Omar Bailey: From Getting Denied Jordans to Designing for the NFL & Icons | DSH #1684

Everyone wants “overnight success,” but Omar Bailey is here to tell you the truth: it doesn’t exist.

In this episode, Omar — cofounder of Factory Lab, former Head of Innovation Lab at Yeezy, and designer behind some of the wildest shoes in culture — breaks down what it really takes to build something iconic over decades, not months.

📚 What You’ll Learn From This Video

👟 Why footwear is one of the hardest, most capital-intensive products to build

🚫 The #1 startup rule Omar lives by: never make the same mistake twice

⏳ Why “overnight success” is a myth and why taking your time actually wins

🧠 How working at Yeezy completely rewired his creative brain

🧪 How Factory Lab “sandbox thinking” turns half-baked ideas into real products

🤝 Why the right cofounder & investor “dream team” can change your entire trajectory

🔁 How failures in cleats, collabs, and launches built unshakable confidence

🎯 Why young creators need to trade urgency for mastery and long-term focus

CHAPTERS:

00:00 - Intro

00:45 - Omar Bailey’s Keanu Reeves Interview

06:06 - Factory Lab: Footwear Incubator

10:18 - Quince Brand Overview

11:23 - Boring Footwear Trends

13:03 - Yeezy Days Discussion

15:43 - Writing Your Own Biography

16:40 - Becoming a Shoe Designer

19:30 - The Myth of Overnight Success

22:45 - Visionaries on Roku Episode 4

25:02 - Finding Omar Bailey Online

25:37 - Like & Subscribe

🎙️ APPLY OR CONNECT

👉 Apply to be on the podcast: https://www.digitalsocialhour.com/application

📩 Business inquiries / sponsors: sean@digitalsocialhour.com

👤 GUEST:

Omar Bailey - https://www.instagram.com/theomarbailey/?

https://www.instagram.com/fctrylab/

https://therokuchannel.roku.com/enguard/

💼 SPONSORS

QUINCE: https://quince.com/dsh

🥗 Fuel your health with Viome: https://buy.viome.com/SEAN

Use code “Sean” at checkout for a discount!

🎧 LISTEN ON

🍏 Apple Podcasts: https://podcasts.apple.com/us/podcast/digital-social-hour/id1676846015

🎵 Spotify: https://open.spotify.com/show/5Jn7LXarRlI8Hc0GtTn759

📸 Sean Kelly Instagram: @seanmikekelly

⚠️ DISCLAIMER

The views and opinions expressed by guests on Digital Social Hour are solely those of the individuals appearing on the podcast and do not necessarily reflect the views or opinions of the host, Sean Kelly, or the Digital Social Hour team.

While we encourage open and honest discussions, Sean Kelly is not legally responsible for any statements, claims, or opinions made by guests during the show.

Listeners are encouraged to form their own opinions and seek professional advice where appropriate. The content shared is for entertainment and informational purposes only — it should not be taken as legal, medical, financial, or professional advice.

We strive to present accurate and reliable information; however, we make no guarantees regarding its completeness or accuracy. The views expressed are solely those of the speakers and do not necessarily represent those of the producers or affiliates of this program.

🔥 Stay tuned for more episodes featuring top creators, founders, and innovators shaping the digital world!

🔑 Keywords

Omar Bailey, Factory Lab, Heart and Sole book, Heart and Soul Omar Bailey, Yeezy, Kanye West sneakers, sneaker design, footwear design, startup advice, don’t make the same mistake twice, overnight success myth, ComplexCon interview, Keanu Reeves Visionaries, Roku Visionaries Omar Bailey, duck boot collab

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