Triangle Tweener Talks

00:00:03 - Alex Lassiter
If you start companies thinking that you're gonna leave everything open to chance, like, I don't know anything, and I'm gonna just learn it as I go. But every decision is like, to me, it's just like a. It's like an unwinding of something that I originally thought.

00:00:21 - Voiceover
Welcome to Triangle Tweenertalks, a weekly podcast by builders for builders, where we explore the startup journey from the idea to the exit and all the lessons in between, with an exclusive focus on founders from the triangle region of North Carolina. Tweener Talks is produced by earfluence. Now, here is your host, serial founder, and general partner of the Triangle Tweener fund, Scott Wingo.

00:00:44 - Scot Wingo
In this episode of Triangle Tweener talks, we have Alex Lasseter. Alex is a local, multi time founder, and in this conversation, we really spend a lot of time on his backstory, where he grew up, his high school experience, and his time at University of North Carolina. And then he worked for a consultancy and then started a startup called Gather. So we get to hear all the great stories that led up to then getting back to the triangle and starting green places. I hope you enjoy this conversation as much as I did. I've talked to Alex a lot about green places, but I have never had a chance to hear all these great stories that he had. And talking to a lot of founders, every founder has these types of stories where they're, like, on the hair's edge of failure. Sometimes they fall over that edge, and sometimes they don't. So that's what's the most fun to me about talking to other founders, is hearing these stories. I hope you enjoy it as well.

00:01:41 - Alex Lassiter
I grew up in Charlotte, so just in South Charlotte, kind of what used to be on the line of the edges of town and has now been kind of consumed by Meckleberg county. Cool.

00:01:51 - Scot Wingo
And then. Anything special about upbringing? Was your dad an entrepreneur, or did you have entrepreneurial thoughts early on or that came later?

00:01:59 - Alex Lassiter
I think I was like, I was always, like, an idea minute person, you know? And I don't think, you know, for a lot of kids and for a lot of people, I think I always was very envious of people that knew what they wanted to do. Like, I was always the kid who was like, I wanna do all of these things, you know, I think. I think I wrote, like, a thing in second or third grade about how I really liked Leonardo da Vinci, not because he was doing cool art or whatever, it was, just because he just got to do all the things, like. And I just wanted to be an everything person and just do all that. My dad was a lawyer, and so I was like, those kids in school were like, I'm going to be a lawyer, or I'm going to be a doctor. I'm going to be this. I'm going to be an astronaut. They knew what they wanted, and I was always stressed because I never really did. But my dad was an entrepreneur, is in high school or maybe middle school. He left his practice and started a staffing firm, got some investors, and I didn't think about it like that at the time. I just probably just, I think, absorbed kind of what he was doing. But I was always into doing things and always have been. I started a charity in high school. It was called brick by brick. It was a bunch of buddies of mine, and the idea was we were going to collectively pull all the. We were all public high school kids, so we were going to pull all of the public high school seniors or graduating seniors. Instead of doing a senior gift to the school, we thought, we're going to do a gift to the community public schools. Your education is paid for by everybody else. And so what we did was, we raised a bunch of money. We got to go in the field. I have a giant check. I got to go in the panthers field and receive, which I carry around with me everywhere. It's amazing.

00:03:42 - Scot Wingo
How much did you raise?

00:03:43 - Alex Lassiter
We raised $78,000.

00:03:44 - Scot Wingo
Holy cow.

00:03:45 - Alex Lassiter
And then we built a house. So the idea was we were going to build finance and build a house with habitat for humanity for, um, uh, for somebody who needed it. So we had, like, 15 high schools represented in North Carolina. We. We raised the money, like, right before the end. Um, and then got out there and actually, like, put shingles on roofs and build the house, and it's. It's still there. Um, it was really cool.

00:04:10 - Scot Wingo
Very cool. Awesome. So then, um, you got out of high school, and you decided to go to Carolina? Yeah, yeah. North. University of North Carolina, for those that.

00:04:19 - Alex Lassiter
University of North Carolina, yes, exactly. Yeah.

00:04:21 - Scot Wingo
The. I'm a South Carolina grad, if you think of that reference. We call ourselves the Carolina down there. Super confusing. And then when you went to UNC, what did you study and had you kind of drilled in on entrepreneurship or still wanted to be a renaissance man?

00:04:34 - Alex Lassiter
It was still an everything guy. So I came in, I took all kinds of classes. I ended up going to the business school, the undergrad business school, I think largely because, again, I didn't know what I wanted to do, and I think I was just trying to push in a direction of something that I think could lead to an outcome. But I did a lot of stuff in college. I was a Moorhead scholar, so I got to travel everywhere. So I was teaching English in China. I was climbing mountains in Wyoming. I was just doing all kinds of stuff and kind of got exposed to a lot of the world pretty quickly.

00:05:04 - Scot Wingo
That moorhead scholar, you have to apply. It's very competitive at that point. Was there an interview?

00:05:09 - Alex Lassiter
Okay. Yeah. So it is really competitive. And it's funny. We went to a pretty big public high school, and schools in North Carolina get certain numbers of nominations depending on how big it is. And at the time, our school had four nominations and I didn't get any of them. My mom at the time was like, if you've already filled out the application, it's like a 20 page application, so you might as well just send it in, because what they do is they have a pool that comes in from the feeder schools, and then they have this sort of general pool. She's like, you have no chance. If you didn't even get a nomination, you're probably not going to get it, but you've already done all the work. Why not? So I submitted it in directly with kind of the general pool. Got an interview, kept getting interviews, kept going to the next stages. And I like to say I was like the last guy in the door, but I was like, the last guy in the door, and none of the people in my school got it. And it was awesome. It was a life changing experience.

00:06:01 - Scot Wingo
Yeah. I didn't know you at the time, but I imagine you being quite a precocious senior in high school.

00:06:05 - Alex Lassiter
I think it was always really good at talking. I wasn't good at written stuff. I think my satan, we had to do the written thing. It was like a new thing. And the feedback was, needs remedial english help.

00:06:17 - Scot Wingo
So I have that. No one can read my handwriting, so I don't know what I'm saying.

00:06:21 - Alex Lassiter
This guy, he's got something, but it's not, it's not really. Doesn't really fit. So, you know, I always felt like I was good at relating to people, and I think a lot of it is just, I just. I like people. I like to talk to people and I don't have a big ego, and I just. I just generally enjoy hearing from people and talking to folks. And so I just kind of felt like if I could get in the room, then I. That was going to let my, you know, personality shine. But the, the written piece of it and everything else probably wasn't as good as most people were. So cool.

00:06:49 - Scot Wingo
So that's a full ride, right?

00:06:50 - Alex Lassiter
That was a. Oh, it's crazy. Full ride. Four summers I traveled in Europe for. For almost nine months, sleeping on the couches. Met my wife out there. We just. I saw everything. It was amazing.

00:07:03 - Scot Wingo
Very cool. And then did she. Was she on a similar kind of a.

00:07:06 - Alex Lassiter
She was studying abroad in Florence, Italy. I had studied abroad for a semester in eastern Europe and Prague and basically just stayed. And so I was writing this research report, which is kind of one of the summers that you did. It was following jazz shows all over Europe.

00:07:22 - Scot Wingo
That was your research report?

00:07:24 - Alex Lassiter
Yeah. Somebody sort of crafted towards what I wanted. She was like, are you really interested? I was like, oh, I'm interested in traveling, but this kind of works. Anyway, I was just going town to town. So I'd have, like, a festival in some random city in Italy or in Croatia or Montenegro or something like that. And I would email people ahead of time on this website called couchsurfing. And what they would do is they'd basically respond back and say, yeah, you can sleep on a couch. And it was free. And so I did that, and I was bouncing around, and I was in Montreux, Switzerland, at the Montrose jazz festival. And I think I was just homesick. I was just like, I gotta go. I need to get out. I need to do something and see people that I knew. And a lot of my friends were studying abroad in Italy. But what I did was, I went to bed that night. I sold the rest of my ticks to the show. I went to bed one night, and I decided, I'm going to send out two requests on couch surfing. So one would be towards my buddies, the people that I knew in Florence, and the other was to go to Pamplona and do the running of the bulls. And I thought, this would be like a 20 year old. So this 20 year old thinking, and I was like, whichever one responds first, I'm getting on a train. I'm going. And they responded first. So I came down, and I met Anne that night. I got there, saw my friends. We went to a Yin Yang twins concert, which I went to Carolina the other day and told the story, and they said, who's the Yin Yang twins? I thought, man, that's crazy. But I met her there, and we started dating a couple weeks later. First date was at a van Gogh exhibit. You know, it's been downhill since for her. So we met. We started dating two years later, two months later. And we've been together since 2008, so awesome.

00:09:03 - Scot Wingo
Yeah. So your choice was you could have either gotten gorged by a bull or met the love of your life, one of the two. Yeah. I think you chose wife.

00:09:09 - Alex Lassiter
Yeah. You know, you gotta know what you're worth. You gotta leave it up to fate.

00:09:16 - Scot Wingo
Cool. So you come back from all that and then you're out of school, and then did you go through the normal job search thing? And I did get your resume on the portal at Carolina and all that, Jess.

00:09:27 - Alex Lassiter
I did. I had a professor, you know, who said, you know, consulting is sort of like the everything guy job. You know, he said, this is something where you can kind of work in a bunch of industries, and we thrive on people who are smart, but, like, don't know what they want to do. So I applied to a number of places and got a job at Bain and company and did an intern summer there and then got accepted to do a full time. But in the interim period, a buddy of mine that I traveled with had started a company out in Seattle. And he said, you know, your job isn't going to start until the fall. Why don't you just come out to Seattle and you come work with me and see what this is all about? So I was like, all right, that sounds great. I've never been to Seattle. And so I flew out there and I was working at a company called intern Match. And I was their first intern. And we were, we. I mean, it was like, it was like a tv show. Like, there was three founders and me, we slept in the house that we worked in. I slept under the desk of the, of the VP of engineering or whatever, you know, his title was. We paid him in Diet Mountain dues. So that was his, that was part of his stipulation, was a Diet Mountain Dew. And I remember there was like an argument because his supply, he would come and work through the night, so he'd get there at like nine and he just worked through the night. And so if the diet Mountain Dew wasn't there by like nine, it was like a big issue. And one time, one time it wasn't and it was an issue.

00:10:49 - Scot Wingo
But we do anything cool with the cans. Those kind of people are like. They do like pyramids with the cans and all kinds of stuff.

00:10:53 - Alex Lassiter
Yeah. I mean, it looked, I mean, it looked like a desk like this and it was just a pile. I mean, it was just an incredible efficiency of Diet Mount Dew. And he would work through the night and he was super smart and we had a, we had a great time. I did a pitch. The thing they let me do was a pitch competition. So there was like a, like a local kind of startup pitch for investment type thing. Winner get like ten grand or something. And I'd convince them that they should let me do the pitch. And then at the end I'll surprise them and tell them that, you know, intern match trusts intern so much that they let an intern do this pitch. And I nailed it and we won the whole thing. And it was awesome. And I was like, this is the best life ever. So then I went and worked for Bain for about a year and a half. Different experience, but it was good. It was really cool, but a little different.

00:11:41 - Scot Wingo
You got very good at PowerPoint.

00:11:42 - Alex Lassiter
I'm super good at PowerPoint. I mean, that's a defining skill in my life.

00:11:46 - Scot Wingo
Yeah, yeah. We worked a lot with eBay, and they had John Donahoe, who was the CEO of Bain, probably when you were there, he came to eBay and all they started doing was working on slides. Cause he, like, it was all about, like, presentations.

00:11:57 - Alex Lassiter
There's a handbook. There's a handbook like you. I mean, it's like these, these colors are these way. These had a private version of PowerPoint that was only exclusive to them. And after you left Bain, you could buy it. And it had kind of special charts and all kinds of stuff that we would use. But, yeah, that was, you know, the thing about it that's that I think is really interesting because I actually learned a lot of bane and really enjoyed it. But, like, so much of getting something to work or getting people to believe in what you have is how you present it. Like, the best idea in the world of presented poorly, it just doesn't get the message across. And so they do that for a reason. And it really does work. Like, learning how to communicate clearly is really hard. It's about taking just really complex things and drilling it down to what people care about. So, yeah, I made a million slides and I still made a million slides, and it was really, really good training.

00:12:47 - Scot Wingo
Yeah. So when you were at Bain, where were you? And were you working on a certain vertical or did you cut across verticals?

00:12:51 - Alex Lassiter
So I was in Atlanta, and for those who don't know, there's bain and then there's Bain Capital. So Bain is like the consulting kind of McKinsey like company. And then there was Bain Capital, which is private equity company, but Bain's like Bain consulting. Secret sauce was like, they were number one in private equity consulting. And it was kind of like a SWAT team of people who would work in the private equity practice, which I did, and they'd basically, a company wants to buy a company, they would say, we've kind of done our due diligence, but we're going to give Bain four weeks to kind of give us their readout. What's the market like? Is this a good idea? Is it bad? You know, interview a bunch of people and swot analysis.

00:13:32 - Scot Wingo
Go do a swot analysis in a.

00:13:33 - Alex Lassiter
Short amount of time. And basically, sometimes they made the decision or they didn't. But, like, we would work on cases that were really, really fast, really long hours. And, you know, you'd start a meeting with, like, what do you know about the chicken wire industry? And within four weeks, you had to be able to explain to somebody the next ten years of the chicken wire industry. So I worked in for pretty much like 14 or 15 months, case after case after case, and I did everything. I mean, and I think one of the things that I think kind of drove me towards, like, what I do now, I learned that there's a million ways people make money. Like, you know, in college, you would ask me, I would have said, you either do marketing, you do sales, you know, you're a doctor profession, something like that, or a banker. And, like, that's the whole, those are it. Those are the only things that people do. When I left Bain, what I learned was like, you know, people can create things of value. And it's many times those are the people that are the most interesting, that are just kind of like finding something and making it. And we worked. Gosh, we did everything we did. One time they paid us to go up and down the east coast and go to bojangles. So we were working on a deal where they were trying to decide if they'd buy bojangles. And so we'd have breakfast, lunch, dinner, and late night at bojangles. Churches, popeyes, chick fil a, everything. And we would sit in bushes and jump out. Cause, you know, the signs say no solicit like we were soliciting. So we would just, like, jump out and be like, hey, like, why did you, like, why did you buy it here? You know, was it that the biscuits were, you know, fluffier or whatever? And we'd have to write down that quote. We'd have to go through the drive through and, like, mess up orders and come back and see if they got it right. And then at night we would, um, we would call these guys up in Boston and they would say, you know, what did you learn? And we'd say, well, that, you know, this guy said that the biscuits were fluffier and they're like, oh, fluffier biscuit. Can you describe the fluffiness? And, you know, they're writing it down and it's like showing up in a deck somewhere. Yeah, we had all kinds of stuff like that.

00:15:30 - Scot Wingo
Sounds like almost as good as the jazz. Jazz research. Yeah.

00:15:34 - Alex Lassiter
Tell you that boberry research, the best one I did, and it's reflective of my comments earlier about cold calling. But when I was an intern, the case that we did was basically an extremely open. This is 2009, so it was an open ended thing of like, basically this company did data analytics, and what they wanted a pain bain to do was to determine where it would be the most effective. So, like an analytic solution, like, where could we sell this? And we had this partner who sat across the table and was like, you're going to do like healthcare, like, you're going to do like banking. You're going to do like credit companies. And this is like individual people. So everybody had their own thing and mine was like government. And so I'm 19 years old and I have to, like, figure out if this analytic solution that I don't even understand what it would, would be applicable to the government. And I spent a week trying to figure out how much money the Department of Defense spent on data analytics solutions. And I cold called the DoD for, I think, 7 hours of phone tree. So this person talked to so. And so this person talks seven. I was sitting in a room just calling con calling because I kind of know how much they spend overall, but I have to know, like what percentage? And finally I got to this guy at the end and I said, you know, how much do you spend on credit and data analytics? And he said, I said, are you the right guy for that? He said, yeah, I am the right guy for that. And I was like, okay, been on the phone for 7 hours, like, how much you spent on it? And he was like, he just said, the only thing I can tell you is that my name is Dave. And I just like, wrote down the quote and I was like, I'm done. So I took him back and I was in a deck. The only thing I could tell you is my name's Dave.

00:17:13 - Scot Wingo
Promotion.

00:17:14 - Alex Lassiter
Yeah, exactly. Yeah, yeah.

00:17:16 - Scot Wingo
Interesting. Okay, so then you did Bain. You're in Atlanta. How did you end up getting into your first startup there?

00:17:23 - Alex Lassiter
So a lot of these companies, you tend to do it for a couple of years and you go off and do something in a business school or something. So I had known that I was going to go off and try something different. And my idea was I was going to be a venture capitalist because I decided that that was the coolest job you could ever have. I went out and interviewed a bunch of VC's. I got to the final interview of a big SFVC big name guy and I get in the final interview and we kind of go through the whole thing and he says, what questions do you have for me? Which was like, that was always like my, like, you always have an answer. You always have a good question. So my question was like, if I come in here and I bust my ass and I'm the first guy in and last guy out and I learn and do everything that you do, like, am I gonna be you? And he leaned back and just said, absolutely not. He was like, he was like, what do you think? Like, you think I was like an analyst at a VC firm. I like, started like, you know, echo sign or something like that. Like he said, I guess he's like, I went out and started something. He was like, you've taken a very risk averse path your whole life. You came out of school, you went to the best job, then you just kind of did that and you get promoted and whatever. He's like, you haven't taken any risks. He's like, you're never going to make anything if you take risks. He's like, sure, you should come work here and you can be smart and all that stuff, but you'll never be me if you don't do something. And so I went home and I quit Bain and I had a buddy who was kind of in that same boat and we both quit like a couple days from each other, had a terrible idea and went out and started it, you know, so that was kind of the, I would say it was like a rip cord approach. Yeah, it was a naive 21 year old ripcord approach. Like, guy tells me to do it. All right, whatever, fine, you know, tell me. I can't take a risk. Like, fine, I'll just, I'll just quit my job.

00:19:14 - Scot Wingo
Were you married at this point?

00:19:15 - Alex Lassiter
No, I'll still date naeh.

00:19:16 - Scot Wingo
Okay, all right.

00:19:17 - Alex Lassiter
Unfortunately, I married to the same person. Yeah. Yeah.

00:19:21 - Scot Wingo
So she knows she was getting herself into.

00:19:23 - Alex Lassiter
She probably knew the tip of the iceberg, but she didn't know where his head is.

00:19:27 - Scot Wingo
Is that what became gusto or so?

00:19:31 - Alex Lassiter
No. So the first idea we had was called frequenter. And I won't go through all these ideas, but the first one we have is called frequenter and it was supposed to be like, a. A better yelp. And that was what we started on, and we pivoted that business within three months. Like, three months later, we were like, Google already did something like this. And we're like, not. This isn't going to work. So then we pivoted to another company, also called frequenter, and we did that one for about a year and a half, and then that didn't work. And then we did three other companies. We had one company called table now. And have I told you this story?

00:20:05 - Scot Wingo
No.

00:20:06 - Alex Lassiter
All right, so table now. So this is, like, this is 2012 or something?

00:20:11 - Scot Wingo
This is when open table.

00:20:12 - Alex Lassiter
Well, it's funny you ask. So it was when hotel tonight came out. So hotel tonight came out, and it was like, this is it. This is, like, last minute reservation. So we said, let's do that for restaurants, since at a hotel tonight, we'll do table now. And it was this app that we built, and basically, it was only open for, like, three times a week. So, uh, if you logged on the app, it would just sort of have this little, like, guy that would kind of, like, check his watch and stuff and count down. And then Friday evening, it would buzz, and it would say, okay, like, you know, table now is live.

00:20:48 - Scot Wingo
So kind of like, what we call a drop.

00:20:49 - Alex Lassiter
Today it's a drop Friday night, Saturday night, Sunday morning for brunch, and we had, like, a group of friends that were, like, using it and stuff like that. And it was pretty cool. Like, you just, you know, you kind of, like, said, this is the type of food I want. You know, this is how many people I have. And you can only say, like, I want to eat now. And when you press that, the app would spin, and it would tell you last minute reservations that are available, and then you could book them, and you could go do it. Well, we didn't actually have that technology, so what actually happened was every Friday night, we would sit in the office, me, Nick, and Tom, and Nick and I were upstairs, and we had, like, a bunch of phone numbers on the spreadsheet, and Tom was, like, on the computer. And so when somebody would press the button, he would trigger the app to spin and pretend like it's loading. And then he would yell upstairs and say, scott wants dinner now. And he prefers Mexican. And so Nick and I would just power dial. And, hey, this is out to table now. Do you have any reservations available? If they said no, he'd be like, hang up, and we'd go to the next one, and we would just go down until we found three that said yes. Then we would yell down to Tom and say, like, these three restaurants. Tom would plug it in, and then it would be like, surprise. We found you through reservations. And then when they clicked one, then he would yell back and be like, Scott's coming now. And then we would call the restaurant and be like, Scott, I'll be here in 15 minutes. And we did that every Friday night and Saturday night and Sunday morning for, like, two months.

00:22:14 - Scot Wingo
Yeah.

00:22:14 - Alex Lassiter
And eventually we call it MVP.

00:22:18 - Scot Wingo
Today's fancy language. So I call it hamster nut. Most people call it sneaker nut, but.

00:22:22 - Alex Lassiter
Yeah, finally, we got to the point we got to start making money. We got to start monetizing. Anyway, so we did our calls or whatever, and Saturday night, we sent some guy to a restaurant, and I sauntered into the restaurant on Sunday morning and said, hey, I'm Alex at table now. You've probably heard of me. We've been sending reservations over. Our free period is over. We'd like to collect money for the reservation, and our rate that we had told them was, like, $2.50 per diner. And I came in, and I was going to collect my $5. Cause they had two people, and this guy. I mean, like, the people I know, I mean, this is, like, two years out. I'm very poor at this point, and I knew a lot of people. And so I'm, like, at this nice restaurant where there's people that I know sweating, like, you know, just not in good shape and been up all night doing this stuff, and this guy is like, I'm not paying you a dime. And I was like, yeah, but they came. Like, they did, you know, look at. Look at me like I'm trying to do a job, you know, like, look at me. And he was like, you know, pull out the receipts or whatever, and they download the receipts and came back, and he was like, this person only ordered a dessert. I'm not paying you a cent. And I was like, are you kidding me? Like, I was like, I can't even get this guy to pay me $5. And so I came home and was like, guys, I don't know what good looks like, but, like, this is definitely not what success looks like. So we close table now, basically, that day.

00:23:50 - Scot Wingo
Yeah. Interesting. Cool. How did that then? So you're in the restaurant business.

00:23:54 - Alex Lassiter
So every idea. This is a long story, but every idea sort of has, like, sort of a 90 things didn't work. One thing did, and, like, let's go explore that.

00:24:01 - Scot Wingo
So, yeah, what was the hook that got you on the hook for that.

00:24:03 - Alex Lassiter
One is we can't run a business if we can't control reservations. We can't be in a business where like, we can't. We can't control the product that we're selling. And Tablenow, we had no path. At one point, we were going to do a movie phone thing. We were going to use Twilio to make the phone calls, but we just couldnt control the inventory. And so it made it really hard for us to actually be able to sell. And what we found in the process was in a restaurant. About 70% of the reservations are handled by opentable or resi now. But restaurants will have excess capacity, usually to the tune of about 30% that are reserved for parties. And they'd never planned those reservations on opentable. So if you wanted to do a happy hour or a wedding or a corporate event or private dinner or anything like that, that was inventory that Opentable did not manage.

00:24:55 - Scot Wingo
Yeah, it's usually gated, like in a different room, like physically gated as well. Digitally gated.

00:25:00 - Alex Lassiter
That's exactly right. And there's lots of reasons why, like, because a restaurant runs on just in time inventory, and they know that a private party will drive in not only just guaranteed revenue, but it's a higher profit margin. And so there's a calculation going on in every general manager's head that says, could I fill this room with regular seats or could I fill it with a party? So they're always making this decision on whether or not they're going to open that space up to the public or not. So it makes it really hard to make those reservations and it makes it really hard for a restaurant to be able to kind of manage it. So we basically said, okay, we're going to build a business around that problem and we're going to try to go get that inventory and eventually be kind of like a marketplace where you can go and book these events online.

00:25:48 - Scot Wingo
And is this you, Nick and Tom?

00:25:50 - Alex Lassiter
Still me, Nick and Tom, the three.

00:25:51 - Scot Wingo
Musketeers on that one?

00:25:52 - Alex Lassiter
Yeah. Yeah. Anne and I, at this moment are living in a attic above a chinese restaurant in Atlanta. And it had one window with a window unit on it that couldn't close. And every evening the wind blows in Atlanta because it's so hot and it would blow trash into our house.

00:26:12 - Scot Wingo
And mosquitoes probably.

00:26:13 - Alex Lassiter
Our house was so small, it had no doors in the room or whatever we were in. And I'm only five nine and my head touched the ceiling and everywhere, with the exception of the very center of the kitchen. So she was really excited that I was going to start something else at this point.

00:26:30 - Scot Wingo
She's like, how do I hitch my wagon to the start?

00:26:32 - Alex Lassiter
She's like, it started out pretty good, and it just keeps getting worse. So we worked a lot. So, I mean, a lot. And we really were, like, had no money. I mean, none of us had.

00:26:42 - Scot Wingo
So you had this idea on inventory then? Did you start an LLC and, like, do all the right things or you kind of, like, realize we had, like.

00:26:48 - Alex Lassiter
A lawyer and he'd kind of, like, build little, like, vehicles and stuff for us. So this was, it was running as a C Corp or something like that. And so it was a real, you know, it was a real company. Just made no money, but we were all financing ourselves. Like, we got it. We had little family and friends, like, two years before that gave us some money to just, like, go out and try to live. But, like, I mean, every day was deep in the red.

00:27:11 - Scot Wingo
Yeah. So you're at the tail end of that probably, too.

00:27:13 - Alex Lassiter
We are at the nothing. I mean, we had already gone through the long conversations of, what are you gonna do? Maybe I'll go to law school or maybe I'll see if Bane will have me back. Or I, you know, I mean, it's just, it's a really dark time. Like, we just, we had nothing. And meanwhile, all of our friends were driving nice cars and, you know, they'd still stay to Bane and they're making 250,000 a year, and we're like, I can't even afford. I used to drink these beers called simpler times that we would buy at Trader Joe's that were $2.99 a six pack. They had, like, sand in the bottom of them. I mean, it was just a crazy experience. But the blue chicken thing was because we didn't have any money, we would work in this, this, this office that this guy let us rent. And it was in not a good part of town. And every day we had like a, like, you, it would be like scott's day to provide food for me, nick and tom, and we had a crock pot, and so you'd bring in something and you'd put it in the crock pot and cook all day, and then we'd break at like eight and eat and then go back to work and. 08:00 p.m. 08:00 p.m. yeah. And the blue chicken story was basically one time Tom, he discovered that you can buy beans cheaper if you buy them dry because canned beans are very expensive.

00:28:30 - Scot Wingo
This is how, you know, you're poor when you're, like, doing the dollar per bean calculation.

00:28:34 - Alex Lassiter
So he had found this recipe where he could basically, for, like, $3, feed us for, like, two nights. And it was this big thing of black beans, really discounted chicken, and we would just put it in a crock pot. And he didn't. We didn't know how to do that, so we didn't know how, like, you know, wash stuff and everything. So anyway, he cooked it, and it came out to be this, like, blue chicken, because, like, the chicken took on the color of the unwashed beans, and we just ate it and just silenced, like, this is it. Like, this is.

00:29:07 - Scot Wingo
Did it kill you on the other side or you survived the. You didn't get salmonella from it?

00:29:11 - Alex Lassiter
You know, at that time, I mean, everything was probably killing me. You know, I just. It was just. It was a dark time. It was just one of those moments where I was just like, man, you know, you had the high point of being in Seattle and kind of doing all fun stuff. Like, I'm in the depths, you know? It was not a fun person to talk to. I remember I'd go to events, and people would ask me, and I was like, startups suck. Like, this isn't. This isn't fun at all. Like, I'm not. No one's giving me money. I don't have anything. Like, you know, I can't even talk to my family about this. They're. They're like, they don't even ask about the business. They mainly just are like, you know, do you feel like you're done? You know, like, you know, I get the. I get the honey.

00:29:46 - Scot Wingo
I don't give up yet.

00:29:47 - Alex Lassiter
I get the, you know, honey, you know, you've really. You done. You've done a great job. You know, you said what you were gonna do. Like, it might be time to grow up and start to do this. So anyway, one more idea, which was. Which became gather. And, you know, again, we had. We had all the girlfriends together, and we said, you know, we're gonna kill this business. And they were like, good. I'm proud. And you're like, but we have, like, one more idea we're gonna do. And they didn't even talk to us. They were like, that's not a good idea. But that was the inventory. That was the inventory. Yeah. Private events. We were gonna basically build a way to make that easier. Like, the way the restaurants manage it is they use this thing they call the Bible, and so it'd be like a giant six ring binder of every private party or wedding that would happen, and this one person would do it, and we were gonna make that digital. And, you know, we built our first, very first version of that in a pretty short amount of time. It was basically a calendaring tool.

00:30:48 - Scot Wingo
Did you learn to code at this point, or was some of your co founders coders?

00:30:51 - Alex Lassiter
Tom was a coder.

00:30:52 - Scot Wingo
Tom was a coder.

00:30:53 - Alex Lassiter
So Nick and I were generalists, and we didn't have a coder, and I. Probably the best sale I did was tom. Like, tom was a guy. Like, I went on LinkedIn and I just started. It was right when people could used to put in, like, what they did, and I was just, like, typing in words like python, like ruby on rails, like, all that kind of stuff. And he popped up, and he was about four or five years older than I was, but he was in my fraternity, so we had, like, known each other through my brother, and I called him. I was like, hey, I heard you do python. And he was like, yeah, I'm getting into that. And that's kind of what I'm interested in doing now. I think he was, like a defense contractor or something at the time. And anyway, I talked to him for 5 hours in the philadelphia airport on the way to my brother's bachelor party, and by the end of it, he was like, you know what? I'll come down to Atlanta, and I'll come check it out. So he flew down to Atlanta, stayed in the kitchen, and by the end of the weekend, he was like, this is great. But by the way, the business, he said this was great. On was like, table now. He was like, this is great. And we're like, no, it's not, but I'm glad that you believe in it. So he became our technical co founder, and so he built all the original code, but we. I forget what month it was, but we had kind of already had all these conversations of, like, we're all going to go back and, you know, go back and move in with parents and, like, figure something out. And it's probably two years into the experience. And we had this calendar tool thing, and we booked a meeting. Booked a meeting with a local restaurant called Murphy's, just, like, on the corner in five in Virginia Highlands, which is where I lived. I met with the owner and did my pitch, and he said, this seems pretty interesting. How much would you charge? And I was like, anything, but I was like, $80 a month. And he said, I think I could do $80 a month. And I was like, great. I closed my first deal ever. That was the first deal ever closed. And he said, you guys take on any financing? And I was like, oh, yeah, we got tons of people, but we just haven't pulled the trigger on anything. And he said, well, if there's room, I'd like to invest. I'd put in 25 grand or something. So I came back to the office, and I said, nick said, how did it go? And I said, well, great. He wants to buy it, and he wants to give us 25 grand. And Nick said, all right, well, let's get him to sign this. So we printed out a convertible note, and I went back and was like, sign this. And he signed it. Then I came back and said, we raised $45,000, and that's how you knew.

00:33:26 - Scot Wingo
You were onto something. It was easier than the $5.

00:33:28 - Alex Lassiter
We went to the next demo guy, Fred Casalucci. He was kind of our age. He was kind of starting in restaurants and stuff. He said, it's pretty good. I'd buy it about 70, $80 a month or whatever. And I said, it's funny. The first guy I met, he bought it on the first demo, and then he told me he want to invest 25 grand into it. And he was like, well, who was that guy? I was like, that's Tom Murphy. And he said, well, if Tom does it, I'm doing it. And then I gave him the thing, and then he signed it. So then we were like, we closed two deals. We had first two investments from customers and stuff, and then we had probably seven to ten days to basically cobble together anybody that was remotely interested in giving us money and pulled in, I think, probably close to 200 grand. We had one guy that was, like, kind of, like an angel type person. His name was Stefan. He was amazing, and he was like, if those people would invest, like, I'd be kind of stupid not to. But meanwhile, like, my bank account was at zero. I mean, I didn't have money to pay the rent. Ann was kind of working, or she was working, but, like, we didn't have anything. Like, it was going to zero. And so all these deals, I was like, if we don't get this money, like, I'm not, like, there's no. There's no. Like, my personal Runway is, like, a week. Like, I don't have. Like, we can't even deliver this thing. And so if that money hadn't hit, like, it would have just never worked. And I remember at the end of the month, I was kind of just like, ignoring my landlord, you know, because I was waiting for, like, all the checks to clear to, like, hit my bank account.

00:34:57 - Scot Wingo
The dude that owned the chinese restaurant downstairs. So probably a little aggressive.

00:35:02 - Alex Lassiter
Not a nice man. So I think, like, I mean, I remember when we, we got that place, the guy was like, this is not fit for two people. And we were like, well, we need it for two people. And anyway, the money cleared, and, you know, I got a. Not really a paycheck. I think I got, like, $1,000 or whatever it was. Let's just put it right in his hands. And we were. We were revenue, cents. I mean, it was like, every day was like, this is it. This is all we need to do. And so I was just absolutely annihilating the phones and doing everything I could to just, like, sign deals. Cause it was truly like, if we didn't, you know, we would. We wouldn't. We wouldn't make it.

00:35:37 - Scot Wingo
Yeah. What year did you start? Gather?

00:35:39 - Alex Lassiter
This was 2012 or something, so I was probably 26, 24 at the time. Great. I mean, it was a great experience full of even more just stuff I always talk about, like, you know, you always hear the startup story. Like, you know, I was at Harvard and had this great idea, and, like, it's Napster. Like, we were like, not that we were the exact opposite of that. We were like, everything we do sucks, and nobody likes it, and nobody will give us money. And this is the hardest thing ever, but we just kept grinding. I mean, it was just, like, an insane amount of, like, work that would go into doing this. And Nick would kind of, like, develop out the product with wireframes. Tom would sort of build a product, and I kind of did all the other stuff, and we just kept going and going and going.

00:36:23 - Scot Wingo
Did you do titles, or were you like, the titleless founder kind of thing?

00:36:27 - Alex Lassiter
I mean, at that point, no, like, at that point, nobody. We were just like, we're Nick, Tom, and Alex.

00:36:35 - Scot Wingo
Sometimes you're so busy, you don't even have time to.

00:36:37 - Alex Lassiter
It just. Yeah, there was a point where we started to discuss, and Nick, at this point, was more interested in the CEO. I'm going to go raise the money. I'm going to go do the product stuff. I'm going to build out the. And all that stuff. I'm going to go out and sell a billion people. I'd run sales and customer experience, and I'll get them all through that. Then, Tom, you just make sure that the software works and you keep doing what you're doing. And so we ran like that for a long time. You know, it was interesting because I think, like, coming as a generalist and I had this conversation with people all the time, especially smart people. You know, they want to come into a startup and say, like, I'm really smart. I can do anything. And when you're in a startup, you're like, I don't need people who can do anything. I need somebody who can do one thing. And, you know, I always tell them, it doesn't matter if you're really good at those other things. What you need is somebody you can trust. You can do those things. Like, I eminently trusted that Nick would make really good decisions on his side, and he imminently trusted that I'd make really good decisions on my side. And because we were journalists and both smart, when we came together and would try to figure something out, we both really trusted each other's opinions. So if I felt strongly, then it was going to weigh, and if he felt strongly, it would weigh too. So it worked really well from a partnership perspective, but we just really had to specialize, otherwise there was just too much to happen. You know, a company with three people has as many functions as a company with a thousand. Yeah, it's just three people do them. Like, it's not that these functions don't exist. You know, there's still partnerships, there's still accounting, there's still hr. All those things exist. It's just like, it just all flows to three people. Whoever's on the table.

00:38:12 - Scot Wingo
Yeah. So then did you guys raise more capital, or is the convertible. Note it.

00:38:18 - Alex Lassiter
So basically, we got to the point where we could go out and raise, like, what we call as a series a, which today people would probably call like a seed or something like that, from a San Francisco VC. And we talked to a bunch of people, but ultimately got hooked in with this group called Storm Ventures. At the time, I remember we sat down, he just said, he said, guys, this is the most cash efficient business I've ever seen in my 20 career. I've never seen anything like this. He was like, do you realize that if your salespeople aren't 97% quota attainment, it's completely underwater? And we were like, no. And he was like, I thought that an outbound. We were only outbound. He was like, I thought an only outbound team really needs 20 to deal. He's like, your ACV is like $890, and it's all calling and virtual sales and all of that. And it's just one of those things where I look back and I was like, there's just no way that was the smartest way to do it. But for us, it was just like we were just kind of going from what we had. I mean, we bought this book called predictable revenue, and that was literally like, how to do sales as a dummy. And so I just read it at night. I was like, this seems like a good idea. I'll just do this. And so I just followed that thing exactly, and it worked pretty well.

00:39:33 - Scot Wingo
Did that mean just like raising the.

00:39:34 - Alex Lassiter
Prices or all predictable revenue does is it basically said it was started by this guy. It was written by Jason Lemkin, and who started Saster and echo sign or one of those things. And basically it's the whole idea of an SDR model. You know, this many calls, this many meetings, this many demos, it just turns into a machine.

00:39:56 - Scot Wingo
Bookings per rep and all that. Kind of the way to measure a go to market team.

00:39:59 - Alex Lassiter
Exactly. It's what I was thinking of as like, money ball for sales, where it's like, it doesn't matter how good the seller is at the end of the day, it's how good, how many leads can you feed them? And as long as you can feed them an infinite number of leads, you know, and everything else works, then it will drive more money at the end of it. And so we really, really lean into that, because none of us had sales experience, like, notice ever worked in a company like that. So.

00:40:19 - Scot Wingo
Yeah, but the guy that told you that invested.

00:40:23 - Alex Lassiter
So the guy that told me about predictable revenue, I was the guy that.

00:40:27 - Scot Wingo
Said, this is the. If you don't earn 97%, I don't remember.

00:40:30 - Alex Lassiter
I say this because I don't remember which Vc it was. I think it was. And I told this to Red Point. Cause our red point led our series a. I think it was red point. I'm like, 99% sure it was a red point final interview. And so I have a couple people that I think I know who that was, but it wasn't. It wasn't limpkin.

00:40:47 - Scot Wingo
Okay, so you did your series a. How much was that?

00:40:49 - Alex Lassiter
So we raised, I think, two and a half or 3 million and on like a, like a ten or twelve, and which we thought was incredible. Like we were, we were it. You know, we'd made it at that point.

00:41:02 - Scot Wingo
So that was what, what year?

00:41:04 - Alex Lassiter
That was probably, gosh, maybe 2015 or so, 2015, 2016. So we'd already been kind of out there for three or four years, just sort of like financing the business with upfront annual contracts. I mean, that was basically the whole.

00:41:22 - Scot Wingo
So you started in 2012. You said 2022 before. I didn't think that.

00:41:25 - Alex Lassiter
Excuse me. Yeah, 2012. Yeah, got it.

00:41:27 - Scot Wingo
So that's when you started gather and then three years later raised your series a. Yep. Yeah. Yep.

00:41:34 - Alex Lassiter
We made every mistake in the book. But, like, the smartest thing that we did, I remember we had this preconceived notion that if you're going to sell in restaurants, you have to own New York. That was like, our thing. We knew that for a fact. You got to own New York. It's the only way restaurant stuff works. You win New York when everything else, that's how open table worked. But there was a competitor of ours that was really good in New York, and we basically, it was like, Alex is going to move to New York. So I would fly up to New York on a Monday, and I would just walk around New York just taking in person meetings, in person meeting after in person, trying to sell as many deals I possibly could. And I come home every week with nothing. I mean, I'm like, you know, stayed in a terrible hotel, you know, in the terrible part of town. I'd come home with nothing. We did it about four weeks in a row. And I came back and I was like, nick, like, I'm getting crushed up here. You know, I don't.

00:42:27 - Scot Wingo
Competitor had already, like, totally.

00:42:29 - Alex Lassiter
It wasn't novel. It wasn't novel. And it was like, who do you work with? Like, these guys work with, you know, Danny Meyers groups and these guys work with all the Michelin stars. Who do you work with? And, like, well, we work with, you know, like, Tom Murphy's, you know, down in Atlanta, and they're like, I don't even know who that is.

00:42:42 - Scot Wingo
Go home, Hill. Billy. Yeah.

00:42:44 - Alex Lassiter
So I came home and I was like, man, like, look, like we've got two options. Like, I understand that. Like, we got to win New York. But, like, option one is like, I can just continue to grind it out and I'll go up there every week and I'm just going to go in a knife fight every single time. And I got to beat these, like, incumbents. Or we could just say it. We're never going to New York. We're going to go everywhere else. We're going to go to every other market, and we're just going to go where we're the only person who's ever done this before, and we're going to clean up, and then one day we'll come back to New York. And when we do, we're going to say, we're a national brand and everybody knows us, and then we can go do it. So we just crossed out New York and San Francisco on our sales force, and we went to Chattanooga and Nashville and Austin, Texas and Boulder and Seattle and Portland, and we pitch or move.

00:43:33 - Scot Wingo
So wherever they are, go surround them.

00:43:35 - Alex Lassiter
We basically, yeah, we called the oil drop method. We were like, we're just going to go in all these different places and eventually, you know, we'll be the people. And, man, we, we aced it. I mean, everywhere we went in these mid market cities, we were the only people in. We could just go through. We'd win all the best deals. There's no competitor. And then a couple of years later, you know, we were now pretty big. You know, we had caught up to triple seat. They had, um, you know, multi year lead on us. And we kind of caught up in probably the same, you know, size of revenue or roughly close. And we said, all right, now we're going to go take a New York.

00:44:05 - Scot Wingo
So it's like five to 10 million, 2030. Like, we're, we're in the zone of revenue.

00:44:09 - Alex Lassiter
So in this point, we're probably in like the five 5 million range.

00:44:12 - Scot Wingo
And this is like maybe a year or two after the, like 2017, 2018 kind of thing.

00:44:16 - Alex Lassiter
It's like right around that time. Yeah, it's right around that time. Gosh, we still never really got New York. I mean, we still try to do it. We ended up acquiring triple circumental, you know, and that's ultimately how we did. They were embedded in there and they had a good solution, too. But if we hadn't made that decision, we would have never been able to succeed. And I think the interesting thing about that business, and now I'm seeing it at green places, is you start companies thinking that you're going to leave everything open to chance. I don't know anything, and I'm going to just learn it as I go. But every decision is like, to me, it's just like a, it's like an unwinding of something that I originally thought, you know, when we were originally selling, you know, gather, we, we thought, you can only sell restaurants in person. That's how restaurant people are. So we did that for a while and it didn't work. And, and then we talked to these guys down in Charleston. People matter. And they said, what the hell are you doing? Like, we sell everything, you know, remote. We sold subway remote. And we were like, oh, okay, we'll do that. And then it started to work. And I, you know, restaurants will only pay monthly contracts. They'll never pay up front. Eventually we started to ask people for it and they said, oh yeah, of course we'll pay upfront. We're happy to do that. And it's just like all of these things, you gotta win New York, but you really don't. And so it's just a lot of these unwinding things that I think had we been too obstinate to, like, if we believed in what we thought too much, then I think we would have never really got there. But probably because we had failed so miserably for two years, nobody ever felt like the idea they had was a good one.

00:45:46 - Scot Wingo
Yeah.

00:45:46 - Alex Lassiter
You know, it was at best sort of a test and an idea.

00:45:49 - Scot Wingo
Yeah. Cool. So then tell us. Let's wrap up gathering on, make sure we get in the green places. So tell us. So. So you got big enough, you acquired your competitors. That was good.

00:45:59 - Alex Lassiter
So we acquired the competitor after Vista. But basically what happened was we had gotten to the point where we needed to raise more money and we were going to raise a series b, but we didn't feel like we had a strong enough case to go get a b. So we went back to storm and said, what do you think about doing a little bridge round? And they were like, look, we're supportive of you. We'd happy to do a bridge round, but why don't you go out and test market? Because I think you guys probably could. So we went out and we started talking to people and lo and behold, we did have a lot of interest. And Vista came calling and said, we've got a whole playbook on your business and we'd like to take a majority stake.

00:46:36 - Scot Wingo
Yeah, so this is Vista Equity, a private equity firm, and they either do buyouts, so they buy 100% of something or like a 51 52% kind of a thing.

00:46:44 - Alex Lassiter
And they own c vent at the time. And cvent was just this juggernaut business. And that's one of the reasons why they had a file on us, which we didn't really realize until later. But they knew a lot about our business.

00:46:53 - Scot Wingo
And I think you touched the event space. We touched the space tangentially.

00:46:56 - Alex Lassiter
Exactly. And basically, yeah, they just opened up a new fund where they were going to start doing still majority investments. But it was like more flexible for like smaller stuff. And I think we were one of the first few companies that actually did that. Now they do a lot of those things, but at the time it was very unproven for, for vista. They were very like, we're going to buy info blocks or.

00:47:15 - Scot Wingo
Yeah. And the pitch to entrepreneur is stay on. So we're going to. We're going to get you some liquidity. So we're going to buy more than half the company. You get some money off the table, and then there'll be a. And then it gets really complicated. But you'll own some equity in this new thing sometimes. And so. So you'll get kind of a double shot. So, yeah, yeah, and they'll put some money in there and then you'll. You'll kind of get to still be the team and run.

00:47:33 - Alex Lassiter
And what we said was, yeah, they gave us, you can sell this amount of shares, you know, but the rest, you know, needs to roll in. And we're going to buy out the rest of the cap table. We're going to give you this amount of money and you can go run the business. And basically, like, the way Nick and I kind of looked at it as entrepreneurs is we're on paper still really poor. I mean, we're still in the attic. And increasingly we'd be out dinner with investor types and lawyers and all that stuff. I mean, we'd be out to dinner and, like, they'd like. And the check thing coming around.

00:48:05 - Scot Wingo
Yeah.

00:48:05 - Alex Lassiter
And, like, I couldn't cover the check. So it was like this dance of, like, who's gonna pay? And I didn't want to be ungrateful, but I was like, if I pay that bill tonight, like, it is not as problematic.

00:48:15 - Scot Wingo
You get really good at, like, not looking at that half of the table because the bill is over there. And if you contact with that thing, you're gonna.

00:48:21 - Alex Lassiter
And we go back. You would go back to my house or Nick's house and, you know, go out to a dive bar or something like that and just talk about it. And it was just like one of those things where I was like, 99.99% of all of my net worth of everything that I've ever done is living in this equity. And while I'm hanging out with CEO's and successful people, we're different. When they're talking about going to visit the Turks and Caicos, I'm like, I've not left Atlanta in a really long time and I don't have a path to do that. And it's this mismatch. And one of the things that we liked about the Vista deal was like, we were able to get cash off the table, which is really important for us because one is it, like, it allowed us to be able to live like, we could actually live and actually start to do things. But in our decision making, when you get to that point, you're no longer making long term decisions. If you're that levered up in your own business compared to your own personal wealth, it's impossible to make the decisions that are needed to make. And what we basically had talked to ourselves about was like, I can't even run this business the way that it should because I'm too afraid at this point. Like, when we started it, I had nothing to lose. Now I have everything to lose. And so it was weighing into everything that.

00:49:41 - Scot Wingo
Yeah, gotta be conservative because that's your nest.

00:49:43 - Alex Lassiter
Exactly.

00:49:44 - Scot Wingo
Can you say like the zone that that first deal was in? Was that like a. Yeah, so that was.

00:49:50 - Alex Lassiter
So. I think the valuation they put on us was like somewhere in like the 65, 70 million. It was a good, healthy valuation. Realistic compared to where we were. We were able to cash out a.

00:50:02 - Scot Wingo
Percentage of our shares, which you had some vc. So they got their piece.

00:50:07 - Alex Lassiter
They got their piece, they got paid. The night that we did that was like the best night ever. Me, Nick and Tom went and bought large pizzas ourselves and the nicest bottle of wine we could find, each of us. And then we sat in a room and we called all these guys that invested in like, frequenter, like, called Tom, you know, Murphy, we called Fred, we called. And I mean, it was like, I mean, we're, we're talking to people who were like, I didn't even remember what the name of this thing was because.

00:50:38 - Scot Wingo
They probably invested in this thing at 5 million and they got a ten x or something like that. They invested way less than their 25k became. 250k.

00:50:44 - Alex Lassiter
Yeah, 25k, they got 40 x return.

00:50:46 - Scot Wingo
Wow. So these guys were like, so 25k became a million.

00:50:50 - Alex Lassiter
So we, I remember I talked to one guy and he was like, he, he was in the middle of a, of a food lion and he just starts like, you know, dropping the f bomb, you know. And I was like, what is it? And he was like, he's like, he's like, he basically, he was like, I lost my job because like, I had a heart condition and the stress was too much. I'm basically like, north of food stamps. I'm buying. He was like, I'm buying discount meat right now at food Lionde. And he was like, I haven't had a job in two years. And he was like, this is gonna save, this is gonna change my life. He's like, I can't wait to get home and tell my wife and all that stuff. Tom was telling me that something fell in his restaurant, and it was gonna. Basically, he'd overextended his restaurants. And he was like, this could, like, end this business. Like, this is my family business for 30 years. I'm not gonna be able to afford it. And he was able to pay for it.

00:51:41 - Scot Wingo
Anyone not believe you?

00:51:42 - Alex Lassiter
No, no. They were. They were like. It was more like, I didn't know you guys still existed. Like, it was like. I don't remember what this. Like, what was the business called? Like, it was like that. Yeah, it was like the I did what moment? And we would just, you know, you're about to get $800,000, so, like, give me your wiring instructions. I'm sending it over. I mean, it was awesome.

00:52:01 - Scot Wingo
Yeah, I had that one time where I told someone they were gonna make 800, and they were like, they had put in, like, twenty five k, and they're like, oh, man. Well, at least it's not zero. And I was like, eight hundred k? And they're like, yeah.

00:52:10 - Alex Lassiter
What? Yeah, yeah, yeah, yeah. It was awesome. And we had early employees. We got to do that stuff, too. We call them in, like, here's 250,000 or whatever. And this is a really cool moment.

00:52:21 - Scot Wingo
Awesome. So then you sold half the business to Vista, and they have this kind of really famous playbook rule of 40 and all this jazz. So you got to kind of learn all that. How did that go?

00:52:32 - Alex Lassiter
You know, it was good. They're really smart. Like, what I would say about Vista was, like, really, really smart people, and I think they learn really fast. I think when we started, there were things that, you know, again, we were, like, one of the smallest companies. We were definitely the youngest founding team that they had, I think, ever invested at the time.

00:52:48 - Scot Wingo
And were you 30 yet?

00:52:50 - Alex Lassiter
No.

00:52:51 - Scot Wingo
Okay, so you're. No.

00:52:53 - Alex Lassiter
2007, I was 29, 28. And, in fact, when you're a millionaire.

00:52:59 - Scot Wingo
By the time you were 30.

00:53:00 - Alex Lassiter
That's true. Yeah.

00:53:01 - Scot Wingo
It's wild.

00:53:02 - Alex Lassiter
I went to the Vista conference. Like, they do a conference every year in Carlsbad, and it's awesome. And they, like, paint a new. They basically create a Vista hotel, and you're hanging out with, like, the CEO of, like, marketo and the infoblox guys and ping identity and, like, all these people. And vista buys, like, the whole hotel for the weekend.

00:53:18 - Scot Wingo
Yeah.

00:53:19 - Alex Lassiter
And I, like, I went down to the cocktail hour, and, like, they denied me, like, a glass of wine, and I had to, like, go back out to my room and, like, get a passport and be like. I'm like, real like, I'm still able to drink.

00:53:31 - Scot Wingo
Isn't their CEO kind of wacky? And he's, like, really into fly fishing and stuff, and they always do these events where he can fish or something.

00:53:37 - Alex Lassiter
It was one of those incredible experiences. I saw a guy get a plane on stage, like they had. When we pulled up at the first one, they had like, four or five cars out front. It was like a Ferrari, Lamborghini, whatever. And the license plates were like, fund one, fund two, fund three. I think one of those guys, like, was, like, friends with Drake. So, like, Drake would play and stuff. Like, Neil degrasse Tyson was hanging out. Like, he was just, like, walking around all the time. Like, it was just crazy stuff and so much success. I mean, these guys were cranking out three, four x returns, and so it was a good experience. I think they had to learn a lot of, like, our stage. So there's a lot of things where I was like, you know, let's come to the session and learn about how to sell to, you know, how to manage millennials. And I was like, well, I'm a millennial and all of us are, so I don't really need this, you know? And they're like, let's talk about, like, implementing, you know, workday. And I was like, we're not going to implement workday, but they learn fast. Like, they do really learn fast. And they were able to help us with a lot of things, so.

00:54:37 - Scot Wingo
All right, so you're at Vista, you're doing the whole thing. Did they. So you bought one of your competitors. Give us a synopsis of what happened post Vista. And then ultimately you're going to decide to leave.

00:54:47 - Alex Lassiter
Yeah, so I was there. I was there for about two or three years post acquisition. We're trying to grow, we're re implementing new stuff. We're now at the point in the business where, like I said, our acv was like, at this point, I mean, it's like $1,700. But to grow millions year over year and to continue to achieve a growth rate, we had hit a really hard point where we were so heavily reliant on outbound sales and low acvs that to be able to get to those, it was really hard. And so we had a, um. We had a tough year. Like, I mean, it was a tough year. We had brought in extra help. We had all kinds of folks in the business trying to, like, do things. I think a lot of the mistakes that I made, um, and I think a lot of the executive team probably would agree, is, I think we, like, assumed the identity of us being a much bigger company than we were. Like, I think we sort of, like, now that we were, you know, a vista company, we want to act like it. You know, we wanted to make the decisions that these guys make. We. We kind of lost, I think, a lot of our obvious decisions. The way I described it was I would walk into meetings and then be like, where's your PowerPoint? And I was like, I didn't get my PowerPoint in today, but for years after that, there's no PowerPoints. You're just going in, you're talking about stuff. And so I think we had a lot of challenges in kind of getting to that next phase of growth for us. And the business would grow, but just not really at the level that we really wanted it to. And meanwhile, triple seat was in a fight with us. We were about the same size, and it was like we'd steal one of their clients, they'd steal one of our clients, and we'd steal a balance.

00:56:27 - Scot Wingo
At this point, we were like, 20 million or so or.

00:56:29 - Alex Lassiter
No, no, still smart. No, we're probably. Gosh, I don't know. We're probably in the 710 ish type range. And basically, we just. I mean, it was just like back and forth and back and forth. And I think on a personal piece for me, like, this is the time I started having kids, and I didn't want to be in Atlanta. Like, that's not really where, like, my wife and I, like, we really liked Atlanta in our twenties, but we wanted to have kids in Raleigh. That's where we wanted to live. And we had kind of had a number of discussions related to family and family health and kids and stuff. And basically I was like, you know, I think in the nicest way possible. She's like, look, like, I put up with this. Like, you know, I've done my part and I've supported you through everything. You know, there's got to be a time where we can go and, like, set up roots. And because we knew we wouldn't be in Atlanta forever, it was hard for us to do that. And, you know, I ultimately said, guys, I got to move up to Raleigh, and I got to figure out a way to make it work remotely.

00:57:29 - Scot Wingo
Why Raleigh? Was that just from your time in Chapel Hill, or does your wife have a connection to Raleigh?

00:57:34 - Alex Lassiter
Yeah, my wife's from Roxborough, and a lot of her family lives in Raleigh, so she's got multiple siblings. We're all close, and they've got, we got nieces and nephews and stuff like that all in here. And so we just decided that that was the place, like, where we wanted to be. Like, it was kind of the best of all the things. And it was always in our plan to go. It was just one of those things. I think this is where a lot of entrepreneurs get stuck, is, like, you get so good at just, like, putting your head down and moving forward that you don't take a look around and be able to stop. You know, you get these guys that are like, if I don't make another 100 million, I'm never gonna do it. Like, and it's like, it just. You just keep being unhappy. And so I think what Ann was basically kind of helping me understand is, like, your life is still existing. You've done a great job. You can still grow a great business. You can be a part of this. You can do all the things you want to do, but, like, you know, we want to have a family. Like, we want to, like, have our life as well. And at some point, you've got to start, you know, investing in that. And so we made the difficult decision to come up here, and I would say, like, we made it work decently well. The travel started to get to me a little bit of, like, especially as the kids got a little older.

00:58:43 - Scot Wingo
What year was that?

00:58:44 - Alex Lassiter
This was 2019, I would say. And it kind of got to the point of, like, if you're not going to be in Atlanta, like, we're going to build everything here, and it's just not going to be the right place to do this. And so we parted ways, basically, the end of the year, 2020. 2019. Going into 2020.

00:59:07 - Scot Wingo
Covid. Spoiler alert. Covid's coming. So this is probably not a terrible decision.

00:59:11 - Alex Lassiter
Well, when your business is literally, like, defined by large party reservations at restaurants. At restaurants that need to be open, our business was illegal. And, like, every. Like, I mean, of the simulations, I mean, to have your business model be completely illegal and to lose like that. Right? Like, to be like, okay, I'm gonna lose because. Not because my product's not good, not because people don't want it, but literally, what you sell as an illegal thing to offer was crazy. And it was a lot of stress because I still owned a lot of equity, so I wasn't involved, but I was a lot of equity in the business. And, yeah, when Covid happened, I mean, I was. I was pretty convinced it was going to zero, you know, and I would say that that Vista did a really great job over that period. So right before that is when we bought triple seed, so we doubled the revenue of the company. When that happened, the headcount dropped off very quickly, which was really tough and really hard. But they were like, look, this is to save the business. We have to get to profitability very quickly and have our ability to wait this out. And at the same time, one of the things that our software did was we collected credit cards. So if you booked a restaurant for a wedding or something like that, a lot of times you have to give them a physical number and they hold onto it. Well, if you read the stories in the news where they were like, you know, I plan my wedding, but like, the venue is going to hold on to my deposit. And they didn't cancel it, they just said, we'll just push it out. Those were the companies using gather, like, and if they didn't, they weren't able to do those things. And so when we would talk to restaurants and stuff, they were like, look, like 30% of my revenue is living in your software, and if I drop your software, I kiss all that money goodbye. Exactly. So they basically were like, heres the deal. Were either going to go out of business or if we dont, were going to have to have your system in place because we need to have all that money back. Thats what happened. They didnt sell a lot. They sold some, they didnt sell a lot, but they basically gave payment forgiveness to a lot of these people. They battened down the hatches in terms of profitability. They just waited it out and said, look, if the restaurant industry recovers, we're going to be the best people to position to win. And that's exactly what happened at the tail end of COVID It started to come back out and people started to pay again and they started to buy things. And the business was a million times more profitable than it was. And then suddenly growth and growth and growth. And meanwhile all of our competitors went out of business.

01:01:40 - Scot Wingo
That takes out all the small stuff.

01:01:42 - Alex Lassiter
And the business is a juggernaut. It's an amazing company.

01:01:47 - Scot Wingo
Did you sell your equity or you still got a piece of that?

01:01:49 - Alex Lassiter
No, I kept all of it.

01:01:53 - Scot Wingo
Has vista traded it around or it's still.

01:01:57 - Alex Lassiter
Back? About a year and a half ago, General Atlantic bought it for 500 million and that's when I took all my equity out.

01:02:05 - Scot Wingo
Yeah.

01:02:06 - Alex Lassiter
Good.

01:02:07 - Scot Wingo
Was that a good transaction for you?

01:02:09 - Alex Lassiter
Yeah, terrible. No, it was fantastic.

01:02:15 - Scot Wingo
Yeah.

01:02:15 - Alex Lassiter
And I had convinced myself it wasn't going to happen, you know, like I'd convinced itself it wasn't.

01:02:21 - Scot Wingo
You mentally have to because you see all these people that spend that money and then it doesn't become money, and that's a bad thing for them.

01:02:27 - Alex Lassiter
That's exactly right. That's exactly right. So anyway, Covid's happening. It's 2020. I'm just like, having a great time. Like, I'm not working. I'd spent seven years of my life thinking about private events and catering software, which I know everything there possibly know about that, but nothing else. So I'm doing all kinds of stuff, like trying to learn an instrument, trying to learn a language. We started an investment fund, invested in spiffy and levitate and all these businesses. I just absorb things. And it was an awesome year of just waking up. And I describe it as the feeling of if you stuck your head in a hole for eight years and then you pop out, you know, everything is interesting.

01:03:10 - Scot Wingo
Yeah.

01:03:10 - Alex Lassiter
And as a founder, you get like.

01:03:12 - Scot Wingo
So myopic, you have to shut out everything.

01:03:14 - Alex Lassiter
Exactly. That's all you can do.

01:03:15 - Scot Wingo
Yeah, there's some interesting new technology. Don't have time for it. Yeah. So I can think about super, super focused. Yeah.

01:03:21 - Alex Lassiter
So basically about a year, year and a half from then, I decided that I wanted to start doing something again. Like, the investment thing was fun, but it really wasn't like what I was interested in doing. And I kind of felt this moment, I think, of, like, feeling lucky that I had a chance to choose. Like, I was like, nobody gets a chance to choose. Like, nobody gets a chance to really just say, this is the industry I'm gonna work in. You know, most of us just do what is there, you know, or, you know. And so I, you know, I thought, why not, like, do something that I think matters? And with the kids, you know, there and on the way, I thought, what would be cooler than to be able to tell, you know, your kids, you plant trees or something. So lets do something in sustainability. Lets pick a hard problem there and well just go at it from that direction. And I got in this habit of basically walking around my neighborhood all day and thinking about ideas and meeting people. So meeting with you, Jess Lipson lived like three doors down for me. So I would stop at his pool and we kind of talk about stuff and just did that for three or four months. I was like, into water technologies and all kinds of random stuff. And ultimately what we kind of kept coming back to was like, the biggest businesses in the world are going to be able to do this stuff. Like, if you really believe in sustainability, you have to believe that everybody has to do it. It just doesn't work like Nike does it. Nobody else does. Everybody has to do it. And there's a huge difference between a Facebook or an Amazon and a whole foods and patagonia and everybody else. So it's a pretty simple equation. If everybody has to do it, well, like, you know, Facebook's out at this time, like floating like solar panels in the South China Sea. Like, what the hell is everybody else going to do? And when you look at it, it's like, that's like 90% of emissions, 93% of like, Microsoft's emissions are at supply chain. Like, so these are not big companies and they aren't the people that can go pay somebody $2 million to be a sustainability lead.

01:05:19 - Scot Wingo
There's a pyramid, and the companies at the tippy top are going to be able to do it themselves. But there's, like, everybody else. That pyramid still represents a huge number of companies.

01:05:26 - Alex Lassiter
Exactly. And so basically what Jess and I came to the conclusion of is like, let's go build like a chief sustainability. Like, if these guys, this is a chart, it just said like a big bar chart. It's like these guys at the top, like, here's Amazon. And then we're like, here's everybody else. So it's like total addressable missions. And it's like everybody. And then the guys at the top, and we said, these guys have chief sustainability officers. These people don't. So let's build a software that takes the strategies they came up with and then implements them through technology so that everybody can do it. We said, chief sustainability officer in a box. Let's go out and let's build that business. And that's really where everything kind of started for us.

01:06:01 - Scot Wingo
So if you're a mid market company, you use your software, you say where you located, where your buildings, you can plug into the power utilities and pull all that, and you can get a really good idea of their footprint, their sustainability footprint, their impact.

01:06:16 - Alex Lassiter
Yeah. The way I think about it is a good analogy, I think, is to intuit. So in the finance world, you have the people at the very top who have concierge service, like wealth managers, and they make really awesome decisions. And then you have the people at the very bottom that read Dave Ramsey online and are like, I'll invest in a Roth Ira. Well, what intuit did a really great job of is if you give us all the data, if you give us all your information, well, kind of create a tech enabled middle ground. So it's not going to be as good as the guys that are getting Morgan Stanley to go read through their stuff. But it's certainly better than just reading an article. And what we can do is we can take best practices and then we can map it to your data and we can make good, informed decisions that makes you a healthier finance person. And the same thing is true for sustainability. For a lot of our companies, they don't buy green places because they want to be green. You know, they don't say, like, I want to be Patagonia, so I'm going to buy green places. A lot of times they're doing this because, like their businesses, they sell to want to buy from greener companies. It's a marketplace, you have the Fortune 500 over here that says, we're all going to reduce our emissions to zero. We want to find greener suppliers. And so they survey all their suppliers and they go look for alternatives. And then you have all these people on the other side. They're like, well, I'm willing to do the work, but if it has an outcome on the end of it. So, like, they don't have a way to sort of connect to each other. And so we sort of think about it like the way that intuit would walk you into something like this. We would say phase one is you're going to connect all your data, which is what we do. So get the data into us and we're going to tell you your score. So intuit might tell you, here's a credit score, you know, we're going to tell you, here's where your carbon footprint is.

01:07:58 - Scot Wingo
Yep.

01:07:59 - Alex Lassiter
Then with that information, we're going to try to basically give you insights that helps you be a better business. We're going to give you insights that helps you reduce your emissions. We're going to give you insights that help you identify if you're in or out of compliance with a regulation somewhere. We're going to give you tools that help you identify better suppliers. We're going to give you tools that help you share this information with other people. We're going to see if we can find cost savings for you. We're just going to use that information like the way that amend.com would to say, if we have all the stuff we have from you, what can we use from that to be able to help you stronger?

01:08:33 - Scot Wingo
You can't change anything. You can't measure. So you got to measure it really well first and then you can start moving it around.

01:08:38 - Alex Lassiter
Yeah, we have the data and we have a way to be able to look at it. And there's such an opportunity on the other side to be able to use it in ways that are effective. And so we think about, like, you don't buy green places, you become a green place. And we think about, what are the values for doing that?

01:08:50 - Scot Wingo
Yeah. So you started when?

01:08:54 - Alex Lassiter
April of 2021, the day before Earth Day, which is like a massive miss. We just waited one more day. Yeah, yeah.

01:09:03 - Scot Wingo
And you started a business on April 1, so that's kind of fun. And then you did an interesting round. So you did kind of like a club round. So explain how that came together.

01:09:13 - Alex Lassiter
Well, it really came out because Jess Lipson basically, like, came up with the idea with me. Like, he was like, the, he was the guy on that stop that. We would just sit around and talk through, like, what are we going to do? And when we had gotten to the point of, like, this seems really interesting, Jess said, look, like, if you think this is interesting, like, give a little time to it, and if you like it, then I'll invest. I'll give you some money.

01:09:34 - Scot Wingo
Yep.

01:09:34 - Alex Lassiter
So that was a fun conversation with my wife, because I got to say, I want to do this again. And she's like, no, but I was like, but Jess said, he's going to give me money if I do it. And she was like, that seems a really great idea. You know, she's like, that's perfect. She's like, you got this really smart guy, you know, and he's basically a genius, and he's interested in something about you he finds interesting that he wants to partner on this, which could you pick a better partner? And, and, and you've got to built in sort of, like, co founder relationship where you can go do something that you're both curious about doing, and, um, and he's going to help you. And it was just, like, the best decision ever. So coming back to him and saying, yeah, like, I've. I've evaluated, I've looked at it. Let's do it. Um, he said, okay, cool. Like, I'm going to, you know, fund your first round. Um, but what would be cool is if maybe we could get some other guys that would do this, too. And that's when we reached out to you and Todd at Pendo and Joe Colopy and Chaz Felix, and basically all the guys that had started software companies and basically said, this is what we believe in. This is what we want to do. Would you like to support it? And I think I certainly have a lot of belief in myself, but I think most of those guys were like, if Jess is going to do this. I trust him. And so I think his ability to, I think, have built up decades of trust really, really, really changed our trajectory and probably amongst anything else, influenced the outcome of the business for him to be there.

01:11:02 - Scot Wingo
Yeah. So let's summarize. So you did. You did kind of a seed round or a pre seed, and you did a seed which brought in Felicis.

01:11:09 - Alex Lassiter
Felicis Ventures.

01:11:10 - Scot Wingo
Yeah. From the Bay Area. And then you did red point. Yep. So how much have you guys raised at this point? Give us an idea. Like, where. Where is this? How many people in the business? Where's revenue? Kind of in a.

01:11:21 - Alex Lassiter
So we have about 40. About a little over 40 people in the business. We've raised just about $17 million. We have lots of that still undeployed. And in the bank, we're in that kind of, like, three to ten, like, meat grinder. In the business where things have really worked, we've got a great set of, like, MVP customers. Were starting to get dominance in a number of sectors. I think like, 15 or 20% of the top 100 law firms use green places. I think we now have, like, five of the top 100 staffing firms who work with most of the software companies people have heard about that are kind of in that path to becoming public, and we're starting to get a name for ourselves, and it's really working. And what we need to do from here is not necessarily new things, but it's to basically make sure that as we're growing and adding more layers in the business, we don't lose that sort of edge to results. I think this is the dangerous part. And I look back at my own history, and I think this is the time when Vista came in, and I don't want to make that mistake twice. So we're really trying to look at unit economics and make sure that we're not just pouring gasoline on something that isn't working. We just really want to build that predictability in the business.

01:12:33 - Scot Wingo
Trey. Yeah. So you've had success now, and I get this a lot. People are like, why do you dress like this? And why do you just, like, meet all these people? Why are you so. You're relatively humble, you're very approachable guy, you know, are you still cheap? Why. Why has this not gone to your head?

01:12:52 - Alex Lassiter
Well, I think it has gone to my head. I think I just, you know, I feel like I exude, you know, confidence. No, I don't know. I just. I think it's because I think it's just like a game, and it's fun. I feel like I'm playing a sport, and I wasn't really good at sports, but, like, this kind of, like, is that for me? And I just, I don't know. Like, I think I never really like people who are really, like, pretentious about stuff. I like people, you know, it doesn't matter. I don't care where anybody works or what anybody does. I just sort of, like, enjoy my life and enjoy, like, hanging out with people and. Yeah, I mean, I'm probably the cheapest person ever. I drive a. Drive an old car that has a duct tape is holding the passenger window open, which is probably not a very safe thing, you know, but I just. Yeah, I don't, like. I like spending money on things. I like to do. Yeah, I like traveling, you know, like, looking at stuff. You know, I don't need to stay in fancy hotel. Like, I like to travel and hang out and enjoy my life and have experiences. I don't get a lot of pleasure in dressing really nicely or having really nice things. You know, I think I have four kids, and that's incredibly expensive, you know, but I would spend money on them and that experience than I would with anything else. And it's not to say that if somebody was like, I don't want to have kids and I want to live in a penthouse in New York, like, they can do that, too. But I do have, like, a, like a Porsche. It's just not a Porsche. It's like four kids who eventually are going to have to go to college and stuff. Like, the money is being spent. It's just probably being spent on different things, and it's probably just how I was raised.

01:14:18 - Scot Wingo
Cool. Well, we're up against time. I appreciate you spending so much time on this. I'd never heard any of your gather stories. So those were, I've lived many of the green places stories, but we want to get those. So we want to have you back at some point to give us an update, maybe in a year or something like that, and then we can get into more of the green places stories. Thanks for being so generous with your time and sharing very candid stories for other founders. I think that will help them a lot.

01:14:39 - Alex Lassiter
Well, thank you. I appreciate it. And thanks for having me on and appreciate being part of the tweener family.

01:14:44 - Scot Wingo
Absolutely.

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