From ESPN to Entrepreneurship: Yussuf Khan 26 Years in Media: My Friends Are Better Than Yours

In this episode of My Friends Are Better Than Yours, BIG CED sits down with Yussuf Khan, a 26-year sports media veteran who’s worked everywhere from ESPN to startups, and now runs his own platform, First and Pen.

Yussuf shares his incredible journey—from DJing in NYC clubs while working in banking at Chase Manhattan, to taking a 50% pay cut to break into ESPN, to running The Shadow League for nearly 7 years. Now, he’s building something different with First and Pen, a sports publication focused on quality storytelling over clickbait.

We discuss:
✅ The state of sports journalism and the race to be first vs. being right
✅ Why he left corporate media to start First and Pen
✅ Teaching the next generation of sports business professionals
✅ The “Get in the Game” sports business career conference in Baltimore
✅ Preserving Black sports history that’s being erased
✅ Breaking into the sports industry without an athletic career
✅ The real work behind Stephen A. Smith’s success

Yousef also teaches sports management at universities in New Jersey and New York, and is passionate about creating pathways for HBCU students and students of color to enter the sports industry.

🔗 Connect with Yussuf Khan:
Website: firstandpen.com
Email: firstandpen@thegroup.com
Social Media: @firstandpen (Instagram, X/Twitter, Threads)

📍 Get in the Game Sports Business Career Conference – Baltimore

Over 40 students placed in internships/jobs in 3 years!

If you think your friends are better than mine, either they’re already my friends, or I’ll prove you wrong!
#SportsMedia #Entrepreneurship #ESPN #FirstAndPen #SportsJournalism #HBCUs #CareerAdvice #theindustrycosign #BIGCED #YussufKhan #Sports

Timestamps:
0:00 – Intro & Welcome
1:03 – Who is Yussuf Khan?
2:44 – Meeting at The Shadow League & Black Enterprise Partnership
4:08 – Growing Up in NYC & Early Career Path
5:23 – Entry Point into Sports Business
6:47 – From DJing to Banking to Sports
7:49 – Working at Madison Square Garden During the ’99 Knicks Finals Run
8:27 – Taking a 50% Pay Cut to Join ESPN
10:35 – Career Highlights & High Points
12:29 – Learning the Business at ESPN & Moving to Startups
14:05 – Building Startups That People Thought Would Fail
15:08 – Why He Started First and Pen
17:04 – The Problem with Modern Sports Writing
18:24 – Mindset Shift: Running Your Own Company
20:40 – Why He Doesn’t Chase Traffic Numbers
22:24 – The Race to Be First vs. Being Right
24:40 – The Sherrone Moore Story & Responsible Journalism
27:04 – The Problem with Social Media News
29:35 – Teaching College Students About Fact-Checking
32:04 – The “Get in the Game” Sports Business Career Conference
35:26 – Advice for Breaking into Sports Management
38:13 – The Stephen A. Smith Work Ethic
41:01 – 2026 Plans: Preserving Black Sports History
43:09 – What He Would Do Differently
45:14 – How to Contact Yousef & First and Pen
46:32 – Outro

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https://www.iheart.com/podcast/269-the-industry-cosign-105171601/