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Why One of the Most Successful CEOs (and Entrepreneurs) You’ve Never Heard of Still Thinks He Has a Lot to Learn

I’ve always been proud of the fact I worked my way through college. My full-time factory job not only paid better than any of my friend’s jobs, it started me on a path for the next 20 years of my professional life.

And then I met Daniel Sillman

While still a student at the University of Michigan, Daniel launched Compass Management Group, a multi-family office for athletes and entertainers. (Philadelphia Eagle Brandon Graham was his first client; the list grew to include thirty more.)

Then he cold-emailed billionaire Steve Ross, who owns Related Companies, RSE Ventures, is the majority owner of the Miami Dolphins… (Which seemed like a natural move since Ross, a noted philanthropist, has his name on the Michigan Business School building.)

A year later Daniel sold his business, joined RSE Ventures, and is now the CEO of Relevent Sports Group.

But wait, there’s more: Along with Maverick Carter, Carmelo Anthony, and Nate Forbes, Daniel co-owns Del Toro Shoes, a high-end footwear and apparel brand. He’s a founding investor in Performance Inspired Nutrition, Mark Wahlberg’sline of supplementsHe’s a venture partner at 3L Capital. Along with Golden State Warrior Draymond Green, he co-owns Blink Fitness franchises.

That’s just a partial list of what Daniel accomplished before turning thirty — none of which you likely knew, since he prefers to stay out of the limelight.

Which, as I realized when we talked, could be one of the secrets to Daniel’s success. 

Conventional wisdom says build your brand through social media.

I like having a low profile. Don’t get me wrong: It’s nice to get recognized once in a while… but I try to be inconspicuous. 

Don’t get me wrong: Some people love it, it works for them, it helps them build a fan base or a base of credibility… but I’m like you. I would feel very self-promotional. 

Some people like to show they have unique access. Unique relationships. Know certain people. I try to keep those things private.

I’ve always prided myself that if you ask people in the industry about me, ask the people I work with, or peers, or colleagues, or across the table… that’s all that matters. Real, long-term relationships and reputations are what matters. 

Besides, I have my own mental collage of memories. (Laughs.)

While in college you decide to start a business that no college student would imagine launching. Where did that come from?

I was in the Ross School of Business getting a finance degree. Brandon Graham was a close friend of mine. Unlike most athletes, he liked to hang around the business school kids. (Laughs.) When he was turning pro he wanted me to be his agent. I said, “No, but I’ll help you look for one.”

I also realized he basically needed to start doing retirement planning at age 22. He needed a budget, a plan to handle his liquidity needs, the right insurance, an estate plan, a place to live… there were all these financial planners trying to land his business but in the short-term, he needed to figure out how he wanted to live relative to his budget while also focusing on long-term wealth preservation and growth.

I looked at the family office model for high net worth individuals and realized no one provided a vertically-integrated financial services platform for athletes.

Athletes should have no less access. Most don’t have the resources, the background, they’re told to just focus on, say, football, and that’s why so many professional athletes later go bankrupt at such a high rate.

Clearly there was a need… but it was a huge leap to decide you could fill that need.

I realized there was a white space to do it myself. So I talked to my father and a couple of mentors, brought a lot of ideas to different people… and they didn’t shoot me down right away. (Laughs.) I met with probably 20 different people and they all said it was a great idea.

So I started a multi-family office for athletes and entertainers, Brandon was our first client. 

And recently he just signed a $ 40 million contract extension. He’s financially set for the rest of his life, and I bet he’s in the 99th percentile of pro athletes in terms of balance sheet and personal liquidity.

It turned out to be a unique opportunity that we grew to 30-plus athletes and entertainers. I also was lucky enough to bring in Joe Dumars as a partner. He was the general manager of the Detroit Pistons at the time. I learned a lot from him on how to deal with athletes. What really set us apart was not only our expertise but our ability to communicate our expertise.

I was the youngest person in the company I founded and ran. I hired experienced accountants, insurance professionals, investment professionals, all of them 30 years my senior who had the expertise.

It was a huge learning experience for me, and there was an altruistic side as well because we also got do some real good for our clients. 

And it was a great start to my career because it taught me how important it is to build reputation and relationships.

That’s an important point. You were really young. You were seemingly inexperienced. How did you gain trust?

Let’s be honest: Many athletes and entertainers get taken advantage of. Lots of people sell a shiny object.

Take Brandon: The financial advisors waiting to talk to him were shiny-suit salesmen. They couldn’t sell a wealthy, experienced, financially-savvy person. So they tried to sell 21-year-olds.

It was our job to help educate our clients, help them understand the financial realities, the opportunity for their families… ultimately, you’re talking about people. 

Joe Dumars helped me learn that. Mark Wahlberg helped me learn that. Hearing from people who made it… and had kept their wealth… that helped me learn the importance of communication and education. It’s so hard for athletes and entertainers to manage their day-to-day careers, let alone devote time to learning how to manage their finances — which, if you think about it, is a business in itself. 

Ultimately, when people heard what I had to say, when they understood the level of thought and research I had done while also acknowledging I still had a lot to learn…

And I was good at putting smart people together and letting that be the basis for what we could provide.

How did you get past the “credibility gap” with professionals in the different advising fields?

I had the advantage that sports and entertainment are an intriguing field. Plenty of people want to be involved. And many successful people love mentoring younger people.

In short, show a real interest in learning and you can gain a lot of friends and allies and mentors. 

I had a leg up from being able to say, “I’m coming in talking about pro sports, entertainment, media…” pretty sexy topics. (Laughs.) And I love learning from people who have done it before. Add that up and it was a pretty potent combination. 

So what made you cold-email Steve Ross? That would be like a 20-year-old cold-emailing Mark Cuban and expecting a response.

If you want to learn, and have curiosity to get better, you have to be around smart people.

Maybe you know someone in common that helps you overcome the barrier. If not, find a hook, reach out… and if they say no, what have you lost? Nothing.

I didn’t know Steve’s email, so I sent emails to a bunch of different email combinations. I said, “I went to the Ross School of Business, here’s what I’ve done, here are a couple commonalities… and I would love to pick your brain.”

He responded and said he would be happy to meet me but it had to be at the business school at about 10.30 p.m.

Today he jokes that he met me because he figured anyone willing to meet that late… he might as well meet them. (Laughs.)

That turned out to be a lot more than a 20-minute chat. How did you prepare for it?

I was really nervous. So I scripted the whole meeting out:  I was going to explain my business, ask what I should do to grow, how I could take my business to the next level… but because he’s such a regular guy and so disarming, it just turned into a conversation. That lasted a couple hours. 

And by the end of the meeting I was on the phone with the Dolphins and with other people he thought could be helpful.

And then he followed up the next day. And the day after that. 

So I started coming to New York to spend time with him. He gave me great advice on expanding my business, and then he convinced me to sell it and work for him. So I did. I sold my business, moved to New York to work for Steve on business development and mergers and acquisitions. 

It wasn’t a hard choice: If you have an opportunity to be around a guy like that all the time, and all the successful people around him… you’d be silly not to take the opportunity. 

Speaking of opportunities: Relevent is placing tremendous focus on soccer. Why?

I was at RSC Ventures running business development. We had made a number of different investments in a variety of sports businesses. 

Relevant was bringing El Clasico to America. (El Clasico is the name given to matches between Real Madrid and Barcelona.) It’s bigger than Michigan vs Michigan State, bigger than Celtics vs Lakers. I went to Madrid with Steve, Maverick Carter, and others and I had never seen anything like it. The sense of community and passion is unparalleled compared to American sports. I thought our events were crazy — this was on a different level.

It was a unique opportunity to bring the biggest sport in the world to the biggest sports media markets in the world.

We’re a live entertainment business, not just a soccer business. There’s a huge global reach. We leverage our expertise as event producers, marketers, and storytellers to get into other businesses. 

The opportunity is tremendous. In the last seven or eight years the value of international media rights has grown from under $ 50 million to over half a billion dollars. The audience for international soccer is growing, MLS has grown their fan base… there are lots of tailwinds for the sport. It already exists there and the clubs finally have a real interest to grow their brands in the States. That’s what got me excited.

Opportunities also create challenges. What are some of the hurdles you’ll have to overcome?

One is the European soccer calendar. That’s ever-changing, requires ongoing conversations with UEFA and FIFA… that’s certainly a challenge.

Internally the challenge is similar to every growing business: We went from 12 people to 70, from a two-week event to an always-on media company… we have a joint venture with La Liga… building a much more successful business means getting the right talent and right expertise in the door.

That’s been my biggest focus over the last year: Getting the right people in place to support our ambitions. 

Fortunately, I love that. I love operations,. I pride myself on putting great management teams together.

My friends say I’m always “collecting” new people. That I turn 3-person dinners into 12-person dinners. (Laughs.)

Many entrepreneurs don’t think about using joint ventures to grow, if only because that can mean giving up the total control they sought when they started their businesses. So tell me about your joint venture with La Liga (the top Spanish division.)

You’re right. But joint ventures can be transformational for a business.

That’s the case with our historic deal with La Liga. In my opinion, they’re the most progressive league in growing their value outside of Europe. They’re actively growing their brand in the U.S. and Asia.

Keep in mind that 70 percent of the U.S. soccer audience speaks Spanish. For many, soccer is their first sport. Bringing La Liga games to the U.S., bringing (Lionel) Messi to the U.S., developing content, getting TV distribution with broad reach so people can watch all the teams… basically to dig into a strategy that brings matches to foreign territories in much the same way we’ve exported American sports. 

We entered into the deal in August of 2018. It’s the first time a league has done a joint venture and set up an equity partnership with a local partner. 

The role of a startup founder naturally changes as a company grows. As Relevent has grown, what has changed for you?

I’ve had to step back from certain things, which is hard. (Laughs.)  

My natural instinct is to fix everything. It’s tough to not just insert myself and try to solve every problem. 

That’s the same for anyone who runs a business. With any organization, the key is building a great team.

But I’m fortunate to have the support of a guy like Steve Ross: He allows us to dream big. And I have a lot of other great mentors that I call on.

That’s my best advice for anyone: You have to have people you can call.

And you have to realize how much you don’t know.

To be honest, when I first got the Relevant job I had a lot of confidence: I had built and sold a business, had done well at RSC Ventures, was coming off of El Clasico… my head was bigger than it should have been and I fell on my ass a number of times because I had lost the curiosity that had allowed me to be successful. Under my initial strategy we tried to do everything at once. We should have done things in steps.

And in the meantime I was getting too far in the weeds in certain areas.

I thought nothing could stop me, and I’m lucky that I got smacked in the face by the fact I wasn’t as great as I thought I was.  (Laughs.) I had to get put back in my place so I could be a better leader.

And that’s the thing: No matter how successful you think you are, keep reminding yourself how little you’ve accomplished relative to other people.

Take Steve Ross: If Steve Ross can always be learning… I can definitely always be learning.  

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