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:

1. How Ashley approached “earning her seat” in the family enterprise
2. Why family meetings (with facilitators) matter more than ever
3. The difference between fighting every battle vs. choosing the right hills
4. How next-gens can bring innovation while honoring legacy
5. What it means to leverage the family office as a tool—not a burden
6. 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.

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