SmartMoney Ventures Podcast

SMV12: Ry Walker: From College Dropout to Unicorn Success in Cincinnati Ohio.

Jeff (J.D.) Davids

In this episode of the SmartMoney Ventures Podcast, Ry Walker tells the story of his entrepreneurial journey from college dropout to Unicorn success in Cincinnati, Ohio. 

In this episode, you will learn:

  1. How to build Unicorn software companies in Cincinnati Ohio.
  2. Why the entrepreneur’s journey is like mountain climbing, where you value the climb more than the peak itself.  
  3. How Astronomer & Tembo are commercializing open source platforms and challenging software giants like Oracle and Snowflake.  
  4. What NBA Legend LeBron James and startup CEOs have in common.
  5. Why we learn more from failure than we do from success.
  6. Advice for tech entrepreneurs:  Visit San Francisco, build confidence, pursue speed.  

Ry Walker is one of those rare entrepreneurs who sees trends before most other people do.  After dropping out of college at the University of Cincinnati, he got hired to build and deliver IBM clone computers and teach people how to use early PC software tools. 

Then he founded his first company, SharkBytes, building websites in 1995 in downtown Cincinnati.  He and his brother went to businesses, unplugged their fax machines and showed people the internet, trying to sell them websites, many times being told to plug the fax machine back in. Failure is part of the process, but getting back up is essential.  

They built SharkBytes to 30 employees and sold it to a rollup in 1999.  He was a paper millionaire at 27 years old, only to watch it go up in flames in the “dot-bomb” of 2000/2001.  

Fast forward to 2015, when he founded Astronomer, a software company that has raised over $280M of venture capital and is valued at over $1 Billion.  He describes Astronomer as a pipeline for data, built on top of Apache Airflow, a Python based open-source workflow management platform.  Ry served as CEO for 4 years, CTO for 2 more years, and left to start another company and become an investor.  

In November of 2022, he founded Tembo, a developer platform built on top of PostGres, an open-source relational database management system.  Coming strong out of the gate, he raised a $7 Million dollar seed round led by Venrock with CincyTech, Cintrifuse Capital, Fireroad, Grand Ventures and Wireframe Ventures participating.  Ry believes that commercial platforms built on top of open-source software is the future, and is a founding principle for both Astronomer and Tembo.  

Ry has been recognized as a Cincinnati “Top 40 Under 40” and is an AngelPad alum. He loves nature, science, art, sports, and indie game development.  

I know that you’ll enjoy hearing Ry share his story of entrepreneurship and all the wisdom that he’s learned along the way.  Enjoy!

Speaker 2:

Welcome to the Smart Money Ventures podcast, where we highlight active leaders in the global ecosystem of venture capital, entrepreneurship and innovation. We give you access to insights from successful investors and entrepreneurs that most people just can't get access to, and the only reason they take our calls is because we've been in the trenches with them for decades. My name's JD Davidson and I'm your host for this episode of the Smart Money Ventures podcast, and today we have a very special guest that I have great respect for. Rawakar is a software engineer, founder and an advocate for open-source software.

Speaker 2:

He co-founded one of the first technology unicorns in Cincinnati called Astronomer, and also differential, which is a venture studio. His latest company is Tembo, a developer platform for building data services, and they're taking on tech giants like Oracle and Snowflake. He's currently a partner at Fire Road Ventures, a holding company that invests in early-stage tech companies. He previously served in executive roles at Recruit Military, the Divine Group, and he was the founder and CEO of his first company, sharkbites. He's been recognized as a Cincinnati top 40 under 40 and an Angel Pad alumni, and he loves nature, science, art, sports and indie game development. Welcome, ryan. Thanks for joining us today.

Speaker 3:

Thanks for inviting me. I'm excited to be here.

Speaker 2:

Excellent. Let's start with the story of how you came to start your very first company, sharkbites. What was the catalyst or the idea that got it going and what were the early days? Like Launching a new business, particularly as a first-time founder.

Speaker 3:

Yeah, I'm a little embarrassed about the name, but I was in my 20s. Whatever Sharks were cool. Sure.

Speaker 3:

But now that one. I dropped out of the University of Cincinnati after a year and a half in computer science, mostly because it was still stuck in mainframe land and I had already moved on, before even starting college, to PC and software development on computers, on personal computers. I actually dropped out of college. I did manual labor jobs for a short period of time but then got hired by a clone shop. I don't remember when people used to build clones, ibm clones, and it was a big business making computers, literally putting them together and selling to people down in. I was out of Ohio for one year. I was in Naples, florida.

Speaker 2:

It kind of got me.

Speaker 3:

It sucked me back into tech, into just paying attention to computers. I actually started a computer training company. But then 1994, the web browser this is kind of fun I'm showing people. My job at this clone shop was deliver computers and help these old people with whatever they need to get set up, whatever software they're trying to install. I got to see such a wide variety of software at a young age that normally you wouldn't see. Right around that time the internet was starting. There were bulletin boards. If you remember that era, we were all getting networked, basically.

Speaker 3:

I just basically jumped into web design before style sheets existed. I was building websites before style sheets when Mosaic was the browser. We had an office downtown in 1995 and we just walked literally super. I didn't come for money or anything, so we were in this little apartment just walking around downtown, my brother and I unplugging people's fax machines and showing them the internet and asking if they wanted to buy a website and they'd be like please plug my fax machine back in. That was a tough sale. We ended up growing that company to 30 people, merging it into a roll up company in 1999 and watched it all go up in flames in 2001. Unfortunately, I did go out west coast and we tried to participate in the US web merger but didn't get selected in that craziness. I don't even know if that ended up.

Speaker 2:

The people who sold their interactive agencies made money on that deal, but probably not it's funny that whole thing is a trip in the way back machine for me because in late 1995 I moved to San Francisco and joined Organic Online and definitely bumped into US web and CKS Even actually a long time ago. During that era I actually had a meeting with Mark Kwame. He would obviously not remember it and it was a single meeting, but it was just fascinating. That's the era when Mark Andreessen was coming out of University of Illinois, champaign, urbana. Good things come from the Midwest.

Speaker 3:

The Netscape stuff was crazy. Netscape server came out. I mean we had a little server closet at the company where we had a T1 coming in which cost us three grand a month to have a T1, and we were hosting websites for big companies at our closet on 7th Street downtown Cincinnati. It was crazy with really bad software too. I don't know if you remember Internet IIS early version. Such a horrible web server is so hard to manage and see what's going on, but whatever, yeah, that was a fun time. I learned a lot. I basically was a paper millionaire at age 27 but got depapered shortly thereafter.

Speaker 2:

As many of us did, absolutely no question that experience. What was the one key takeaway that you learned that you wish all first time CEOs knew?

Speaker 3:

Well, basically the experience that I got in the process, the thing I'm starting to learn, people are asking me why am I doing Tembo now If I had a pretty good exit with Astronomer Like a lot?

Speaker 2:

of people, congratulations.

Speaker 3:

Yeah, so I sold shares at the top of the market in secondary sales. Really, I don't have to work if I don't want to. I've got that level of wealth now, which is just insane, because two or three years prior I had $50,000 in credit card debt typical startup founder finance. But I started another one because it's really about the journey of mountain climbing. I enjoy mountain climbing in terms of building companies, trying to build products. If you make it to the top of a hill, how long do you stay? You take some pictures, you stay on there for a few minutes and then you're walking back down and it's the journey, it's not the destination. I learned so much. I had negotiated selling a company. I had to hire people, I had to pull together payroll $150,000 of payroll every two weeks that was hard Cash receive. I just think it doesn't even matter how successful your first business is, as long as you're learning lessons, learning how business works. It's actually, again, it's nice to have money too, but the experience is rocket fuel for future profits, I suppose.

Speaker 2:

I believe that every failure has a learning opportunity in it and, at the end of the day, nothing is actually wasted Right.

Speaker 3:

I mean, really you learn more through failure than success. To be frank, I love sales calls where someone tells me this is a stupid idea. That's the perspective that I probably need to hear, because if I just go and come up with a product and, first of all, you don't sell 100 out of 100. Your first 100 meetings you're going to get a lot of rejection. But that rejection is what feels improvement.

Speaker 2:

Absolutely Well. Failure is a prerequisite to success.

Speaker 3:

Yeah, I watch NBA. I watch the Lakers. I watched every Lakers game this season that's been on TV. I just love watching professional NBA, which almost nobody in the world loves anymore. Again, it's so interesting. You get to the pinnacle of those are like the best VCs or the best founders operating. They can't get any better. They're all pretty evenly matched and they lose half the time approximately by rule. It's like that's just what life is. It's grind. And why is LeBron still playing 20 years in? Because he likes playing basketball. I just think that's. It's kind of fun to watch. I watch golf too, and same deal there. Those guys that can be so amazingly good at golf and they come in 50th Right. It's so humbling, but I just think that's. We all expect the life to be like a movie or a TV show, but it was way more grindy than that.

Speaker 2:

Absolutely. Yeah, you're going to have successes and failures, you're going to get knocked down, but the point is you got to get back up. I like your basketball analogy, because even players at the top of their game making millions of dollars, what is their free throw shooting percentage?

Speaker 3:

Yeah, I mean, they throw the ball out of bounds with no one there sometimes, right, yeah, like that's just true of everybody, like CEOs make CEOs do that. They turn and throw the ball to nobody and the coach catches it like what the hell was that? Right, you know, it's just like mistakes are just part for the course and I just think it's great to acknowledge that. In business, I mean, I think a lot of people try to act and behave as if they're perfect, and I'm just. I'm pretty opposite of that. I'm very easy to change my mind on things. If you have an argument, that's better than my preconceived notion on something. But at the same time, I'm always pushing my team to have better ideas and if my ideas are better than theirs, adopt it. Right, give and take.

Speaker 2:

Well, I think that's why it's important that business is a team sport, because if you have one person in a company I'm sure you've seen this right If you have one person in a company that believes that they're the smartest person in the room, that'll kill a company.

Speaker 3:

Oh, yeah, yeah, no one wants to be around that person. I literally, you know, in this newest company, I'm just like telling my executive team like you guys better get along, you better solve problems together. I am not your daddy, I'm not going to like, I'm not going to like, I'm not going to basically be the judge and jury when you guys can't agree. If you can't agree, like you can't have this job. You know, and that's just the way it's going to be. And you know I have to make sure I find people who are compatible in that regard, absolutely. But if they're not, if they're not doing, if they're not getting along, if they're not executing, it's like, it's just, you know, trade them out. You know, again, like once again, right back to the NBA analogy you know a player can be really good on one team and you put them on another team. The chemistry is wrong and you know they can't perform. So it's nothing that they're not a bad player, they just got. They're just on the wrong team at the wrong time. You know, just trade them.

Speaker 2:

You know Exactly. Well, it's like putting together the pieces of a puzzle. You try a bunch of pieces. Not all of them fit, and it's okay. It doesn't mean it's a bad piece, it just means it doesn't fit for this particular place. Yeah, that's for sure. Yes. Well, let's talk a little bit about astronomer. Everybody likes to talk about unicorns. First, explain just a little bit about Apache Airflow in layman's term Terms and how astronomer enables that.

Speaker 3:

Yeah, when we first started it, I felt like I couldn't explain it to anybody, and by nowadays, I think everyone can understand data. I would say, like data pipelines. I like challenging people. They say, hey, what do you do? I mean you could just say like, oh, I'm in data, you know, and just like avoid that. But I'm like this is an opportunity to educate. You know you ask the question, you're going to get an answer.

Speaker 3:

So I talk about, you know, oil is oil needs a pipeline to get from, you know, like an oil field to a refinery, and data needs pipelines to get from Wherever it's being generated to a place to do make some, you know, turn it into something more refined, information or insights, or action. So you know, basically, if you thought, if you think about, like sources and destinations of data, there's little arrows. You draw in between them, and that's what we did. We did the arrows, you know so, with the number of SAS companies and databases, and you know there's so much that we've been abundance and embarrassment of riches.

Speaker 3:

You know, with technology right now, there's so many great tools in every field, you know, and the problem, though, is, if you use lots of different point solutions, you have lots of islands of data, and so air flow, which is the open-source technology we were commercializing, it's just a tool that you can use to Move that data, transform it along the way and make sure that the deliveries are happening, which is really the most important part of it and if and if the deliveries have been, you know, stopped, it actually kind of queues up the work. So if you, once you fix the problem, it'll, you know, replete, you know, continue pushing the data. So you know old-school ideas. You try to push the data. If it fails, it's lost and that's a really bad system, you know.

Speaker 3:

If 99% of your data is making its way through and you don't have good track of what's the 1% that failed. That's a that's a huge mess. That's what we call. You know that's like dirty data. You know so and you know, basically, we're coming into a world where clean data is more important than ever with AI, and you know opportunities to To syndicate data, in some cases, to partners. You know it's pretty embarrassing. It's almost unworkable to have dirty data. So we're just helping companies have great data hygiene and really put their data to work. I always think of it about it like Spinning lots of plates. You know, like, yeah, you've seen someone who, like spin like 20 plates in front of them. That's what air flows doing, versus having the plates, you know up in your cabinet, which is what a database might do is, like you know, store it nicely and securely, right. You know we basically helped people put their data out to work for them, and I think that that's Really important in today's age.

Speaker 2:

I'm glad you learned. I'm glad that you use the term data hygiene, because I think we need to talk about it more and I think that most people can understand it. If we use the illustration of a spreadsheet, you know Garbage in, garbage out if you have good data in your spreadsheet, but in the data world it's like spreadsheet on steroids. Yeah.

Speaker 3:

I mean, they're just the same thing as a spread at the table of table of information and yeah, and you know, if you've ever tried to like, you know, let's say you're trying to come up with your monthly budget on a spreadsheet and you're missing rows. It's kind of a pointless exercise, right?

Speaker 2:

You know, because it's not actually, it's a make.

Speaker 3:

You got to make sure all the rows are there before you can complete the task, and Imagine if you're talking about a million rows, you know, instead of 20. That's exactly yeah. So yeah, and and the other thing that's interesting is and this is where kind of airflow started picking up a ton is there's I call it analytics as a feature. A lot of software now has charts and you know, like Analytics inside the product, and that means you kind of have to do this fast loop of user. You know. You know, let's say, it's a fidelity comm like 20 years ago. You get a financial statement in the mail or something like that. You would.

Speaker 3:

You didn't get like live Dashboards on how are you performing up to that minute, and that's. That's the kind of stuff that just requires a pretty nice data engine to Produce that. Again, you don't want it to be wrong. You know you don't want it to miss a transaction. You're, you're gonna get fired a few if you're, if you show the user wrong data. So it's the pressure's gone up a bunch. Yeah, ai hadn't really emerged too much. Now, of course, airflow is. You know this. The role came out called a ML engineer. You know, machine learning engineer and, and you know, the AI use case Is just amping it all up even even higher.

Speaker 2:

So AI is obviously massively shifting markets and it used to take a long time and a lot of money to get to a billion dollar company, but today you can use technology to really leapfrog and just capture a market share in ways that it wasn't possible ten or twenty years ago. Talk a little bit about that.

Speaker 3:

Yeah, well, I mean, everything's gonna get disrupted, as you know. I mean, just think about, like brick-and-mortar to eat, to e-commerce, like that same revolution that was about to happen. Regarding AI, or, you know, mobile was another big revolution. You know that lots of things got disrupted when mobile, you know, became possible. But I mean, the thing about AI is like it's still kind of raw. It's a tool, you know, like the internet is, and it's gonna disrupt People who don't take advantage of it, and so it's kind of like I do think that there could be a, there'll be a bubble coming, you know, I think in this decade around.

Speaker 3:

AI you know, the same way there was with the internet bubble back in the 90s. You know, because, oh yeah, I mean I, it's already started. I mean, the VCs are, all you know, they're investing, you know, double triple, you know, but they're basically investing in multiple of the same companies in some cases just to make sure they win the bet, not not lose. But yeah, but luckily, I would say, from a Hype standpoint, there are other factors that have made this cycle, you know, tampered down a little bit, which is, I think, it's actually really good, because if we would have kept the same hype that was going VC and AI hit, it would have definitely been a problematic bubble, you know, yeah, fun flows and there's almost a business cycle to venture in, even, you know, comparable to the old business cycle that they talked About.

Speaker 2:

Vcs tend to overfund sectors, too many competitors and then eventually valuations get too high. They're putting too much in companies and a couple of them fold and then everything right sizes. But, as you know, in a down market that's the best time to start a company.

Speaker 3:

Yeah, it really is. I think I mean there's there's pros and cons to it. I think that I get like long term, it's just it's. It's like it's is it better to? I don't know? I would say like, is it better to go Find food? Let's say you're going to a food court. It's better to go to a food court. It has lots of restaurants and no lines or, you know, it's just like lots of workers.

Speaker 3:

That's kind of like the VC of 2022 or 2021 or do you want them to have them to be shut down and the workers are kind of cut. It's like I still think it's like it's easier to get food, you know, when everything is like hypes, you know, and you know I'm full. But yeah, I think you know You're probably gonna get. If you think about like the ones that are shut down or the ones that work weren't great, you know. So it's, it's like you're, the odds of getting a good meal are higher, I would say, and that in that down Environment, because only the best restaurants would have survived whatever cycle caused it to decline like that. So, but you know, I think that there's pros and cons to both, both cycles.

Speaker 2:

It's really fun to be in the in the up, you know, cycle to you know, especially if you have shares of something that are Increasing so absolutely, and you have to know when to harvest, to yep.

Speaker 3:

Yeah, well, it was really easy for me. I just, I just had basically had a thought experiment of if I was at a casino, you know, and I had this many chips on the table, would I leave the casino? At this moment, you know, it's like, it's like absolutely yes, well, what's the difference, you know? Yep, if you can sell your shares, you know, and you have almost no money, you know, and you could sell millions of dollars worth of shares, you know, like I don't know, I just think it's crazy, did not take that opportunity.

Speaker 2:

I agree, I agree. So let's talk about investors and raising money. How did you first connect with? You know some of the? I mean your seed, rounded astronomer, was 12.7 million dollars and you had what? 16 plus investors in that it since he tech refinery, sierra Bain, angel, pad, 500, global. Then you went into, you went on to get Fenrock to lead the a, sierra led the B, inside partners and JP Morgan came in and series C. How did Developers in Cincinnati like yourself first get connected with those coastal investors?

Speaker 3:

Yeah, it was subtle, it was Sutter Hill, by the way, that's the B. But yeah, I think you said you said Sierra on that. But yeah, yeah, how do we get? I mean, the thing I always tell founders is, if you're getting ready to do a tech startup venture, back tech startup, go to San Francisco a couple times for a couple of weeks and Build a network, meet people you know, find out if, if your idea is DOA, you know dead on arrival, like it's, it probably is. That's like like, like you know you're naive Midwest idea is probably already dead. You just don't know it yet. Maybe you could again now. Again is as far as a return on your investment.

Speaker 3:

However I was, I still say like again, the mission is learning, the journey is about learning and if you can afford to, you know, just expect. I mean it's kind of cool like you can raise a little bit of money from Midwest VCs, pay yourself enough money to survive and and like, bang your head against an unsolvable problem for a couple years, like You're gonna learn a lot. You know you're not gonna feel very good about yourself and you're gonna think you did something wrong, but it was just like you're paying again. It's like, imagine if I go and try to train it with the Lakers and then I try to play a pickup came with them. I'm gonna get my ass kicked. You know, like, like crazy, it's almost on. It's almost almost the point where it's unvaluable. You know like, I'm not really gonna learn a ton playing against a pro basketball team, but You're gonna learn a little bit, you're gonna. You know, you're gonna be humbled for sure If that, if you needed some of that, I guess you get some of that.

Speaker 3:

But so that's why I say like, especially young people, if they're 20, like I'm like, just do any startup, doesn't matter, because it's gonna, it's gonna fail anyway, His products not gonna work, you know. So, right, rather than like wait for the perfect opportunity, just try to build something I built. I tried to build 30 things in my life. I seriously I could probably come down with a list of products that I've started writing code for and Didn't profit from 30 times at least. At least you know I actually started building the same game five different times. You know, like every two years I'm like, you know, I want to start that and it's like I get to a point I quit and then two years later I start again. You know it's just like it's again, it's not really about for that one. You know I would have what I love to be a world-class game designer. In addition, everything else I'm doing, sure, but like it's not very practical, I don't put the time in for that. You know so sure.

Speaker 2:

But it's a lot of creative experimentation and I think that's that's what's important there's. There's a real mindset you kind of touched on. You know I'm gonna do a series on entrepreneurial psychology. Yeah, and to your point, when you're in that first startup and everything is failing, Then it is hard to have positive self-esteem and you and you need a sort of supportive community of people around you To be able to get back up when you get knocked down. Yeah, it's funny.

Speaker 3:

Like there's a lot of supportive people in the Midwest and Cincinnati, a lot of organizations that are gonna hold your hand and make, try to Make you feel as good as possible. So I've actually taken the role of the, of the, of the, the opposite of that. You know, I want to be the guy who was gonna give you the hard truth, you know, and just bring a little Silicon Valley like slap to you. You know, like you know, cuz I just we don't have enough of it here. So, you know, I just talk. I talked to people all the time.

Speaker 3:

I'm like I don't, it doesn't, almost doesn't matter who they are. They're not confident enough and they're not moving fast enough in the, in the Midwest, like they are not either of those things. It is so especially, you know, to Silicon Valley standards and and maybe they can't get there. But if they could, if they could behave that way, like they have a shot, you know, like at winning actually, like actually winning the business Competition that they've decided to enter, you know, which is right, global competition, you know, but yeah, I mean it's it's hard to just tell someone that and then they'll do it, but I mean I just say, like Speed and confidence are are so, so critical in this space. Yeah, and I think there there is a A start of an ecosystem in Ohio.

Speaker 2:

I think you know the high third frontier program is really well known. You know it's, it's very rare, it's wonderful and at the same time there's still a ton of work to be done.

Speaker 3:

Yeah, I'm again. I think we're doing great. But you know I also, you know, whenever I hear something like, oh, the investors In this town suck, you know Whatever in Ohio the investors aren't great. Like, how are the founders? You know, like I just point my finger at the Founders and like you guys are the problem, not the investors. The money will come. There's great startups here. The money's, the money is just like it's. Those guys have their finger on the wire button. You know the good BC's. They want, they want to invest in good companies. They're, you know, but you're not it. You haven't. You know you got to, got to get there.

Speaker 3:

So, Exactly Well, everybody wants to see you know, revenue traction customer traction and that's what's really important.

Speaker 2:

And you know you're not going to be able to get there. And even in California we can't repeat that enough To young founders. You know it's all about demonstrating that a customer loves your product. It's not a matter of whether the investor loves the product right.

Speaker 3:

Yeah, yeah, I agree, and there's lots of different forms of showing that traction. You know, for example, like tembo, or my newest company, we, we just got to revenue two or three weeks ago, so I only have a handful of paying customers and that's not very impressive and you really shouldn't lead with that and an investor pitch. But you know, when I show the logos of the companies that have signed up for us already, um, that we hate but that we need to go, mine, you know, like signups or not, um, you know, again, it's really hard to get people's attention and interest and your product. Just because they sign up doesn't mean they're, they're on the, they've been hooked and they're in the boat. You know, all it really means is they've, they've nibbled, you know, and like you have to go still get them.

Speaker 3:

A lot, a lot of cases, um, you know. So I can just show a slide. You know I've had 800 signups for this new product and here are some of the logos of people who've signed up and it looks pretty damn impressive. It'd be better if those were my customers, but they're at least I have that. You know, that level of um interest and you know that's it's pretty easy to. It's a little bit of a hack you can do to have a great logo slide without it being uh, you know, paying customers. You got to do that kind of stuff.

Speaker 2:

Absolutely, absolutely customer engagement, but the quality of the customer as well. You know, get the right customers, not just any customers.

Speaker 3:

Yeah, yeah, it's the worst thing in the world. Be like, oh yeah, we, you know Crushing it with, you know ABC plumbing and like they're, they love our product. And then you know, like you know, there's a nursing home, that's just like totally into postgrass. We're rocking them like he just lost that pitch. You know, right, exactly exactly.

Speaker 2:

Well, that's a great pivot into the Tenbo story. So you tell again layman's explanation of postgrass as a database and a data service that you're yeah so.

Speaker 3:

So, you know, in the course of doing astronomer again, I recognize, like I call it, the modern data sprawl. Um, you know, there's like Um data is. You know all you know, a company's data is being sliced into more and more piles. You know, again, that volume of data you have is obviously growing exponentially, but the number of piles that it lives in is also growing, maybe not exponentially, but you know, at least linearly. You know. So, um, the more, the more of these data islands you have, um, I just think it's like a, it's a, it's a kind of a, a small negative Um, it's better to have the data in an island than not to have it at all. That's for sure you know.

Speaker 3:

But, um, you know, postgrass is a really old open source technology, 30 years old. Um, it's got, you know, it's very well established in and, uh, I call it like transactional use cases. You know, when you're just um, you know putting a database behind an application or whatever. But, um, it's also very extendable and in recent years there have been a lots of cool new extensions. You can now write extensions and rust, which is a really hot new programming language, um, kind of the most beloved programming language right now, and so it's extendable, and in recent years it's been well extended. And the problem is like, if you're a postgres user, uh, you kind of have this feeling like I'm not using the whole product now, but, um, no one has done a good job of packaging up all those, um, extended capabilities into a commercial product. It's really you have to be kind of a risky nerd, you know, to take advantage of some of these things and not everybody's risky and not everybody's a nerd.

Speaker 3:

You know they can install their own extension and defend that decision, you know. So we want to basically give the postgres ecosystem um A sales rep in the room when, when you're considering like snowflake as a data warehouse, I want to have our rep in there saying Eh postgres can actually probably handle this pretty well.

Speaker 3:

And here's the, here's the benchmark and here's the total cost of ownership. If you want to put to snowflake, snowflake's gonna hate that shit. But you know, like. But basically postgres in most cases does not have Sales representation. And I always talk about, like, the reason why there are so many I mean the reason why companies have bought so many vendors is because there's so many great sales reps. Like the sales reps are in many ways, like, greater than the buyer.

Speaker 3:

You know, in terms of it, yeah, you can't really, you can't really defend yourself from snowflake. You know, like they were, they're going to penetrate accounts, they're going to land, they're going to expand. They have trained hundreds. You know world class people that do this, and so it's not your fault, you have 100 different data tools. But I want to fight. I basically want to fight against that, that current. You know, and see, see what happens. So that's the main idea with with tempo, and then we can also give you kind of a, because Postgres has this cool thing called replication. So if you have many data islands former data islands now they're all connected, they can be automatically connected because Postgres databases can easily send data to and from other databases, so you can kind of skip the pipeline. At least I would say you can skip 10,. You know, like a 90, 90% of the pain that you would have, maybe even 99% of the pain that you would have had building these data pipelines between systems if, if it's Postgres to Postgres.

Speaker 3:

So I hope that makes sense, but it's amazing.

Speaker 2:

The question I do have in both astronomers case and tempo is that they're based on a flat, a fundamental platform of open source software, but yet you build a commercial enterprise around an open source software platform. Tell us about that.

Speaker 3:

It's the future of software. I mean, I think that there's not going to be any domain of software that doesn't have open core. You know that it's just a better model, for many reasons, you know. Think of, like video games, you know, again, I like, I'm like an indie game developer, but there are these game engines that give you incredible capabilities that didn't exist 20 years ago. You had to write the game from scratch, you know like. You know like now you have a physics engine, you have a, you know, 3d rendering engine, you have all this stuff that just it's like, it's like a magic canvas. You know to build things. It's the same thing, you know, and so it used to be.

Speaker 3:

A lot of some of these game engines were commercial and cost money, but that's all changed too, now. Now, if you want to use unity or, or you know these, these, these great tools, they're basically either open source or completely free like. Completely free is, like you know, for low usage, is is on the path to open source. But you know, there's an open source game development engines, my favorite engine, and it's it's like it's a forever engine. It's not going anywhere, it's it's you know, they're not going to, there's not going to be anyone like changing the rules in the middle of the game, hopefully.

Speaker 3:

You know there's always some shenanigans that can happen with open source, but I just think it's the most solid foundation. A user, you know, basically a consumer of the tech, whether it's the person writing the game or the person using the game, you know, buying the game it's just a better foundation than commercial products that could be canceled at any time. You know, like if, if you sold, if I sold Tempo to Amazon, you know, and I, you know we decided to shut down the product. All the open source tech that we built doesn't get destroyed in that process, you know. And so I think I think it's great for the again, it's great for the world for the important core parts to be forever, you know not, and not like at the whim of some executive to kill it, you know.

Speaker 2:

What I like about that is that your priority is serving the customer.

Speaker 3:

Yeah.

Speaker 2:

Mike, over the long term, doing the right thing for the customer.

Speaker 3:

Yeah, I talk about a time, like you know, the great thing about Tempo is we're investing money in the Postgres ecosystem and whether or not we succeed as a company, Postgres will be better off. That makes me feel good, you know, because I think it's a great technology. Of course, I want to build a great, successful company, but we're improving the world. You know, again, it's like a. It's not like we're improving like carbon capture, you know, like we're not fixing global warming, you know, but we are trying to make databases and the world of databases better than it was when we, you know, when we came on the scene.

Speaker 2:

So that's an enabling technology for so many things. I mean every medical device and life science company uses databases to do the work that they do, so it's fundamental, yeah, I agree, yeah, I mean, yeah, it's definitely it's.

Speaker 3:

Yeah, it's like a pickaxe, you know, or a screwdriver you can use it for lots of different things, absolutely.

Speaker 2:

So let's talk a little bit about your transition to becoming an investor at Fire Road Ventures, and I know that you've always kind of been an investor because you're investing time and resources into projects. But now it's different when you're writing checks. Talk about that transition, yeah.

Speaker 3:

I mean, for me it's it's, you know. So now you have, if you have a little money, what are you going to do with it? You know you could give it away. You know you could just be charitable, you could hoard it. You know, like, these are some of your options.

Speaker 3:

I like the idea of I mean basically after I, after I really feel like most founders feel this way too. If you have some success, it's like you got lucky. Yeah, you know, obviously you did a lot of things to put yourself in a good position to get lucky, but still you got. You got a good role of a die. You know I got some good dice rolls and my thought is I want to help 20 other. You know entrepreneurs make it through the gauntlet. That I just made it through and if I, you know, like using my money to help do that is, it seems like a good. Again, it's a social good. You know it's not necessarily for everybody, but there are founders that are challenged in this ecosystem and if I can help them get through it, you know like I just feel like that's a good karma thing to do, and in fun, you know, too, it's fun to see people win. You know that you're helping.

Speaker 3:

So that was my idea there and so I started something called Cincinnati Ventures, which didn't last very long because teamed up with my friend, tim Metzner shortly after I started that. But yeah, I just I just wanted to help entrepreneurs and you know it's investing as an angel is kind of a it's hard. Well, I'm not the most organized person in the world, so it's not I can make really fast decisions, which aren't. You know. It's nice to have, like, basically, some people around the table that are going to do a little diligence and spend more time comparing this versus that and so on. I like that teaming up with Tim and Christie Christie Johnson and some of the others in the firm now and just kind of building into that is, in a sense, like Tim's one of those guys that I'm trying to help. You know he's not far behind me but you know, like you know he deserves to win just as much as I. He's put in as much effort as I have, and you know I'm going to try to help him get where he needs to go.

Speaker 2:

Absolutely. Tim and Christie are great people, and I think that's also a big part of what you're doing right is picking the right people and doing so very intentionally and carefully.

Speaker 3:

Yeah, yeah, I think so. I mean it's. Yeah, I'm also pretty. You know I'll generally meet with just about anybody. It's again that's kind of one of the reasons why it's hard to be organized is if you have lots of meetings it's hard to. You know, you don't have time to reorder your desk necessarily, but I'll meet with anybody in our ecosystem at least once and, you know, try to figure out some way to help them doing some of us.

Speaker 3:

I'm doing some fun stuff now with Centrifuse too, which is our Cincinnati startup ecosystem booster organization. They have a little fun now and but we're doing demo nights. So once a month I'd basically saying telling entrepreneurs, come demo, working software in front of everybody, and it's just a really good habit to share your work publicly, especially with people who could be critical of it. You know. So that's right. You know you should demo I also. You know one of the reasons I'm doing this is the best VC pitches are software demos of something amazing. Like that's the best way to get money is like, just show them what you built and if they're wild, you get their money, you know so it's very very rare to have a pitch where they do a great demo.

Speaker 3:

A lot of a lot of talk.

Speaker 2:

you know not as much you know back in the day we used to call it vaporware. Yeah software right. Yeah, it was a bunch of really pretty slides and nothing behind it.

Speaker 3:

Yeah, yeah, I mean, it's so hard to build. You know so hard to build vision. You know, in general too, that's the thing. Like vision is the easiest thing to make. You know like, right, yeah, try to manifest it. You know, hire a developer and get them to do the work. You know it's. And then you know, you realize sometimes like your vision was super flawed. You know, like it's just not as pristine as it is when it's in vision form. You know.

Speaker 2:

Well, when I founded my software company, I used to say that my job was to go out and pitch it to as many people as possible, invite them to shoot holes in it, and then go back to the office and fill the holes with the team.

Speaker 3:

Yeah, yeah, and the way I see it is like it's like discovering the holes, like they don't have to shoot anything. It's already it's already switchies, you know like.

Speaker 2:

It's already evident, right yeah?

Speaker 3:

yeah, like yeah, just tell me where you see holes there are, we know they're present, right?

Speaker 2:

You know it's interesting too.

Speaker 3:

like I actually view software now, as you know how 3D printing. You know like, let's say, you have a body in 3D printing, like the inside is not solid, you know it'll do like a lattice of some sort inside. You know to make it just straight, make it just strong enough to do the job, but not so much to waste material. I think that that's what's happening in software too, like switching back to open source a little bit. A lot of the work we're doing at Tembo and even an astronomer was gluing together open source components and and like I just view that as like uh, it's not as solid as like at least in terms of effort. It feels like we're just like gluing together these lattices of software and it just feels way more lightweight than if I had to have a developer like write that code. That's how that feels like a solid body to me, you know, like in terms of cost and weight and everything. So you know we're just we're able to be like open sources giving us everyone.

Speaker 3:

I mean, when you realize how many open source products go into, I should do a count. You know, like how many different open source projects are gone, have gone into even the Tempo product in a year. It's got to be, it's got to be 500 open source projects and and I'm not kidding about it it's like there's like little libraries you use for building a front end website, you know, and there's, you know, there's just like so many layers. There's a dependency tree you can see in a front end application. You know you include a couple of open source things, they include a bunch of open source things, and you end up with this tree of hundreds of open source projects that are powering even a simple website.

Speaker 2:

Some of those open source projects are so Goliath that, excuse me, some of those open source projects are so Goliath that they really take over. Look at Apache. I mean, what percentage of the web traffic goes over an Apache server? It's hard for me 90 plus percent.

Speaker 3:

Yeah, I mean, someone might actually have the stats on that. But then, like, its competitors are NGINX and other open source product. You know, there's like there's, there's so many web servers If you, if we look at the total number of web servers available versus, and how many of those are commercial, now it's it's like the, the open source is, there's 100 of them for every one commercial open source web or commercial web server. I should say like proprietary, you know, web server. It's just, it's just like there's certain areas where that, that battlefield has already been overrun by open source.

Speaker 3:

And that's why I say like, like, explain to me why any field of open source or any field of software that same fate is is destined, as far as I'm concerned, like, how do you defend proprietary software against the horde, the open source horde? And there is. The answer is like no one's done it yet, no one's really defending that, and it's it's. It's like and I was reading a book about how, you know, fighting in Afghanistan, you know the whole world of war change because there's like not an army, it's not like you can go and there's a battle line. It's it's like intelligence gathering, reacting quickly, and it's really hard to fight a battle when there is no formal definition of who you're fighting, you know so Great.

Speaker 3:

There's no way a commercial software company can can defend themselves against open source because it's it's basically faceless, nameless, very you know weak. It's weak, it starts out very weak. Like you look at a project that's just got born, you're like that is total garbage, like our product has 5000 extra features. But you know it's it's just like this organic process, like you know, like a virus for reproducing your body. Like you can't stop it. It's going to happen, right.

Speaker 2:

Exactly, exactly. If you can't stop it, you might as well enable it with some tools on top.

Speaker 3:

Well, that's what I think. The best companies are going to just go ahead and say let's use open source as our core, and that's what's happening. And many, many, many Amazon. Amazon's gone that way for sure, you know. Most of its new products are not proprietary completely. They're the wrappers of open source.

Speaker 2:

Sure, I attended startup week since, or start since, he started week a couple of months ago and I was really impressed. It was a fantastic event. It seems to me that all of the groups in centrifuge sincey tech, refinery, fire, road sounds like the ecosystem is really gaining a lot of momentum and positive momentum. Talk a little bit about that.

Speaker 3:

Yeah, I think we're when we got started, when this like the ecosystem started about 10 years ago. You know maybe a little more than that, but I don't know if you're. You know the Bradfeld thesis, you know the 20 year thesis and like we're kind of like halfway through. He's revised that, by the way. He said there's always 20 years, it's always a 20 year process. From wherever you are right now, you know. So there's not like you're not, you don't get halfway done, You're just there's a 20 year horizon in front of you at all point, which is true, you know. But you know one of the big principles there is the founder. The founders, entrepreneurs, have to take control of the ecosystem for it to work. And I think we're getting to the point now where that transition is happening. Like we've had these amazing executives from you know, like Kroger and Proctor and Gamble, and you know just big companies involved in centrifuge leadership for a long time. But I think I think it's starting to shift where it's getting more and more towards founders and entrepreneurs having more and more control over that. And the more that happens to me, the more helpful it'll be.

Speaker 3:

I think that you know it's just tricky, Like when you have corporate people leading a startup accelerator type Program and it's funded by another big company. It's really hard, I think, for them not to Figure out a way to like to serve that big co. You know, like it seems like they're paying for it. They should get some value. But as far as I'm concerned, like those big companies always made you know, they always knew is this is an investment in our, in our town. You know, like I don't need you to do anything for me, but so I just think when, when, when the entrepreneurs take over the ecosystem, we're gonna focus on the founders and that actually helps the big co's. That's actually the help they've always wanted and it's that's really starting to happen.

Speaker 3:

Now Centrifuse is committing to do local investments now. So you know, before it was a fund of funds I don't know if you know too much about that, but they, they invested in world-class funds and they made they. You know they had a great first fund as a result, but it was. It was really. You know, it wasn't like they were doling out cash to a lot of Cincinnati startups. They were doing a little bit of that, but not not very much at all, and it was very quiet when they did it. You know like sure.

Speaker 3:

Yeah.

Speaker 2:

Yeah, I had Tim Shigel on the podcast a while back and he was talking about centrifuge and they really did. I like the approach that they took is that they focused on returns and Geography when possible, and I I think it's great to have programs like third frontier because it absolutely provides a Stimulus at the beginning, you know, to overcome inertia. I don't think it's either, or I think it's both.

Speaker 3:

That yeah, no, I agree, like I said, I mean, in the startup week, yeah, I don't really think our entrepreneurs could put on an event like that either. It would be way more raw, you know, it's very polished, you know, and that's. That's the kind of stuff that that team is really, has been really great at, and I completely appreciate it. So, yeah, I agree it's got to be a blend, but I'm just saying, like that, the founder influence is is rising and I think that's gonna take us to the next level.

Speaker 2:

Sure so let's talk briefly about mindset the mindset of people in the heartland of America and the mindset of people on the coasts. Yeah, what needs to happen there?

Speaker 3:

Yeah, I mean I, I remember when we were early astronomer, we had a customer on the West Coast. They needed us to. He's like you're not moving in Silicon Valley time and our team wasn't, and you know, it's kind of like it was really the first time that I realized how different, like you know, there's a lot of people here that Focus on quality, getting it right. You know, like they got there when you get it a on the paper. You know where what we need is a B, be fast. You know, like right instead of an a eventually, and so it's really hard for a lot of people to switch that mindset. And so I mean, I think one way to do it is you just have to, you have to set almost I want to call it like artificial Pressure. You know, um, like real, it should be real pressure. You know, like in my case, like I'm telling our team like here's what we need to raise our Series A, you know, and like here's what I'm promising here. There are all the lies in my slide deck that we need to make true. You know, it's not really a lie, in the sense that you know what I'm pitching is vision and it's just basically unrealized vision, you know, but like that it's, the longer that's not a true statement, is a vision statement. You know that the worst the company fund raises and I just try to keep that pressure on them and you have to.

Speaker 3:

I think it's great to have a CEO. That's just Basically, you know, exposing that reality like that's. It's kind of the main driver. Obviously we gotta get customers but, like you know, a lot of people say all fundraising isn't the goal, it's not a really an achievement. I actually pretty diss, I disagree with that pretty profoundly because you can't fundraise without the result you know it's, without the inputs that are required, you know. So you can't raise our entries and Horowitz Without doing all the right things. You know and and like getting that money from them is a huge accomplishment. It means you accomplish lots of other things in the process, you know yeah so you know, I am yeah, anyway, go ahead.

Speaker 2:

We're gonna say putting gas, putting gas in the tech. I mean, you can't build and execute without resources, and we all know it's about scale.

Speaker 3:

And yet and the reason you take money is Primarily to grow faster than you could without it- oh yeah, yeah, I was just talking to a founder to about boost wrapping versus, you know, raising VC, and I just say like I mean again, 20 years ago the term vulture capitalist was a thing and it was real like there. I mean there were people that are literally I mean they're just like there's little evil terms in the, in the docs that they hand coded, you know, just To get you someday. If you, if you stumble and they get the company, you know effectively and so that's all gone, at least in If you, if you go to a premier investor, even in the Midwest, like they're using standard and CVA docs, you know Like there's just there's not like any of that kind of crap going on and it's. You know I started my when I started track but I had a personal Guarantee on like bank lines and stuff. You know like it was scary to take money. This is the stuff is like it's so founder friendly.

Speaker 3:

I'm like I don't see why you wouldn't just take money from someone who's gonna give you a million bucks. You know if it works, they get some equity, if it doesn't work, no big deal. You got some learning. I don't know it's like funding your education. I just I don't understand why you want the stress of having to not have money during that process you know, not having money for your family like it's just. It's just a.

Speaker 3:

I think there's fear in there and there's like I Think it's like lack of the ambition. There's all kinds of it's confidence too, like I was saying like like they don't have the confidence to try to build a venture scale company. And you know like, yeah, that's that's the downside of all that. But I mean I I'm basically pushing against bootstrap more and more. I mean, not, not everyone has a business they can raise venture capital. But if it's not a venture capital business, that it's probably like an angel investor kind of business. Right, you can find someone, some rich guy in your town like me, that will Happily give you some money for unfair percentage of your company. You know like, and that's it's like, should you do that? Like? I think so, because like it's better to have them in your corner than go it alone. You know, in almost every case, if you're, if you haven't made it before, you know like, just get a, get a lowercase w before you're going for the upper case W absolutely.

Speaker 2:

Yeah, I like that you have to hit some singles before you can get a home run and clearly in your career path you did that. You didn't go out and do a unicorn on your first one, it was like your seventh or something, right.

Speaker 3:

Yeah, yeah, yeah, so it's. It's been a long journey. Yeah, so it's, you know. But again, like the journey's been the, you know, as I said, I'm telling my team we are team in town today and or last this week and I basically said, like guys, you got to understand, like this is like such the good old days right now. This, you know, like that, oh, we're trying to get these features in, try to get so that we can get signups, so that we can get series. A like this is, like this, is it right now. This is the best part of the climb, you know. And, right, you know, it's so fun.

Speaker 3:

Like it kind of gets worse from here. You know, eventually we're gonna hire a, hire a bunch of people. Everything slows down, you know, like Personality conflicts have to happen the more people you get. And like, right now we're kind of in this little pristine, it's still very stressful, but like, dude, we have, we raised seven million dollars. Everyone's getting the money they want. It's not that stressful, you know, compared to yeah, yeah, it's anyway. I just think, like you know, so that's the mindset stuff, you know. I just, I just tell everybody confidence and speed. You can't have too much of those two things you know, absolutely.

Speaker 2:

I like your mountain climbing analogy. I like your mountain climbing analogy. In fact I use it Myself as well, because I say many people climb the mountain, but not everybody makes it to the summit, right.

Speaker 3:

Yeah, and that's why I mean, that's why I told you, I talked to people like, why am I doing tembo? Why am I taking on postgres? There are, literally this is the super red ocean there's hundreds of competitors, all the big clouds, all have a Competitive product, you know. So I basically said this is Mount Everest, you know, to me, and I don't need to get to the top of Mount Everest, but if I do, if I do, if I, if I can build the postgres company, like holy crap, like what an accomplishment. And you know it's, it's, it's like, okay, let's just let's start climbing, see what happens. You know, am I prepared? Can I make it? Have I done enough? You know, training in life, you know, and my career, to get to the top of this thing, like we'll see. But Right, that's that's, I think, at some point.

Speaker 3:

That's why a lot of these, a lot of founders, start something, even though they don't need to, is they just want to do something even harder than they did last time. They, you can try to run up Mount Everest, like if you, let's say, you climbed it once, but now, like I have a friend, actually one of my investors, ethan from Venrock. He like runs up, runs up mountains and runs down mountains. I'm like, wow, like oh man, you know it's like we went up this path. You know, in San Francisco it was like an hour up in an hour back. He's like, oh, I usually run this. I'm like, oh my god, you know, he's like I mean, there's always a way to make it harder, you know.

Speaker 3:

Right if that became too easy for him, he could wear a backpack while running it, you know so.

Speaker 2:

Well, always push yourself hard, do hard things, and eventually you'll you'll find lightning in a bottle, right.

Speaker 3:

Yeah, yeah, I think it's good, I mean, if you can, yeah, it, like I said, it's all preparation for, for the opportunity that are presented to you and and every time you do something hard, you learn. You learn something valuable, I think, whether you win or lose. And yeah, I mean, I mean I'm still like I consume podcasts like like Very thirstily, you know, like knowledge. I'm like, oh, my god, I don't tell him, tell my new sales leader Read, listen to this podcast, take notes let's talk about, because there was like there was like 20 gems in there and it's, you know, in some cases, like I care about his learning more, more so than mine, because I, you know, I want him to do all these great things this guy's talking about. So, yeah, it's just, even if you're, you know, you kind of, are somewhat accomplished Always, if you're always learning, your help, you know, and you have people around you, they're gonna, it's gonna rub off on them.

Speaker 2:

So Absolutely, and I think we need to constantly have a hunger and thirst for learning, and I think my big takeaway on a lot of this Conversation is if you're not in the mix and understanding software and data, you're gonna get left behind. Yeah, yeah, yeah. Well, as we approach the end of our time together today, we always like to share a couple of takeaways that we can emphasize for the audience, mostly first and second time CEOs. What are the best two pieces of parting wisdom that you would share?

Speaker 3:

I would just say, like go to San Francisco, meet people, build a network there and have the rule number one. And then I would just say rule number two they say fake it till you make it. You know that confidence, you know, find yourself, figure out a way to get yourself into a confidence state of mind, or else you're, you're doomed in some ways, you know, to non-success. And then speed you know like encourage your team, encourage your Yourself to just move way faster than you think you could. I'll give you one last example. Like my dishwasher broke Broke, got an Electrician out here. He's like up, yep, it's definitely broke, it's not the electricity. And then I just went to Lowe's I bought the thing and it's coming.

Speaker 3:

You know like it's like in 15 minutes the new one was ordered. You know that that's the speed and confidence, like, is it the perfect one? Like I don't know. Like, like our dishwasher doesn't really matter too much to me and it's off my plate now, you know. So, yeah, that's the kind of stuff that you can make really. You know, non-consequential decisions very quickly, and not everybody does that. They'll, they'll, they'll. Shop too long for something like that.

Speaker 2:

So right, paralysis by analysis. Don't get stuck there, yeah. Good, Well, this has been great right.

Speaker 2:

Yep, great hanging out with you Excellent. I appreciate you making the time today and I know our audience is gonna enjoy this episode Awesome. Well, that's it for this episode of the smart money ventures podcast. Thank you for joining us. Our guest has been a Rye Walker founder and CEO of Tenbo, co-founder of astronomer and an investor at fire road ventures. Thanks for listening and we look forward to seeing you on the next episode of the smart money ventures podcast. Thanks for joining us. Right, thank you. That was great man. Thanks, yeah it's fun.

Speaker 3:

Yeah, it's awesome.