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
Hey, everybody, it is Scott Wingo from Tweener Madness and we are here with Anil Chawla and we are excited. He's gonna take his kids out to go play in the snow. So we're between him and playing in the snow, so we're gonna bang this out fast so he can go make some snow angels and snowmen and stuff. And Neil, thanks for taking time on a fun snow day to be with us.

00:01:26 - Anil Chawla
I'm happy to be here. Thanks for having me. Yeah.

00:01:29 - Scot Wingo
So you are part of our selection committee, which we appreciate you stepping up and volunteering. You do a ton of stuff for, which is always awesome. Tell folks that may not know your story and I definitely want to get you on the long form. You're on the list for the long form founder podcast, so don't tell all your stories, but give folks a thumbnail of your background, how you got to the Triangle, and what you've done on the entrepreneurial side.

00:01:52 - Anil Chawla
Sounds good. Well, I moved to the triangle 21 years ago, which is kind of crazy to say out loud.

00:01:57 - Scot Wingo
You're native at that point. You're native at that point.

00:01:59 - Anil Chawla
This really does feel like home. And I came here right out of college to work for IBM. Spent about six and a half, seven years at IBM, did a lot of cool stuff there, but got the itch to be an entrepreneur. Started working on things on the side and ultimately decided to leave IBM in 2010. It was a really kind of fortunate time to step out of the corporate world here in the Triangle to be an Entrepreneur because there was a lot of activity with the American underground having opened up things like the startup factory started by Chris Kively and Dave Neal, which I was fortunate to be a part of and was able to get involved with. The startup community, ultimately started a company called Archive Social and turned out to be a really kind of fortunate move for me to make the leap at the time to land on an interesting problem which is around social media and keeping legally sound business grade records of that content for businesses and organizations that were more and more putting all their communications on social media. So there's a lot there I can talk about, but kind of the gist of it is the company focused on record keeping predominantly for governments, and spent about a decade with ArchiveSocial building that up from being a solo founder to bringing in private equity, making two acquisitions, and ultimately selling the company to a strategic in 2022. So it was quite, quite an amazing journey for me personally. And once I went through that process, got involved with the startup community, I can't help but stay involved. It's just this is an incredible place to build a company. People like you have done amazing things for this community and so as much as I can help, I'm happy to do it and happy to be here.

00:03:46 - Scot Wingo
Awesome. And one question on your background. I see you're wearing a Code for America jacket and a Georgia Tech hat. The. So I assume you are on the technical side of things, are you? So did you do comp sci or computer engineering? What, what did you. Where. Where'd you start on that?

00:04:01 - Anil Chawla
I studied computer science at Georgia Tech. I did flip that hat off to bring my archive back on as we started recording.

00:04:06 - Scot Wingo
Okay. Yes. All right. Wow. Fast. You're like a Lady Gaga with the costume changes here. Cool. And then you've done. I know you've. So you left Archive Social. How long has it been?

00:04:19 - Anil Chawla
So we exited to a strategic in 22. I did step back from CEO in 19 and moved to the board, Chairman of the board at that point. So I've kind of been five years out of the. Almost six years. A little over five. I guess we're now coming into the sixth year of being out of the hot seat.

00:04:35 - Scot Wingo
Yeah. And every time I see you, I have to do my prerequisite. When are you starting your next company and how do I write the first check? So I'll go ahead and get that out of the way. But you've been busy, active, doing some angel investing. So you're an LP and tweener fund, which we appreciate and Then I know you've, I actually don't know the, the amount or any like number of investments. But I know you've done some angel investing kind of individually as well.

00:04:57 - Anil Chawla
Yeah, again it's, it, it's exciting to come out on the other end of starting a company and be in a position where, where I can now help other entrepreneurs get off the ground. Honestly, part of investing is, is again learning and growing for me and so I've gotten involved in a bunch of things, been I'm an LP in some of the local funds, including a tweet tweener and was excited to be one of the, one of the first few funders there. But for me, honestly Scott, it all comes back to how can I make an impact? And more and more I've kind of moved towards. I don't write a lot of checks anymore because I want to be able to write a check in a way that I truly kind of am more connected to the impact that I'm making. So some of the bigger checks and more recent checks I've written have been with companies that I've gotten involved with that I've started to help the founder. They've asked me to join the board or join the advisory board. And in the process of doing that I've said, wait a minute, I'm already in here. I like what's happening. I like these founders a lot. How can I get more involved? Can I write a check and invest? So I've kind of done that investment more on the, on the, as a second part of getting involved.

00:06:06 - Scot Wingo
Nice. And then in the, you know, you're kind of known as the govtech guy. You probably don't want to be, you probably didn't set up to be pegged that way. There's nothing wrong with it, but some, But I know you think outside of that space, are there any particular. When you think about companies to get involved with, is it, is it because of that category or do you like actually prefer to go into other categories? What are your areas of interest?

00:06:30 - Anil Chawla
Yeah, believe it or not, back in 2012, government was not actually the sexiest industry to get involved with. It may not be now either, but certainly back then there weren't even a lot of gov tech companies kind of found, found my way there because the problems in that space are immense and the impact you can make is really tangible. Right. In terms of what government does for us as a society. So I do find myself getting involved with startups, companies oftentimes because of that angle. Again, it's all about where can I help other than just writing a check. And given the experience we had at Archive Social and then including acquiring some other companies, I have a lot of perspective on that space. And so that's certainly an area where I can be more than just another entrepreneur on a board. I can actually help specifically with go to market and product design and things like that that are more specific to government. So I do spend some time in that area. It's not necessarily to your point where I want to be completely siloed, but I know I can make impact there. But it's really kind of anywhere. I think it's interesting and we're, you know, company solving a good problem. I can be a little bit more helpful.

00:07:42 - Scot Wingo
So.

00:07:42 - Anil Chawla
So one really good example is recently I joined the advisory board for the swing racket and paddle organization starting here in Raleigh, which is going to be the world's largest racket club. And it's not only going to be here in Raleigh, but it's a scalable model for, for, for. For beyond. And tennis is, Is a personal passion of mine. And so being able to combine, you know, my personal interests with, with the business opportunity was a unique opportunity for me to get involved with that.

00:08:09 - Scot Wingo
Yeah. We have a surprisingly large number of people in the area involved in pickleball, so there's a. There's a huge pickleball thing going on in the triangle that at some point, it's in the back of my mind to write an article about it. It's like one of those things that a set of us know, but like, I think people would be shocked how much pickleball runs through the triangle. It's kind of interesting.

00:08:26 - Anil Chawla
Yeah. And kind of before pickleball, this. This is one of the top tennis destinations in the country. And again, something that was surprising for me. I grew up a tennis player, came here, kind of stopped playing for about 20 years. And once I started playing again, I realized there's this huge community of enthusiasts around kind of racket sports. Yeah.

00:08:44 - Scot Wingo
Cool. That's good. And I know you're relatively early in on angel investing, but any, any big wins or misses that you kind of think about that you should have done or anything like that.

00:08:56 - Anil Chawla
Yeah, it's an interesting one, I think because of the timeframe. I haven't really felt like I've missed yet. We definitely have some companies that have grown up where, you know, I'll give you an example. Green Places was. Is a company that, that where I met the founder, Alex, a little late. And I know a lot of My peers were involved with that early funding of that company. That company's doing really well. So I guess that would be one where I was like, oh man, that would have been cool to be a part of that and the early funding of that. But in terms of wins, I mean, I think I'm just constantly amazed with the breadth of, of talent and expertise that we have here in the Triangle. I think just between my direct investments and being an LP in different funds, just the kinds of companies and kind of again, the breadth of those companies is just really amazing to see what we have happening just here in our local region.

00:09:52 - Scot Wingo
Yeah, I saw last night Bot Built, it was on X. There was this like cool video of robots building houses and I was like, oh my gosh, I've got to send that to the Bot Built guys because it looks just like what they're doing and it was them. So I was like, wow, that's pretty. And it was gone viral kind of. I can't even remember what account I saw it on, but it was like one of the bigger accounts and it had like, you know, 600,000 views. So, you know, we can go from, you know, doing cool govtech, like what you had at Archive Social to, you know, robots building houses to what planted is doing green. Yeah, it's really, really. I love, that's what I love about the triangle is the, to your point, the breadth or the wide diversity of different industries that we have startups in. Cool. So. So as a fellow founder, kind of flipping over to the kind of living in, both in the founder and investment world, you probably have more empathy for, for people pitching because how many times did you have to pitch at Archive Social? Did you ever keep track of.

00:10:45 - Anil Chawla
Countless. Countless. I mean, you're always be pitching, right?

00:10:48 - Scot Wingo
Yes, always be pitching is the job. My mindset. Yeah. And the um, you know what people don't realize that watch Shark Tank and stuff is the, the hit rate is very low. So even for folks that are relatively successful, like, like, like you and I, you know, I think my hit rate is like 0.1% or something. So, you know, literally for every a hundred pitches, you're going to get like one or two yeses and you know, and, and it's so, so you have to, you know, any, any advice you can give for the folks that are on the contestant side, the founders, the eight, you know, teams that are going to be in the contest.

00:11:18 - Anil Chawla
Yeah, I think, I think to your point, like, if the success rate was really high, it'd be kind of wrong. You Wouldn't be doing something new enough. You wouldn't be pushing the edge enough as you need to with a startup. So my advice always comes down to a few things. I think one is it's always about telling a story, right? You look at a pitch deck and you have maybe the typical six to eight slides in there. It's not about covering a checklist, it's about telling a story throughout that. So one, make sure you tell a story and then two, be authentic. I think, you know, we hear this advice about from investors particularly that they invest in founders, but we almost just kind of get kind of just used to hearing that. We don't really think too deeply about that, but you really are selling yourself in that pitch. So as a founder, the authenticity around why you really care about this problem and how you got there, why you and your co founders, your team, why are you the right people to solve it? You know, how are you thinking about this in a way that's fundamentally different from what's been done before? A lot of that just comes back to your story and who you are and how you got to that moment.

00:12:32 - Scot Wingo
That's great advice. You've probably seen a ton of pitches. Anything, any advice of what not to do?

00:12:44 - Anil Chawla
Yeah, I mean, there's a lot of mistakes you can make there. So I think that's probably a whole topic. You know, I think, you know, one of the ones, One of the issues I see oftentimes with, you know, first time founders is because they are so deep in the problem and they know so well is it's hard to then step out of that and realize that your audience is maybe hearing about this problem space for the first time. Right. And so being kind of too assumptive about what you're saying actually makes sense. Getting a little too deep, a little too nitty gritty and then sort of transitioning into the product. Like you really need to nail what the problem is for an investor, audience or an audience that's not you. People really need to understand the pain more than anything. I think in pitches. Oftentimes we as investors kind of give entrepreneurs the benefit of the doubt that whatever magic box they're building, they can build it. We do understand what's special about the magic box and why it's different. But the idea of being able to build it, it's almost like, okay, we think you can do that, but you have to really sell us on why does this matter what real problems or why will an audience of people go out of their way to open their wallets or give you their attention for this to even be a thing. And I think a really important way of avoiding that is remembering not being stuck in this curse of knowledge you have and remembering that somebody might maybe kind of opening their mind to this problem for the very first time.

00:14:22 - Scot Wingo
I think you and I are both tech founders and other tech founders have this. You know, we, we get so excited about the problem we solved at a technical level. We want to spend time explaining that. And to your point that if we don't, if the investor doesn't understand the six steps to get there, you're kind of wasting time to, to explain like, why this really cool solution existed, you know, to what. What problem and why. And. And yeah, so that's good advice. Cool. Anything last you want to add to folks before they see you live in the. So we'll be recording live in the studio and then these will drop over time and folks will get to kind of see you on there in that environment. But anything you want to say to the contestants or our viewers?

00:15:02 - Anil Chawla
Yeah, just a word of encouragement to the entrepreneurs. This may be the first pitch for. For many of you, and it can be kind of scary and you might just want to get through it. As we, as we kind of joked about a few moments ago, like, this is, this is the day in the life of the founder. And I remember doing my first pitch way back and in January of 2012. And it's exciting. It's kind of like playing a sport.

00:15:27 - Scot Wingo
Right.

00:15:27 - Anil Chawla
You might get really nervous before you show up on the field or the court, but that's kind of why you do it. And so I think for all of you who are showing up for Tweener Madness, that this is just an exciting opportunity. I commend you for doing it and channel that nervousness into that passion that you have. And this won't be the first time. Right. Especially as you're successful, you'll be pitching a lot.

00:15:50 - Scot Wingo
You know, the other good thing is everyone in the triangle is super nice. Anil, if there's a scale of nice and Neil's like a 12 out of 10, so. But everyone's kind of in that 10 zone, so we don't have any Simon Cowells or Mr. Wonderfuls that are there to kind of like create drama by tearing you apart. So. Yeah, yeah. So there's very little risk in this that we've designed this format to be very friendly for early stage founders. So. So hopefully that that helps relieve some of the stress.

00:16:14 - Anil Chawla
So I'll double down on that. I think I'll say the thing I was most surprised about in terms of becoming an entrepreneur is just how much people are going to go out of their way to support you and how much people want you to win. So that's been an amazing part, at least in this community of the journey, and excited to see that manifest at Tweener Madness.

00:16:33 - Scot Wingo
Awesome. Well, thanks, Anil, for doing this on a snow day. Hope you go out and have fun with the kids. Throw a snowball for me and we'll see you live in the studio in about a week.

00:16:44 - Anil Chawla
All right, looking forward to it. Thanks, Scott.

00:16:50 - 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.