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Jill Smoller: Super Agent

Jill Smoller has made a place for herself as one of the best agents to some of the greatest athletes in sports. She joined “Out of Office” to talk about her journey and what might lay ahead in the next chapter.

Click here to listen to the full episode.

Jill Smoller is everywhere.

A superagent with almost 30 years of experience, her client list has included everyone from Florence Griffith Joyner to Kevin Garnett to the G.O.A.T., Serena Williams.

Smoller entered the business after her own career on the court came to an early end due to a series of knee injuries. And although her start as an agent came as the byproduct of a few connections and a little bit of luck, there is no denying that her ongoing hard work on behalf of her clients has made her a force in the industry.

But the path to becoming an agent started years before Smoller landed her first client.

At the age of 12, the youngest of four children, Smoller left her home in Larchmont, NY to enroll in the Nick Bollettieri Tennis Academy in Florida. From there, she attended the University of Arizona, where she was an All-American, and went on to play professionally.

“I ended up having a great doubles career, not particularly great singles career,” Smoller told Boardroom on the most recent episode of the Out of Office podcast.

By the time she was 26, Smoller called it quits on the sport she loved. Although she thought she would follow in the footsteps of her older brother and sister who had committed to the hustle of Wall Street, it was actually her other brother, who worked at Paramount Pictures in Los Angeles, who ended up making the connections that would pave the way for a future she had never thought to dream of.

After a few interviews, Smoller found herself working in the training program at ICM.

“I moved out to LA on a Sunday night, with no place to live and no car, and I had to show up in the mailroom at 6 a.m,” she said. “I think I took home $314 every two weeks.”

There, she used her keen powers of observation to make sense of a new business. In those early days in LA, she found the most informative opportunity came from a job no one else in her training class wanted to do: sort and collate the endless stream of faxes that came into the mailroom.

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“I always tried to get put on faxes, and everyone used to think it was because I was lazy,” she said with a laugh. “Every time something came in, I would read it, I would look at it… I had no background in the industry so I would take them home and I would study. That’s how I learned the business.”

Plus, as she was almost a decade older than most of her peers and freshly sober, she was able to draw from her life experiences and the various skillsets she had picked up along the way.

“Sports teaches you to problem solve, find solutions to things.,” she said. “And I think the nature of what we do [as agents] is to figure out how to turn a no into a yes. But also how to problem solve and, and get the most out of any situation.”

Her efforts were soon rewarded as Smoller found herself being promoted within 10 months, joining legendary agent Bill Block’s desk.

“I had a lot of contacts. I was older. I had a lot of life experience. I was a little bit of an enigma,” she said.

And she leveraged that mystery — and her promise as a connector — to land her first clients: Olympic gold medalist sprinter Florence Griffith Joyner and figure skater Katarina Witt. Soon after, she added Dennis Rodman in the waning years of his iconic and chaotic career.

“I learned a lot of my tactical skills [with Rodman] because there were a lot of situations,” Smoller said, offering a few choice examples of unforgettable moments.

She was quickly promoted again, becoming the face of ICM’s sports business in LA. And it was during this time that she began to build her connections with Richard Williams, father of Venus and Serena. He was drawn to Smoller’s signature spunk and grit and was intrigued by the young agent’s ambition.

As he sought representation for his daughters, he delegated a small sliver of their business to Smoller. Their pairing seemed almost fateful: Jill’s last match as a professional took place at the same Indian Wells tournament where Venus made her professional debut.

From there, their relationship grew, and Smoller continuously demonstrated her talents as a problem solver while proving her loyalty to the family.

“I think in order to represent some of these best of all time, you have to be ride or die,” she said. “When shit’s coming down or their traumas and tragedies [occur], that’s when you have to do your best work…How you show up for someone in times of need is the measure of who you are as a human.”

As Serena got older and began to take more control over her career, Jill stepped into a more prominent role. Over time, she made a seamless place for herself in the Williams’ tight-knit unit. And as their personal and professional relationships grew, so did Smoller’s investments in the ups and downs in Serena’s experiences on and off the court.

She has witnessed first-hand the trials and tribulations of the direct impact of racism, and the lack of grace with which the media and the sport have treated Serena at times.

“Neither Serena nor Venus was ever given the compassion or grace ever coming up,” she said. “They have paved the path for this generation to be able to have this voice because they’ve spoken up. Serena’s spoken up on so many occasions, being an advocate for everybody else and having that uncomfortable voice that nobody wanted to hear and it was always criticized.”

Smoller points to the impact of these experiences on the current actions of other athletes such as Naomi Osaka who have leveraged their platform to stand up for themselves and their communities.

From Serena’s 23 grand slam titles to long-standing partnerships with major brands such as Gatorade, Nike, and J.P. Morgan and to the near-death experience of giving birth, Jill Smoller has been there for it all.

With the clock ticking on Williams’ career, Smoller is convinced that Serena is only getting started:

“Her 2.0 is going to be far greater than what she’s done on the court in terms of the impact that she has on the world,” Smoller said.

This next phase will mark something new for Smoller, too. What, precisely, that might be remains to be seen, but it will undoubtedly be the next iteration of greatness that defines all of those that have come before.