How NFL Contracts Are Made with Disruptive Sports Agency

Summary

Podcast Summary: Stay Tranquilo – “How NFL Contracts Are Made with Disruptive Sports Agency”
Host: Stay Tranquilo Network
Guests: Henry Oregon (Agent & Co-founder, Disruptive Sports Agency), “Big Al” (Agent/Former Coach), and team
Date: March 2, 2026
Location: Super Bowl Media Row

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Episode Overview

This lively episode features a behind-the-scenes look at how NFL contracts are negotiated, the evolving world of athlete and coach representation, and the impact of NIL (Name, Image, Likeness) on college athletics. Henry Oregon and “Big Al” from Disruptive Sports Agency, known for their candid approach and player-first ethos, share personal stories, insights, and advice for navigating today’s high-stakes sports landscape. The conversation highlights the vital role of mentorship, being honest with clients, and empowering athletes for life beyond the game, all delivered with Stay Tranquilo’s signature warmth and humor.

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Key Discussion Points & Insights

1. Origins and Mission of Disruptive Sports Agency

• Henry Oregon’s Journey (00:35)
  • Started in football brand marketing at Nike.
  • Switched to agency work, influenced by mentor Aaron Goodwin (“the original godfather of black agents”).
  • Passion for football, learned from legends, and commitment to “staying in his lane.”

    “Aaron Goodwin also represented LeBron James and taught Rich everything he knows. I'll say it on camera.” – Henry (00:49)

• Big Al’s Background (01:09)
  • College football player, transitioned to coaching for a decade (JUCO, D1).
  • Mentored by Henry, co-founded coaches division representing ~100 football coaches and front-office execs.
• Relationship Origins (01:44)
  • Lifelong friends from youth football, playful banter about early athletic encounters.

2. The Coaching & Free Agency Carousel

• Insights on the Coaching Market (02:33)
  • 2024–25 was a particularly wild cycle with a “domino effect,” driven by relationships and timing over stats.

    “Carousels are like TLC reality shows, man. Cause you're waiting on a call that you may never get. It's all connections.” – Big Al (04:03)

  • Comparison between coach and player free agency: more drama and unpredictability among coaches.
• NIL’s Growing Role (05:14)
  • NIL changes the game – College athletes face tough choices between lucrative college deals and the NFL.

    “I advise all college players to have an NFL agent—not just your uncle, cousin or NIL master. There are guarantees and stipulations. You may not get that million dollars.” – Henry (05:14)

  • No hard metric for coaches outside W/L records; player tape trumps everything for NFL prospects.

3. Strategic Decisions: Staying or Going Pro (06:09)

• Discussion about Oregon’s quarterback choosing to play another year in college, even as a projected top pick.

  “It’s not just he’s going back to school to win. He’s going back to school so he can become a better pro and develop.” – Henry (06:47)

• The impact of team fit on draft decisions, including jokes about NFL team cultures (Dolphins/Jets banter).

4. Responsibilities During Super Bowl Week

• Disruptive athletes (e.g., George Holani) feature in the big game.

  “Don’t be surprised if he’s the MVP.” – Henry (07:25)

• Representation focus: Not just contract negotiation, but managing the full Super Bowl experience, including cultural representation.

5. First and Most Impactful Deals

• First Contracts (08:13)
  • Henry: Kendrick Bourne, complex free agency during COVID, “hard to just get one” with no combine.
  • Big Al: Tariq Owens (Terrell Owens’ son), signed with the 49ers, personal story of fulfillment from coaching him since 17.

    “For me, it was real big because I coached him. I’ve known him since he was 17 and to watch him chase his own dream…” – Big Al (09:37)

• Most Fulfilling Deals (10:02)
  • It’s not about money; it’s about seeing players invest wisely (e.g., purchasing real estate).

    “All those guys going and buying real estate—own your own… That’s something people don’t do. We really push our guys to do that.” – Henry (10:18)

6. Financial Literacy & Player Education

• Emphasize self-education and leveraging credible mentors.

  “There’s too many resources now… but you have to know how to ask for it.” – Big Al (10:52)

• Dangers of Misinformation Online (11:13)
  • Henry wrote “The Information Interview Playbook” aiming to help with networking and filtering quality advice.

    “Go to the man, the woman, that’s doing what you’re trying to do and seek their advice. Fuck the Internet… they’re selling.” – Henry (11:23)

7. Purpose Over Paychecks

• Both agents stress their roles as “life coaches,” helping players build success off the field.

  “What I’m doing now is the same thing [as coaching], just without the X’s and O’s. It’s life coaching. Building them to invest in themselves.” – Big Al (12:22)

8. Why Choose Disruptive Sports Agency?

• Transparent, honest guidance; willingness to give the hard truth to help clients reach their potential.

  “The most successful players want the truth. They want hard feedback. They want to be coached hard… ‘What am I not being told, so I can be the best I can be?’ Simple.” – Henry (12:50)

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Notable Quotes & Memorable Moments

• “My mentor is Aaron Goodwin…the original godfather of black agents. This is why I say I stay in my lane, which is football.” – Henry, 00:35
• “Carousels are like TLC reality shows, man. You're waiting on a call that you may never get—it's all connections.” – Big Al, 04:03
• “I advise all college players to have an NFL agent. There are guarantees in those contracts…you may not get that million dollars.” – Henry, 05:14
• “At the end of the day, you are there to play football. Your tape is your resume.” – Big Al, 06:09
• “Own your own [real estate]. Simple. Nobody else—own your own single family house, own your own investment property.” – Henry, 10:18
• “Go to the person doing what you want to do. Fuck the Internet—they’re selling.” – Henry, 11:23
• “It’s life coaching: building them, helping them pour into themselves and invest in themselves.” – Big Al, 12:22
• “The best players want the truth…so I can be the best I can be—simple.” – Henry, 12:50

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Timestamps for Key Segments

• 00:35: Henry & Big Al’s backgrounds and connection
• 02:33: The wild coach free agency carousel explained
• 04:56: NIL impacts—should athletes stay in college or go pro?
• 06:09: The importance of “tape” and football decisions
• 07:25: Representing athletes at the Super Bowl
• 08:13: Agents’ first memorable deals
• 10:02: Most fulfilling deals—not about money, but long term success
• 11:13: Player education, misinformation, and Henry’s book
• 12:22: The life-coaching mentality in representation
• 12:50: Why Disruptive Sports Agency? Honesty, hard truths, and player growth

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Conclusion

Laced with humor and packed with insight, this episode offers a genuine look at the business (and heart) behind athlete representation. Listeners get practical wisdom on building a career in sports—on and off the field—as well as timeless advice on mentorship, honesty, and life after the game.

Transcript

[A]

Foreign. We got the Hondo's blockbuster introduction today. We got Bobby in the house. We got Henry. We got Big Al. We're here on super bowl media row. How we feeling, boys?

[B]

Fantastic.

[C]

Great.

[A]

Good, Good vibes out here. Energy's high. Very, very different dynamic than. Than yesterday. What do you think? What do you think?

[D]

I'm hyped up. My boy Henry say he's bringing the

[B]

juice today, so we're going to find out today, man. We're bringing that heat.

[A]

I like it.

[C]

I like it.

[A]

So before we get into the heat, we want to tell you guys stories. Tell us how you got into the landscape that you guys work into now.

[B]

Yeah. My name's Henry Oregon. I worked at Nike in football brand marketing out of college undergrad. Played football in college at Portland State. After working at Nike, I went to work for a sports agency in Seattle, Washington. It was great. Did marketing there and realized I wanted to become a certified agent. One of my mentors is Aaron Goodwin. Shout out to Ag the Goat, the original godfather of black agents. He is in the basketball space. This is why I say I stay in my lane, which is football. You know, Aaron Goodwin also represented LeBron James and taught Rich everything he knows. I'll say it on camera.

[C]

Ham.

[A]

Hot take already.

[C]

Hot take. That's him for you. My backstory is a lot different than Hans. So I played college football, and then I started coaching college football for roughly 10 years. Junior College, Division 1, and Hen and I, we've been friends forever, and he's my mentor in the age of game, and I learned everything from him. And, you know, it was one of those things where he said, hey, come jump on this adventure with me. And I dove all the way in, and we were able to do some great things with players. And I also helped start our coaches division, represent almost 100 coaches across college football in the NFL and now head coaches in college football. So it's big time.

[A]

So how'd you guys link up?

[C]

Oh, I ran him over in Pop Warner.

[B]

He couldn't run. Time out. Time out. He never ran me over.

[C]

What's the kid in the little Giants?

[B]

We couldn't even play in the same weight class. He was, like, literally five leagues away from him.

[D]

My boy was seven playing in varsity,

[C]

so this was him in our weight class, and this was me.

[B]

Legit.

[A]

Yeah, we got the. He had the power of Cavacito. That's dangerous. A little cavecito.

[C]

Hands not ready for it.

[A]

That's sick. That's sick. So, yeah, so you guys now representing coaches at college. So nil as well.

[B]

Yep, as well. We primarily focus, though. You say coaches, so NFL front office executive coaches, college coaches, and college front office executives as well.

[A]

So talk to us about. I felt like this year, that whole free agency cycle of coaches specifically, was wild.

[B]

Yeah.

[A]

What'd you guys think of that?

[C]

It was a domino effect, right? We knew it was coming. We knew the winner was coming. Right. It was one of those deals where you just try to, like, get ahead of it as best you can and try to get your guys in there. We did an awesome job this year. Our whole team did. Our whole disruptive network did a fantastic job getting guys in. And, you know, hen kind of sets the tone and the vision with the juice, he wakes up with his piss hot, and he goes, I wish we

[A]

had a camera on you to see what these but behind the scenes conversations look like.

[B]

We got cameras, man. We welcome it. We are disrupting.

[D]

Me and my boy Dave, we'll follow y'.

[B]

All. Welcome all to media attention.

[A]

I love it.

[B]

But the domino effect, for your question.

[C]

Yeah.

[B]

You know when that happens, you can see the cycle, right? It's like every two, two, three years, and then you're loading the chamber up for your dominoes into hell.

[C]

Yeah, Right.

[B]

You know what I mean? So.

[C]

Oh, yeah.

[D]

Give my time, baby.

[A]

I got this.

[D]

I want to know, like, the difference in, like, the coaching carousel versus, like, NFL player carousel. Like, is there more drama? Less drama? Is it more business? Is it more straightforward?

[B]

That's a great question.

[C]

That is a good question.

[B]

You know, it's always drama. Yeah, Right. But you ready for it, you know? So it's just the fire is always hot. You gonna make it hotter or you fizzle out.

[C]

I think carousels are like TLC reality shows, man. Cause because you're waiting on a call that you may never get, right? And it's all connections, right? It's not who knows you, you know, it's who do you know that can help get you on too? And so everybody is just trying to get in front of their. Their guy that they knew that they worked with three jobs ago. Whereas the NFL, it's like, hey, we have tape. We have all these things to study. There's no metric on coaches, right, Besides wins and losses. Yeah, Wins, losses. And I would say now at the smaller level is guys that are getting other guys to a bigger school, right? Because, nil, how do I go from, you know, New Mexico to Virginia Tech and what does that money look like? Like, how did they get developed in New Mexico to Get to Virginia Tech or Miami or Texas Tech, you know, and so just being able to have those things in your arsenal and in your toolbox and be able to do it for sure.

[A]

And I think you brought up something interesting right before the landscape was you're just going to go straight into the NFL the moment you had that chance. Now you can kind of think twice about that decision. What have you guys seen now with NIL and the amount of money that's being involved there to get guys to either commit to the NFL or what informing kind of what is the right decision there?

[B]

I mean, as NFL certified agents. Right. There's not many certified agents to off nil. They're starting to get more aggressive now. But it's really hard. Right. Because the money is so good in nil. But it also. Right. The devil's in the details. When does that money pay out? You know, I really advise all college players to have an NFL agent and not just somebody that's your uncle, your cousin or NL master because there's. There are guarantees in those contracts. There are stipulations that can be broken for you. You may not get the million dollars, which has been a thing. But even now it's more prevalent because the schools are not enforced. They're not playing that take your ass to court.

[C]

And I think to also piggyback off that sometimes, yes, the money is great, but when you're playing good football, you go. Your tape will always be your resume. This is football. At the end of the day, it's not about money and endorsements. You are there to play football. And if you have great tape and you're playing great football, go.

[A]

Yeah. I mean, we were talking about it more from Oregon.

[C]

Yep.

[A]

That one to me was interesting. Right. Especially with the way QB class is this year.

[C]

Yep.

[A]

Obviously Fern number one overall pick this year. He solidified him in there. But it was strange for me to think that he was not a guy that probably should have gone to the NFL.

[B]

And we did too. Right. But we know some of his representatives. I don't know him personally, but. Right. The statistics show that quarterbacks that are playing for more than starting more than a certain amount of games more successful. So he's looking at the long term. How do I be more successful in the NFL Even though the money may have been a lot higher to go to the. To go be a pro.

[A]

Yeah.

[B]

So it's not just he's going back to school to win. He's going back to school so he can become a better pro and develop yeah, yeah.

[D]

And I like to make the joke as a Dolphins fan that he went back to school because the jets were looking at him. If you're trying to do what's best for your career, like you just said, the jets might not be the answer. I mean, you got Darnold in the super bowl and look what the jets did to that guy.

[B]

I mean, dude, hey, you know, hey. Not what they did. It's just circumstances, right?

[A]

Yeah.

[B]

Culture, you know, we're going to answer politically. You know what? Shit happens.

[A]

Yeah.

[C]

Yeah.

[A]

So you guys got a couple guys that are going to be playing in the game this weekend, the big game, the Super Bowl. How's the dynamic of this week, you know, with the guys that you guys have?

[B]

George Holani is going to dominate. I think he's going to do really well. You know, don't be surprised if he's the mvp.

[C]

Oh, hot take, hot take, hot take. What, are they going to throw the ball every time you got a hot take? But no, it's exciting, man. You have the guy in a Super bowl and like he's piggyback off what he said. George, I think is underrated in some of his skill sets and I think, you know, he'll be in on big third down, key third downs, either pass, blocking or catching out the backfield. Make a guy miss and get another first down and go score.

[A]

So those are the. Those are the plays that make a difference in the super bowl right there.

[C]

Yeah.

[A]

George is just.

[B]

He's a good kid.

[A]

Yeah.

[B]

You know, be prepared for the outfit he wears to represent his culture, you know, pregame. So.

[C]

Hell yeah.

[B]

Hell yeah.

[D]

I always like to ask with agents, like, I got two questions. First one, do you remember your first deal?

[B]

Absolutely.

[C]

Absolutely.

[D]

Who was it?

[B]

First deal was Kendrick Bourne. That was my first line.

[D]

Kendrick Bourne.

[A]

Okay, cool.

[B]

Oh, yeah, during COVID Fresh out of COVID He got a second round Tinder the year before, so I think that's my first deal. But the team kind of has to give you one or two as far as that kind of player. But hidden free agency, I don't think it was the year after there was no combine and it was great. Yeah, a lot of teams stopped going to the combine, so it was hard to kind of just get one. And you know, Patriots jumped out there and they wanted them and there was some overlap and my high school quarterback was the receivers pitch. So that was a good first deal. 18, 19 of it. And he was successful still. He's still playing.

[C]

Yeah, yeah.

[A]

And he had a good year. This year, too.

[D]

That one that stands out.

[C]

The one that stands out to me, that I'm probably the very first deal on my own was Tariq Owens. Terrell Owens, son. Oh, nice. And so Tariq is friends with your guys, Javon Holland. Right. And Tariq signed with the 49ers, you know, undrafted free agent and went out there and stuck on the practice squad the first year. Caught a touchdown in the preseason this year, and so.

[B]

And Big Al coached him.

[C]

Yeah, that's what I'm telling you. I also coached him. You know, it was full circle for a moment to watch him. There you go. There's that. Another one.

[A]

We're gonna have to get a game rolling after. Oh, yeah.

[B]

Oh, man, this has got to be all day.

[A]

All day. Yeah.

[B]

There you go.

[C]

That's the first. That one for me was like, you know, real big because I coached him. I've known him since he was 17 years old. And to watch him grow into a young man and be out and go kind of chase his own dream while still living, you know, a certain type of way, and go.

[D]

And you kind of answered my second question. So I'm asking you now not what deal made you the most money, but what deal made you fulfilled you the most? What deal was you like, man, I'm glad I took care of this kid. I'm glad we got that done.

[B]

I mean, honestly, all of them, right? Like, you look at it like the players that you represent, the deals you do, that's your resume.

[C]

Yeah.

[B]

So they're all, like, stacking chips to get better and better, but.

[C]

Stacking chips.

[B]

Yeah. There you go.

[C]

We got.

[B]

We got.

[A]

We got so much ammunition here.

[B]

I'm stopping gambling chips, but I don't gamble. But just honestly, all those guys going and buying real estate when they do and owning it on their own, I think that's something that people don't do. We really push our guys to do besides just having equities in the market.

[A]

Right.

[B]

But own your own.

[A]

Interesting.

[B]

Nobody else. Own your own single family house. Own your own investment property. Simple.

[C]

Yeah.

[A]

I mean, that's huge. I mean, we've seen guys in the past, right. Get burned. Right. And it's no one's fault. Right. I mean, it's just a lack of education at the end of the day. So having guys like you is huge.

[C]

I mean, that is someone's fault. It could be yours. Right. We have to own it 100%. Like, and there's too many resources nowadays, whether it be YouTube or, you know, all these things, to be Able to go learn something. And there's too many people that are willing to share information, but you have to know how to ask for it. Yeah.

[A]

You know, and I think off of that, too, it's. It's counterintuitive almost.

[C]

Right?

[A]

Because, yeah, there is a lot of information out there that's valuable, but there's also a lot of misinformation out there. So you might be consuming that and be like, it's good, but you don't know if it's good or not.

[B]

So I wrote a book called the Information Interview Playbook, and it's all the skills I learned to get to where I'm at today. And my thing is, right, the Internet, anything you see online, YouTube, they're selling you something, right? That's all. Go to the person, the man, the woman, that's doing what you're trying to do and seek their advice. Right. They've done it. Fuck the Internet, because half the time, they don't even own this. They're selling.

[A]

Yeah.

[C]

And because I'm a good friend, I have read his book and I can attest to it.

[A]

You know, where do we get the book?

[B]

You can get anywhere. It's in Target. It's at Barnes and Noble. It's called the Information Playbook. It's on Amazon. Please use my publishing, Amplify Publishing so I can make the most amount of royalties. Thank you so much.

[C]

Add the link right there and he's a triple threat. You got to be careful.

[A]

That's sick. That's sick. Well, no, man, I mean, that's awesome. It's. It's great to see, like, the work that you guys do and that there's purpose behind it. Right. It's not. It's not just collecting a paycheck. It's not just going through the motions. It's. It's the purpose behind helping people. And I think when that's always the backbone of all that you do, it's only going to replicate into success.

[B]

Absolutely.

[C]

And I think just to quickly piggyback off that, I was a college football coach for a long time. We talk about development, right? We talk about pouring into young men. What I'm doing now is the same thing, just without the X's and O's part. It's life coaching. It's getting them and building them and helping them pour into themselves and invest in themselves. No, exactly what you said, 100%.

[A]

You got anything?

[D]

Yeah. Last thing you know. If you were talking to a client or future client, why would you tell them to choose disruptive over someone else.

[B]

I'm gonna tell you the truth, as you should. And the most successful players, the best players, they want the truth. They want the hard feedback. They want to be coached hard, like Tyquan Thornton, like Kendrick Bourne and all the rest of it. They want to know, hey, what am I not being told? So I can be the best I can be simple?

[C]

Hell, yeah.

[A]

Hell, yeah. Well, boys, appreciate you guys for coming on.

[B]

Appreciate you.

[C]

No, we appreciate you guys.

[A]

We got. We got to do this again. Like.

[B]

Yeah, come on, man.

[C]

Our normal thing.

[A]

We got to get interviews. We got to get the. The cameras following him around.

[C]

We're ready.

[A]

Let's do it.

[C]

You can't miss me. I might be the biggest person in here.

[A]

Last year, when I. When we met at the. At the event with Vaughn, Yeah. I was like, bro, this guy's a big dude.

[C]

Well, it's funny. Today, Taekwond's doing an interview, and Chris Long, Howie Long's son, he's looking at me, I'm looking at him, and he's like, hey, man, going to be two big guys over here. Who's going to go? We had a nice little interaction, but it's pretty fun.

[A]

That's dope. Well, I appreciate you boys for coming out, man.

[C]

Appreciate you.

[A]

Good time.