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