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01 · The guest
Benjie Cherniak
Founder & Principal, Avenue H Capital
Benjie Cherniak is the founder and principal of Avenue H Capital, which invests in and advises sports betting and iGaming businesses. Since May 2024 he has been an independent director on the board of Kambi Group plc, where he chairs the Remuneration Committee. Montreal-born and based largely in Las Vegas, he spent 14 years at Don Best Sports, the odds data business behind the screen US sportsbooks relied on, rising to Principal.
At Don Best he automated the odds screen into data feeds and built one of the first US in-play trading floors. He sold the business to Scientific Games in 2018 and stayed two years through the SG Digital integration. He is a regular on NEXT.io’s Vested Interest podcast with Pierre Lindh and Lloyd Danzig.
Connect with Benjie on LinkedIn →02 · In this episode
Moments worth queuing up
In their own words
“The right time to sell your company is when you sell your company.”
“A decision that we could get done in one day within the independent Don Best ecosystem might take three months within the big public multi-billion dollar market cap company.”
“To be honest, it wasn’t very strategic or well thought out, and we’re now six or seven years later, and it’s still kind of what I’m doing.”
“There are founders I’ve worked with where, when the going gets tough, they don’t get going. That’s the opposite of what I’m looking for.”
“There’s nothing wrong with a founder who’s got some leverage interviewing the investor the way the investor’s interviewing them.”
“You want to build the discipline of creating structure when you don’t need to.”
Key takeaways
What to take back to your desk
In-play started with one client and a catastrophe. Year one of the NBA in-play product had weak models and UNLV students as traders. By the end of the year the client was making money, and the product rolled out from there.
Good ideas can fail on timing. Don Best TV launched careers, but the unit economics weren’t there, so it was shelved. VSiN later made the model work and sold to DraftKings. Let an idea evolve without burning too much capital.
There is no perfect time to sell. Benjie was outvoted two to one by his partners. Waiting a year or two might have meant a bigger sum, but holding on longer meant COVID. The right time to sell is when you sell.
Price is not the only term of a deal. Weigh what the buyer’s ecosystem means for you and your people: decision speed, reporting lines, how long you stay on. Inside a public company, a one-day decision can take three months.
Due diligence runs both ways. Benjie now leans towards second-time founders he can reference-check. Founders with leverage should interview investors as hard as they are interviewed, and build a cap table that rows in one direction.
A CEO answers to the board and the shareholders, while leading employees from the front. Build structure before you need it, rather than retrofitting it after the fact.
Full transcript
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Benjie: I don't think I've ever said this publicly, but I'll say it to you now. My two partners wanted to do the deal. Quite frankly, I don't think that I did initially. If it was entirely and 100% my decision, I don't think we would've sold the company at that time. But I was outvoted, right? Had we waited a year or two years, as you see where M&A went, we would've gotten a much tidier sum for our asset. The value would've been enhanced had we hung onto it. A decision that we could get done in one day within the independent Don Best ecosystem, within the big public multi-billion dollar market cap company, might take three months.
Leo: If you could go back to that time before you did the actual deal, what's something that you would advise your younger self?
Benjie: To enjoy the moment and to enjoy the process, and to just appreciate that period of time and not take it for granted.
Leo: Welcome to The iGaming Leader Podcast. I'm your host, Leo Judkins, founder of the iGaming Leader Mastermind, and on this show I sit down with some of the most inspirational leaders in our industry, diving into real challenges, high-stakes decisions and lessons that shape our industry. If you're a VP, director or C-level executive in iGaming, this podcast is built for you. Before we dive in, a quick thank you to our sponsors, Sumsub and Bloomreach. Sumsub is the full-cycle verification platform trusted by top iGaming operators worldwide. Sumsub helps operators onboard players quickly, stay compliant and prevent fraud, all without slowing growth. And Bloomreach is the AI platform for marketing automation used by leading iGaming operators, turning player data into real-time engagement that strengthens retention and loyalty. More information on both in the show notes and in the description. Let's dive in.
Leo: Hey, everybody. Welcome to the iGaming Leader Podcast. My guest today sold his company without bankers, without a process, and says that if he'd waited a year, he'd have got double or triple the price. He ran Don Best, the odds screen that half the industry grew up staring at, and took it through its sale to SG. Since then, he's been investing through Avenue H Capital and sits on the board of Kambi. Today we're going from odds screens to trading floors, the exit, the investments that worked, and of course the ones that didn't, and who a CEO really answers to. Benjie, welcome to the podcast. Super excited to have you here, man.
Benjie: Leo, that was quite the intro. I love it. Let's jump into it.
Leo: All right, cool. Obviously I want to start with Don Best, if that's okay. It was a 20-year-old odds screen when you came in. At some point you decided to turn that into a live floor for American sports, when nobody in the US was really pricing in-play. What did that moment look like for you, and what were the people around you telling you?
Benjie: Well, I think you've got to remember the era that we're dealing with. You go back to 2007, 2008, in-play betting didn't really exist in the US. And the Don Best screen at that point, going back to 2005, 2006, 2007, the company was just the Don Best screen, which was kind of the original Bloomberg terminal for US sports betting. The genesis of all this is that I began going to the ICE conferences and meeting with all of these sportsbooks out in Europe, and I realised that they had not just one subscription to the Don Best screen, but five, ten, fifteen, twenty subscriptions. It became evident that they had multiple traders eyeing the screen on a very manual basis. So the first thing we did was take all of that third-party data and automate it into XML feeds, which sounds very, very basic today because it is. But if you go back to 2007, it really wasn't all that basic. That allowed all of our global partners to automate a pre-match betting system for American sports, which they didn't have.
Benjie: At that point, all of our customers kind of came to us and said, "Benjie, our US pre-match product is fantastic, but what we really need now is US sports in-play. Can you provide that to us?" And the reality is that nobody was really doing it. It was big for soccer, and it was big for tennis. But here in the US, there was no in-play for basketball and hockey and baseball and football. There was halftime betting. So we endeavoured to do that ourselves and went out and built the trading floor. What the moment looked like is, we had customers asking for it, and it became the natural progression for us.
Benjie: In my mind, we were really the first ones to go out there and create an in-play betting product for, initially, the NBA. I think that was maybe 2009 or 2010. It began with one customer, in one jurisdiction out in Europe. We hired a guy named Craig Mucklow, who remains a friend of mine, and moved him and his family from Europe to the US, and he began building out our trading floor, if you want to call it that. We had another gentleman who built out all of our models and algorithms, and we had four kids from UNLV who came on board as our traders, and that was the in-play trading team. We built out the NBA product, and it was a disaster in year one. A complete catastrophe. The models weren't strong. The traders themselves went to school at UNLV and would show up hungover on football Sundays and whatever else. But we got through the first year, and by the end of the year our client began actually making money, and then it kind of rolled over from there, and we began building out more clients and more products. The genesis is that we saw the void in the market, and we saw that our customers globally would be interested in a product like that for American sports.
Leo: Just listening to you, you look back on that with a lot of nostalgia, right? Is that still how it feels when you think back to those days of getting all these new kids on the products?
Benjie: It just means that we're ageing a little bit, I guess. But there's definitely a bit of nostalgia when we think back to that era. I was in the thick of it then. We were running a company and travelling the world and trying to build out clientele and building out a trading floor and managing our team and managing the injury reports, and just doing everything that running a company such as Don Best entailed. We took a lot of pride in our work, and there was certainly a camaraderie back then. Do I miss it? I definitely miss parts of it, for sure. I think I miss all of it, if I'm being honest. But you can't turn back the clock. That was then, and this is now.
Leo: It's funny how, as we age, we keep looking back trying to find those moments again, and they're obviously gone, because it was the first time and it was all new. When you think back to that time, what's your proudest moment? The one that still stands out?
Benjie: You and I were talking a little bit before we came on air about this being a relationship business, and I think it is that. It's the relationships and the camaraderie and the team building, and working alongside people that you got to know and spend a lot of time with and that you cared for. Not just the people who worked with me and alongside me, and not just my business partners at Don Best, who were less visible than I was, but our clients, the people I spent a lot of time visiting and going to dinners with, that whole aspect of it. And the pride of doing your own thing and building something, and feeling like you're building something that matters. When I look back at it, the nostalgia in me, those are the things that I miss.
Leo: I love it. When we were speaking a few weeks ago, you said that a great entrepreneur refuses to fail, but a great entrepreneur in the wrong box fails anyway. I always think about this with founders. When you think back on your best years, how did you tell the difference between the stubbornness any entrepreneur needs, being more stubborn when everybody else tells you you're wrong, and foresight?
Benjie: It's an interesting dynamic. You look at today's great entrepreneurs, and that refusal to fail and that steadfast belief that what they're doing is going to work allows them to find a way to make it work. But at the same time, you have to have flexibility within that dynamic. There were things we tried in the Don Best days that failed, and I don't think they failed because they were bad ideas. Maybe we were too far ahead of our time. One of the things we spent a lot of time on, around the same time we began building out our in-play division, was something called Don Best TV, where we began doing all sorts of video clips and short-form video. The videos were great, and we actually started the careers of some people who became reasonably well-known personalities. Kelly in Vegas got her start with Don Best TV. A guy by the name of Todd Fuhrman, who went on to do stuff with Fox and his own podcast and has had a great career, got his start on Don Best TV. And we had a guy named Kenny White, who was fantastic. We had some really good people and good personalities, and we invested a fair bit of money into it. For whatever reason, it just didn't resonate in that era. Certainly, that type of short-form and longer-form video found a home with companies like VSiN, who had a really nice exit to DraftKings. Maybe had we stuck with it, it could have been something more interesting. But at the time we were bouncing a few different balls, and the in-play trading was really beginning to resonate. As much as we believed in Don Best TV and wanted to make it work, the unit economics just weren't there at that point in our life cycle as a company, and we had to shelve it.
Leo: Timing's such a big thing, isn't it? You can have the best idea, but timing...
Benjie: I think had we stuck with it, and found a way to make it work within our ecosystem without burning too much capital, it would've found its place and created value for us. And I think for a lot of today's entrepreneurs, it's the same thing. You have an idea, you start your company, and you have to have the flexibility to allow that idea to evolve to what's going to lead to the best outcome for you and your investors, and what's going to find the sweet spot. You see it with great entrepreneurs. They ebb and they flow, and they figure out the path. They know where they're going, they're not exactly sure how they're going to get there, and they have to have some flexibility.
Leo: That last piece I always find so crucial. I love that you said that. You know where you're going, and you figure out the path as you go. You sold to SG in 2018. No bankers, no process. When we spoke a few weeks ago, you said that if you'd waited a year, you might have got double or even triple the price. Take me back inside that decision, if you will. What did you know? What did you not know? And who did you actually trust to talk this stuff through with?
Benjie: There's a couple of things here. There was always inbound interest in the Don Best asset. We danced with a couple of companies over the years, and fortunately none of those conversations led to M&A. I say fortunately because the numbers we were discussing then were lower than where we ended up when SG, now Light & Wonder, approached us. At that time, it kind of felt right from a timing perspective. But I have to be honest with you. I had two business partners at the time who were far less visible, but we worked very closely together: a guy by the name of Chris Cape and a guy by the name of Robbie Maness. We got along famously throughout our tenure at Don Best, and I can't think of any major disagreements we ever had about how to go about building the company. I was day to day, they were more in the background, and as the quarterback day to day, anything I suggested would generally get done.
Benjie: But if we disagreed on something, it was two out of three, and that's just how it worked. When it came time to consider the deal we did with SG, I don't think I've ever said this publicly, but I'll say it to you now. My two partners wanted to do the deal. Quite frankly, I don't think that I did initially. My vote was that we stay with it. Why? I loved running the company. I enjoyed it. I knew that the PASPA repeal was around the corner, we were in the midst of that whole regime, and I felt there was a lot of upside and value to be had from that. And financially, I was in no hurry to get to an exit at that point in my life. By the end of the process, once we went down the road, I was excited to sell the company. But at the beginning, when they approached us, if it was entirely and 100% my decision, I don't think we would've sold the company at that time. I think we would've just continued to play ball and figure it out as we went along, the way I suggest some entrepreneurs figure things out as they go. But I was outvoted. And once I was all in on selling, I was all in on it, and it turned out to be a great outcome, and I'm happy with it.
Benjie: I'm glad that we did what we did. But looking past that, I'm of the belief in retrospect that had we waited a year or two years, as you see where M&A went, we would've gotten a much tidier sum for our asset. The value would've been enhanced had we hung onto it. That being said, had we hung onto it beyond that, we would've got into COVID, and I don't know how we would've survived COVID. We probably would've figured something out, but there are a lot of unknowns in that. So the right time to sell your company is when you sell your company. You can always play the game looking back: should I have waited longer? There's no way to know what the future holds. I don't have any regrets about it, but I'll admit that had we waited a year or two, we would've gotten a much bigger sum. It is what it is.
Leo: Benjie, you were talking about M&A with or without a banker. Tell me a little more about that for today's entrepreneur. What are some of the pros and cons? What should people be considering about how they actually want to execute it?
Benjie: As I alluded to in our journey, we weren't proactively selling the company or looking to sell it. It was inbound, and when the inbound made sense, we got into it. In retrospect, would it have made sense to be more proactive and run a process? Arguably. For today's entrepreneur, it depends a lot on their situation. If you're building a company and you feel the time is right to go to market, you have to make a decision. Do you want to go at it on your own, with your internal people or some friendly advisors? Or do you want to bring in the bankers, run a process, and let them go out there? This is what they do for a living. They can find the potential buyers, potentially create a competitive situation, and represent your interests along the way. And of course they're going to be paid well for that, as they should be. They can guide you, and they've built relationships with the companies they're going to help sell your company to. So I don't think there's a right or wrong.
Benjie: Things to keep in mind, for sure: if you're working with a banker, you need to be specific about who you want to work with. The right way to go about that is to interview those folks. Get a feel for whether they think you're the right fit, what an M&A process with them would look like, and what they feel the value of your company is. Having those conversations with bankers will help you get a feel for what might be realistic or not in this process. There's a certain salesmanship in how they approach it, as there always is when you're selling a service, but there's also going to be an authenticity to it. You've got to find the banker that you feel will be the best fit for you and deliver the best outcome. Or you go at it alone. And going at it alone doesn't mean you're on an island. It could be based on a relationship you have with a certain vendor or client, or with a B2C company that likes your asset, and you just begin having natural conversations and see where they lead. Or you work with your network to put the word out on a confidential basis and begin having conversations that way. If you get down the line into a meaningful conversation, you're probably going to need to hire some lawyers to help with the ins and outs. It'll be a lot cheaper than a banker. There's no right or wrong to this, but I think both are viable options.
Leo: That must be such a difficult part of it, that there are no clear answers. Just like the entire entrepreneurial journey, they're all judgement calls, based on the best information you have and what you get from around you. So how do you decide?
Benjie: I've seen really successful outcomes going both routes. I've seen companies have successful outcomes working with bankers, and I've worked alongside companies that have done it without. Generally speaking, the bigger you get, the more likely you are to work with a banker, whereas the smaller you are, the more realistic it becomes to be opportunistic. But looking at companies I've been intimately involved in over the last five or six years that have had M&A outcomes, I've seen both, and it works well in both scenarios. It's just a question of what's the right fit for you as a founder.
Leo: I was talking to somebody from a boutique M&A firm the other day, and he was saying, "It's a good deal when both sides actually feel a little bit screwed." I don't know if that's true or not, but I love what you're saying: the deal's done, you can't change the past anyway. How did you feel after that period, going from actually running it to an earn-out? What did that look and feel like for you?
Benjie: Here's the first thing. When you sell a company for a reasonable sum of capital, for me it was a life-changing financial outcome, and it's a great feeling. It was announced, I think, on the first day of G2E, 2017 or 2018, I'd have to look back. But when it was announced, there's a certain pride to that. It's a great result, and you're the big man on campus for that day. Everyone's asking questions and wants to talk to you. And financially, it's just great to see that money hit the bank. I've since had the opportunity to sit alongside some entrepreneurs when their life-changing moment comes and the money hits their bank accounts, and there's a gratification in assisting them on that journey as well.
Benjie: But then you've got to deal with the reality that you no longer own the asset, and you're within somebody else's ecosystem. I was eyes wide open on that. Don't forget, we were coming into the Scientific Games ecosystem. Maybe eight months earlier they had acquired Matt Davies' company, primarily for the OpenBet asset, and they were still going through the growing pains of integrating OpenBet, both operationally and administratively. Then they do the Don Best acquisition and stack it on top. OpenBet was the crown jewel, and Don Best was the pricing that would be powered within the crown jewel. So we were certainly a lower priority, as we should have been. But the whole thing led to some challenges, administratively and operationally. I had to accept my role reporting into certain people within OpenBet, and they were all good people with the best of intentions. But I also had to manage my team and keep people happy. They were used to working for me, in an environment where decisions would sometimes get made within fifteen minutes. A decision that we could get done in one day within the independent Don Best ecosystem might take three months within the big public multi-billion dollar market cap company. That was a reality I was eyes wide open on, but it was a huge challenge to keep my staff on side, keep them motivated, and keep them from walking while they adjusted to this new reality alongside me.
Leo: And for yourself, that must have been difficult as well. Coming from an entrepreneurial spirit, suddenly it's an approval process. It's not your final decision anymore.
Benjie: This isn't unique to me. This happens for everyone that gets acquired. Some acquisitions are a lot smoother than others, and I wouldn't say ours wasn't smooth, but there were certainly some significant challenges. There always are. When you're an entrepreneur and the time comes to consider M&A, if you're running a process and looking at multiple options, you've got to consider the financial piece, which is probably the most important for most entrepreneurs. But it shouldn't be the only factor. You should also consider what it will mean for you and your employees in the short, mid and long term within that company's ecosystem. How good a fit will it be? What are your objectives in terms of staying on? Is it a six-month handover? A year? Two years? Multiple years? These are all things you've got to consider alongside the financial piece, if you have the privilege of multiple suitors talking to you about your asset.
Leo: On a sidetrack there, Benjie: do you feel founders spend enough time on that part of the decision? Or do they hang too much on the carrot of the exit and the potential earn-out, and not consider enough what it's like to now work for someone, and to have their baby transformed into something they don't control?
Benjie: Leo, look. You start a company. You come up with an idea, you get the thing going, and then you've got to bootstrap it. At some point you've got to figure out how to bring in capital from guys like me, who give you a hard time and don't want to write cheques into every company. Then you've got to deal with the VCs at some point, and they bring a whole other ball of wax. Then you've got to get through the day-to-day of building your B2C business and acquiring customers, or on the B2B side, finding a value chain within the iGaming ecosystem. Then you've got to find clients, sell to them, travel to conferences, shake hands and kiss babies and go to dinners. It's all fun, and it's what you've signed up for, but it's a lot of work to get to the point where you've got revenue. Then finally you get to some profitability. And somewhere along the line, you build a company that's attractive enough that somebody, or multiple suitors, are interested in acquiring it.
Benjie: It's a hell of a battle to get there. So top of mind isn't necessarily what it will feel like day to day within that new ecosystem. Top of mind might be, "Holy shit, I've been doing this this long, now I've got an exit opportunity, and I can make life-changing money." And that should be the priority. Naturally, until you get to that point, considering what life would be like post-sale shouldn't be that much of a factor. You're not there yet. You're building. Then when you get there and it feels right and you start looking at it, that's when you start thinking about it. Should it be thought about more? Probably. But there are bigger fish to fry from day one of entrepreneurship to selling the company than how you're going to figure out life after the sale. It's a huge fish to fry, but there are bigger ones along the way.
Leo: How was that for you, then, Benjie? For some people it's an existential gap. My purpose has gone. The thing I spent so much blood, sweat and tears on is gone. Or it's a chance to refine your purpose. How did that transform for you after the exit?
Benjie: That's a great question, and it's a great question to ask me, because if I give you the honest answer, I don't know that I have. When I sold the company, I stayed on for a couple of years for the earn-out and my commitments to both my employees and my new employer, and I wanted to live up to that to the maximum I could, and I feel like I did. Then it was time to move on, and now I'm a free agent. What do I want to do? What I really wanted to do was go down to Miami for a bit, chill on the beach, and not think about business as much, and that's kind of what I did. But then the phone begins to ring. "Hey, can you help me with this?" "Do you want to look at that?" "Might you want to invest in this project?" "Do you want to join the board of this company?" Without actively thinking of a plan, I just began looking at some of these things, and that led me down the path of getting involved with startups, investing in some companies, advising some for equity, and taking on some consulting gigs.
Benjie: To be honest, it wasn't very strategic or well thought out, and we're now six or seven years later, and it's still kind of what I'm doing. What an exit looks like, and what you do post-exit, is different for every entrepreneur. Some are excited to jump back on the horse and start their next company, and I think that's fantastic. In my instance, I've just gone with the flow. I work hard, but I don't work as hard as I did when I was grinding in the Don Best days. And I don't know that I want to go back to that type of startup ecosystem, running a company and managing sixty employees or whatever it was. So I don't know that I have a good answer to that question, but that is my answer.
Leo: I love it, because it ties into what you were saying before. You go in a direction and figure it out as it comes along, and that's what happened in your case as well. You get a few calls and you go, "I kind of like this, don't like that, I'll do more of this," instead of frantically looking for the thing you're supposed to do. There is no supposed to. There's just whatever works and you enjoy.
Benjie: I think there are some individuals who, when they leave one phase of their career, proactively create the next phase based on a certain set of objectives. In my case, I don't think I've done that. It's not a discredit to myself. It's just being honest, and it's just the reality. I'm fine with it. I love the projects I'm involved in. It's been great financially, I think there are some great outcomes around the corner, I've worked with some great entrepreneurs and made some great friends, and overall I enjoy it. But I do wonder sometimes what would happen if I took a more proactive approach and searched for something specific. I don't even know what that would be. So I continue to go with the flow and assess projects as they come. There are no complaints. Life is good. That's where I'm at.
Leo: Do you think it's also that as we grow older, we go at a different pace? Obviously we see loads of entrepreneurs who are still in that intensity. I know for myself, as I get older, I've got kids. We were talking about how we could approach conferences differently. Do you think that's an element for you as well?
Benjie: Maybe. I also think that as you get older, you can work smarter and not harder, or both. The learnings of running a company, if you've done one or two exits or whatever number, you take those skill sets to the next project. And I think you can get a lot more done today with AI, with a lot less. Any way you slice it, if you're getting into entrepreneurship and building something, you've got to work your ass off. There are no ifs, ands or buts. Even in what I do today, it's not as though I don't work hard. I do. But I'm trying to protect my free time and protect the projects I'm involved in, and not get too scattered.
Leo: You've said publicly that it's all about the founder, and of course we hear that a lot. If you're happy to share it, when was the first time you figured out that it wasn't about the fancy slides, but about the founder?
Benjie: I think I've always known, and most of us know, that if you're investing or advising, the founder is super important. It doesn't take rocket science to know that. When I'm quoted saying it's all about the founder, I guess what I mean is: what's the number one thing when you're looking at a company? To me, it's the founder, or the founding team, and how they work together, how that founder approaches business and sees the world, how I mesh with that founder, and how I feel I can add value to them. You can't take a founder in a vacuum and grade them A plus, A minus, B plus, B minus. It's also how well you're the right fit for that particular founder and that particular project. But I'm of the belief that the right founder is going to figure out a path forward. And when I talk about the wrong founder, I don't want to throw any of the people I've worked with under the bus on a personal or name basis. I don't think that's right. But certainly there are founders I've worked with where, when the going gets tough, they don't get going. That's the opposite of what I'm looking for.
Benjie: I don't think I was anywhere near as stringent about founder excellence in 2020 or 2021 as I am now. They've got to tick almost all the boxes: their level of discipline, their level of enthusiasm, their professionalism, the way they communicate, and the way they intend to communicate with investors going forward, whether things are going well or not. I could point to a bunch of founders who do things the right way and are great at it. I don't want to point at the ones who aren't. But you get involved in enough companies, as I have, and there have been founders who were disappointing, in the sense that when the going got tough, the true mettle of who they are wasn't what it needed to be: the way they communicated, looking out for themselves as opposed to the stakeholders and shareholders. Those are things I'm very cognisant of when I look at projects now. And listen, you've got to have a few misses to get the hits. I'm not trying to belittle a founder who fails. You fail, you get back up, you ride the horse again. But there are ways in which you can fail versus ways in which you can succeed, and it's the integrity of the individual. Those are things I'm very, very disciplined in evaluating as I look at opportunities these days.
Leo: Failure is just part of the process, right?
Benjie: Absolutely.
Leo: When somebody's riding a wave, and maybe that's the first time you get into serious conversations with them, how do you do that due diligence? How do you figure out how somebody responds when the going gets tough, so that they don't turn on you?
Benjie: There's a couple of things. I'm much more apt today to invest in a second-time founder than a first-time founder, because with a second-time founder I can see the track record and how they dealt with things the first time around. I can reference-check it, speak to people who were involved in the other project, and really get a feel for what type of founder it is. Look, everyone who is a second-time founder was at some point a first-time founder, so it's a little unfair to make that statement. There are first-time founders out there right now building incredible companies, and there are seventeen-year-olds in their parents' garage right now who are going to build companies far beyond what you and I can envision. So I'm not knocking the first-time founder. But it's easier for me to evaluate the things you're alluding to with a second-time founder, who has been through the wringer, probably had some sort of outcome on the first exit, and understands the processes of building a business a bit better. It makes it easier for me to evaluate what type of experience it's going to be for me as someone supporting the journey.
Leo: This may be a bit of a leading question, but do you feel founders should do the same level of due diligence on the relationship with the investor? And if so, how?
Benjie: To the extent that they can, they absolutely should. How you choose your investors and advisors, and how you build your cap table, all have massive ramifications down the line as you build your company. You might be a founder who's been bootstrapping and it's just difficult to get the money, and at that point, if someone wants to get involved and the valuation is somewhat reasonable, I don't want to call it a beggars-can't-be-choosers situation, but it is what it is. But if you're a founder who has dotted the i's and crossed the t's all the way through, and you're in the fortunate position to pick and choose the people you want to align with, then you want to make those decisions very strategically. There's nothing wrong with a founder who's got some leverage interviewing the investor the way the investor's interviewing them, and making sure it's a two-way fit. It's very much a two-way street. And if there's a project I want to get involved in and the founder feels I'm not the right fit, that somebody else is a better fit, I don't belittle that at all. I think that's fantastic. The founder should make that call.
Benjie: If you're that founder, you really want to surround yourself with people who are going to be additive to your journey, who may disagree with you and challenge you on things, but in a way that's constructive. In the big picture, if you're in a rowboat, you're rowing with cohesion, all in the same direction. As opposed to having given up too much control to investors, or not having the right fit with the investors alongside you, so you're rowing one way and your investor's rowing the other. That's not a formula for success, or at least not for optimal success. And it's not fun either. You want to have fun with what you're doing, and it's more fun when everyone's having fun together.
Leo: Imagine turning up to meetings like that every time. Awful. Last bit. You said that CEOs in our industry don't talk enough about boards and board interactions. What are some of the things you see CEOs get wrong about that relationship, when it comes to obligations to shareholders and all of that? What are some of the dos and don'ts?
Benjie: As with building companies, there's no right or wrong when it comes to building your board and how you go about it. It also depends on whether you're a public or a private company. Kambi is obviously a public company, and as a board member of a public company, our obligation is to our shareholders. But I don't think it's that different for a private company. If you're on the board of a private company and there are investors, the obligation of the board should be to the shareholders and the investors. And for the CEO of a company, it's the same obligation. In most structures, you report to the board if you're a CEO. For some of these smaller startups, the CEO is usually on the board, so it's a bit of a different scenario. But for bigger companies that have grown and hired a CEO who reports into the board, it's an interesting dynamic. You report to the board, and therefore you're looking out for the interests of the board and those shareholders.
Benjie: But at the same time, you're running a company day to day, and you've got the interests of all the employees in the company. As a leader, you want to be in their corner. So there's a certain duality to it. You report to a board and look out for the interests of shareholders, public or private, and at the same time you want to be a soldier leading by example with your people. You want to run through the walls alongside them, be the first one running through, with your people running behind you. That requires a level of empathy, a level of relationship-building within the organisation, and a genuineness in how you look out for their best interests. It's an interesting dynamic, and not an easy tightrope to walk. The great CEOs out there are doing a fantastic job of it, and I have all the respect in the world for CEOs who can take on that role and make it work in the best interests of the organisation as a whole, the shareholders and the stakeholders, while building great careers for their employees.
Leo: It must be so complex. There are so many relationships to manage as a CEO. It's a big spiderweb, isn't it? The public, the board, employees. Difficult.
Benjie: I think it gets more complicated the bigger the company is. When you're a smaller company, it's a bit less complicated. But I think it's also a lesson for founders and CEOs: you want to build the discipline of creating structure when you don't need to. Build that structure when it's just you and your business partner and no employees. Start thinking in terms of where your company is going to be and how big you want it to get, and plan for that success at the beginning, as opposed to trying to retrofit structure and policies into your organisation after the fact. That's often the case, and it's not the end of the world. It can be done. But you want to start thinking about those things from the outset. I think that's part of excellence on the journey, for founders who are going to build companies that become pillars within our industry.
Leo: Love it. A comment about Kambi, by the way. I saw Werner in Marbella at the Power 50 and spoke to him there, and I saw him last week in Lisbon as well, and I'm always so impressed with how present he is. He's not on his phone, he's making notes. In a CEO position with so many things to manage, I find that super impressive, because most of us would be all over the place trying to manage everything at the same time.
Benjie: Werner's a rock star. From a Kambi perspective, we're very fortunate to have Werner as CEO, and beyond that, he's just a great, great guy. Nothing but great things to say about Werner.
Leo: Last question for you, Benjie. If you could go back to that time, the three of you before you did the actual deal, with the knowledge you have now and the role you're in now, what would you advise your younger self? To do differently, to do better, or maybe not to change?
Benjie: I don't know that there's all that much I would change in terms of the Don Best journey. To enjoy the moment and enjoy the process, I guess that might be a bit of it. To just appreciate that period of time and not take it for granted. Appreciate it for what it was, appreciate the journey. I think I did appreciate it back then, but looking back now, with the nostalgia and being a little bit older and wiser, or less wise perhaps, knowing how much I enjoyed that journey and how much meaning it has: as an entrepreneur, be able to sit back sometimes, recognise that you're in a moment in time, and appreciate what that moment means to you.
Leo: Benjie, fantastic episode. Thank you so much for your time.
Benjie: Leo, I've got to say I really enjoyed this. I enjoyed the conversation. I like the way you go about doing what you do and asking questions, and I think there are bright blue skies ahead for you and everything you're doing.
Leo: Thank you very much, man. Appreciate the chat. Speak to you soon.
Leo: Thank you for listening to the iGaming Leader Podcast. If you're a VP, a director, a founder or a C-level executive in iGaming and you're making the biggest decisions all alone, you might want to check out the iGaming Leader Mastermind, a programme I've built with small inner circles of vetted senior executives, where we run weekly hot seats and you get accountability from people who understand the effect of the decisions that you need to make. Find out more and apply at igamingleader.com. And a final thank you to our sponsors, Sumsub and Bloomreach. Sumsub is the full-cycle verification platform for iGaming operators, covering player onboarding, AML and fraud prevention, all in one place. Bloomreach helps operators turn real-time player insights into more personalised engagement that builds long-term loyalty. More at sumsub.com/gambling and bloomreach.com. See you next time.
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