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.

If you work in your family's business, there's something worth sitting with: one day, you won't. Whether you're the one leaving or watching someone else step away, a parent, a sibling, a cousin, it's going to happen. And the emotional weight of that exit is unlike anything you'll go through in any other job.

In this Part 2 conversation, Andrea sits back down with Adam Hatcher, family business consultant, former 13-year veteran of his own family's company, and author of The Chaos Proof Family Business. They get into the question that keeps successors up at night: should I stay or should I go? Adam shares the framework he uses with families to evaluate whether the business can still give you what you need, why family meetings were the only place where his own exit could unfold as a process instead of a crisis, and what it felt like to walk down the stairs of the family company for the last time, following the same steps his grandfather once walked.

Key takeaways from this episode:

• If you work with your family, your exit is inevitable. Even if the company continues, one day you won't be there
• The emotional impact of leaving a family business falls somewhere between a normal job loss and a family loss, and most people aren't prepared for that
• Three questions to check in with yourself: Is there a future here that excites you? Can you do your job wholeheartedly? Are you being rewarded, recognized, and developed?
• Family meetings, separate from executive meetings, are where the honest conversations about staying or going can happen safely
• When you leave, leave. Don't hover. The people who stay need space to figure out who they are without you
• Leaving is not the opposite of loyalty. Sometimes making space is the most loyal thing you can do

If you haven't listened to Part 1, start there. We'll link it below. Adam covers how he joined, how they scaled, and what it's like working across three generations.

Connect with Adam Hatcher:

Website: https://21clear.com

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

Adam’s Newsletter: https://21clear.substack.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.

What if succession planning wasn’t something that happened to you—but something you helped design?

In this solo episode, Andrea introduces Transition 3.0, a modern approach to family business and wealth transitions that gives successors a real seat at the table. Instead of vague promises or plans revealed too late, Transition 3.0 focuses on clarity, collaboration, and honest conversation—before resentment builds and relationships strain.

Andrea breaks down the differences between Transition 1.0, 2.0, and 3.0, explains why communication—not legal structure—is the biggest predictor of success, and shares why this model protects both leadership readiness and family relationships. If you’re a rising generation wondering whether this path is truly right for you, this episode will help you understand what you’re actually saying yes to.

What You’ll Hear in This Episode:

• The evolution from Transition 1.0 to Transition 3.0
• Why most transitions fail when communication stops—not when plans fail
• How successors can gain clarity instead of inheriting vague promises
• Why it’s okay to explore whether leadership is actually what you want
• How Transition 3.0 protects both family relationships and future leadership
• Designing a legacy that honors the past without copying it

Connect with Andrea Carpenter and Your Next Gen Friend:

Website: https://yournextgenfriend.com/

Your Next Gen Friend on Instagram: https://www.instagram.com/yournextgenfriend/

Your Next Gen Friend on Youtube: https://www.youtube.com/@yournextgenfriend

Andrea on 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.

Chapters in this Episode

00:00 Why Transition 3.0 Matters Now

01:45 Transition 1.0: When Planning Happened in Silence

02:55 Transition 2.0: Communicating the Plan

04:05 What Makes Transition 3.0 Different

05:10 Why Communication Is the Real Risk

06:35 Clarity Before Commitment for Successors

07:45 Designing Legacy Without Being a Carbon Copy

08:40 Closing Reflection & Invitation

What does it really mean to earn your seat in a family enterprise—especially when legacy, identity, and personal ambition are all intertwined?

In this candid conversation, Andrea talks with Ashley Dimond about growing into leadership inside her family’s operating company, family office, and foundation. Ashley shares how business school helped her fight the “nepotism cloud,” why family meetings became a cornerstone of healthy transition, and how becoming a mother reshaped how she thinks about work, legacy, and time.

This episode is a must-listen for next-gens navigating earned authority, innovation vs. tradition, and the emotional complexity of succession.

In this episode, you’ll learn:

• How Ashley approached “earning her seat” in the family enterprise
• Why family meetings (with facilitators) matter more than ever
• The difference between fighting every battle vs. choosing the right hills
• How next-gens can bring innovation while honoring legacy
• What it means to leverage the family office as a tool—not a burden
• How motherhood is reshaping Ashley’s vision of leadership and legacy

Connect with Ashley Dimond:

Linkedin: https://www.linkedin.com/in/dimondashley/

Copford Capital Management: https://copfordcm.com/

Connect with Andrea Carpenter and Your Next Gen Friend:

Website: https://yournextgenfriend.com/

Your Next Gen Friend on Instagram: https://www.instagram.com/yournextgenfriend/

Your Next Gen Friend on Youtube: https://www.youtube.com/@yournextgenfriend

Andrea on 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.

The year has come to a close—and with it, a lot of reflection.

In this short solo episode, Andrea shares what the past year revealed through her work with successors, the conversations that stayed with her, and the growth she’s witnessed both in others and in herself. From navigating responsibility and identity to realizing how much internal leadership work transitions require, this episode names what so many successors are feeling but often struggle to put into words.

Andrea walks through several real transition moments she observed this year: a successor who moved from uncertainty into actively pushing on a transition, another who focused deeply on internal leadership work, and a large sibling group that found clarity through honest conversations about who wanted to stay and who didn’t. These stories highlight how different every path can be and how growth shows up in many forms.

She also shares her word for the year ahead—growth—and explains how The Transition Strategists have evolved their work, including the launch of the Evolve program, designed to support successors and families through transition together.

What You’ll Hear in This Episode:

• What Andrea noticed again and again in conversations with successors
• Why successors get stuck during transition
• Breakthrough moments from real family business transitions
• The importance of internal leadership growth and self-regulation
• Why growth is the word for 2026
• How The Transition Strategists are evolving their work with families

Connect with Andrea Carpenter and Your Next Gen Friend:

Website: https://yournextgenfriend.com/

Your Next Gen Friend on Instagram: https://www.instagram.com/yournextgenfriend/

Your Next Gen Friend on Youtube: https://www.youtube.com/@yournextgenfriend

Andrea on 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.

Chapters in This Episode

00:00 End of Year Reflection

00:45 What This Year Revealed for Successors

01:45 Breakthroughs in Real Transitions

03:30 Naming Growth for 2026

04:20 How Our Work Is Evolving

05:30 Closing Reflection and Invitation