What happens when you grow up knowing your family is comfortable but nobody ever tells you what that actually means? And then one day in your thirties, you start learning about trusts and structures and tax implications that have been there the whole time?

Celine Fitzgerald lived that. She's a G3 family member whose dad was CEO of their family's bank when a liquidity event happened in 1994. She was eight. Everyone kind of went their own way after that, and the conversation about what it all meant just never really happened. Celine spent her twenties in New York and Milan, working in fashion and luxury retail, and it wasn't until she went back for her MBA at 31 that she stumbled into the world of family business, family office, and wealth stewardship.

In this episode, Andrea and Celine talk about what it's like to be an unprepared inheritor and the steep learning curve that comes with it. They get into the entitlement myth (spoiler: neither of them has ever met an entitled rising gen), what it looks like to bring a spouse into the family enterprise, and why communication and having grace for the leading gen might be the most important things you can practice this week.

Key takeaways from this episode:

• Being an unprepared inheritor is more common than you'd think, and the learning curve in your thirties is steep when nobody talked about it earlier
• The rising gens showing up to do this work aren't entitled. They want to be seen, heard, and given a chance to be responsible stewards
• If you don't know what's in your trust or how it impacts your life, you're allowed to ask. Frame it around education and what you're learning on your own
• Integrating a spouse into the family enterprise is deeply personal and every family does it differently, but openness early on makes everything easier
• Leading gens often don't know where to start either. Sometimes your questions actually take pressure off of them
• Have grace for the generation above you. They're doing this without a playbook too

Connect with Celine Fitzgerald

Linkedin: https://www.linkedin.com/in/celine-fitzgerald-3603a18/

In Three Generations Website: https://www.inthreegenerations.com/

Connect with Andrea Carpenter and Your Next Gen Friend:

Website: https://yournextgenfriend.com

Instagram: https://www.instagram.com/yournextgenfriend/

YouTube: https://www.youtube.com/@yournextgenfriend

LinkedIn: https://www.linkedin.com/in/andreashaver/

Subscribe to Your Next Gen Friend on your favorite podcast player:

Spotify: https://yournextgenfriend.com/open-spotify

Apple Podcasts: https://yournextgenfriend.com/apple-podcast

Podcast theme music by Transistor.fm.

Season 2 is here. Andrea kicks things off solo with a look at what she's been hearing from next gens over the past year, across dozens of calls and conversations.

Three patterns keep showing up.

The first is the entitlement myth. Parents and founders worry their kids will feel entitled to the business or the wealth. But when Andrea sits down with next gens, the feelings underneath are almost always shame, guilt, and confusion. Jake Knight put it directly: the next gens he meets don't feel they deserve anything. They don't even know how to talk about it with their friends. When curiosity gets labeled as entitlement, next gens stop asking questions altogether, and that's when they actually end up unprepared.

The second pattern is isolation. Wealth, inheritance, family business dynamics: these aren't things most people can bring up with their college roommate or their coworker. Andrea shares her own experience of meeting her first real peer at a Tiger 21 conference and the relief of realizing someone else understood. That same feeling has come up with Evolve clients who are non-family successors buying into a business. The "you get this too?" moment matters more than most people realize.

The third pattern is about clarity. Successors aren't asking for a polished strategy deck. They want any plan at all. One discovery call participant said they just wanted to know if there's something with thought behind it, instead of being completely in the dark. Andrea connects this to the entitlement theme: asking for a roadmap can feel like overstepping, so people stop asking, and that's when disengagement starts. TTS uses tools like timelines, objectives, and matrices in Evolve to get everything on the table so successors can make informed decisions about their participation.

Andrea closes with a reminder: if you're a successor, you're not the only one. That's the whole point of this podcast.

Connect with Andrea: Instagram DM or email at yournextgenfriend@gmail.com

Book a 30-minute call to talk through how to position these conversations in your family.

Connect with Andrea Carpenter and Your Next Gen Friend:

Website: https://yournextgenfriend.com

Instagram: https://www.instagram.com/yournextgenfriend/

YouTube: https://www.youtube.com/@yournextgenfriend

LinkedIn: https://www.linkedin.com/in/andreashaver/

Subscribe to Your Next Gen Friend on your favorite podcast player:

Spotify: https://yournextgenfriend.com/open-spotify

Apple Podcasts: https://yournextgenfriend.com/apple-podcast

Podcast theme music by Transistor.fm.

What happens when the family business you joined for the long haul loses a huge piece of its revenue, and you are the one who has to figure out what comes next?

In this Season 2 premiere of Your Next Gen Friend, Andrea sits down with Josh Robinson, fourth-generation owner of Argonaut Liquor in Denver. Josh shares how he went from stocking shelves and choosing not to lead with his last name, to leading the business through COVID, a brutal ballot initiative that cut wine volume by 60%, and a family ownership transition that tested every relationship in the building. Along the way he stood up a weekly executive meeting, brought Unreasonable Hospitality into the team's rhythm, and learned (sometimes the hard way) why ownership conversations cannot wait.

Key takeaways from this episode:

• Starting at the bottom is not just about humility. It builds the operational knowledge and relationships you will lean on when it is your turn to lead.
• Earning trust and respect from long-tenured employees takes real time, and there are no shortcuts, even when your name is on the building.
• COVID accelerated Josh's path into leadership and gave him the chance to prove his value when the stakes were highest.
• When market forces change your business model overnight, the operational habits and team trust you built in better years become your survival playbook.
• The biggest regret in Josh's transition was not having the hard ownership conversations early. When urgency shows up, hard conversations turn into painful ones.
• A weekly exec meeting and a shared read of Unreasonable Hospitality changed how the whole organization communicated and gave the team permission to row in the same direction.

Connect with Josh Robinson:

Linkedin: https://www.linkedin.com/in/joshua-robinson-401739ba/

Argonaut Liquor: https://www.argonautliquor.com/

Connect with Andrea Carpenter and Your Next Gen Friend:

Website: https://yournextgenfriend.com

Instagram: https://www.instagram.com/yournextgenfriend/

YouTube: https://www.youtube.com/@yournextgenfriend

LinkedIn: https://www.linkedin.com/in/andreashaver/

Subscribe to Your Next Gen Friend on your favorite podcast player:

Spotify: https://yournextgenfriend.com/open-spotify

Apple Podcasts: https://yournextgenfriend.com/apple-podcast

Podcast theme music by Transistor.fm.