's turning in- I mean, I totally agree, the need for native Spanish banking is incredible.

Alan Doan: I mean, you guys have done a great job of like you identified the value of an audience very early and have focused on building. I mean, for him, launching his startup inside of his audience ecosystem has been genius. It's one of those things where you’re like, oh yeah, I should have sent out a newsletter with some smart news clips. 

Bo Fishback: Yeah, that's one of those things that like I think very differently about now than I did certainly 10 years ago, but even 5 years ago where it's like if you can build in distribution, you have solved so much of the problem of any startup, frankly. And that is one where like that audience building is just like- especially when it's so aligned. 

Alan Doan: It is why we have Eric. Eric is the audience builder. You and I are too lazy. I did a podcast for like 400 episodes every week and like through my twenties with a buddy of mine. And I would literally, man, I'd be at a party in New York, and I'd be like disappearing to the closet to try and record for 40 minutes because I promised that we'd get it out. Oh, we're two days late. And like I'm in Ukraine up at four in the morning trying to like- I was just like, man, I don't ever want to do that again. I just don't want the weight of the consistency that has to happen on my shoulders. So, I don't think I'll ever go to audience building. We need Erics in our life. 

Bo Fishback: I once, while at business school actually, started to go down the path of starting a podcasting company in 2004 with a guy who was in my class, we got reasonably far down the path. And then it was actually right when Odeo got announced and raised a bunch of money or something like that, which did not work but became Twitter, which did work, if you guys hadn't heard. And actually, when they announced the Odeo stuff, we were like, oh, that's all the stuff we wanted to go and do, oh, we're not going to do this anymore. We'll just use their product. And then that didn't even work. 

Eric Jorgenson: Podcasting was a wasteland for like the first 10 years of existence. 

Alan Doan: As it should have been. The one that always like shocks me is- is it Mark Cuban that had like the basketball broadcasting company? 

Eric Jorgenson: Yeah, broadcast.com in 1998.

Alan Doan: And that's one that was built on real player. And you're like, man, that's, it never really worked and it was okay.

Eric Jorgenson: That was the greatest like get out of Dodge of all time. He sold that thing for like a billion dollars. I think there's little to no enterprise value left. I think Yahoo bought it.

Bo Fishback: I just know that he made money and it worked out great for Mark, so awesome for him. 

Alan Doan: Yeah. I mean, that's one of those where you're like, man audio on the internet was frigging hard. It was hard and still is. I'm invested in Zencastr, which you should use.

Eric Jorgenson: Should use. I had an impartial third-party do research on podcast tools and ended up at Riverside, but I think there's different use cases. 

Alan Doan: Zencastr is great, and I love what those guys are building. And that's another, that's one of those that like my buddy Josh, he was working some job and then like needed a soft place to land. So, I had him working at the quilt company and he started, he was doing- 

Eric Jorgenson: A soft place. That sounds cozy as shit, Al.

Alan Doan: He's doing web audio on the side. He's like building mix boards and JS and stuff, and then ended up spinning out this company that like- the Zencastr  story is funny because he was making like a million dollars a year just as a solo founder. And he's like this sucks. He was just working all the time. He couldn't scale out of being the one guy that was doing all the stuff. But all the money was just- he was just like living high because he was doing great. Then he started building the company, raised the money, and you put all of that at risk. Now the outcome, it's so binary where it's either like, well, all that goes away or you're a billionaire and you're a genius. And I'm like, man, I would never have the balls to put that little golden goose up for sale. But he did, he's doing great, man. Everybody loves him. That's another good one that like I started out as an advisor and then ended up putting money in as they kept growing.

Bo Fishback: One that I like a lot, which I don't even know if you know this story, Eric, but in probably 2006 maybe, I was interviewing for CMOs for Zaarly. And when you raise like the fancy blue chip venture money, and you say you want to hire a CMO and your venture guys want you to hire a CMO because they gave you the money, now they want you to hurry up and spend all the money as fast as possible, your CMO candidate list gets gigantic. Like I remember joking there was like 50 famous folks who were applying to be the CMO of this little shitty company Zaarly, but it's because we had all this great backing, all this kind of PR stuff. So, I was talking to kind of like highly credentialed and amazing person after amazing person after amazing person. Like one of the people that I interviewed is the new CEO of Peloton who's been around the industry forever. One of them was previously the CMO of Virgin Airlines who worked for Richard Branson. Anyway, one of them was a guy who I really, really liked a lot, super, super sharp guy. We got all the way kind of down to- I thought the opportunity to work with him was going to be really fun and awesome. His name is Owen Tripp. And we kind of got to the end and he's like, one, I'm not sure if this company is going to work, and two, I actually really want to go be the CEO and I'm going to go found a company with this other guy that I know that's a doc out at Stanford. 

Alan Doan: Like, well, thanks for wasting my time. 

Bo Fishback: Well, actually I was like can I invest? And he's like, sure, we're going to go-we're about to go raise a round or whatever. And so, it was one of those where it’s like, well, can I invest, what is it you do again? And it's actually ended up being an amazing angel investment for me. It's called Grand Rounds. And they've now merged and kind of consumed a couple of other large companies in the space, but they are basically like the premier medical network for super duper high end second opinions. So like if you live in a small town and work at Walmart and have a workers' comp claim and have a problem, and you go to the little local doc and they're like we're not sure, maybe you have brain cancer or maybe you just strained your neck, all of those big employers hire Grand Rounds to have this very impressive expert network of some of the top doctors in the world to say like, hey, let me get on, I'll help you understand what's happening. We can look at all the case files. And they've, I think at their last round, they were somewhere in the unicorn club. And he is honestly, as the kind of founder CEO, just done a phenomenal job executing on a company that started as, hey, it seems like there's really smart docs that would be happy to help in other places but not quite sure when and how. And they just built this incredible network and have just expertly navigated how to sell into businesses and kind of pivoted the business model a few ways, but all forward progress. And it's going to end up, I mean, if not, there's not been an exit there yet, but it's a really, really impressive company. And it was wholly based on the fact that I knew Owen was incredibly impressive and he could have told me he was doing anything and I would've written him a check. And those are kind of- that's like one of my favorite kind of investments. And then the other one is one that kind of comes to mind that I like a lot, we'll see what happens, that actually I met through Techstars when they were in Kansas City, called Solo Funds which is a group that was basically going just directly after the worst parts of the payday loan industry and saying that like, hey, this is an industry that is full of predatory issues. Yeah, it's a really, really tough and broken industry, but it's also like very meaningful industry for the people who need it. And what happens today is they get taken advantage of. And so Solo Funds launched a company that is a much more peer to peer kind of network version of this, where nobody is out there to be a predator, and actually people are out there to say you're a single mom and you can't make your electric bill, I'm very happy to give you 150 bucks to pay and you pay me back 160 bucks when you can kind of a thing. And they built a really neat network. They just raised a round recently. I invested a few years ago. But it's a really grindy hard and messy problem that if they can solve it, it will just be such a meaningful company to so many people. And I think the team there, Travis the CEO has just done a great job at staying kind of mission focused on that. And I think it's actually going to turn into being a really meaningful company over time. And like people who you would bet on them no matter what they do or people who are just attacking those really, really hard problems where like I don't actually care if I lose all my money on that investment, I would make that investment every day of the week, but I think they're going to pull it off. So, it's kind of amazing when you can find those things. And I think, as it relates to us guys kind of shooting the shit and doing deals together, that is a thing where like once you do enough of those deals, you see enough more of those deals that honestly you could make it a full-time job, or you can team up with some other guys who are in a similar spot and say like, hey, let's do the ones that we all want to be a part of. And I think that is a fun thing to spend time on where like you get to be around smart people who want to be around other smart people who are building cool shit. And that is kind of the whole point, I think, from my perspective. 

Alan Doan: Honestly, you think about like the end of your career, not the end of your career, but at the stage of your career where it’s like what do you optimize? You have money, you have success, you have all the things that you wanted when you were 18 and set out on this journey and it's like what do you do with the rest of your life? It's like, well, you find reasons to go get good barbecue with a couple of buddies and can we leverage our skills and networking to helping the next generation? I mean, one of my other investments that did really well is these kids Bruno and Richie who started Pura, and Pura is like a, I would describe it like a Sensi meets your nest thermostat. Like it's a smart home diffuser. It's got multiple scents in there and it can like- 

Eric Jorgenson: Bo love scents.

Alan Doan: You wake up to some orange citrus and go to sleep to some lavender. And it's- these guys were like, they were right out of college, just a couple of scrappy dudes trying their best. And it was funny because I keep talking to them, like I got connected to them through like an incubator- no, actually it was through a buddy of mine that they just kept showing up on this dude’s doorstep being like please tell us how to do this, please help us. They offered me the CEO job at one point, the two founders were like, please, you come and do it. And I should have said yes, I'd be much wealthier than I am now. I was like, no, you guys got it. You're going to do fine. Like, hang in there, you you're great. But just getting to cheerlead them through their terribly insecure moments where now they're like, I mean they're well into the billion dollars and like killing it because they took that same- It was a skill they actually leveraged of just like the likable dummies that like everybody loves them. And so, they would go and I don't know how, but this huge manufacturer over in New York gave us free money. I'm like no, they didn't give you money. Yes, they gave us money to go and build this thing. Then they're like, hey, we got a license from Disney. No, you didn't. Yeah, here's the Elsa scent. They're selling it in the Disney store. I'm like how the crap? There's not a Frozen scent. Nobody can get in Disney. And they're like it just happened. They are just these likable guys that everybody loves that like- 

Eric Jorgenson: And they smell great. 

Alan Doan: Very good. They are my lesson of like every time- I've never not regretted investing with an uncapped note, that's one of those that I put in early money, 19 years of stress and anxiety later, they raised their round, which is where I convert. And I was like son of a b, I'll never do that again, but also really good job. I'm not mad. I'm going to make a lot of money on this. Those guys, man, when you start to find those people that you can be like I just want you to succeed, like it's a great relationship from an investor standpoint.

Bo Fishback: On the missed note, why, how did we not invest in Casper?

Alan Doan: Did you know those guys? 

Bo Fishback: How did that happen? Were we too late? Were we too early? Eric's fiancé was like very, very early at Casper and I don't know how that didn't make it into the portfolio at some point. 

Eric Jorgenson: Yeah, it’s a reasonable question. I think there was probably a fundraise that we missed relatively early on. I know that company, like they all placed bets like the day before launch day of like what is launch day and launch week going to look like, how long is it going to take us to sell 100 mattresses or something like that. And that blew up faster than anybody ever dreamed that it would. I think they raised like a small seed round before that. So, it like didn't exist then. Incredible brand. I mean, amazing team, Red Antler branding, really thoughtful bunch of things from the very beginning. One of the things, I don't know if this a generalizable lesson or if you guys can pattern match this, but one of the things that I thought from watching Casper is they had five founders from day one, which is potentially chaos salad, but also, they had a great e-com experience, really good design, great product, meaningful operation. Like they had a lot of stuff right that it would have been really hard to start that with two people and have it look that good and run that tight from the very beginning. I think part of it was it just looked like a really polished brand on day one because they spent probably half their seed round on Red Antler and design and product and stuff. Have you seen big successful founding teams as a pattern or not particularly? 

Alan Doan: No, I haven't.

Bo Fishback: I hate it. 

Alan Doan: I mean, the thing that you run into the most is like I hate 50/50, well, I don't hate, but like 50/50 partnerships never feel great to me. I want like a 70- like I much prefer a scenario where it's like this is our leader and I'm the number two guy. And I'm happy to be here at the number two position. When it's 51/49, I don’t know. Like a lot of people have success with that. My PTSD from my own experiences have been like, oh, we should have articulated what the roles were in the beginning. Instead, we're all co-CEOs and it's going to be fine, and we'll figure it out because we all love each other. And then like you add a bunch of money and stress and anxiety to it, you end up with one guy that's trying to pull his weight in the other direction and stuff. 

Eric Jorgenson: And a hundred decisions later, just mathematically, it's very unlikely that everyone is going to agree the entire time. 

Alan Doan: If those five founders were like I'm a CEO and here's our product guy and he's got 10% of the company, and here's our design guy and they've got 14%, like we've divvied it all up in the beginning, but we knew we had five roles we need to fill, that's great. That's awesome.

Eric Jorgenson: They did see- I mean, a lot of those- three I think of them left within a few years, five years or something. 

Alan Doan: Why wouldn't you?

Bo Fishback: On the flip side of that, I would say that I think there may be no harder grind to exist then like the solo founder. And so, if I had to choose between five and one, I'd kind of be like, well, I don't think those five are going to be there, so let's make sure we understand what it looks like for people to fall off that list. But going at it alone takes some special. That is the thing that I will tell you that like people pull it off every single time I'm amazed. I could never do it. Like that is a thing- 

Alan Doan: I always ask why man? Like such a lonely- that's a crappy way to spend a career. Go find yourself a buddy that you can like turn in the chair and be like, man, this is hard. This sucks, right? I'm all out of money and I don't know what to do. 

Bo Fishback: And it's just me. 

Eric Jorgenson: You’ve got to get a dog. We should probably cover like why start a fund? We've been personal investing for a long time, kind of started sharing deals and stuff.

Alan Doan: What’s your reason? Why are you here, Eric?

Eric Jorgenson: Because we talked about it at Capitol Camp and it seemed like a really good idea. No, I mean- 

Alan Doan: I like that this was born at Capital Camp. It seems like the most capitalistic way for a fund to be born. 

Eric Jorgenson: It's absolutely. Yeah. It's not quite what it was for, but it feels appropriate on both sides. I think it is very unsatisfying as like a much smaller angel investor to be like please take my $5,000, please. I'll help as much as I can. And you're like I know that there's a barely break even on the paperwork and like you're doing me a favor by investing. And on the flip side, it is also unsatisfying to like write a post or record a podcast with a founder for an audience and be like look at all this money I made all by myself. And so, I both want to have more of an impact on the portfolio companies that we invest in and be like when you are stuck, here's a meaningful amount of money that can actually like give you three, six months, reach a new milestone. Like we will uniquely take conviction and show that in you and try to get a company from zero to one. And on the other side, the more people I talk to who are in, I don't know, Portland, Maine, or Europe, or like places all over the world who are like I just don't get to go to Capital Camp or I'm not friends with Trevor McKendrick who slept on my couch when he was thinking about starting his next company. It's kind of like, I don't know, it feels good to be like let's dump all our money in a pool and share it all out on both sides.

Alan Doan: I mean, mine is interesting. Like my reason for being here is, I mean, like we said, it's an excuse to get together with a bunch of guys that I like. And let's have our reason to get together, talk about how we're going to help the people that we're invested in, and like that's a great way to spend a lunch. We can go on a senior single cruise at some point, wherever the world takes us, we'll adventure out. But for me, I mean, I'm investing my own cash, really having a good time with it. But I keep finding- yeah, I mean, I feel like I'm seeing more deals than I'm able to get into because I allow myself four investments a year. And so, I was budgeting a hundred grand to go in, four 25K checks, and there's some of them that I'd be like, yeah, I actually had one a couple of years ago where I was like big conviction around this, I'm going to take the rest of this fund and throw it in here and see where this goes because I wanted to back more, but then that killed my deal flow for the rest of the year. And really, it's one of those things where I think net, I'll end up making the same amount of money through our carry and stuff on this. But like the fact that I get to- after being a founder and raising money and realizing like, hey, I'm trying to raise a million bucks, and somebody says take my thousand dollars, take my five grand. Like they say yes because they're buddies, but it didn't help me get any closer to my goal. And if we're going to be 50K or a 100K checks across these, we actually- we get to write an early check with conviction that means something. And to get to, yeah, sort of outsize our impact to the founder and we'll make the same amount of money because we're putting our money in and make a return on the carry and all that, but we get to bring a bunch of people along with us and give good exposure to people into our networks that we've spent 20 years building, seems great. And it seems like fun. And I love, I don't know. I feel like, yeah, I feel like I find myself finding people that I really like to work with. I really want to go and help them be successful. We work really hard. Like I spent a lot of late nights doing the- reviewing the new website redesign. I'm good at marketing and branding stuff, and I'm good at like growth hacks and marketing. And so, I dive into a lot of that stuff with people and try really hard, but would love- a lot of times, it's just money is what they need and not anything else. And so, the fact that we can, I don't know, put a broad brush over all of that was what got me enthusiastic about doing this and saying, all right, yeah, let's use this. Let's do the same thing we're doing, but we'll say yes to a few more checks a year. And also, I liked that you guys are much more dialed into like a web3 world. I'm probably the curmudgeon of the group where I’m like eh, there's still plenty of money to be made in web2. You guys can take the web3. But it gives us exposure to other sides. You'll look at my stuff. Most of my stuff I think is consumer focused, a little bit of SaaS, but most of it ends up being a product that you're selling to somebody. And then like you guys would be a much different lens on that stuff. And I love the idea of having some exposure in my world to this stuff instead of just staying in my silo till I die. 

Bo Fishback: I think actually that last point to me is a big reason for why I want to do this. I think, one, in the same way that I didn't want to be a solo founder, I don't actually love being a solo investor. I don't usually mind making decisions. I don't ever- I'm not a follower investor. I'll never sell- When I have conviction in something, I write a check and then I kind of keep no expectations, but it's actually I think a reason I don't enjoy it that much. It's just like me by myself telling myself that I'm smart or an idiot. And that's not how I like to work, but at a kind of more maybe useful level, what I would say is I'm like pretty sure that we're at this really weird point in time where web2 and web3 have overlap and lessons to learn from each other, and I kind of keep having this feeling. So, I graduated from college in 2000 and I keep thinking if I was as smart about the internet as I am today in 2000, I would definitely be many billionaire, I think. But nobody was because of where we were in the process. I watched the Dot Com kind of boom and crash and all this stuff when I was a little too young and inexperienced to know what to do with it. And I actually kind of thought I would never see a phenomenon like that again in my life. I was just barely too young, and my dad was a little too old. We kind of straddled it, and I'm like, holy shit, it's happening again. And now I’m smarter and I know a couple other guys who are really smart, both in hindsight and foresight looking and I've seen even in the last year way too many deals for me to even like get through. So, I end up investing in ones that I have time to spend on it, but I think like that overlap of web2 and web3, and where you can take lessons from the last wave and apply them to the new while we're just looking at a whole new kind of infrastructure be built is too interesting for me to not want to dip into I guess. And it would be really easy- The only alternative is just like pretend it doesn't exist and then just go on happy about your life. But I think we're just seeing the reinvention of a lot of things and a lot of very smart founders and different organizational structures. And that's like a really fun thing to spend the next 20 years on. And that feels like a team sport to me, not like a one man sport. And I'm like, oh, this feels like a good team to work on it with. 

Eric Jorgenson: Web3 is absolutely a motivator for me too. As soon as you kind of do the work to wrap your head around it, and then like my first reaction is kind of like founder mindset of like, oh, what are the companies we can start with this new set of tools and opportunities. And you can pretty quickly get to a list of like 20, 50, 100. How can you possibly- like the right play here is sort of spread capital and understanding as broadly as you can over this whole phenomenon. And that’s a perfect way to learn. I mean, like not just individual investor, but I feel like I've already just learned in the last hour from listening to you guys, oh, that's a cool like story of that company that I didn't know how that piece of the world worked that you got smart about because you invested or the founder taught you everything. It's like, yeah, we learn so much more when there's three of us. And I think any of us could be a great solo GP if we spent 80 hours a week doing it. But I think we can kind of put our like wonder triplet rings together and be really good at it in the natural course of our lives by sort of fusing all of this together. 

Alan Doan: That sounds beautiful. It sounds like does this solve peace? Did we do it? Suck it, Putin. 

Eric Jorgenson: Is there any other reasons for fund? Because it’s worth spending a minute on why Rolling Fund in particular. It's a rolling fund called Rolling Fun. But the structure of it is meaningful I think and like let's us do this in a way that- like, I also don't think that we would be like raising a traditional fund. I don't think any of us is like- if the only options were like spend a year to raise 20 million bucks all at once and then deploy it, we would just keep doing the personal thing. So, the fact that Angel List build rolling funds that let us semi passively scale up the natural pattern of Angel investing is awesome. 

Bo Fishback: I would just say, so a thing that I did not mention actually when I was at the Kauffman Foundation, I had this very hilarious experience where Nivi, the co-founder of Angel List with Naval, they were at the time building whatever, this blog basically called Venture Hacks for anybody who was in the internet at the time, it was like a cool thing, how to start up, how many founders should you have, how to think about equity. Anyway, Venture Hacks was like a cool thing. And I just thought they were neat dudes and I had to give away money at the Kauffman Foundation. So I called Nivi one day and I was like, hey, Nivi, I want to give you some money to keep doing what you're doing basically. And he was like cool. I was like but I need you to come out to Kansas City in order to like have this conversation and high five and make everybody the foundation feel good. He's like, all right. So, he shows up. I don't know if anybody knows Nivi, but Nivi is a hilarious genius lunatic. He's one of the most interesting and amazing guys ever. So, he shows up wearing like his dad's suit from the sixties with his shirt tucked into his underwear. And like he was amazing. And he was like, hey, well, really what we want to do actually is we tried a couple of times, didn't quite work, we want to build this thing called Angel List, and here's what it is. And I was like, cool, can I just give the money to Venture Hacks and then you guys like kind of turn it into what you want to turn it into? And I think it was actually the very first money that went into Angel List, actually, I think it was the seed, it was like $500,000 seed that actually birthed Angel List.  

Alan Doan: You just called people and gave them $500,000? 

Bo Fishback: That was literally my job.

Alan Doan: Does that jobs still exist? 

Bo Fishback: But yes is the short answer. That was what I did. And it was a great, it was awesome. It ended up being one of the coolest things actually that I ever got to kind of see happen at the Kauffman Foundation. And anyway, so I kind of feel like in some ways I got to like see the birth of it and then the foundation actually ended up investing through it's like actual endowment in Angel List as it kind of got bigger and [inaudible 1:20:42], it all came out of this like program related investment, it was called a PRI. We're like investing in something that is not necessarily a 501(c)(3), but that furthers the mission of it. And so, I kind of got to see this thing born, and Angel List has just turned into such a juggernaut that I think it's really cool, to your point, as it relates to this rolling fund thing is like what I would say is I think about this very much as like a no pressure way to participate in deals we're going to do any way with some guys who hopefully you think are smart, but you don't have to go out and like raise a hundred million dollars or a billion dollars. Like one of the great secrets of venture capital is that like the better you get at it, the more time you spend raising money. And that's like hell. As a startup, think about it. It's like now your only job is to just all year long, all year long, raise money. Like I don't want to do that with my career. This is one where it is very much like, hey, they have built a mechanism so that anybody who wants to participate in it can. If you think it sounds fun, if you want to put in 20 grand, if you want to put in 2 million, like whatever, it is a very empowering tool I think for folks who are going to do deals anyway, and for other people who are maybe interested in doing it some way, but kind of want to like go along for the ride and learn as they go, I think it is going to actually be one of the great educational things for future angels. I think we'll learn a lot in it. I think actually this would never happen without that mechanism. And it is so bad ass that they built this into the platform that they did. It's like let's early adopter and try it out and see what happens because it seems awesome. 

Alan Doan: I really like that idea of like I can put five grand a quarter in. And I just get to- why did you pick these deals? So, as we submit the deals to the LPs and stuff, we have to say here's why we like it, here's why we think it's interesting, here's why we think it's going to be successful, here's the other people that are investing in it, here's what all this is about. And I mean, give yourself two years, you're out, what is that, that 20 grand a year but you have a decent track record with good exposure that you get to say how did those guys do? Like which ones did a good job and which ones didn't? And now I have enough that I can like look at and say what I'm excited about and what I'm not. That's a great point, man. I actually wish I would have done that. I ended up backing some syndicates early on in the Angel List days. And that felt like a waste of money and energy to me looking back because I have like $17 in 50 different companies or something. But like the syndicate would get so big and they’d do these like massive investments and deals all over the place. And it was almost so much that like I had no idea why they were choosing these or what was going on with them. Like they weren't- they were operating more as a traditional fund. And so, I like this a little bit more concentrated. If we were to get to $20 million a year that we're trying to deploy, I mean, it's a much different reason that you want to back us than you are right now. Right now, our goal is to like maintain our lifestyle, take a few meetings a week, hang out with cool people and be ambassadors of great startup ways and letting people come along with us, like this is a great format to do it in. 

Eric Jorgenson: Yeah. And we are going to keep it small to start with. Like a lot of friends who, when I was starting this, were like how do know, what do you do if you can't deploy the money? I was like, well, there's a bunch of answers to that. But the first is we're starting really small to alleviate that. I don't think we'll have trouble productively deploying two and a half million a year.

Alan Doan: If we had 10 million, that would actually be like, it's like how do we- now we've got to fight to get into deals. We've got to like really work to get it through. And it's like, no, we don't want that. 

Eric Jorgenson: Yeah. I mean, I think like slowly raise the cap as we get- if we're like, we give ourselves a 90%, 95%.

Alan Doan: If we are geniuses, it's our duty. How dare we not? 

Eric Jorgenson: We have to keep balanced, like the amount of genius and the amount of capital. 

Bo Fishback: I do not think it will be a challenge to deploy the capital, frankly. I think it is absolutely going to be a thing where we all have pretty solid deal flow and really, really good networks. And in some ways, like even at this kind of size that we're talking about now, we're going to have to pass on some things that look good. And that is okay and good discipline, and I feel good about it, but I think I really like that it's very approachable for anybody who wants to come along for the learning journey. I think we will learn a lot in the process. We'll be as transparent as you can possibly be because that feels like the right thing to do.

Alan Doan: And listen, like we're available for you to talk to. I mean, anybody can take 30 minutes of Eric's time anytime they want. You're welcome to it, just ask a question. That's fine. But we are an approachable group if you'd like to hang out. Come to Kansas City. I'm sure you'll be doing some dinners or something for our LPs. They’ve got to get something out of this. 

Eric Jorgenson: Yeah. They get the returns. That's what I'm excited about actually. And I want to like apply your community genius to this because I think-

Bo Fishback: We should buy a town.

Alan Doan: You're absolutely right. I love it. Rolling Fun Town. 

Bo Fishback: Look, I don't want to say that Al’s only got one trick, but he does have a trick – buy a town. 

Eric Jorgenson: Truly though, I've been so- like I've been blown away by how brilliant the LPs that we have are so far. They are in these- I mean, there's a VR AR engineer from Facebook. There's Google execs with like amazing- their own portfolio. We've got series AVCs. We've got engineers, buddies of mine from hardware companies. I don't know, like people who are very, very smart and who also the first thing out of their mouth after they say I'm in, but also put me to work. I feel like a lot of GPs, probably especially with bigger funds, are like very much have this perception of they're paying me to be the lone genius and just like shut in a room and I'll take care of everything. And they like keep LPs at arm’s length. And I feel like there's such an opportunity, especially with this group, who's like we'd be very transparent and be like here's our portfolio. Here's where they need help. Here's where we can connect them, use them.

Bo Fishback: At some size, do we pivot slightly into a rolling fund DAO? Is that just like what happens there when the network is big enough? 

Eric Jorgenson: I mean, you can imagine a Discord that's like here's new opportunities, here's how we bring- So, I think we will continue to explore how we involve LPs and bring them along.

Bo Fishback: Does someone already have a decentralized venture fund? Is that a thing that exists? It seems like a thing that would exist. 

Eric Jorgenson: I feel like I'm sure it exists in name of some sorts. I mean, there's definitely like, I don't know. Like in crypto, crypto stuff just kind of popped up overnight that is like shared treasury investing stuff. But it's also like crypto only, which I don't think- like we are certainly crypto, but I don't think we want to be crypto only yet. 

Alan Doan: He's absolutely right. 

Eric Jorgenson: Don't leave me.

Bo Fishback: We've got a web2 guy sitting right there.

Alan Doan: That would be whack. 

Eric Jorgenson: Yeah, I think a lot of the motivation is learning oriented, like for us and for LPs and building out this portfolio. And I mean, for us, we all get more exposure to a much longer list of companies than we could personally and the same is true, play the power law game and try to just get money into 10 or 20 companies a year instead of four. 

Alan Doan: It's an education. It's cheaper than Harvard, so you're welcome.

Eric Jorgenson: If you only get to pick Rolling Fun or Harvard-? 

Alan Doan: Yeah, for sure. Rolling Fun. I mean, we've been to Harvard, there's nothing there. 

Eric Jorgenson: I remember like saying or tweeting or something, I would be like my new goal is to go to Harvard Business School and Bo is like eh, I wouldn't fight too hard for that, maybe choose a better goal.

Alan Doan: Yeah. I don't know if you had this, because I did the OPM program, the owner principal manager, which is like the rich kid version. It's like the executive MBA where you don't have to do any homework or anything. And I felt like three of the teachers were what I had in my head as like Harvard teachers. And then there were some that like shouldn't have been in a community college. They were just like terrible. And then there's a few that were like unremarkable in every way. And that was like the mix. Is that- was that sort of the business school? 

Bo Fishback: Yeah, I think that's right. I think it's right. 

Alan Doan: There's a few that you're like I am inspired and better because I've been in your class. And then I was just shocked at the others. I'm like, how'd you get a job at Harvard? Do you know a guy? Did your uncle start this? What are you doing here? 

Bo Fishback: Did your uncle start this? Did he start this little rickety show here or what? 

Alan Doan: Frank, you've got to be related to these guys somehow. 

Eric Jorgenson: Should we talk about what we look for in companies, companies that we love principally?

Alan Doan: I feel like that's a hard one to encapsulate and answer because- 

Eric Jorgenson: It's stuff that we're excited about.

Alan Doan: It's founders, it's the idea, it's the traction. It's like all this stuff ends up being a part of like what gets me excited for one. And if any of those are missing, it doesn't mean I'm not excited about it. I don't know. Do you have anything, as you look at stuff, is there some commonality for you, Bo? 

Bo Fishback: I think that I'm like a pretty founder first investor, and I would honestly bet on someone who I really believe in almost regardless of what their idea is because I think they'll figure it out along the way on the one hand. On the other hand, I think that kind of in the spirit of a lot of things are going to get reinvented here over the next 10 years, I really like the themes of things that have been proven in a web1 web2 world that just don't have a corollary in the web3 world, for example, like you already know the thing is going to work and it's just a question of execution and when. And I think those are two different buckets. And what I really like is when those buckets get combined and it's like I would bet on this person for anything, and they so happen to be working on kind of inventing the next version of the internet or technology or whatever. And like the more of those you can find combined, the better. But I think that it would be tough for me to like write out exactly what that looks like. It'd be tough. I think that's like one of those, like no shit, you want to find a good founder, so does everybody. 

Alan Doan: What kind of quilt company? That's what I want to know.

Eric Jorgenson: Do you own a town? Because if not, I may not be interested. I don't know. Can you thread a bobbin? The better you know the founder, the less other stuff you feel like you need to see.

Alan Doan: That's true. Which, I mean, honestly, looking at like our network that we have where we've been friends and buddies with all these people, like investors, man, I feel like they have a crappy network. As an investor to meet somebody and try and build that relationship, you're disadvantaged day one. But as smart people that people call to riff ideas on any way and talk about how to do it or a call when they have a problem anyway, we've got great networks of great smart people that want to be around us and we want to be around them. Like that's going to be our biggest advantage is we actually- I mean, I invest very rarely in people that I don't know or don't have very qualified- 

Eric Jorgenson: The earlier the stage, I think the more true that is.  

Alan Doan: I don't know, man, once you get to the later stage, I'm like I can't make any returns on this. My five grand isn't going to do anything. Turn it into 10 grand, I'm putting it somewhere else.

Eric Jorgenson: It becomes more, I don't know, it becomes more quantitative, more like high analysis. Like these early-stage things are very much even if we were full time- like you give up something by no longer being a founder, like you are a better investor because you're a founder and vice versa. I feel like we see that over and over again, which is why, again, why rolling funds and these mechanisms are so awesome because more and more and more founders can very productively like allocate capital in spare time to people that they know and trust and opportunities that they see. And I mean, how many of yours have come from being like, oh, I, as the CEO of Missouri Star Quilt Company, really want to use this product and put it to work and I have a problem that this company solves and please solve it for me?

Alan Doan: No, I mean, there's certainly a few of them that come from like- I mean, my world in e-commerce, like I know the things that exist and the big holes and gaps that are there. And so, when somebody comes along and says, hey, I'm going to build the loyalty app that's going to reward people for doing these random actions on the internet, I say, oh, that's great. I've Googled for that exact solution a number of times. I think you'll make a lot of money. You should do it. And yeah, there's a few of those. I mean, even our first investment that we made in the fund Wearloom, that's one that I look at and say, man, I could see the value of having that data in a hundred products. Like I can't wait for this to exist and you're going to make a mint selling this all over the place. Like this should absolutely be a thing. 

Eric Jorgenson: Talk us through Wearloom. 

Alan Doan: Yeah, Wearloom is cool. He  is a cool co-founder, Samuel. But they're doing a product where they go and crawl all the second hand sites. So, like you've got your Posh Marks and your eBays and your whatever else. And right now what you do is you go in and say I am looking for this Coach bag and price range, qualifiers of it, and here's the things. And then like tell me when you get one. And so, they're crawling and adding more and more inventories. They're looking at all the sites then pinging you and saying, hey, here they are at this price. And then if one shows up at a price that you're interested in and a condition that you like, you go get it. Which is like a lot of people see a lot of value in that of being like set up your alerts and just have it crawl everything. And the hard part for them is they're using some machine learning and stuff to match. They've got to figure out what that random item is that's been listed on eBay and is it the same as this other random item that's been listed on Letgo or whatever. And so, there's a bunch of work in sort of building that product database on the backend and matching it, but like what's cool about it is then they could take that and give me a value to an asset that I've got on demand and also give me general inventory and sell through-ability and all the other stuff related to it, which a lot of these secondhand places would love to have as a data source for them. So, I look at that. They have great retention, 97% stick around. People stick around. They have more people signing up. Well, obviously, but like it's a good growth rate and referral, like the K factor is meaningful. And so, both of us, we like asked our wives, would you use it? They were like oh yeah, that's a great idea. I love that. It's like, okay, all right, this checks out then, we should do it. 

Eric Jorgenson: Yeah. A lot of users, a lot of growth, and a great retention for super early stage. 

Alan Doan: I'm excited for the product to turn in to- Like right now it's just alerts, but it'll turn into more of a web-based product that will do more and more. And people- I can just see going there instead of ever going to like an eBay or something. Why would you start your search anywhere except for on Wearloom? 

Eric Jorgenson: Where did you encounter them? Do you remember? 

Alan Doan: Yeah, it was a referral from Austin actually. Austin has his fund and he invested in it and sent him over to my way because I’m commerce world junkie. So sent it over to me and I got to chatting with them. It was great. 

Eric Jorgenson: That's awesome. What else should we cover? I feel like we've done a lot of- covered a lot of ground here. We can talk through some of the companies probably conceptually that are like on our short list. 

Alan Doan: Let's not. Let's wait until we cut a check. 

Eric Jorgenson: We'll keep some. We'll hide some of our shimmer.

Bo Fishback: In your town, have you yet built your podcasting studio?

Alan Doan: Of course, I have recording studios. I’ve got video recording. I mean, come on, what is this? A Cracker Jack? 

Eric Jorgenson: Why aren’t we at Al’s studio covered in quilts? Yeah, I want a quilt on my lap when we do this next time. 

Alan Doan: You know what we should do? We should make quilts. That'll be a bro activity. 

Eric Jorgenson: I'm already like a sous chef of quilting in my own house. I got it. 

Alan Doan: You are good at ironing is what that means. A sous chef of quilting. 

Eric Jorgenson: Is there a technical term? 

Alan Doan: Yeah, no, that's right. That’s how we call it in the biz.

Eric Jorgenson: All right. If you want more of our shenanigans or to read probably a higher concentration version of this, we wrote a bunch of stuff on rolling.fun and we’ve got a link there where you can subscribe to the fund if you want to. 

Bo Fishback: It is a great URL, rolling.fun.  

Eric Jorgenson: Bo nabbed that URL. It is extremely clutch. 

Alan Doan: Go daddy fingers.  

Eric Jorgenson: Bo knows how to get a URL. 

Bo Fishback: My list of owned URLs is much, much larger than my list of used URLs. So, if you're looking for a URL, I may already own it, guys. 

Eric Jorgenson: This one converted very quickly.

Alan Doan: Those Friday nights where like you had a hundred, it was a dark hole where you were like what was I thinking?

Bo Fishback: See, this is why I need to work with other people. It’s too dark of a hole for me to navigate on my own. 

Alan Doan: I sat on the domain Class of Khan for a long time. I wanted the Khan Academy. Like it's just such a good name. 

Eric Jorgenson: I've owned ghoul pool, ghoulpool.org I think for about five years now. Someday, I can't let it go.

Bo Fishback: My current most unused and proud domain is guysguysguys.com.

Alan Doan: You can only use that for one thing. 

Bo Fishback: I used to always come into a meeting all excited with Eric and I'm like guys, guys, guys, and then at some point, I bought it and he's like you know that's not what guys, guys, guys means? It's totally different when you write it down. Damnit, I blew it.  

Eric Jorgenson: I was so excited to end this recording before Bo was able to give context to that. 

I appreciate you hanging out with us today. Thank you so much for listening. I truly hope you had a great time. Those guys are hilarious and I love every minute we get together. If you would like to invest with us somehow, after hearing that, miraculously, we have availability for investors starting this quarter. The minimum is 16K a year, and unfortunately, we are limited to working only with accredited investors. But please remember if you don't know this already through your own scars, startup investing is incredibly illiquid and quite high risk, so please be careful. You can read a lot more at rolling.fun to get some more context. If you're interested, we'd love to have you join us. And we'll keep publishing episodes like this with our investment updates to bring you all along for the ride. If you liked this episode, you will also love my conversations with Shane Mac, who was one of my inspirations for starting this fund, and Chris Powers, who's an incredible operator and capital allocator in a totally different space in commercial real estate. And he's got a great story that you might appreciate as well. A thought to leave you with since we're on the topic of capital leverage is make sure your money has a job. Even if it's not with us, just put your money to work somewhere, make sure it's productive, and remember that your money can work harder than you can.

Investing, Podcast, OperatingEric JorgensonInvesting, BusinessComment