“I would say – do it all and find your limit, and then work backwards from that limit, because you’ll regret not trying.” – Gaby Riffle-Gonzalez

Gabriella (Gaby) Riffle-Gonzalez is the Founder and CEO of Antipolíticas Cigars, a premium cigar company that draws on her Cuban heritage and four generations of family expertise in the tobacco industry. Inspired by her family’s resilience after leaving Cuba, she’s reinventing the traditional cigar experience with a modern, celebratory focus. Gaby is currently working on expanding the Antipolíticas brand with a line of alcoholic beverages. In addition to being an entrepreneur, Gaby is a Real Estate Consultant with Berkshire Hathaway Home Services as she’s pursuing a master’s degree in commercial real estate at Georgetown with plans to get her MBA at UNC Chapel Hill.

A graduate of the U.S. Naval Academy in Annapolis, Gaby was a Midshipman In the U.S. Navy for nearly four years before joining the U.S. Marine Corps where she held various leadership positions, including Assistant Operations Officer, Series Commander, Special Security Officer, and others, from 2017-2022.

A former basketball player whose dream was to play in the WNBA, Gaby is passionate about  sports and supporting athletes. Through Antipolíticas, she invests in women’s professional sports, including an early investment in the women’s league Unrivaled Basketball. Gaby aligns her diverse experience with her strong values and vision to create a positive impact with all she does.

For a 10% discount at Antipolíticas Cigars, enter code: SABM10.

In this episode, we discuss:

• How Gaby transformed her Cuban family’s tobacco heritage into Antipolíticas Cigars, a modern brand that celebrates nonconformity, success, avoiding political talk, and having a good time

• The story behind her uncle’s preservation of their family’s Cuban tobacco legacy by bringing seeds and expertise from Cuba to Nicaragua

• Her strategic approach to building a lifestyle brand, including partnerships with professional athletes and plans for future product lines

• How she balances multiple ventures, including real estate sales in three states, commercial investments, and pursuing dual masters degrees

• The transition from guaranteed military purpose to entrepreneurship, and her advice about trying multiple ventures to find your true passion

• Her commitment to investing 50% of Antipolíticas’ proceeds into women’s professional sports, inspired by her own journey as a former basketball player

• Her involvement with Unrivaled Basketball, a new women’s professional league launching in January 2024 with TNT media rights

• The importance of having a supportive spouse and making strategic lifestyle choices to fund entrepreneurial dreams

• Her vision for the future: creating celebratory moments and advancing equity in women’s athletics

• How she’s learning to balance multiple pursuits and prioritize time management while building a lifestyle company with a strong brand

In this episode, we sit down with Gaby Riffle-Gonzalez, CEO and Founder of Antipolíticas Cigars, a premium cigar company that’s redefining the traditional cigar experience through a celebration-focused brand. A former U.S. Marine Corps officer and Naval Academy graduate, Gaby shares how her Cuban family’s four-generation tobacco legacy inspired her to create a modern brand that combines heritage with innovation. We explore her unique vision of partnering with professional athletes and investing 50% of proceeds into women’s professional sports, including her involvement with the upcoming Unrivaled Basketball league. Taking us behind the scenes of managing multiple ventures, Gaby offers candid insights about balancing her commercial real estate investments, pursuing dual master’s degrees, and building a lifestyle brand while maintaining a sustainable work-life balance. She also shares valuable perspectives on the veteran transition experience and her advice about trying multiple ventures to find true passion and purpose. This episode is a must-listen for entrepreneurs, veterans considering business ownership, and anyone interested in building purpose-driven brands while maintaining authenticity to their heritage and values.

Connect with Gaby

• LinkedIn

• Facebook

• Instagram

• Contact Links

• Antipoliticas

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Special thanks to Gaby Riffle-Gonzalez for joining me this week. Until next time!

-Scott Mackes, USNA ’01