Neil Patel

I hope you enjoy reading this blog post.

If you want help with your fundraising or acquisition, just book a call click here.

Jason Flick has founded several tech startups. His latest venture was recently acquired by AT&T’s WarnerMedia for more than $100M. He has acquired funding from several top-tier investors like FedDev, Sky UK, Causeway Media Partners, and Kayne Partners.

In this episode, you will learn:

  • Credit cards
  • Strategic debt
  • Venture debt
  • Bridge financing
  • Convertible notes
  • Venture capital
  • Private equity
  • Government funding through the IRAP program


For a winning deck, take a look at the pitch deck template created by Silicon Valley legend, Peter Thiel (see it here) that I recently covered. Thiel was the first angel investor in Facebook with a $500K check that turned into more than $1 billion in cash.

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The Ultimate Guide To Pitch Decks

Moreover, I also provided a commentary on a pitch deck from an Uber competitor that has raised over $400 million (see it here).

Remember to unlock for free the pitch deck template that is being used by founders around the world to raise millions below.

About Jason Flick:

Jason Flick is a veteran in the world of enterprise growth and management, having founded and scaled a number of successful software companies in the past, most notably Flick Software, Eftia, and N-Able.

Jason Flick believes in disrupting the status quo, which is what led him to start You.i TV with co-founder Stuart Russell. Jason Flick is currently a sitting member of the board for Invest Ottawa and Startup Canada, in addition to advising and mentoring emerging tech companies.

Jason Flick is a sought-after speaker on the topics of media, innovation and entrepreneurship, including TEDx and Variety Entertainment & Technology Summits.

Connect with Jason Flick:

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Alejandro: Alrighty. Hello everyone, and welcome to the DealMakers show. I’m very excited about the founder that we have today because it’s not the typical founder from Silicon Valley or from New York City. He’s actually a founder from Ottawa, and there’s a lot of great stuff happening in Canada, and he’s done it multiple times. He actually just recently did a really good exit, and we’re going to be covering that process and that story. But without further ado, let’s welcome our guest today. Jason Flick, welcome to the show.

Jason Flick: Thank you very much. I’m looking forward to spending time with you.

Alejandro: Originally, you grew up in a small town in Canada, so how was life growing up?

Jason Flick: Yeah. In a small town, there’s not much to do. You certainly had to go find your own things to entertain yourself. Luckily, it was in the early days of technology, so my dad was fortunate enough to buy me a computer, and that was, I would say, almost dwarfed. I think the relevancy of just doing a lot of odd jobs is, you learn what hard work is when you’re in a small town. Tobacco was a major industry in our town, so learning what that was, and yeah, I fell in love with computers and started coding at age seven or eight – Timex Sinclair 1000 or something, with 4K of memory.

Alejandro: That’s amazing. What do you think really got you hooked so much to computers?

Jason Flick: I think like a lot of entrepreneurs – ADD – can do two things at once, always wanting to keep things going. So technology allowed me to do that. Anytime I could get on that technology and figure that stuff out, I think it really engaged me. So, I was self-taught in a lot of cases because, in those days, there weren’t a lot of computer development courses available in high school.

Alejandro: And very early on in your career, you actually landed big responsibility jobs, and starting with being at the airport. What were you doing at the airport?

Jason Flick: Yeah. It’s funny. It was my first year of university, and I ended up funding my way through the university, which is always a good lesson. The airport was close by the place we stayed. They had recently acquired a piece of software from someone whose health had been diminishing. It was done in Visual Basic, which, at that time, wasn’t too cool, but they had been working on it for so long. I was able to take over the entire operation for that software for the airport. It was a government-run airport. It was smaller than the main one, and a lot of diversity and experience learning how to do the requirements-gathering. I sat at the airport coding, so I got to see it in action. There were a lot of really good lessons. I was VP, CEO, QA, tester, developer, designer, architect, all in one, so I think it was a good foundation for my future jobs.

Alejandro: Talking about future jobs, you did bounce quite a bit as an engineer before you actually went at it as an entrepreneur yourself. What do you think was the catalyst for you to say, “You know what? I’m going to go at it.” You were working for companies like Libraxus, TouchLink, Eftia, and all in the engineering departments, and there are great things that you learned along the way. I think we’re talking here maybe about five or six years that it took you until you actually went at it. I’m sure that you learned a lot. What were some of the biggest lessons that you learned, and what was that time where you said, “You know what? Perhaps it makes sense for me to go at it as an entrepreneur.”?

Jason Flick: I think the good thing is that I always had some sort of business insight that I knew as an entrepreneur, but I also knew technology is where I wanted to do it. You do need to become a bit of an expert. It’s great to be a bit oblivious about how painful it will be to do something or how long it would take, but you do need to be a subject-matter expert. For me, I stayed committed to those years to working my way up, learning how to develop it, and learn how to manage people, and learn what the real ins and outs are for running a business before I did it. I think I would have even continued a bit longer if I had the choice, but the big tech meltdown happened in 2000. Our city, Ottawa, 80,000-some people out of a million people here were in tech, and half of them were unemployed at that time. So, “Okay. I guess now is the time to start my business now that there are no jobs.” It did trigger that event earlier, and I’m glad it did. But it meant that I had to learn a lot more on the job.

Alejandro: I hear you. Let’s talk about N-able Technologies, which was your first company. How do you come to the realization that it’s time to take the leap of faith?

Jason Flick: That was a bit different in the fact that there were a bunch of us, and there was a complete reboot of what was there. But that was the first time it was at ground zero – reboot brand and reboot what we were doing, took on a C-level role, built that team. We probably added 50-60 people quickly. We got product/market fit very quickly, and then September 11 happened, and that ground that down. That business was on and, of course, sold. It went on for the next 15 years and did incredibly well selling the SolarWinds and getting a huge footprint in that space. It had a really tough run after September 11. Watching out for these inflection points is so key for what you’re trying to do. Yeah, that slowed them. They were right at the point where they could have either dominated that space and then they got shut down for quite a while.

Alejandro: So, you ended up leaving. Tell us about leaving your baby behind to go and start another one.

Jason Flick: Yeah. I think the big lesson learned there is that sales and just how important that is. People who love technology love to sell to people who know technology because they get it. But we really simplified the process there. I think that was my big lesson there. In fact, we got to the point where the core focus was on these hardware sale companies, which were making a 2% margin. This is 20 years ago – 2% to 3% margins. We were going in and taking a piece of software and giving them 30% to 40% margins, boot camping them, so they could understand it, and they would put this off on their client sites. So, to me, I learned: technology is great, and you’ve got to make it work, and I thought, as an engineer, that was what mattered. But really, I learned about the whole ecosystem, and if you need to, you need to become a training firm. So, we created a whole group just to boot camp these companies that only do hardware into software. I certainly learned a lot of that, but it’s always tricky when there are a lot of co-founders and different aspects to it, and I really wanted to do something on my own and be able to lead it. That’s when I went into Flick Software.

Alejandro: What happened next with Flick Software?

Jason Flick: It was in the middle of a tech meltdown, so there was no funding available. I said, “Okay, we’ll make this a service firm.” A lot of the business prior to that had a service component, “So we’ll start off with services, and we’ll find cool projects. We’ll learn about it. I’ll build a team up, and then when we find the right opportunity, I’ll have the funding, the capital, the team, the office space to jump on it. We did a whole bunch of projects for Amtrak, and museums, and the military and learned a lot about mobile tech until the iPhone came out.

Alejandro: What happened with the iPhone?

Jason Flick: We were at Flick Software. I ran into my co-founder, Stuart Russell, who is a brilliant scientist and developer. I hired him on the spot into Flick and said, “I’m going to make you a part of this thing that we’re figuring out what’s going on.” The iPhone came out. We got our hands on it and played with it. Really, we looked at it and said, “What’s the difference between an iPhone and a video game?” I had given it to my wife, who had had all the previous Blackberries and Nokia’s. She wanted nothing to do with them. She loved the iPhone. I gave it to my two-year-old daughter at the time, who had no clue what it was. She hated all the previous Blackberries and Nokia’s – she loved the iPhone. We said, “This is a transformation in how people relate to technology, and Apple’s not going to license it.” So, we actually created a complete clone of it. Again, this was around 15 years ago, and we were the #1 tech video in seven or eight companies for quite some time. We got 2,000 to 3,000 emails from this complete copy of Apple. Then, they threatened to sue us, and we backed down. Of course, it wasn’t the intent. We just wanted to show that you can take these kinds of great experiences, and we had them working on all the hardware that wasn’t like Apple. This is something we want to spin the business up on. We went on the homepage of Gadget for a while, which really helped. We said, “Let’s start our own business.” It took us a few months to come up with a name, spun it out of the company, and really doubled down on taking this incredible experience that Apple gives you and enabling it for everybody to have it. So, instead of working literally with hardware vendors like Sony and Cannon and Cobalt, up here in Canada, to give them Apple-like experiences.

Alejandro: It’s interesting because Flick Software was the segue for you to your biggest success today, with an amazing outcome. But I’m wondering – Flick Software didn’t have the outcome that you had desired, and as they say: you don’t learn so much from successes; you learn more when you haven’t been able to get it to where you had expected. So, what lesson was there for you to be learned?

Jason Flick: Yeah. Wow. A lot. I think the biggest one that I took into UI was the fact that technology is becoming a commodity. When I started that business back in 2000, it was really cool to get information in your hands to go to a mobile worker and give them a piece of data that’s useful in real-time. But that was not enough now. It had to be usable. It had to be engaging, and they had to want to use it. So, mixing art and science was a big lesson I learned. We didn’t even, at Flick Software, say, “Oh, you want this coded. Right? It will be this much money to code it.” And we didn’t even budget for design. “We’ll just use some clipart.” We were so bad. I think that’s a big one. People, for sure – one world-class coder can do what a team of five or ten can and getting the right team in place. At the time, we had no budget, so it was a whole collection of people, many which couldn’t get jobs because of the tech meltdown in 2000. So, I certainly learned that you really need to get the right people, and at whatever price it costs, you need to get them. That was a big lesson learned for me, for sure. There’s no commoditization for that kind of building new things. You’ve got to get the right people.

Alejandro: And almost in parallel, you had started You.i TV. That’s pretty interesting. Tell us about how You.i TV comes into the picture and how you worked to bring it to life.

Jason Flick: I think I realized almost immediately that this was going to be a complete cultural change. It was almost an inflection point in my life for my career where I knew what I had done and how I had done it in the past and it wasn’t what would work going forward. So, I immediately spun it out. I was able to leverage a lot of the infrastructure and some of the connection and things through Flick Software, but it was its own entity right out of the gate, and they helped each other like when one had a good quarter, and the other one didn’t, so they were helpful to each other. But, yeah, I created this separate entity as quickly as I could move that team that made sense into there and put my focus as much as I could onto that one. But it was a few years, too, where you’re trying to balance both. I was CEO of both companies – showing that you care about both, trying to grow both, deal with what are the biggest issues across two companies? Ultimately, I think it’s very hard to do. If one is a high-growth company, I don’t think you can be the CEO of two high-growth companies. Eventually, I did get CEOs and let Flick Software just be a sandbox for some other entrepreneurs to try things out.

Alejandro: In You.i TV, what ended up being the business model?

Jason Flick: Initially, it was helping hardware companies. The first four or five years, we were, “Okay. We want to help companies compete with the iPhone, just in general, the great experience.” We did a pro-device model, royalty model, just pretty typical – $1, $5, $10, depending on what the hardware was. But after doing that for about four years and building up a lot of the core IP, Stuart, my co-founder, was a good piece of it. We had to build a lot more on top of that. We would be building these platforms, and we would show them, one of our customers, a lot of these Tier 1 electronics manufacturers, “We have this great experience we built, as you asked. By the way, look. It works on all the other devices.” That was just weird for them. They wanted to know that they had built something customized that could only run on their hardware. We learned pretty soon that we weren’t firing all of the cylinders. I had also looked at a couple of other companies. One of the companies we were modeling ourselves after, which got bought by RIM, was [14:05]. I spoke to the founder there, and their cap was, all these hardware manufacturers have accounting systems that will never let any one software get on more than 20% or 30% of their hardware. I did the math. We’re going to get capped really quickly with this market. That app market, of course, was now picking up, and apps can get on any platform, and you charge your license on top of that. We quickly changed to a model where it was per app, and we went more after TV because TV needs to get everywhere. The unique thing that we did was that we brought video game thinking to the app market, and I still think no one has done that yet, and now, it’s in the hands of AT&T and Time Warner. This idea that you can have got right to the metal and get a great experience, that was the key piece. Then, we said, “We’ve got to focus on app stores. There’s no limit – 10,000 apps in the app store. They all pay us a license fee.” So, it broke that issue that I had seen this company that we were trying to model ourselves after a bit, and that let us scale the business in that market, and then focus on TV, and we went after the major media brands.

Alejandro: Obviously, here, there was a really big breakthrough for you when it comes to really understanding the importance of customer focus. Tell us about why customer focus was so important for you guys, and how should some of those entrepreneurs that are watching and listening right now think about customer focus for their own business?

Jason Flick: Yeah, those are the hardest ones for leads to come in, and you say no to them. One of the things I learned at Flick Software was that if a big company wanted – we did a bunch of things in the kiosk space, too, because it was mobile tech. We would go and bid on a solution. We could do it for $1 million. Another startup that was only like 4 people said they could do it for $100,000, and then if IBM bid on its $10 million. We learned that the scale matters a lot in terms of the client and how much they wanted and why try and struggle in those low-rent markets? That was the choice we made. We wanted to build a premium product. That changed a lot about who we wanted to focus on. But also, I think we did a lot of work on who are the profiles for our clients? I’m a big fan of crossing the chasm. Okay, great. We haven’t crossed the chasm yet.” This idea that you can write one app, which is more like a video game than an app, no one’s done it, and no one understands it. So you had to find these agents of change. But we also knew that we wanted to do a premium solution, so it couldn’t be an agent of change running a small firm. We had to hunt for these profiles of people that wanted to make a name for themselves, had budget. User experience was the #1 thing, and getting on a bunch of platforms and constantly going through that. Then, each one of those took six months to a year to close. You had to be really careful what came in the funnel. We threw away way more leads than we chased after. I think that was a big part of our success. If we had chased all leads, we would have done a thinner effort on all of them and probably not closed many deals. Looking at #1, one of my questions would always be: we’re kicking off one of our customers, so show me. No one’s heard of it, but it was the Netflix killer in Canada, which didn’t do well, but they had hundreds of things to do. They had to buy content, get servers, etc. I said, “Out of all the things that you have to do, where’s the end experience?” If it wasn’t in the top three, we’d stop talking to them. That was a tough lesson to learn because that’s what we were bringing. We were going to bring great user experience on a lot of platforms. I’ve done it, and I’ve seen other startups that chase these leads, and it’s not a great fit. You may even close them, but wow. It’s really bad for your business. There are some accounts that we closed that were off, and we did the mistake, and they closed, and they were probably as much damaging as the big ones that were wins. You have to be very careful with those. You can only afford to make one or two of those mistakes.

Alejandro: As we’re talking about here, breakthroughs that lead to becoming successful, definitely customer focus was one. But the other one was, without a doubt, finding your Why. In this case, it took more than what you had hoped. We’re talking about at least a year, so why do you think it took so long, and what triggered for you guys to find your answer?

Jason Flick: Because I had done a bunch of startups before that were just focusing on: what does the customer want? What is the focus? What are the features? Then you look at others that don’t have them all, but people are buying it for a reason. A really simple example is Starbucks. When you buy a Starbucks coffee, it says, “If you buy a certain premium card, it says something about you.” So, understanding that was key, and that came back to who we are going to be. We spent a fair amount of time. We said, “We have this engine that can do almost anything. It can solve problems in this market, but which ones, and why are we doing this?” We felt that our technology could change people’s relationships with technology. A lot of people are frustrated with technology and how it works. We said: we want to be the answer to that. We want to be the tool that solves that problem. We’re not just going to be the one that can do it faster or cheaper or quicker. We had that as our core value. That drove things like letting us build an art team. We were a whole bunch of geeks, and we were able to build an art team because they saw what our Why was and want to be part of that. We speak different languages. You get an artist who knows how to use Adobe tools, and you get a developer who knows how to build servers and trying to work together. Wow. Because of that Why – it took us about a year to figure that out, as you said, and we spent a fair bit of time just dedicating a day here and there to plan it out, think about it. I think our initial one came up, and we’ve kept with it at UI all along, but it was like: make technology fun and easy to use. We interpret that differently now, but that was what we came up with almost 11 years ago. That really drove us. That was our goal. Even though every day you’re doing all kinds of specific technical things, adding features, that’s what drove it, and our clients knew that, and they were on the journey with us for that bigger Why. So they were, “Okay, so you don’t have this feature. Great. But I know you’re aligned with what I want to do.” That was a big part for us. Like any startup, there was a roller coaster ride, so having that bigger thing than yourself or your market or your company as a goal really helped.

Read More: Nick Desai On Raising $165 Million To Bring Doctors To Your Home

Alejandro: What did blending art with science look like with the UI team?

Jason Flick: The end result was, we weren’t going into clients because initially, we’d go in and say, “Here are three balls bouncing in JavaScript.” And it would be bouncing at this speed. Then, we’d say, “Look at these balls bouncing in ours.” And they were ten times faster. Imagine what you could do with ten times the performance” because we went right to the metal. What it looked like was, we would go into these meetings because we would be very selective about going after certain clients, and we would actually get our team to design from the ground up what we thought they wanted. We’d go to a meeting, and we’d go, “Boom. Is this what you’re looking for?” It wouldn’t be all integrated and completed, but it would look like and feel like what it could actually be, and that’s a gamechanger. Most customers aren’t like entrepreneurs like us and your listeners who can see the world differently and have vision. They don’t. If you can’t show them exactly what they’re talking about, and they can’t touch it, it’s really hard to close a deal. I’d say we were able to shave months and months off deal cycles by having that team there. Then, of course, they could also execute on it. That was great, as well. Then, also, they helped our product team because we used them internally. It was a cross-functional team. They were used by marketing, they were used by our clients, and we used them as our product team. Without that, I think we would never have been able to be that premium solution for these apps now with some of the biggest brands in the market. The biggest media brands in the world are using our tech.

Alejandro: How did you capitalize the business?

Jason Flick: That’s probably a book, and I have no time or interest in writing one, but I think we used every type of capital. Maybe somebody can comment if I miss one, but aside from the early days using credit cards and stuff, we used venture debt. Along the way, we used private equity, which was our first form of capital. We used subordinate debt, which is an interesting mixture. I’m sure people here know that, but entrepreneurs wanting to look into that if you’ve got a cash flow. We use bridge financing. We use convertibles. Our C Round, which was two years ago, that was our only real VC. Prior to that was either private equity or strategic. We had Sky/Comcast and what is now Warner Media and AT&T as investors. So, it was a very diverse board and a lot of complexities around that, and being based in Canada, there are certain times in Canada when you just can’t raise funding. It just turns off, where I think in other cities, it goes up and down. I think in 2000, we had something like 1.2 billion in venture capital, and then eight years later, the venture capital amount of money in Ottawa was $50 million.

Alejandro: Wow.

Jason Flick: And most of that was to go with a living debt. Yes, wow. You have to have this way where you can be flexible, and so we had to. One advantage in Canada is the government support. They’ve been really supportive of us – the program is called IRAP and SR&ED. We had to be an omnivore, I guess, for capital and be very flexible. I would challenge someone to find the type of capital that we didn’t use that’s available. I think that had a lot of creativity and took time. But if you run out of capital, you’re out. I always had a Plan A, Plan B, and a Plan C. Sometimes, we did have to go to that Plan C option.

Alejandro: I hear you. And part of really understanding what your plans are is surrounding yourself by the right people and getting the right type of guidance. I know that for you, peer mentoring has made a big impact, and you really stand behind it. Why don’t you tell us how peer mentoring has helped you, and how do you think people listening and watching can benefit from including that as part of their own journey?

Jason Flick: The old expression, it is lonely at the top, is for sure, everybody is coming to your office because they want a raise, or a promotion, or a new thing, or to go left, or to go right. Then who do you have to share that with? Maybe your wife. Maybe some friends. How many CEOs have CEO friends where they can sit down and say, “Look at this merger and acquisition. What do you think of this offer?” You just don’t have that. I think it’s probably getting close to 18 or 19 years that I’ve been in a peer mentorship group. Some are informal, and some formal. There are lots of organizations that do it. I think it’s critical because you need to learn from their lessons. It’s even just nice to sit around a table and hear someone else is having a worse day than you, and here’s how they’re solving it. I would say that I have avoided a lot of scars by having this round table of 14, 15 CEOs. Over time, I changed groups. When we were 50 people, those are the problems you have there, but when you’re 300-400 people, and you’re in the tens of millions of revenues, your problems do change. So, you might want to look at that group over time, but every professional athlete, every skier, they all have coaches. Even amateurs have coaches. CEOs – look at the impact that CEOs have across the world and the globe. It’s huge, and yet, most don’t have some sort of mentor. They’ll hire a contractor consultant for that ability, and they’ll call bull s*** on you. They don’t have a vested interest. None of them have shares in your company, so when they give you advice, it’s not because they want to raise a promotion or more shares. It’s really rare that you can get that advice. I highly recommend to make your own or join one. There are lots of organizations. I would say as a geek developer who had to move into the subtleties of managing culture, companies, funding, and be multinational selling in dozens of countries, the advice from the right person at the right time in that group is critical.

Alejandro: You were talking about culture. I know that culture has been a really big component and something that especially with You.i TV, you have taken very seriously. How did you guys think about culture with You.i TV, and what have been some of your key learnings during this journey?

Jason Flick: Early on, it’s organic. There are 10 or 15 of you, and we started with two of us. So, it’s organic, but as you grow, you add, and you have to be somewhat thoughtful about it. For me, I involved my wife a fair bit to help, to add that aspect to it. You’ve got to listen, but I think you also have to distill it down because when you’re very young, it’s like, “We have a culture that we like to race cars – because five electrics.” But sure, but then as you start getting larger and larger, you have to really distill it down and make sure that the right things are getting picked in there, but like a brand, they own it, not you. I think spending a lot of time thinking about that – we did a lot on profiling people so they understand introverts, extroverts, these are oriented, these are not, so they could understand who they are and where they want to go. So, putting a lot of the culture into what they want and who they want to be is key. If you take care of your people, then they’ll take care of the business. We had a lot of belief around that. But then, just having fun, but how do you have fun? When we were way back, we had Nerf war battles. That’s fun when you’re 10 or 15, but what’s fun when you’re 200-300 people? Go and do citywide treasure hunts. Always putting a thought into that and knowing that investment will help with recruitment, and your staff will love it, and they’ll stick around. Even on exit, I think we had dozens of people that have been there five to ten years.

Alejandro: Wow. Talking about the exit, how big was the business when right before the acquisition happened? Is there anything that you can share in terms of employees or anything else?

Jason Flick: Depending on who is contracting and what’s going on, 250, 350 people was kind of where we were. One year we hired 100 people, but the last two years have been focusing on partnerships. We had announced a bunch of partnerships with Microsoft’s Eric and Spinout for media that they had announced. They were going to use our tech everywhere, so it was about getting that tool in their hands. The first few years were us doing it. Then it was giving it to our clients, and then it was eventually going through partners. A lot of work went around that; that wasn’t headcount-related. Certainly, in the tens of millions of dollars of revenue, and the big focus was getting it to recurring. We went from four years ago, where we were 5% to 10% recurring, and we were getting up over 50% recurring, which was the goal. Our 40% of revenue was from customers outside North America. So, validating that for that to be done. It was either exit or D Round. D Round would have been going on to IPO, and obviously, the exit was the choice we made. Yeah, that was an interesting one.

Alejandro: You mentioned doing either a Series D or doing the exit. Why did you choose the exit and do the acquisition? What was that process like and how did you guys end up getting to the finish line, and what did that look like?

Jason Flick: Again, you always want to have a Plan A, B, and C. You can’t put that much work down on one option. Conditions created that the exit was the right one. If you look at who was on the board, and they were pretty clear acquirers about HBO. Obviously, Netflix proved that technology was key, and content was a commodity. Some say, “Netflix is a technology company.” We now know that it’s a content company. Now, all the content companies need to be technology. I think it was going to be a key asset for them, as they said, so that made a lot of sense, and they really wanted to keep that as a differentiator. It wasn’t a great time to be out raising a D Round. I think there are a bunch of lessons learned for me about what is the key KPI that you put forward to investors? We had always grown revenue, and I think we had seven to eight years in a row doubling revenue. That revenue was always our metric. But we were at that inflection point where it was about developers. We went from a handful of developers three years ago using our tech to hundreds of developers. That probably was the KPI we should have raised the D Round on. We continue to raise it on funding, which when you do partnerships, it’s a shared risk of future revenue. When you get developers engaged, you take business away from yourself to engage that community. I think there are lots of lessons learned for me on what that was. I always learned a small lesson about naming of rounds. Who would have thought it mattered, but we raised our A Round from Kayne, which was private equity firm because we were profitable. We were bootstrapping the business back then. Then, six months later, Warner Media came in – it was Turner then, and we raised our next capital, so we dispensed with a trough of the A, but, of course, they wanted to call it a B. You don’t want to be the ones leading A.5, but it really was our A. We actually ended up early on getting off-kilter on our letters. So, our B was our A.5, our C was our B, our D should have been our C. There are all these metrics and expectations that come with the letter.

Alejandro: Oh, yes.

Jason Flick: So, I’d go back and try and fight a bit more to say, “Politically, guys, this is not our B Round. We’re actually dispensing with half of what we said our A Round was, so it’s actually a fact it’s not our full B. So, that was an interesting one. On our D Round, you’d expect a little bit more consistency and stuff with our C. That was a tough lesson learned, and we had to live with that through each round of funding.

Alejandro: Got it. Let’s talk about the acquisition. What was that like because there are a lot of people now watching and listening that they are really focused on raising capital? Perhaps they don’t know that when you raise money, and you’re taking money in, it comes with expectations, and the expectations are returns, which is taking it to the finish line. So, obviously, the acquisition is the Holy Grail. That’s where you were able to take You.i TV to, so what did that look like? What was that process or that journey?

Jason Flick: Yeah, and probably a little bit unique for us in the fact that we had AT&T and Comcast as investors, and we’re a strategic platform for them. Everyone looks at them as obvious acquirers, but you certainly want as many at the table as you can get. For us, going through growing the business while having these conversations and trying to balance those was a very tricky point. And, of course, they were a significant part of our revenue, as well, so it’s like, what games could you play, or do you play, or do you just get everything going? But I think, in the end, it went fairly quickly, considering it was an AT&T division, and it just made sense. Again, going back to one of our core values, which was to get every piece of glass, so UIs, tagline, was always own the glass for the biggest brands in the world, and this was going to expedite that. HBO, obviously, I’m not saying anything that isn’t public, wants to get everywhere, and that’s what our tech does. I think even though I would have loved to continue to go on, there is competing technology finally for what we’re doing at Google Flutter Technology, but we were the leader in that space. But we also wanted to get every piece of glass, and I think that was a way we can see the staff. “This is what our dream is. Any screen you’re going to turn on is going to have our engine on it, and that certainly is expediting that,” so I think that was aligned with what we started the business to do. It aligned, as an exit, that made sense for all of our investors. And we had diversity, as I mentioned, in those investors with diverse expectations, so it achieved all those. In the end, everybody got what we needed to do at the time that we needed to do it. It’s tricky. No everybody wants to do it, and not the way they want it done, and a good deal means nobody’s happy. Right?

Alejandro: Yeah.

Jason Flick: –all these things that you learn when your deal. In a peer mentoring group, across the groups I’ve mentored, probably 30 to 40 businesses were sold, so I got to hear all these different stories. You go in with awareness, and then yeah, you make it happen.

Alejandro: In this case, it was reported over $100 million, so pretty good for someone that was born in a small town in Canada.

Jason Flick: Yeah, and it converts. You add 30% on top of that just because of the Canadian dollar.

Alejandro: Oh, yeah. In that case, was that day like when, all of a sudden, you see this contract with all these zeros in there? What was that like for you? Make us be insiders.

Jason Flick: Yeah. It’s interesting. Especially if you’re on the inside, you see it coming slower. You see the stages. Unfortunately, it’s a little anticlimactic. It’s not like winning a lottery ticket, but unlike winning a lottery ticket, usually, you know you earned it, and you got it. Yeah. It’s like, what does the next phase look like? I’m now in a stage where I can do what I want. I think that’s the interesting one. Prior to that, even though maybe I had the wealth to say, “I’ve made enough money. I don’t have to stay working at UI. Personally, regardless, you’d never give up your baby. This is the first time I don’t have a baby, and I can do what I want. That’s an interesting stage to be at, and it’s the next stage I’ve got to work through personally. What do you want to do? Before, it was like you have this business, you have this in front of you to be able to truly choose what you want, all excuses gone, it would be interesting – the exit side. My main advice is, how are the people around you? If you don’t have the right lawyers and the right support and people that know how to sell a business, like yourself, then it’s critical because there are a million moving parts, there are hundreds of pages of documents. Certain things matter, and certain things don’t. Knowing of the 200 things that just came back in red line, what are the two that need my attention and negotiation. Those are really key, so I think that was a big piece for us, which is, I had people that I trusted around me, and again, also, because of the peer mentoring, I was able to get, “Who have you had success with?” Boom. “These people.”

Alejandro: Yeah. Absolutely. One of the questions that I typically ask the guests that come on the show is, imagine if I put you in a time machine and we’re able to go back in time, and we have that younger Jason that is coming out of these jobs and thinking about starting something – right before N-able, your first business. Imagine that you have the opportunity to have a chat with your younger Jason. What would be that one piece of business advice that you would give to your younger self before launching a business, and why, given what you know now?

Jason Flick: I would bring that art and science lesson earlier in my career. I think selling commodity tech that is just a little better, one of 50 people that can do it – differentiate, be a brand, go premium. I would say I would have pushed that sooner in my career. Some people are good at doing it and grinding and doing the next Walmart. Wow. Not at all a venturist. I think, early days, as a geek programmer, I was way too focused on that, telling myself to mix those together and focus on making everything beautiful and technically accurate sooner. We’re in the experience era right now. We have been for 10-20 years. I would have liked to have been on the leading edge of it. Now, it’s a commodity. Even on Kickstarter, you get a thing, and the box is beautiful. They know every edge has to be rounded and perfect. So, we’re in that era. I would have liked to have been in that era a little sooner and skip some of the grind of really low-day rates and trying to deliver on something that you wanted to, but the budget wasn’t there because you had gone down the market too far.

Alejandro: I hear you. Jason, for the people that are listening, what is the best way for them to reach out and say hi?

Jason Flick: Reach out to me on LinkedIn. I think I’ve still got my access set to open. I’m always happy to talk to fellow-entrepreneurs. I find as much as I can share the experience in my 20 years in startups, I find I always learn something from them as well.

Alejandro: Amazing. Jason, thank you so much for being on the DealMakers show today.

Jason Flick: Alejandro, my pleasure.

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