BRAVE COMMERCE: Total Wine & More’s Brian Gelb on Intent-Based Leadership and Retail Growth in a Challenging Alcohol Market

Date: March 3, 2026
Hosts: Rachel Tipograph (MikMak Founder & CEO) and Sarah Hofstetter (Profitero President)
Guest: Brian Gelb, Senior VP of Wine and Concierge at Total Wine & More

Episode Overview

This episode of BRAVE COMMERCE explores how Total Wine & More is bucking the downward trend in the beverage alcohol category, growing sales and market share during turbulent industry times. The spotlight is on Brian Gelb, whose military background and distinctive leadership style provide fresh perspectives on accountability, collaboration between suppliers and retailers, and category innovation. The discussion centers around intent-based leadership, the evolution of the alcohol retail market, and what it means to be “brave” in career and life.

Key Discussion Points & Insights

Insider vs. Outsider Expertise in Business

• Breadth vs. Depth: The hosts kick off with a debate about whether it’s better to be an insider specialist or a knowledgeable outsider in business.
  • Sarah Hofstetter: “You can't lead in disruptive change until you actually understand what's happening... and if you don't have that, then frankly, you don't really stand out.” (03:11)
  • Rachel Tipograph: Reflected on bringing deep eCommerce expertise to First Watch’s board despite no restaurant background: “I could take my deep expertise in one arena and bring it to adjacent categories and have, like, quite an impact by only saying a handful of things.” (04:18)

Brian Gelb’s Background & Military Influence

• Military Values in Business: Brian shares how leading as a young officer shaped his sense of initiative and accountability, contrasting it with typical corporate environments.

  • Brian Gelb: “Here you are as a young military officer, 22, 23 years old, and you're just put in charge of people ... you're expected to lead from day one. ... you’re never given any specific details on how to actually make it happen. ... So it creates, like, an extreme sense of what I would say is, like, ownership and initiative.” (08:48)

• Downsides & Upsides of Military-Style Leadership: While military backgrounds can foster strong ownership, Brian notes this sometimes comes across as aggressive or reckless if not channeled properly. (09:47)

Intent-Based Leadership & Building Accountability

• Cultivating Accountability: Explains “intent-based leadership”—a system where leaders guide employees to think through problems and decisions, building their ownership over outcomes.
  • Brian Gelb: “Anytime somebody brings me a problem, I'm always like, well, what do you want to do?... And I just ask lots of kind of probing questions and it forces people to answer all of those questions and think through their logic. Then we arrive at the end and say, okay, I'm aligned with your decision, let's go do it.” (13:10)
  • Brian Gelb: “That logic forces the decision making down. ... They recognize their owners of the decision. ... they're doing it because they walk through the logic and they believe that that was the right decision for the overall business.” (14:37)

Supplier–Retailer Collaboration

• Bridging Supplier–Retailer Relationships: Brian reflects on his transition from CPG supplier (at Kraft) to retail and shares advice on effective partnerships.
  • Brian Gelb: “The jobs and the roles are not that dissimilar. ... It comes down to the consumer. Everything should be grounded in the customer insights.” (17:48)
  • Brands often have deeper consumer insight data; retailers like Total Wine benefit from this if brands present strategies that align both parties.
  • Collaboration is key: “We're not some big, scary buyer that's pinned behind a wall. Like, let's just sit down and collaborate and solve the consumer problems together. ... If [suppliers] would listen and pay attention first ... then we can find that overlap in that Venn diagram and we can sell more wine together. It's really not that complicated.” (19:53)

Why Total Wine Is Growing While Others Struggle

• Winning with Core Principles:

  • Customer Service Focus: Staff training is paramount—store managers travel to Napa and Europe to understand wine from the source.
    • “We spend a lot of time and a lot of energy training all of our associates so that they can offer great advice and great guidance to customers.” (20:35)
  • Breadth of Selection: Leveraging scale to offer everything from entry-level to ultra-premium, including fast-growing categories like THC-infused and non-alcoholic beverages.
  • Sharp Pricing: “We try to be really laser focused on having sharp prices ... we don’t ever want to be undersold versus competition.” (23:54)
  • Store Experience: Clean, modern stores—a notable shift from the “dirty and sleazy” liquor stores of decades past.
  • Category Innovation: Growth in THC-infused, non-alcoholic, and functional beverages (e.g., lion’s mane, ashwagandha drinks).
    • “When I joined Total Wine, there were three categories: wine, beer and spirits. And now ... it’s like an infinite number of categories along a continuum.” (24:30)

• Market Offense vs. Defense:

  • Rachel Tipograph: “You guys are playing offense while a lot of other people are playing defense. ... It'll be interesting if they start to copy the Total Wine strategy.” (25:33)

Career and Life Lessons on Bravery

• On Bravery:
  • Brian Gelb: Cites personal rather than professional bravery—moving in with his wife for the first time a year after marriage: “I think the one that I came up with ... is when I went on my honeymoon with my wife, it was the longest amount of time I'd ever spent with her.” (26:11)

Notable Quotes & Memorable Moments

• On Intent-Based Leadership:
  Brian Gelb: “They're not going to walk out of my office saying, ‘Well, we're doing this because Brian told us to do it.’ They're doing it because they walk through the logic and they believe that that was the right decision for the overall business.” (14:37)

• On Collaboration:
  Brian Gelb: “Let's just sit down and collaborate and solve the consumer problems together. I mean, that's really what it boils down to. ... If they would listen and pay attention first ... then we can find that overlap and that Venn diagram and we can sell more wine together. It's really not that complicated.” (19:53)

• On Alcohol Industry Evolution:
  Brian Gelb: “When I joined Total Wine, there were three categories. ... And now ... it’s like an infinite number of categories along a continuum.” (24:30)

• On Growth Strategy:
  Rachel Tipograph: “Total Wine seems to be growing when the alcohol and spirits category is struggling. ... What's going on and what are we missing?” (20:31)

• On Bravery in Life:
  Brian Gelb: “I've lived in, like, four countries in my life. I've changed career arc so many times, and at some point, it just becomes who you are as a person.” (26:11)

Key Timestamps

• 03:11 – Sarah on the value of industry depth in business
• 08:48 – Brian on military leadership, initiative, and its impact on business
• 13:10 – Intent-based leadership explained
• 17:48 – Supplier–retailer partnerships and consumer insight sharing
• 19:53 – The Venn diagram of shared goals in supplier–retailer relationships
• 20:35 – Ingredients of Total Wine’s growth: service, assortment, pricing
• 24:30 – Expanding beverage categories beyond tradition
• 26:11 – Brian's most "brave" moment: marrying his wife

Takeaways for Listeners

• Intent-based leadership empowers teams, creates real accountability, and drives better decisions—encouraging “ownership” at every level.
• Effective supplier–retailer partnerships are built on open collaboration—where insights, strategy, and mutual goals overlap for shared success.
• Growth in a challenging market is possible by sticking to core principles: excellent service, exceptional product range, competitive pricing, and constantly innovating around customer needs.
• Industry disruption often comes not from radically new technology, but from a focused, customer-first approach and willingness to rethink traditional categories.
• Bravery in business and life may look different for everyone: sometimes a major move, sometimes a total life pivot, sometimes just sharing a home for the first time.

End of summary.