Your Next Gen Friend: A Successor's Guide to Business Transition

Andrea Carpenter

Your Next Gen Friend is the podcast for successors—whether you’re stepping into a family business, a privately held company, or simply the expectations tied to someone else’s legacy. I’m Andrea: G2, a successor in a privately owned business, and a guide for the next generation navigating identity, pressure, and purpose inside family systems. This show is for those of us in the in-between... honoring what came before while trying to build something that’s truly our own. Whether you’re blood family or the trusted non-family leader stepping in, this is your space for real conversations about what it actually means to succeed, on your terms. You’re not alone in this. And I hope that makes all the difference.

  1. Entitlement. Isolation. Plans.

    Jun 4

    Entitlement. Isolation. Plans.

    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.

    16 min
  2. How a Fourth-Generation Successor Earned the Keys to a 70-Year-Old Business

    May 21

    How a Fourth-Generation Successor Earned the Keys to a 70-Year-Old Business

    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.

    48 min
  3. Should I Stay or Should I Go? What No One Tells You About Leaving the Family Business

    May 7

    Should I Stay or Should I Go? What No One Tells You About Leaving the Family Business

    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 thereThe 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 thatThree 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 safelyWhen you leave, leave. Don't hover. The people who stay need space to figure out who they are without youLeaving 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.

    44 min
  4. Transition 3.0: Why Successors Need a Seat at the Table

    Feb 12

    Transition 3.0: Why Successors Need a Seat at the Table

    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 3.0Why most transitions fail when communication stops—not when plans failHow successors can gain clarity instead of inheriting vague promisesWhy it’s okay to explore whether leadership is actually what you wantHow Transition 3.0 protects both family relationships and future leadershipDesigning 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

    10 min
  5. Growing Into the Seat While Honoring the Legacy

    Jan 29

    Growing Into the Seat While Honoring the Legacy

    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 enterpriseWhy family meetings (with facilitators) matter more than everThe difference between fighting every battle vs. choosing the right hillsHow next-gens can bring innovation while honoring legacyWhat it means to leverage the family office as a tool—not a burdenHow 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.

    39 min
  6. Designing the Handoff: Clarity, Calm & Co-Leadership with Aviva Kosansky

    Jan 15

    Designing the Handoff: Clarity, Calm & Co-Leadership with Aviva Kosansky

    What if the hardest part of succession isn’t the business strategy—it’s the conversation? In this episode, Andrea talks with Aviva Kosansky, a second-generation leader at ProfitPoint, about what it looks like to step toward ownership when you’re not even sure you want it yet. Aviva shares her early-career detour into fintech, the decision to build real credibility (including earning her Master’s in Supply Chain Management at MIT), and the emotional complexity of working day-to-day with a parent—while also planning for leadership transition with a non-family business partner at the table. If you’ve ever felt stuck between “everyone expects this from me” and “I’m not ready to commit,” Aviva offers something rare: language, structure, and a path to clarity that doesn’t require doing it alone. What You’ll Hear in This Episode: Why “working in the business” and “owning the business” are two completely different decisionsThe simple question Aviva and her dad use to protect their relationship: work talk or personal talk?How a third-party guide changes the entire tone of transition conversationsThe tool that grounded Aviva’s decision-making: the Objectives MatrixWhy clarity creates calm—and how a roadmap beats a rigid plan every timeThe reminder that keeps succession from becoming overwhelming: none of us are essential Connect with Aviva Kosansky: LinkedIn: https://www.linkedin.com/in/avivakosansky/ Company: ProfitPoint – https://profitpt.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. Chapters in this Episode (Audio) 00:00 Introduction: A succession story unfolding in real time 02:31 Aviva’s early career: fintech startup life + the search for flexibility 05:31 The “impromptu job interview” and joining the family business 08:17 The credibility gap: realizing she needed supply chain depth 09:26 MIT during the pandemic + returning with new clarity 10:19 Working with her dad day-to-day (and managing blurred lines) 12:21 “Work conversation or personal conversation?” (a practical boundary tool) 14:05 Expectations vs. desire: “Is this even what I want?” 17:21 The turning point: “We don’t need to struggle through this alone” 20:16 Making the case for a third-party guide (even with a good relationship) 26:03 The Objectives Matrix: grounding priorities + revealing alignment 29:21 When the timeline shifts—and still feels right 32:11 Roadmap vs. plan: preparing for pivots 34:16 What changed after the work: confidence, calm, and clarity 37:53 “None of us are essential”: perspective that reduces overwhelm 40:16 Closing questions: not inheriting everything + honoring being first

    45 min
  7. Naming Growth at the Start of 2026

    Jan 1

    Naming Growth at the Start of 2026

    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 successorsWhy successors get stuck during transitionBreakthrough moments from real family business transitionsThe importance of internal leadership growth and self-regulationWhy growth is the word for 2026How 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

    9 min
  8. No Questions on Sundays: Boundaries, Identity, and Working With Dad in the Family Business

    12/18/2025

    No Questions on Sundays: Boundaries, Identity, and Working With Dad in the Family Business

    What do you do when you’re grateful for your last name… but you don’t want it to be the first thing people see? In this episode, Andrea talks with Brecken Glenn, a next-gen leader at Affinity Partners in Northern Colorado, about the messy middle of stepping into a family business while trying to build your own credibility, confidence, and identity. Brecken shares the defining moment she chose alignment over another credential, how she navigated the fear that people only saw her last name, and the surprisingly practical boundaries she and her dad put in place to protect both the business relationship and the personal one—like calling him “Ryan” in the office, and a rule that still makes her laugh: no questions on Sundays. If you’re a successor trying to lead well and stay whole, this conversation will feel like permission. In this episode, you’ll learn: Why Brecken thought she’d never join the family business—and what changedHow to make an honest ask for a role (without entitlement)What to do with the “am I only here because of my name?” spiralBoundary practices that actually work when you work with a parentWhy succession isn’t an event—it’s a roadmap you adapt as you goWhat it means to be the first woman in your family to step into the role Connect with Brecken Glenn: LinkedIn: https://www.linkedin.com/in/brecken-schaefer/ Company: https://affinityrepartners.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. Chapters in This Episode 00:00 – Welcome + how Andrea and Brecken met (Bailey Program) 03:12 – Brecken’s origin story: “I thought I’d never do real estate” 04:20 – COVID pivot + starting on the brokerage side 06:02 – The honest ask: “Will you make space for me?” 07:52 – The defining moment: choosing herself (and walking away from the master’s) 11:22 – The last-name fear + trying to be “just Brecken” in the room 16:44 – Working with dad: what it’s really like 17:15 – Boundary #1: “Call me Ryan in the office” 18:40 – Boundary #2: “No questions on Sundays” 19:50 – Boundary #3: naming the lens (daughter vs. employee) 22:22 – Holidays + not letting work dominate family space 24:46 – Five years in: confidence, brand, and being seen for contribution 27:25 – Leadership outside the business: ULI + community identity 29:52 – Long runway + patience when the vision is aligned 32:16 – What she’d tell her younger self: you don’t have to have it all figured out 34:24 – Andrea’s transition roadmap metaphor 38:18 – Closing questions: identity, story, and being first11 42:28 – Wrap + invitation to share the podcast

    44 min
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About

Your Next Gen Friend is the podcast for successors—whether you’re stepping into a family business, a privately held company, or simply the expectations tied to someone else’s legacy. I’m Andrea: G2, a successor in a privately owned business, and a guide for the next generation navigating identity, pressure, and purpose inside family systems. This show is for those of us in the in-between... honoring what came before while trying to build something that’s truly our own. Whether you’re blood family or the trusted non-family leader stepping in, this is your space for real conversations about what it actually means to succeed, on your terms. You’re not alone in this. And I hope that makes all the difference.

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