True Underdog
True Underdog
May 31, 2021
#72: Diversity in Business with Cheryl Contee
Play • 28 min

Today on the show Jayson is talking with Cheryl Contee, CIO of The Impact Seat, Chair / Founder of Do Big Things, and the Author of Mechanical Bull. Cheryl talks about how devastating it can be to be judged by your appearance in a professional, venture investment setting, how she has dealt with rejection because she’s a minority and what we can do to solve that problem going forward.

There’s a big problem today with minorities not getting the same opportunities as everyone else, and we all need to work together to help move past the situation.




Follow True Underdog on IG:

Reach out to Jayson directly at

Follow Jayson on Linkedin:

Follow Jayson on Instagram:

Check out our website to meet the team, view show notes and transcripts:


Mentioned in the Episode:


Medium Blog:








2:03 - Creating a Better, More Professional Space For Women

3:33 - First Black Female Founder to be Acquired by NASDAQ

5:33 - Dealing with Rejection

9:32 - Being Judged by Your Appearance

12:18 - Being a Woman, and Being the Breadwinner

14:38 - Women vs Men For Job Prospects

17:42 - Take the Moment You’re Given No Matter Who You Are

18:40 - Cheryl’s Book, “Mechanical Bull”

22:50 - Giving Back to People Who Were Like You

24:12 - Why Should We Embrace Failure?

25:42 - Practice Your Pitch on Clubhouse

27:27 - Where to Find Cheryl Online

More episodes
Clear search
Close search
Google apps
Main menu