When did Dia Simms work for Diddy? Rapper's former assistant went from being a DoD employee to taking over cannabis industry

Diddy has built a successful business empire spanning fashion, spirits, fragrance, content, and preparatory schools. One key figure in his success is Dia Simms, who began working for him in 2005 as his executive assistant.

Simms joined Diddy's workforce as his executive assistant and is also credited for turning his label - Bad Boy Records - into Combs Enterprises. Thereafter, she helped the rapper build multiple businesses and brands under the umbrella of Combs Enterprises.

Simms worked in the Department of Defense before she joined Diddy's business, and 14 years later, quit her role to enter the cannabis industry.

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Dia Simms became the first-ever president in the history of Diddy's company

After joining Diddy's company, Simms oversaw multiple brand portfolios and expanded them over time. One of her major achievements in the enterprise was the transformation of CIROC - the premium vodka brand that was initially unprofitable, with Simms turning it around, making its retail brand value grow to $2 billion.

After working in the Bad Boys for Life rapper's company for more than a decade, Dia was named its president in 2017 - making her the first-ever president of the company. In an interview with Marie Claire on October 11, 2019, Simms was asked if the thought of being the first person to assume the presidential role in Diddy's Combs Enterprises scared her.

To that, she responded:

"The fortunate part about having been there for 14 years was that the promotion wasn’t scary because I had been thinking about the products every day. You’re always looking to your left and your right thinking, 'How can we be better and go into this particular business initiative?' So, it was a massive opportunity."

The same week of the interview, Simms left her job at the Young G rapper's company and announced the launch of BRN Group - a firm that offered distribution consultancy for other cannabis companies. When asked about the reason behind this change in the interview, Dia said:

"There’s an economic shift that’s a once-in-a-millennium type of thing where this exploding industry in North America is an opportunity for all of us to create real change, real jobs, real legacy wealth for families. I couldn’t just sit on the sidelines and not be a part of it."

Simms also revealed about having her eyes on the cannabis space in the final years of working at Combs Enterprises. She learned about cannabis "really working" through her mother, who suffered from multiple sclerosis for a long time, and found great relief through cannabis.

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Simms admitted to being inspired by Diddy in a Forbes interview

On September 6, 2018, Dia Simms was interviewed by Forbes, where she was asked about what she learned from Sean "Diddy" Combs. Simms answered with the Show Me Your Soul rapper's vision to make big bets, claiming he pushed her to stretch her aspirations, explaining:

"If I thought I could colonize Mars, he [Combs] would be like, "We could do the whole Milky Way. Think bigger.'"

The president of Combs Enterprises also called his way of doing things "in the most obnoxious, crazy, miracle way" her biggest motivator. In a 2020 interview with Essence, Simms called her time at Combs Enterprises "a wonderful run," elaborating:

"After 14 years, it was just a wonderful run. But I really wanted to have real significant and deep levels of ownership and authority over my work. Puff was a phenomenal partner, but this was a chance… I thought, 'Hey, this is an industry that is burgeoning and I’m really excited about the opportunity in the cannabis space.'"

Simms is currently the CEO of BRN Group, alongside being a board member of TILT Holdings.