The Vertical SaaS Bug + A Career Switch (w/ Nick Tippmann of TipTop Ventures)

Speaker A: You prefer ketchup or ranch?

Speaker B: Oh, it's not even close. Ketchup all day.

Speaker A: What do you have against ranch?

Speaker B: Nothing against ranch. I'm a ketchup lover.

Speaker A: Introducing Nick Titman, a seasoned marketing guru whose strategic brilliance has earned him acclaim across the technology and um, medical device industries. As the former CMO and first employee of Greenlight Guru, Nick orchestrated a remarkable journey from startup to tens of millions in ARR and over $120 million in investment. Prior to this, he founded, led and sold a media company. Before that, he left college early to learn how to run a venture backed startup by actually doing it. Not to mention his lucrative tip top enterprises electronics business that he started in high school. He didn't even know he could sell that, but he certainly could have. Nick is a founder, operator turned investor advisor and a driving force behind innovation and growth in tech. We are thrilled to have Nick on the podcast today. This is the Startup Executive podcast. The Startup Executive is a podcast designed to help you become a well rounded startup executive. The best executives have a good understanding of all aspects of the business. Join us each week to learn from a new go to market leader on, um, what is important in their department and what it takes to become an effective startup executive.

Speaker C: Thanks for coming on, Nick. Welcome to the Startup Executive.

Speaker B: Thanks. Thanks for having me. Grayson. Excited to be here with you and Crystal.

Speaker A: We're really excited. We have a lot to talk about, but first we want to hit a few low key questions. Are you ready?

Speaker B: Yeah. Let's do it.

Speaker A: All right. Do you prefer ketchup or ranch?

Speaker B: Oh, it's not even close. Ketchup all day.

Speaker A: What do you have against ranch?

Speaker B: Nothing against ranch. I'm just, uh, I'm a ketchup lover.

Speaker A: Just, just a lover of ketchup.

Speaker C: Guacamole or salsa?

Speaker B: Salsa. Salsa for sure. And a little bit spicy.

Speaker A: It's the best. Night owl or morning person?

Speaker B: Definitely, definitely a night owl. Uh, that's for sure. I can build my morning, uh, bird muscle, but naturally, uh, night owl.

Speaker A: Ever like all nighters?

Speaker B: Yes, most recently I've pulled an all nighter in the last six months trying to get this new project I'm working off the board. So few and far between. Uh, but I have for sure on those all nighters.

Speaker C: Do you prefer coffee or tea?

Speaker B: Definitely coffee. Yeah. 100%.

Speaker A: All right. Do you prefer movies or concerts?

Speaker B: Oh, that's not even close either. Love concerts. Not a fan of movies.

Speaker A: Okay. Is it the boredom of sitting or what is it?

Speaker B: It's hard to keep attention. These Days for two hours. And the quality of movies just isn't that great. And so a great movie. Don't get me wrong, I love a great movie with a great storyline. I just think they're few and far between.

Speaker A: I'm right there with you.

Speaker C: That's fair. But to be. I'm trying to think. I feel like I've fallen asleep at more concerts than I have movies, but maybe I've, uh.

Speaker A: We gotta take the right concerts, Grayson.

Speaker C: Real books or digital books?

Speaker B: Digital, for sure. And specifically audiobooks.

Speaker A: Okay.

Speaker B: An audible. Audible learner, for sure. Rather than, um, reading. I. I've. Yeah, definitely audible.

Speaker A: Okay, you're segueing yourself into the very last one. Do you prefer audiobooks or podcasts?

Speaker B: Ah. Uh, that's. That's a good one. I listen to way more audiobooks than podcasts, but I never was one to watch YouTube until maybe, like, two or three years ago, and now I got a steady roster of podcasts that I watch on YouTube rather than watching on TV. But in general, if I'm, like, truly listening, it's definitely an audiobooks all day.

Speaker A: Okay. I love all the information you can consume on an audiobook. That's good.

Speaker C: Are you a My first million podcast listener? Is that one of the ones you watch on YouTube or. No.

Speaker B: Sporadically, here and there. Yeah.

Speaker A: If you can't tell, Grace is a big fan.

Speaker C: That's a good one.

Speaker B: Very, very nice. Yeah. Uh, Sam's down here in Austin.

Speaker A: Practically brothers. No, I'm just kidding. All right, let's get into the good stuff. Nick, let's just start. How would you describe yourself to someone who has never heard of you?

Speaker B: Yeah, so I like to describe myself as an entrepreneur at heart. I think I'm someone that likes to solve challenging problems with interesting people and consider myself, uh, a lifelong learner.

Speaker A: I love that. Challenging problems with interesting people. That's great.

Speaker C: And that sort of, you know, maybe leads into, uh, a new adventure that you're on. And if we look at your LinkedIn, we see founder and stealth mode. And so I know stealth mode is not generally when you talk about what you're doing, but what sort of can you give us? What are you up to these days?

Speaker B: Yeah, um, well, Grayson, you got the matching title I saw on stealth mode, so I might have to flip the question right back at you. But without giving it all away here. Been working on a new, exciting venture for the last six months or so and really has been a, uh, passion of mine and something that I've wanted to do for nearly the last 15 years now at this point and so really excited that it's all coming to fruition. And it is uh, a venture outside of what I've done over the last 10 or 15 years as well. But it's an exciting development. It's uh, a natural progression in my career I believe. And we'll have lots more to share soon publicly over the next month or two. But yeah, more, more to come. And as it says on, on the LinkedIn profile, if you know. You know though, we're excited, we're excited

Speaker A: for it to roll out.

Speaker B: Yeah, thank you.

Speaker C: So since we'll, we can't get into that just yet, how about we take it back to the beginning of your career and so just want to give a little context for the audience. You started a couple businesses, you joined on a couple startups who you know, went on to become successful. Um, so I'm just interested and this is kind of an open ended question, but if you had to look back and so of break that out into, you know, the three most pivotal experiences that really you feel like made you who you are today, what would those experiences be?

Speaker B: That's tough. Getting, getting right to the heart of it right, right off the jump. I, uh, love it. I think the, probably the biggest impact on me professionally was just growing up in an entrepreneurial family. So my grandpa was one of 16 children and uh, grew up in a, in a three room. My great grandpa famously said, when you have 16 kids, you're an entrepreneur by force, not by choice. And so I think the entrepreneurial blood run runs deep. And my grandpa was an entrepreneur uh, in the Midwest and many of his brothers and sisters went on to be entrepreneurs. My dad's a, uh, manufacturing entrepreneur in the Midwest. And so I think just growing up around a family that um, kind of had this belief that anything is possible and had seen ideas start from nothing and turn into really big companies as well. And just having a, uh, nurturing and loving and supporting family around me that supported and encouraged my entrepreneurial endeavors was really impactful. And it's not my success, but to be able to see success firsthand or tangentially in the extended family with people like Tippmann, paintball guns, who essentially popularized the sport of paintball. Uh, oh, wow. Yeah, uh, into what it is. And I think that's probably most famous attached to my name, but that was my great uncle. Kind of different side of the family. Not something that I dealt with every day. But of course you hear stories. We all grew up in Fort Wayne and that Families are all still in Fort Wayne. And so I think that was the most pivotal one of just believing that anything is possible and having a great support, supporting family, uh, around me that encouraged that you asked the 3, 3 most pivotal experience that made who we are today. So I think the next one would be finding what a tech startup is and what the word tech startup. My, my senior year of college at Indiana University and uh, excited to maybe go a little bit deeper into that one, uh, a little bit later here into into the pod. And then I think the, the third most pivotal experience would, would really be around building greenlight guru over the last decade and all the ups, downs, blood, sweat, tears, uh, quite literally and some points, uh, and what it goes into building uh, a pivotal company from nothing into a uh, company with tens of millions in ARR and hundreds of employees and all the responsibility and uh, everything that comes along with that. And so I kind of say those are three pretty key moments for me.

Speaker C: I love it. Well, so one question just about in, you know, your initial key defining moment essentially of just like being around the family business, was that something that, you know, you were a part of early on where you could sort of see, you know, what is it like to be, you know, a business owner, operator type of person or how did that sort of translate into just your life as a kid?

Speaker B: Yeah, that's a good question. I don't know that I've ever really talked about this definitely on podcasts or publicly, but my grandpa had started businesses before I was old enough to remember. But the one that kind of took off when I was probably three, four or five years old, just starting to have some of my first memories was uh, a commercial kitchen oven business that created steamer ovens for commercial kitchens, hospitals, schools, the military, basically anywhere that has to cook a lot of food in a short amount of time. And I watched my dad transition from being uh, in his early 20s, trying to figure out his career and what he was going to do and working different jobs to becoming the top sales rep at my grandpa's new company that started to take off and what that did for our lives of going kind of from different jobs here and there to now having a steady, reliable job and growth and a career if you will, and watching him grow to the top salesperson and then ultimately spinning out and becoming a channel partner of that company, but building his own business next to it that resold those companies and then ultimately, um, once my, my grandpa sold that business, my dad actually went into business and built a very similar company. In Fort Wayne that competed with my grandpa's former company. And that was kind of call it from the time I was 3 or 4 years old to the time that I was like 18 or moving away to college was like watching that journey and seeing the different iterations. And so I got to watch it. I wasn't super involved. I worked in the. In my dad's factory every. Every summer, uh, got to be there every morning 6am we used to ride my moped there myself, uh, starting the summer, summer going into freshman year of college, and worked up and saved up my own money to buy my moped so I could get to, um, work, uh, there. But, yeah, that was. That was pivotal and kind of in my just personal and professional life of being around that. But starting. Starting at the bottom, if you will, in. In the factory, uh, working. Working my way through the business like everyone else, but not kind of over there on the business side of the house at the office with, uh, maybe some of the other workers.

Speaker A: Grayson, I just have a question. I don't know if you know, Nick, but Grayson has a. Has a motorcycle. So did you start with a moped, Grayson, or did you just go right for the bike?

Speaker C: Uh, uh, for me, I mean, I had a bicycle. I went bicycle to motorcycle. So that was my path. Uh, mopeds, I think, are a nice in between. I think in cities, motorcycles are a little bit much, and I've spent too much time, uh, in cities over the last couple of years. So I think a moped may be the next purchase. Uh, on my.

Speaker A: My side, that tells me Nick was ahead of the game. Okay. But back to your journey. So this is really interesting. You saw your father and grandfather grow their businesses from young age to 18, and then it's time to go to school. Or you chose to go to school, Right? How did you pick your major? It seems like it must have been heavily influenced by your entrepreneurial background in the family. And then I'll be interested to get to your senior year when you started to make some very pointed changes.

Speaker B: Yeah, for sure. I really didn't put as much thought into it as one, uh, might hope, but I knew I wanted to be an entrepreneur. I knew I wanted to go to college. I only applied to one college ever, Indiana University. That's where I was going. Hoosiers. I wanted to study business. I wanted to go to the Kelley School of Business. They had a great entrepreneurship program. And so it was pretty easy decision. But I always said that I went to college to, quote, unquote, learn how to start a real business. And as we get into more of the story, what I didn't realize is that I very much knew how to start a real business when I was running a profitable business in high school, but didn't really appreciate what that was at the time and shut it down to go to college, to go learn how to do what I was already doing. And it took me a couple years to then realize that as well.

Speaker A: You just mentioned your high school business. Was there something from that experience that you maybe not still use today? You're quite a bit removed from that but kind of used in that either decision making to leap into tech startups or um, when you were at Greenlight Guru for instance.

Speaker B: Yeah, I think the experience running Tip Top Electronics was

Speaker A: a little background on what that is. Give a little background on Tip Top Electronics.

Speaker B: TikTok Electronics was a ah, business that I started in high school and it was an ebay reseller business. I had found a little arbitrage between liquidation.com and eBay.com where I was buying Guitar Heroes by the pallet load and driving my mom's Suburban down to Plainfield, indiana to the liquidation.com factory or uh, storage unit or unit that they had there and loading up the Guitar Heroes in the back of my mom's car and driving them back to Fort Wayne. And I didn't realize but I basically had my own inventory fulfillment and shipment center that I turned our spare garage into. I guess I just didn't have any appreciation for really what I was doing at that time I don't think.

Speaker A: Yeah, and I don't want to discredit any smaller business or like for instance like landscaping or lawn mowing. Great business. So many successful entrepreneurs started there. But the whole electronics thing is one really, it seems a little niche. And number two, I think you were the hero of so many children in the mid 20 teens.

Speaker B: Yeah, the Guitar Heroes were a lot of fun. We sold a lot of them at a great value on ebay and uh, it was a great learning experience. But I always said that I quote unquote left or shut that business down to go to college to learn how to start a real business. What I realized and it took me until my senior year, the question that I was really asking was I wanted to go to college to learn how to start a venture backed business or what I always used to say at the time was I know how to buy stuff cheap and sell it for more. I don't know how to create the next Coca Cola or the next P and G and I only look to Fortune 500 companies. You look at the Fortune 500 companies in the late 2000s, early 2010s at this time and they're all like 50100 year old companies. And so my mind just couldn't get wrapped around of like how do you start one of these companies that are now 100 years old? Like where did they get their start? How can you build something that starts small into something big? And that's when I learned that's what a venture backed startup is. But that took me some years to get to as well.

Speaker C: And so you said you mentioned some big companies like Coca Cola. Those lots. Uh, were uh, there other companies that were maybe a little bit more closer to venture backed? Like Google? Were there other companies that you saw? And like I can resell stuff on ebay, but how do I make the next ebay? Like were there companies like that that you sort of looked up to and admired?

Speaker B: I wish I could say yes, but no, not at all. Not even a, ah, single little bit. Like I didn't know that like tech company. My first foray of like what a tech company was was I think we had one of our senior marketing classes ah, at IU my senior year and they talked about startups and they talked about like Reddit and stumbleupon and MySpace and it was like early Facebook. And uh, that was like the first realization that I had that those were like tech startups. And I, I think that was like right when Uber was getting started. We didn't have Uber in Bloomington at that time but I remember like Uber was one of the first companies that I ever saw that was like, oh wow, I understand what this concept is and like what they're trying to do and wow, yeah, that'll be big. But I didn't, that, that was like probably one of the first companies that I like, oh, I can see how a founder had an idea and like went and put this into the world. But I think like when the Googles were getting started or like I can remember when Google went public when I was in high school and like it was a, it was a talk. But I never like, it never clicked in my brain that like, oh, you could go create the next Google or something. It was like that's what other people did. Like it was just as foreign as how to build the next Coca Cola to build the next Google format at the time. So I didn't put those like in a different bucket. I almost saw them as the same of like this unattainable Thing that I, I didn't know how to do yet and I needed to go figure out how to do that.

Speaker C: I'm curious, like were you, I know just from research that you were going into college, you know, planning on doing an mba, but I'm curious like during your time, even before senior year where it feels like everything sort of clicked, just from what I understand so far, were you thinking of like oh, this could be an interesting like business idea or o, oh, like iu, why don't they have like XYZ here? Like were these types of things like coming across your mind or would you say that you were just sort of like experiencing college as like a uh, normal type of student? Like what was the first couple years like from like a business ideation perspective, if anything?

Speaker B: Essentially yeah, I would say I had a great time my first three years of college and I uh, used a lot of fun and I did very well in school but I was focused on getting my work done, getting good grades and having a social life. I always knew that I wanted to start a business, but I thought that I was on this path that as going to school and getting good grades I was going to have these classes and this experience that they were going to teach me how to start a business. It just so happened I got to my senior year and realized I had had zero of those experiences yet. And it became like you go into your senior year, first semester, you graduate, at the end of the year you go, they have all these career fairs and you got to start getting a job and like trying to get things lined up. And I realized I started interviewing for like Fortune 500 jobs of odd jobs. And I really, I was like holy crap, this is absolutely not what I want to do at all. Like I, this is not why I came to college. And well shit, I only have like uh, another nine months to figure this out. So Nick, you better get on it and figure out a business idea. And so I did go like switch modes pretty quickly of like, all right, now it's time to go figure this out and did start ideating and start looking and that's how I eventually ended up finding startups. And happy to kind of tell that story. But one thing I will just correct real quick. I know you mentioned that the startup, uh, MBA and it says startup MBA on my LinkedIn, but that was a self put together MBA. I never, I didn't even like barely even knew what an MBA was. I never had a vision to go get an mba. It wasn't until I found this concept of tech startups that then I looked into and I was like, oh, what do people that start tech startups? What do they go do? It's like, oh, there's NBA. But this was, that was 2011 that we're talking about. And it was like the early days for accelerator programs like Y Combinator and like tech stars. And there was like this movement around, like this idea of the real world or MBA or like Seth Godin's alternative mba. And I started to find all these classes and resources online and I was like, oh, that's what I want. Like, I don't care about the actual piece of paper that says you have an mba, but that, that's where the knowledge that how you start these companies that I'm looking for exist. And so how can I go get that information whether somebody else tells me I have the certificate that says I passed or know. Know what was in those classes or not?

Speaker A: Okay, Nick, we've reached what I think is like one of the climaxes of your, of your life or of your, uh, education and career. So you get to senior year and you're realizing all of these things you just said and you say you made a switch and you know you want startups and you know that corporate life is not for you. And so what you did over the next year is really cool. And if I can break it to everyone, it's not finished school. Sorry if I took that light from you, but I think that's really cool. Can you tell us a little bit about this very dynamic next year and maybe specifically tell us about the program. But I'm curious if you created it yourself or if you walked along a path that someone kind of laid out for you.

Speaker B: Yeah, yeah. This is the exciting part. So I got to my senior year, I started taking these crappy interviews that I realized I was not going to enjoy if I took any of the jobs. And I had this crisis moment of like, oh shit, what am I going to do? And Gracie, you started asking about, like, did I do anything in those first three years? Well, I started to realize there's like business plan competitions and there's all these business clubs and there's all these great resources that IU that I didn't take advantage of at all. So shame on me. We were having fun and realized there's a lot more that I could get involved with. And there was one in particular business plan competition called the Best competition, which led me down the rabbit hole of grace. I know you're an OR fellow. I saw as well uh, it led me to find the OR Fellowship, which is an entrepreneurial fellowship in Indiana. For those of you listening that may not be familiar at the time, though, you had to have a, ah, 3.5 or 3.7 GPA to get into it. And unfortunately, I was at a 3, 3, 5 at that time, and so I just missed the cutoff. But that is where I then found tech startups. And so there were all these tech companies that partnered with the OR Fellowship, exactarget being the big one in Indianapolis at the time, around 2011, 2012. And that was when I started to look into, like, what this idea of what exact Target was, what Salesforce is, uh, what smaller companies around Indianapolis at that time were. And that was like the light bulb moment. And so it was like the best competition led me to the OR Fellowship, which led me to an event in Bloomington, a conference called the Combine, hosted by Mike Troutsky and Brad Whistler. And it was that event that I'll forever be grateful for, and that truly changed my life was that I went to the Combine Conference that year in 2011, and I got to hear the story of Adeo. Uh, Alano, who is the founder of Form Spring and formstack. Formstack M, for those of you who don't know, sold for $500 million a, uh, couple years ago to private equity. And at the time, he had also started another company called formspring, which was an early Q and A answer site. And I heard him up on stage tell this story about how him and some friends had this idea for a Q and A answer site in Indianapolis, and they built it and it went viral and there was millions and millions of users. And all of a sudden they went and talked to these people called venture capitalists and angel investors. And it was like the first time I'd ever heard of those concepts or those words. And he, he talked about how they went and raised $40 million and they moved out to the Silicon Valley. The Valley. I learned what this thing was, and they hired, like, hundreds of people. And then he told the story, like, and then two years later, like, the whole thing had blown up and they'd lost all the money and it didn't work out. And, like, he was totally cool with that, and all the investors were cool with that. And, like, not in a bad or good way, in different way either. Like, it was, don't get me wrong, it wasn't like he was like, oh, screw it, we lost money. But it was like, here's a very logical story about how we Took a really big swing with a lot of risks that everybody knew and it didn't work out. And I'm back here to tell you the story, living it and we're still running formstack and everything's okay. And I was like just boom. Like Mind school was like holy shit, I could do that. Like how, how did you learn to do that? What did you need to know? And it was also kind of in the same like literally like a week long process maybe. I think it was a two or three day conference that I then found what these venture capitalists were and I found who like Brad Feld, Fred Wilson and Mark Suster were three of the original uh, like VC bloggers, early VC bloggers. And I found their websites and I went and read their, their content. And Crystal, uh, I think you asked how did I, did I put together uh, a plan or anything? Well, I went back to my apartment after that, that weekend and I found their blogs and I started reading it and I was like holy shit, this is the information that I've been looking for for the last four years. Like this is the whole reason I went to college was to find exactly what's written in these blogs and so

Speaker C: to read the Internet, my visualization was

Speaker B: like there's so much to learn. I know nothing about any of this stuff. But here, these are these world renowned efforts of entrepreneurs turn these VC things that uh, I just learned about that give other entrepreneurs money and not only are they out there but they like open sourced all the information on how they did it all. And I was like, I know nothing. My classes take way too much time. This is all the information that I want to learn and then to not give away the end. But then I dropped out of school literally the next week I quit going to classes. I got the first F I've ever gotten in my life. I kind of finished up the other courses. That was enough that I just needed to go take some tests and got those done. But there was this one design like Adobe class that I was like taking way too much time. I was like screw that class, I don't need to learn Adobe right now. And I basically locked myself in a basement for the next six to eight months and learned and read everything I possibly could. And so the original curriculum was just to read Brad Feld, Fred Wilson and Mark Suster's blog front to back, beginning to end and taking copious notes along the way.

Speaker A: This feels like complete cheating. But I have to ask the question because it's such an obvious question. What One or two things did you take from it. Like, what did you learn? What was the key at that point? Right. You've probably learned so much since then. Maybe things have gotten more complex, I don't know. But what did you take in that moment and say, this is the key that I have been looking for?

Speaker B: Yeah, it's a great question. I think if I deduced it down, it's as simple of like, learn than do like learning plus action. Like, it couldn't be theoretical and just, uh, academic or philosophical and learning this stuff. I realized very quickly after driving, like, I needed to start a company alongside this to practice while I was learning. And so in doing that, like, I found their blogs. I read two really impactful books for me around that time were Venture Deals, Be Smarter than your Venture Capitalist and Lawyer by Brad Feld, and then the Lean Startup by Eric Reese, which was heavily influenced by, um, Steve Blank. Those were like the two books, but then those led me into Startup Weekend and the Lean Startup Machine, which were these like weekend projects where you go for a weekend, you come up with an idea, and at the end of 54, 72 hours, you're supposed to have like a working prototype and pitch that at the end. And so I started participating in Startup Weekends. I then hosted a Startup Weekend. I went to the Lean Startup Machine in Chicago, uh, at that time, and then ultimately did what was called the Startup Bus, which was, which were eight buses that started around the country that all drove down to south by Southwest, my bus from Columbus, Ohio. And then you created a startup on the bus on the way down there. And so, so yeah, that's the big thing was that I couldn't just do the learning, but I had to do the action with it. And then just real quick, to answer your question, was there any other curriculum? So I put that together. But then I also learned that Stanford, Harvard and MIT gave away all of their courses for free on edx.org at the time. And that blew my mind. I was like, oh, well then I'm not going to take the courses that I'm assigned at iu, but I'm going to go take these other courses that actually have the curriculums of the everything that I'm needing to know. One of those courses that I took ended up being Peter thiel's very famous CS183 Stanford class, startup class in 2012 that Blake masters wrote the notes of, that the notes from M. That class that we went to became Peter Thiel's zero to one book. Blade Masters is now Ran for the state senate in Arizona last is running for a, uh, seat in the House in Arizona this year. But like that's mind blowing to me to think back that that was 14 years ago that I was in that class learning from Peter with Blake, taking those notes and that were, those were the notes that I was learning from. I'll just say I'll call that getting lucky.

Speaker A: Every successful person attributes some amount of their success to luck. And I think that's very admirable. I should say the good ones do. So I appreciate that. If I'm skipping anything, holler and shout. But it seems so obvious again, you said I can't just learn, I need to do so you do all this learning, you're taking these free courses, you're eating it up, you're ready. Can you talk about the. Do I know you started a company? Is this the time?

Speaker B: Yeah. So my goal. So when I dropped out I really, I had, I was on like a very real six month time frame that I had to figure it out, come up with a business and find a way to support myself before I was out of college and needed to get a job and pay for rent and all of those sort and life was going to happen to me. But I had this six month period where I was going to lock myself in a basement and learn as much as I could while only leaving to quote unquote, do or meet people. Two cool things happened during that, that time or maybe three actually. One, one of the events I went to was the the Verge startup events which are now Powder Keg ran by Matt Hunkler, still there in the Indianapolis startup community. And that at one of those events, one of the speakers was David Duram, the founder CEO of Greenlight Guru. And uh, he famously at this point jokingly, I came up and asked him some question of like what the square root of his cap to LTV for like some segment of his business. And he was like, well we'll take that question offline. And so that's how David and I, Greenlight Guru's founder, originally met was I asked him some really complex question that I didn't even know what I was asking at the time. We struck up a friendship after that event because I followed up with them and we both pulled out our notebook books to take notes and it's like did we just become best friends and took down some ideas? So that, that was really impactful. The, the other thing is I hosted a Startup Weekend event in Bloomington. So I had participated in one and came up with an idea for my first company. It was called Impulse Coupons. I don't know if you guys remember those coupon packets or Grace, I don't even know if they had them. It was like called Campus Coupons in Bloomington. And as a, as a broke college kid, I used a lot of coupons for the food and was always trying to save 20% or buy one, get one free here where I could. And so. But it was a pain in the ass to carry around a coupon booklet with you. That's not cool. And so in doing some research I had learned about this like around 2011, 2012. This solo mo craze was huge. So Social Local Solomo was what it was called. And I learned what a geofence was. And so the original app or original idea for Impulse Coupons was an app that had all of those coupons on it digitally. And when you would walk by a store that was giving you an offer, your phone would send you a push notification that says, hey, there's a Buy six free wings at Buffaloes. Get six free. When you, When I'd walk by and I'd go get my favorite wings down in Bloomington. And so that was the first idea that I did. I carried that through. I hosted a, uh, Startup Weekend in Bloomington towards the end of that six months. Which, funny story, that's where David and Greenlight Guru's very first angel investor first met was they were both judges at that Startup weekend. And then the third thing that I'll say that happened during that, that was impactful. So I knew I had that six month time period. I made it my goal to get into one of these startup accelerators like Y Combinator or like techstars at the end of that six months or into their summer program. If I didn't get accepted into one of those programs, then I was going to go back to the drawing board and, and either go get a job or try and figure out what else I was going to do. The third thing that happened, luckily I did end up getting into a program called the Brand Re Accelerator in Cincinnati, Ohio at the time. It was a top, top 10 ranked program in the country at the time. But how that ended up happening was I mentioned the Startup Bus that went down to south by Southwest in 2012. So that would have been what, March 2012. And I joined the bus we left from Columbus. But the reason that I did that was because I knew that GM of the Brandery was also going to be on that bus. And I took a wild guess that I thought that he may be scouting startups while joining that bus and why he was joining it. And so whether Mike Bot knows this today or not, I made it my goal to try to impress him while I was on that. On that bus. And lo and behold, it did end up working out and I was able to strike up a relationship with him and I, uh, think impressed him in some ways because, well, they didn't accept my idea of impulse coupons into the brandery. They did say, nick, we're not really behind this coupon idea and you don't have a tech team behind you, but we really like you. And there's this other company called Antics that we would love for them to join, but it's a developer and a designer. You'd be the back in the day called the Hustler, hacker and designer. We got a hustler and a hat or a hacker and a designer, but. Or hacker and a hipster. Hustle, hacker, hipster. We had our hustler and Hipster, but we didn't have our Hustler. And so we needed a business lead. And so they brought me in to be the third co founder of Antex to join the brandry. And that's how I ultimately ended up getting into the brand.

Speaker A: Absolutely unbelievable. You have like, my heart racing. Like, I'm like, with you on this story, I feel like I just lived those six months and I just have to comment that were those just the moments most unbelievable, impactful. Such a lame word, but has there been like a bigger six months in your life?

Speaker B: I don't know. To think back on it now, I think again, just great appreciation and uh, fullness for the, for everything that happened and a lot of luck and blessings of things that have gone my way. But at the time when I was in it, it was just like life or death. It was like, uh, I don't know. Six months at that time felt like a lifetime too. When I was sure, 15 years ago, at this point, like, it seemed like three years all in one. But yet to think back, and to think how crazy it was that it was only six months and like every. Every week felt like a month and now times and how fast that things were moving and progressing. So yes. And in those time, um, to look

Speaker A: back those six months, you learned you started a business, you introduced a future boss and someone who also, you know, you navigated a whole bunch with and then started on this brander. Eph, it's just, it's. It's amazing. It's so cool. So happy for you.

Speaker B: I, I appreciate it. I told you guys I was excited to have this conversation. You guys were going to let me have some fun and relive some fun memories here today, so, and learn alongside you.

Speaker A: This is good too, for sure.

Speaker C: So another fun memory that I uh, want to take us down is this, you know, intro into Greenlight Guru. So you have started a couple businesses, done some crazy startup accelerators, all of this like six month crazy period, but you ended up joining on uh, at this company, Greenlight Guru. It was very small at the time, but I'm just curious like what you, you had maybe a couple businesses coming into this beforehand. What made you decide to either leave those businesses or shut that down and then join Greenlight Guru or start a new business? Like what was the sort of decision there and how did you ultimately come to say I want to join this, this early stage startup versus starting, uh, one of my own?

Speaker B: Yeah, for sure. So I guess in one word failure. So that was a really fun six month period of learning and getting accepted and yada yada. And then the real world smacks you in the face and the market is the market and you gotta go make money and you gotta be successful and you gotta execute behind your ideas and visions. And so I will say over the next two to three years, I was then humbled by reality of being a founder and an entrepreneur in a good way and doing it with an optimistic smile and trying to keep my head up. But it was a lot of beating my head against the wall and a lot of no's and a lot of failures. And so I think those next two to three years in Cincinnati were also a, uh, very, very impactful period for me because I'd had a lot of success seemingly from these stories that I tell you. And it felt like a lot of success for me too. And this is where I kind of had some of my first real professional failures. And so that company that we got accepted into the brandry as within eight weeks or halfway into the program, I was the business guy like we said. I had ran every analysis up and tam research business feasibility. And I realized like even in our wildest dreams, if we were successful at executing this, like this wasn't a really big or meaningful company. Um, and we were going to have to sell 25% of every unsold sports tickets of the four major sporting leagues in the US for us to even like become break even and like be a big business. So I don't know myself. I was 22 at the time. I didn't Think I was going to be negotiating with the four largest sporting leagues in the US and figure out how to solve selling 25% of their unsold inventory when they hadn't figured it out over the last. So reality, yeah, reality set in. And so ultimately I was like, even if we love this and, and like, we're successful over the next three, five, ten years, doing this, like the ultimate outcome at the end of the rainbow is not a pot of gold. It's like a, um, shitty business. I say it tongue in cheek right now. No disrespect, uh, to my co founders at that time. And it was a great idea. It was like Foursquare meets Vivid Seats today with the technology. It made a lot of sense and it was great utility to the users. It was just going to be hard to make it a big business and it was going to be hard to execute for the people that we were. Um, that was the first tough decision was actually leaving that company and saying, like, hey, I gave it as much as I could over these last four months leading up to the brandery and two months as part of the brandery, but ultimately, um, left and joined one of the other cohort members in that first or that second class of the brandery. And I joined one of the other companies called Impulsity, with some great entrepreneurs, Hunter and Austin, that were amazing. They had built a mobile app that said what to do tonight? And so, like, if I was in a new city, like, I don't know if you're familiar with, like do 312 or do 317 or do 512 here mobile app version of that and help them raise $1.2 million from Cincy Tech. It was an amazing experience because I get to like, play point on the diligence and investor communications and help doing the research. And I got a C firsthand, which was like, I wanted to learn. Remember I was in this, like, like give myself a startup MBA mindset and get into an accelerator and learn from there. And so the experience that I want to have as much as, yes, we wanted to build a successful business, but I also had my own internal motivations of just wanting to learn and have these experiences and so getting to be ahead of growth and go through that experience and be in the investor meetings and seeing it all firsthand was fantastic. And we ultimately raised $1.2 million from Scentsy Tech and Mike Venerable and. And it was a great experience for me. Ultimately got the itch to want to go do my own thing again. And so ended up starting, uh, a media company focused on startups and entrepreneurs outside of Silicon Valley. Again, I thought I had a mentor back then that was uh, a professor of entrepreneurship at Stanford. And he told me this is for a lot of uh, younger entrepreneurs, operators, people earlier in their career. It's like he told me it's amazing what a couple million dollars will do for your life. You don't gotta swing for the fences and always be trying to build these unicorns, like try to get some stability and some early wins early in your career and it can have a massive effect on the quality of your life and the swings that you're able to take elsewhere. And so with that in mind, also knowing I wanted to stay in startups and having been hit in the face a couple times, I realized I still had a lot to learn before I was, was gonna try to build the, the next Uber, if you will. Like I now was humble enough to understand to know what I don't know and what I needed, continue to learn and wasn't ready to take that swing just yet. And so Nibblets was a great transition from where I was at to still being around startups, still being to get around investors. And my personal thesis on it was this is a way that I could meet other really successful founders and VCs, but then also be able to provide value to them that it's not just me, like, hey, I want to learn from you, but hey, I run this media organization that reaches all of these other influential founders and venture capitalists outside of Silicon Valley. Do you want us to write a story about you? Do you want to come speak at our event? Do you want to come to our private dinner? And it allowed me to network while also bootstrapping a business that the goal was to build the TechCrunch for everywhere else. I mean, we had some success. We built a, uh, large audience. It got over a million, uh, annual unique visits to the website. In 2013, Forbes named our semiannual conferences one of the top 10 must attend conferences for entrepreneurs in 2013. But ultimately, after about two and a half years of doing that, I realized it was never going to be as big as TechCrunch. And I wasn't going to sell it to AOL for $20 million like Michael Arrington did, but I did end up selling it for orders of magnitude less than that. But, and nonetheless it was a fantastic learning experience and built a real business and was able to say, even if, uh, a very modest one at that, had an exit under my belt and Grayson Then to lead up to the question you asked of like how do I then end up joining Greenlight Guru? And so I just sold that business or in the process of selling that business. And I'm kind of at this crossroads in my life. Uh, I'm about three years removed from when I had dropped out of school at that point. And I'm um, coming off the back of what I considered at the time three failed businesses. But you could say three businesses of varying degrees of learning experience that I like to frame it these days.

Speaker A: I like that approach.

Speaker B: But I was like do I go try to go out on my own again and take a swing and build another company or do I look to partner with another experienced entrepreneur who's had success us before and maybe not be the founder CEO, um, but could be part of the founding team and a ah, key executive from the early days. And so as I mentioned, David Duram was someone that I had met while I was in that six month period still living in Bloomington. He's also someone that I kept up over those two to three years while living in Cincinnati. Um, he had just sold his previous health tech business of 24 years for many orders of magnitude more. He said this engineer, John Spear had been bugging him for years to start this company. It was going to completely revolutionize the medical device industry. I was like cool, that sounds awesome. I know nothing about med device, I don't know anything about sas. Uh, sounds interesting though, tell me more. And then ultimately ended up joining as part of the founding team there after really seeing the market, seeing the opportunity and learning that the skill set that I had just built over the last two years, building niblets of uh, running events, building community, building an email list, building traffic, doing SEO were all the same skill sets that you need to build a modern go to market, modern growth marketing organization. I know Grayson, you got a lot of HubSpot roots. Like I was a, I was a very early HubSpot believer and learned a lot from the inbound uh, marketing methodology. And and when I took a look at our competitors at Greenlight Guru they were all legacy on prem software companies for the enterprise that were founded in the early 90s that hadn't updated their website since the early 2000s and weren't doing any modern online digital marketing. And I realized that this was also around 2012 when the uh, or uh, 2013 when the saying like every company is a media company started to become popular. And I realized was like we could build if I just ran the same skill set back and everything that I'd learned running a media company, it was literally the exact same motion to do the same thing for content. But one of my ultimate learnings was it's really shitty to monetize and really hard to monetize media companies through selling Google Ads and event sponsorships. And monetize is much better selling 30, $50,000 a year software contracts.

Speaker C: I like it. Well, uh, one of the terms that you didn't mention in your explanation of Greenlight Guru, but I know that you're a big fan of now, I'll say is this concept of vertical SaaS. And so I've got a couple questions about that. But just for people who have not heard of this term before, could you sort of explain what vertical SaaS is?

Speaker B: Yeah, for sure. So Greenlight Guru is one of the pioneer examples of vertical SaaS. And so the way I like to think at a super high level is vertical SaaS is software that's built for a specific industry. Like Greenlight Guru built quality and regulatory compliance software specifically for medical device companies. Whereas HubSpot or Salesforce are kind of the quintessential horizontal SaaS. Companies. They built a single product, marketing automation. I mean, they expand from time, but let's just call it HubSpot Marketing Automation and Salesforce CRM. And they take that single product and then they sell it to financial services, to education, to pharma doctors. Like, whatever it is, they take the same product, go to multiple verticals. Whereas with the vertical SaaS, you take this one product and you sell it to one customer. And then rather than taking that product and then selling it to pharma or aerospace or defense or, uh, food and beverage, you then expand across the value chain and you provide more value for that same customer and build more product specifically for medical device companies. And so like to think vertical SaaS is about who you're building it for and horizontal SaaS is about what you're building.

Speaker C: Gotcha. And, um, I know you mentioned a lot of competitors were a little bit more legacy, so maybe this doesn't apply. But would you say like Greenlight Guru, you know, vertical SaaS xyz, competitor of Green Light Guru, taking a more horizontal approach. Or how would you sort of describe like Greenlight Guru versus competitors? Because then I think of like medical devices, like you're not going to sell them to the financial industry, so it's almost like naturally vertical. But I guess. How are you thinking about that?

Speaker B: Yeah. So Greenlight Guru builds software that helps med device companies comply with, with a regulation called ISO 1345, which is the quality management software or quality management standard for medical device companies. The analogous ISO standard is ISO9001, which is a much more familiar standard. It's the quality management standard for all manufacturing companies across the globe. And so what was unique about Med Device though was that med device companies were regulated by the FDA and the EU to follow and implement a quality management standard that complied with the ISO 1345 regulation. Whereas like my dad's manufacturing steamer business in Fort Wayne, Indiana, it's best practice that they follow ISO 9001, but nobody's going to come audit them and shut down their business if they're not following their quality management system standard. And so what Greenlight and John's original insight was was design controls specifically was very different in how you did this process for med device companies than any other industry. And so Greenlight Guru started as a wedge tool specifically for design controls for medical device companies. And then we expanded our processes to pre market engineering or pre market quality management for MedTech and then ultimately a uh, quality management platform for medtech companies and then even broader than just quality management, but into clinical trials, into training and into other problem sets that these medical device companies were going into. Whereas we did have one kind of main, main competitor, I mean we had lots of competitors, but I'll say there was one other venture backed competitor that was most similar to Greenlight Guru. And ultimately when they raised their large Series B around the same time that we raised our large round from private equity, they took a horizontal approach. And so instead of going deeper with Med Device, they framed as life sciences versus just Med device. So that was one of our positionings difference. They did pharma as well, but their strategy was to become the low cost mid market solution across all verticals for quality management and to go into the cannabis and to go into food and beverage and to go into aerospace. Whereas Greenlight said no, those industries are vastly different. You just end up becoming one of those then legacy providers doing the exact same thing. And ultimately at the end of the day we're going to stick to our guns. And that was really hard. And a lot of VCs did not like that answer. And it's ultimately why we ended up bootstrapping instead of raising a Series A was because all the VCs wanted to tell us, you need to go to the other industries to expand your TAM. Your TAM's too small. Whereas now vertical SaaS is a lot hotter I would say in the VC community and the likes of Toast and Mindbody and Service Titan and Shopify have taught us that you can layer on additional products and these, particularly these fintech solutions. And now you look at those companies, anywhere from 50 to 90% of their revenue are coming from their ancillary fintech and transaction products versus the core SaaS alone. Now all of a sudden these TAMs are 2 to 5, 10x larger than they were before. And now that's a good investment and a good strategy and having that stranglehold makes, makes a lot of sense. And so yeah, we had competitors, but they ultimately took, took the other strategy.

Speaker A: I smile hearing you say that because I know that vertical SaaS and overlaying other technology is a, is something that you care about and believe in. And I hope we, I hope we touch on that. But I just want to give one moment for marketing. At Greenlight Guru, you started as young Nick, head of marketing. Uh, you were, I believe, head of marketing for 8ish years and exited as CMO Nick. Okay, that's a lot of growth, a lot of change, a lot of success as we know. Maybe we can just speak as like a leader. What changed? How did you evolve? Or maybe if you want to say this strategy piece really just, you know, was a huge pivot or something. But tell me, head, uh, of marketing Nick versus CMO Nick.

Speaker B: Yeah, I think it, you gotta transition with the company. And one of our, my mentors, our mindset coach, Kevin Bailey, likes to say the founder of Dream Fuel, uh, like growth companies are just a collection of growth individuals. And so when you're at a company that's growing 100, 200, 300% year over year, like everything's changing so fast, the job's changing so fast, the title doesn't matter as much. And so while my title of head of marketing more or less stayed the same for the whole eight and a half years or whatever, like what I did on a day to day basis changed dramatically year to year. Now in doing that there were some definitive switches. And I can say like why we switched the title was because the job was vastly different. But it also gives a signaling to the outside world of what it is. And so when I'm head of marketing Director of marketing Nick for the first three or four years, like that's very much a, uh, player coach role where I'm owning the strategy, but I'm also owning almost all of the execution of the strategy myself. Or, and, or with a small team of consultants, agencies outsourced, uh, development talent. When the title switched from head of marketing to VP of marketing. That was really when we doubled down on building out the team. And it wasn't just revenue marketing, but now there was inbound marketing. We were building a sales development team, we had a rev ops team, we were building product marketing and now I was building my leaders in each one of those, those sub departments. Now the VP title made sense because I was now managing a team of leaders that were then player coaches with their own teams. And so the title was a signaling to the outside world of what my role was internally and how that had shifted. And very similarly with then shifting from VP of Marketing to cmo, I now had a broader global view that also encompassed all company growth strategy, which also included pitching in around strategy. I interimly led our product department as interim CPO for a time period while I helped our CEO hire and backfill a, uh, chief product officer, but then also was very integral in our corporate development strategy which was about partnering, building and buying different companies. And so in that time as cmo, it was about standing up a new business line, new product, and then also going and acquiring new companies. And so that again was a different role than even owning or managing the execution of the day to day marketing strategy which then I had my senior director of marketing which was building his team of leaders underneath him and now he was more or less in the VP seat and I was doing a new job that didn't exist in the company prior to that.

Speaker A: Yes, I love how you just outlined that journey or that progression because I think, you know, the, this podcast is for future and current startup executives. So for folks who want to be in your role at some point or want to experience this journey, they have a really good idea of what to look for, um, or what would be expected in like the next step. So thanks for outlining that.

Speaker B: Yeah, absolutely. And I, I will say on the personal side and for the other executives that are trying uh, to do something similar would look to this like it was always in the back of my head, like, don't get taught, I'll be fine. Like it was always a constant battle to continue to grow myself and grow my skills to be able to do the next job and to be able to be ready and execute on what our next year, two years or even three year out strategy was. So it was always a constant battle of learning and scraping and learning and doing as a constant theme throughout my career to make sure that I had the skill set to do the next job when it was coming up, up. And so reporting to the CEO is always very open about that and my goals of wanting to continue to be that leader. And if we ever felt like that wasn't working out, we can have open and honest direct feedback to have that conversation. But ultimately like, yeah, it was, it was purposeful and it wasn't easy and it was a lot of fun doing it. And I think other people can do it too. It's, it's not the norm, but you have to be intentional about it.

Speaker C: Okay, so it's my understanding that, um, you started angel investing while you were at Greenlight Guru or did you. Wait, okay, so you're starting. What would you say your approach has or how, how has your approach changed over time from maybe that first couple initial angel investments where you're super excited, maybe you overlook certain things that now you're, you're like, nope, if this is it. Ah, but yeah, I guess just talk us through like how your approach to investing has changed over time.

Speaker B: Time, yeah, for sure. So I meant m going all the way back. I just always became fascinated with venture capital because how I got introduced to this tech stars world or tech startup world was from these founders turn or entrepreneurs turned VCs. And so I'd always just been super interested in the investing side and aspect of this business as well. When I started out, it was like, yeah, man, we finally had a liquidity event. We can make some investments. Uh, it felt cool to be able to, to, to look at and evaluate these different companies and to be able to participate and, and help out. And so but I was, I was very much a generalist. I had no focus at stage. I would look at everything from like idea pre seed stage to like series B companies raising like tens of millions of dollars. And then I also would look at everything from like SaaS to deep tech to crypto to AI. And when you're all everywhere, across everything, like you're uh, the master of none, basically. Like I was a Japanese and it was super interesting though because I got to see different maturities of companies, different types of founders, different business models. But ultimately my learning was like, I'm never going to be an expert in any of this. And if this is something that I want to make a career and be able to do full time, then I'm going to need to be able to get focused on what I'm doing. And so, um, I think it just naturally became a progression of like learning by doing again that I was going to need to get tighter around my focus if I wanted to make this a career long, um, term.

Speaker A: Yeah. You talked about Learning by doing. Can you just touch on that? What did you do? What mistake did you make? Uh, that, that helped hone your thesis?

Speaker B: This. Yeah, I would say two things that I did. One, I knew that I didn't have an investing history so I needed to get a view of the market really quickly. And uh, one of the hacks that I would, that I did that I would recommend to others that if you're an accredited investor and you can make angel investments and you're interested in this stuff, like go on Angellist and join a bunch of syndicates or go find the top, top 3, 5, 10 syndicates that are most interesting to you and you're going to start getting their deal flow and you're going to be able to look at these opportunities and you can make an individual investment decision on whether you want to invest or not. And the GP has already done all the work of doing the diligence and the other investors and you simply get to say yes or no. And you can, you can in your head kind of play uh, fantasy portfolio if you will as well of like, hey, I would have have invested this much if I had that much money, I would have played here. And you can kind of build your portfolio and build your decision muscle and come back and see if you were right or wrong. And that could mean putting 2,500 bucks or 1,000 bucks or 500 bucks into a company or it could make not even making an investment at all. But that was like the first thing that I did that I think I would recommend to others that are interested in angel investing or different groups like another one, um, Hustle Funds, Angel Squad runs a group that uh, I've been a part of and help out with and would recommend to other readers or listeners here. The other thing that I think I did right, that is a common mistake other angel investors make, uh, is writing too big of checks into too many companies too early and not planning for your liquidity and wanting to be in this for the long haul. And so luckily I didn't make that mistake of going and dropping large amounts of money into like a small handful of companies and running out of liquidity early to not be able to stay in the game. But what I did instead that I would also recommend to others and I've heard other um, GPS and other general partners, I mean at venture capital firms and other angel investors recommend to do to get started, is instead of going and writing 51, uh, hundred 250k checks into individual startups, like go write some LP checks into other emerging manager funds. And so it's very much feels like an angel investment. The sizes of commitments that I just mentioned, 50, 100, 250K is very similar to the size of what a traditional angel check would be. But rather than getting exposure to one specific company and uh, have all your eggs in one basket, you're now spreading it across the manager. You're going to get to see how that manager works, sources, deals, you'll be able to help with diligence, you can help source deals, you could get feedback and you can be a value add member of the community. You also, if you like working with startups, working with founders, it's a great way to be able to give back to the fund as well, to provide your expertise and resources to the fund. And so I'd recommend others if they want to get started in angel investing, like actually either one, get started through AngelList and do it through syndicates rather than going and writing your own checks into founders, companies, uh, yourself. And then also look at potentially lping into other emerging manager funds to be able to have a more, a better risk adjusted approach. If you're just looking at it from a personal finance standpoint, I just want

Speaker A: to say I'm curious. It sounds like you've avoided a few mistakes. Did you read like, did you just go learn again somewhere or do you have really incredible mentors or like uh, where would you say is like a good source for this information or for the information that you've gotten?

Speaker B: Uh, yeah, let's read it like that same mentor from Stanford told me it's like, like the people put their best shit out there online. Like if uh, people want to learn from me, like you could come have a two hour conversation with me or you can come listen to the startup executive podcast and hear like 80% of, of the good shit that I'll say and you'll get a lot. And so everybody wants to look good when they're public, whatever, whether it's a podcast, whether it's something else. And so you learn a lot about people by doing the research and doing the work. The problem is most people in this world don't do the freaking and won't do the research. They're lazy. They'll just reach out to you and say can I have, can we do a 30 minute coffee and 9 out of 10 times like I'm a very open and will take meetings all the time. But if I can tell like you guys have done your research and understood and asked super really good questions, it makes this A really fun conversation for me. But there's others that maybe wouldn't do the same and you can see that. And so yeah, I just looked at like who's the most successful angel investors in the world? And like have they written books, have they been on podcasts? Like what can I go learn before doing to not avoid uh, to avoid some of the mistakes that they had made. Our founder CEO at Greenlight Guru started going to JMI equities founder conferences and he brought something back to our exec team. That really stuck with me that the founder of JMI is up on stage talking to all these really successful large company founder CEOs and he's done extremely, extremely well many times over. And he's like, over the last 30 years, like what have I learned? He's like, let me raise your hand in here if you believe that learning from your mistakes is a, is a good way to learn. And like yeah, hell yeah. Like you want to learn from your mistakes. And he's like wrong. Learn from other people's mistakes and don't make the mistake. He's like, you're in a room full of your peers. Like what I've learned from doing this job over the last 30 years and seeing many of the most successful companies in the world, hundreds of billions of dollar companies like ServiceNow and Blackbaud, is that many of your problems are way more similar than they are different. And nobody's a unique snowflake enough in here that they probably haven't ran into at least a very similar flavor of the problem that you're running into. It's like be vulnerable and talk about what's really going on or you're not going to get anything out of this. But you should definitely try to go learn from other people's mistakes before you go and make them yourself. And so I, I do try to learn before doing, but not. You can't, you can't be stuck in analysis paralysis role. You do just got to get out there and, and shoot your shot at some point too.

Speaker A: Mhm.

Speaker C: So one thing that I want to touch on and uh, uh, I know we're coming up on time here but um, the transition from this part time, you know, angel investor to full time, more dedicated. This is what I want to do as a career I guess I'm interested in. You obviously had some experience but what is the difference in like someone who's a part time investor, maybe involved in some syndicates versus someone who is a full time investor? And does it feel like you're Sort of starting over or just how has that been in this little transition period?

Speaker B: Yeah, and um, 100% is a new career, like without a doubt. But ultimately at the end of the day I'm still a founder and an entrepreneur. Uh, it's a different kind of business. We go back to lifestyle businesses, venture backed business. And without giving away exactly what I'm doing, but a piece between the lines. Like if you want to do this full time, you got to take it seriously and you got to learn how to do it seriously. And, and I was lucky to be able to start to learn those ropes from some of the best in the world. Top tier PE firms, going through processes, being on the other side of the table and then also being able to have uh, some leeway with the checkbook and meeting other startups that we were looking at potentially acquiring or partnering with and getting to learn how to do the job firsthand and being able to source, strategize, negotiate and help integrate a an eight figure deal that we did out of Denmark was great learning experience for being a professional investor as well. And so yeah, it has been learning a new skill set. But just like I had to learn a new job every single year at Greenlight Guru and you're growing that fast over time. It's just a natural progression of what I've done as well. But don't get me wrong, like I went to Harvard Business School's executive education on venture capital and private equity. I went through know the Y Combinator of emerging managers as an accelerator program last year. Like I, uh, I'm doing my learning while along doing alongside it. But the difference between amateurs and professionals is really like consistency and process. And so if as an amateur I may be just shooting from the hip and you, you may make this investment there and if it doesn't work out, like the only one that's screwed over is yourself. But when you do this professionally, like, like you better have a really good process. You better be able to defend your decision making, you better be able to show your work and you better be able to show that you understand the responsibility and the accountability that comes with managing other people's money outside of just your own.

Speaker A: Yeah, Nick, this conversation has been so good. I want to just close this up with one last look back. You've shared a ton of golden nuggets, so many takeaways. But if we were to just look at, at young Nick again pre startup life, maybe you're going into school again, maybe you're thinking you want to do an MBA or something. Maybe there are people listening who are, uh, in that position. What do you want to leave them with? What do you want to leave the audience with, given your last 15 years of experience?

Speaker B: Yeah, I appreciate this one, Crystal Grayson. Really fun and enjoyable conversation. Really appreciate the, uh, well researched questions and conversation that we've had here. There. The one thing I'll leave everybody with is probably the one lesson that I learned growing up is that anything is possible and it, it's on you. Like, all the information is all out there in the world. Like if you want to get something, if you want to learn something, if you want to do something, like, go find the three to five best people in the world at that, learn everything you can from them and just go do it. Like, there's nobody who's going to give you permission in this world. Like, like, you just kind of gotta go figure it out. But it's all out there for you to learn. And so there really isn't any excuse. I, uh, mean, everybody's got different situations in life. And don't, don't get me wrong, but like, if you got a big goal or like you want to get after something or you want to get that executive position or you want to build this company or you want to get into that college, like all of it, the information is out there in the world and you just got to take a little bit of responsibility and, and onus and go do it yourself and you can. And there's people out there that'll help and ask and to give back. And I've been very blessed and grateful and appreciative of many people that have helped me along the way as well and mentioned, uh, many of them in this podcast. Reach out to myself. Like, I would love to chat with you just to show me that you care enough that you've done a little bit of your own work as well.

Speaker A: Love it.

Speaker C: Well, like Crystal mentioned, thank you so much, Nick, for coming on. This has been amazing. So much good knowledge and I'm super excited to get this, us out to the world. Just one last question for you. Where should people find you? Is there anything you'd like to plug? Uh, how can people get connected?

Speaker B: Yeah. Thank you. I'm mainly on LinkedIn. You can find me at Nick Tippman, Search my name, connect with me. I connect with most, if not everybody, who sends an invite. That's also where I post most of my content. But I'm also over on X, uh, at, uh, NTipman, two Ps, two ns. Uh, you can follow me there as well at. And yeah, as we've hinted and alluded to, I'm a, uh, founder of an exciting self stage business. I will say right now that I believe is a startup in its own right. But yeah, follow me on LinkedIn. There should be an announcement here in the next month or so that I'm very excited about.

Speaker A: Okay.

Speaker C: A teaser. I love it. Well, thanks so much, Nick.

Speaker A: Thanks Nick.

Speaker B: Thanks. Thanks Crystal. Really enjoyed it. Appreciate it.