Diamond Hawkins: A Beautiful Tale

Diamond Hawkins was born without advantage, but has earned her way into celebrity circles and high-powered tech teams. Today she's building a beauty of a startup - Pothos Beauty.

From Nothing, but it Wouldn’t Define Her

Born in the inner city of Bridgeport, Connecticut, to parents at 18 and 19, Diamond didn’t have a lot going for her. She and her parents grew up together near the Connecticut beach. She had the opportunity to be around a very diverse group of people - not only black, but also Hispanic and, of course, white. 

Diamond watched her parents work directly with customers every day. Her mom was a hair stylist and her dad sold cars. She learned a ton about business from those simple interactions. 

At age eight, Diamond sold balloons around the neighborhood to raise money for the families affected by the 9/11 attacks.

By 11, Diamond was a childhood model. She had an experience at a shoot which has stuck with her even today. Diamond was paired with a foundation color that was four shades too light for her skin. She was told that’s all that was available, and she had to go ahead with wearing it. It hurt her body image and took years to overcome.

That event would lead her to Pothos Beauty, but it took a twisting road to get there.

Diamond went on to work at Edible Arrangements because she loved the beauty of creating a bouquet out of fruit.

From there she became a makeup artist. She would continue working makeup on and off for years, as we’ll see later in her story.

Diamond went to high school in a Catholic school. Her parents worked relentlessly to get Diamond out of the inner city schools, paying around $7,000 each year to get her a better education.

That education led her to be accepted to Quinnipiac University, a private college in Connecticut. Diamond was on the Acrobatics and Tumbling team, which has since become an official National Collegiate Athletic Association (NCAA) sport. Diamond studied political science and philosophy, with the goal of understanding the driving forces behind people movements. 

I was really interested in the narrative of how movements of people [happen]. If one person can mobilize people to do bad, why can’t one person mobilize people to do good?

Accidentally Famous?

Diamond worked at MAC Cosmetics as a makeup artist during college. By chance, or so it seems, she was asked to come down to New York City to help out with makeup for a music video. 

Thinking it was a small budget thing she was doing to help out a friend, Diamond went. When she got there, she found out it was a $2 million+ project! 

People always talk about, “it was the lights that got me!”. It was the lights that got me. The lights, the people, the talent, the artists, the components. Just the glamour. I was in awe.

Diamond worked with Take That, A$AP Rocky, made her way backstage for New York Fashion Week and LA Fashion Week, and more. All without pitching her services to anyone. She was just having fun.

Her third year of college saw a move to Washington, D.C. 

Diamond thought she wanted to be a politician, and quickly learned that she absolutely did not.

Diamond realized it was time to be strategic about what she was doing. She headed back to Quinnipiac, quit Acrobatics and Tumbling, finished off majors in political science and philosophy along with a minor in gender studies, and went on to earn an MBA there.

All while being a celebrity makeup artist.

“Normal”, and Yet Not At All

In 2017, Diamond took her MBA and ran with it, taking freelance clients in many industries and levels and then recently with Microsoft, and also as a freelance consultant for small businesses and nonprofits. She helped them change from brick and mortar to cloud-based business, so that they can continue to operate in the changing world.

While freelancing, Diamond started to build her own business. Her first startup was called Traveling With Color, built with the goal to share real stories of things like the slave trade, told in the areas where they actually happened. Her first trip was to West Africa and she made several more before shutting down.

Diamond took a job that was centered around sales to high-level executives. That lasted three working weeks, at the end of which she inspires others to exit the company becuase was treating employees poorly, and she wasn’t afraid to say something. People listened and left. 

Next, she worked at an IT consulting firm, helping the company implement software in Fortune 500 firms. Diamond worked there for seven months before being laid off in early 2020 due to Covid.

She had other offers from firms she had worked with, but none of them felt right.

Back to Her Love

Diamond moved from Austin, Texas, to New York.

She wanted to get back to helping people. Watching other brands successfully make a difference in the world inspired her, and she remembered her time as a young teenager when her makeup made her feel less beautiful, rather than more.

Diamond wanted to make it possible for everyone to feel beautiful. Always. So she set about building Pothos Beauty to make this impact.

Diamond put Pothos on hold, eventually lucking out and taking a freelance role with We Are Rosie, with Microsoft as a client. They found her because she was known for her work to build human-centered processes. A four-month contract turned to a year and a half, and Diamond has been able to get back on her feet. 

Pothos Beauty re-launched in August 2021 and has brands breaking down the doors to be added to the store.

Diamond is headed out now to raise capital to build. She was recently nominated for the Forbes 30 Under 30 list.

It’s been a winding road, but staying focused on what was best for her and for people in general has lifted Diamond to the top of the game. Pothos is blooming, right along with the people it serves.

You can connect with Diamond on Twitter or Instagram as @diamondhawkins_.

Procrastineur’s Take

Diamond is impressive. It’s not because she has worked so many different jobs in her 27 years. Not because she came from inner city Connecticut and made her way to the Forbes 30 Under 30 or on set for some of the biggest music videos in their respective genres. 

She’s impressive because she’s constantly held to her North Star - Diamond always does what she thinks is best for people. She volunteers nights and weekends. She helps small businesses grow with the changing technical landscape. She helps teach people about the history that they won’t learn from a textbook.

She builds a business solely to help people realize that beauty doesn’t have to be limited to what you see in commercials.

Diamond is an entrepreneur at heart. She’s a good one. But she’s also just plain good. We can all learn a lot from someone like Diamond.

Build on.

Will