Digital Social Hour – Episode Summary

Episode: How We Built a $1B Tequila Brand (DSH #1534)
Date: September 15, 2025
Host: Sean Kelly
Guests: Rob Fitzpatrick, John Rainey Jr., Brock Felt (Founders of Naked Diablo Tequila)
Theme: Behind the Rise of Naked Diablo Tequila and Building a Global Spirits Phenomenon

Episode Overview

This episode dives into the entrepreneurial journey of building Naked Diablo, a burgeoning premium tequila brand aiming for a billion-dollar valuation. Host Sean Kelly facilitates an unfiltered, energetic conversation with founders Rob Fitzpatrick, John Rainey Jr., and investment partner Brock Felt. They share the accidental origins of the business, unique strategies for global expansion, the competitive celebrity-driven tequila landscape, and what makes their company and product stand out.

Key Discussion Points & Insights

1. Origin Story and Brand Formation

• Chance beginnings:
  • The founders stumbled into tequila through the UK bar and nightlife scene, with a plan to open a Mexican-themed tequila and taco bar. An offhand suggestion led to creating their own tequila brand.
    • "The crazy thing is, Sean, the Tequila we got into purely by accident." — John Rainey Jr. [01:34]
• Market Research:
  • Identified the rapid growth in tequila, and opportunities in both premium and flavored segments (inspired by trends in gin, vodka, etc.)
    • Flavors chosen: coffee, vanilla, cinnamon — with coffee selected due to its popularity worldwide, vanilla due to its status as top ice cream flavor, and cinnamon to echo Fireball’s dominance in flavored whiskey.
    • "We wanted to do, you know, eight different expressions... we made our flavors reposado aged, so it's aged in a barrel." — John Rainey Jr. [02:34]

2. Brand Positioning and Product Differentiation

• Premium Approach:
  • Strict focus on quality—no additives, longer-than-standard aging, and use of volcanic water for flavor.
    • "We're not adding anything to it that's not supposed to be added to it." — Rob [24:31]
• Unique Flavors:
  • Most flavored tequilas are made with blanco; Naked Diablo uses aged reposado as the base for its flavors, employing a proprietary method to infuse natural coffee, vanilla, and cinnamon oils.
    • "Our flavors aren't additive aids. They're almost proprietary blends... that's what gives us a leg up." — Rob [19:00]

3. Distribution Strategy & International Expansion

• Sniper Approach vs. Shotgun Approach:
  • The team intentionally concentrated efforts in specific high-potential markets (Florida, Las Vegas) before scaling out, rather than blanket distribution.
    • "Rather than taking a shotgun approach, we decided that we're going to take a sniper approach..." — Rob [04:45]
• Global Rollout:
  • Operations in select US states and recent expansion to the UAE, Dubai, and 27 European countries.
    • "We've just opened up in Europe. So that gives us 27 additional countries." — John Rainey Jr. [05:53]

4. Competition with Celebrity Tequila Brands

• Celebrity Influence:
  • Acknowledgement of the impact A-listers (George Clooney, The Rock, LeBron James, Mark Wahlberg) have in rapidly scaling brands and achieving billion-dollar exits.
    • "Everyone seems to focus on the US market and, and the right to do that... but everywhere around the world is literally going tequila crazy." — John Rainey Jr. [05:52]
    • "That was because of George Clooney, Randy Gerber and these guys..." — John Rainey Jr. [09:50]
    • "Having an A list celebrity behind your brand... goes for something if you're looking to try to create and get out as quickly as possible." — Rob [10:24]
• Naked Diablo's Alternative Path:
  • Emphasis on genuine product quality and documentary-driven storytelling rather than chasing celebrity endorsement.
    • Brand ambassadors like Vanilla Ice promoting the product out of genuine appreciation, not paid arrangements.
    • "We have never had anybody try the liquid that didn't come away and say, if it's not the best, it is up there with the best." — Rob [12:47]

5. Marketing and Media Initiatives

• Award-Winning Documentary:
  • Leveraged as a major differentiator—used documentary filmmaking (“How to Build a Billion Dollar Brand,” available on Amazon Prime) and a reality TV show to generate buzz and credibility.
    • "We got actually asked would we like to do a reality TV show... and that's called how to build a Billion Dollar Brand and that's actually won awards all over the world." — John Rainey Jr. [12:18]
• Brand Story and Trademark Battles:
  • The Naked Diablo name underwent legal opposition in both the US and Europe, but founders were resolute in keeping it for its dual meaning (natural/clean + “Devil” as a fun/boisterous figure).
    • "We created Naked Diablo and we got paused here in the US by naked wines... In Europe... it was Distillery Del Diablo that actually opposed us for the word Diablo." — John Rainey Jr. [23:09]

6. Production Details and Tequila Education

• Regulations and CRT Oversight:
  • Explained the strict regulations governing tequila production, including geographic and ingredient controls.
    • "You can't call it tequila unless it meets these strict guidelines... of the tequila... the commission?" — Rob [07:49]
    • "There's literally people from the CRT that are in there 8–12 hours every single day..." — Rob [08:02]
• Aging and Barrel Process:
  • Longer agave maturation (6–8 years) and barrel aging (minimum 10 months for reposado; 3 years for extra añejo), resulting in smoother, richer flavor profiles.
    • "To get a glass of that will be anywhere between 9 years and 11 years." — John Rainey Jr. [20:00]
    • "That's like a sipping tequila... That's the killer smoke with a cigar." — Rob [20:19]

7. Challenges: Distribution & Launching in a Pandemic

• Navigating Distribution Hurdles:
  • Distribution partners often demand exclusivity or margin but provide little active support.
    • "I'd rather do it myself than give it to a distributor... and all they do is they drive it in a truck to their customer for 35%..." — Rob [32:46]
• COVID Impact:
  • Launched Naked Diablo during COVID-19, facing shutdowns and supply chain problems, hand-labeling bottles to keep the brand moving forward.
    • "We actually rolled out a lot of this while in the midst of COVID..." — Rob [29:13]

8. Broader Spirits Portfolio

• Future Plans and Offerings:
  • The team is also developing award-winning whiskey, vodka, and beer brands to bolster distribution leverage and offer a multi-product approach.
    • "We have a scotch whiskey called Rare Ra, which is an award-winning whiskey... and we also have a healthy drink as well." — John Rainey Jr. [34:22]

Memorable Quotes & Moments

• On their scope and approach:
  • "Go big or go home. You know, obviously it's going to cost a lot more money to set up and drive the business forward." — John Rainey Jr. [20:43]
• On their differentiator:
  • "If it sucks, it sucks. And one thing that we know is we've got the premium product on the market." — Rob [26:38]
• On the tequila craze:
  • "It's the only spirit that is growing. Everything else is contracting." — Rob [33:57]
• On entering a crowded space:
  • "No one else has done it. So we're the first one. We're excited by that and we believe that it will reach millions and millions of people and we will be the next well known tequila brand." — John Rainey Jr. [35:17]

Timestamps for Key Segments

• [01:34] — How accidental origins led to a tequila company
• [02:34] — Choosing flavor profiles and market research
• [04:45] — Strategic market entry and expansion details
• [05:53] — International growth and focus
• [09:50] — Celebrity influence in tequila branding
• [12:18] — Documentary and media-driven branding
• [13:00] — Quality comparisons: Naked Diablo vs. premium benchmarks
• [19:00] — The technical edge of their flavored tequila process
• [20:00] — How aging affects tequila taste and value
• [23:09] — Brand name trademark battles
• [26:38] — The foundation: quality over hype
• [29:13] — Launching and surviving during COVID-19
• [32:46] — Distribution headaches and lessons learned
• [34:22] — Multi-beverage portfolio for the future

Conclusion

This episode provides a candid, entertaining, and in-depth look into the grind behind launching a new beverage brand in a crowded, celebrity-dominated space. The founders of Naked Diablo share their unique strategies, struggles, and wins—highlighting the importance of genuine product quality, storytelling, and adaptive business tactics in a rapidly evolving market.

Recommended for: Aspiring entrepreneurs, beverage industry professionals, and anyone curious about the power (and pitfalls) of branding, distribution, and going up against celebrity-backed conglomerates.