When Did Dia Simms Transition from Diddy’s Assistant to Leading the Cannabis Industry?

Diddy has established a thriving business empire that encompasses fashion, spirits, fragrance, entertainment, and preparatory schools. A significant contributor to his success is Dia Simms, who began her journey with him in 2005 as his executive assistant.

Simms initially joined Diddy as his executive assistant and played a pivotal role in transforming his label, Bad Boy Records, into Combs Enterprises. Subsequently, she assisted the iconic rapper in developing multiple businesses and brands under the Combs Enterprises umbrella.

Before partnering with Diddy, Simms worked in the Department of Defense. After 14 years at Combs Enterprises, she made the decision to transition into the cannabis industry.

Dia Simms: The Pioneering President of Diddy’s Company

Upon joining Diddy’s organization, Simms managed several brand portfolios and gradually expanded them. One of her notable accomplishments was the revitalization of CIROC, the premium vodka brand that was initially struggling. Under her leadership, CIROC’s retail brand value surged to an impressive $2 billion.

After more than a decade with Diddy, Dia Simms was appointed president of Combs Enterprises in 2017, marking her as the first individual ever to hold this position within the company. During an interview with Marie Claire on October 11, 2019, Simms was asked whether the prospect of becoming Combs Enterprises’ first president intimidated her.

Her response highlighted her long tenure:

“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.”

In the same week as her interview, Simms announced her departure from Diddy’s company to launch BRN Group—a consultancy firm aimed at distributing resources to other cannabis companies. When asked about the motivation behind this career pivot, Dia explained:

“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 shared that she had been eyeing the cannabis market towards the end of her time at Combs Enterprises, influenced by her mother’s battle with multiple sclerosis, for which cannabis provided significant relief.

Simms Finds Inspiration in Diddy: Insights from a Forbes Interview

On September 6, 2018, Dia Simms sat down with Forbes to discuss what she learned from Sean “Diddy”Combs. She spoke about Diddy’s visionary mindset and ambition to take big risks, noting his encouragement to aim higher:

“If I thought I could colonize Mars, he [Combs] would be like, ‘We could do the whole Milky Way. Think bigger.’”

Simms attributed her motivation to Diddy’s unique approach, which she described as “in the most obnoxious, crazy, miracle way.”In a 2020 conversation with Essence, she reflected on her experience at Combs Enterprises, stating:

“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.’”

Currently, Simms serves as the CEO of BRN Group and is also a board member for TILT Holdings.

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