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

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 changed
• How to make an honest ask for a role (without entitlement)
• What to do with the “am I only here because of my name?” spiral
• Boundary practices that actually work when you work with a parent
• Why succession isn’t an event—it’s a roadmap you adapt as you go
• What 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

What really happens when the business you’re buying belongs to your parents — and everyone has an opinion about what’s “fair”?

Today’s episode dives into the emotional, operational, and relational reality of third-generation succession with Mitch Gambert, the new owner of Gambert Shirts, a legacy American shirtmaker in Newark, NJ.

If you’re in the thick of a transition — managing expectations, navigating sibling fairness, or trying to separate family identity from business decisions — this episode will feel like a deep exhale.

Mitch shares candidly about the years-long process of structuring his buyout, the emotional push-pull with his parents, and why succession feels like starting over… even after 20+ years in the business.

In this episode, you’ll learn:

• How Mitch found his way back into the business after 9/11
• The moment he realized he wanted to buy the company
• Why sibling fairness became the hardest emotional layer
• The importance of facilitated conversations and strong legal teams
• What Mitch wishes more successors understood about “starting over”
• What he’s building now as the third-generation owner

________________________________________

Connect with Mitch Gambert:

Website: https://gambertshirts.com

Email: mitchg@gambertshirts.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

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 – Episode open + host intro

01:00 – Mitch joins the conversation

02:15 – Growing up in the factory & the multigenerational origin story

05:20 – The journey back after 9/11: choosing the family business

08:35 – When the idea of buying the company actually began

10:15 – Navigating sibling equity, fairness, and future upside

12:30 – The emotional push-pull with parents during negotiations

15:40 – Why facilitated conversations mattered

18:45 – “Starting over” at 52 and the realities of third-generation transition

22:48 – The hardest part: separating emotion from business

25:50 – What went well and what Mitch would recommend to others

28:10 – What’s next for Gambert Shirts

31:00 – Reflection Round: Andrea’s three signature questions

33:40 – Close + outro

Ever felt like you’re wearing someone else’s leadership suit? In family business, it’s easy to inherit roles, patterns, and assumptions that don’t fit. In this solo episode, Andrea breaks down the IMAP assessment—a practical framework to name your natural wiring so you can lead with clarity (not copycat energy).

You’ll learn how motivated roles map to a project’s lifecycle (Idea → Prototype → Develop → Refine → Maximize), why operating outside your role drains energy, and how temperament and impact style shape the way you show up.

What You’ll Hear in This Episode

• The 5 motivated roles and how to find yours across a project’s lifecycle
• Why “not my role” ≠ weakness—and how role-misalignment mimics burnout
• Andrea’s wiring (Refiner/Maximizer, Internal Futurist, Feeler-Planner, Analyst) and how it shows up in client work
• Practical scripts for teammates with different temperaments (planner vs. adapter, internal vs. social)
• How successors can design roles that fit them—not just the previous leader
• Invite: Fall IMAP cohort for successors who want to apply this in community

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.