Social Shifts & Scaling Spirits: Gen Z, Global Brands, and Career Risks

Join Molly Baker and our guest for a candid conversation on Gen Z social habits, global brand building, and the career risks that shape long-term growth. Drawing on her experience leading liqueurs at Diageo, Olivia shares what it takes to integrate and scale brands across markets, navigate shifting consumer behavior, and lead teams with clarity in a fast-changing industry. Together, they explore the evolving role of alcohol in Gen Z social life, the realities of burnout and boundary-setting, and why mentorship, self-awareness, and taking more risks can be some of the most powerful career tools. Whether you’re building a brand, leading a team, or rethinking your own path, this episode offers an honest look at leadership, reinvention, and growth in a changing world.

MB (Molly Baker) : What’s top of mind for you professionally right now?
OK (Olivia Kupfer) : Probably whether what I do is going to exist and what it’s going to look like in five years. I’m optimistic. I think there will always be extremes, whether it’s health and wellness or indulgence. But how big it is and how much it changes, I don’t know.

MB: There’s a lot of conversation around Gen Z and socializing. What are you seeing?
OK: Gen Z is social, but how they socialize is really different. They’ve spent a lot of time online and had years of COVID, so they’re less comfortable in those environments. They still want to socialize, but what that includes and where it happens is different. In beverage alcohol, it plays a different role. Some are not drinking at all or drinking less frequently, and when they do, they’re more intentional.

MB: What are you really good at?
OK: I’m good at building relationships. I can talk to anyone and find common ground. It’s been a huge advantage, especially at work, and it’s helped me build a really strong network.

MB: What’s been a pivotal moment in your career?
OK: Taking on a role where I had real responsibility for business performance. It matched my ambition, but it was a ton of work. I definitely overinvested and burned out. But I needed that experience because before that, I thought I had endless capacity and could just keep adding more.

MB: How has your perspective on work changed since then?
OK: I’m much more intentional now. Not everything is valued equally. I’m more choiceful about what I take on, and I say no more. I prioritize my time and my team’s time much better than I used to.

MB: What advice would you give your younger self?
OK: Take more risks. The cost is so low when you’re younger. You can do almost anything and still have time to restart. I wish I had been bolder.

MB: What’s been most important in your career growth?
OK: Mentorship and relationships. I’ve had people advocate for me at every stage, but those relationships happened organically. I invested in them over time, and that turned into mentorship. That’s been incredibly valuable.

MB: What’s been the biggest shift in how you think about leadership?
OK: I focus more on clarity and prioritization. I want people to feel heard, but I’m decisive. I try to push for excellence and help people realize that they’re capable of more. At the same time, the hardest part is managing people, their expectations, and making sure you’re helping them grow while also meeting the needs of the business.

MB: What’s something you’ve learned the hard way?
OK: Be careful what you’re good at. People will take advantage of that. If you’re high capacity, more will keep coming your way, so you have to set boundaries and be intentional about where you spend your energy.

MB: What keeps you excited about the future?
OK: The idea that things will keep changing. Whether it’s consumer behavior, AI, or even my own career, I think there’s always going to be something new to figure out. I like the idea that I might end up doing something completely different down the line.

MB: You mentioned working globally. How do you think about global strategy versus local markets?
OK: It’s probably a bit more US-led than it should be, but we really try to start with the consumer. What do people want and how are they using the product? Strategy often starts in the US, then gets adapted depending on the market. Coffee culture, cocktail culture, all of that varies so much, so you can’t just copy and paste. It has to flex based on what’s happening locally.

MB: What does your day-to-day actually look like?
OK: Honestly, I spend a lot of time on the phone. My role is global, so I’m talking to teams in different markets, commercial partners, and my own team. It’s a lot of communication, planning, and building.

MB: You’ve helped integrate a brand into a large organization. What was that like?
OK: It’s so hard. Bringing a startup into a company that size touches everything, the team, processes, supply chain, how you train people to sell it. We thought it would take a year, and it took longer. There are so many details you don’t think about until you’re in it.

MB: And you built the team from scratch too?
OK: Yes, there was no team when I joined. We had to build everything. It was a lot, but it also makes me really proud of what we’ve done over the last few years.

MB: How has that experience shaped how you lead today?
OK: I’d describe my leadership style as a pacesetter. I want people to feel heard, but I’m not trying to build consensus on everything. I’m decisive, and I have high standards. The focus is on delivering excellent work and helping people realize they’re capable of it.

MB: What do you find most challenging about leading a team?
OK: The people side. Managing expectations, motivations, and feelings is always the hardest part. Everyone wants something different, and sometimes those things don’t align with what the business needs. That’s tough to navigate.

MB: But also the most rewarding?
OK: Definitely. When it works, it’s incredibly rewarding. I love investing in people, building relationships, and seeing them grow into their own careers.

MB: You’ve had a lot of mentors throughout your career. How did those relationships come about?
OK: Mostly organically. I never formally asked someone to be my mentor. I built relationships over time, and then those naturally turned into mentorship. I think that works better because there’s already trust and connection.

MB: Do you think mentorship changes over time?
OK: Absolutely. Your needs change at different stages of your career, so the people you go to for advice can change too. It’s not always one person forever.

MB: Looking back, what’s one mindset shift that made the biggest difference for you?
OK: Realizing that it’s okay to change. You don’t have to keep escalating your commitment to something just because you started it. You can walk away, reprioritize, and choose differently. That was a big shift for me.

MB: And finally, what’s your outlook on the future, whether it’s AI or social behavior?
OK: Everything is going to change, whether it’s AI or how people socialize. But I think that’s exciting. There will always be something new to figure out, and I like the idea that I might end up doing something completely different down the line.

Find Olivia on Linkedin and Instagram or visit the Diageo website!

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