Digital Social Hour – Omar Bailey: From Getting Denied Jordans to Designing for the NFL & Icons

Podcast: Digital Social Hour
Host: Sean Kelly
Guest: Omar Bailey (Co-founder, Factory Lab)
Episode: #1684
Date: December 15, 2025

Episode Overview

This episode features a deep-dive conversation with Omar Bailey, a pioneering footwear designer and entrepreneur, recognized for his influential work with Yeezy, his founding of Factory Lab, and collaborations with artists and NFL athletes. The discussion explores Omar's lifelong journey in footwear—from a childhood longing for Jordans to leading some of the most talked-about sneaker projects of the last decade. He shares hard-won insights on creativity, the struggles of manufacturing, innovation in a stale industry, and the importance of persistence and vision. The episode also touches on Omar’s new book, "Heart and Soul," his background, and his impact on the culture of footwear.

Key Discussion Points & Insights

1. The Value of Patience and Learning from Mistakes

• [00:40] Omar stresses the long-game in entrepreneurship:
  “The biggest thing when you run a startup is don't make the same mistake twice. When you make a mistake, you learn from it, you move on, and you keep growing.”
• He notes the misconception of "overnight success" among the younger generation and advocates for taking time to become an expert.

2. Keanu Reeves Documentary & Industry Perspective

• [01:30] Omar discusses his feature in Keanu Reeves' documentary series and notes the challenges distinguishing footwear design from apparel:
  "Footwear is just very difficult when you start factoring in the sizes. ... you could be... in deep 100 grand just in, like, development costs for one style of shoe. But that's what it takes..."
• [02:38] Sketching the concept is the “easiest part”—real challenges begin in development, manufacturing, and bringing ideas to life.

3. The Yeezy Era: Innovation and Legacy

• [04:17] Reflecting on his role as Head of Innovation Lab at Yeezy:
  "It was a cash machine, like you were printing cash... But no, it was amazing... a family environment... when we were able to put one of those products out on the market and see the response... it was a very rewarding feeling for all of us."
• Omar details both the creative breakthrough and market impact achieved by the team, highlighting Kanye West’s unique vision and its influence on the industry.

4. Factory Lab: Democratizing Footwear Innovation

• [06:46] Factory Lab is described as a “footwear incubator”—a launchpad for creatives and celebrities to actualize sneaker concepts:
  "Think of Factory Lab as an incubator who's democratizing footwear and making basically the entry, the barrier of entry into footwear much easier."
• The firm leverages Omar’s 20+ years in the industry to guide projects for artists like Agnes Mo and NLE Choppa (the viral Duck Boot), and even its own signature models.

5. Reimagining Classics – Breaking Industry Monotony

• [10:09] Shoes are approached through the "Factory Lab lens," likened to a creative sandbox:
  “You come in there with a vision. It doesn’t have to be cooked … let’s take that through the Factory Lab lens and mold that into an actual new concept.”
• Omar critiques the last decade’s trend of brands copying each other, emphasizing the need for disruption:
  [12:38] "Footwear has been boring for the last decade... a lot of brands have just been copying each other... We were a bit of a groundbreaker with Yeezy."

6. Culture, Media, and Influence

• [13:42] On the media landscape shift (live streaming, podcasts):
  "There's a lot of fragmented audiences... it's a little bit like whack a mole, right? ... one of our benefits in being small and nimble at Factory Lab is we have the ability to kind of get our hands on a lot of different places at one time."

7. Personal Story and Upcoming Biography

• [16:23; 17:11] Omar previews his book "Heart and Soul," recounting his journey from a childhood in the ‘90s—when his parents denied him Jordans to keep him safe—to sketching shoes, art school, and his path through major companies.
  • On inspiration: "My story isn't someone who just started doing this and in a year I became some multimillionaire. ... It’s a story of resilience. It's a story of belief. It's a story of betting on yourself."
  • [20:15] "Overnight success is not a real thing. Unless you hit the lottery ... You've got to put the work in... it takes time."

8. Technical Craft & Comfort

• [22:18] On his approach to comfort and design:
  “People say that it doesn’t feel the way it looks. And I like that, because...it speaks to the comfort. I like to design shoes from the inside out just as much as the outside in...thinking about comfortability, thinking about the last...then creating the outer skin or the outer silhouette...”

9. Showcasing the “Obi Wan” Shoe

• [23:27–25:21] Omar gifts Sean a pair of his signature Obi Wan Highs, sharing its origin story (first launched in Dubai in 2016, relaunched through Factory Lab). The shoe’s pedigree and comfort are praised:
  • Sean: "This is the biggest shoe I’ve ever seen. ...the smoothest shoe I’ve ever felt."
  • Omar: "You're going to get stopped constantly when you wear this shoe...that just tells me we’re doing our job, by creating things that just stand out and are different."

Notable Quotes & Memorable Moments

• Patience in Success
  • “You didn’t become who you were overnight. Right? It takes time...you had to make mistakes…” (Omar, [00:40])
• On Creativity vs. Manufacturing
  • “Designing the shoe is actually the easiest part...everything from that point forward is extremely difficult.” (Omar, [02:44])
• On Yeezy’s impact
  • “I don't think it'll ever be replicated or duplicated...it forced me to think about footwear in a very different way.” (Omar, [05:28])
• Factory Lab Vision
  • “Think of Factory Lab as like a sandbox...you can come in there with a vision. It doesn’t have to be cooked...let's take that through the Factory Lab lens.” (Omar, [10:09])
• Culture Shaping
  • “One of my favorite comments about...shoes that we create is people say that it doesn’t feel the way it looks.” (Omar, [22:18])
• On “Overnight Success”
  • “I'm here to tell you, it is not real. Overnight success is not a real thing. Unless you hit the lottery.” (Omar, [20:15])
• On Recognition
  • "People always hit me up, said, man, I was wearing this shoe and like 10 people stopped me in the airport. Like, what is this? Where'd you get that from?" (Omar, [25:22])

Timestamps of Key Segments

• [00:40] – Lessons in patience and learning from mistakes
• [01:36] – Experience on Keanu Reeves’ documentary
• [02:38] – Why manufacturing and scaling shoes is so difficult
• [04:17] – The “cash machine” years at Yeezy
• [06:46] – Factory Lab’s role as incubator
• [10:09] – Creative process at Factory Lab (“sandbox” method)
• [12:38] – Footwear industry critique & push for innovation
• [13:42] – Navigating new media & fragmented audiences
• [17:11] – Omar’s biography and formative years
• [20:15] – Falsehood of “overnight success”
• [22:18] – Inside-out approach to shoe design & comfort
• [23:27–25:22] – Gifting and story of the Obi Wan shoe
• [25:48] – Ways to follow and support Omar (Visionaries on Roku, Factory Lab Instagram)

How to Support & Learn More

• Watch: “Visionaries” documentary (Roku, episode 3, with Keanu Reeves)
• Follow: @FactoryLab (Instagram: fctrylab), @theOmarBailey
• Book: “Heart and Soul” by Omar Bailey (Coming 2026)

Episode Tone & Vibe

The conversation is candid, insightful, and motivational, balancing nostalgia, technical know-how, and forward-looking innovation. Omar’s approachable, passionate storytelling and openness about both his victories and setbacks contribute to an inspiring and authentic episode.