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:

1. The evolution from Transition 1.0 to Transition 3.0
2. Why most transitions fail when communication stops—not when plans fail
3. How successors can gain clarity instead of inheriting vague promises
4. Why it’s okay to explore whether leadership is actually what you want
5. How Transition 3.0 protects both family relationships and future leadership
6. 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:

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 +...