Alan's Thinking Cap | Q3 2024 Capital Markets Update

Alan Wink:Thanks. Scot, you've had an incredibly successful career as a serial entrepreneur. You've started four companies and successfully exiting from three of them, and I'm pretty sure that your fourth company, Spiffy, will also yield a nice exit. Can you give us a little bit of a perspective or elevator pitch on the companies you started and what the exits were like?

Scot Wingo:Yeah. So first of all, I'm from South Carolina. I went to University of South Carolina for an engineering degree, computer engineering, and then came up to this area in the Raleigh, North Carolina area for North Carolina State University, go Wolfpack, and got my master's. And then I went and got a job at a startup out of school up in your area, in the New York area, it was in Connecticut, and realized I love startups, but I'm not built for cold weather, so moved back here to the Triangle in 1995 and started my first business. That was called Stingray Software, and it was bootstrapped, and we developed ...

It's what today we'd call dev tech. That term didn't exist back then, but it was developer tools for Visual C++, developers within the Microsoft kind of family of products. Started that in '95, and then sold it in '98 to a public company, and that was an exit that was kind of north around a $20 million exit, so that was good, especially when you bootstrap. You can have some singles and still have a pretty good outcome. And then at that time, you can't tell, but I'm a big Star Wars fan, so I had some liquidity.

The Phantom Menace, which is episode one, came out, and the internet e-commerce was in its very early days. And in those days, you actually bought more things through an auction kind of a format than fixed price. So started a company in that world called AuctionRover, and the idea was we would search a couple hundred auction sites, and then we had a buying agent and a selling agent. That was the internet bubble, so we started that. Raised $3 million from Draper Fisher Jurvetson affiliate, and then were acquired very quickly by the folks that invented paid search that were called GoTo.com, and then they changed their name subsequently to Overture, and then they were subsequently acquired by Yahoo.

And then, what happened is as they started to compete more with Google, they decided to shut our group down, and in the post dot-com bubble explosion, the only site that was left was eBay in the auction world. And if you only have one site, you don't need Search or Bid Agent, but our selling product became very popular to the point where large businesses were using it like IBM and Motorola, so they were going to shut us down, and we said, "Well, this idea of helping big companies saw online is interesting to us. Can we basically spend that out?" So we spun that out in 2001 as a company called ChannelAdvisor, and division was, number one, we felt like e-commerce, which was still nascent, would be a pretty big thing. Turns out we were pretty good on that one, and number two, we liked this idea of auction sites kind of became marketplaces, which is kind of a modern take on malls in an e-commerce venue.

You may not realize it, but over 60% of the items sold on Amazon are actually third-party items as part of their marketplace concept versus Amazon proper. So started ChannelAdvisor in 2001, and this one's a longer story, but to keep it short, we raised 90 million venture capital, so I've gotten relatively good at raising VC, and went public in 2013. That was always kind of one of my goals, even as I had odd goals as a teenager. I wanted to own a Lamborghini and I wanted to take a company public, so I got to check one of those off my wish list. And then, one of the things thematically I like as an entrepreneur is this idea of Marc Andreessen calls it software eating the world, or these really analog businesses going digital very quickly.

You guys see it in your business all the time, right? And that's kind of what e-commerce was, the traditional retail brick-and-mortar world, going digital in the form of e-commerce. I had my first Uber experience right around the time of the ChannelAdvisor IPO roadshow, and I couldn't shake this idea that services were going to go digital, and what would that mean? It would mean we'd want them to be accessible from our phones, and they would have that Uber style kind of an interface. So started a company in 2014 called Spiffy, which is on-demand car care, which basically gives you an app, and you can say, "Hey, I'm Alan. I'm busy."

"I'm doing all these famous webinars. I want my car taken care of. I would like you to come to me at my home or place of work and do wash, oil change, tires, brakes, all that kind of stuff." We also do it for businesses as well. That actually is the lion's share is B2B fleets.

So that business now, we've raised $90 million, and that business is about a 60 to 70 million run rate. Yeah, so that's been my entrepreneurial journey so far.

Alan Wink:What a great roadmap. I have to ask you, did you get the Lamborghini?

Scot Wingo:I did not. At the time of the ... So I sold my first company, and I had two little kids, so I got a minivan, and then I did treat myself to a pretty earl Tesla Model S in 2000 after the ChannelAdvisor IPO.

Alan Wink:So you're presently the general partner at Triangle Tweener Fund. Can you give us a little idea of what the investment focus of the Tweener Fund is, and also any lessons that you learned as an entrepreneur that you're applying in that fund?

Scot Wingo:Well, as an entrepreneur, I've probably gone to ... I've lost track. I've probably done 400 pitches, I think, and gotten maybe 15 yeses. So that's kind of the batting average that you have as an entrepreneur. You're kind of happy if you can get highest single digits.

And I've had some really bad pitches, so I'm always cognizant of that. I've had a lot of ... I've flown places and people no-showed me. I've had every bad experience you can kind of imagine. So I always have that in the back of my mind, and I kind of accidentally stumbled into this, if you will.

And the short version of the story is I've always been very thankful for mentors that I've had. I had a very early one in that first business, Stingray Software. I was an engineering person, and I'd never taken a business class, started a business. My co-founders were also engineers, and we got that thing up to $5 million, and the wheels were coming off the bus. We didn't really know what we were doing, and hiring salespeople and didn't know how to compensate them and do the basic accounting, any of that stuff.

All that stuff was broken, but we had a good product. So I had this mentor, his name was Richard Holcomb, that was 10 years older than me, and he was in our local area, and he helped me out immensely for basically two years. And I used a lot of his time, and I basically said, "I wish ... Can I pay you for this? I feel bad, I'm using a lot of your time."

He said, "No. We're really trying to get this to be a top-tier entrepreneurial center. You just pay it forward in 10 years. You help ..." I was 28 at the time. "When you're 38, you help a 28-year-old."

And I said, "Well, I can get behind that. I like that, pay it forward kind of thing." So I've been doing that for 30 years. The first 15 or so was really just mentoring. And then, between ChannelAdvisor and Spiffy, I looked around our entrepreneurial ecosystem here, and it exploded. We had just thousands of startups.

And the challenge was we knew there was a lot of startups. There's like a thousand, and we knew there was six or seven that were kind of on their way to really being big. We have one here, Pendo, that's kind a unicorn now, but we didn't know what was in the middle. We needed a definition. It's a simple thing, but no one knew like, "Who are those up-and-coming companies?"

So I started this list of up-and-coming companies called the Triangle Tweener List. You can just go to Tweenerlist.com. It still exists today. I started it in 2015. So that list became very popular, and to the point where I started ...

And I defined these Tweeners as a million ARR on the low side up to 80 million ARR. And the way I figured that out is their headcount on LinkedIn. So I don't ask the companies, I look at LinkedIn. Every company has a page, and if they're north of 10 people, they're usually past a million ARR for kind of technology companies. We don't do life science companies at all because that's a whole different beast.

These are all technology companies minus life science, and then we go all the way up to 80 million. So when I first started this list, there's 50 companies, and now there's 300, to give you an idea for how our region has grown. So that's six decks in nine years, which is amazing. So I started keeping more data on these Tweeners, and what started to be kind of interesting was this is an algorithm that never misses a winner. So every company that's ever sold in the Triangle, I already had on the list because they all pass through a million.

It's a really good kind of trap, if you will, to catch any up-and-coming company, and the failure rate is very low. So traditional VCs would tell you, "Well, we're going to go invest in 15 companies. A third are going to be zeros. They're going to fail. A third are going to return what we put in, and a third will be heroes, and maybe one or two will be power law companies."

So I thought, "Well, this is an interesting thing I've stumbled on. It's got a lower failure rate." And I catch 100% of the winners, and if you think about power law distribution, that's what's important. If you do the math, it's important not to miss a power law company, which is a company that returns north of the 10X. So I thought, "Well ..."

And then, another thing is when I invest in the public stock market, I like a hybrid structure of invest in some stocks I like and understand, so kind of a stock-picking side, and then on the other side, I like to put some money in an S&P 500, like a Vanguard index fund, and I thought, "Well, traditional VCs are kind of like picking winners," just like Fidelity or something in the public market, "And is there an index strategy maybe that would be an interesting approach?" So started the Tweener Fund. It's Triangle Tweener Fund. I abbreviate it to Tweener Fund, with this idea of, "What if we invested in lots of companies when they're in this target zone?," that is inspired by this algorithm I call the Tweener List, which is the equivalent of the S&P 500, if you're following my analogy there. "And what would that look like?"

"Would investors be interested in this? Could we really put a bright spotlight on this area and help these companies scale to that next level?," and so forth. So that's kind of a long answer to the origin of the Tweener Fund.

Alan Wink:So, Scot, assume when you were building the Tweener List, you must've had a lot of earlier stage companies approaching you, wanting to be on that list, I assume.

Scot Wingo:Yeah, and I hate being the Simon Cowell. I am not a good judge of other people's ideas. I don't want to be in that business, which is part of what I like about this versus traditional VC. And maybe it's all the nos I've received over the years, and then gone on to prove them wrong, which is always fun, so I didn't want to have to do that. So what's nice is the list is, it's very open, so it's super transparent.

VCs tend to be, but then sometimes you never really know why you got a no. So this one's like, "If you fit in this criteria, we want to write you a check," and the criteria is very simple. "Are you a tech company? Are you in the Triangle?" So we have a very clear definition of that, and, "Are you over a million dollars annually?," and that's it.

Now, we don't just automatically write a check. We do very light due diligence. This sometimes makes other people in venture a little freaked out. We do super light due diligence, and usually it's meeting the founder, seeing a demo, and looking through some materials, and that's about it. We don't do a forensic.

We're not looking at their code, or verifying invoices, or looking in their bank accounts, or anything that forensically. So the idea is if you can get a set of customers to pay you a million dollars, that's better due diligence than we could ever do.

Alan Wink:Very interesting. So let's switch gears a little bit and talk about the present state of the VC market, both nationally, and even what's going on in the Triangle. I think that the present state of VC could be described as sluggish at best. The return on venture investments in the form of IPOs or sales of startups has been extremely light. GPs are having a very difficult time returning capital to LPs.

What do you think's going on in this space today? Has venture capital lost a little bit of its luster? Give me your thought.

Scot Wingo:Yeah, there's definitely ... Everything's kind of seized up, and the points you raise, there's lots of really good content out there on that, but there's two others that you didn't mention. Number one is the election. So a lot of people feel like the government has stopped almost any acquisition, so that is really bad for our ecosystem. The big one that got all the headlines was Adobe, Figma.

That was like ... I forget what it was, four or six billion. If that had happened, money would've rained through the system and the gears would've kind of like been lubricated and kept going. We need those as an ecosystem, but we have a government kind of philosophy that they don't want to do. That's a big one.

They're actually blocking a lot of small ones. This doesn't get a lot of press, so this is a problem. At the same time, the IPO market is basically closed. I met some bankers just yesterday, and every time I talk to them, the what you have to be to go public goes up. In January, they were saying 200 million.

This would be for traditional SaaS business, a software business. They were like, "Well, you kind of need ... When we went public at ChannelAdvisor, you had to be 80 to 100." 80 at line of sight to 100, and that was 2013. Early 2024, it was 200 to 250.

And I just met with these folks, and they're like, "Well, we now think it's going to be 300 to 350 going into next year." And so that's very hard to get to. It will take a business 15 years, unless you're kind of like OpenAI, and you're just growing vertically. Any traditional software business is going to take 15 to 20 years, and the venture model's not built for them. So there's a lot of people that feel like ...

And it's kind of pretty evenly split. They kind of think whoever ... There's red and blue people that think their candidate's going to unlock that. We'll see. I don't know. And so that's one.

And then, another one that is kind of like the whisper thing that I haven't seen printed a lot, you hear inklings of it, is this whole AI thing is really freaking people out. So an example is there's this company called Klarna, and the first thing they did is they reduced their headcount from 5,000 to 2,000 people by replacing customer service agents with AI agents, and then, now they're starting to chew away into the software developers, and then they announced they're going to rip out Salesforce and Workday, and they're basically going to build their own versions of it for a 10th of the price that they're paying. I feel this in my heart because at ChannelAdvisor, we were stroking Salesforce a one and a quarter million dollar check every year, and I did the math on it, and at that point, we weren't efficient enough and we didn't have enough engineers to kind of replace it. In today's world, supplemented by AI, we could probably rebuild that for like 500K or something, so it would be like a no-brainer to rip that out. So everyone hears these stories, and now, all this rolls downhill, right?

So then you start to say, "Well, if Salesforce could be replaced by these kinds of people, augmented by AI, engineers rebuilt with that. What about if you're a SaaS startup? What's your competitive moat now?" So there's a lot of people kind of waiting to see how AI is going to impact all these things, and so I think there's a lot of VCs that kind of do that calculus, and they're like, "Well, my LPs don't want me to invest right now. I need to keep my dry powder."

"There's a lot of risk in the market kind of from all these things. I kind of like really want to be very, very, very cautious right now."

Alan Wink:But, Scot, I read a statistic recently that there's about $2.5 trillion that's in venture-backed unicorns, that's got to find an exit at some point. Don't you think the market's ready to explode? Everyone I talk to thinks that 2025 is going to be a banner year. Do you agree?

Scot Wingo:I want that to be true. I'm not a good ... I'm not a procrastinator. I don't kind of predict those things. I do think we're very spring-loaded, and if certain things ...

So another one is interest rates. A lot of these private equity models don't work at the current interest rates we're at, and if they can come down, then private equity will get going, and that could be part of it. I'm not sure. I've heard all these interviews from the Stripes and Databricks people. They're perfect.

They're happy as clams staying private and doing what they're doing. And I think we also need, we need some kind of review and rethinking of the public market itself. When we were public at ChannelAdvisor, you hear all these horror stories about these short traders doing all these nasty things. I was like, "We're going to be a microcap. We're going to have a market cap under a billion," which in their world's microcap. We're not going to be impacted by these.

But sure enough, for every one of these kind of activists, kind of crazy folks that are way up here, going after to the big guys, they actually got to the small guys too. So we'd spend all this time dealing with stuff that was not productive of them. So there's parts of being public that are just kind of ... I love the transparency part of it, but at the same time you have this lack of transparency that makes it very hard to run a public company, and it's usually in the world of hedge funds, and shorts, and naked shorts and all that kind of stuff. It's really nefarious kind of what it does to the companies that are out there. So we need some reform there, I think, as part of this unlock all this value.

Alan Wink:So let's put your founder's hat on for a second. Many people describe the present VC market as challenging for founders who are out there, trying to raise capital. You've successfully raised capital for a bunch of companies. In your opinion, is this a challenging market compared to the times that you raised money in?

Scot Wingo:It really is. It could be ... So I've been through several of these big dislocations, so 9/11, the great financial crisis, and then COVID. Those periods of time were incredibly hard to raise capital, but they ended, and then it kind of came back. This one's really weird, and there was an external event that you kind of knew that was causing it.

This one is harder to read, and it used to be that we saw it here in the Triangle and in some of the data. It was definitely kind of at the late stage first, so it kind of has worked its way down the cap stack. So it was definitely in the D, E, then it was in C and B rounds, and now we're seeing it in A, and then even C. So we have some companies that we invested pre-seed, that they're doing 500K to a million, million and a half a year, really great companies that are growing like crazy, and they'll get six people that want to invest, but no one wants to lead. So everyone's really worried about leading right now because they don't want to kind of get stuck carrying the water, as VCs would say.

They don't want to be the one that's kind of signing up implicitly to figure out what happens next. So there's a lack of risk-taking, so it's very risk-off right now, but it is interesting because you'll find it's very frustrating for the founder because ... I've actually had four conversations in the last two weeks. I've got all this money that will come in, but I'm waiting, no one will lead. Like, "How do I get someone to lead, and how do I get them over that hump?"

I don't have a silver bullet for that, but there's some strategies to kind of get there, but what a lot of companies are doing is they're just saying, "Well, I'll just put a ..." They're basically kind saying, "I'll tap into my existing investors, I'll grow a little bit slower, and I'll do like a convertible note or a save, and get another six months and kind of kick the can down the road." But a lot of A, B, C, D companies have kicked the can three times, and they're kind of like ... The can is getting shorter and shorter away, and it's kind of like, "You can only kick that can so far." So, yeah, if something doesn't give, the failure rate is going to go way up, especially some of the later stage stuff, and then they'll kind of ripple down.

Alan Wink:Well, I think something has to give because of all the pent-up value in these companies, something has to give because VCs are sitting on an awful lot of dry powder that's got to find the home at some point in time. To add insult to injury that does 2.5 trillion of pent-up value in these unicorn companies, 40% of that's been sitting on. Those companies have been involved with their VC funds for nine plus years. They have to find exits pretty soon.

Scot Wingo:Yeah, I'm an LP in some funds, and two of them have already asked for two-year extensions past the tenure.

Alan Wink:Oh, really? Yeah.

Scot Wingo:So we're starting to see it, and that's early stage, so we're seeing that everywhere. Another thing that is happening, and I don't actively participate in this, but I get pitched in a lot, is the secondary market is kind of ... Maybe one of the release files is something we haven't thought of, and it's the secondary market, so there's a very active secondary market. There's some names that are quite popular, the SpaceX's Groq. Not G-R-O-K, G-R-O-Q, which is an AI company, OpenAI shares.

There's some hot ones that they're trading, but you're starting to see ... Even, I've been offered here in town some secondary from Pendo, and then we have an AI startup called Pryon. So there is this secondary market, but it's kind of like, it's not ... I prefer the openness of the public market, where you can kind of see what's going on and there's a price. And so a lot of it is kind of like, it's like, "Hey, I've got ..."

It's almost like back alley, like, "Hey, I've got some shares of SpaceX. You want to buy?" You dig into them, there's always a little bit of hair on there like, it's this SPV that's held by another SPV that's held by another SPV, and they've got nested two and 20's and all this ... You start modeling that out, you're like, "I don't know how this is going to ever result in an ROI." So I do worry that there's like ...

Because of this, there's these shady parts of the market that are kind of developing. Certainly, there's some secondary markets that are very transparent, but a lot of it is kind of like behind the scenes people calling you, and I'm not really sure. I'm sophisticated enough not to participate in that because it always seems a little weird, but I do worry that by this all being jammed up, it's creating this kind of dark corners where things are happening that may not be good for people.

Alan Wink:You briefly touched before on the concept of AI, and every VC is looking at AI opportunities today. From your experience, Scot, where do you think the real opportunities in artificial intelligence are, and what can we expect over the next three to five years?

Scot Wingo:Yeah. So you have your platform companies, and we'll see. There's a valid argument on either side that they're going to be huge or race to zero. We kind of have to see. Here in the Triangle, what we're seeing that's really interesting is you now have this kind of set of Lego blocks that use AI inside of them, and we're seeing founders that have very specific subject matter expertise applying those Lego blocks in interesting ways.

One here that's doing a good job raising, they're in the health tech space, and whenever you go to the hospital or something, there's all these codes of what procedure. Let's say you had your appendix out, and your insurance company rejects that. Well, at the end of the day, inside of all these health entities is someone that knows how to code that the right way to get the insurance company to pay for it. So what they're doing is they're taking that and training a model on that, what these humans are doing, and now the model is better than the humans at it, and you can scale it up infinitely because it's a model. So then, they license that out to the people that need help because they're woefully behind because the number of humans that can do this is low and they're not getting bigger, and no one really wants that as a career, so it's like this problem that the industry has.

So that seems like it has much more of a competitive moat to me because you've got this access to proprietary data. It gets better the more data it has, so it has a network effect. So we're seeing a lot of companies in the health tech category, manufacturing, supply chain, compliance, and in your world of accounting, there's a lot of people that are ... I saw one the other day that helps private equity firms do due diligence. So it looks at the data room, and it just kind of surfaces things immediately and says, "Mm, this contract looks like it has an intellectual property problem."

"You should look ... This one wasn't signed. This one has unlimited liability." So it's really interesting. There's law tech, finance. There's a variety of these AIs that are being used in these things that I'm kind of intrigued by.

The other thing that's interesting, and this ties into VC, when I talk to these founders, they're getting so much amplification from using dog-fooding AI themselves and all the tools for developers and business now. They basically have a model that shows them raising five million, and they're done. So we call that seed-strapping. So they want to do a pre-seed and a seed, and then maybe a little bit more, and then they don't think they're going to need to raise money anymore, because they're going to get there on five people. They're going to get to four or five million, maybe 10 people. They see a day where they're not going to need any more venture capital.

Alan Wink:So that's a really-

Scot Wingo:That's interesting if you're a VC. If you're a series C VC, I don't know what that means for you. I don't know if it's going to work or not, but if it does, it's going to be really interesting.

Alan Wink:So that's a great segue into my next question. Founders always struggle with the concept of, "How much money should I raise, and how should that capital be deployed?" What's the advice you give to pre-seed and seed stage companies in terms of the level of capital they need to raise, and how that money should be effectively deployed?

Scot Wingo:Yeah, first I kind of ask them, and this is where you kind of get on the founder couch, if you will, and a lot of it is like, "What do you want to build and how fast?" And so take externalities out the equation for a minute, and first of all, they need to decide what they want to build and how fast. So that's part of it. The answer is it's fine to build a business that's a lifestyle business, what VCs would call a lifestyle, that doesn't take VC. One of the things I would say that's really interesting about the Triangle.

Of the 300 companies on the Tweener list, about 100 are bootstrapped. And they usually consult for a while, and then they'll find something, and they'll build a product, and they use consulting as a seed, pre-seed round basically, and then they roll that into a product. So we've got many companies here. Famously, we had one called Prometheus that got to be unicorn, just bootstrapping. So because it's relatively inexpensive here, that's before AI.

So I think AI is going to just make this even bigger. So that's the first question. And then the other one is, "Okay. Now, you have to layer in externalities because we don't live in that world where there aren't externalities." So if you're building a software as a service business and you get to five million, you will have 10 competitors and they'll raise capital.

So a lot of times it's not a, if you want to stay competitive, because once you build a software as a service business and get it to five million, it becomes a sales and marketing game, like pouring the gas on sales and marketing, both sales reps and marketing dollars. So in many categories, that's not an option. At Spiffy, we had to raise capital because we're relatively capital efficient, but we have vans and technicians and stuff that required it. Yeah, so that's really the factors, but if you're building a ... There's many, many businesses here.

There are certain categories of SaaS, where you're narrow enough, that no one is really going to bother you. Then, maybe you go kind of bootstrap until you get a competitor, and then you can kind of reevaluate.

Alan Wink:So I've been given the two-minute warning about two minutes ago, so we are putting up against the end of our time, but I always have a question I love to ask successful entrepreneurs. You've been at this quite a long time, and you've had a great deal of success. What's the one deal that got away from you that you wish you had back?

Scot Wingo:Yeah. So I'm actively involved here at NC State, and this professor came to me and he said, "I've got this idea." And it was an hour-long pitch, and the first 45 minutes, he talked about how he had studied ants. And I was like, "Okay. Are we doing ant farms here?"

And then, finally, in the last 15 minutes, and he's like, "And based on that, I'm going to build an algorithm for robots to run warehouses." I was like, "Wait a minute. I've been listening to ant behavior for like the 45 minutes," and I couldn't wrap my head around it. This is like this 2007, let's say, and I just like, "This is the craziest thing I've ever heard." Well, then, he went to start this company called Kiva, K-I-V-A, and sure enough, they had these orange robots that could move shelves around like ants. They used an ant algorithm to do it, and Amazon bought them for $400 million.

Alan Wink:That is ... And you could have been an early investor.

Scot Wingo:Mm-hmm, but it seemed too crazy to me to be like a thing. So that's why I know I'm not good at judging other people's ideas. Now, if someone starts with ant algorithms or bees, I'm like, "Let me write you a check."

Alan Wink:That's why when you present to a VC, you got to get your point across in the first slide, why this is important.

Scot Wingo:Yeah. Yeah.

Alan Wink:Scot, I just want to say thank you for a really engaging conversation. I really enjoyed it, and I'm sure most of our listeners did also. So at this time, I just want to pass it back to Bella.

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