The true cost of scaling 🧱 Joshua Dziabiak

Most people don't know what they're doing, and so it's okay to just try and be confident in trying. The fact that you haven't done it before, this can actually be an advantage. I think being naive as an entrepreneur is actually quite important. But I did, especially early on, I let that like eat at me from a confidence perspective, which really impacted my day-to-day happiness, if you will. Every story is different. Every business is certainly different. And you really need to listen to your instincts. Take stories like mine, yours, and use them to sharpen your own instincts. Don't use them as a literal playbook because it's going to be different. Founders generally have a very good instinct, but they get stuck on listening to everything else around them for too long, and they don't even realize that that's what they're doing. You want to perfect the product, you want to perfect the messaging. You have this thing in your head that you want to get the product to The reality is, is you could build the best product in the world, and if you don't have a good strategy to tell the world about it, it doesn't really matter.

This week's Millennial Master is Joshua Dzabiek, founder and CEO of Perigon. He started building businesses early, sold one before most people finished school, and kept going. From a rural farm to companies in media, ticketing, insurance, and data, Joshua has seen what it takes to get something off the ground and what changes once it actually works. In this episode, we talk about how to tell when you're no longer the builder your company needs, why distribution matters more than features in the AI era, and how to build products that can't be wiped by market shifts. Joshua, welcome to Millennial Masters. Where are you joining us from today?

Thanks for having me. I am based out of Austin, Texas.

So we're back to America this week. And I know that you grew up in a farm in Pennsylvania and you started building companies absurdly young. If I'm right, you were 14 when you started your first business. What's the story behind that? And did starting that early give you an edge that may— maybe not many founders get?

Yeah, I did. I did start my first business at 14. I don't know if I knew that I was starting a business. I kind of stumbled into it, to be honest with you. Essentially, I taught myself how to design websites the moment I got online at a very young age. This was before you would call it a blog. I think that's what they would call it now. So basically just a personal website, right? And I became quite good at designing sites, and before I knew it, I was having other businesses ask me to design their websites. This also happened to be at a time when most businesses were still not online yet, so it wasn't hard to find—

And it wasn't before Google even was a thing, right?

That's, that's right. Or if it was very much in its infancy, if it, if it was, was a thing. Yeah. And so turning websites into a business was sort of what happened organically for me. And then the next thing I knew it was growing and I started hosting the websites, suddenly had a full fledgling business. And it, it, it grew quickly. Again, timing was great. And I can't say that I knew exactly what I was doing at 14, but I was figuring it out as I went and ended up selling that business actually right before I turned 18 because it became so overwhelming as a teenager trying to manage a business and have some level of a social life.

What was the overwhelming part looking back now?

I think that because I didn't really have a lot of mentors or folks around me that had done that before, so I was very much figuring it out on my own.. And I think that the most overwhelming part was always dealing with kind of finance, taxes, the things that really do take some level of specialty knowledge that 14-year-olds should be trying to figure out on their own. And so those elements just really kind of stressed me out. And then between that and, and seeing my friends have a social life and me just working all the time, I, I started to realize that maybe that wasn't the best thing for me at that time. And somebody gave me an offer on the business that was way more money than I'd ever seen. And I wasn't really thinking about selling it, but when that number came across my radar, I decided that, okay, yeah, maybe it was a good time to sell it.

So it was just before you were turning 18. You basically had success before most people even finished their studies or had any context in life. I'm wondering, how did that change your relationship with risk and also money so early on in your life?

For me, I have never been one that thought a lot about risk, especially when you're young. I mean, I think those, those sort of thoughts just don't really cross your mind. You kind of feel like you're invincible in a lot of ways. But I will say that it, it, it showed me how if you just kind of put yourself out there, you, you gotta, you gotta just try, right? Like, I guess I feel like the, the thing that I did that, like I said, it kind of happened organically for me, but it was looking back, it was just me always trying different things that I was open-minded. I knew I was willing to admit that I didn't know a lot. And so I was always trying different things regardless of the risk. And eventually some of them would pay off. The thing about money, I mean, I've always felt that the, at least for me, the first few businesses that I had started, there really was a drive for money. I mean, I kind of started them to make money as a lot of entrepreneurs do, but the more I came into money, the more I had more money or more access to money or resources in general, the more I realized that it wasn't really that fulfilling. It was the kind of the art of business that really made me want to get out of bed in the morning, meaning creating something from scratch. So whether that was a product or creating a team and a culture, creating a new process, these were all things that I really enjoyed doing. And Those were always much more kind of lasting, especially the team part, the people part, than the money part. So my relationship with money, I guess, has really changed over the years. Probably easier to say once you start to get access to it, but the thing I think about now more than anything are the problems I'm wanting to solve in business and the people I'm surrounded with, because that's just when I look back, I don't remember the money. I just, I remember the people and the memories we create and the products we create and Like I said, it's kind of the art of it more than anything else.

So after you sold your first business, you could have coasted. You said it was an amount of money that you haven't seen up until that age, but you didn't. You still had a niche, and you suggested just now that this whole building part and creating something new led you to your next venture. So I'm wondering, what did you do next, and how did you go about it?

Yeah, I, I essentially the way that I'd always kind of started my businesses were there was an element of, okay, what, what kind of problem needs to be solved? Of course. And yeah, can you make money doing this? But I think even above all of that, it had a lot to do with just areas that I was intrigued by. For me, I grew up on a farm in the middle of what felt like nowhere. And so I was always fascinated with like the entertainment business, media, things that made the world feel a lot bigger and more exciting. And so like my next business that I got into was actually a record label because I had some capital at that point. I just sold the business and I was essentially to buy my way into it or invest my way into it. So I started a record label largely because I wanted to be surrounded by artists and to be in that space. And again, growing up where I did in the middle of nowhere, it didn't feel like there was, you know, an alternative way to enter the entertainment business. And so that's how I chose that. Also, it definitely helped that at the time MySpace was very much becoming, I think at the time it was like the second most pop, you know, popular site on the internet, vastly, you know, kind of growing and everybody was on it. And I saw this opportunity to kind of promote music through MySpace. And the idea was simply like, let's take the concept of a record label, which at that point was still very much heavy on kind of more legacy ways of marketing and physical CDs and things. And let's use MySpace and the internet and the advent of what became social media as a means to market and distribute the music. But it all began with just like an interest in being in the entertainment space, really. That's how it began. Yeah.

And that was ShowClicks, right?

No. So, so the, the first company I started was MediaCatch and then I invested in this record label called Next in Line Records, which ultimately did not go anywhere, but it did lead me to a, to my third company, which was a company called ShowClicks, which was also in the entertainment space, but it was a lot different in the sense that we were building software for event organizers and venues. And I learned of that or saw the need for that from my experience at the record label because our artists were going on tour and they didn't have any means of like distributing their tickets and promoting their events online.

And I'm assuming the artists had a similar problem to what they have today in the streaming world, where the main revenue that they were getting wasn't from their record label or from streaming, but from the live events and the concerts, which is why they needed this streamlining in terms of event management and selling tickets. So the need was still there and the problem you were trying to fix was still there.

That's exactly right. And it was only because I had that experience investing in that record label and working in that that I even would have ever saw that need, right? Because I'm not an artist myself. I've never been on tour. So it was just working with artists through the record label, having them go on tour and realizing that they had very few options of selling tickets in advance, especially again, this was, you know, 2000 and 2007, 2006. So this was a, this was pre, you know, platforms like Eventbrite. And so it was essentially Ticketmaster was like your only kind of means of doing something like that here in the States.

Same here in the UK, but yes.

Yeah. And so, so there was no way of, for like a smaller or midsize artist to distribute their tickets online. And that is. That problem is what I set out to solve with ShowClicks. And that business ultimately ended up doing very well.

But how did I— Over $100 million in revenue, if I'm right.

That's right. We had very much an organic growth story too. Like it kind of, of course, started real slow and it was a very hard sell because we were entering in a space that was very resistant to change and also very much owned and controlled by Ticketmaster, namely. And so it took a while, but eventually we started to get bigger and bigger contracts and yeah, it grew. I was there for 7 or 8 years and grew it to a little over $100 million in sales before I went on to do my next thing.

And you stepped away when things were objectively going well at ShowClicks.

Yes.

So how do you know when a company moves from the build stage and the scaling up stage that you've taken it through to the manage stage and you decide to move on?

That's a great question. And it's one I think about a lot because I I don't know if there's a, you know, single answer to that, but it, but I guess the pattern that I've seen, because this has happened to me a couple of times, is that work really starts to feel like work for me, meaning work in the negative sense, right? Like it feels like a job. For me, I really, as I mentioned, I really enjoy the creation, enjoy, you know, having this idea or somebody else having an idea, working to bring it to life. From nothing to something. And then there's a point when it becomes that something. And I think I still find it really motivating to kind of, you know, help get it to a certain level, whatever level that is kind of depends on maybe the circumstances or what it is I'm building. But, and then it, and then there's like this part where it becomes almost more like financial engineering where you're starting to say, okay, this is in market, this is even at scale. And so the moves making aren't big step function moves anymore. They're tiny incremental tweaks, if you will. And that feeling of financial engineering is just not what gets me out of bed every morning. Like, and so yeah, I, you know, I remember distinctly going into work one morning and feeling as though I didn't want to go into work. And I remember it so distinctly just because it was the first time I had felt that way. And it, and I felt, I felt that way just because there was a pattern where my days started to become less about innovation and creation and all the things that I really enjoy doing. And it became more about optimization and minor iterations. And, and you're not seeing the needle move quite as fast. And so that feeling is where I start to question, am I, am I still right for this? Is this still what I want to be doing? And then I've also been a big like I've never wanted to leave something whenever it's not working, right? Like whenever it's like having a bad day or a bad season, like I think there's something to like leaving when you're kind of on top.

Leaving on a high is always the best way.

Exactly. And it's hard, that's the hardest time to leave. And, but that's what I chose to do. I just felt that it was, it was time and that if I handed it to someone else that they would be better at the business required at that point.

And is there anything in particular that you took away from running a business that was generating more than $100 million a year that you wouldn't find in a business book or your typical accelerator that you took on into your next venture?

Yes, for sure. So in my, in my, in the early days of building ShowClicks, we did raise a little bit of venture capital. That was my first time, the first business I'd had, I just, like I told you, it kind of happened organically and it, I bootstrapped it. And so with ShowClicks, it was, it was a little bit of a different story and something I just did not know. I didn't realize, I thought was like an investor comes in and they want to see you hit a home run, right? They want to see you kind of grow this to as big as possible. Which in theory, I think every investor would probably agree with even now. But in practice, what I learned is that every investor has a different investment thesis and scope in which they invest, timeline, the types of things they invest. And then ultimately, they're gunning for a certain type of outcome, right? That may not be a billion-plus-dollar outcome. Maybe they want to put in a million and their kind of goal is to see the business get to $15, $20 million in revenue and exit for 4 or 5x that. And that's a big success story for them. But if you don't understand that and you end up surrounding yourself with investors that are in that camp, you can create a lot of heartache for yourself, right? So, so like something I learned is like, and I remember as soon as I kind of moved on to my next gig after ShowClicks was, was I need to surround myself with investors and folks that are like-minded and on the very outset have the same kind of like investment, long-term vision, kind of big picture thinking that I do and have the capital and kind of the firm behind them to support that thesis because ultimately depending on the type of business you're building, you may require a lot of capital, you may require a different type of investor. So that was one of— you asked me that question, that was immediately what came to my mind because that was a very hard lesson to learn because as a founder, it created so much confusion in my head as to why am I wanting to grow this business a certain— like, why aren't they getting it right? Like, because we never had at my— at ShowClicks, we never had that conversation like that, that honest, like raw conversation with the investor group and the board. Of like, what are they ultimately wanting? Right? I think there was fear on their end that they didn't want to put a smaller ceiling on it than, than I could potentially accom— you know, or something. But ultimately, once I realized that what success looks like for them is way different than what I had really been dreaming of for this, a lot of things started to click and make sense as to why, why they were giving me feedback a certain way and why they're kind of helping to drive the business in a, in a different direction or, or something. And so I, I immediately thought of that the moment I started my next company after ShowClicks was finding the right folks.

And so you had your first taste of investors. I understand from my experience as well, the first time you raise money from external investment, you just want to get the money and go on with your mission. And maybe you don't align as much as you suggested, but your next venture, Zebra, was a venture scale opportunity. Besides a solace business in a famously unsexy domain, insurance. It's something that is at the top of everybody's mind, but that's where you raise some real VC money and you saw a few changes in the moment institutional capital is on the cap table.

Yes, absolutely. I mean, so with, with the Zebra, you're right. Definitely not a sexy industry. Definitely nothing I ever envisioned being a part of. I, it's not like I grew up wanting to be in the insurance space, but I will tell you in this case, I really, I had this thing in my head where I wanted to build a consumer brand because everything I'd done up at that point was largely B2B. And it just was always interesting to me. I think, you know, I tend to lean heavier on marketing and product and things. So for me, like consumer was just always really fascinating. And I came across the guy who eventually became my co-founder with the Zebra um, while I was doing some mentorship and stuff in Pittsburgh, I was still the CEO of ShowClicks. I'd started to get that itch and started to feel like it was very much becoming work for me.

Mm-hmm.

And he presented this, this problem to me, which was simply insurance shopping sucks. Uh, people should be able to compare insurance.

It very much does, but—

And, uh, he presented this like the value proposition was, was very simple, very easy to understand, which is consumers should be able to comparison shop online. And I'd only even kind of heard them out because I had thought for sure this already exists. It just seems so obvious, so straightforward. And so I had actually done some research and the more research I'd done on it, I had saw that like in Europe, this was actually a very mature market, like comparison shopping for insurance or financial products was very mature in Europe. The companies like CompareTheMarket and MoneySupermarket, but in the States, these didn't exist. And again, I learned later why they didn't exist, but at the time I was very naive and I thought, man, what better space to try to build a consumer brand in? Because to your first reaction, it's not a very sexy space. It is a product that is often bought and not sold. And so it's required by law. And so people kind of have to do it.

And yeah, you don't think about a brand name or go for it. You just want to get the best deal.

That's right. Exactly. And, and it's, um, and so I had felt that there was an opportunity here to build something that was kind of much more modern and kind of rubbed against the grain of the stodgy insurance vibe. Right. And so that's when I set out to, to build, to build the Zebra. And yeah, we going into it, I knew it, it's one of the largest industries. It's very bloody competitive, especially when it comes to marketing and growth. And so I knew I was going to have to have some folks around the table that had deep pockets and that were very much aligned with that thesis of, of building a brand in that, you know, crazy competitive world. And so I made that a point on the very outset to do that.

And also the Zebra reached unicorn scale.

Yes.

And I'm wondering, what does that type of success start to cost personally? Because not a lot of people on this planet had a taste of that either way.

Yeah. It's, well, you know, it took us about 8 years to reach a, you know, billion-plus valuation. And it certainly did not happen, you know, in any sort of linear path. We had, I think that, I think that the, there's this like idea in your head when you start a business that, you know, you kind of, you kind of build out this like maybe either literal plan, right? Of an actual business plan, or it's just like in your head that you're going to kind of do X and then Y and then Z. In our case, and I guess in every case for me, like with my businesses, I found that you, the path is absolutely not linear and the path is very much if you really wanted to build something big, you often need to do things that you did that are almost against the vision in a way. Meaning we were entering a space that was very regulated, um, is very stodgy, um, complex. And so the players in the space are used to doing things a certain way, which was obviously what we were trying to disrupt. So we had to almost adopt their, their methodology first, which in our case was kind of just more of a lead gen style business, which again was like, mm-hmm. Almost what we were allergic to and what we were really—

And the commissions attached to it, which is pretty much how the UK websites and comparison websites work.

Yeah, exactly. But it's, it's a horrible customer experience. At least it was in the States because it was largely just companies collecting your information and selling it over and over again. But we had to kind of get into that because early on, because there was this element of like, okay, if we're going to change this space, we need to kind of get in on the playing field that they're currently on. And, and as long as we keep that vision, we will incrementally, we will get there. It'll take time and it did, but we will get there. And so going through that journey though, like to get to your question, was very, very confusing because it was a lot of like storytelling and visioning that was different than what we were doing often early on. But we had to sell people, certainly the investors on, hey, we're heading this path, which looks like it's like completely disparate from where we're wanting to go, but you have to trust us that in order to get there, we're going to need to do this first. And then we will evolve into what we want to. But that process is very stressful. It takes a lot of faith and you're constantly questioning yourself and every— because everybody's questioning you. And so you find yourself having to put on a brave face, smile, and like tell the story and get people fired up. And you're going to bed at night kind of like wondering like, I losing my mind? Is this really how I should be building this company? But ultimately, like, that instinct was right and it worked, but it was a very emotional, like, I guess emotional, yeah, but just very challenging thing to do. So I like to joke that it took like 10 years off my life building that business, but also it was, was challenging as it was, it was extremely rewarding as well.

Speaking of emotions, You also moved on from The Zebra, and everybody talks about starting companies. That's always the main topic, but not many people talk about leaving. And with two departures on board by that point, what was the hardest thing emotionally about stepping away? When you look back? They were your babies again and your choice to move on.

I think it's the fact that you feel like you poured everything into your business because you do, right? Entrepreneurs don't shut off their work at 5 or 6 o'clock in the evening. I mean, it's always on. And so you very much pour your life into it and everything around you takes some sort of sacrifice because of that. And when you get to that place where, where you're starting to think about, or you're, you're moving forward with moving on, there is a, there is a letting go that process. And I think is, yeah, it's not talked about enough, but it's, it's takes a while that really makes you kind of question a lot because you, you almost question your own ability, even though maybe my last company was wildly successful or is wildly successful. The fact that you feel like you kind of work yourself out of a role or you just poured all of this time and many years into it. And now suddenly, like, you're kind of restarting back from ground zero. I don't know. There's a sense of imposter syndrome because you're wondering, why do I no longer feel like I'm a fit in my own company, like, that I designed and I spent so long investing in? And so it, it, there's, there's a bit of it that, that, that, like, impacts your, your confidence level. And, um, I think the second time, like with, with, with the zebra moving away or moving out of management, it was a little easier because I'd done it once before. And I went into it knowing that I was going to go through this process of like detaching myself, trying to stop my head from thinking about it all the time and just trusting that there's new hands that are kind of taking care of my baby and they're going to do much better than I could at this stage. And so when you realize that, like you're, some, some folks are just like me. I'm, I'm not, I don't think I'm that person that's gonna take a company that's at $100 million and take it to $10 billion. Like I, I'm more zero to 100 sort of thing. So when you start to realize that, you can get over it a lot faster, but that process of going through it is very taxing, very stressful.

How do you choose your replacement?

Well, I, I would never choose the replacement in a, in a vacuum by myself because it's largely a team decision, especially the team, the team that will persist. You know, you want them to be excited about whoever it is that's incoming. But for this last time, I mean, I was, I was really, I really felt like the business had a lot of the foundational elements necessary to even continue to scale even as big as we had become without a ton of new product innovation or new verticals or anything like that. So I was really looking for someone that valued and understood the importance of product, but was really good with people management. And it kind of goes back to that financial engineering. They're really good at kind of staying course on something that, yeah, you're not making huge incremental gains, but you're able to over time continue to build through better relationships with customers and, you know, hiring talented people and retaining them. And so it's great people management and it's great communication skills and it's great like ability to work with larger figures where you're doing a lot more iteration and optimization and less like pure innovation.

Optimization was the word that was coming to my mind as well when you said that. Again, then you moved on in another place that was not the obvious next move with Gawk. What problem did you try to solve with that?

So I had coming into what my next venture after the Zebra was going to be, I, all I knew is that I wanted it to have kind of a bigger social mission, if you will, at its core. Because everything I'd done before was largely the genesis of it was kind of selfish. It was, I either wanted to make make a lot of money, or there was, in the case of the Zebra, I wanted to build a consumer brand. And in this case, it was like, okay, what, what do I want to do that where I feel like there's a real problem impacting the world, the people around me that I know, myself, that I feel like is not going to go away anytime soon. And in fact, is going to get worse. And a lot of what led up to Gawk was actually the 2016 election cycle here in America, where the issue of fake news was becoming kind of a mainstream Talking point. I had seen—

That was when America told the UK, hold my beer.

That's right. Love it.

Yeah.

And so, so the, the, you know, I had seen this kind of coming, I guess, because not necessarily the political aspect of it, but just the problem of how algorithms were serving content. Because keep in mind, with what I was doing at the Zebra, I mean, we were building consumer brands. So the oxygen of our business was very much like, well, can we attract eyeballs? Right? How many people can we get into the funnel? So marketing was P1 always. And so I had to get really good at understanding how content was distributed, how algorithms worked across the board, across pretty much every platform, certainly search engine optimization, social media, you name it. It always frustrated me on that end of it that as a marketer, I'd felt that we had to constantly serve up ads that were extremely sensational in order to get any Impressions served because as you, I think we all know now, it's all about click-through rate and engagement. Whenever other folks are serving sensational ads and you're not, you're at a disadvantage. And that really frustrated me because it just seems so backward and also kind of the opposite of what we were trying to, to really do in terms of building something friendly for consumers. And so I saw it coming, right? Because it was like, if the algorithms are only serving our content, if it's sensationalized, then that's the same for natural, organic, you know, user-generated content.

And I was in the news industry at that point, so I understand everything that you mentioned. And again, similar fake news or misinformation were circulating across the UK when it was at a crucial point in its history, as we look back now.

That's right. And the electric cycle, like, really brought that to the kind of everybody's attention. And it didn't matter what side you were on. I think everybody saw the problem and I was gearing up to have my first child. So that whole process, I'm thinking, man, do I want to bring, you know, a child into this world that it just seems so crazy. The things you're seeing and reading and hearing in the polarization. So that's, that was the genesis of Gawk was I wanted to start something that was working on the problem of misinformation. And, and information overwhelm. And my first stab at it was Gawc with like kind of this news application where effectively I was trying to give users the ability to compare news data across news sources and do it through kind of a mobile app. And ideally the goal was to become like kind of a go-to news, news source or news application that, that let people kind of have a better way of consuming, consuming news. So that's how I got there. And, and that was a kind of the problem I wanted to be working on, knowing that like, by the way, that that's not a problem that'll never go away and nobody's ever going to quote, like, solve it. But, but the, I felt that there were ways that we can help, you know, kind of outfit folks to better, better, um, you know, inform them so they had a better way of staying informed.

So what happened next, which will bring us into the current moment and your current venture at Perigon?

Yeah, I had, um, so, so I, I worked on Gawk. I got in the App Store and I got some traction. Um, and then I had my, my first child and that changed your perspective.

Changed.

It changed my perspective. It changed the amount of time I had too. But I took time off because it was, I had started Gawk more, more or less, you know, it felt a little bit more like a side project, if you will, or a passion project, I hear people call it. And I, I never intended I didn't intend to necessarily build it. I didn't have a revenue model in mind even. I was building it because I wanted to work on that problem, but I obviously knew that to actually build a business off something, you need to have some line of sight to revenue. And so when I took the time off from my firstborn and I thought more about it, I decided that, you know, I needed to figure out what it was about Gawk that was working, what wasn't working, and, you know, kind of enter, kind of almost refound it in a way in a different direction, kind of with the same core, like working on the same core issues, but just come at it from a different, a different way.

And there was a moment then when you realized that you wanted to go back to enterprise from the consumer space that you've operated in with your last two businesses. What's the origin of Paragon?

Yeah. So, um, between the time, you know, I had my, my first one and then, um, uh, eventually launching Paragon, I was looking at, you know, like I said, what, what was working with Gawk? All right. I had this app in the App Store.

Mm-hmm.

It got quite a bit of traction. We had decent user base. It was it was growing, not a ton, but it was growing. I wasn't, I wasn't really trying that hard at that point, but I was getting these businesses asking me about the data behind it because when I built Gawk, the whole goal, like I said, was to outfit consumers with tools to basically be able to filter and compare information. And so a lot of what we did that was different was the kind of in the background was, was data labeling, getting really smart about, kind of, uh, how to classify information, um, and to do it at scale. So these were things like identifying if a piece of content was largely like an opinion or an editorial piece versus like a hard news piece, or is it a paid news piece, right? Does this article, like, is it embedded with a ton of affiliate links? And then we would label and make that information transparent, and then people could filter off this information. Even went as far as the source data, like, is it coming from a source that is largely affiliated with like left-wing politics or right-wing politics? Is it a more neutral source? And so we had all this data that, that we got pretty good at structuring and mapping and labeling. And so these businesses were asking me, how can I get access to that data? Because for whatever their business use case was, but they had not seen data, at least news data structured or labeled and kind of organized in that fashion, like they were seeing it done through our news app. So I thought the data was really quite valuable. The other thought that crossed my mind was, look, if I could, if I could kind of empower businesses or other applications that already have a much larger reach than I have with my news app that's going directly to consumers, then I can make a bigger dent faster by kind of empowering them versus trying to go direct to the consumer and empower them. Them directly.

And so lucrative as well.

Yes, exactly. And then there was a clear, clear line of sight to a revenue model. That was really what led me to, to kind of rebrand from Gawke to what is now called Paragon. Paragon is a, as a math term means 360-degree. The thesis stayed the same, like let's outfit people with rich context and 360 view on every story. And let's, let's do it in a way that people can build on top of it. So Paragon started really as kind of a news API and news data company. And we've been evolving it ever since and making some like application layers and things on top of that. Essentially, that's what we're doing. What we were doing for consumers, we're now doing for businesses at a much larger scale. And many of them that have many millions more reach than, than I, I ever did with that news application. But that's kind of how we got there. From consumer to business.

So in plain terms then, Joshua, what does Perigon do that incumbents fundamentally misunderstand?

Well, we're, so it's important to note that when I launched Perigon, it was right around the same time ChatGPT launched. So there's this, there's a bit of a—

So November 2023-ish.

You got it.

Yeah.

And so there's a bit of like pre-ChatGPT and post-ChatGPT because we had spent, remember we had spent like a couple years building this like data pipeline and getting quite good at that. And then ChatGPT launched and like suddenly a lot of these ideas that I had in my head were much more possible much sooner than I ever thought.

Yeah, it was good at classifying things, going through content, looking through particular keywords, analyzing, distilling the information, creating the summaries. And filtering the news items or the content that you were indexing.

That's exactly right. And so, the more awareness ChatGPT got, which it got a lot of awareness very fast, the more we started using our data and combining it with the big frontier models, and the more possibility opened up. So today, we're very much threaded with AI in the sense that We kind of rebuilt all of our platform to be AI-native, AI-first. A lot of our data pipelines leverage AI. And so we ultimately built what has become like basically the first kind of AI-centric news monitor. And it allows users to, in their own language, tell the platform what it is that they want to track. This could be literally any type of event. It could be as fun and playful as I want to track I want to track, you know, Black Friday deals to I want to track layoffs at companies that are greater than 500 people in the southern part of the United States. So essentially it's constantly monitoring the web at scale. We're always ingesting kind of the latest news as it's published. We have very low latency, so it's between 5 and 10 minutes usually from the time something's published to the time something is fully processed through our platform. And we're looking for these objectives that people define in terms of what they're wanting to track. So, for example, if they're looking to track layoffs, right, like we're, we're kind of monitoring for any announcements or any news or even hint of, of a company laying off folks. And then we will structure that into a single event instance. So instead of the end customer receiving articles, which is like kind of what traditional media monitoring was doing was, hey, here's a keyword of layoff that matches the keyword you're searching for. Here's the article result. What we're doing is, um, with AI is like we're, we're casting a wider net. So we're not limited to just whatever keywords are set. And then we are using a series of agents to essentially validate and then research if further research is needed and structure that into a single instance. So then what you end up having is, in this case, again, using the example of layoffs, you have an ex— almost looks like an Excel spreadsheet of every single layoff, right? With the columns of the data, exactly the data that you're wanting for this particular event, deduplicated, you know, researched, cited with the, with the sources in it and allows it to be indexable, searchable, and people can connect it to their favorite tools and apps. So it's a whole different shift. I see this as a step function change from where media monitoring has been to, you know, more true event or contextual intelligence. And of course, it works brilliantly with the LLMs. So feeding context right into the LLMs for kind of more real-time information is another popular use case we have as well.

So what would you say, Joshua, is the hardest thing about building in the AI and data space right now that people aren't really talking about?

Well, I would say the speed at which it's moving. So look, like, I, I think that there, so there's a lot of innovation happening very fast. I think we all know that, but it's also very hard to distinguish what is, what is real. And I'm not just talking about news and content, but I mean like product-wise as well, right? Like a lot of really beautiful 20-second demo videos that if you pay too much attention to that will start to make you feel very inferior because you start to feel like everything's been solved and And to the extent it hasn't been solved, somebody's solving it right now and will tomorrow, and your startup's gonna die.

Or at least they're promising that they do.

Right. That's exactly right. It's, they're promising that they do, and you gotta figure out for yourself what's under the hood there. But I think the speed makes it challenging because, you know, as an entrepreneur, you wanna have conviction around what you're building, right? Like, it's hard. It's very hard to build a company, you know, whether it was before generative AI or, or now in the midst of it. It was always hard, but it's particularly hard if you don't know, um, you know, what you're building is going to be relevant tomorrow. Uh, it's like you start to feel some kind of way about that because if there's hard times, you want, you need to have that level of conviction. This, and the speed at which things are moving, I think makes it tricky to feel confident at times.

And if I would try and touch the point, which I've heard from other founders and many people discuss, there's this general fear that in a way any LLM model or say the ChatGPT app, if we would name it directly, could incorporate such a feature that would then make your product or service irrelevant. Case in point, ChatGPT, for example, now can record your local audio and then transcribe it, so you won't necessarily need to pay for an extra service to say, transcribe your calls and create summaries.

That's right. That's exactly right. And, and then there's, so there's the kind of like direct kind of feature release or new tech that they might roll out that has a direct kind of obvious competitive stance on whatever it is that, that you might be building. But then there's also, there's also the indirect, meaning the paths of AI, the paths of Gen AI or new tech that may solve the problem in a way that you might not have even thought of, right? So as an example, I'll give you an example of that. So whenever ChatGPT kind of came onto the scene and Gen AI was really starting to become all of the buzz, I remember having conversations with investors and folks about, hey, we were in the business of being really good at kind of real-time data, real-time context, and these frontier models are obviously trained on data up until a certain point. And so there was a long period of time there, right? Where when you asked ChatGPT about anything that was of any recent happening, like it had no idea, and it would just tell you that. And I remember telling investors that LLMs will never be able to train on data as fast as the news moves, which is still true. But what I did not think of was this technology, which has become, call it Retrieval Augmented Generation, right? RAG, where the problem isn't that they have become able to, you know, train on real-time data quickly. It's, it's that you can essentially just apply search results, if you will, or, or, or apply real-time information to an LLM and ask it, right, for, for the answer. And now, when I say that out loud, it sounds really obvious, but at the time, like, never thought of that being like an alternative way.

And that's pretty much what we would say is the deep research mode in ChatGPT, for example.

That's right. Like pretty much any of the AI search-based products are using the term as RAG or Retrieval Augmented Generation. And, um, and so it's become like normalized, but prior to that, like I said, I thought the real risk was that LLMs becoming, it becoming possible for them to train on, on real-time information. I didn't think of it being like, it didn't matter. It was more, you could actually just give it the real-time information and then let its trained data answer, um, you know, any questions using the combination of the two. So it's just like this, you have this like direct kind of like concern of like direct feature or direct, uh, technology that may be the threat, but then there's also the thing that you don't know, right? Like the, the approach that may just catch you off guard given how fast things are moving.

And if things are moving this fast and previous guests on Millennial Masters mentioned the same, it means that you also have to keep up and/or stay ahead one step at least when it comes to that. So where do you find the inspiration for that?

Well, I, I've actually lately have been trying to, I won't say disconnect, but backpedal a little bit on how much I pay attention to all of the latest and greatest because it could be very distracting and also So if you let it, it can, like I said, it can start to eat into your confidence, which then plays into your conviction, which has a bad side effect to it. So I think there's a balance of like, okay, what do I really, what should I really be paying attention to? Also, what is real, right? Versus what is more smoke and mirrors or hype? Other than that, I, you know, I've been thinking a lot about distribution more than anything. How do we differentiate with distribution? So less about features or bells and whistles of the product., and more about how do we adjust the product or, or kind of evolve the product for, you know, distribution sake, getting it, getting it, kind of embedded in or, connected to some element that gives you some unique advantage that is harder for others to come in and disrupt. And I think that's just a matter of constantly looking at how people are consuming information, where they're consuming it from, and looking at what is working in this space, especially with new AI products. And how can we, if at all, how can we connect with that? Right now, I'm not thinking about always like trying to drive people directly to our platform and our technology. We think we win if people can set this up once and never have to necessarily come and see our dashboard ever again. Yeah. So the distribution piece, I think, is more important than ever, even in the earliest of days. So that's where we spend most of our time, I guess, in terms of innovation or thinking about staying ahead.

Now, Joshua, I'm wary of the time, and I'm hoping we can start closing with a few reflective questions on all your experience so far. So I'm wondering, across everything you've built so far, where do founders become the bottleneck in the business without noticing?

I think that there's— that's a really good question, Daniel. I spend a lot of time just on simple impact versus effort analysis because I find that there's generally only like a couple things that really matter, and the hardest part is distinguishing what those things are, right, from the noise. I think that entrepreneurs will— they're usually very curious people. I know I am. I'm always wanting to know more about whatever topic or about somebody and their background. I like to pick people's brains. I like to hear their advice. I like to hear their perspective. And I'm sure folks listening to this, that's why they tune in. And I think that's super valuable, but I also think it's really important that founders realize that every story is different and there's going to be things that you could take from my story, from your next guest's story, but it's not that there's any one thing that's going to work for everybody. So I find that founders will kind of subconsciously hear things, advice, especially if it comes from an investor or a successful entrepreneur or something, and they will, they will start to try to pattern match on their own and they will get so fixated on something that they heard and executing in a certain way that they forget that that may not actually be the signal in the noise that actually matters right now, right? Whatever that issue is or whatever it is they're trying to solve or the way that they're trying to solve it. And so I think that it's important that folks realize that every story is different. Every business is certainly different and you really need to listen to your instincts. So take stories like mine, yours, and other guests that are on this show. Take, take those, but use them to sharpen your own instincts. Don't use them as like a literal playbook because, because it's going to be different, right? And I just found that founders generally have a very good instinct, but they get stuck on listening to everything else around them for too long, and they don't even realize that that's what they're doing.

So finding inspiration from other, other people's stories, not as much in the particular methods they applied to address or fix a problem.

Yeah. Oh yeah. And asking yourself, is this right for me? Right? Like, like I think listening and having an open mind is good, but there's also like, there's that element where if it instinctually doesn't feel right, there's probably a reason because if you're starting something, you're in this every day, you're thinking about all the time, you may not have the words to articulate why or how, but you just may feel a certain way. And there's a lot of value to that. I mean, I sit on boards and work with entrepreneurs all the time and I will tell them sometimes, like, I will preface things by saying, cause they'll ask me, hey, how do you do this? Or, and I always like try to preface it with like, I'll share with you my take and my like 2 cents and my knee-jerk reaction, but take it and think about it in your context. And, you know, does it feel right for you? Because it's so easy for or at least, you know, I know myself, but I see other entrepreneurs do it too. It's easy to just get caught up in like specifics and stuff.

And that's what I wanted to ask you for my next question, because you have been mentoring, investing, been on different boards. What's the part new founders still lie to themselves about when building a business?

That if they build it build it, they will come.

Okay.

So I think it's so easy. And by the way, I'm, I'm so guilty of this even now.

Aren't we all?

And where you want to perfect the product, you want to perfect the messaging, you have this thing in your head that you want to get the product to. The reality is, is like you could build the best product in the world. And if you don't have a good strategy to tell the world about it, it doesn't really matter.

So distribution and getting your products or service out there, which is also something that we've heard throughout the last few episodes of Millennial Masters. In the era of AI where you can build your product either quicker or cheaper than before., but the problems of distribution and sales remain the same.

Yes.

Yes. So with that in mind, Joshua, if someone is listening and they're early in their business development, what's one decision they should slow down on, you think?

Their first couple hires or their, or, or found like co-founders that you're, you're getting in bed with somebody. You're, it's like you're putting a ring on it. You need You need to be extremely thoughtful of that. I think it can make or break the idea, the business, your own personal motivation. So don't take that lightly at all. And they really should complement you. It should be a yin and yang sort of thing. If they're good at the same things you're good at, they're probably not the right partner.

And if they're already scaling, is there one thing they should stop pretending that it will fix itself?

I think the— I kind of go back to like the product, like the perfect product sort of problem where or they think that just the next feature is going to change the game or win the deal. It's just typically not the case.

And finally, if you could send a message to 14-year-old Joshua in a farm, Pennsylvania, what would you advise him based on what you know now?

Most people don't know what they're doing, and so it's okay to just try and be confident commitment in trying. And, you know, the fact that you haven't done it before, this can actually be an advantage. I think being naive as an entrepreneur is actually quite important, but I did, especially early on, I let that like eat at me from a confidence perspective, which really, I think, kind of impacted my day-to-day happiness, if you will.

Well, not the first time, and I'm sure it's not the last time I will hear that naivety is a superpower in business, especially in the early days. So I think that's a great thought to wrap up today's episode. Thank you so much, Joshua, for coming on Millennial Masters and sharing your journey and your lessons so far. And I can't wait to see what you're going to be doing next with everything you're working on.

Thank you, Daniel, appreciate you. Great to be here.

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