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Episode · Sep 11, 2026 · 1 hr 55 min

From a Prison Cell to Nike Brand Director

with Jordan Rogers

Jordan Rogers is a former felon and Nike brand director who is building an independent business after recovery from opioid addiction.

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“I'm not putting my name on that work because I don't believe in it.”
Jordan Rogers

Summary

Jordan tells Ken he began using heroin at 15 after losing his focus on sports, then describes years of arrests, relapse, probation violations, and trying to outsmart drug tests. Facing a five to twenty year prison sentence and weighing 116 pounds, he arrived in county jail in withdrawal. His parents had already spent his college fund on rehab, and a passage in his mother’s account of his addiction helped him take recovery seriously.

After release, Jordan became a personal trainer, earned a history degree at SMU, and spent four and a half years working toward a job at Nike. He became an EKIN and moved into Nike football and women’s brand roles, working with athletes and designers. As he and his wife raised young children, he began questioning the cost of corporate life. He left Nike, returned to Texas, and started advising schools and athletes on NIL and brand partnerships. He and Ken compare the uncertainty of independent work with the freedom to choose projects and own the results.

Show notes

Jordan Rogers was using heroin at 15. By the time he landed in county jail, he weighed 116 pounds. His parents had spent his college fund on rehab, and he was facing the possibility of 20 years in prison. I know what it’s like to organize your entire life around getting high. There was a lot in this conversation that hit home for me.

We get into his 396 days locked up, what finally changed when he stopped trying to outsmart every rule, and what happened when he read his mother’s account of everything his addiction had put her through. Getting sober wasn’t the finish line. He became a personal trainer, earned his degree at SMU, and spent four and a half years chasing a job at Nike. He went from working in a factory store to becoming a brand director, working with some of the biggest names in sports.

Then he made another hard decision: leaving the job he’d spent years trying to get. We talk about choosing his family, building his own business, and why neither of us wants to give up the freedom of working for ourselves. Jordan didn’t get to undo his past. He had to get honest about it and decide what he was going to do next. That’s what this conversation is about.

Follow Jordan on Instagram: @jordanrogers.

Read the transcript

Transcript

Made from YouTube's automatic captions and lightly corrected, so a few words and names may be off. Click a time to play the video from there.

Ken Rideout

All right, today's guest, marketing guru, former drug addict, former felon, the great Jordan Rogers.

Jordan Rogers

That's right.

Ken Rideout

Thanks for being here, brother.

Jordan Rogers

Thanks for having me, Ken. Honored to be here.

Ken Rideout

I'm excited to talk to you because I'm a huge gear junkie and I absolutely love the fact that you get tons and tons of cool gear sent to your house all the time.

Jordan Rogers

Bro, I'm uh yeah, living a living the dream these days. I'm out here for a trip for a gear for a golf footwear brand and uh I'm just like last night I'm just pinching myself, man. I have two beautiful kids and uh a wife. We just moved into a new house and like I'm just living the most normal crazy life and I look around sometimes and it's like how the hell did I wind up here, dude? People send me products, people fly me places, [snorts and sighs] want to chat, you know?

So, I think Will connected us a few months ago when I saw your story. I mean, I get invited a lot of different podcasts. I'm sure you do cuz everybody's got one now. But then I checked you out, man. I love your freaking mindset. I love the grind, the hustle, and the mentality. And I think it's really needed, and I think we're kind of

I don't know. Uh I'm raising a son and a daughter. I have an audience of a lot of young men, and I think a lot of them need good messages like what you're putting out. and not in a sleazy multi-level marketing scheme crypto [ __ ] you know, that a lot of these kids are sold, man. I feel bad for them. So, like, we need more positive like get to it, let's get get after it, you know, mentality. So,

Key takeaways

  • Owning both wins and losses can quiet the urge to blame other people.
  • Recovery asks people to address the problems behind substance use, not only the substance.
  • Redirecting energy into running, training, and work gave Jordan outlets that competed with old habits.
  • Repeated effort and visible work helped Jordan reach a job that had once seemed out of reach.
  • A job that once felt like the dream can stop fitting when family priorities change.
  • Independent work brings control, along with direct responsibility for the result.

Nowhere to Hide

A weekly letter from Ken Rideout about doing the uncomfortable part, and the reasons we use to avoid it.

It starts with 3 Days, 3 Hard Things: one short story from Ken and one hard thing to do, every day for three days. Then one letter a week.