Michael Serbinis On Working With Elon Musk, Taking On Amazon And Selling A Company For $3B

Michael Serbinis is the co-founder and CEO of League which is a digital health platform that connects people to a comprehensive network of health services and benefits. The company has raised over $70 million from Omers Ventures, BDC Venture Capital, Foundation Capital, Real Ventures, Telus Ventures, and RBC Venture Partners to name a few. Prior to this, Michael Serbinis founded DocSpace (acquired by Critical Path) and Kobo (acquired by Rakuten).

In this episode you will learn:

• How to make deals a win for all the parties
• The key drivers behind successful fundraising
• Critical factors around culture
• How to identify big markets
• Taking on large corporations with deep pockets

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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 Michael Serbinis:

• Wikipedia
• Linkedin
• Twitter
• Crunchbase

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FULL TRANSCRIPTION OF THE INTERVIEW: 

Alejandro: Alrighty. Hello everyone and welcome to the DealMakers show. Today we have a serial entrepreneur. Someone that has been around the block many, many times, and I think that we’re going to learn quite a bit. Different industries, different sectors that he has been involved, but let’s really go right into it. So without further ado, welcome to the show today, Mike Serbinis.

Michael Serbinis: Hey, thanks for having me.

Alejandro: So originally you were from where? Born and raised in Canada or where?

Michael Serbinis: I was born and raised in Canada, just outside of Toronto.

Alejandro: Got it. Very nice. My wife is actually from Montreal, so more the French side, but I know there’s a lot of good stuff and innovation happening. 

Michael Serbinis: Yeah. Toronto is going through a renaissance, a hypergrowth period. There are more cranes in Toronto building high-rises than any other place on the planet. And we’ve got the biggest job growth in tech of the next three biggest cities combined in the last three years.

Alejandro: That’s amazing. And yourself, Mike, how did you develop this love for solving problems and engineering physics?

Michael Serbinis: I was a kid that grew up just outside of Toronto. My parents were immigrants from Greece. I’m an only child. I was a kid that liked to break things and then put them back together. I was enrolled in a school in a program where I had to do a science fair project. That science fair project ended up winning what I call the Nerd Olympics at an International Science and Engineering Fair, which got me into working with NASA, and thinking about rockets, and solving big problems.

Alejandro: And I understand as well that the first gig that you did after you graduated from, I believe it was the university there in Toronto was Microsoft. So how did you end up in Microsoft?

Michael Serbinis: I was presenting at an engineering conference about how I developed this high-temperature superconductor propulsion system, and a bunch of judges were there, and sponsors were there. Microsoft was one of the sponsors. Nobody in the judging group that heard me speak believed that I did anything that I was talking about except for the guy from Microsoft that came over and offered me a job on the spot. That became my job throughout college. So it wasn’t after; it was during. And I worked on new ways of routing packets on the internet. 

Alejandro: Got it. So what happened right after college?

Michael Serbinis: You know, most people in college in their senior year start looking for jobs and going to job fairs, at least that’s what happened when I was in school. In my case, I got a call from a guy that I knew from my freshman year, and he was like, “Hey, dude. I know that you’ve been at Microsoft. You should come and help my brother out. My brother and I are building an internet company, and we know that you’ve built software at Microsoft. Why don’t you come and work with us for zero money, and a company that has no name, and a company that has no funding, and you can sleep on our couch.” To the guy with immigrant parents that saw that their son, all the sudden, had all these opportunities, including moving to Seattle and to Redmond to go work at Microsoft and make six figures. Making zero figures, working for a company with no name and no product and no investors seemed like an absolutely crazy idea, but I did it, and that was to go work with Kimbal and his brother, Elon Musk at a company which would later be named Zip2.

Alejandro: Tell us about those days. What was it like working with the Musk brothers?

Michael Serbinis: Kimbal’s a guy that I knew from college, Queens University. Elon also went to Queen’s but left to go to Penn to study business and take some physics courses, I guess. Kimbal was very much the sales and marketing guy. Elon was the strategist tech guy that hadn’t really been an engineer or a coder but was very much the visionary. We were the classic Silicon Valley story. My first weekend there was 72 hours straight of standing up a web service, which back then there were no tools, so you had to create them, and then deploy them, and then build your application, which for us was a local search and local classifieds kind of service like a Yelp. We worked constantly. My first ever trip to Vegas was like a trip on the company was with Elon and Kimble and a few other guys. We basically worked around the clock to prove out the product, get funding, get customers, and keep the ball rolling.

Alejandro: How was it like to work with what people are coining as one of the most remarkable entrepreneurs of our era with Elon Musk? What did you learn from working with him?

Michael Serbinis: He’s a super-intense guy, and clearly an intelligent, brilliant guy. He’s a guy that despite maybe not having the sports or athletic gene, he has an incredible, insatiable desire to win and to be on top. I guess that probably would be my biggest takeaway. He was a few years older than me and it was my first experience not just building technology, but building product and building a company, and the desire to win, and this approach of how to build a company even though I’d say we differ on a bunch of aspects of how, but that was my takeaway. I left and went to go start my own company, and I’ve been doing that ever since.

Alejandro: Very cool. And Zip2 ended up being acquired by AltaVista for 300 million cash. I guess that was their first successful outcome of Elon Musk. So let’s talk about your first rodeo. Let’s talk about DocSpace. How did you come up with the idea, and how did you decide to say, “Let’s go and do this”?

Michael Serbinis: I happen to be in a diner called the Wayne Gretzky Diner, very Canadian, of course, in Edmonton, Alberta, where my girlfriend was living and working, and I was visiting. I happened to be having breakfast with a friend that I played volleyball with. By accident, I spilled coffee on the guy beside us. All the sudden, he and I were building a business two weeks later and starting a company. This idea was pretty simple that we wouldn’t be using FedEx, and we wouldn’t be using document careers services in the future. We’d all have our documents, our files, our videos, our pictures in the Cloud, and we’d be able to access them from our computers and probably other devices in the future. So, your documents in the Cloud was kind of how we got started. We named it DocSpace. We started building effectively one of the first cloud companies.

Alejandro: So how was it like to – now, you’re the founder and putting a team together, and especially, in this case, you were acting as the CTO. What was the process like of recruiting engineers as well and building up the business from the ground up?

Michael Serbinis: Yeah. Building a company versus a product or a technology, for me, was just way more exciting and way more a complex problem, way more interesting. I actually played the Chief Technology Officer role as a co-founder. Our other co-founder played the CEO role. But to be honest, it was a mad sprint to build this company and be one of the 800 lb. gorillas in the space over a very short span of time. I would say one of my biggest takeaways from my Zip2 experience was how valuable and how important culture could be if you really focused on your people and focused on that as a competitive weapon, and keep part of your strategy versus just building a better app or just building technology. Building culture was probably the biggest thing that I put energy into and that I took out of it because it was success. Those people that were part of our early DocSpace team, we were a family. We were a competitive team and a global sport. We all wanted to win. It was my first example of if you give people a mission that they’re passionate about, and you set high goals and a global ambition, people become better versions of themselves. They grow. They rally to a place where 1+1=1,000, a million. That’s what winning companies are made of. It’s not just a cool technology or patent or a slick product. You need people. It’s a team sport, and culture is what makes those teams winning teams. 

Alejandro: 100%. It’s all about the people. And here, you guys got really lucky, and I think that luck is preparation meeting opportunity. But definitely, the opportunity here not because you guys literally sold the business before everything came crashing down.

Michael Serbinis: Yeah. The timing was miraculous. Sometimes, it’s better to be a little lucky than good. This was one of those circumstances where we incorporated and got going in November of ’97, and by November of ’99, we had signed an agreement to be acquired for about half a billion dollars. By March, when the deal closed, it had closed seven days before the market peaked in the year 2000, and then everything started to tank. If that wasn’t lucky enough, in the next six months, our new company, Critical Path was still growing, and while the market was tanking, our company was growing, and our stock price went from $19 a share to $126 a share. So what was a half-a-billion-dollar transaction was now, because it was a cash and stock deal, was now like a 3-billion-dollar transaction?

Alejandro: Wow. How long did it take? How did this deal come about?

Michael Serbinis: You know, we were talking to other companies in the space, and they were finding us, who believe that the Cloud is where the action would be in the future, that all applications and data would just live in the Cloud. I’m not sure anybody really understood what the Cloud was, and that could still be the case today, 20 years later. We thought the winners in the category were not going to be necessarily one-application wonders, one-trick ponies. They were going to be suites of applications and suites of services that individuals and eventually companies would sign up to. So we met through that process. It started out as a partnership discussion, and all the sudden – and you know, they were darling at the time. They were on the cover of every magazine, cover of Fortune, and whatnot. All the sudden, we got to, “Hey, these two things are better together.” One Salesforce, one distribution strategy, one cloud infrastructure. And Critical Path had something like 27 data centers around the world. The two just made sense together. To achieve our mission, to be like the leading global cloud platform in what we were doing, we just felt like it was the better path. We had no idea what would happen in the market, and we had no idea that the value would balloon. These were crazy times.

Alejandro: Yeah, absolutely. Why would you say that it took so much time? We’re talking about almost eight years for you to go at it again. Why?

Michael Serbinis: That is a great question that I think about a lot. I have no regrets, but I do think about what were all the factors? One factor was I definitely saw the opportunity to make Critical Path into an even bigger, better version of itself. The market had other ideas. The telecom bust came after the dot-com bubble bursting. 9/11 happened. Things got very complicated, and I stuck around. It’s more typical that you exit, you’re in the dead presidents’ club, and in 12 months you leave. For me, I was really open to learning. I had gone from product guy, engineer guy to founder, CTO. I had more money than I was ever going to need, and that was not really what was important to me. I just saw it as an opportunity to learn. If I had been purely financially-motivated, I might have just ejected after a year and started something sooner – something new again sooner. But I wasn’t, and I really saw something really exciting, and the people were frankly, by the time I left, it was a lot of my DocSpace team members that were in senior leadership positions in the C-suite, and I loved it. I was a young guy traveling to every country on the planet at least a few times a year. So it was a pretty fun gig.

Alejandro: Got it. After that acquisition, you did five years with Critical Path, and then you did Indigo. If you got one learning from your time at Critical Path, and then another one at Indigo, what would those learnings be? Just one from each.

Michael Serbinis: You know, at Critical Path, I think it was my MBA, and I stayed too long. If I did a sort of tradeoff, pro/con analysis, and if I had that training, and if I had that mindset, I would have left sooner. Know when the right time is to move on would have been the headline. I moved back to Canada because I met my wife. We did a spreadsheet, and somehow, Canada won. Toronto won the places to live. She was a banker on Wall Street, and I was living in San Francisco, and somehow, we ended up in Toronto. A friend introduced me to Indigo, and the Chairman and CEO there, who’s a great entrepreneur that’s built a great business, and she was wondering what happens when books go digital. I think if anything, we should have just gotten to that part sooner. I had never really worked in a large enterprise before. I was always a builder, and so my headline would have been to stay true to yourself. No one had ever taught me that being an entrepreneur was a path in life, but I discovered it. I discovered it there because a year and a half in I’m like, “All right. It’s been nice being back in Toronto. I like the people here, but I just need to get back to building something because that’s who I am, and that’s where I can be magical, and where I have superpowers, and that’s a lot of fun. 

Alejandro: Let’s talk about these superpowers. I think the idea is sort of like busses. They just come and go, and eventually, the door opens up, and you decide to get in and use those superpowers. What would you say made you think that getting into that Kobo bus made sense for you as the next space?

Michael Serbinis: Number one, it’s the realization that “All right. I just need to get back to building something. I know I can do this, but I’ve got this expertise – a network where I know how to sell, and I know how to sell in 190 countries. I know how to build platforms that serve hundreds of millions of people. At the time, those were giant numbers based on the size of the internet and mobile footprint in the world. And along came this problem that looked like a once-in-a-generation or multi-generational change where books were going digital, and it was going to be global. The paradigm would shift, and the business model would shift. And it probably needed someone from not inside the industry, not a publisher, not a bookseller, but someone that knew how to build tech platforms. It just seemed like a category that I could be passionate about and something that needed someone like me. So, I dove in.

Alejandro: You were talking about the excitement from going back to building, but this time around, you had a different approach at building. It was more as the CEO, more at the forefront, and taking other responsibilities. So how was the transition from being used to perhaps being the founder more on the technical side to being more the founder that would be leading the charge forward?

Michael Serbinis: To be honest, it felt like it always should have been what I was doing, to be completely candid.

Alejandro: Yeah.

Michael Serbinis: As much as I love building tech and building products and the nuts and bolts, I guess what I love more is leading, and telling a story, and getting people excited whether they’re investors, or media, or people on my team to go and create great things and build things that make the world better. So it felt pretty natural to me. I’ve always viewed building companies as a team sport, so that’s what I focused on is building my team. I’ve shared this story a few times, and people find it interesting, so I’ll share it here. I knew exactly who my competitors were. I don’t mean the logos. I mean, I knew that there was going to be a two-horse race ultimately. All tech categories tend to go that way. There’s a global competition. There’s one podium. There are three people on the podium, and nobody remembers #3.

Alejandro: Yeah.

Michael Serbinis: So I had an idea that there would be Amazon, and there would likely be like a pure-play, a Netflix of the category, or a Spotify of the category. I felt confident that could be us. I knew exactly who the individuals – their names, what school they went to, their spouses. I knew everything about the Kindle team, and I sought to build a much better, bigger, stronger, faster team and build a culture of speed and a culture of openness and collaboration, which frankly were elements which I felt I needed to win. I needed to move faster. I needed to partner. The enemy of my enemy is my friend, kind of mentality. And I needed to build a technology platform and a solution that at its core was open versus their platform which was closed. I built a team, and I built a culture around those core values. Ultimately, more than any aspect of our product or technology or pricing or anything, I look at that as the root of our success.

Alejandro: As this point, you already had the financial muscle. You had the previous substantial exit, so you really, really didn’t need any investors here. Why did you bring outsiders into the cap table?

Michael Serbinis: That’s a good question. I think it’s mostly because of how the idea came about and the circumstances. Heather Reisman was the CEO and still the CEO of Indigo. She knows that world. She’s got the resources outside of Indigo to invest as well as the resources and a platform within Indigo. It just made more sense that it was a natural thing to partner with them and bring them onboard versus eject, start something new, put in my own capital for – what could it be? It could be double the money – I don’t know – triple, 50% greater. So I wasn’t really optimizing for what my or what our initial team’s potential take would be in the future. I was optimizing for success and time was of the essence, and we had a great platform where we could build and test our model. Very quickly, we exploited that platform to 190 countries, and we figured out how to do that way faster and way better than Amazon could I think precisely because of how we started.

Alejandro: Really cool, and you know there’s this saying that says: once, you’re lucky; twice, you’re good. Obviously, this was the second time that you built, you financed, you scaled, and you exited. Why did you think that it was the right time, or at what point did you say to yourself, “Hey, maybe we should explore getting this to the finish line?

Michael Serbinis: We had a tiger by the tail. Our very first year from getting our Series A, and we changed the name to Kobo. It was not the original kind of project name. From 12 months from that, so just from December ’09 to December 2010, we booked 110 million in sales. I don’t know many startups that have ever done that. I mean, it was a pretty crazy situation, and we both had a hardware business and a digital book or content business. And one led the other. So you put a device in someone’s hands; they buy it at a bookstore or a Best Buy, and now they become dedicated, loyal book buyers that don’t turn and don’t switch to other platforms. Whereas, if you get someone to download your app, but they may not stick, and they may have four apps on their phone, and they’re not really dedicated buyers because they haven’t committed. So having a device was key. We needed to sell more, and get more distribution, and kind of suck the oxygen out of the room by partnering with all the national booksellers, the Barnes & Nobles of the world that mattered. Unfortunately, in the U.S. we chose Borders who later went bankrupt like, frankly, a lot of bookstore businesses. Even Barnes & Nobles today is struggling. It just got sold private equity. Anyhow, we had to move. We had to move fast. 110 was going to become 250 million in sales in the next year. The challenge with hardware is you have a working capital need that most software or software service customers don’t have. The challenge with hardware and funding hardware is a lot of investors in the venture world get skittish of “Well, wait a minute. What if you don’t sell it? Then we’re sitting on like this boat anchor. We’ve sunk all our money into this inventory that may never sell.” So, investors were kind of skittish. I had a tiger by the tail. I needed to keep funding it, or I was going to lose. We had raised a 50-million-dollar round in April of that year, but all the sudden as I was getting into August orders from retailers around the world, I realized I needed to raise 150. I was 100 million short. What were my options? Go public? Get another investment round. “Sorry, guys. I’m just kidding. I meant to say 150, not 50.” Or potentially explore a big brother or big sister-type partnership, which is when eBay and Amazon and Rakuten start knocking on our door. 

Alejandro: So how long did the process take from beginning to end on that process?

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Michael Serbinis: I had a call from this random guy from Japan that I had never heard of before in my life, and it was 11:00 at night on a Thursday in August – noon in Japan. Two days later, they all flew in on the company jet, and we had an offer on the table shortly thereafter.

Alejandro: Wow.

Michael Serbinis: There’s some complexity around the other players that could also put in offers based on competition, bureau, and all sorts of legal, regulatory stuff that I didn’t totally understand. But I think it was by the end of August I was in a hotel room in Paris with my primary shareholders and the Rakuten guys. At the end of that, we shook on it, and we went into diligence, and we were done shortly after.

Alejandro: Wow. What were the terms of the deal? How much was it?

Michael Serbinis: It was an interesting deal because it started with a bigger price and the desire to lock up the founders and the executive team for like ten years, which that’s crazy. I basically said, “How about zero years?” They said, “Well, that’s crazy. How about five years?” I’m like, “How about zero years?” Eventually, the price came down, and it was like a 315 million cash deal, 24 months later from coming out as Kobo. So we’re talking about the fall of 2011. The deal had another mechanism, which was phantom shares in the new company, so we all got effectively the same number and value of shares the next day after closing, but they would be marked to the revenue multiple of another digital content company that was public. And the only one at the time was Netflix. So there was a secondary exit downstream that was on the order of just under a billion dollars based on the multiples of our revenue and our revenue growth, which was great.

Alejandro: Very, very cool. I was very impressed when I didn’t see any vesting and resting. You literally took no time. So we’re talking about the beginning of 2014 when you finally closed this chapter, and at the end of that year, you were already with your next rodeo. So why don’t we talk about the next one, League? Why did you go with this one?

Michael Serbinis: I’ve got to tell you an interesting story that happened in the in-between. I was not planning to jump back in for sure. Kobo was exhausting. I was literally on a plane for it every four weeks. I had a young family that I was not spending a ton of time with, and a new daughter that was born just after the acquisition closed, so she would have been around two in 2014. I had planned The Summer of Mike. I was going to do all sorts of fun things. I made the final decision actually to leave right after the Super Bowl. I’m a huge sports fan. I went to the Monaco Grand Prix. I was going to the World Cup. I was doing all sorts of – I went to Wayne Gretzky’s Fantasy Camp in Las Vegas, and I was doing all kinds of fun stuff. In the summer, I was going to spend time with my kids. One day my middle daughter says to me, “Dad, are we okay?” I said, “What do you mean by that?” She said, “Well, are we okay? You know, for money because you’re not working. You’re not like the other parents. You’re kind of hanging around. You’ve got this funny beard growing. Are we okay?” And I said, “We’re totally fine. There’s nothing for you to worry about.” She was showing a lot of empathy at seven years old. Then she said, “Are you okay?” I was really taken aback, and again, “What do you mean by that?” She said, “Well, you’re not really inventing things or building things, which I know is what you love to do.” That was the turning point. I was like, “All right, it’s time to go back to starting something because clearly, this is not working for the family.” When your seven-year-old notices that you’re not doing what you love, it kind of tells you things. That was the impetus, and I had this thinking about what are the next things that would go through a similar transition, this mass consumerization of everything? What are the next things that are going to go from like Grandma’s cable TV subscription to Netflix? Being someone that is very passionate about health, and frankly, I was traveling around the world and trying to do that and stay on and at peak performance. I invested a lot in my own health and fitness. I started to think about healthcare, and how does healthcare become consumerized, and when does that happen? And does it happen? My quick conclusion was: it’s going to happen. It’s going to be personalized. It’s going to be preventative. It’s going to be digital, data-driven, and it’s going to be always on, and there will be a platform for that. And like every other tech category, there will be a #1 and #2, and no one will remember the rest. So let’s go build that. I got the band back together again, although everybody was on similar Summers of Dan and Summers of Mike. So we got started in the fall formerly, and we kicked off League in November of 2014.

Alejandro: What ended up being the business model, Mike?

Michael Serbinis: We thought it was going to be this consumer-driven marketplace model. We were right about consumer-driven or consumer-centric, but what it’s evolved to is an enterprise model. The fact is that enterprise employers spend about a trillion dollars a year on healthcare, and it keeps getting more expensive. Nobody likes it, and one-size-fits-none. So it’s time for a rethink. It’s such a big part of overall company cost and payroll cost. And the leading employers have concluded like, “The solution is not coming from the existing industry players. There needs to be a new way.” If you look at the amount of investment, and the amount of money and how critical this is – I mean, if this were a manufacturing problem, you’d be running ASP. If this were a go-to-market problem, you’d be running a CRM like Salesforce. Every enterprise will run on Enterprise OS for health care in the next five years. It’s a SaaS model, and the economics are pretty simple. You invest in a SaaS model per employee per month, and you’re going to bend your cost-curve, save money on your healthcare cost, put people in the right health programs and services at the right time, and that will also help them be happier, healthier employees that stick around, and our part of building whatever company they’re at. So it’s a vertical SaaS model, and we’ve learned that over the last two and a half years that we’ve been out selling. It’s definitely starting to – well, it’s beyond starting to. It’s in liftoff phase now.

Alejandro: Very cool. I see that you guys have raised over 70 million. You have like about 200 or so employees. Obviously, growing the operation very nicely. There’s one question that I want to ask you. What have you learned about deal-making? What is your biggest lesson?

Michael Serbinis: About deal-making?

Alejandro: You’ve raised a lot of money. You’ve sold multiple companies. You probably learned something that gives you the edge. Spill the beans with us, Mike. 

Michael Serbinis: Yeah. It’s ultimately very human. This is about relationships, and deal-making between people ultimately has to have a win-win component to it. You need to be able to envision yourself and walk in your partner or potential partner’s shoes. You’ve got to create something that is a win for them as they do for you. If you can’t arrive at that, you’re generally not going to get there, and if you do, you’ll probably get there, and it will be someplace you don’t want to be. So win-win opportunities that are driven by people who have built a relationship and just see a better future together than apart. I think that’s my biggest lesson above any financial engineering or all sorts of deal constructs. To be honest, the simplest deal constructs are the best. The ones that are about creating a better future versus solving a short-term problem. Those are the best deals.

Alejandro: Of course. And as you’re looking back if you had the opportunity, and this is a question that I typically ask the guests that come on the show. If you had the opportunity to look back, knowing all these different things that you’ve known about building and scaling companies, if you had the chance to have a chat with your younger self, with that Mike that was about to launch the first company, let’s say DocSpace, what would be that one piece of advice that you would give to your younger self knowing what you know now about business before launching the company?

Michael Serbinis: I kind of wish I had someone telling me, “Here’s the roadmap for this, and you can do it.” I never had that to be honest. I never really knew what an entrepreneur was and did. There weren’t accelerators and incubators. I just didn’t know what it looked like. I’d say the closest role model I had was, I remember at the time, Bill Gates was an icon in the industry, but I just didn’t know what the path was. I was kind of making it up as I went along, and when you’re making it up, there are always moments of self-doubt and imposter syndrome. Can I be doing this? Should I be doing this? What am I doing here? Is this going to work out? But just the confidence that could be gained by the elder me or someone like me saying, “Dude, you can totally do this, and here’s how you do it.” That would have been great, but I didn’t have that, and I had to make it up as I went along. But it’s worked out.

Alejandro: It definitely has worked out. So that’s pretty cool, Mike. For the folks that are listening, what is the best way for them to reach out and say hi, Mike?

Michael Serbinis: They can find me at League either through LinkedIn, or I’m just Mike Serbinis on LinkedIn. Or just reach out at mi**@le****.com

Alejandro: Fantastic. Well, Mike. It has been a pleasure to have you on the DealMakers show today. Thank you so much.

Michael Serbinis: It’s great to be with you. Thank you.

 

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