Steven Plappert - Forecastr

speaker-0: and I closed literally the day before the last payroll exits my bank account. Do not start a company on a whim. Please don't, because like it is a heavy load. It's not all sunshine and rainbows. You better be passionate about it. You better love it. You better be serious because like you get that thing going. like, especially once it gets going, if you're not careful, it's a prison. Like, let's just say it like it is. Lots of bears, black bears, you know, and they're chill. Like a moose, bears, my wife ran into a mountain lion and that's not Jill, but it didn't eat her, so whoo! You know?
speaker-1: ⁓ wow. are you doing big guy? Good good. How you doing? How you doing is the is the real question. Have you have you been through the ringer? I have.
speaker-0: happened to the ringer but I got out of the ringer six weeks ago ⁓ and so I'm Gucci man. I'm like light as a feather, know, like plenty of cash in the bank now. Like basically, basically with this last round closing we kind of got to that checkpoint of like there's not really any reasonable path to go to zero anymore unless we get really aggressive and chase, which we won't do because that's just not our vibe. It's like as long as I like
speaker-1: No.
speaker-0: Make tactical bets, gauge it and pull them back if they're not working. We'll ride this thing to profitability with that last round. And so was like, and this is the first time I've ever been there as a founder where like, it's always been like, okay, yeah, I got money, but like at some point it's going to run out and at some point I'm going have to need more. It's like, I'm finally at a where I'm like, okay, like I can take this money and see it through to profitability. And like, that's kind of a reasonable baseline now. And it's like good to great, you know? And it's like... that that whole like existential risk coming off the shoulders is I've I realized in the last six weeks is like a big deal. And I'm like light as a feather.
speaker-1: Yeah, so you're saying you're sleeping okay.
speaker-0: I'm sleeping alright dude, I'm getting a straight eight hours. you know, and even more than the sleep is like I'm waking up like, alright, rather than waking up like. You know, you know, you know, so yeah.
speaker-1: Yeah, dude. Amazing. That's so cool. Thanks for the time. ⁓
speaker-0: Well, I'm glad we made it here, man. It feels like it's been months. Everyone's like, all right, let's do it. I got to kick it out of here.
speaker-1: Yeah, no, All the things. I'm glad to... Well, and ⁓ today is an interesting day. ⁓ So you are hitting us on Stackless birthday. This is the two year from when we incorporated. Yeah, terrible twos. And on top of that, we actually, it was a two year chase to chasedaleinthe.com, but I just got it and we just launched it.
speaker-0: As of today. Let's go. I just bought Orcaster.com last week, but we have not launched it. That's exciting. go.
speaker-1: Yeah, that's amazing. ⁓ Cool. Well, so I'm excited to chat with you. What I really want to do is like, we'll dive into some of the early forecaster stories and stuff like that. But before that, sort of coming back to, ⁓ love your, from what I've done and ⁓ seen in your history and sort of where you came from, what I'd love to hear about is when I think about the entrepreneurial journey and start off and sort of what it takes. special breed of person, like the way you're sort of, you were raised and your family or, or whether it's something that was sort of built into you to always, you know, either explore or take risks or whatever it is. Like everybody's got sort of a different like recipe for what got them here. Like, ⁓ if you had to sort of start back prior to say school, ⁓ and, or family or anything, like, ⁓ is there anything in that mix that you feel like sort of teed you up for where you're at now.
speaker-0: Yeah, man, that's an awesome question. And I think there's a number of things that come to mind for me. mean, one is more nature, I guess. And that like, I've just always had, I've always had a very rich of what I would call curiosity. Like from a very young age, like I was the kid, less so my brothers. Like I'm the middle of three brothers, right? like my both my brothers are their artists are super creative and that kind of stuff but they were less like intellectually curious and creative you know and and I was like this guy was always like well why well why why like when I was five years old not to get too deep but I was like I was obsessed with like what happens when you die like and I would ask my mom I would wake up in the moonlight I go to my mom and say why what but what happens when you die she's like well you go to heaven what's that like and she's like well it's this and that I'm like well that doesn't make sense you know and I was like
speaker-1: Something's wrong with Steven. He's got to talk to somebody.
speaker-0: going, know, so I've always been this like, like, I want to get down to the root of things, I want to understand the nature of things. And so I think this curiosity leads to problem identification, the desire to solve problems, I think that ultimately would lead to entrepreneurship, you know, it's just like this kind of critical thinking that leads to like an outside the box type of approach. You know, so there was this curiosity that's always there on the more nature side. But then on the nurture side, you know, my father was an entrepreneur, and his father was an entrepreneur. So my grandfather ran Flatborder Insurance for many, many years. That was his thing. He ran an insurance company. My father was a sales director at a company that did really well and had an early acquisition. He made a nest egg. when he was about my age, he launched his own payments company. He's ran it for 40 years now successfully. so I think I had these kind of role models. And I was always curious to ask my dad about business and things like that. And so I think... That was also one of those things that like always kind of got the engine turning. So I think exposure to him, to them, you know, as entrepreneurs and kind of role models, and then just that kind of deep, that deep curiosity, you know, I think were two things that definitely, yeah, led to me kind of taking this path.
speaker-1: That's so cool. I think about like one of the things, the first thing you said about like the being inquisitive. I think that that's something that is baked in. When it's baked in, it's one of the strongest powers that it's the difference between. And I think you can learn it though. It's one of those that like I, my wife and I was sort of worked on that where like, you know, she in the sort of WordPress era, we started sort of working on websites, you know, together. And she had never really dug into that, but then all like unlocked this idea that you can ask Google and YouTube anything and that you can really sort of start to like gather. And I think that, you know, just understanding that, but when you're born with it and you're asking everything ⁓ is that's, that's amazing. such a, such a strong skill to have as an entrepreneur. And I love that being in and around it, obviously then you had the idea that you can sort of break from. you the normal traditional, you know, you've got to do this and you've got to do that and you've got to do this and you've got to do that.
speaker-0: And I think maybe the third thing for me, you know, is always this like, and again, I think at a certain level, people are kind of born with this and at certain level, maybe you can kind of view this changes too as age. like, I've always been obsessed with essentially greatness. I want to be the best. I want to be great. It's not for legacy. It's not for prestige. It's not for reputation. It's just like, for my own end, I don't know why it's there. It's just always been there where like, I've never been okay with okay. Like, okay is bad. I want to be great. And so I've always held myself to this like ridiculously high standard. And so in that sense, like I want to do great things just because I think they're great. like, and so that's just always been a big piece of me as well. And I think that also drives me towards entrepreneurship, but you have this greater opportunity to be great and to do great things or to make a big impact, you know, because you're at the, because you're, you know, you're bringing something into existence and you're, and you're creating. so I think that that like innate desire to just be great for for no reason other than just it's great. And that is the way I think about it. It's just like this guy's kind of been a part of me. And I think and I think it also drives me in this way.
speaker-1: Well, those three together, now I sort of naturally see why, you know, in your history, like coming out of school and just founding something and starting a company was like, get me to it. Let's do it. Yes.
speaker-0: Yes, yes. There's also the thrill-seeker element, like we're like, I've always been a big, I've been a big adventure guy, a big thrills guy. I like, I like to, like, I'm the kind of guy that goes snowboarding and just sends it. Like he just goes flying and maybe he'll eat it, but he doesn't care because he's just sending it, you know, and that's just always been so, and so I think that element too of like that, that really high risk tolerance, that desire for volatility. I don't want a bunch of sevens. I want tens and ones. You know, that's how I like it. You know, I like the volatility. It's the spice of life. you know, and so I think that also kind of feeds feeds into that. But my parents aren't like that. Both my parents, neither one of my parents are very risk tolerant. Neither one of them like are like are thrill seekers. They they're both like more steady eddies, you know, so I didn't get it from them. But it's just like always, always been there, whatever.
speaker-1: That's cool. Well, and interesting too, like I think there are parts of me that my dad and I sort of realized that he broke away after medical school and realized that he didn't like the sort of how, ⁓ you know, there were parts of the hospital they worked for ⁓ that it was very much like, ⁓ here's the medicines that we should start sort of pushing, you know, like that when he was coming out through. And so he went and basically took out a big loan, bought a building and ran a medical practice for 43 years. Um, and so that sort of entrepreneurial was there. But interesting, think, I wonder if it is also generational that I remember telling him, I'm like, okay, so what if you basically set up and you franchised and then you taught people how to do, and I'm like thinking about his like medical expansion and he's like, no, no, no, I'm good. Like this, this was. You know what mean? Like this was good and this is sort of set. But I was always sort of, you know, bugging him to like, oh, we could make a, and you can have different, different areas. Yeah, yeah, exactly. That's cool. Well, so like after school, I saw you started your first company. you didn't, you didn't, did you work anywhere else like sort of prior to that?
speaker-0: further. I studied math in school, so I've always been good with the numbers. I've always been interested in money and math, like math and economics. They've always been my jam. so I studied math in school. And then I had my best buddy since third grade, Andrew Busa. approached me as we were graduating in May of 2013 with the idea for a company that we would eventually start called Fantasy Hub. And it was in the early days of daily fantasy sports when DraftKings and Fandol were pioneering this ability to wager real money on fantasy sports because sports betting wasn't legal. And so you could, there was this kind of work around to bet real money on fantasy sports and it's kind of a new concept. Andrew and I both played fantasy sports and we thought there was an opportunity to just like build a company there. And it started out very much like a, we have no clue what we're doing. We know that. Let's just give it a, let's just give it a go. And if it fails in like three to six months, like, cool. We tried it. Awesome. Like we'll go get big boy jobs. That's like, that was our mentality around it. And to the credit of our parents, Charlie, his dad and my dad, Jim, they came together and they said, guys, if you wanted to pursue an MBA, we would put this money towards it. So like, here's 25k a piece. They gave us 50k in our initial cap. said, go get an MBA, meaning like start the company, right? Go get the real MBA, which is like building and experiential learning. And it was an amazing move by them that we almost squandered completely because because we spent that 50k with like a dev shop to build a prototype. They were garbage. They built the worst prototype ever. Looking back on it now is like, ⁓ my God, I can't believe what they did. And they were just taking advantage of us. We burned through that 50k. We were almost dead in the water right there. And then here comes this angel investor, Kevin Johnson out of Nashville loves playing DFS, got connected to him through one of my friends like He loves it. He gives us another 50K. We spent that one a lot better because of the learnings. We actually got a product to market and off we go for the next three years. And so it's like, we almost just like totally face planted. It's just like survive until you thrive. And that one never did fully thrive. We did fail three years in, but three years was enough to get an MBA. and to really learn the art that the initial arts, right? I'm not gonna say I'm a black belt after three years, but the initial art of building a business and would ultimately lead to the rest of my career so far. so, so yeah.
speaker-1: That's amazing. And I like, I love that, that so much because I'm, look, I'm not, I'm not anti-schooling. I'm not anti-college or, or MBA, but I am. I've talked to, you know, I have family members that I've talked to that are like, I don't know. think, I think I'll just keep pushing on business for the next couple of years, but it's always used in this sort of umbrella term, right? It's like, well, I'm going to go study some business. ⁓ and it's so different, even, even from an MBA perspective, you would have gotten. the theory of how people do things in business versus burning through your 50K, learning incredibly important, valuable lessons. And then also that networking and the 50K, the responsibility for it, how to grow it, how to get the three years, which is in my mind just far exceeds even getting an MBA that says, is how you do it once you start applying it in the future.
speaker-0: that's totally right. think there's thinking and there's doing. There's conceptual learning, there's experiential learning, and both have merit. But experiential learning, I think, is ultimately more powerful. And so think if you lean towards doing and experiential learning, in doing, you kind of must think and you think and do and you learn on the fly. And I do think the power of it is absolute, which isn't to say that there isn't power in the academic setting and in that kind of conceptual learning because there is up until a point. But it only gets you up into a point. I do think it's like the kind of like, you know, as you go through your learning, you know, kind of phases, you go really high conceptual early on, and then you start to kind of go conceptual and experiential, and then you go pretty much all experiential. And so I think there's kind of a phase shift to it in a sense. But yeah.
speaker-1: Yeah. So where did that lead to? how did that end? Did you just decide one day it was like, all right, it's time to shut the doors?
speaker-0: we did it and after waking up probably like the 45 days prior at the same breakfast table being like is today the day we shut it down? Because that was one of the things that like you know when you're shutting down a business if you've never done it before it's like it's like there isn't like an obvious day where you wake up and it's like well today is the day kill it. It's like it's this slow death or it's like every day you get more and more like it's like the writing becomes stronger on the wall and like and it's and you get kind of more and more insolvent right you get more and more like ⁓ you know. And it's like, then essentially it just, it's like everything in your, every fiber of your being is telling you to like push through the wall, find a way through it, keep working on it. You know? And so it's like, it's a weird space, but like, but how it, but obviously the play that to that is like, mean, once we got that money from Kevin, like I said, we use it to get a better, better product into the market. We use that to actually get some nice initial traction. And then we were the first Kentucky based company to ever get selected into a Techstars program. which is really cool for me as a native Kentuckyan and there's been plenty since and it's great to crack that seal. And in 2015, we moved the company down to Austin, Texas to go through Techstars. And that was a huge unlock for me just like going through Techstars, meeting all these mentors, meeting all these successful founders, like soaking it up like a sponge, just like, you 23 years old. it's just, it was just like the veil had been lifted, man. I felt like I didn't know everything, but I went from like, from like unconscious incompetence to conscious incompetence. All of sudden, I knew all the things I didn't know and I was able to pluck at them and learn them in a way that before I was like, it was totally opaque. And so that was just an enormous ⁓ time in my life, super, super fun. But then a year later, we did ultimately fail. We had some good traction, but it was nothing that was going to knock everybody's socks off. And at this time in the market, there was a lot of legal turbulence, lot of cease and desist letters from AGs. lot of like, this thing even going to be around? Is it going to regulate it? Like what's going to happen? And so the investment landscape totally dried up, rightfully so. Like I was like, nobody should have touched this business and nobody did. And I mean, we, we, we, we had like a couple hundred K and commitments, but it wasn't going to be enough. So we didn't take them, which was a great call. We shut it down, which was a, which was a great call. We frankly shut it down too late, which was a bad call just cause like, you know, we didn't want to shut it down. We were younger, like let's push, let's push, let's push. By the time we shut it down, it was more messy than it had to be if we would have shut it down earlier. So it was a whole learning experience like how to wind down a company like, you know, because there's a there's a there there and nobody teaches you how to do it because everybody wants to talk about the winning, not the losing, you know, and it's burly. Like, I mean, you shut that thing down and it's like, and that was three years of my life and I poured everything into that thing. Fantasy Hub was a deep, deep integrated part of me that was now dead and just decaying off my body. And it's like, and it felt like it felt like a piece of me had died and and it felt like It was an intense experience for me too because like I did grow up in a household that like my dad, like we were well off, like you know, like we were well off. We never needed for anything big time, you know, and it's like, and I was always like pretty, pretty smart and pretty athletic and like never the most popular guy, but I had plenty of friends. And so I always just kind of breeze through life. And like fantasy was the first time I like, I applied myself in full to something that I failed at. And it was an important moment for me to like, to reflect on that and to build off that adversity and to strengthen my resolve. And so like that the months that came to pass that failure were really heavy. It was kind of the only time in my life where I ever dealt with any kind of like really true like kind of extended state of depression. But then I emerged with it. From like a Phoenix I felt like it was just like what doesn't kill you makes you stronger. And then I'm like I'm so grateful for that experience and what it was. And I was like, and I was never liked the idea that you take somebody's money and you lose it and all that kind of thing, but it's just part of the game. so, yeah, that's kind of how it all all shook out, you know.
speaker-1: love hearing, you know, obviously the the shutdown story and you had a difficult period afterwards. And I think that is so hard because you you give you not only give every fiber trying to figure out how to like keep this going and you wake up and you you but you live it and you breathe it and you've also wrapped your ego and yourself in this cloak of the brand that you basically are trying to birth into existence and then to not have that work is such a It's so much more core and essential to your yourself than it is if you were just to work somewhere and they said, you're not doing great. We're going to fire you. It is so much more different than, basically swimming upstream for three years and then having someone be like, uh, I don't, don't think so. Um, Love the fact. I love the fact that also.
speaker-0: especially the first
speaker-1: And I can't wait to where we get to where you're at now. think for other people to hear that like, we actually had another ⁓ Andrew booze who we, who I talked to ⁓ an episode or two ago had a very similar situation and basically went in the whole, you know, two or $300,000 and then, and then, ⁓ and then did it, but sold it. And after selling it immediately had that same sort of like, ⁓ you know, What do I do? Who am I? What am I doing? know, and I think that, you know, entrepreneurship being so closely tied to the fiber of who you are and what you can do is it's nice to see and hear the stories after that, that like, that's not just it. That's not the end of the story. Like this is where we go on to the subsequent chapters.
speaker-0: 100 % and I'll also just say, you know, I think it also needn't be so as well that you do wrap your identity in your company. It's easy to do it. If you let it happen, it will do it. If the business wants to consume your identity and if you don't push back against that, it will consume your identity. It did mine with fantasy hub, but then you fail one and it hurts and you rip it off and like me and Forecaster, it's a totally different relationship. Forecasters also And I work super hard to make Forecaster awesome and a great company. And like, I would be very sad if Forecaster didn't work out. But the big difference is like Forecaster is a company. That's all it is. It is a company. Quite frankly, it doesn't matter. the end, you know, it doesn't like what matters is like my health and my family and the love that I share with those that are closest to me. That is ultimately what matters. That is what is you. And this other thing is just this thing that you're doing. it's a very clean line that I draw these days where like Forecaster is like, is going places is going so much better than the first one. But if it did die, it would be totally different for me. Would it hurt? Yes. Would I be sad? Yes. Would I be really disappointed that I didn't create, you know, a success for my investors and for my employees and stuff like that? Of course I would. But I really don't think I would go through the identity crisis that I did the first time because like because I've evolved in my thinking around it and I've and I and I I and I and there's more of a separation there between Stephen Plapert and the CEO of Forecaster and Forecaster itself.
speaker-1: Yep. Well, and also the age differences, I imagine, between the experience that you've had because when you first do it coming out of college, I think most anybody coming out of college is coming into this world and into the society going like, all right, how do I make my mark? How do I make it like people to know about me? Like I'm going to make something. And that's so much more sort of close to the bone than it is after you've had a ton of experiences and you go, ⁓ This is a thing separate from me. Like it's a thing I'm doing, but it's not me.
speaker-0: 100 % man, it's like when you interact with a kid and they just attach to stuff, everything feels so real. like, you know, if like you're in your high school and you have a breakup and you're like, my life's over. You know, then it's like, because it feels so real when you're that young and you're that kind of naive really to use a harsher term or you just whatever, you don't have the perspective. And then you get older and you get that perspective and you say, okay, like.
speaker-1: You'll find anyone again.
speaker-0: There's a base here and as long as that base is good, I'm good. Everything else, you're in the bonus. know, it's like, don't sweat too much, you know, whatever. So anyway.
speaker-1: So what did coming out of that, like what was a bit of the slingshot rising as the phoenix?
speaker-0: super cool how life works. love all these things and life is so cool. So for me, I'm like in that depression, know, I'm like, man, this is a bummer. And I'm working through all that reflecting and I'm coming out of that and I was like, man, know, like biggest, biggest like theme in my life, biggest joy of my life is the great outdoors. I am a wild man. I'm a naturalist. I love rolling around the dirt. And I'd always wanted to hike the Appalachian Trail. And fantasy of failing, you know, I was like, you know, like this is a moment. Like I could go hike the Appalachian Trail. I don't have a job. Like I could go do that. And I was like, OK, I'm going to do that. And luckily, my girlfriend at the time, now wife, was like, I'm down to do that as well. And so me and Emily decided we're going to do a thrice at the Appalachian Trail in 2017. Business failed in March 2016. It was a little late to just like to hard shift up to that experience in 2016. So we said, OK, we'll do the 2017 season. So, you know, and and that created this one year gap where like I had a year until March of 2017 when I would start the AT. And so I was of course doing physical training, but I needed to do something to make money. And I'm this math kid who loves the numbers, who loves finance, who just came out of Techstars and saw that there was nine other founders that went through that like barf when they come to the numbers. And I was like, I could just be their number, Scott. You know, and I did for a number of the Techstars companies and then another of other companies as well. I started just like... that whole year. was like, I'll be a fractional to finance for all these companies. I'll make some money. I'll cut them off. I'll go hike the Adit. I'll figure it out from there. And in that year, you know, I'm using e-shares at the time. Now, Cardi, e-shares a lot for the capital management. I'm using, I'm pulling in HubSpot data, QuickBooks data, and I'm pulling it all in a spreadsheet and I'm managing all this stuff out of a spreadsheet. And I'm just like, man, if e-shares exists and HubSpot exists and QuickBooks exists, like why is there not one of those things for the model? This is so backwards that this is over here. It needn't that be the case, you know, like And I was calling it Crystal Ball. I was like, and that was just my vibey name for it. was like, Crystal Ball, you're looking at the future, you know, whatever. And like, and so was thinking about that. And then I went to like the trail and I spent six months in the woods, Georgia, Maine, 2000 miles, like the adventure of a lifetime. was a. ⁓ lots of bears, black bears, you know, and they're chill, like a moose, bears. My wife ran into a mountain lion and that's not chill, but it didn't eat her.
speaker-1: Any bears? ⁓ my god.
speaker-0: But that's so, and all the people you meet, man, and like that experience is amazing. And like, so that whole thing was incredible. And, and occasionally on the trail, like we're, it's this, it's this weird inverse of our style of life. For the life me you're living, we're sitting in chairs right now. A perfect example is, body's not doing nothing, just sitting there. Brain's cranking hard all day. All the work's going on up here. On the trail, it's the inverse. Brain's chilling. It's like, don't trip over a root. It's chill. Your body's cranking.
speaker-1: Yeah.
speaker-0: And so your brain has a space to wander. And so I'd just be like, that was such a cool part of that experience. And occasionally it would wander to crystal ball. I'd be like, man, you know that crystal ball thing. I think that's a pretty cool idea. Maybe I'll do that when I get back. Occasionally that would come up. And then when I did get back, I joined a CFO shop called Venture First. I met my co-founder Logan working there. He had had a similar concept. And I was like, man, check this out. And, you know, it's kind of one of those rest of history moments, you know, but but yeah, that was that was like the transition, you know.
speaker-1: That's amazing. I love that. And I love that idea that you essentially kind of walked away from all of it. ⁓ And in that way, mean, Forecaster wouldn't have been born had you not also had the face plant and then the sort of like impetus to go out and think about things. And I love hearing those. I had a similar thing in the stack list, but that... that thing that sticks in your brain and like if for you that crystal ball like kept bugging you, I love the psychology behind that, that there's this thing, this idea that won't let you go and it's like, me, can we just go back to that thing for a second and like, which is such an interesting genesis for something like that.
speaker-0: Totally. That's kind how you know it's honestly a good filter, you know. It's going to let it sit there for a while because one of things I tell people all the time now, it's like, do not start a company on a whim. Please don't. Because like, once you do and you get going on it, man, like it is a heavy load. It's not all sunshine and rainbows. It's a heavy load. And so you better be passionate about it. You better be serious because like you get that thing going. And like, especially once it gets going, like, I mean, if you're not careful, it's a prison.
speaker-1: better love it.
speaker-0: Like, let's just say it like it is, you know, if you're not careful, it's a prison. And so like, I think it's good actually, like let something marinate and if it's nagging and if it sticks around and if it has some real staying power, that's an indication that like, hey, this thing might have the foundations of something you could devote your life to, you know, if it, if it's fleeting, well, good, dodged a bullet there. Don't go running after it. You know what I mean? Right. It's like, Yeah.
speaker-1: Yeah, exactly. So you guys met and how did, what was the, what was the sort of then the beginnings of those discussions and, then the sort of, was it an evolution of crystal ball and a forecast?
speaker-0: Cool. it was like, so this thing was how you come back from the trail, right? I get a drink with John Schumann, he's the CEO of Intrafers. I'm just buddies with John. I'm talking about the trail. He's like, what are you going to do next? I'm like, you know, man, I'm not sure. Like I just got back. Like I finally get a job for little bit. And then, you know, like I'm kind of mulling on some things. And he was like, well, why don't you just come work for me while you figure it out? I'm like, yeah, dude, that'd also be great. Like I'll come in as a flex roll. I can build some models. I can do some business. Like, and so I did. And Logan was there as the head of FP &A for VentureFirst overseeing the analyst team, building all the models for the CFO services that VentureFirst ran. And so Logan, while I was out on the trail, had been having this idea for like, you know, what the card of financial models, the HubSpot of finance, like that kind of thing. And it was like, like, it was like three months into working at that job, were back to back in these desks. So we became real chummy, you know, we're similar age and we get along great. And he tapped me on the shoulder one day, he's like, man, you know, was just thinking. And he starts just going on about this idea. like, was just thinking, like, why couldn't we build this thing? Blah, blah, blah. And I just started like laughing at him. And he's like, what is that? Do you like what's so funny? And I was like, just check this out. And I had made a deck for crystal ball back in the day just to organize my thinking. And I just I pulled the deck up. I was like, flip through that. He starts flipping through it. He goes, he was like, what the hell? I was like, I don't know. I was thinking the same thing, dude. I can, you know. Yeah. And it was kind of one of these moments where it was like, man, if you're thinking this and I'm thinking this.
speaker-1: Incarnate city
speaker-0: There's something to it. Like, let's take it on a turn. And now this is Logan's first business. And so much like I was a fantasy, I'm like, he's been a venture first for years. He's like, this is a first idea. And he's a little bit more like, all right, let's quit. Let's start this thing. He's excited about it. And it's just like you would be. And me, think the scar tissue of my first failure said, well, hold on. We got jobs. We got salaries. Let's just play it cool. And let's take this thing to some checkpoints. let's minimize the risk so that if we do decide to launch in, we can do it kind of like with a pretty good good footing. And so we actually incubated the company at Venture First for 18 months. For six months, we just did a bunch of customer discovery, know, something I never did it fancy of, just ask people like, what do do for your model now? What do you like about it? What do you not like about it? Do you have insight? How do you share it with? Just like nothing about Forecasters, just only questions about the model. And after six months, you know, Venture First is a company that's selling Excel based financial models. So this is a competitive product at the end of the day. so, and we like, so we could have like, you know, so we had to go to Venture First about this. And I love John, John's a friend and everything like that. So we like, we wanted to do it on the up and up. So about six weeks into that stealth mode, we come to John and Scott Lurding and Rob Pinta and like the leadership of Venture First. say, so we've been, we've been cooking on this idea. Like, what do think about this idea? And like, we kind of want to move towards this and leave and do this idea. And to their credit, you know, they were not at all territorial like great, thanks for the new product line. They were like, we support you. Like we were some of their best two guys. They're like, we support you in spinning out and doing this because that's what great entrepreneurial ecosystems are all about is like they spin great companies out of other great companies. And they were like, you know, like, we'll take a single digit equity slice, you know, as like, as to basically like, let you guys over the course of 2019 over 12 months, phase shift up our time on Forecaster. you know, like basically Spartan many more and more more time while they covered our full salary the whole way through. And then at the end of 2019, I was full-time forecaster raising a pre-seed for forecaster while they were covering my salary, you know, and then we get the pre-seed done and January 1st of 2020, we switched over from one payroll to the other 750 K in the bank. We're ready to rock 18 months with the runway and we come straight out the gate. And it was like this perfect way to like low risk and never go out without a paycheck, never paid myself less than 70 K. you know, to just like shift over and hit it, you know, in a way that like fantasy hub was a nightmare. I paid myself $12,000 a year for two years. We never had more than six months of runway in three years, you know, and it was just as tall as this, but it's the learnings of a second time entrepreneur. They say, OK, I think we can like, let's be smarter about how we kind of set this thing up so you increase your probability of success.
speaker-1: So good. Like, I just had this picture of you basically jumping off the cliff, but you have the paraglider and you're just sort of like, yep, all good. And you're just sort of like, instead of the falling down and like bumping off the sides of, you know what I mean? Like, and all the things that you're just sort of like, all right. And like, that's how you started, which is amazing.
speaker-0: And that is so, I think about it in so similar ways that sometimes I felt with fantasy of it was just bouncing around like a Plinko board. You're just like, boop, boop, boop, boop, boop. And it's like Forecaster, not that it's been all just up into the right, but it's been so much cleaner. Like for example, we have only one time in the company's six-year history had less than three months worth of runway versus fantasy of never more than six months. It's like we've always been in a good financial position. because of the proactivity, because of the intentionality, the business model, the strategy, getting the people right, all the things that we've done this time around that I learned the hard way of Vanity Hub and then we could do on initial at Forecaster has just led to a better business. all I see many, many things lead into that, but that's just one of those things. so I think it's like, I'll put it to you this way. I think if I ran a venture fund, I would probably exclusively invest in second time or more founders. Like I don't think I would invest in a first time founder, no offense to any first time founders, some of them hit it and crush it. But it's just so hard to hit it and crush it on that first time around. I think I would filter out that and just say, reduce that risk profile and say, I'm only going to invest in people that are second or third time around because it's just so much easier to hit it when you have your variants.
speaker-1: Well, and you know you're also getting people who probably had a fantasy fall down version and then is like, okay, like this is how I approach the world differently now, which then you don't have to filter out, ⁓ which is, yeah, no, so true. What? So, okay, so you jumped off, you're gliding now, ⁓ you know, after transitioning out from the company, what was the first like, you know, first month, first six months?
speaker-0: Yeah, so it's interesting. first month was we went into Techstars. So actually it was really cool that like, so one of the intentionalities around this company was when we're bringing forecast to market, of my kind of, one of my core philosophies that you could say are core beliefs, is that distribution wins the game. That product's really important. People are frankly at the top. People make the magic happen. Distribution wins the game. Product's super important. But it's like I really prioritize distribution. Having gone through Techstars, I knew that financial modeling was a piece of the curriculum. I thought that if we could get Forecaster into Techstars, would be the, it's the biggest, the most influential entrepreneurial network in the world. It would be a really great asset for the company from a distribution perspective. And so in 2019, ⁓ I applied to Techstars anywhere. At the time it was the virtual accelerator, you know, because it's before COVID and everything. And I knew the managing director from my earlier time at Techstars and like, And we, and he took a chance on us. had no product, no revenue, no customers, just an idea. Me, Logan, and our Tentahoo co-founders and like, and, and, and they accepted us. And so like literally we started the company on January 1st and on like January 16th or whatever it was, Techstars started. And so we were like a brand new, don't have anything, no metrics to report on. Like weekly metrics are like not a thing. We were just building. And so we just went straight into Techstars and that, and so that first three months was this awesome, just like. you know, going through mentor madness and getting all these ideas on how to point the company, which is really fast tracked our iterative thinking on strategy, you know, and then like getting to that midpoint of the year when like we were supposed to have a product in market by the middle of 2020 so that we could sell at the back half of 2020 and then raise the first half of 2021 because that's our 18 months runway through Q2 2021. And because we didn't get the product out in June of 2020, we didn't end up launching it until December of 2020, but Logan and I made a very smart move, which is to say, OK, we don't have a product. were literally in June, we're like, shit, we don't have a product. And we're probably not going to for a while. Like Jonathan saying, it's just taking longer. And like, we get it. OK, this is a tough product. But it's like, what are we going to do? And we started to think really well, like, we've been selling Google Sheets financial models for years. Why don't we just pre-sell annual subscriptions and give build models in Google Sheets and say it's a pre-sold annual subscription when Forecaster Lawns will migrate it, blah, blah. And we were, and we started selling those like hotcakes. Like, so Logan and were just slinging Google Sheets models, or building Google Sheets models. We're all calling them pre-sold annual subscriptions or building like, you know, recurring revenue on it, even if we're just selling Google Sheets models. And, and, and in Q3, we sold a hundred, like 50 or 60. And then in Q4, we sold another bit. So we had a hundred customers by the end of the year, just all on Google Sheets. And then, and then, and then you'll love this. Cause like I said, the product's launching, we're going to have to go immediately into fundraise. And like, it's like, I got to start this raise in January, 2021, because we got six months of runway. It takes a while to fundraise. I got to do it. And I don't want to do that with a bunch of Google Sheets models. I have to get them into the product. I have to be able to say, I've got a hundred K of revenue in the product, not in Google Sheets. you know, and so we launched the product like the third week of December. We had two analysts that we had hired on at this point, Alex and Kelvin, who are still at the company, directors now, those are total killers. They've been here for five years. Amazing hires. It was like me, Logan, Alex and Kelvin. 100 Google Sheets models. And the week, I kid you not, the week between Christmas and New Year's, we called it hell week. And the four of us hunkered down in a room and hand transferred a hundred individual financial models into the software that week in between Christmas and New Year's. And it's still just like a running joke at the company that hell week. But we just hard shifted them all up into the product, launched them all. And then I go right into the seed round in 2021. And we just smashed it out of the park. You know, it was like...
speaker-1: My gosh, cut to the hacker apartment photo of two people laying on a mattress, like just wiped out, like trying to catch 10 minutes of Z's.
speaker-0: Oh, was outrageous. And those guys, they started in November. Like we hired them in November and like a month later, we're like, OK, guys, I'm sorry. But like we got to all like, I know it's Christmas, but it wasn't that we didn't like work on Christmas, but it was like that like five or six days in between. It was such a fun memory. Honestly, look, it was it was literally hell at the time. We were all like stressed out. But but looking back now, it's one of those things that's just like funny. But
speaker-1: Yeah, that was crazy. So you went into the next year sort of prepped then.
speaker-0: Yeah. So we like, it's like, boom, we had just shipped it up 100K into the software. Not a lot of user engagement metrics or anything like that, because it was like brand new in the software. But I went in straight in to a seed round there. And honestly, we hit it great. I mean, I would say one of my biggest strengths is kind of the masterminding of the fundraising process. I'm very intentional about building the pipeline. I'm very intentional about crafting the narrative. I'm very intentional about approach, blitzing the market. scheduling well in advance to concentrate investor meetings in a very short time period to kind of like cheat my way towards momentum, Because like broken clocks, right? Twice a day type of deal. got 40 pitches in a week. You're going to get a yes. And that's what happened. Like I had 40 pitches a week for the first four weeks of January. the end of the first week, I had 750K committed. By the end of the second week, I had 1.25. Third week, I get a lead check of a million from Resolute Ventures. And by week six, We were well over subscribed on the round. You know, and it was like, it was the cleanest hit of funders. And of course it was a great time too, right? That first quarter of 2021, it was just like nice and frothy in the market. You know what I mean? So just like brand new software, AI hadn't hit yet, nice and frothy off COVID, just hit a quick seed round and get it done. And that one really like propelled the company really to that first good go. Like that freezie cap was just like, let's stand up with enough proof to where we can get a nice batch of capital. That two and a half million could then give us an 18 to 24 months to really take a rip at it, you know, in the market. And then that was, and that kind of kicked off that, that, that next phase.
speaker-1: Yeah. ⁓ wow. That's so good. ⁓ I'm getting all these mental pictures of that raise process and being so concentrated and that I'm imagining after you get oversubscribed, same thing, right? It's the, ⁓ slept great the next day after. ⁓
speaker-0: ⁓ And that was my first term sheet, know, it's like a fantasy hub It was all Angel Capital like I said like that that round was a special one for me It was like the first time I ever got a VC term sheet in the email Like I remember like me and my me and my wife it was kovats So things were closed, but we ordered in Jeff Reaves was like a really nice steak house man I was like ordered to the house, you know, I mean and it's still I still remember like the takeout containers because they were like so nice But we ate Jeff Reaves that night and we were like, you know, it was just our cloud nine Such a great feeling, you know, when you get that done and kind of unlock that next stage and then such great energy, you know, to go to go make it happen from there. And, and we were able to with that two and a half million really just start to build on the momentum, the minimum we had, like really lean into those like tech stars and other partners to drive business. You know, the product was, was, was solid. Although later we would have to rebuild it. was like one of those ones of like a, you know, build it once, build it again, then build it right. You know, and, that's where we're, we're finally now. with PorCaster, but it was an awesome product to kind of take to market. And we were able to, with that 2.5 million, get up to a million in annual recurring revenue, which kind of put us to the next phase, which was, I'll say, my first attempt at raising a Series A in 2023. I just raised my Series A six weeks ago, 7 million in 2026, but my first attempt was actually in 2023. when we had a little bit north of a million in annual recurring revenue. And frankly, I honestly, some snappier growth metrics, but I went in to go raise that next phase. The quarter that Silicon Valley Bank was like, ⁓ you know, and failed. And it was the absolute like worst time to try to be fundraising, especially for a startup selling to startups in the financial data ecosystem. It's like, hey, financial data startup selling to other startups.
speaker-1: Yeah.
speaker-0: And the like center of the financial data startup ecosystem just imploded. You know? Yeah. And it was, it was such a nightmare. was like halfway through that process trying to raise an eight million dollar series. I had some folks like pretty deep in the process and then Silicon Valley Bank failed. And I had to cut, it was like one of those like ⁓ call the war room together moments where after that, like, you know, everybody was dropping like flies out of the round and Logan and I had to kind of pull the council together to just say, Hey, like What are we going to do here? Because we only have another four months of runway and the Series A seems at significant risk. I still have another half of my pipeline that I haven't pitched. Am I going to keep pitching this $8 million Series A or should I downshift? And that was one of those really tricky judgment calls that I think as a founder, the thing that more than anything will define your success or your failure is your ability to make really good judgment calls. And it's like, there's a lot of gray scale decisions that come to your desk. There's no clear answer. And you just gotta look at it. You gotta ask for some opinions. You gotta stir them in a pot and you gotta pick a line and you gotta run like hell. And you do that right in a bunch of succeeding things. You're gonna win. You do it wrong. You're gonna lose. And that was one of those big moments.
speaker-1: Yeah, well, think being able to, and I imagine that this is where being outdoors and sort of nature also probably plays into ⁓ your operating system, but being able to also get quiet and listen internally, go back to that sort of empty brain, because that's ultimately where, and you don't know where it comes from, but you just have this moment when you get quiet and listen and you go, yep, that's it. And you're not sort of. You're not closing your eyes and so on to do an eeny meeny. You're going like, this just came to me and it's from the culmination of everything that I've got internally.
speaker-0: That's right. I think that gut intuition is it bubbles up in that way. And I think you have to listen to those instincts and you have to be able to discern between an impulse and an instinct. that's not always clear. But and that's where the judgment comes in. that my our judgment at that time was voted no confidence on the A downshift to a four million dollar seed to the second half of the pipeline that I set up means with they were none the wiser about the A. And I went to them and said, hey, just launched a four million dollar seed to You're gonna love it, know. That's awesome. we were able to get that thing done. Over-subscribed to four and a half. We closed that round in July 2023. And that got us on that next turn of the hamster wheel, which was then a really critical time for the company where it was at that time, as we went to 2024, where we started to realize, hey, this go-to-market platform that we've built is not going to scale. There's some stuff we got wrong, product... product design wise early that are going to be tough to rip apart and we actually brought in a CTO, kind of take us from one to 10. He's like a guy, Eric Schreiner, he's our CTO of the company now. We ended up by part in ways with our co-founding CTO, Jonathan, as he went to go start another company in the crypto space. And we brought in Eric and one of Eric's big moves like guys, think like we got to kill 1.0. We got to build Forecaster 2.0, And that was a big move. There was a hard move that was like, Hey, I'm telling you right now, Steven, it's going to take 12 months to get this thing to market. You're not going to know if this bet is right for like 12 to 18 months. And, but you're going to have to bet the company on it because like, you know, and, because, and, and it was needed, like our metrics and everything led us, like it was a, it was a, it wasn't an easy decision because of that time horizon, but, but I knew it was right. And when we made that decision, it meant, okay, things aren't going to really start to get
speaker-1: of
speaker-0: really good for us until we get that new software out. Things are still going to be good. We've always been very consistent and very linear in our growth, but we've always needed to go exponential. I knew at that time, I'm going to have to find a way to capitalize this company through that rebuild. That was the next big checkpoint that I had to get through as a founder was like, how am going to capitalize this thing one more time?
speaker-1: than
speaker-0: so that I can get 2.0 out into the market so I can get some good early proof points of that and then go raise our Series A like we just recently did. And that's where our Seed 3 came in. You know, as we raised it, a Seed 3 that was largely internal and it allowed us to kind of shoot that gap. And I had a bit of a master mining that I did to get that Seed 3 done as well. So that was kind of the next big phase for the company.
speaker-1: Oh my gosh. Well, now you got all the rounds under your belt. You've seen all the different- I'm making them up. See you three. That's amazing. So once you raised that and you sort of between the six weeks ago and the A, between that moment and the A, how was that period?
speaker-0: Yeah, well, that was when we raised the C3 was in August of 2024. And we launched the new software in March of 2025. so that was really the big moment here at Forecast, was when we put that new software up. It's just 10 times better than the first. The product design and philosophy around it is way better. It's like really Excel-like at the core to flatten the learning curve and like max the intuitive usage of the product. But then integrations, analytics, reporting and collaboration are much better structured around it to 10x the value. And I think that's what we've always had to do to win this market is like, make that mountain of a learning curve a molehill versus Excel and then give them a really green pasture on the other side to make it worth it. You know, and I think 2.0 really did that for us. And since we launched it in March, like the net revenue retention is way better. The internet economics are way better. like all those kinds of core metrics, the engagement is way better. It's just a much, much, much better software and it's unlocked a lot more product velocity. And so was kind of this like raise the seed three, late 24, just hold your breath until you get it out in March and March to the end of last year was just hit it, hit it as hard, as fast as you can. to just drive that growth up to where then in September of last year, you I went out to raise the Series A and Logan, my co-founder, when I go raise, he takes care of the entire business. completely, you know, put up a giant wall between me and the business more or less. If something's absolutely critical and I absolutely need to know or he needs my opinion on something, he pierces that wall. But otherwise, I stay in my little bubble where our shit don't stink, frankly. You know, and it's just like, and I can just live in that world where I'm just pitching investors on the vision and the story and the whatever.
speaker-1: You're freeing up brain space too. If you get in any of the muck and mire of any of that stuff, pulls you out of that.
speaker-0: 100 % right. That's 100 % right. And so I decided to do a road show this time around. We've always rated virtual, but I said series A, it's serious. Let's do an eight week road show. You know, I went to Atlanta, Boulder, New York, Boston, Salt Lake, San Francisco, Austin, know, seven or eight cities in eight weeks, you know, from September through October. That was all my like initial pitches. And from those initial pitches, we ended up getting a term sheet from a fund out of Capital One in November. You know, so that they ended up leading the round. And that's already the syndication process, you know, which kind of bumped us up against the holidays. There was a race to try to get it done by the end of the year. We didn't get it fully syndicated by the end of the year, but we did by mid January. ⁓ And which, which kicked off like a two week close timeline out of Capital One has more kind of hoops they got to jump through. So. Close was then supposed to be in end of January. And mind you, like I knew since April of the prior year that we were going to run out of money in February. that's where we are. We are the best at forecasting. like we're like, yep, we're like, February is when we're going to be out. So let's go out to market in September. We'll get it done by the end of the year. A couple of months of buffer. No big deal. Of course, like I just said, we didn't. January, so it's everyone on our closed date supposed to be January 29th. We're just like. two weeks before we run out of money and it was really uncomfortable and tight. But like we're using our software, we're managing the cash as good as anybody. We're keeping it steady, you know, and I'm feeling good about hitting that round in late Jan. And then of course, like, you know, this round was a tricky one. We're like literally a day before close, one of the investors that's in for a million calls me and says, basically like, surprise, like I can only do 500. Like you got to find another 500, sorry. You know, and it's just like, and so now I go from hitting my minimum to 500k below. I got to spend the next two weeks, you know, replacing that 500k out of thin air. Me, Logan, and my dad ended up throwing a little bit of capital in to kick it over, right? And I closed literally the day before the last payroll exits my bank account. And it was like as tight as tight can be. so I go.
speaker-1: slide right in. ⁓
speaker-0: and then it just hits and I'm just like, you know, I just absolutely just
speaker-1: You hit the refresh button on the bank and then you go like...
speaker-0: 100%. So, you know, it is not for the faint of heart this way of life, but it's like, but it's that thrill, you know, that is the thrill. It's like, it's just you're riding it, you're hitting it, you got to trust yourself. It's like an idea that go, I'm not exactly, I'm stressed and stressed, but I was also confident. I'm like, I'm going to get this done. Like hit, just hit it, just focus, just, you know, control what you can control, do what you got to do and just hit the shot, you know, and it's like, of course, when you're in the middle of that process, it's really scary, but then you hit that shot. and you feel like a titan. You know, you're like, it's that feeling of like, I just accomplished the hardest thing I've ever accomplished. And so I'm kind of still in that afterglow right now of just being completely and totally stoked on what just happened.
speaker-1: You know, yep. That's amazing. Awesome. Well, what do you see from this point forward? Like, what do you see? I think we're in an era now where like doing the old, where do you see it in five years is not really that seems like forever away. But like the next few quarters, like what are the things that you've got your eye on?
speaker-0: Yes, so the two big ones right now is what we call the integration supercharger and building the Ironman suit. the biggest flag that we're planting or where we're standing our ground is frankly on humanity. Most of the market in our space and financial forecast is flocking to AI first, AI generated, AI everything. And we recognize the utility of AI, but we think AI is an Iron Man suit built around a human. think AI in its best expression is a really powerful Iron Man suit built around Tony Stark that can help him do all these amazing things that he couldn't do without it. But if you take Tony out the middle, it's just a hunk of metal. so our philosophy is like build the Iron Man suit. And that's why Forecaster, yes, we have a SaaS platform that's super dope, but we also have analysts and CFOs on staff that provide expert financial support, strategic financial leadership for your company. We think finance should be run by an expert. And so like the big focus for us right now, now that we have the new software up and stable and out and rocking and all the Claude Cohn stuff that supercharge our engineers in the ways that nobody thought was possible five years ago, it's incredible the pace that they can build. It's about just integrating it with all your data so that Forecaster is not just your financial model. It is your goal setting and performance tracking engine. It's where you set your goals. It's where you track all the performance of your business. It's where you understand the metrics of your business. And so like connecting your CRM and your payroll and all that kind and your Stripe. So working on those integrations and then building that Iron Man suit to turn our analysts into superheroes, basically. just like allow them to just like, deliver more impact for more customers than they ever could before. And so I think that's like the big, big two focal points of the company right now is like, is drive those two strategic priorities into existence. You know, once that's there, then I tell everybody it's, it's, it's less thinking, more doing it's execute with excellence. The game is one on the field of play, but you must execute with excellence. No one forced errors, no mistakes occasionally, but learn from them. But it's like, you got to execute, you know, and it's, and it's, so it's not this kind of sit back and think, you know, that it's a, it's a very doing focused time. And so that kind of back half of the year, that's what I'm trying to do is like anything big that's changing. That's like, that's new. I'm trying to get it done this quarter so that like back half of the year, it's just put your head down and crank and let's go hit six, seven million in ARR. We do that. We are, we are off to the races. know what I mean? We're off the races. So that's the, that's the focus.
speaker-1: That's amazing. I love it. so for the wrap up piece, what's if you had to look back in your entrepreneurial journey up to this point and give yourself a piece of advice, ⁓ you know, the younger version of you pre fantasy maybe, ⁓ what's one thing that you sort of still end up leaning on or focusing on? what's one of the things that you would pass on?
speaker-0: biggest thing it's not even close for me is like is what I call people make the magic happen. That's my phrasing for it. That's what I tell myself and that what that means is just that like it's all about the people. just like put the people first meaning like like you know just like it's that old ad is like it's not what you know it's who you know it's like it's so true we're like like you got to get out there and like be meeting people be evangelizing be thinking about people. Like if you're doing a partnership, that's a people game. You better build that relationship before you get into the transactional element to it. When you're dealing with a customer relationship, roll out the red carpet, win them over at the people person level before you drive the business outcome. When it's an investor, you better get to know that person super well because it's like a marriage, It's just like recognizing like at every turn, it's the people, it's the personal relationship. It's that kind of human relationship piece that affords you the most leverage. Early in my career, I was like, I'm too busy to go to that event. I'm too busy to get coffee with that guy. There's no transactional benefit out of it. You know, it's like, I'm getting coffee with all sorts of people. I'm meeting people. I'm doing whatever because like, it just comes back in serendipitous ways. That guy three years later sends me an email and connects me with someone who's just like, great. It's like, you never know. And so it's just like, it's just play that people game well. You do that and many, many other problems take care of themselves. You don't do that.
speaker-1: That's all wrong.
speaker-0: And you can have the best other stuff in the world. I think it's just hard. I think like, think that just that really quitting the people first. That's the, that's the big one I would have told myself early on.
speaker-1: I Nice. I love it. Well, thank you so much for the time and for the stories. love hearing like, you know, I just love mentally taking this journey through all the different ups and downs and the whole, the whole journey. It's almost like we just sort of did the AT version of Forecaster, right? It's just all those little like, you know, outlines and all.
speaker-0: Yeah, the peaks and valleys. Totally. Dude, totally. This is so fun, man. I really appreciate you having me, Kyle. It's awesome, man. so it's great to be here with you. I appreciate you.
speaker-1: Yeah, amazing.