Deep Dive with Josh Baer

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This is a podcast episode titled, Deep Dive with Josh Baer. The summary for this episode is: <p>Today on The Daily Bolster, Matt welcomes Josh Baer, the founder of Capital Factory, the largest active early-stage investor in Texas. Josh shares about starting Capital Factory, his love for entrepreneurs, and chasing opportunity.&nbsp;</p><p>They also chat about his career, which began as a founder in a college dorm room (or, depending on your definition, as a grocery store bagger). Tune in to hear Josh’s perspective on becoming an early email expert, handling acquisition as a CEO, and more.&nbsp;</p>
Starting an ESP in college
06:00 MIN
Transitioning into speaking and consulting gigs
07:15 MIN
Growing his business - while still in college
02:54 MIN
A 10-year run with SKYLIST
03:03 MIN
Selling Skylist to Datran
02:33 MIN
Staying onboard post-acquisition
02:26 MIN
Managing IP with multiple irons in the fire
02:36 MIN
All about Capital Factory
04:26 MIN
Josh's most impactful experience
03:28 MIN

Intro: Welcome to The Daily Bolster. Each day we welcome transformational executives to share their real- world experiences and practical advice about scaling yourself, your team, and your business.

Matt Blumberg: Welcome to The Daily Bolster. I'm Matt Blumberg, co- founder and CEO of Bolster, and I'm here with my friend, Josh Baer. Josh is the founder of Capital Factory, which is the largest active early stage investor in the State of Texas. And Josh, as you will hear a lot more about in the half an hour to come, loves helping people quit their jobs and become entrepreneurs. Josh, it's great to see you.

Josh Baer: Hey, Matt. Great to be here.

Matt Blumberg: Yeah, so Josh and I have known each other for many, many years. We were both in the email business for a long time.

Josh Baer: I think we're into the decades.

Matt Blumberg: I think we're into the 20- plus probably, or pretty close. And as you'll hear at one point, Return Path actually acquired one of Josh's companies, OtherInbox. Josh stayed on as kind of senior advisor and counsel to the executive team for a year or two while he was getting his current business off the ground. So, Josh, it's a pleasure to have you here today. And I think the arc of your career, which is my kind of format for the Friday interviews, is super interesting. I went into LinkedIn even though I know you and I know the big things you've done, and I clicked on sort of see full profile and it was like load more, load more, load more. And then there was a button that said, " See all 43 items," which is more than the average, I would say, more than the average bear.

Josh Baer: More than the average bear, right? Yeah.

Matt Blumberg: So I'm not going to go through all 43, although it's pretty interesting just to scroll through them, but-

Josh Baer: I think I'll go all the way back. It's the first one is grocery bagger at the grocery store.

Matt Blumberg: Let's start with your first significant company, which I think you would say is SKYLIST. Is that fair?

Josh Baer: Yeah.

Matt Blumberg: SKYLIST started in the dorm room, although interestingly just looking here, there were 10 things on your profile before that, but let's start with starting a company in dorm room that stuck, that became a real company, a real part of the email industry. So talk about that. How did you conceive of starting an email service provider while you're a college student? It's a pretty wonky B2B- type play.

Josh Baer: Yeah, exactly. It's real funny. And I also now teach a class at the University of Texas for student entrepreneurs. And I talked to a lot of them were thinking about how they could start a business in college and what they should do and what they should focus on. And one of the first things I tell them is, " Well, it's pretty unusual to go start a business and have some brilliant idea in the shower about something you don't know anything about. Usually, you got to know a lot about something that's where it comes from first. And so you got to pick something you're really passionate about or that you really know a lot about or you can be an expert at." And this was, as I was getting started, was in the mid'90s, 1996 to '98 kind of timeframe. And really the internet, the commercial internet was just becoming popular. You were probably at Moviefone or something at the time.

Matt Blumberg: That's right.

Josh Baer: And it was like people were just starting to basically build websites to sell that just like you buy airline tickets and it was just the start of all the different things. And so the big thing was building websites. Everybody wanted to build a website, everybody wanted to run a web server. And building websites was programming. If you could write HTML, that was being a coder, which I think most people wouldn't consider necessarily being a coder today. And so I was a poor college kid going to studying computer science at the time, but I wanted to run a web server and I wanted to run a website and you could either run it on Linux and then you had to go learn how to go install the Linux stuff. And Linux is a lot better today than it was 20, 30 years ago. It wasn't that great back then. It was buggy and hard to use and not well documented. Or if you wanted to run a website on your Mac, there was this program called WebStar by StarNine. I don't know if you remember StarNine. And everybody wanted to run WebStar, Chuck Shotton had written WebStar. And so I wanted to get a copy of WebStar, but WebStar costed like 800 bucks and I was a college kid. There was no way I was buying a copy of WebStar to be able to run a web server for my website that didn't do anything or make any money. And so of course at the time, the only way I could possibly get a copy of WebStar legitimately was to apply for the beta software program to get into the beta program, which kind of doesn't really exist anymore. This isn't a thing. They used to have free trials or early releases or whatever, but that used to be a thing and it was secret to get into the beta, you had to apply and fill out a form and they didn't let everybody in and they were really looking for mostly real customers. And so of course I go fill out the form signing up for the WebStar beta for program, and it's ask me how big my website is and how much traffic I have, and I'm like, " None." You have nothing to say. It's like, " What's your net worth?" " Zero." And so I'm not looking like a very good beta customer, I think. But at the same time that I'm filling that out, there's another program right next to it called ListStar and they had a beta program too. And I have no idea what ListStar is, but filling out the form has all the exact same questions, so it was really easy to just copy and paste and fill it out at the same time. And so I applied for the ListStar one too. And it turns out everybody was applying for the WebStar one, everybody wanted the web server and that was their real business. And so they were pretty picky, they could choose from who got it. And I did not get selected. I did not get into the WebStar beta program. But I think not that many people applied for the email one, for the ListStar one. And so they probably just accepted everybody. And I got in and I suddenly, I get like, " Congratulations, you got into the beta program." And so I get this software that technically costs like$ 600 or $800 and it shows up in the mail in a box with CD-ROMs and a manual because you couldn't even download it over the internet yet. And so suddenly I have an email server. I was like-

Matt Blumberg: Congratulations.

Josh Baer: "I don't know what to do it." I'm just like, " I don't do anything with email." But I'm a college kid, I've got more time than money obviously. And so what I do, I read the manual, I figure out kind of like, " Hey, here's what it does." And I install it and set it up and I start making it do silly things that didn't really make a lot of sense, but were cool little demos, like receive an email and the computer would read off the email or something, talk or something. And so that was how I suddenly started becoming an expert at email. And first I just became an expert at this one piece of software that was super niche, but I read the manual and nobody reads the manual apparently. And so there's this online group, almost the equivalent of a social media thing today, but it was a news group or an email list, and it was for all the people in the beta program and people would ask questions. And the people in the company would answer their questions once or twice a week, but I was just sitting there at my computer all day in college. I would answer the questions all day long right away because I knew the answers. And so then eventually the company reached out to me and they said, " Hey, who are you? Who's this college kid? The person answering all the questions?" And they were like, " Why don't we make them an intern?"

Matt Blumberg: Yeah, I was going to say did they offer you a tier- two support job?

Josh Baer: Yeah, they basically made me, or they just were like, I mean, they could tell I was going to Carnegie Mellon, I was studying computer science. They fortunately basically gave me the support job but gave me a lot of freedom. They were like, "And you can go do other stuff, like build add- ons or do other things." And so the next thing that I did that really bridged my career and also went from being a geek to being a businessman and learning more of the business side of it was there were these conferences going on like the South by Southwest of the day, which were Macworld, and Mactivity, and Internet World, and these other conferences that I'm sure you probably remember going on at the time. And I was a freshman, sophomore in college, but same thing, I wanted to go to these conferences, but they cost like$2, 000 to get a ticket. I can't afford a ticket to go and the company has no reason to really send me. So I start filling out speaker applications and I start making up things to come talk about and give talks. And I say this is just as true today as it was 20 or 30 years ago, but everything on the internet, there was always something that was only two months old that I could be an expert at because it just got invented. So there's no experts at it and I could be the expert at it and I could go teach about it. It was usually some email thing. And there probably weren't that many college kids applying to come speak at these conferences. It actually probably was kind of cool to have one or two of them. So I started getting accepted. And the company, even though they probably wouldn't have flown me on originally when I got a speaker invitation, they were like, " All right, well, we're already going to be at that conference. We'll fly you out there. We'll pay for your travel and stuff." And so I started getting flown out. I'm in Pittsburgh going to college. I started getting a fly out to Silicon Valley to go out to these conferences and be a speaker, and I got a speaker badge and I'm like going to the speaker dinner. And then I realized that who goes to conferences? The salespeople and the marketing people, that's who the company actually sends to all the conferences who does Bolster send to conferences? You mostly send the salespeople.

Matt Blumberg: Or me.

Josh Baer: That's who's actually going. And they're setting up dinners and they're setting up other things. So I'm out there as this college kid and I'm meeting all the salespeople at the company. And the marketing people that are out there doing stuff, because they invite me to the dinners and things like that. And so I get to know a bunch of the salespeople. And so then one day one of the salespeople calls me up and they say, " Josh, I have this deal I'm trying to close." And they're trying to buy our software and imagine this is off- the- shelf software. It comes on a CD- ROM, they don't customize it or change it for you going like, " Can you add a button to Microsoft Word?" They're like, " No, we don't do that." But they just kind of needed it to do this one extra thing for them to be able to meet their needs, so they would buy it. And the salesperson had met me and said, " Josh, I think that you could probably get it to do the thing that they wanted to do and then that would help me go close this deal. So how about I send you a pizza and you go do this thing for them and help me go close this deal?" And I'm like, " All right, I'm in college, I like pizza. Go for it. Great." So I look at the thing, I set it up, I fix the thing, that guy gets the customer, I get the pizza, everybody's happy. But now the sales guy has a new tool in his pocket for closing deals. He's got Josh, right? Like, " Oh, I can't get this deal closed. Well, I know this guy. If we send him a pizza, let me see what we can do. Maybe we can make something happen." And of course, soon I at least stopped accepting pizza and I converted to saying, " Okay, well maybe I get paid 20 bucks an hour," or whatever it was at the time that was pretty exciting for me as a college kid. And that really grew into a consulting business where now on the side I'm doing little consulting projects. And so now I go and I start, the analogy today to try to just quickly put it in perspective would be I just start going out on social media and answering everybody's questions about email. Like I'm the email guy. It wasn't on Twitter or Facebook, it was on somewhere else.

Matt Blumberg: It's like some listserv somewhere.

Josh Baer: Yeah, I just start looking for all the things about email and I just start going and participating and answering people's questions and being helpful. And what I learned was you answer a couple of people's easy questions. "What do you know?" They'd ask you more questions, they'd ask you harder questions. And so eventually they'd ask me a question that was a hard enough question that I could say, " That's going to take me an hour or two to really figure out for you. I do this consulting work. Would you mind paying me to do it?" And I started using that to build up a consulting business. So now I got a little consulting to get going. I even hired one or two of my friends, you probably remember Ian Ragsdale, who was one of my fraternity brothers, and hired him. So I was pouring out projects to him, him and Joel. And then the last real key inflection point for me that turned it into from a consulting service into a business, a SaaS business, that word didn't even exist then, was I had this one customer, David Rothenberg, and he ran an email list, a community that was all, he was a book publisher. And so it was an email list for all the people that were really into book publishing. And he had this community that he was running on ListStar, on the email server, and I was one of his consulting, he was one of my clients. Whenever his thing would break, he'd call me up and say, " Josh, my server's broken. Can you come fix it?" Or like, " I want to change it, can you come customize it?" And he'd been a great customer for a long time. And so one day he called me up and he said, " Josh, I have this idea. My server, it mostly works, but it crashes every," you remember when websites used to crash. This doesn't really happen anymore, but he's like, " The server crashes every week or two or whatever. And then my server goes down and then my email stops working and then I got to call you and it takes me a couple hours for you to come fix it and my customers notice and I pay you like 50 bucks and you fix it." " But Josh, you run a server in your dorm room at college and it probably crashes once a week too, but you're sitting right next to it in your dorm room because you're in college, and you just hit restart right away and nobody notices because you're there all the time. So how about instead of every time something urgent happens, I call you and pay you 50 bucks to fix it, and instead just pay you 50 bucks a month no matter what, and you just run it on your server?" Now, this to you may sound not totally obvious like every other SaaS business in the world and we'd expect everything to work today, but this was a revolutionary idea. That was not how anyone did anything.

Matt Blumberg: Yeah, that's right.

Josh Baer: If you wanted to run the server, you had just buy a computer and run it on the computer and keep the computer plugged in all the time.

Matt Blumberg: That's right.

Josh Baer: And this idea of like, " You're going to run it for me and I'm just going to pay you a monthly fee," that was a really new idea kind of to me.

Matt Blumberg: No, that was new to the world at that point, right?

Josh Baer: Yeah. There was no SaaS, right?

Matt Blumberg: The term of art was ASP, Application Service Provider.

Josh Baer: Exactly, Application Service Provider. You're exactly right.

Matt Blumberg: That's what became SaaS.

Josh Baer: SaaS, right. Pre SaaS, it was ASP. I was an ASP. Now I'm a college kid, I'm super optimistic and I'm thinking, " Well, nothing's really going to go wrong. This is easy. This is like 50 bucks a month of free money. My parents bought me the computer. I'm plugging into the school's internet connection, I have no expenses. This is the greatest thing in the world. I have free beer money." So I'm like, " This is great." Now I add a new line to my signature in my email that's like, " Hey, for 50 bucks a month, I can host your email list." And now I start going and answering way more, even more questions. I'm answering everybody's questions because in the end, if you're having problems with your email list, really you'd rather just have somebody else host the email list. It's like, " Let me just pass it off." And so 50 bucks a month at a time, I start adding customers onto my SaaS business, which was SKYLIST, which that was what was called. And those customers, this is before email marketing, this is before spam. No one's selling anything. They're like people talking about stuff. They're small. And then over the course of my college career, because I graduated in 1999, right around'98,'99, people started selling things. They started going like, " Oh wow, I have this big list of," because they've been like had a website and all these people have bought stuff. And they're like, " I have all these people that have bought something from me. What would happen if I sent them all an email with a 10% deal or whatever?" And it turns out that works really well and nobody had ever done that before either. And suddenly they all start emailing their customers. And so now I get all these people signing up to use our service who are a different kind of customer. They use it, I almost can't tell at first because they don't really look that different, except they send more email and they're finding me, they're signing up. And it was the email marketing industry. It was this whole marketing industry coming at me. And then that was, depending on how much time we have, that's a whole other story that you know a big part of, but then that was suddenly having to figure out and realize like, " Oh wait a minute. Okay, there are people that are signing up to use our service and some of them are sending bad emails. How do we monitor them? How do we keep track of what they're doing? How do we figure out the right way to do this?" And that was a whole part of growing that company. But the beginning was that, it was really just me knowing something about something obscure that not a lot of people knew a lot about that made me an expert about something even though I was a college kid, and talking to lots of people, meeting lots of people, trying to be helpful. And then someone else really coming to me both times with the idea, coming to me saying, " Hey, could you help me with this? Could you go do this for me?"

Matt Blumberg: Yeah. I mean, what strikes me hearing that story is it's incredibly organic. And what you were doing the whole time was customer discovery, but you weren't doing it by going out and asking people things. You were doing it because people were asking you things and led you to start a real business. But I want to ask you one question to sort of wrap on the SKYLIST part and move on to the next one. So that was a 10- year run. So you started it in your dorm room, presumably not freshman week, so sometimes sophomore, junior year, whatever. So you're running this company.

Josh Baer: Sophomore, yeah.

Matt Blumberg: Yeah. So you're running a company for seven or eight years post college. You've never worked anywhere else other than bagging groceries or things you do as a kid. If you could point to one influence in that chapter of your life, who taught you how to be a CEO, or did you teach yourself?

Josh Baer: Yeah, that's a great question. Through the SKYLIST time, I was definitely a very arrogant young CEO. I was excited and proud to be a young CEO and to be figuring it out as I went along. And there was this narrative in my head that you didn't really need to learn business or something like that, which I don't think is true anymore. So when I look back at myself as an early CEO, wow, I feel like I've grown so much and I've learned so much. And I think I'm such a better CEO now in so many ways. I hope so. I think my role models, to be honest, there weren't that... So I moved to Austin and fortunately I've had some really great role models, but I came to Austin and in the middle of that, spent a year while I was still doing SKYLIST working with Trilogy and Joe Liemandt. And that was an incredible experience that was really transformative and opened my aperture up to a lot of different people and ideas and business models. And so that was one really major influence in that was Joe Joe Liemandt and also Ravi Gururaj, someone else I worked with there. You were one for sure, Matt. As SKYLIST was growing, Return Path was a partner of ours. And then even kind of Scott Banister and Scott Weiss and a few of the others over at inaudible. There were other companies that were partners of ours that were kind of like the people I would look to for advice about how I could navigate things. Trevor Hughes. Do you know Trevor?

Matt Blumberg: Trevor, absolutely. Yeah.

Josh Baer: He wasn't necessarily a CEO. And I feel really fortunate I had a lot of people like that that I could look to. And it was before you wrote your book, which I've got here of course, but you already had such a playbook for Return Path and it was something that I got to see, but from both sides, from the outside and I could already see that the company was running on this rhythm and this pattern and this system that seemed really intentional. And then after we got to work together, I got to see from the inside too.

Matt Blumberg: Yeah. Well, I think look for all founders, or at least all founders who are sort of thoughtful about the craft of being a CEO, it is you learn from wherever you can learn, whoever you see. So I'm now scrolling through LinkedIn, and again, it takes a long time to get from one of your major things to the next, because so many interesting things in it. But when you sold SKYLIST, you told it to Datran, and I didn't realize you stayed there for five years. That's an unusually long time for someone who is so entrepreneurial and such a founder to be at one place. What kept you there? And noting that there are a bunch of overlapping things that it looked like you started or co- founded or whatever along the way, so maybe that's the answer.

Josh Baer: Yeah, I'd say the real window is about two years. I find when you sell a company, it's very unusual for the founders to stay more than two years. The first year, I've only been through it a few times myself, but I've seen a lot of people go through it. The first year goes really quickly, it's exciting. It takes six months of announcements and meeting people and shaking hands and doing all these different things and then transition all this stuff to do to transition. And then the next year sucks. The next year is just one after another. Someone else making a decision that you wouldn't have made about your people and taking the company in a different direction. And that's not really fun at all in general, and you have a lot less influence and control than you used to. So that's just a generic thing. That's not a comment about any one company or anything, but I think that's a really common pattern is the first year is kind of rosy and then the next year it gets harder and then they kind of want to get out of there.

Matt Blumberg: Then they leave. Yeah,

Josh Baer: So in my cases, I found two things. One, that I was able to use each company, I'm very proud of the fact that I'm still close with I feel like almost everybody I've worked with. I saw Joe Liemandt from Trilogy yesterday, I'm doing this podcast with you. I just got a text from Matt at Datran who just got engaged, and I'm still close with all these people that bought my companies or that I've worked with over time. And I think that's something everyone should work really hard to go do. And so I was able to use, every time I sold a company or did something like that, I was able to use that as a platform to help go launch my next thing. And so as a result of that, was able to, as part of that, part of keeping my costs, I'm a bootstrapper hard, keeping my costs and everything else though was typically while I was starting OtherInbox, I was still getting a salary and my healthcare from Return Path. That was from Datran.

Matt Blumberg: From Datran. Yeah.

Josh Baer: From Datran at the time. And then with Capital Factory, there's part at the time of that, at the time where that was happening with Return Path. And another story that I often when I'm advising people who are selling their companies, I actually tell them about it, about a story that a conversation you and I had, which was similar to the other one. I don't know if you remember this conversation or you remember it the same way, but it was the end of my second year after we had sold the company and I had sold the company to Return Path. And so naturally my two year, we had a two- year agreement in place. And during that time I had certain salary and benefits and equity vesting and other things like that. And there wasn't really a huge role for me to play in the company at that point moving forward, the way things had evolved and we've gone through all the transitions. And as I recall this conversation, I called you up and I said, " Well, Matt, everything's coming to an end." And I said, " But if you want, you can extend my contract for another year and you can pay me for another year if you want, and pay me and give me health insurance for another year. I'm okay with that." And you looked at me and you were like, " Well, Josh, why would I want to do that?" And I was like, " Well, I mean, just if you want to, but if you do that, that means my non- compete also extends for another year and I'm available to you." And I wasn't trying to threaten you or anything. I didn't have any specific plans, but actually it was pretty cheap to keep me around and not have to think about me doing anything or whatever else. And again, I don't think it was some threat, but in both cases it was like I found I was able to stay on as an advisor, as a helpful person in different ways. It's pretty easy to be helpful to the company for a long time where it's worth keeping you around and you can do helpful things. And I found with almost every one company I've been with, every company that I sold, yeah, for a year or two, I was heavily engaged, but I was on the payroll for a while just because I left on really good terms and we were all trying to be hopeful and we were all doing stuff cross- pollinating each way.

Matt Blumberg: Yeah. It's funny, I don't remember that conversation, but as you're saying it, I can imagine it happening. So yeah, you continued your pattern. You're going from big thing to big thing while starting or helping other people start some small things along the way, a lot of overlap and things. Have you ever had an issue with that around IP, work for hire, transparency, or how have you thought about that? Because the reason I ask that question is a lot of entrepreneurs and probably a lot of people who listen to this podcast have irons in the fire all over the place. And I'm wondering if there's any story from your career where you didn't do something right or you ran into some issue as you were doing lots of irons in the fire?

Josh Baer: That's a really great question and I'm glad you brought it up. It's something I'm really proud of is that I actually don't think of anything right away like that. And I've been through a lot of complicated transactions and transitions and I think one big reason why I'm not thinking of something right away like that is just having a lot of, well, and I'm sure there are things that have come up, I'm sure there's probably something somewhere, but in general just really starts with transparency. Not doing things behind people's backs, making sure that everything's on the up and up and really clear about what you're doing and why you're doing it. And just recognizing that relationships are really important, that you are going to see people over, and over, and over again. We have, I mean, literally now through four or five companies over time in different ways. So just how you treat people is really important and how you leave things is important. So yeah, that's an interesting perspective. It also makes me think even just also how I try to handle employees and people leaving my company. And it's not something that even when you try your hardest, you'll never be perfect at. Even when you think you've done everything right, not everyone else is going to feel like it was fair and it was perfect. But I really try hard to over- deliver on all of our promises to have at least me be able to say to myself in good faith, " I didn't shortchange anybody. I gave them more than I said I was going to. They got a little extra severance, they got a little extra support, they got a little extra vesting, I gave them extra help." And that's my goal. Like I said, I know I'm not going to be perfect at it, not everyone's going to feel that way, but I really want, my goal is everyone's going to leave feeling that way.

Matt Blumberg: Yeah. All right, so let's jump to what you're doing now and what you've been doing for a long time now, Capital Factory. How did you get from multi- time entrepreneur who liked bootstrapping to being the most active investor in Texas?

Josh Baer: Yeah, that was also really organic. Part of it was that Texas grew around me, Texas was, it was easy to be the expert in email when nobody cared about email. It was easy to be the most active investor in Texas when there weren't that many investors in Texas. And that was really where it started. I was like one of a dozen angel investors in Austin. So I was the most active one because I did five deals.

Matt Blumberg: But your DNA, you were wired to not go after investment. Beyond that, the treadmill that so many founders are on of next financing, next financing, next financing, and now you're on the other side of that that you were never on as the entrepreneur.

Josh Baer: Yeah, it is interesting. I mean, I have raised funding for Otherinbox and for different things and I raised funds now that we go invest, but I am a bootstrap real hard. I do kind of come at it from a scrappy like, " How do I just go do this myself or can I fund it myself?" I'd prefer to just go faster that way. But deep down, I do, as you know about this about me, I love entrepreneurs. They're my people. I love talking to entrepreneurs. I get super excited about what they're working on and what they're doing and I love connecting them together. I get a lot of personal satisfaction out of that. And so it's kind of like there's very few people that can be the CEO of more than one company. Elon Musk is quite the exception, but there's a few others. Most people, you get to do one, you get to have one thing that you're in charge of. And if you want to be involved in other company is really kind of table stakes is to be an investor. That's one of the main ways you get to be involved, have a seat at the table, be part of the conversation. And that was exciting and interesting and fun. And at the beginning, I didn't really know what I was doing at all. Now I feel like we've learned a lot and I feel like we know a little bit more, but really that is what it was about. It was about how do I connect with all these different people? And if you want to have a seat at the table to be able to know who to make the introductions to or to be part of the strategy conversations or to do things like that, then being an investor is kind of the way you get that seat at the table.

Matt Blumberg: Yeah. And how many companies has Capital Factory invested in or how many have gone through the program or whatever the language you use to describe it?

Josh Baer: Yeah, we work with so many different people in different ways and there's a lot of free things that happen at Capital Factory and other people that put on programs at Capital Factory, so thousands and thousands of companies have touched it in different ways. But the way I would think about that question is how many companies are we on the cap table of, do we own shares in? And that's approaching around 800.

Matt Blumberg: That's a big number. That is a really big, and all 800 for the most part are made in Texas?

Josh Baer: Yeah. I mean, that was the intent. We add about 10 or 12 a month and these days, one or two of those aren't from Texas because of all the government stuff. So for example, just the other day a doctor flew in from Boston and with a software and diagnosis solution to help make sure that the right drugs get prescribed for anxiety and PTSD, and depression disorders, which can be really difficult. And it kind of blows my mind that people are coming in from around the country or that some grown technologies coming in from California, but our focus really is on Texas. That's where we can be the most helpful. And the reason those people are coming in is because they want to plug into all the growth and energy of what's going on in Texas.

Matt Blumberg: Yeah, no, it's a great ecosystem there for sure. All right, so last question. Of everything in your career that we didn't talk about today, what has been the most either interesting or unique or impactful experience you've had? So I'm looking at Aspen Institute fellow, Eisenhower fellow, you founded some stuff in Austin, you are an investor in a wine bar. So many interesting things over the years. What's one that kind of stands out when you think about your career as an entrepreneur that really contributed in ways that maybe the average entrepreneur isn't going to have access to?

Josh Baer: I'm a big fan of saying that luck is when preparation meets opportunity. And so you can work really hard to try to get lucky, but really early on we were lucky just line up that we were at the right place at the right time for President Obama to come visit when he came to Austin and while he was in office. And that was something that was, since then I've had a lot of really important people come through and kings and queens and other, we've had CEOs of Apple and Microsoft and others. It's hard to beat the president, but just a lot of really important people come through. And yet, that was actually the first big visit that we had. And it was incredible to see as the most extreme example of it, the true power of the bully pulpit, of the power of standing next to the president, of him saying anything, of you saying, there was a moment where I was in a room with maybe 20 or 30 people and I'm kind of like saying something and he's standing next to me. And I realized after the fact, whatever I had said, as long as he didn't disagree with me, I had the endorsement of the president. You know what I mean? Suddenly it had a lot of power. And it was amazing just to see how much gravitas really comes with that. And that being, it happens to everybody in different roles and you see how everybody's view is different. As a CEO, that's such a big challenge is how do you know what's really going on? How do you get the real deal from people, from your employees, from your customers, from others who don't talk to you the same way they talk to everybody else. With the president, he literally doesn't even see the real world. Imagine he's walking down a hallway and just around the corner in front of him, people are painting the walls as fast as they can to repaint them and make them bright white for him as he comes down the hallway. That's the kind of environment he lives in. Everything is staged and set up and built out. So anyway, that was a super unique experience that taught me a lot about one, it really helped elevate and launch Capital Factory and it really just taught me a lot about the power of leadership and of the significance that you can have in a role like that.

Matt Blumberg: Yeah. All right. Well, that's a great moment to end on. Josh, thank you for sharing your story. You are truly like the founder's founder, the entrepreneur's entrepreneur, and I'm proud to say that you and I worked together kind of mid- career for both of us, and it's been so much fun watching the empire that you've built continue to grow. So thank you very much.

Josh Baer: I'm so glad to be here, Matt. It's great to see you.


Today on The Daily Bolster, Matt welcomes Josh Baer, the founder of Capital Factory, the largest active early-stage investor in Texas. Josh shares about starting Capital Factory, his love for entrepreneurs, and chasing opportunity. 

They also chat about his career, which began as a founder in a college dorm room (or, depending on your definition, as a grocery store bagger). Tune in to hear Josh’s perspective on becoming an early email expert, handling acquisition as a CEO, and more.