Triangle Tweener Talks

00:00:04 - Announcer
Welcome to Tweener Madness, the high stakes startup showdown where eight promising companies go head to head for a $25,000 investment prize from the Triangle Tweener Fund. But before the competition kicks off, let's meet the people making the tough calls. The judges. In this special meet the Judges episode, we're sitting down with the investors and industry leaders who will be asking the hard hitting questions, evaluating the startups and ultimately deciding who moves forward in this bracket sty competition. Each round, three judges will vote on which startups advance leading up to the finals in early April where one company will take home the top prize from the judges. You'll hear about their backgrounds, what they look for in a winning startup, and maybe even get a little inside scoop on their decision making process. So if you're a founder looking for investment, an entrepreneur curious about what investors really want, or just someone who loves a good business battle, you are in the right place. Let's meet the judges. Here's your host, Scott Wingo.

00:01:06 - Scot Wingo
Hello everybody. I am Scott Wingo, your master of ceremonies for Tweener Madness. And I am joined here by one of our elite selection committee members, Anthony Rotoli.

00:01:18 - Anthony Rotoli
Hey Scott, how are you? Thanks for having me today. Looking forward to this. This is going to be exciting. You know, obviously looking at Tweener Madness and everything else that's going on with Tweener, I'm really excited for this.

00:01:28 - Scot Wingo
Awesome. We appreciate you stepping up to be on the selection committee. You and I have known each other for feels like forever at this time. I came in place a decade, but give folks a little biography of who is this Anthony Rotoli guy.

00:01:42 - Anthony Rotoli
Yeah. So for those of you that don't know me, obviously Scott, now we go back, it's close to 25 years I think or so now. It's been a while. I've spent over 30 years in the software markets. Over the course of my career. It's hard to say that sometimes just knowing how long I've been doing this. Over the last 15 years, three time CEO, worked with many private equity companies. We can talk a little bit at that. It's just with some of the things I've seen there. But the last 25 years I've spent here in the Triangle, spent a lot of time in a galaxy far, far away with a man named Scott Wingo at ChannelAdvisor way back when. We have funny stories that we could probably talk about another time for that. But most recently I've been serving as the CEO of Ocelot, a AI student engagement platform and is Spending a lot of time now investing and looking at some other opportunities for helping, advising and mentoring. The long and the short of it, most of my career now has really been built around how do we build and scale the companies that are coming up into the entrepreneurial world and working with firms like the ones that we're going to see here and people that are trying to get off the ground is really kind of the current focus of things that I've been working on and trying to advise and be on boards and help with ventures and working with people like yourself now in different capacities across that. So, you know, super high level, but I've been doing this now for, you know, 30 years in the software world and have learned a lot along the way.

00:03:09 - Scot Wingo
Cool. Yeah. And then you've kind of made. So you were at Channel Advisor, then you went to cdw, you were in kind of like the tech space for a while and then kind of narrowed for a while.

00:03:17 - Anthony Rotoli
Yep, in the early days, you know, so I've made the rounds.

00:03:22 - Scot Wingo
Then you kind of narrowed in on ed tech and you've, you've, you've. What'd you do before Ocelot? That's another.

00:03:28 - Anthony Rotoli
Yeah, so before Ocelot, there were a couple companies before that. So I ran A, another SaaS company in the EdTech space called ESM for about eight years. I ran another one here locally called Teradata for about four years and then eventually had joined Ocelot here. All within the private equity realm. And there's a lot of things that you learn inside of that private equity world. Having left CDW and kind of went in to become the CEO roles. I will tell you, Scott, like, this is the one thing, especially when it comes to advising companies that are important to me on really building a good foundational business. Good foundational businesses usually have good foundational exits. And so, you know, those are going to be, I think, some things that are super important as a part of that. And, you know, spending, you know, a year or so now here at Ocelot in the AI Student engagement platform, which has really been an interesting, you know, change because, you know, as we all know, AI didn't exist until two years ago, even though that's not the truth. So.

00:04:27 - Scot Wingo
Yeah.

00:04:27 - Anthony Rotoli
But now everybody knows what AI is and what AI can bring. And actually having built and scaled and grown a company in that space, it's really intriguing to see what people are trying to do with those techs. But yeah, so over the last several years, I've kind of been at a few of the companies here locally, but also spent time now over the last close to 15 years in that edtech space.

00:04:48 - Scot Wingo
Yeah. And I've been, I don't know if you saw it or not, but I put out a tweener times yesterday where there's now eight transactions in the Triangle. It's most of them end up being strategic, but my understanding is a lot of them started with an inbound PE and then folks started a process and then ultimately a strategic stepped up and was able to pay more than. Than a pe.

00:05:06 - Anthony Rotoli
Yeah. And I'm not surprised by that. It's the, you know, the market's getting really active right now, you know, in a lot of things that I'm seeing, you know, not only people that are looking to sell, but, you know, the entities out there that are really trying to buy. And it's 2025 is going to be an interesting year compared to I think, what we saw last year.

00:05:22 - Scot Wingo
Yeah. In the Triangle, at least we're having a little boom lid or a wave of acquisitions, which is. I know that local investors are very happy, so I'm sure they are.

00:05:30 - Anthony Rotoli
You know, I've seen some of those transactions and there's been some pretty good ones. And you know, knowing a bunch of the companies and knowing, you know, being part of the network here for as long as you and I, you know, have been, it's really cool to kind of see these exits starting to come to fruition. For a lot of people. It takes, and this is, you know, one of the things for the people that are listening today too, it's you takes a lot of work to get things to these places and it's not an overnight success, you know, kind of things as we all wish they would be. But it's really cool now that, you know, to your comment, like the, you know, I did see the article, the fact that we've had eight so far this year and it's mid February.

00:06:04 - Scot Wingo
Yeah, it's pretty crazy.

00:06:05 - Anthony Rotoli
It's really crazy what the year is going to, you know, kind of shake out to be.

00:06:08 - Scot Wingo
Yeah, we can't, we'll run out of companies if we keep this pace up. So I don't think it's going to stay the same, good or bad. The. Okay, so you, you know, so you've got deep operational experience and you're starting to do more helping companies. You're doing some board work. You're. You're an LP in the tweener fund, which we appreciate. Anything else? Are you writing individual checks or do you put. You try to do it more through, through the fund or what you're doing.

00:06:35 - Anthony Rotoli
Mostly through kind of like the, like the tweener fund and things like that. But I am starting to explore some of the individual, you know, check routes. I'll tell you just from an investment background, you know, in particular with myself, I also like, I'm very hands on and want to be able to roll up my sleeves. And this is where some of the board work that I've been doing is really paying off because I can add a lot of strategic value in that operational sense. Then it's just they, here's some money, good luck, we're all counting on you. And especially when you've kind of gone through the organizations that I've gone through with these private equity kind of backed funds, I know what they're looking for at the end of the day, which is also what strategics are looking for when they're trying to buy. And we all don't want to sell low, right? We want to sell it high. And so for me it's more than just the capital, it's also about like putting in the board process, the governance, the operational excellence that needs to happen to become an attractive, you know, organization. So yeah, so I've been dabbling in a little bit of both, but definitely spending a little bit more time on kind of working towards the hands on approach where I can because I think, you know, look, I've been mentored just like the rest of us have said and I've seen a bunch of the other, you know, trainer talks, things you've been doing. We've all had a mentor at some point and just like me, I've been mentored. I've had, you know, people in, you know, back in the day like you and others. It's important to be able to give back in the other ways too because I do believe in the pay it forward and you know, I've had that opportunity so why not, you know, be able to do it in some of those ways as well.

00:08:06 - Scot Wingo
That's awesome. I have a lot of first time founders that kind of say well you know, why should I have a board? And you know, that's an easy answer. And but then they're kind of like what kind of things can the board help me with? So as when you're wearing your board hat and you're in one of these things like what are some of the tactical things you're helping the founder think through?

00:08:24 - Anthony Rotoli
Yeah, well that's really, it's a little bit all over the place depending on the organization that we're working with, but one in particular that I'm working with right now. And those who look me up can see that one where I'm the board chair. It's a lot of mentorship at the CEO level. A lot of CEOs. It's a very lonely place. And they don't really understand what it actually takes from an operationalizing of an organization. Whether you're an individual founder or you have multiple people in the organization, look, five or six people, you're real at that point if you're working with. And a lot of people have not come up through those ranks, don't understand where the mentorship before that actually happens in order to build, scale and grow and even get into a point of raising funds. So I'm spending a lot of time with helping them kind of operationalize what is revenue, you know, need to look like, what types of things, not just what your governance rules need to be or bylaws and that kind of stuff, but also looking at like, structurally, what processes and standard operating procedures you should start thinking about when you're sub $1 million, you know, 250, whatever, versus what happens when you hit the million and you get to five. And having lived through all that, it's really important from a board perspective to kind of help the staging of where that goes. And it's really, it's fun because I enjoy working with these founders who have a great understanding of the space that they're in, but then don't necessarily understand what happens post. And there's a lot of loss, like in conversation and translation that happens there. And in today's world, it's like, if you can lean on, okay, great, you're an expert in whatever B2B SaaS solution you're building. That's awesome. But let me help you about how do you actually operationalize that? Because through my career I've bounced through different industries, so it's not that I just knew one. It was really about how you operationalize the business. So that's really, you know, on the board side, it kind of leans depending on what the needs are. And there are some startups that don't even know how to go develop, you know, the product. And I've got teams that I've worked with, you know, for years offshore that it's like, let me make an introduction for you and like, help you with how do you build this thing?

00:10:31 - Scot Wingo
Yeah, cool. So you can kind of go from zero to exit, basically.

00:10:35 - Anthony Rotoli
Zero to exit.

00:10:36 - Scot Wingo
And having done it through the skills There.

00:10:38 - Anthony Rotoli
Yeah, yeah.

00:10:40 - Scot Wingo
I was going to ask what category you're most interested in, but I think you just kind of answered that. It seems to be like B2B SaaS. Obviously, ed tech is where you've got probably the most experience in the last 10 years. So I guess you would probably avoid anything that's like you wouldn't do consumer or anything like that.

00:10:58 - Anthony Rotoli
Not necessarily. I've lived in those worlds, obviously been in, you know, Channel Advisor with you back in the day and you know, even when I was at cdw, you know, we were in the retail hardware, you know, space. So I've got a good understanding of supply chain as well. One of the ones that I'm on the board now is actually a hardware software play in the manufacturing space and it's a fit for me just purely. Yes, it's a B2B software play, but it's also in the supply chain space. Right. And having spent a lot of time there and understanding what actually happens when you have to move things through the supply chain. Yes, B2B is typically where I've leaned most of my career on the SaaS side. But I will also say what's really interesting to me now is just how people are leveraging AI and having now just spent the last year plus building onto a AI company and really taking that to high scalability. It's really exciting to kind of look at those types of companies to see how they're leveraging the technology as opposed to just being another GPT. That to me is not exciting. And I will tell everybody who's listening right now, people aren't getting excited by that out in the investor world either.

00:12:10 - Scot Wingo
Yeah, they call them wrappers. Just like a very thin layer between just a chat bot on top of the.

00:12:15 - Anthony Rotoli
Yeah, correct. Like if you're building an agent, that's not exciting anymore because it's really. Yes, it was maybe two years ago when this first came out, but now it's like truly, how do you build the RE ranking models? How do you build everything that sits in between? And having these rag architectures for the geek that are out there that want to understand, like I just spent, you know, a year plus, you know, working around these environments. It's really super cool when you know how to throw your data warehouse under these things and watch it process that data and how fast it works. That's getting exciting to me. And especially what we're starting to see in that space as you know, Scott, like in talking to a lot of these companies six months ago, a lot of These things didn't even exist. I know it's going to be really exciting to kind of see what the next year has and how they're leveraging tech that didn't exist six months ago. So that, that's actually getting me a little bit more excited in some of the companies that I've been exploring. Working with is really around how are you leveraging AI as opposed to, hey, we're just another AI company.

00:13:18 - Scot Wingo
Yeah, we're seeing. And I'm in that same tweener times I mentioned Keebler Health where they, you know, these, these two guys or three, three founders had an idea and within 18 months they've just like off to the races. Usually is a founder that has a deep subject matter expert, some kind of data that they can. It's like either exclusive or they know where to find this data. And if you train on that data, it gives you a bit of a network effect because your solution learns faster than everyone else's. And then just like a mindset to go fast and kind of and then also to be wildly efficient. So it's really interesting. You and I probably raised, I don't know how much between us, but a lot, a lot of money. And it gets, gets kind of. You end up spending all your time at, you know, once you get to like 5 million in revenue and now.

00:14:05 - Anthony Rotoli
Like the time like it's just changed on how fast you can do this and how inexpensively you can do this, you know, because in. I've heard you talk about it, I've talked about it too, with just some of the businesses I've been a part of where it used to take millions and millions and millions of dollars to do these things. You're doing at a fraction of the cost now because you've got all of these other platform tools that you could just layer on that, you know, we didn't see six months ago, a year ago. And most of a lot of them are open source. And that's the one thing to those that are listening that are trying to build their companies right. Like you can look at tools now that are open source that will cost you little to nothing to build on top of your data warehouses and your knowledge bases. Like you've seen, you know, some of these others and you know, taking advantage of that is huge in today's environment. And now that is one of the things that I'm watching as I'm looking at some of these companies. Like, how are you really architecting? And are you architecting in a way that's going to be efficient and scalable and that it's not going to cost a ton of money later just because your prototypes are like all pie in the sky. And now, you know, that's one of the things that I'm looking for because clarity in that is going to be king cool.

00:15:16 - Scot Wingo
All right, so you're going to be on our selection committee. What's your advice to some of these? And these are all pretty early stage and I think everyone's a first time entrepreneur. I actually didn't look at it from that angle. But anyway, what's your recommendation? So they're going to be there, we're going to be in studio and they're going to be up against another company and you're going to be one of the selection committee members. What, what's your advice to these entrepreneurs.

00:15:41 - Anthony Rotoli
For how to, how to win us over to try to try to get to the. There's a few, you know, points that I'll make and I'll try not to make this, you know, too long, but I'll make it, you know, kind of summarize it a little bit. You know, there are a lot of great ideas out there and one of the biggest things I've seen with a lot of entrepreneurs is just making it too complex for everybody to understand what that idea is. So the more you can make that value prop simple and really understanding what it is and the problem that you're trying to solve is going to be critically important and not just trying to reinvent the wheel. To reinvent the wheel. And so, you know, when I've seen that is like really kind of how you focus on the business and not just what the product is and the solution you're probably, you know, probably trying to solve is critically important in just a lot of the things that I look at because, you know, we all like cool tech, we're all in the tech space, but investors and people that are looking to participate in rounds and things like that are really truly looking about the market and how you're trying to solve that problem. And that's one of the things, you know, that I look for from an advice perspective is just like, do you have the right signals, right, to show that there's a market there and it's not just about one of the other pieces of advice. It's not just about your tam Sam. It's like, do you have a wedge? Do you have something that makes you so different that it's not just about that cool. I've got this billion dollar market that I'M going after. And I think, Scott, we've seen a lot of those, you know, types of organizations and if you can really drive a wedge into where you're working and you have and understand your ideal customer profile, a lot of times, you know, I've said to a lot of entrepreneurs and early stage startups is like, hey, look, if you know who that ICP is, then start talking to them. So I want to see. Also advice is that you have been talking to your customers. And I always say this feedback is a gift. You may not like it, but for, you know, early advice for people is you can't talk to enough customers early enough. And even as you get later stage, this is advice for everybody too. You should still be talking to your customers. And I think a lot of people forget, like, we have a market, we've got sales, we don't need to talk to them anymore. Well, in actuality, you need to.

00:17:50 - Scot Wingo
It's funny you say that. I was mentoring this guy in Europe and he's got like a $10 million e commerce kind of solution company and he's like, growth is slow and I don't know why. And it's like, well, when's the last time you talked to 10 customers? And he like literally blushed and he's like, two years. Exactly. I was like, you know what I'm gonna say? Put his head down. And shame's like, even having a new.

00:18:09 - Anthony Rotoli
Product within a core set of products that you have, you still need to get that feedback because you don't want to invest all of this money in building something that is just going to fall flat. Right? So advice to entrepreneurs, it's the same thing when you're building your first product and you're trying to launch. So if you can build that wedge and you know who it is, you know, talk to them. Because I want to see what the initial addressable market is. And this is probably a term that a lot of people haven't heard before, but it's like, I know that I can address a certain sub segment of a client. That to me is one of the things that's important and I've learned through the PE kind of world is really knowing that you can get to that customer profile in an initial market if you're about to go expand. And so it's the same thing that happens when you're an early stage. So the advice is like, just don't talk about Tammy. Like really think about it down into the layers of how do you get that market share and that you're thinking about how do you scale the business as opposed to, hey, we have this cool little niche. And to your point, you know, Scott, like, hey, I haven't talked to them in two years. Well, if you should be going every day talking to your customers and then, you know, one of the last things I'll say just from a piece of advice is as you build team is important and you can't do everything alone. And even at scale, as a three time CEO, I've learned that there's no way I could do it alone. So as things evolve and market shift, you have to lean on people. And so even as a solo founder, you can actually reach out to other people and surround them, which is your boards, your advisors, your mentors. And I think a lot of people forget about that too, about how they can lean on resources in the community, yourself, myself, others who have been there, kind of done it. And advice is don't be afraid to ask. And I think a lot of people are afraid because they don't want to be told no. And we've all been told no a gazillion times. And so lastly, just don't be afraid to ask because it shouldn't be a lonely place, but we sometimes make it a lonely place.

00:20:11 - Scot Wingo
Awesome. That's some great advice. It's going to be fun seeing you in the studio. Any last thoughts for folks? I think the audience for this is largely going to be some of our contestants and other founders out there. Any, any last advice?

00:20:24 - Anthony Rotoli
Yeah, last advice is first off, this is an awesome opportunity for everybody that's listening, you know, out there and that's participating in this. Nothing's been really done like this before. So I give you and Robbie a lot of props, you know, for what you guys have been doing, not only with just the Tweener fund and everything else, but this is a really cool, fun, you know, idea, you know, for it.

00:20:44 - Scot Wingo
But it'll either be great or terrible. It'll have a binary outcome.

00:20:48 - Anthony Rotoli
Yeah, this is one way or the other I lean towards. Great.

00:20:52 - Scot Wingo
Well, we'll see.

00:20:52 - Anthony Rotoli
Yeah, if you're pitching, this is my last. The thing I'll close with. If you're pitching, take all of the feedback seriously because even though the investors may pass and you know, Tweener may pass on this opportunity, it's still probably going to open doors for you later. And because you're going to have a level of exposure and building some relationships that you didn't have the day before and then taking full advantage of that opportunity, you know, is going to be in your best interest at that point. So I'm excited to see kind of what happens here and you know how it all works. Awesome.

00:21:25 - Scot Wingo
Well, thanks for volunteering to do this, Anthony. We appreciate it and we will see you live in the studio. It's going to be a lot of fun.

00:21:31 - Anthony Rotoli
All right, good luck, everybody.

00:21:37 - Announcer
That's a wrap on this Meet the Judges episode. Now you know the minds behind the decisions, the investors and industry leaders who will be putting these startups to the test as Tweener Madness kicks off. They'll be asking the tough questions, making the tough calls, and deciding who advances in the bracket, all leading up to the finals in early April. Make sure you're subscribed so you don't miss a single matchup. And if you want to follow along with all things Tweener Madness and the triangle startup scene, head on over to tweenertimes.com also, if you're thinking about launching your own podcast or want to bring professional production to your brand, check out earfluence.com the competition is about to begin and we'll see you soon in the next episode.