Ep #15: Rachel Jacobson

PODCAST TRANSCRIPT:

Dhani Jones (00:03):

The Pathfinders podcast is presented to you by Ansarada. Ansarada is the modern deal and virtual data room technology designed to make M&A, capital raising, divestments, restructures and IPOs as simple as possible. Since 2005, Ansarada has been trusted in over 24,000 transactions, and empowered over $1 trillion worth of deals. Ansarada is a secure space that includes workflow tools, AI-powered data rooms, and built-in Q&A and integration frameworks. It's the data room trusted by modern dealmakers. You can start for free today at ansarada.com. 

 

Dhani Jones (00:55):

Welcome back everybody to The Pathfinders, presented by Ansarada. I'm your host, former NFL player, investor and entrepreneur, Dhani Jones. Today I'm joined by Rachel Jacobson. Rachel is the president of the Drone Racing League, the global professional drone racing circuit seen on NBC, Twitter, and other premier sports networks internationally. And before that, she spent over 20 years working at the NBA, finishing her time there as senior vice president of business development. She's with us today to share some of her dealmaking stories, give us an inside look into the high speed world of drone racing, and offer her insights into what it's like to break the glass ceiling in the world of professional sports league management. Welcome Rachel.

Rachel Jacobson (01:37):

Well, hello there. Thanks for having me.

Dhani Jones (01:40):

I just want to say I'm so excited to talk to you because we met not too long ago, but we immediately hit it off. And there's just something about your personality that I knew was quintessential in the way that you move through the world. We sat down, we were trying to have some food, they thought we needed some reservations, but no, we don't need reservations, we need Rachel. Because when Rachel sits down, people just listen to you. I mean, has it always been this way that as soon as you walk into a room, people have to pay attention or else they're just going to read the riot act because you're just going to get it done regardless?

Rachel Jacobson (02:22):

Well, I don't know if the listeners know, Dhani is also my PR manager, so he's definitely keeping that job. Thank you for that warm introduction. And yes, I don't know. I got that gift early on of just figuring out what I needed to do to really engage with people both on the social side, on the business side, and I think it served me well in terms of building and really forging these relationships like ours.

Dhani Jones (02:54):

Well, I mean, either you learned it on the fly or maybe you learned it at Cornell. I mean, you had to learn it somewhere. I mean, there had to be some sort of early experiences through maybe entrepreneurship or just getting to know people. But what were those watershed moments that provided this path? Because being in business management, being in professional sports, we know how it's dominated, we know how it's ruled. It's an aggressive atmosphere. It's just like the locker room and you had to have these skills either taught or you saw it along the way.

Rachel Jacobson (03:30):

Yeah. So, I mean, I have a winner mentality. I love that. It's like, I'm a winner, I figure it out, I make it happen, but it doesn't always come easy. And I think growing up, I played team sports, I was on the track team, I was also the head cheerleader, so maybe that's where you get a little bit of my ‘ra ra’ from. It was a good intersection of competitive team sports and then being the consummate cheerleader both in business and as well as doing that. But to your point, it was really just that will to win where in the academic world, in middle school and high school it doesn't always come easy. And as my mom liked to say, I would be up till the wee hours of the night studying for the test. For other people, they have a photographic memory and they didn't need to study as much.

(04:27):

But I just always felt like I wanted that step ahead. And what comes from wanting to get an advantage there is being prepared. And I think again, as you know from being a competitive athlete, you have to put the work in, and when you put the work in it's going to set you up for success. So when I was an undergrad at Cornell, I think I spent four years working every weekend at a thoroughbred race track. And when I got to interviewing for full-time jobs, one of the things that really differentiated me was ‘you're a college student, you're usually out socializing, partying on the weekends’, and when I talked about my work experience and my internship, I said, I worked at thoroughbred race track, their biggest days were on Saturdays and Sundays so I was working every weekend for four years. So I think at those interviews they understood, okay, she's got incredible work ethic and discipline to really say, this is a priority for her.

Dhani Jones (05:40):

Yeah. When I was in college, I worked at a bike shop and I think that the best days at the bike shop are pretty much every day. So I would go to class, and I would go to practice, and then I'd go work at the bike shop. I mean, I have such a respect for those that work their way while they're in college, regardless if they're working just a little bit of time, but the fact that you were on the ground at the track Saturday and Sunday, I mean, you probably could have predicted who was going to win the Kentucky Derby this year. I should have probably called you. That was my fault.

(06:12):

And the fact that you also stayed up late as a young child, I did the same type of thing. I think there's just something in the personality of a person that drives themself to work so hard and have that amount of diligence and have that amount of effort, because you're not going to get it by sitting on the couch all the time. And being in the NBA for 20 years, management training, working all the way up to the top as a senior vice president, I mean, was it staying up late or was it working at the track that got you there?

Rachel Jacobson (06:48):

Well, the NBA is a great story because I wanted to come out of undergrad and be in the sports and entertainment industry. I just felt like it was a perfect marriage of my interests, my skill sets - like you've said, my energy. It would be a good career path for me. And the NBA had started this management training program. It was David Stern's model of what Dick Ebersol did at NBC where they had this media training program called the Page Program. So David started this a year prior to my graduation. He hired seven people that first year. I was in the second year class. And what I loved about this opportunity is he wanted to really cross train this group of people to bring them in the organization, move them quicker, have them understand the inner relationships at the different departments to essentially become the next leaders of the company.

(07:47):

And I was so fortunate to have that opportunity and have that access to David at the time who was the commissioner, Adam, who is now commissioner, who was the deputy commissioner, and Mark Tatum, who's now the deputy commissioner - all these senior leaders. So I saw firsthand how they figured it out early on in their careers to set them up for where they were and I just took everything in. I was always the one raising my hand for more. I lived at home with my parents for three years. I got on a train every morning at 6:10. Thank you to my father, who I will make tune into this. My dad would drive me to the train every morning at 6:00. He would then pick me up at night. And at my wedding, he talked about those favorite 12 minutes of the day that we were together and there was this excitement of me really attacking every day that I had going into work.

Dhani Jones (08:52):

Wow. I mean, I have to ask, what did you all talk about in those 12 minutes?

Rachel Jacobson (08:59):

Usually work. No, but a lot of family stuff too. I have an older sister, I have a younger brother and we're very connected. I'm very fortunate that everyone lives so close. So we would talk about that. We would talk about my agenda, what meetings I had, what interesting people I was going to meet. And then usually by the time he picked me up there were stories about my mom during the day, we did this and we did that. And our family is also very involved with thoroughbred horses, as you know, when you mentioned the Kentucky Derby. So throughout the year at different times, Saratoga leading up to the Derby, it's a lot of horse talk too.

Dhani Jones (09:45):

Well, I think, to be able to spend that quality time in your professional career with your parents or with your father, I mean, not a lot of people can say that. And I know they're proud of you. And I think it's amazing to be able to look back on those moments and sort of realize how instrumental they were in the major transitions that you have had and the relationships that you've built along the way. Not a lot of people can just call David Stern, David, or Adam Silver, Adam. I mean, you're just calling these people that run a major organization by first names because you've developed those personal relationships, and they've helped, and they've fostered your growth along the way. Was there one moment in time when David, or Mr. Stern, or Adam, or Mr. Silver, said something or did something or helped you in a way that allowed you to break through the ceiling?

Rachel Jacobson (10:47):

Definitely. Whenever David reached out to you, or as you say, David Stern, there was always that anxiousness, what's David going to ask about? He was the most knowledgeable and well read. In every boardroom, in every meeting, he was always 10 steps ahead. So you really had to bring your A-game when you knew that you were going to be in his presence. Well, times that by 10 when you don't know he's going to be calling you and just everything that goes through your head about, why is he calling, what's he going to ask about? And my watershed moment, to your point, was I was sitting in my office. You see, at the time you used to use phones where it would come up (the person's name that was calling you), and I saw David Stern. And he said, "I want to talk to you about something."

(11:36):

And at the time I was selling sponsorships for the NBA. So I had moved from partnerships, managing the day to day partnerships to really going out and sourcing new business and meeting with companies, understanding what was important to them, and putting together the most dynamic, innovative types of partnerships. A lot of money was being invested in the league and doing all of these incredible things together. So at the time the NBA and the WNBA were separate in terms of who was selling sponsorships.

(12:18):

So David picked up the phone, I saw him, and he said, "Hey, hotshot. I want you to sell the WNBA as well. You have a great passion for gender equity. I've seen what you've done here at the league on the sales side. And we want to look at really co-oping these opportunities. There's no reason why we don't go after multifaceted partnerships where a company is investing in the NBA in the WNBA." Now it makes perfect sense. At the time, it was one of those structural things that it was a little bit of a separation. So I was like, "Of course, I've got it." And I think it was at that moment where he said, "Hey, hotshot, this is really important, this is good for everybody here, kind of figure it out," that I found myself not just wanting to show success and please him, but I found myself starting to think much more strategically about the business.

(13:28):

And one of the things where he was instrumental in moving me to business development is, "Rachel, everyone wants to see that you can run a company and you can raise money." I know that's a little bit of what you've got your hand in right now. When you think about investing it's sitting across from investors, knowing what's going to be important for them to get the confidence to make a bet, because essentially it's a bet, to make a bet on you. So a roundabout way of saying, for me, it was when David asked me to do this other thing that I then went into a whole other gear of not wanting to just show success there, but I made sure that every company was investing in the WNBA. And I think for me, that's always been a passion point and to have early on in my career being part of really that growth trajectory has served not just me well, but the entire industry when we think about companies needing to support women's sports in general.

Dhani Jones (14:46):

Well, your heart had to be beating out of your chest when you got that phone call from David. And even when he said, "Hey, hotshot." I feel like you already knew something big was coming. And you'd been preparing your entire life, I think, from the time that you spent at college, the time that you spent in the car with your father, the time you were working at the track. I mean, you are used to the proverbial gun going off and it's your time to make something happen. And I think that's something that you've carried alongside with you.

(15:17):

And so when he was able to give you that opportunity and you took it on, how did you take some of your past experiences and equate that into your dealmaking mindset? And also, how did you remain passionate in what you're doing? You're doing stuff in the NBA, and now you had to kind of cross promotionalise, you had to cross sell into the WNBA. How did you take that deal making mindset, remain passionate, and just basically close everything in order to set the new standard? Because no one's just getting the name hotshot without actually doing something big.

Rachel Jacobson (15:53):

So I was obsessive in understanding everything about the league, the players, the business structure, the owners of the WNBA teams, because again, they're all shareholders that we wake up every day to take care of. And I just started thinking about who are some of the most powerful women executives, who are some of the male counterparts that are running companies that need to show diversity in their workforce, and who need to be out there promoting when you think about getting customers and clients, you want to show that you're as invested in women as you are in men? So I tried to flip the narrative around, not just pitching a company, but pitching more of a holistic opportunity. Like, you are making an investment, not just in basketball, but you're making an investment in an opportunity for your company to really shine a positive spotlight on what you are doing to break these barriers and really highlight the best of the best in women on the court and off the court.

Dhani Jones (17:15):

The Pathfinders podcast is presented to you by Ansarada. Ansarada is the modern deal in virtual data room technology designed to make M&A, capital raising, divestment, restructures and IPOs as simple as possible. Ansarada has just launched Freemium with the world's first online data room quote. Now you can get a free data room and quote in just three clicks in just 15 seconds. There's no need to wait, get your room open straight away no matter what stage you're at, deal marketing, deal preparation or due diligence. And here's the best bit, usage fees only start when the deal goes live. All the top M&A firms and investment banks are jumping on it because there is no risk, just reward. Pretty cool, right? Check it out at ansarada.com/quote. You know I like a winning team so say it with me, ansarada.com, for your next winning outcome. What was one of the biggest deals that you did?

Rachel Jacobson (18:12):

The Pepsi partnership.

Dhani Jones (18:14):

How big was it? Rachel, I just want to know how you got the job done because a lot of people would've been like, "Oh, it's Pepsi." They would've been nervous. They would've sat back. They would've been like, "Okay, well, I need to take some time and figure things out." I'm pretty sure the first week you made a phone call to someone at Pepsi you closed the deal in less than two weeks. I know it. So how did you do it?

Rachel Jacobson (18:33):

Eight months. It was eight months.

Dhani Jones (18:36):

So how'd you get it done?

Rachel Jacobson (18:38):

So that's a good one because we had been partnered with Coca-Cola for 30 years. This is talk about a game changer. We had been with one company literally for 30 years. They had one of the signature events in the season, they had been with us through thick and thin, and we looked at the landscape of that category and just wanted to figure out what we could do with Pepsi. At the time Pepsi was investing in all of the other major sports leagues. They had NFL, they had NHL, they had MLB. And we looked at their marketing prowess. So I got connected with their head of sports and entertainment, Adam Harder. I think we talked about it early on. No money was ever discussed at the onset. I'm a big proponent of building the relationship, figuring out what is important to that company, and the other stuff will happen.

(19:44):

There's a time and place for dealmaking on the financial side. And it was really clear that there were things that Pepsi wasn't getting from some of the other properties. And we brought a diverse set of consumers. When you looked at the multicultural aspect of the NBA, we had a younger demographic than some of the other sports leagues, and we had some of these crown jewel moments for them to be part of. And at the time, Mountain Dew, their energy drink, when you think about it, it was like aligning an energy drink with the pace of the NBA, along with having a global footprint, and like I mentioned, just an audience that they were not getting from some of the other properties. So we got it done.

(20:38):

And I remember one of the highlights was not just on the dealmaking side, but Indra, who I so revere for everything that she had done for not just women as such a successful CEO, but she had seemed like an incredible individual from all I had read, but we had never met live and I wanted to make a great impression of course. And one of my signature things coming off the T-Mobile partnership was I was always in magenta because I'm rocking the brand colors. So you better believe that I showed up at the Pepsi press conference wearing Pepsi blue and Indra, the first thing she said after, "Rachel, so nice to finally meet you," because my counterpart at Pepsi had talked about me just like I had spoken about Adam to my David, and she said, "Thank you so much for wearing the home team colors." So that dress was a winner and companies care about things like brand identity or helping them really stand out as well. So it was wonderful to meet her and it's continued to be a successful partnership as I now watch from my Drone Racing League seat everything that's going on with the NBA partnerships.

Dhani Jones (22:02):

Well, I'm sure you have that dress framed somewhere or kept on a mantle because that's a critical transition point in one person's life where they're able to convert upon an opportunity and prove your worth to the person that basically held you up and gave you an opportunity. And I think that David, God rest his soul, is to be commended for that, because then you were able to make a couple of different transitions. You're going over to Landit where they're revolutionizing professional development for women, a new approach to career and acceleration. But then, I mean, what was the decision in leaving the NBA? Because a lot of people, it's the biggest thing. So why did you decide to leave the NBA, go to Landit, and then how did you ultimately get to the Drone Racing League?

Rachel Jacobson (22:49):

So you are correct. A lot of people probably scratch their heads. I was at the height of my career, heading up global new business for a property that's got 99.9% household penetration. Everybody knows the NBA. It's the number one top tier professional global sports league and it's the NBA. Everybody loves that company. And I'd been there over 20 years. So for me, it was really a personal decision that I had an ambition to run a company. And the only way to do that was to really go work for an early stage company. And I really felt like this was way more time than I thought I would spend at the first act in my career. But every year was wonderful and I was learning new skills and I was raising my hand, so it never felt like 20 years was as long as it sounds out loud when I think about my own age and having worked there half of my life.

(23:58):

So in terms of my decision to leave, I just proactively told the NBA that I wanted to pursue something more entrepreneurial, that it wasn't them, it was me, it was not a bad breakup. It was much more of I loved every minute of this career, I am so grateful for the opportunities, I want to go out and figure out what's next for me. So essentially I left as a free agent. To your point of, what were people thinking? It's like, you pick up your toys and these are really nice toys at the NBA. You pick up your toys with not the next job, but I was betting on myself. So I bet on the fact that I could go to another company and be one of the first 5 to 10 employees, help build it, and then ultimately see what was next after that.

(25:01):

So Landit was an incredible opportunity that, to your point, is revolutionizing career management. It's using technology to power careers, which is when you think about technology running the world, just an incredible opportunity for companies to invest in their people. And I loved every minute. We were raising money. I was managing business. I was under tables packing gifts for clients. I did everything and I loved every minute. There's no task too small or too big. And everyone had said that. They're like, "Rachel, you're so cut out for an early stage company, but you are going to fall off a cliff in terms of people around you doing things." But I've always been wired to do a lot on my own and not ever act like I'm above anything. I'm always doing the same job that anyone who works for me does, so that came pretty easy.

(26:07):

And I'm humming away at Landit, helping to build the company to be incredibly successful. And enter back your favorite person, David Stern, in the fall of 2019. I had always kept in touch with my friends at the NBA, but David, every couple months I would go up to his office and he had been investing in a lot of technology companies that were connected to sports. So he kept going into the city. He was working every day. There was no retirement as he hated people. Just because he didn't have his commissioner title, he was working his tail off. I don't know if I can use any other words there. But he was working as hard as he ever did. And in the fall of 2019, we went to an event together and he called me that night and he said, "We should talk about getting you back to sports."

(27:06):

And at that point I'm like, "I love what I'm doing. It's great. It really, really is." And there was no timeline on it. There was no time to get back to sports. And for me, I had been away from sports for a couple of years and I could see myself going back to it, but there was no time horizon. And next thing I know, I - really out of left field - got a call from a headhunter that had worked with the NBA, but couldn't touch me when I was there. And she called me and said, "I need to meet with you about something." It was the middle of December. I think it was snowing outside. And I said, "I'll see you after the new year." She said, "No, I need to see you before the new year." And I went to meet with her and she sat across the table from me and said, "You're going to be the president of the Drone Racing League."

Dhani Jones (28:03):

And you said, "Yes." You said, "Absolutely. I'm ready to go."

Rachel Jacobson (28:07):

I was like, I heard a few of those sound bites, she told me a little bit more, I asked a lot of questions and I went home that night and I said to my husband, "I met with Michelle James. She talked to me about a Drone Racing League." I didn't know. I mean, I'm a sports girl. As you know, season tickets to the giants, I'm following everything going on. I have a 12-year old boy, girl twins. So we're all in on Auburn and professional and this and that. But I did not know enough about the drone league. And my husband said to me the next morning, "You're going to take that job." And I was like, "Wait, what? I haven't even met with the founder."

(28:54):

So P.S., Dhani, I met with Nick Horbaczewski, who's just a brilliant visionary. And we went out, he talked to me about taping up drones in the backyard of a home depot and wanting to build a sport that was inclusive, that was tech first. I bought anything he was selling I think that day. I don't even think I ate. I think we met for lunch. I didn't even end up eating that day. But I just felt like everything he needed to make this sport a mainstream sport, a billion dollar business, I was trained to run those plays. And if I took the job I would start on day one just building a navy seal operation of academy trained people to work here that know how to do the sponsorship, the marketing, the event production, and that's what we've been doing for the last two years.

Dhani Jones (29:54):

Well, I've been a big fan of the Drone Racing League. And I remember when you're racing through different old malls, old buildings and just leveraging the technology to create a completely different experience, but the business itself as it's grown has probably been most affected by your leadership qualities, I mean, and your leadership philosophy, that's how a company grows. So what are some of the key intricate factors of your leadership philosophy that you've infused within the business to allow it to grow to where it is today?

Rachel Jacobson (30:31):

Everyone has a sales mindset and I think that has served us really well. You can be running events for us, but you have to think about the end goal that we want fans around the world viewing our sport as the most brilliant thing they've ever seen. We want our partners feeling like we bring in a net new audience and we are positioning them as contemporary brands and we're setting them up for success. So this notion of having that winner mentality and the sales mindset, I come to work every day, I am the head cheerleader, it starts with my leadership there and I infuse that throughout the company.

(31:19):

And I'm allowing a culture of learning where when given this opportunity I had 25 years experience at two other companies where I wanted to take the best of the best. What were the things I loved about my best managers? What were the things that irked me or didn't want to make me bring my A game every day? And I'm like, how do I build that culture that really invests in people that could forever change their lives and careers? Because I can have a hand in that. I want to look back and say, you were part of history.

(32:03):

Our children, our grandchildren are going to grow up in a world, just like Kevin Plank said at UnderArmour, where before UnderArmour there was Nike, there was Adidas, kids now are born into a world where UnderArmour exists. And I want that same thing for the Drone Racing League where we are this tech driven mainstream sport and you are going to see us on primetime networks. We have millions of fans around the world, and we're going to be like one of your favorite sports that you can watch and love our pilots who are athletes throughout the year.

Dhani Jones (32:43):

So you've had championships in Vegas, you guys are all over the place in NBC sports-

Rachel Jacobson (32:49):

And by the way, you heard it here, you better be coming to sit court side at our opening day race, which we haven't announced yet, but you have a personal invitation from me to be my guest.

Dhani Jones (33:01):

Well, I'd love to be your guest. And I will definitely take you up on that offer because I think that the future will be in drone racing. And the fact that the league brings so many of the athletes together in order to be able to showcase their skills is important. And as we kind of come to the conclusion of our chat, because you and I could talk for hours, there's the sport side, but then there's also this unique intersection of sport, technology, and then also where the military comes into it. So I know you guys have a renewed partnership with the United States Air Force. So I just want to just hint and talk a little bit about that. Because when it comes to negotiations you're doing deals with brands, but then now you're doing deals with the military. I mean, that's a whole nother level. I mean, you thought Pepsi was big. The military is big and you secured it.

Rachel Jacobson (33:54):

Thank you for bringing that up. They have been a fantastic partner of ours for the last several years, but it's also such a key differentiator when you think about talking to us about a partnership with the Air Force, a partnership with Algorand on the blockchain side, with the technology companies that we work with, I feel like my competitive advantages... And listen, I know all the teams that are running the NFL, NBA, MLB, but we get to sit across the table from companies and talk with lithium batteries and chip manufacturers. They can't do that.

(34:35):

Because our drone is essentially our ball. So to be able to open up this range of companies like the Air Force, who, by the way, they want people that love aerodynamics and flight. So you look at our population, I'm like 30 X times more invested in being interested in the Air Force when you think about flying drones. So I have a tailor-made population that they can recruit in and they already know this is a filtered audience. You're not just running a Super Bowl spot and spending 10 million dollars for a hundred million eyeballs. We're targeted when you think about being able to reach a demographic with precision.

Dhani Jones (35:28):

Well, anybody that sits across the table from Rachel knows that they're going to become her best friend and she's going to convince them that whatever she's got, they're going to want to work with you in order to do it. So just in our last question here, we always talk about meals and deals, so what's your favorite place to celebrate your biggest deal or how do you celebrate your biggest moments? Because you've had so many of them.

Rachel Jacobson (35:57):

Oh, my favorite place to celebrate is at home with my family. So my kids, my husband, they've been so much a part. My parents. Literally my favorite days are going to the house I grew up in New Jersey where my parents live, my dad barbecuing, or going out to one of our favorite restaurants and just celebrating the opportunities to be all together.

Dhani Jones (36:26):

Well, you and I are going to celebrate when I sit court side and hang out with you as we watch this amazing experience.

Rachel Jacobson (36:35):

You know what? Actually Dhani, I'm going to upgrade you. You're not going to be court side. You're going to be on the flight deck.

Dhani Jones (36:41):

Okay. I could do that too.

Rachel Jacobson (36:42):

I love that.

Dhani Jones (36:44):

I'm in it. I'm in it. I just want to say, Rachel, thank you so much. You've given us so many different bits and bites that I hope everybody's really taking to heart. And I think one of the things that you said that was most important, you got to be able to be able to and be willing to do anything and everything. When you were packaging things underneath the table, when you were making the phone calls, it didn't matter who was on the other end, you were going to talk to them like they're your peer. And when people like David Stern call you and they recommend things for you, being able to not shy away, but move towards it. And I think that's the dealmaking mindset and the path that you've laid for not only yourself, but so many people that are coming after you as well. So Rachel, thank you so much for joining us.

Rachel Jacobson (37:30):

Well, thank you for having me. This was great.

Dhani Jones (37:33):

A special thanks again to Rachel Jacobson for being with us today. It's really amazing to see the work she's doing in the world of drone racing and learn how the Drone Racing League is coming to investing and dealmaking from a whole new perspective. If you're enjoying The Pathfinders, please make sure to leave reviews so more people can find this show. Until next time, I'm Dhani Jones, and this has been The Pathfinders presented by Ansarada.