What Founders Can Learn From The Ambition of Diana Ross

File N°34.

Author

LaToya Allen
April 12, 2025

Welcome to The Strategy Files—a newsletter about history's most successful founders in fashion, beauty, and culture. I study the icons, you apply their strategies; you win.

This month’s deep dive comes from the book Diana Ross: Secrets of A Sparrow.

Lessons From This Month’s Deep Dive 

  1. You don’t need to know what the next step is. You just need to move forward.

  2. Being around ambitious people will make you more ambitious. They won’t quit when they hit a roadblock.  You won’t either.

  3. They say if you work hard and don’t quit, you’ll eventually succeed. But this only works if you’re improving, iterating, experimenting, practicing. Because Longevity + Improvement = success.

  4. Start small. Too many people never start.

  5. Practice, Practice, Practice.

  6. Closed mouths don’t get fed. Neither do those who lack clarity. You have to ask for the opportunities you want in a straightforward, clear, obvious way. 

  7. In order for a group of people to succeed as a unit, you have to do what’s best for the unit.  Sometimes, that means letting people go.

  8. Sometimes, a no is just a delayed yes. 

Diana Ross has always been wildly ambitious.

In 1961, at the age of 17, Diana Ross and The Supremes signed their first record deal with Berry Gordy, the founder of Motown Records. In 1965, the group was nominated for their first Grammy. By the time 1969 rolled around, The Supremes had 12 number-one singles on the Billboard Hot 100, including some of my personal favorites: "Where Did Our Love Go," "Baby Love," "Come See About Me," "Stop! In the Name of Love," and "Someday We'll Be Together."

Diana released 26 solo albums, won an Academy Award for playing Billie Holiday in Lady Sings the Blues, and eventually became a part-owner of Motown Records, the company she helped put on the map as a teenager.

Last year, Diana modeled for Saint Laurent in their spring 2024 campaign.  Today, she still sells out arenas all over the world.

But not all ambitious people get to her level, and most don’t tap into their ambition until later in life. They aren’t accomplishing great things at the age of 17.

What was different for Diana?

I have a theory. The world would have been robbed of Diana’s talents if she didn't spend her early teenage years surrounded by wildly ambitious people.

See you next week for part 2,

LaToya

References && Further Reading

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