Jake Olson experienced NIL chaos; now it’s his business

Jake Olson leans forward, resting his elbows on a long wooden table in a Newport Beach, California, office where the five-man leadership group of his budding tech start-up is dialing into a pitch meeting. It’s the start of a new round of fundraising, and he tells the wealthy men on the other end of the call that their business, and their industry, is on the precipice of exponential growth.

His two most trusted and loyal companions sit by his side. Daniel Hennes, the company’s CEO who was previously Olson’s roommate at USC, is rattling off talking points about the huge opportunity in front of them at his typical breakneck pace. Quebec, Olson’s 11-year-old guide dog who was previously listed as the company’s Chief Barking Officer, is snoring softly as he naps at Olson’s feet.

Olson wears a pair of dark sunglasses and his company’s name, Engage, across the chest of a gray T-shirt. He is explaining to the potential investors how he and Hennes used their unique experience in college to build an online platform to make it easier for companies to book athletes and other celebrities for speaking events. After weathering the pandemic, Olson and Hennes believe the coming year will be a boon for multiple reasons — not the least of which is the unprecedented influx of eligible talent expected to invade the marketplace this summer.

“I’m telling you right now,” Hennes chimes in on the call, “a year from now there will be five other things we’re doing to make us money that we’re not even thinking of right now.”

Possibilities stretch further than the imagination at the moment for an industry that has grown quickly in anticipation of a tectonic change coming to the college sports world. Starting July 1, NCAA athletes in at least a half dozen states will be allowed to start making money from third-party endorsements. State laws will guarantee that players can profit from selling the rights to their name, image and likeness (NIL) in a wide variety of ways. The NCAA plans to vote at some point in the next week on rule changes that could open similar opportunities for every athlete under its authority.

College athletes in those states will be able to sign endorsement deals with sponsors or make money from speaking engagements, autograph signings, live event appearances, sports camps and lessons, social media shoutouts and any number of creative ways to cash in on their skills, life stories and popularity. Sorting through all those opportunities presents a daunting proposition for athletes.

Engage is one of dozens of companies hoping to take advantage of a potentially massive nascent market by using technology to make the process of building a brand and signing deals as simple and efficient as possible.

“You are going to need representation. And not only just any representation, but representation that actually cares about you,” Olson says. “… So what I’m doing now is I’ve created this company that, in my hopes, is to help give structure to individuals who want to speak, who are speaking, who don’t know how to represent themselves, who are kind of lost in this crazy landscape that is the engagement world.”

A labyrinth of differing and developing regulations that will shape the scope of what can be done makes the immediate future even more confusing for student-athletes, their schools and the companies hoping to hire them. Business owners, athletic department administrators and politicians believe that at least some degree of chaos is looming on the horizon. Olson says he’s not sure exactly what to expect this summer either, but he and his roommate-turned-business partner are among the very few (if not the only) people who can say they’ve lived through that chaos before.

At first, Hennes thought Olson was cracking a joke when he introduced himself in 2015 to the eight members of their dorm suite via email prior to freshman year at USC. Olson told them he was going to be on the top-10-ranked Trojans’ football roster as a reserve long-snapper, and that he was blind.

“I remember thinking, ‘OK, this kid is hilarious,'” Hennes says. It wasn’t until another roommate pointed out that it was unfair to make Olson chip in on the group’s television purchase that Hennes figured out Olson was being honest. “I was like, ‘Oh s—! That’s real? Are you kidding me?'”

Hennes then researched his new roommate and learned that Olson had permanently lost his eyesight when he was 12 years old after eight bouts with retinoblastoma cancer. Olson, who grew up a die-hard USC fan in Huntington Beach, became a regular fixture around the Trojans’ locker room as a child after then-head coach Pete Carroll heard about his medical condition. After Olson’s connection with the program and his upbeat attitude were featured in news stories, corporate groups started to invite him to share his inspirational journey as a paid public speaker while he was still in middle school.

Olson received a scholarship for disabled athletes after he was accepted to USC and was offered a chance to try out for the football team. When he and Hennes arrived on campus in 2015, Hennes was terrified that he would leave something out in the room that would trip Olson or commit some other sort of faux pas while learning to live with a blind person. He was also quick to see the power Olson’s story could have when combined with the platform provided by big-time college athletics.

Olson scoffed at his new roommate’s predictions of his impending fame. So during one of their first nights living in the dorm together, Hennes made Olson promise that if he landed in the spotlight that Hennes could lend a hand as his personal public relations manager. Olson didn’t expect anything to come from it, but within weeks of his first practice, USC had gathered a list of interview requests.

Because Olson had started his speaking career prior to becoming a college athlete, the NCAA granted him a rare waiver to ignore the amateurism rules prohibiting players from taking money from third-party sources. He was free to profit while he played. Olson’s parents had helped manage his speaking career while he was in high school, but starting in their second semester at USC, Hennes took over that role. He helped steer Olson to interviews, kept track of his calendar and organized a few paid speaking engagements during their first two years in school.

Their friendship and partnership reached new heights on Sept. 2, 2017, when Olson hit a milestone in his football career. USC pulled away from Western Michigan in the fourth quarter of its season opener that day, and a late interception returned for a touchdown provided a chance for Olson to take the field to snap for the extra point. His delivery was perfect. He was mobbed by teammates as the crowd chanted his name. Suddenly, a massive new wave of outsiders knew of Olson’s story. They all wanted to meet him.

“After I snapped, it definitely blew up,” Olson says. “It was incredible the amount of people who reached out.”

The following week, Olson and Hennes took a red-eye flight to New York City to appear on “Good Morning America,” daytime talk shows and a pre-production meeting for ESPN’s College GameDay in a 36-hour whirlwind before jetting back to Los Angeles for the Trojans’ next game. Olson remained steadily overwhelmed by trying to keep up with schoolwork, football practice and the increasing number of requests for his time.

“People were reaching out to Jake in 300 different ways,” Hennes says. “Someone wrote a letter to his house about booking him. Someone messaged his sister on Facebook. People reached out to USC. So the first thing we realized, there was no centralized hub to easily find and book Jake.”

Olson and Hennes thought there must be a better way. They had started to think about how to make the process more efficient when, months later, they received a request to speak to a Fresno-based business owned by an investor named John Shegerian. They met Shegerian at USC’s athletics dining hall to iron out details of Olson’s speaking appearance. The college juniors wore T-shirts and board shorts. Quebec, Olson’s guide dog, was nestled between his flip-flops.

They explained to the much-better-dressed Shegerian what a challenge it had been since September to manage Olson’s time. They told him they were trying to build an online platform to make it easier for companies to find and book interesting speakers. Shegerian thought they might be on to something. He offered the pair of 21-year-olds their first investment money and the technical assistance they would need to build their new company.

Olson and Hennes were attached at the hip for the final year of their college education as they worked together on Engage while Olson continued his career as an inspirational speaker. Hennes made sure Olson showed up on time for his fully packed schedule. Olson reminded his active friend to pace himself and occasionally eat a meal.

“He’s been a blessing in my life,” Olson says. “I cannot imagine going through college without Daniel. … He would be right there with me traveling to whatever state to speak at some random time. He would be there for me to help out with the business. I would never, ever, ever give advice to do it alone. I don’t think it’s possible to do it alone.”

Olson knows not everyone will have the same compelling life story and skill set that helped him hold down a career that netted him more than six figures’ worth of income during his time playing college sports. He believes, though, that thousands of athletes will soon have the opportunity to market themselves in a way that can at least make their lives a little easier in the short term if not fully changing them in the long term. He says it irked him that his teammates at USC couldn’t have the same chances he had while playing in college.

“What frustrated me is thinking about how other individuals were prohibited from telling their stories,” Olson says. “I can’t understand why a college athlete couldn’t go do the same thing. If they receive money for it, great. If they’re changing people’s lives, even better. I couldn’t understand. I’m not the only inspirational story. Literally, I had teammates of mine who inspired me; why can’t they go do the same thing?”

Olson is urging the athletes he speaks with to focus on monetizing their personal passions rather than signing up for whatever opportunities will put the most money in their bank account. Chasing money alone, he tells them, will lead to burnout and likely impact their performance in their sport or in the classroom. But, if managed properly, he believes the new doors being opened to college athletes this summer could have a huge positive impact. Olson says superstar athletes will have the chance to be as creative as they want to be and make substantial salaries from their NIL rights.

A player like Miami quarterback D’Eriq King — a Heisman candidate at a brand-name school — will have the chance to make more than $100,000 in his final year of college football, according to Olson and Hennes. King grew up in Houston and is the son of a breast cancer survivor. He said he’s eagerly awaiting the opportunity to do things like raise money for cancer research or return to his hometown to speak to kids or run football camps.

“Anything that can help other people get through to what they’re going through. That’s a really big deal to me,” King says. “Especially in my hometown, Houston, and Miami, my second home now, I would love the opportunity to talk to other people about my story.”

King said he and his teammates have been attending regular educational sessions set up for them by the athletic department this summer to learn about financial planning or marketing and hear from expert speakers in different fields. He said he knows it will be a challenge to balance business with an already busy agenda, but he believes he and many other players will have the support they need to turn these major changes into a positive and manageable experience.

“I think it might be a little bit of a challenge,” King says. “But I have a great support system in my family, great coaches around me, and a great support staff here at University of Miami. I think I’m ready for it.”

The top stars at the college level will likely sign with agents, which had been prohibited prior to this summer’s coming rule changes, to help them sort through deals that could reach well into the six-figure dollar range, if not higher. The majority of athletes won’t have agents or aggressive, energetic freshman roommates to shepherd them through this new landscape. Those athletes will rely largely on the bevy of tech-based companies built to simplify the process of finding endorsement opportunities.

Along with the ability to find speaking gigs on Engage, Hennes and Olson are expecting a lot of college athletes to use their site to arrange sweepstakes with fans — a service they’ve provided to pro athletes such as Terrell Owens, Chad Ochocinco Johnson and Isaac Bruce in the past. Fans bought $10 raffle tickets for the chance to spend a day with Owens in Miami prior to Super Bowl LIV. Bruce is currently using Engage to raffle off the chance to tag along with him for three days during his Hall of Fame induction ceremony this summer to help raise money for his charitable foundation.

Engage has grown its list of speakers who use the platform from 400 to 2,100 in the past year, and Hennes says this past June was the biggest month of revenue in the company’s history. Much of that growth has come from partnering with established agencies such as RocNation and Athletes First. Engage is in the process of raising $2 million in seed funding to expand.

Part of that funding will be used to add staff in an effort to gear up for the potential addition of thousands of college athletes to their platform this summer. Olson and Hennes believe that many NCAA athletes will be sought after to speak to local businesses or youth groups in their hometown communities or be able to host pop-up events to interact with fans near campus. Hennes said he has been speaking with current college athletes on a daily basis in the past month, counseling them on how to think about sharing their stories and talking through ways to approach the wide range of options that will soon be open to them.

Engage doesn’t exclusively represent the athletes who use their site or charge them money to use the platform. It generates a profit by charging an extra fee to companies who book speakers on its platform or a service fee to fans who buy raffle tickets for the events it puts together.

There are a variety of services and business models emerging in the industry. Some companies plan to help connect athletes and brands. Some are offering to help athletic departments keep track of their athletes’ deals. Others are offering to train schools and athletes on how to build market value while following the evolving rules and restrictions.

Some companies plan to take a percentage fee of deals completed on their platform. Others are selling their services directly to athletic departments who will in turn provide them to their athletes.

Industry leaders Opendorse and INFLCR have each partnered with dozens of major athletic programs in the past year such as Nebraska (where Opendorse’s founders previously played for the football team) and Kentucky (which was among the first clients to sign on with INFLCR). Many schools view branding tools and NIL opportunities as the next major battle in the recruiting arms race. On top of showing off sparkling new locker rooms to recruits, schools are now showing them the tools they can provide to help them improve their market value. Engage signed a partnership deal with Opendorse in June that will integrate the Engage platform into the other tools that Opendorse offers to its clients’ athletes.

Olson learned during his days at USC that opportunities to make money inevitably come with potential pitfalls as well.

“There are going to be a lot of sharks out there,” Olson says. “I think people need to understand that anytime there’s money involved, especially big money, there’s going to be people who want that money, who don’t care about you, but just care about the money.”

Olson managed to avoid any major mistakes while learning the industry in college, but says he knows of stories of talent being forced into deals that made them uncomfortable, agents lying about the amount of money in a deal and pocketing the difference, or agents locking clients into unfair, long-term contracts. Hennes said he already has heard from college athletes who have been contacted by self-proclaimed marketing experts offering them questionable loans or help in exchange for upfront payments.

Many colleges have set up educational training for their athletes in hopes of steering them away from these problems. Hennes has offered advice to the college athletes with whom he has been speaking.

“Right now the message is more, ‘This is going to be exciting. You need to be really careful right now. Nothing is certain. Be careful,'” Hennes says. “It’s more trying to educate them on what I know, even though no one knows anything for certain.”

The details of what deals athletes will be allowed to pursue differ based on the state where they play. NCAA rule changes that apply to the majority of states that don’t have laws scheduled to go into effect this summer could bring their own set of specific restrictions. And all of those nuances could shift and evolve in the coming months as Congress weighs its options in establishing a federal law to govern NIL opportunities.

Sorting through those rules is just one layer of the uncertainty that comes from opening a brand-new marketplace to hundreds of thousands of athletes during an age when social media and other technology are dramatically changing the way that any influencer can interact with fans and profit from his or her fame.

Olson says building a start-up company in that environment has at times felt just as challenging as being treated for childhood cancer or learning to play college football without being able to see.

“You don’t know what to expect. You’re doing it all for the first time. It’s hard,” he says. “It’s scary devoting your whole life toward something that you have no idea if it may or may not work out. And that takes a lot of courage. It’s the same thing, kind of, going through cancer, blindness. You have no idea how it’s going to work out.”

The floodgates of change are about to open for college athletes. Olson and other entrepreneurs like him say they’ve done their best to build products that will channel that deluge in the right direction. But no one, not even those who lived through it before, knows what comes next.