Legacy is a weighted word for the average 24-year old.
It connotes upholding the reputation of forebearers while carving out one’s own distinct chapter in history for future generations. In the NFL, it looks like retired jersey numbers, inductions into hallowed halls, and associations with phrases like “redefined the position” and “one of the greats.”
It’s a disorienting phenomenon created by the past, present, and future all at once. It’s a lot for an NFL rookie to think about, but D’Wayne Eskridge doesn’t hesitate.
After all, he isn’t exactly an average 24-year old. The intellectual athlete-entrepreneur is much more dynamic than that.
“I would say legacy means to me… That’s a pretty good question.” Eskridge laughs as he gathers his thoughts on the matter.
He then offers a perspective decades ahead of his time.
“I would say legacy is how you want to be remembered. When it’s all said and done, once I hang up the cleats, what do I want to be remembered as? And I would like that legacy to be that I’ve faced a lot of things, had to persevere through a lot of things to get to this point of making it to the NFL. So I want to be known as, I was one that came in and blossomed and I became a leader on whatever organization that I was a part of and inspired the youth, whoever that may be.”
“Keep the fires lit.” Eskridge laughs again, repeating a phrase that defined his interview. Passion, endurance, motivation, grit: these are the hallmarks of a great Seahawk in the making. With this mentality, Eskridge is determined to burn his name into the memory of every Seahawks fan. But the legacy Eskridge is forging off the field will have him remembered the way Walter Payton was.
The dictionary definition of “legacy” lists three primary interpretations: a gift bequeathed in a will, a mantle received from ancestors or predecessors, or a candidate for an organization that enjoys preferential status because of a relative’s affiliation. For D’Wayne, there is the legacy of the Eskridge clan that he has always carried with him, from Mississippi to Indiana to Seattle. There’s the legacy of who he is, shaped by the love of his family, the support of his mentors, and the chip on his shoulder that still burns from scorn.
Then there’s the legacy of Michael Ledo, nephew of the “godfather” of Black sports agents Eugene Parker. Parker’s success paved the way for Ledo’s intuition and intellect to flourish as an athlete-turned-entrepreneur. As a revered legacy member of the NFL agent world, Ledo embraced the legacy Parker left behind by building RISE, which develops a legacy strategy for athlete entrepreneurs.
In this way, Ledo lives out every inch of the legacy detailed in the dictionary — and because he has, D’Wayne Eskridge can now carve out his own.
When Eskridge was first drafted by the Seahawks, he re-shared a video on Twitter from RISE Sports Advisors. In it, he explains how his versatility translates to his investment strategy, with a specific interest in real estate.
He also responded to a prompt about what makes him dynamic. In his words, the silent leader who “observes, takes notes and applies it to [himself]” is also an avid fishing and culinary enthusiast.
“My enterprise is going to have a variety to it,” he grins to the audience.
What Eskridge’s enterprise is at this point is something that’s in the capable hands of RISE Sports Advisors.
According to Michael Ledo, the founder and CEO of RISE, it is “a multi-family office that serves athlete entrepreneurs.”
The concept of RISE is unique because it’s still relatively uncommon in the sports world. There are sports agents who negotiate million-dollar contracts, and there are business advisors who preside over portfolio investments. But there’s really no one trying to help athletes become entrepreneurs themselves, giving them the tools to become successful businessmen during and after their NFL careers. In their own words, the company is “more dedicated than consultants, and more strategic than wealth managers” as they work with clients to “craft bespoke strategies that achieve their ambitions, now and far into the future.”
“We help them develop a legacy strategy,” Ledo explained. “We give them access to an exclusive network and deal flow and then we focus on accelerating wealth and protection, so CFO services.”
Terms like “deal flow” and “wealth protection” are common in the finance world, but not in the football one. That’s why the well-connected firm collaborates with financial savants to turn multi-million dollar NFL contracts into startup company shares and charitable foundations.
“We have an integrated family office, and we work with some of the best accountants, investment managers and private banks — all the different people in our network — to really provide our clients with comprehensive and collaborative resources so that they can build an “athlete enterprise” as we call it.”
Already, the company has an athlete enterprise value of $15 million and a private deal flow of $12 billion, averaging an equity multiple of two. Eskridge signed a four-year, $5,953,504 contract with the Seahawks, and with the guidance of RISE advisors and affiliates, he could invest and expand that rookie contract into something that would last generations.
“We don’t want them to get to a place where later, after they amass a certain amount of wealth, it’s like, ‘What now?'” Ledo said. “We’ve already got a solid foundation, we build a plan and a strategy and we follow it.”
The misconception that NFL millionaires have enough money to last a lifetime is a dangerous one — for many athletes, that “what now?” moment happens far too late.
In 2017, former Steelers and Giants receiver Plaxico Burress penned a letter to the 2017 Draft Class, warning them with the cautionary tale of his own mistakes.
After two years in prison and losing millions of dollars, Burress admits that he could have made smarter decisions early on that would have saved him from personal and financial losses, writing, “I can live with having lost some money because I trusted the wrong people, or because I wasn’t educated enough on how money and business worked.”
While this is the worst-case scenario, there are current and former athletes who have found ways to maximize their earnings. Perhaps the best examples are found in the NBA, where icons like Michael Jordan, Kobe Bryant, and LeBron James are widely recognized for their off-court ventures.
LeBron James has earned $200 million over a 17-year NBA career, yet his net worth is $450 million — more than doubled due to savvy financial investments. His diverse portfolio includes 14 Blaze Pizza franchises, a $1 billion Nike “lifetime deal,” stock in Beats Electronics and Liverpool F.C. and ownership of his production company, SpringHill Entertainment. James also co-founded media company Uninterrupted and hosts HBO’s “The Shop,” a barbershop-style show that reflects his personality.
It all builds into LeBron’s brand, the popular buzzword that most athletes are familiar with in the social media age. Back in 2014, then-Giants receiver Odell Beckham Jr. capitalized on his famous one-handed catch in an especially lucrative New York market. Three years later, he signed a record-breaking deal with Nike worth over $29 million. Beckham Jr. expressed his desire to become a “brand icon” for the apparel company, but he has failed to capitalize on those 2014 expectations. Appearing in seven games last year for the Browns due to injury, Beckham Jr. caught half of his targets for a meager 319 yards. As JuJu Smith-Schuster proved during the 2020 AFC Divisional Playoffs, branding based solely on athletic ability can limit athlete entrepreneurs when they wipe out on the field.
“I think what my clients do and what people say when they say that are probably two different things,” Ledo said when speaking about the perception of the athlete entrepreneur. “Most athletes, you know, they’re really caught up in this “brand” thing, and they wanna build their brand, build their brand, but a brand is authentic. Like, a brand is about, ‘Who are you?’
It really comes down to what’s their passion, what’s their interest, what’s their why, what drives them. When we get with D’Wayne Eskridge and we build a brand, we’re not trying to tell the Seattle market that he’s somebody he’s not. We’re trying to illuminate and project who he is.”
For Ledo, his personal brand has been an athlete’s dedicated mindset applied to the world of business. The Indiana native was a decorated high school and college athlete at the University of Saint Francis in Fort Wayne, Indiana. The 2006 business graduate then focused on athlete development by co-founding Athletes With Purpose. The elite multi-sport training program began as a seasonal program with “a vision to develop athletes mentally, spiritually and emotionally.” Since graduating, Ledo has been focused on how he can fortify the character of young, dedicated athletes.
“[AWP Chief Performance Officer Bryan Bourcier] and I are strong men of faith, and saw an issue with character versus talent,” Ledo said in a 2012 USF alumni interview. “Talent can only take you so far, but character sustains you. We decided to develop athletes with purpose.”
Through building a premier athletic training facility in the Midwest, Ledo has trained a number of athletes who ended up in the NFL, including RISE clients like Cowboys linebacker Jaylon Smith and Eskridge. Ledo eventually sold AWP in order to focus on entrepreneurial development with RISE. The trust he built leading those athletes to success is why many RISE clients have known Ledo for years, including Eskridge.
“A lot of guys from that Indiana area trained in my company, so he knew me, and Dee was a part of my National Championship 7-on-7 team,” Ledo said. “He played with about five other guys that are in the NFL that were on that team. We had a strong relationship and those guys trusted me, and I think a lot of those guys have seen the great work that we’ve been doing with Jaylon Smith and now Jessie Bates and Jordan Fuller and so on and so forth, so they saw the work.
We talked, and like when I talk to any guy, it’s all about fit and alignment. The first thing when I meet with a guy, I’m like, ‘Hey, do you want to be an entrepreneur? Are you interested in learning? Is this something that’s a good fit for you, or do you just want to ball and then put your money away and just hope?’ And Dee was really interested.”
Eskridge remembers how he started training with Ledo at AWP. Back then, he was a running back at tiny Bluffton High School looking to better his game.
“Once he branched off to RISE, I always wanted to be a part of that because of knowing Mike Ledo and some of the clients that he had,” Eskridge said. “I looked up to Jaylon Smith and some of those guys. I was always in contact with [Ledo], trying to learn something, be able to get on board with them.”
During his junior year at Western Michigan, he started communicating more frequently with Ledo in anticipation of joining RISE. As a senior, he finally got a chance to sign with the company, but his entrepreneurial aspirations existed long before then.
“I wanted to do something different when it came to business,” Eskridge said. “Since I was younger, I’ve always wanted to have my own training facility, kind of like AWP. I remember thinking my first time going to AWP, ‘I kind of want something like this later on in life.’ So that kind of sparked that then, and I’ve always been just thinking about business. I didn’t really know too much, but now, I’ve been getting educated on it the last couple years. I think I’ve always had it in me just kind of pulling it out now at this point.”
At RISE, Ledo says that they serve two kinds of athletes: the ambitious visionary and the humble apprentice.
Those who fall into the humble apprentice category aren’t as ambitious about expansive financial strategy, foregoing lofty annual benchmarks for the opportunity to gain financial wisdom.
Then there are those who have more ideas than they know what to do with — those are the ambitious visionaries. For these entrepreneurs, Ledo and his team seek to protect their intellectual property and investments, providing the strategy and advice that help them to realize their goals.
So, which one is Eskridge?
“Oh, D’Wayne,” Ledo mused. “Oof… Well… D’Wayne’s probably…” He pauses for several seconds while he determines which category the young wideout falls into.
“Man, D’Wayne’s amazing,” he finally effuses. “D’Wayne’s probably in the middle. I know that’s a cop-out, but he’s so humble, and he’s such a learner, man, like, he just has a different spirit.
Most people don’t know what they don’t know, their egos are kind of like, ‘I know this, I got this.’ D’Wayne knows, like, ‘Man, I don’t understand how to read financial projections right now, Mike, I don’t understand.’ And it’s that humility that makes him a good student and a good learner. He’s so comfortable in his skin that he’s not out here trying to impress people or trying to pretend to be somebody that he’s not.
I’d say D’Wayne’s got that side, but then D’Wayne’s got some vision, like D’Wayne wants to do big things. And D’Wayne’s girlfriend, who is an amazing young woman — she’s definitely pushing him forward in life — she has some vision. Between the two of them, they’ve got some ambitious visionary, but then they’re very humble and it allows them to learn, too.”
Embodying the humble apprentice and ambitious visionary demonstrates Eskridge’s defining characteristic: his versatility. A player who has played running back, cornerback, kick returner, and wide receiver, Ledo has found the perfect way to brand the do-it-all receiver to encapsulate his persona.
“The way we’re branding Dee is he’s a silent leader, but he’s dynamic, so we call him ‘Dynamic Dee.’ And what we say is that he’s dynamic on the field and he’s going to be dynamic off the field, but he’s a silent leader.”
“He’s a silent leader; he’s a country boy,” Ledo continued. “He’s a throwback kind of guy. Just a real, laid-back competitor.”
Eskridge explained how “Dynamic Dee” came to be around a roundtable at RISE.
“When we were building up my core values, it was bringing everything out and putting it on the whiteboard,” he said. “’Dynamic’ came up a lot within the table of trustees, because of how I am: dynamic on the field, I can play multiple positions often and these things, and then I’m also dynamic outside of the field when it comes to my interest and what I want to do with my life. When it comes to fishing, cooking, it’s very dynamic, it’s not just in stone — you’ve got to guess what I’m about. We felt like ‘dynamic’ was the perfect word.”
It’s the way that everyone close to Eskridge perceives him, but the truth is that the Dynamic Dee brand is still relatively under wraps at this point. Between rookie minicamp and an interview with Seahawk Maven, Eskridge mentioned having a critical brand meeting later that day.
“That’s the most growth that I need to acquire is a social media presence because I’ve got to learn a lot more about it,” Eskridge said. “I don’t really utilize that at the moment, so ‘Dynamic Dee’ hasn’t even got across the internet just yet, it’s kind of just within RISE and my family that knows about ‘Dynamic Dee.’”
As far as the “silent leader” branding goes, there’s already a template that Eskridge can adapt to suit his own distinct traits. Ledo often compares the wideout to another silent leader whose style was widely admired in Seattle: Marshawn Lynch.
“Dee’s not much of a talker,” Ledo said. “He’ll answer questions and say stuff and get to the point, but when he says things, it’s going to be meaningful. He doesn’t do fluff conversations and that kind of thing. And I just think he’s a natural leader. I think people gravitate to him because he’s about action, he’s not about words and status. It’s like people, they feel the authenticity and the realness. Dee’s a real dude, so when people are around him, you can just see that, and then people gravitate to that realness.”
Eskridge appreciates the comparison drawn between himself and one of his favorite running backs.
“Yeah, [Ledo] mentioned that to me as well when it comes to kind of the mindsets, when it comes to being eager to learn,” Eskridge said. “I’m always open to different things. And I haven’t met him, I look forward to meeting Marshawn Lynch in the future. But he definitely explained it to me a little bit, so I think I think it’d be a good relationship built once it comes down to it.”
Lynch’s most recent business venture embodies all that the iconic running back represents: a jovial spirit who is deeply committed to his community.
In February 2021, Lynch launched Dodi Blunts, Oakland’s “premier craft blunt” that is infused with 24K diamonds. Profits from the luxury blunts serve a higher purpose: to combat the trauma inflicted by the war on drugs.
“We are devoted to getting social equity “right” and creating opportunities that The War on Drugs annihilated for Black and Brown people,” reads the company’s website. “ESPECIALLY in Oaktown.” To accomplish that, Dodi Blunts partnered with The Last Prisoner Project, a Bay Area non-profit dedicated to cannabis-related criminal justice reform.
Long a fan of the Beast Quake creator, Eskridge admires Lynch for the entrepreneurial decisions he’s made over the course of his career and beyond.
“I really like Marshawn Lynch, or Beast Mode, ever since I was younger, he’s one of my favorite running backs,” Eskridge said. “And then on his business side, you’re seeing him be an entrepreneur and be able to change the chance his community has and really change his family’s generational wealth. I admire that, and I want to apply that to my journey.”
Eskridge also admires LeBron James and the late Kobe Bryant, athlete entrepreneurs who have excelled on and off the court.
“I just try to take a little bit from the greats and apply it to my life,” he added.
It’s still early in his journey, so there’s not much that can be revealed about Eskridge’s financial projections and investments. But getting to know “Dynamic Dee” on a deeper level has left Ledo in awe of the young receiver’s spirit.
“Aw, man,” Ledo exclaimed. “It’s cool, because he’s still trying to learn. You know, young guys, what we do is we expose them. We expose them to multi, multi-millionaires, sometimes billionaires, people in the business realm who are extremely successful. And I think that if Dee gets exposed, he’s gonna continually wanna learn more, but the biggest thing I’ve learned is, you know, how he wants to help his hometown in Mississippi where he’s from, he’s from a small town out there, and he really wants to kind of be a beacon of light in that community.
Getting to meet his family from the Mississippi/Arkansas areas at the draft and really knowing how he wants to elevate and lift his family, but we’ve got to first take care of him, right? And we’ve got to first make sure that he understands what’s going on and he’s secure and things are good and lay a good foundation so that he’s able to help others. I think the biggest thing I’ve learned with Dee this far is just how good his heart is, how pure he is. He’s so respectful, even when he talks to me, it’s always, ‘Yes, sir,’ all that kind of thing. I just believe humility takes people a long way.”
Investing In Eskridge
Humility has ultimately taken Eskridge to his dream destination as an explosive receiver prospect coveted by Seattle’s brain trust of John Schneider and Pete Carroll.
But Eskridge’s humble roots stretch all the way back to Winona, Mississippi, where he was born and lived until the end of kindergarten. His family then moved to the Fort Wayne area in northern Indiana, where Eskridge would grow up as an all-state athlete. Training at the AWP facility, Eskridge developed into a state track star and running back at Bluffton High School and eventually signed a letter of intent to play college ball at Western Michigan. But long before then, the first significant race Eskridge won was against Aesop’s fabled hare.
“That is where the speed comes from,” writes sports journalist Tyler Dunne in a pre-draft profile on Eskridge. “The day he spotted a rabbit in a neighbor’s yard at nine years old.”
“One day, we were just walking and I saw a rabbit,” Eskridge says. “It didn’t really run away from us instantly. So, I just snuck up on him a little bit and moved kind of slowly. And then the rabbit ran straight so as soon as I saw that, I ran and literally picked the rabbit up. Like I cornered it and caught the rabbit.”
Those are the kinds of afternoons Eskridge remembers from his childhood, playing outside with his brother every single day.
“It was me, I have a brother that is two years younger than me, and then I have two other siblings that I lived with at the time,” Eskridge said when describing his youth. “And it was just our mother, so you know, we were always the kids that found something to do out of nothing, especially with my brother. We were just outside until we couldn’t be outside anymore, and we were always finding something to do, inside or outside.”
On Instagram, Eskridge has a highlight tab titled, “Good brotha.” In it, Eskridge replays a season-ending injury he incurred against Syracuse in 2019.
“I do this, so my siblings don’t have to go as hard as I go,” Eskridge wrote.
During his draft day party, family members gathered round in custom-made “DeeWay” jerseys, a play on the popular Subway logo. At the end of an Instagram post, Eskridge gives a rousing speech to his loved ones as he toasts his success to them and their collective future.
“Listen, it’s been a long road,” Eskridge began. “But listen, everybody said it’s for a reason, and the love that’s going around, that’s something that’s gonna mean something to me more than anything I accomplish. There’s nothing like a family that sticks together, there’s always ups and downs, but at the end of the day, we’ve got to stick together. There’s something way deeper than this, we’ve got young ones coming up, and we’ve got to be the best us at the end of the day. That’s what I’m introducing: elevation. I love everybody that’s here right now and I appreciate y’all more than y’all know.”
With Eskridge, contributing to his family’s legacy is something that has been on the receiver’s mind for some time. Ten miles outside of Winona, Mississippi is Eskridge, where D’Wayne has recently traced his heritage.
“I’ve learned a little bit more about the history of it, but there’s a certain part down there about 20 minutes outside of Winona that’s called Eskridge, Mississippi and I think that’s where a lot of our heroes came from and stuff like that,” Eskridge said. “So it’s interesting, I got to see it for the first time I believe last year.”
“I grew up mostly in Indiana, so it was just going back and forth with family. This time, I really wanted to see something kind of where we came from a little bit more. So then I just asked around the family, and we set something up. Then I went out there to see the Eskridge Church and the Eskridge Road and all that type of stuff, so it was pretty cool.”
Eskridge’s visit to his namesake Mississippi town inspired him, molding his investment goals with RISE. He wants to tackle poverty and discrimination by fighting gentrification, a phenomenon that has historically ousted Black families by driving up real estate prices.
“Right now we’re building the foundation when it comes to the money and the resources that I have right now to be able to set something up for Year Two or Three to where I invest in exactly what I want to,” Eskridge elaborated. “I’m really big into real estate, I want to use that platform to be able to… I’m still thinking about it, but I really want to, like, the gentrification and the inflation stuff, that doesn’t sit well with me. I want to be in a position to be able to kind of give back in that aspect in my hometown to Indiana and hometown of Mississippi. To be able to give homes to the community, instead of pushing them out, so you know that’s the biggest thing that’s on my list for the future.”
“I just feel like the communities are built on the cultures that have been there,” he continued. “There’s nothing wrong with people having a lot of money, but I feel like there’s ways to do things, and pushing out the people that are the core community people, that just doesn’t sit well with me. It’s good to be able to put homes in the community, but the prices are just ridiculous, so in any type of way, try to be able to affect that in a positive way, as I can.”
Eskridge is already thinking like Lynch, imagining ways he can use his success to uplift his local community in Mississippi and Indiana. As Ledo mentioned, RISE is dedicated not only to developing Eskridge’s goals, but to make sure that he can financially sustain them and see these passionate projects through.
“I’m blueprinting it right now to be able to, because at the end of the day, I’ve got to have the resources to be able to keep it going. I don’t want to just start something and then it comes to an abrupt halt just because of the resources, so there’s going to be a lot more planning that goes into that to see if that’s even possible. I know if there’s a will, there’s a way, so I’m going to find a way, but it’s going to take some time.”
The blueprint for RISE athlete entrepreneurs has predominantly been laid out by Jaylon Smith, who also heralded from the Fort Wayne area. Smith has been the subject of several in-depth feature stories, many of which also detail his own relationship with Ledo as a mentor and advisor.
Entering his sixth NFL season, Smith has established an entrepreneurial profile that reflects passion, creativity, intuition about future markets, and the desire to uplift others.
“Jaylon’s biggest projects? Oh, Lord,” Ledo says when asked to summarize what the 2019 Pro Bowler has been up to in recent years.
“Well, the Minority Entrepreneur Institute (MEI) is huge, it’s why he was nominated for the Walter Payton Man of the Year [Award]. That is focused on closing the educational and economic gap for minority entrepreneurs, so we hosted a showcase, which is a pitch competition, in Indiana two years ago and raised $200,000.”
“Last year, during the pandemic — during the pandemic, by the way —we went to Dallas, TX and we raised $600,000. So right now, we’ve got 8 companies in our portfolio that we’ve invested $800,000 in Latinx, Black and female companies. We’re hosting our third showcase in Tampa, FL this July 9th, and so that’s the focus, to provide minorities with the resources on strategy, the same way we do with our athletes, and then also financial capital and creating a marketplace that minorities know that when they’re looking for opportunities, they’ve got somewhere they can go, so I think that’s Jaylon’s really big deal.”
MEI is Smith’s brainchild that was born out of the RISE boardroom, but it’s only one project in Smith’s ambitious portfolio.
“He’s an equity partner for iCryo Recovery & Wellness, which is a recovery and wellness center focused on cryotherapy out of Houston,” Ledo said. “He’s big in that, he owns a location in his hometown in Indiana, he’s getting ready to open a couple more in Indiana, so he’s expanding the business there.”
Smith started an eyewear company called CEV Collections, a reference to Smith’s catchphrase, Clear Eye View. Ledo said that the eyewear company is enjoying growth and expansion that’s set to release important news in the near future. Additionally, Smith owns six real estate projects that include multi-family housing units, as well as stake in a distillery company.
“Regardless of what happens in football, he’s set for the rest of his life. We know he wants to do a lot more. Obviously, football is his main thing, he’s focused on that game.”
“A lot of people ask, ‘Well how can he do all that and play football; he’s not focused!’ Oh, believe me, he’s focused we’re working over here on our end to make sure all those things are operating while he’s focused on football. It’s just that the infrastructure and the support system that he has is different than most of his peers in football.”
Smith was Ledo’s first client, but since then, the company has expanded to accommodate seven athlete enterprises. Bengals safety Jessie Bates III is about to finish his rookie contract, and because he’s developed a solid, low-maintenance financial plan over the past three years, he’ll be fully prepared to launch into his entrepreneurial goals if he indeed becomes one of the NFL’s highest-paid safeties. With everything set in place, Bates will finally be able to expand his Single Mother’s Initiative, which was created to help mothers like his own cope with the difficulties of single parenthood.
Another RISE client, Drue Tranquill, is also laying the groundwork during his rookie contract. Tranquill hosts The Drue Tranquill Podcast, which features motivational interviews with athletic, financial, faith and academic leaders so that listeners can “optimize their performance and maximize their God-given potential.”
It seems that everyone at RISE dreams of an entrepreneurship that not only creates wealth for one individual, but creates a wealth of opportunity, experience and community by financing initiatives for their own. Austin Mack was an undrafted wide receiver picked up by the New York Giants in 2020. When Biden signed a law recognizing Juneteenth as a national holiday, Mack responded with Mack Festival in Fort Wayne, which “seeks to bring unity to the city on Juneteenth.”
Unsurprisingly, Smith and Bates were in attendance to support their fellow player, entrepreneur and social justice advocate.
Before the NFL, out of the spotlight of the field, what matters most to Eskridge and his RISE brethren is ultimately family. Whether it’s by blood in Mississippi hometowns, by shared life experiences like single parenthood, or shared dreams like minority entrepreneurship, all of these athletes are creating legacies that are much bigger than themselves. All Ledo aims to do is ensure those lifelong dreams outside of football become an everlasting reality.
“What we’re doing at RISE is we’re creating a culture, an environment, where like minds attract like minds,” Ledo said. “D’Wayne can look at Jaylon, Jaylon can look at Jessie, and they can see it all. They think there’s a standard that is set that they live by, and they hold each other accountable. That’s the only way we’re going to change legacies and create generational wealth. We can’t change that without changing behavior. When guys talk about having money problems or they’ve got behavioral problems, we try to change the behavior, change the mindset, so that we can change the direction of their families.”
Keeping The Fires Lit
In college, Eskridge taped a list of things people had said about him in order to stay motivated. The feedback wasn’t too positive.
Too small. Kid from small school; can’t play D1. Getting hurt too much and can’t take hits. They even said he should have run track instead of playing football.
Eskridge took all the things he heard before setting foot into Western Michigan’s locker room and posted it on the first day he arrived. He stared at it every day as he suited up however his team needed him: as a kick returner, a cornerback, a receiver.
And he proved any detractors wrong. Breaking out as a senior in 2020, Eskridge led all Division I receivers in all-purpose yards per game (213) and finished with 768 receiving yards and eight touchdowns in just six games.
Despite this, he was still dismissed leading up to the draft, primarily because of his size. But that wasn’t a deterrent to Seattle, where small receivers have thrived in recent years. Doug Baldwin is 5-foot-10. Tyler Lockett is 5-foot-10. Eskridge is 5-foot-9. In a game of inches, people still seem to think that height is the determining factor in greatness. Yet the athletes dismissed for physical superficialities are often the ones that redefine the sport, carving out new roles for how the game can be played. For Eskridge, it’s playing hard, fast, and with a chip on his shoulder.
“It’s one thing to say who you are, and then it’s another to be able to show people who you are with that conversation how you attack this and I feel like that’s me. So all those things that I wrote on that paper that was a strength-building exercise, it’s a visual for me to be able to deal with something on a daily basis. I was keeping that chip on my shoulder, no matter what.”
The chip-on-shoulder mentality is almost necessary to stay competitive in the NFL. Ignoring the threat of injury, complacency can throw anyone off their game. And when the praise starts to roll in for those who were underestimated, staying humble is key. The “compliments” Eskridge taped to his locker in college complemented his game, and even though Seattle took him with the 56th pick, he remembers those who had him going much, much later.
“I don’t really often think about getting drafted in the second round, because when I look at this, last year, they had me rated to go in the seventh round and undrafted,” he said. “Just having that in the back of my head always allows me to push forward and not get comfortable in any situation that I’m in.”
Even though the Seahawks already had one of NFL’s most dangerous receiver duos, Eskridge offers an edge with explosive quickness, razor-sharp route-running, and electrifying kick return performances. But Seahawks scouts have known that since Eskridge’s Senior Bowl performance, says Ledo. He would know: his second cousin just so happens to be a team scout.
“I heard several scouts that I know, and guys were liking him,” Ledo said. “I think they talk to so many kids and they’re phony or they’re putting on their interview faces and doing all this, and D’Wayne’s just real.”
“When I used to talk to my cousin Jason, he was like, ‘Hey man, I love this dude, we love him.’ And Dee’s just Tyreek 2.0. He’s a fierce competitor, he’s a lot faster than what he ran in his 40, he’s a real high 4.2 guy. He ran a 4.38, he’s way faster than that. You can just see it in his play. If you look at the Seahawks, they’ve got Russell Wilson, they’ve got DK Metcalf, and then you got Tyler Lockett, and you throw Dee in the mix [whistles teeth], that’s just gonna be hard to defend. I think Russell’s going to be happy as long as he can get some protection.”
Eskridge agrees, saying catching targets from Wilson alongside Metcalf and Lockett creates an unmatched “explosiveness.”
“I’m just feeding off of those guys: that’s their room, and I’m the guy that’s coming in,” Eskridge said. He looks forward to adding to that as a leader himself, guaranteeing that “there’s big things coming in the future, most definitely.”
Before the draft, Eskridge felt that Seattle was the perfect fit. He even tweeted it into existence.
“It’s been great,” Eskridge said about his experience so far in Seattle. “This is definitely a winning and competitive culture. That’s who I am as well, so just being able to get with and converse with the guys, everybody’s pretty much on the same page. Everybody gets along with each other around here, and I think that’s the best thing about it.”
Hearing Eskridge describe the Seattle environment sounds similar to his college one. In a Player’s Tribune tweet, he listed his favorite video game as “Fuzion Frenzy.” Released in 2001, it’s an unusual choice for athletes who often mention Madden, NBA 2K, or any variety of contemporary games on the market.
Eskridge and his college roommates created a game out of the game. They played the mini-games for a tournament to determine the ultimate winner. The winner emerged victorious, and the losers? They had to belt out 50 pushups.
For those familiar with the game, Eskridge’s favorites were “the one where you had to get as many orbs as you can” and “the boat one.” It’s no surprise that he usually wasn’t the one belting out pushups.
“Oh, pretty often,” he laughed when asked how frequently he won. “I got good at it at a point in time, but then I didn’t last for too long with my roommates, so we were just going back and forth.”
Even his favorite video game speaks to the kind of person “Dynamic Dee” is. “Fuzion Frenzy” appealed to the competitive, fun-loving Western Michigan Broncos who grabbed the controllers every day after practice. It’s the best quality Eskridge has to offer to his new team.
“I would say dynamic,” he laughed when asked about the primary skill he brings to the team. “It’s how I attack the game, the mentality that I have at receiver, and also on special teams as well. And I think that’s gonna allow me to last in this game.”
The team that sprung for Jamal Adams, a strong safety like no other, has long demonstrated their appreciation for versatility.
“I feel like just as a whole, the Seahawks kind of just utilize what’s there, they want to take it to another level,” Eskridge said. “This is a championship culture, so they’re obviously going to put different pieces in different ways that maybe other teams wouldn’t, just because there’s that risk. I look forward to playing multiple positions with the Seahawks wherever I could be utilized to help us get to that championship. Right now, I’m playing receiver and doing some special team stuff, but I would imagine that it would open up sometime in the future.”
When Ledo first met Eskridge in high school, he was a running back. That first position has always been how Eskridge views himself in the game, and Ledo imagines how the Seahawks could use him as one.
“If you ask Dee, he thinks his original position is running back,” Ledo said. “I used to train Dee as a running back way back when I was doing that stuff. Dee is just dynamic in any way, like he just feels like if he touches the ball, I can see him getting tosses or jet sweeps. I mean, like if he comes in motion and they pretend like they’re gonna give him a jet sweep, the defense is gonna have to adjust to him doing that because if he gets the ball and he’s on a jet sweep, the linebacker ain’t catching him. I could see him doing that, and kickoff return, no question. I mean, you just want to put the ball in his hands in the dude’s hands and let him do his thing. For him, it’s just staying healthy and knowing the playbook.”
That’s something that Eskridge is also mindful of. Making it to the NFL is one thing, but staying in the league is something only a few men are lucky enough to accomplish. Not grasping the playbook is a quick ticket to a pink slip and getting injured can derail a career instantly. Not all of that is in Eskridge’s control, but the preventive measures that have allowed his talent to flourish are what he’s taking with him.
“I’m just sticking to the things that got me to this point,” he said. “When it comes to my routines, how I attack the playbook and really taking care of my body. That’s my temple now, and that’s what’s gonna get me paid. Always having those three fires lit, that will keep me going where I want to go.”
“Keeping the fires lit” compliments another phrase Eskridge picked up from wide receivers coach Greg Harbaugh Jr. at Western Michigan: “never arriving.”
“It means you’re always attacking, never arriving,” Eskridge explained. “Wherever you’re going, there’s always something next you’ve got to get to, so you’ve got to constantly, constantly keep going.”
Eskridge replays these mantras in his head as he goes through his practices, his games, and his life outside the stadium. While he is always looking to better his game, he is keen to hold onto everything that got him to this point.
“The best advice that I’ve heard is really just sticking to the foundation that I built,” he said. “I got here for a reason off of the things that I was doing, you know, so there’s not really certain things that I have to adapt to change where I’m at. Staying on my routines, Staying on just my mental part…They just said, ‘Keep being you, you will be successful.”
Ledo believes that as well. He imagines a bright future for the rookie, complete with a Pro Bowl nomination.
“I’m an under-promise/over-deliver kind of guy, but I think Dee could be a Pro Bowler,” he said. “Playing with Russell Wilson, I think that, just like Russell mentored DK Metcalf, there’s so much he’s going to learn from him so quickly. Whenever you play with — he’s never played with a quarterback like this — I think it’s just going to accelerate his understanding of the game.”
Dee physically can match up with anybody. So it’s not a physical thing—it’s how quick can he learn and understand it and get experience, and you’ve got a quarterback like this? It’s just going to accelerate it, so I think the sky’s the limit. He has to stay healthy, but we talked late last night, and he was like, ‘Man, I love Seattle, I love Coach Carroll and the environment,’ and I said, ‘Everybody does, bro.’ Everybody in Seattle just loves the energy, the vibe. It just seems like he’s a player’s coach and all that stuff.
I think Dee’s just excited to compete. He doesn’t have any entitlement, like, ‘Oh, I’m this.’ He’s going to earn everything that he wants, so I think he’s going to do very, very well on the field. And I know for a fact because of what we do that he’s going to make an impact in the community as well.”
When asked about Eskridge’s future with RISE, both he and Ledo give the same answer: the next big thing is their 2021 Athlete Enterprise Virtual Symposium. Taking place on June 23 and 24, it’s a free event that college and professional athletes can join virtually. The RISE Dallas headquarters will be safely hosting a private watch party, but the virtual event is convenient for those who are at camp, in quarantine or simply want to learn more about the organization. The lineup features professional athletes who have gone on to become CEOs and venture capitalists who want to offer financial wisdom to the next generation.
Last year featured Brent Jones, a three-time Super Bowl champion tight end who played with Joe Montana. After retiring in 2000, Jones connected with former teammates Steve Young, Tommy Vardell, and Mark Harris to co-found Northgate Capital, a venture capital and private equity firm investment firm. Although he ultimately sold his shares, the firm currently has $4.9 billion of assets under management.
This year’s speaker is another legendary San Francisco connection in Montana, an entrepreneur whose resume includes creating a bottle of his own Cabernet called Montagia. Montana will be in Dallas with the RISE crew as they kick off two days of intense learning and growth.
With the symposium, rookies like Eskridge get to learn from the greatest to ever play the game. And then there’s the other game — the financial one — that those athletes with enterprising entrepreneurial spirits finally have access to. The boardroom doors have opened, allowing those who have always dreamed of having it all to give it back to those they cherish the most.
“That’d be great to hear his insight,” Eskridge said about hearing from Joe Montana at the symposium. Ever the humble apprentice, he said that he’s “just looking to learn.”
“Learn something that allows me to see something differently or be able to guide my way through a business or an investment or real estate, whatever it may be.”
The legacy strategy is already a success. And because of Michael Ledo’s legacy, D’Wayne Eskridge finally has the chance to define his own.