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:

1. Why “working in the business” and “owning the business” are two completely different decisions
2. The simple question Aviva and her dad use to protect their relationship: work talk or personal talk?
3. How a third-party guide changes the entire tone of transition conversations
4. The tool that grounded Aviva’s decision-making: the Objectives Matrix
5. Why clarity creates calm—and how a roadmap beats a rigid plan every time
6. The 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 +...

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:

1. What Andrea noticed again and again in conversations with successors
2. Why successors get stuck during transition
3. Breakthrough moments from real family business transitions
4. The importance of internal leadership growth and self-regulation
5. Why growth is the word for 2026
6. 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 +

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.

What does clarity really look like in a family business?

In this episode, Andrea talks with third-generation leader Adam Hatcher, who shares how a simple letter from his father set the standard for joining the family firm—and why that decision changed everything. Together they unpack the complex mix of love, loyalty, and leadership that defines multi-generational companies and the systems that help them thrive.

If you’ve ever wondered how to enter your family business without losing yourself in it, this conversation will feel like a mirror.

What You’ll Hear in This Episode:

• The five criteria Adam’s father required before any child could join the business
• Why clarity and systems protect relationships as much as profits
• How to avoid “drifting into” the family company by default
• The difference between being family-fit and role-fit
• What happens when unconditional love meets conditional business realities
• The conversation that aligned ambition, faith, and growth at $200 million in revenue

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 happens when successors finally have a system that helps them lead with clarity instead of chaos?

Andrea sits down with Adam Hill and Jacqueline Jensen to explore how EOS (the

Entrepreneurial Operating System) changed their leadership—and their companies.

You’ll hear their origin stories in family business, what EOS made possible, and their favorite

tools (V/TO, Issues Solving Track, Scorecard). Together they sketch a people-first picture of EOS: structure that actually liberates successors to lead with confidence, communicate honestly, and build healthy teams.

What You’ll Hear in This Episode:

• Adam’s turnaround story: from near insolvency to aligned, profitable growth on EOS.
• Jacqueline’s shift from 80-hour weeks to a thriving, people-first culture through self-implementation.
• Why structure → freedom: EOS as bumpers that keep vision and values on track.
• Favorite tools that changed their leadership (V/TO, IDS/Issues Solving Track, Scorecard).
• How EOS separates relationships from roles so families can lead—and love—better.

Connect with Adam Hill:

Email: adam.hill@eosworldwide.com

Connect with Jacqueline Jensen:

Email: jacqueline.jensen@eosworldwide.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.

What does it mean to be Generation 1.5—old enough to remember the drywall dust, young enough to build the next playbook?

At just 20 years old, JR runs leasing at Victory Real Estate Group, sits at city council meetings for development projects, and co-founded NextGenX—a peer group for successors who know legacy is about people, not just money. He also launched Retail Equity, introducing capital raising to a business his father built without outside capital.

This episode dives into succession in motion, the courage to pitch innovation to the founder, and why “relational, not transactional” might be the most important mindset for the next generation.

You’ll hear:

• JR’s father’s rags-to-riches story and why it fuels his work ethic.
• Why weekends on job sites shaped JR’s identity as Generation 1.5.
• The early succession moves at Victory: bringing in a CFO and COO.
• How JR pitched capital raising to his dad—and why it stuck.
• Why curated peer groups are the future of successor learning.

Connect with Jahan “JR” Ramji:

Victory Real Estate Group: victoryrealestategroup.com

NextGenX: thenextgenx.com

LinkedIn: linkedin.com/in/jahanramji

For Victory Group & Retail Equity inquiries, I can be reached at jr@vg-re.com

For NextGenX inquiries, I can be reached at jr@thenextgenx.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.