DraftKings’ next big bets

JASON ROBINS: Anything could happen, but it’s one of those things that we just culturally are like, “This is too potentially disruptive to ignore. We have to invest in, this and we have to turn this into an opportunity.” Anything that you don’t turn into opportunity, it can turn into a risk for you.

JEFF BERMAN: DraftKings CEO Jason Robins is constantly scanning the horizon for the next big opportunity. Prediction markets, yep. AI, yep. A big bet on a Super Bowl ad, absolutely all of the above. For Jason, as for the Super Bowl champions, the strategy to win is simple: Bet on your team.

ROBINS: The reality is they know how to do their job. Some things are going to hit, some things are going to miss, but no one really knows until you actually do it.

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BERMAN: This is Masters of Scale. I’m Jeff Berman, your host. This week on the show is Jason Robins. He’s the co-founder and CEO of DraftKings. His company is a massive player in the sports betting industry with a market cap of over $13 billion. We spoke with Jason on Super Bowl’s Radio Row in San Francisco just ahead of the big game last weekend, covering the rise of prediction markets, the need for responsible gaming, and after starting DraftKings with just a few buddies in the equivalent of a garage, his advice for anyone starting a company today. 

Jason, welcome to Masters of Scale.

ROBINS: Thank you for having me.

Copy LinkHow DratKings maximizes the impact of Super Bowl marketing

BERMAN: Thrilled to have you. If you are in advertising, Cannes Lions is your Super Bowl. If you’re in consumer electronics, CES is your Superbowl. The Super Bowl is literally your Super Bowl. What is Super Bowl week like for DraftKings?

ROBINS: Well, it’s a lot of work leading up to it. We have a ton of things that we want to get ready, everything from new product features to marketing campaigns. So, the week of, I’m here for most of the week doing stuff like this, lots of meetings, watching the numbers every day, tracking things against how we expect it, all that. Then by the time you get to the game day, everyone’s pretty exhausted, but we grind through. We actually give the company the day off after the Super Bowl because so many people work on Sunday and Saturday. I mean, so you’re working for the whole weekend, we give people Monday off.

BERMAN: I think the Monday after the Super Bowl should be a national holiday. So DraftKings can get behind that.

ROBINS: I agree with you on that.

BERMAN: That would be great.

ROBINS: I agree.

BERMAN: That would be a very popular campaign for you guys to run. 

Let’s talk about the numbers. Order of magnitude: How big is the Super Bowl and Super Bowl week relative to an average week in the year?

ROBINS: Well, it’s the biggest day of the year for us. It’s a single game. So relative to weeks where there’s lots of games, obviously it’s got to be much bigger on a per game basis. So it just dwarfs any single event that we have. And it’s not just big in terms of volume. It’s big for us to activate customers, to get new customers. Just everything is about the Super Bowl. And then the goal for us after that is to hopefully give them a good experience. They want to stick around for things like March Madness and NBA and NHL and PGA and all the other things coming up.

BERMAN: How much is actually being bet on the Super Bowl through DraftKings Super Bowl week?

ROBINS: Can’t give you a number exactly.

BERMAN: Directional.

ROBINS: Hundreds of millions.

BERMAN: And that includes prediction markets?

ROBINS: Well, that’s pretty new for us, so I don’t actually know how that’s going to look. I mean, we’ve literally been doing that for like a month, so it’s still pretty new. It won’t be a big number in terms of our overall this year. But I do expect to see a big jump in growth on the Super Bowl for that. We’re hoping to get a lot of new stuff in the product for them. We’ll see if we get it in on time. I think we will.

BERMAN: So, I want to come back to DraftKings predictions in a moment, but the challenge of the Super Bowl is it’s the biggest marketing platform in America, and also it is so crowded. It’s really hard to break through. How do you and your team approach that?

ROBINS: Well, the good thing for us is our content is endemic. It’s basically so related to the game that it’s already something people are paying attention to. People already associate the Super Bowl with betting. They already are thinking about all the novelty bets, like which color the Gatorade will be and things like that. So, we’re already starting from a place where the mindset of people is already there. It’s tough because you never know with creative what’s going to resonate. What we try to do is experiment a lot throughout the year and figure out what types of messages, what types of offers, what types of creative will resonate. But we haven’t done a Super Bowl ad in two years now. So, this will be a nice one to come back to. I’m really excited. We have a partnership with NBC, so it’s a big part of that.

BERMAN: What changed? Why did you not do one the last two years and you’re doing one this year?

ROBINS: The biggest thing is we had just done one for a few years, and we decided that looking at the data, it made sense to take a year off. And I think this year with the NBC partnership, we also have more creative things that we’re able to do in terms of integrations with the overall broadcast. And I think that will make the creative in the Super Bowl perform better.

BERMAN: Is there a piece of Super Bowl marketing that you’ve seen that isn’t in your category that you just think, “Oh my gosh, that’s brilliant. I wish we had a version of that or I’m so impressed with that one.”

ROBINS: It’s funny because I never really know which campaigns. Even when I’m watching it, the ones that are like the biggest aren’t the ones that I would’ve thought. Every once in a while, there’s a year where you have one that just everybody’s like, “Yeah, that’s the ad.” But it teaches me a lesson. And I always tell people this, creative, everyone has an opinion on. It’s not something that you can be that straightforward with. And I’ve seen things where I and others are like, “That’s terrible, and it kills it on performance.”

And so over the years, just let the marketing team do their thing. Unless I really think we’re doing something bad, I’m not out there saying, “I think we should do something different,” because they’re already hearing that from a hundred different people. And the reality is they know how to do their job. Some things are going to hit, some things are going to miss, but no one really knows until you actually do it.

BERMAN: I think if you haven’t done this, this is hard to understand that that’s the case when—

ROBINS: Oh, most people, I think my initial instinct was like, “I have an opinion on this. I want to tell you what I think.” But I’ve also been doing marketing for a while, and I’ve been working with my CMO who I think is unbelievably smart, and I trust her completely. So, I also realized that I got to let her do her thing, and there’s a lot of trust there.

BERMAN: And the Super Bowl ad is so different because it’s one piece of creative. You’re spending probably a good bit of money to produce it. You’re spending a fortune to put it on TV. Whereas, I go back to when I worked at the NFL, when I ran the digital media group there, our head of marketing would put the top 10-20 landing pages up, and we would put our initials on the one that we thought would perform best. And almost invariably, no one would pick the one that would work best. And so, I think if you’re not in this industry, you don’t really understand that it is a lot more art than science.

ROBINS: It is. You’ve got to use the science to figure out which of the art forms are working, but 100%. And I’ve just too many times had situations where what I thought happened was not what happened. 

I’ll tell you the other thing about the ad that we’re doing a little differently this year and one of the reasons we took last year off, a lot of our customer activity and getting people engaged comes before the game. So, we did a lot of advertising going into the game. And then during the game, people are more focused on watching. This year though, we have made so many great upgrades to our live betting product, and that’s the perfect opportunity for it in the game to try to really take a shot at getting some live betting activation. So that’s really what the campaign will be about this year. So that’s a new experiment for us. We’ve actually never really tried something like this before where we’re really pushing live betting in the middle of the game, see how it goes and we’ll learn from there.

Copy LinkHow DraftKings approaches responsible gaming

BERMAN: The evolution of this market has been pretty incredible. And you just launched prediction markets. You’ve got live betting, which is becoming more and more part of the experience. And in a blowout, live betting continues to keep people engaged and interested. It’s better for the broadcasters, better for the advertisers. 

It also presents some real challenges, right? I mean, you’ve got people who are addicted to the gambling, who are risking family savings and potentially putting the mortgage up. How is DraftKings approaching its role in being a responsible corporate citizen here and not contributing to the problems we’ve got in the country right now?

ROBINS: Well, we have been a big proponent of responsible gaming. We’ve invested a lot in it. We have a person who reports directly to me. Lori Kalani is our chief responsible gaming officer whose sole job is to focus on this. And we made a ton of progress. We actually just released a data sheet, which we could share with you showing real data and stats behind what we’ve been doing because it’s one thing to talk about. It’s another thing to show in the numbers that we’re actually doing it. We’ve had so much engagement with our responsible gaming tools. And one of the things that we’re trying to get for people, change the mindset of people, is you’re talking about problem gaming. Those are people that shouldn’t be on the platform.

And our goal is either through them self-identifying or us identifying them to not have them have access to the platform. But there’s a lot of other people who can play, but they still should be playing responsibly. It’s no different than any activity. If you’re spending money on something, you should understand how much you’re spending. You should have a budget. 

We have tools that help people do that. So, we have stats that show here’s how much you’ve spent. We have tools that allow you to set limits at all kinds of granular levels, daily, monthly, whatever you want. We have tools that allow you to say how much time you want to spend on the app and set limits on that. And it’s really meant to empower the consumer.

And what we want long-term is a sustainable customer base that is responsible, using our products, and enjoying them and getting entertainment out of them. It’s not good for anybody if you’re not having that. So that’s really the goal. And I think we made a ton of progress this year, and it’s going to continue to be a core part of our mission.

BERMAN: Is this a use case for AI? Can AI help you flag when someone is entering a problem zone and to flag it for them? Is there concern about companies being too paternalistic and telling customers what they can and can’t do. And also, this is a growing problem in the country. So how do you think about integrating AI to help address this issue?

ROBINS: Well, we’ve already integrated AI across many of our customer service touchpoints. And one of the things that AI can do, and I think this is part of what you’re alluding to. So, what happens sometimes, you have a customer that will interact with various people, they’ll interact with a piece of marketing, they’ll write into customer service, they’ll talk to their host if they’re a VIP customer, various things. And what AI can do is it could take all the communications, and there’s so many of them. So, it’s really impossible for a human to manually go through all this stuff and comb through very quickly and find any sorts of patterns that we may want to look into.

And then we have a dedicated team of people that can review those things and see if there’s anything that they think is troubling and follow up with the customer as necessary. 

So, I think that we’re just scratching the surface now. Obviously, we’ve got to be very cautious and responsible on how we implement AI too, and that’s something that’s very important to us. But I think this is a perfect example, what you’re raising and where AI can actually help. So many people come to me like, “Are you using AI to get people to bet more?” And it’s like, actually they’re not thinking about these types of things, which is using AI to actually improve responsible gaming.

BERMAN: Is there a concern about AI used offensively against DraftKings? Are you worried about people gaming your platform using new AI tools?

ROBINS: Like any new technology, you have to think about those things. And with anything, there’s going to be people that are looking to utilize it to win more. And so, obviously, we want to give people a shot at that. So, we want to make sure that we’re using AI too to help set our lines and help manage them. And I think it comes down to being on top of new technology and making sure that whoever’s on the other side of it isn’t using a technology that we’re not prepared for and we should be using it too. And I think that creates an equilibrium in the playing field.

BERMAN: Still ahead, more with Jason Robbins on the rise of prediction markets in sports betting and beyond. 

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Copy LinkNavigating the evolving landscape of prediction markets

One of the interesting things about the category you’re in is that we were in a static world until 2018 when the Supreme Court lifted the federal ban on online gambling nationally. And now, with the rise of prediction markets and the exploitation of a lot of loopholes out there, it feels like we’ve gone from a duopoly with you and one other company to now there are multiple players here because prediction markets have entered this space in a more meaningful way. Is that the right way to view it? And what’s it been like over the last year as this has exploded?

ROBINS: First, you have to separate prediction markets from traditional betting. It is a different thing. Obviously, I understand the areas that people see similarities, but it’s a different regulatory framework. The product experience is different. And so, I view it as a space that we can incrementally add more revenue and win in and add more customers, especially in the states that don’t have our traditional sports betting product. I think it’s a fantastic product for places like where we are now, California, Texas, other states like that.

BERMAN: Because those are states that have not legalized online gambling.

ROBINS: Exactly. And so, we look at it more in that way as an opportunity for us. We’ve for years had competition. The market structure didn’t start this way. And if you look, it’s not like even by volume, the prediction markets or any more market share, if you put everything together, any more share, I should say, than some of the other competitors that we have that are not number one and number two in the space. And I think that could obviously change over time. There are more people if you want to look at it that way competing, but I don’t know that that necessarily changes the dynamic. I think we have to make sure that we’re developing a great predictions product, so that we can compete in that zone.

And I like to think that having a bigger suite of products and overall bigger ecosystem of marketing and all the various partnerships that we have, a brand that really has been built up with the sports customer over many years. I mean, we’re ubiquitous all over the airwaves and being able to over time tell a broader story of all the different ways that you can play sports with DraftKings and having people all over the country drive from that singular marketing versus having to spend incrementally, I think will be a huge advantage for us.

Copy LinkHow should the prediction market be regulated?

BERMAN: Are there things we shouldn’t be able to bet on in a prediction market?

ROBINS: Well, I don’t know if I’m the right person to answer anything about what should I–

BERMAN: You’re the CEO of DraftKings. I mean, who else should I ask?

ROBINS: I mean, I know, but that’s what I asked the regulators. I think that there’s obvious stuff that I just think is probably not necessary, but there’s a lot in the middle too. And so, I don’t think that’s really up to us. I’ll obviously have opinions if people ask me about specific things, but in a broad sense, I think things that could very, very easily be manipulated. We should be cautious with things that are just negative. Like, will this player get injured or something like that? It’s just not – I don’t view it as the right thing for the industry, and I don’t really think there’s a ton of consumer demand for it anyway.

So, stuff like that are some examples I guess I would give. But really, it’s so nuanced, and I think that’s what’s fascinating about it. The rules are about to be written and we’ll find out, but there’s going to be a lot of different opinions, and some people are in the purest category of, we shouldn’t restrict anything. And I actually get that viewpoint in some ways. I think the right answer though is probably some restrictions, but in a reasonable way, but I don’t think you’ve got to be careful they don’t go overboard there.

BERMAN: Yeah. I mean, look, but I want to push it on this for just a moment. I was on Capitol Hill for four years. I ran policy at MySpace. That was my entry point to the private sector. My view personally is that when you’re dealing with emerging industries, the best regulation comes in collaboration with industry. You can’t leave it to industry entirely because then it’s the Wild West, but also by and large, regulators as well intended as they usually are and as brilliant as they often are, are not equipped with the right knowledge, the right understanding of the market, the right understanding of the technology to do this on their own. It’s not to throw shade at either side, it’s just the reality of it.

And so, to me, there are negative things like a player getting injured. There are also like, life and death things. There are things about national sovereignty where I mean someone could be betting on the regime in a country falling and bet so much money that it actually incentivizes certain action to be taken. So, it seems to me that DraftKings and others in the industry do have some responsibility to say, “There are rails that we are going to set independent of what the regulators do. And we’re going to actually encourage the regulators to at least set the rails where we say and not just let it be wide open.”

ROBINS: I 100% agree with everything you just said. I couldn’t agree more. And part of why I’m a little cautious about – I’ll give you a couple examples, but really I’m overly expressing my opinion here – is I do think collaboration is important. I think that collaboration is important, for industry itself to be collaborating. So, I don’t want to sit here and opine on a bunch of things and others in the industry may have a different perspective on it. I think the important thing is for everyone to collaborate, as you said, and work together to get to the right answer. And I’ve had things where I had an opinion and after talking it over with various stakeholders, that opinion changed.

Copy LinkIdentifying and investing in the next opportunity

BERMAN: I was at the NFL from 2010 to 2013. It was a very different era there. You could not even say the G word or the B word in gambling or betting. It was taboo, completely different universe 10, 15 years later here. And we were starting to see the rise of daily fantasy back then. When it was just a couple of you starting this company, could you foresee the world that we’re in right now? Did you have a vision for what this would be?

ROBINS: No. I mean, when we started, there were three of us at DraftKings, and it was daily fantasy sports, that’s what it was. And I was excited about daily fantasy sports. I was a huge, still am, fantasy sports nut. I play in lots of fantasy leagues every year, a little less than I used to these days just because of time, but I still love it. And that was what I was passionate about, and I felt like that was a great business to build. 

And as things evolved and it became clear, which we had nothing to do with, that the Supreme Court was going to take up this case. We looked at it as, well, we have to look into that. And I think one of the things that if you look at any technology company that has been successful over the years, it could be anyone from an AI company to any of the big tech companies, right? They’ve really been aware of what the next thing is and investing in it ahead of time, AI being a great example now.

And take Google or whatever, Google’s initial business was search. I mean, if they had just stuck with search, where would they be right now? I think we saw that with some others that just stuck with search. So, it’s really something that’s just been a pattern with every company that you have. Technology and consumer behaviors change and move so quickly. If you’re not following that and you’re not investing in the next thing, then you’re going to get left behind and your old business is going to get disrupted. 

So, when we saw the Supreme Court had taken this up, we felt that way about it, even though initially never thought once about that, never. It was all about daily fantasy sports, and I love fantasy sports, but one of the things that I think our company has done a good job of, and we are doing it now with investments in AI.

Also, we were the first to mobile. We were not the first to have a website, but we were absolutely the first to get to mobile. And the reason was we looked at the data and I looked at it and said, okay, last year, this is our first year, we had single digit percentage of traffic coming on the mobile website. That’s up to 23, 24% the next year. And we all looked at each other and we’re like, “This is going to 80, 90% pretty quickly.” Now, it’s almost 100%. So being able to use data and just understanding where the world’s going has been something I think that’s been really beneficial, and I hope we can continue to do it. 

Predictions is a good example of that now, by the way. I think we’re leaning in there. And by the way, who knows how that’ll play out? Anything could happen, but it’s one of those things that we just culturally are like, “This is too potentially disruptive to ignore. We have to invest in this, and we have to turn this into an opportunity.” Anything that you don’t turn into opportunity, you can turn into a risk for you.

BERMAN: It was just a few of you back at the beginning. How many people are at DraftKings now?

ROBINS: About 5,600.

BERMAN: Okay. So, to your point about turning these moments into real opportunities, when you’re 5,600 people and you don’t have time to play in as many fantasy leagues as you or I would want to because of all the responsibilities of leading a company that large, how do you stay on the cutting edge of innovation? How do you make sure that you don’t fall into the traps of being sclerotic the way a lot of big companies get?

ROBINS: It’s all culture. Culture and quality of the talent that you have. If you have good people and the culture is one where everybody understands this is how we think about this, this is how we approach these types of situations. We talk about being calculated in how we take risks, not foolishly taking risks, being willing to take calculated risks though, and not being afraid of taking calculated risks. And that’s a core part of our culture. We talk about being quick and always looking for the next thing and getting there faster. We’ve often said that most companies that benefit from innovation didn’t invent the innovation.

Most of them just figured out before others that they needed to be investing there, and they got the right people, had the right strategy, and then they unleashed that talent, and they went and they got it done. And that’s true of virtually all the tech companies. I don’t know who started AI, but I don’t think it was Google or Meta or even OpenAI. It was probably somebody that doesn’t even exist now. So, it’s really not about necessarily being the one to come up with the idea. It’s about the one recognizing and being able to mobilize and action a team around a clear strategy approach, get the right talent in place, all those things.

Copy LinkBalancing organic growth and opportunities for acquisition

BERMAN: You referenced Google earlier. They just announced YouTube did $60 billion in revenue. That was a barely over a billion-dollar acquisition 20-ish years ago. When you think about growing inorganically, how do you think about acquisitions? I know you’ve done a few along the way, and how do you make sure that it’s not only the right buy for you, but that you’re able to capitalize on that opportunity so you can have that YouTube type success?

ROBINS: Well, YouTube, I mean, getting a success like that, I would love that. I think that’s rare. And what was amazing about that, as I’m sure you recall, at the time, YouTube was mired in lawsuits, everyone thought it was going out of business, and then Google comes and buys it for a billion. And I remember looking at that and saying, “I had viewed this as almost like a distressed asset. I can’t believe they’re paying this kind of dollar for that.” And now, look back and it’s bargain at that price, right?

BERMAN: Massively so.

ROBINS: Biggest bargains of all time. And it just shows again that, and I wasn’t in that, so I wasn’t looking at the data, they were looking at all that, but being able to recognize this is a trend. People are gravitating towards these types of video platforms. The way people are consuming video and media is changing and understanding that that was necessary and that was a platform that could help them develop that. But I would guess that most of what was done afterwards was really what made it successful. The acquisition itself was just the launching point. 

I think for us, we haven’t necessarily done any grand scale M&A yet. I don’t know if we will. I’m pretty happy with our organic path at this point, but we’re always open to different ideas.

In terms of the overall thinking on it, I don’t think for us there’s an obvious thing out there that I look at that makes sense for us to go aggressively after. So, we’re really heads down now focused more on how do we build the business organically as we generate cash flow on looking to buy back stock more than buy stuff, but that could change on a dime. It’s the same thing I was saying where you just always have to be looking, always aware, everything is timing. And right now, it feels like M&A is probably not a big thing for us, but that could change.

Copy LinkThe rise of women’s sports

BERMAN: How has women’s sports changed over the last few years from the experience of leading DraftKings?

ROBINS: It’s been a huge growth category for us. WNBA and women’s college basketball in particular, but also women’s soccer. Some of the fastest growing sports are in the women’s category, and everybody asked me, “Well, is that because you’re getting more women on the platform?” And yes, we are getting more. It’s still not as many as we hope, more male dominated platform, but that’s not necessarily what’s driving it. Basically, the same proportion that’s betting on NFL are betting on women.

BERMAN: Really?

ROBINS: Yeah. It’s people that just love the sport, which I think is great because the reality is you have more male sports fans. So, getting men betting on it and into it is going to grow women’s sports. And I think over time, it will bring more women in too. 

I think also, not surprisingly, when people are like, “Well, is that why you’re growing women on the pot?” No, actually the number one source of adding new women to the platform is NFL because just so many more people come in on NFL and that’s just going to capture a bigger net on an absolute basis. So, it’s an interesting dynamic in that sense, but the sports themselves I think are really benefiting from a lot of tailwinds. Caitlin Clark was obviously a huge catalyst initially in college and now in the pros and just interest has never been higher. So, I’m excited. WNBA in particular has really been skyrocketing for us.

Copy LinkWhy California and Texas haven’t legalized sports betting

BERMAN: After the 2018 Supreme Court decision, a number of states legalized the biggest part of your business now, but you referenced there are two very big states that still have not, California and Texas. Why haven’t they?

ROBINS: There are different answers in each, but as you might imagine, it comes down to political dynamics. I don’t think there’s a rational reason for it. It would make sense for both states. And I hope that over time that ends up making it happen. Usually over time, the right things come together and sometimes in the short term, politics and other challenging situations can prevent it.

BERMAN: How do you think about engaging in those politics? Because it’s tricky, right?

ROBINS: Well, in California, it’s all about having great relationships and partnerships with the tribes. California is a state where you have to run a ballot initiative, so a little bit less of a political process in the sense of that. But the tribes really, they control gaming in California. Doing this without them being on board is not realistic. So that’s been our goal, and we’ve been trying to figure out how to do it. I think the best way is for the tribes themselves to come together and lead a framework. And we’re just trying to build relationships so that we’re hopefully the ones that they want to build around, and they’ve been making good progress. We’ve actually gotten a lot of really great feedback.

BERMAN: California is staring down the barrel of a 20-plus billion-dollar budget gap caused by national political forces starting next year. The estimate I think I heard is that revenue from online gaming California could generate something on the order of a half billion to a billion dollars for the state. Is that a leverage point for you as you think about working with regulators, with legislators, with the tribes in California to legalize in our state?

ROBINS: In a normal state that wasn’t this dynamic with the ballot, it would be more so. I think because it’s a state where we really need to partner with the tribes and get this on the ballot and get it passed on the ballot. It’s a reason if that ever were to occur for elected officials to maybe call on all of us to come together and figure out how to get this done. But ultimately, it’s up to the tribes. And I think that – I’m not saying they don’t care, but they’re not as economically motivated by California’s budget gap as they are by protecting their own sovereignty.

BERMAN: It’s such a critical source of revenue for the tribes. It’s almost existential for them.

ROBINS: I think it is. But also, I think that there’s an element of there’s so many of them, but I don’t think most of them look at it as online sports betting isn’t something we should have. I think it’s, “how do we do it?” Having many, many tribes that need to come together and figure that out. It’s been why it’s been hard to get these types of things done in California.

BERMAN: Yeah. The demands on our time and attention are off the charts unprecedented. My team will tell you, they make fun of me. I will not use Slack. It’s just a productivity killer for me. As you’re managing Slack, text, email, Signal, Telegram, whatever other platforms you’re on, how are you creating time to think, to be strategic, to imagine the future?

ROBINS: Well, it’s interesting what you say. There are so many communication channels. Everyone knows: If you want to get me, don’t email me. You got to either text me or maybe WhatsApp me. I will use Slack, but not as much. And by the way, there’s people I’ve seen who can do it. I don’t know how they do it, but they’re all over all these things and don’t seem to be unproductive. That’s not me. I would lose my productivity in a second if I’m monitoring all these different channels at the same time. So, unlike you, I’m like, “This is what I do. I’m going to try to be super responsive on this. So, if you need me, you know where to get me.”

Copy LinkAdvice for future entrepreneurs and career builders

BERMAN: I want to get two pieces of advice from you. One, there are three young people sitting in a garage just starting a company today. One piece of advice for that trio.

ROBINS: I think the most important one is to get good people around you. Three people can’t build a company. You can get it off the ground a little bit, but you’re going to need to have other good people. And particularly that initial group of people you hire, that sets the foundation for everything. If you get that group right, that will be everything because those are the people that then are going to hire the next concentric circle of people. You’re not when you have 30, 40 people, you’re not necessarily the only one deciding who to hire. You have other people that are making sure you’re holding the talent bar high and you just built the culture and built the initial team that way.

And so, we were very disciplined about early on making sure we had a very great initial group that were people that we could see really building out that next group. And I think good evidence of it is many of them are still very involved in very senior roles in the company today. Not all of them, but it’s amazing how many people we have that have been around for 10 years plus that are in senior roles at the company right now.

BERMAN: There’s a 21-year-old who is about to enter the workforce, who is fired up by all the possibilities ahead and incredibly trepidatious, daunted by the changing economy, by AI eliminating entry level jobs. What are you saying to that young person?

ROBINS: Figure out what the skillsets of the future are going to be and try to manage your career in that direction. There is going to be a change in what types of jobs people need and where the demand will be. So, if you can recognize that, figure out how to become an expert, how to at least get initial exposure. Once you’re down a certain career path, it’s harder to change. So, figuring out what the next thing is. 

And then the other really important thing that I think is perhaps even more critical than that is figure out what you’re great at. So many corporate environments tell you what you’re not good at in your performance reviews. That’s important. You need to know what you need to get better at.

But early in your career, figuring out, “what am I great at? What can I really build a career around?” And I don’t even mean a particular job, but what are your skills? What are the things that you find make you stand out versus others? You’re not going to be as good at everything, but you may have some things that you can look at and say, “I actually feel like I’m in the upper category when it comes to that.” And then you really want to build your career around the intersection of those things with where the world’s gone.

BERMAN: Jason, thanks for being on Masters of Scale. It’s been a pleasure.

ROBINS: Thank you for having me. I appreciate it.

BERMAN: Thank you. Thanks again to Jason Robins for joining us. The rise of DraftKings is a stunning example of what’s possible when you make building a great team a cornerstone of your scaling strategy. When you’re in such a highly regulated category and so subject to court decisions along with state-by-state political dynamics to say nothing of the risks your core products present to society, Jason’s leadership is also an example to be studied in how you navigate incredibly rocky shoals. 

We’l have a lot more from our Radio Row conversations, spinning the world of sports, tech, media, and beyond on our YouTube channel, be sure to check those out. I’m Jeff Berman. Thank you for listening.