You're Going to Sit on the Opposite Side of the Table From Someone You Love

Not an Inheritor. A Steward: Alex Radler on Identity, Wealth, and What Comes Next

What if the label "Gen 2" was never the point? In this episode, Andrea Carpenter sits down with Alex Radler, who grew up watching his family's wealth multiply through oil, gas, and real estate, and who spent his teenage years chasing the next car, the next party, the next thing, before a DUI at 22 sent him to Uganda and South Sudan for a year of service that changed everything. Alex opens up about the fractured relationship he had with his father growing up, the counseling it took to get to real forgiveness, and the moment on a trip to Africa when his dad finally told him he was proud of him, not for a smart investment, but for who he'd become. Andrea and Alex get into what it actually means to be a steward rather than an inheritor: how that shows up across five areas (money, time, network, influence, and wisdom), why patience matters more than speed when it comes to real impact, and what Alex tells young leaders in Africa about identity before anything else. They close with concrete advice for any next gen still waiting on access to family wealth: get honest people around you, root your choices in who you are before what you'll inherit, and don't let comfort become the whole goal. Connect with Alex Radler Linkedin: https://www.linkedin.com/in/alexander-r-b1583b97/ [https://www.linkedin.com/in/alexander-r-b1583b97/] The Radler Foundation: http://radlerfoundation.org/ [http://radlerfoundation.org/] Connect with Andrea Carpenter and Your Next Gen Friend: Website: https://yournextgenfriend.com [https://yournextgenfriend.com/] Instagram: https://www.instagram.com/yournextgenfriend/ [https://www.instagram.com/yournextgenfriend/] YouTube: https://www.youtube.com/@yournextgenfriend [https://www.youtube.com/@yournextgenfriend] LinkedIn: https://www.linkedin.com/in/andreashaver/ [https://www.linkedin.com/in/andreashaver/] Subscribe to Your Next Gen Friend on your favorite podcast player: Spotify: https://yournextgenfriend.com/open-spotify [https://yournextgenfriend.com/open-spotify] Apple Podcasts: https://yournextgenfriend.com/apple-podcast [https://yournextgenfriend.com/apple-podcast] Our Sister Show: The Business Transition Roadmap Hosted by Elizabeth Ledoux, The Business Transition Roadmap is for business owners navigating succession, from the first conversation about what's next to the handoff itself. If you're the leading generation in this transition, this show is for you. Spotify: https://open.spotify.com/show/3ddKWcqvaXd7hdsdzc2tWk [https://open.spotify.com/show/3ddKWcqvaXd7hdsdzc2tWk] Apple Podcasts: https://apple.co/3IhMMux [https://apple.co/3IhMMux] Podcast theme music by Transistor.fm.

You're Going to Sit on the Opposite Side of the Table From Someone You Love

There's a moment in every family business transition where you're going to look at someone you love and realize you want something different than what they want. Not in a small way. In a way that makes the whole deal feel like it might not work. That's what this episode is about. Andrea recorded this one solo after leading an Evolve Group Lab on the same topic that morning. She walks through what it means to sit on opposite sides of the table from someone in your family or your business, why that's not only normal but inevitable if your transition is a real one, and what happens when people stop talking because they're afraid of the disagreement. She also gets into the specific tensions that show up on each side. Transitioners are dealing with identity, security, control, and the fear of letting go. Successors are dealing with autonomy, financial pressure, confidence, and the fear of disappointing people. And a lot of the time, neither side realizes what the other is carrying. Andrea shares a personal example from her own transition with Elizabeth and offers a reframe that might change how you approach your next hard conversation: it's not me versus you. It's us versus the problem. Key takeaways from this episode: * If your transition is a real transition, you are going to end up on opposite sides of the table from someone you care about. That's not a sign something is wrong * The table isn't always two-sided. Multiple successors, married co-owners, and business partners can all be sitting at different angles with different priorities * Transitioners carry fears around identity, security, legacy, and control. Successors carry fears around autonomy, finances, capability, and disappointing people * When tension shows up, people tend to walk away from the table, crawl under it, or lunge over it. None of those responses move the transition forward * The most dangerous thing isn't disagreement. It's when people stop talking and assumptions start to fill the gaps * When someone gives you a hard no, stay curious about what's underneath it. Treat it like a door, not a wall * You don't have to figure out buy-sell agreements and valuations with lawyers first. You can work through the important pieces on your own or with a transition guide before you bring in the legal team Connect with Andrea: Instagram DM or email at yournextgenfriend@gmail.com [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 [https://yournextgenfriend.com/] Instagram: https://www.instagram.com/yournextgenfriend/ [https://www.instagram.com/yournextgenfriend/] YouTube: https://www.youtube.com/@yournextgenfriend [https://www.youtube.com/@yournextgenfriend] LinkedIn: https://www.linkedin.com/in/andreashaver/ [https://www.linkedin.com/in/andreashaver/] Subscribe to Your Next Gen Friend on your favorite podcast player: Spotify: https://yournextgenfriend.com/open-spotify [https://yournextgenfriend.com/open-spotify] Apple Podcasts: https://yournextgenfriend.com/apple-podcast [https://yournextgenfriend.com/apple-podcast] Podcast theme music by Transistor.fm.

I Was an Unprepared Inheritor and I'm Not the Only One

What happens when you grow up knowing your family is comfortable but nobody ever tells you what that actually means? And then one day in your thirties, you start learning about trusts and structures and tax implications that have been there the whole time? Celine Fitzgerald lived that. She's a G3 family member whose dad was CEO of their family's bank when a liquidity event happened in 1994. She was eight. Everyone kind of went their own way after that, and the conversation about what it all meant just never really happened. Celine spent her twenties in New York and Milan, working in fashion and luxury retail, and it wasn't until she went back for her MBA at 31 that she stumbled into the world of family business, family office, and wealth stewardship. In this episode, Andrea and Celine talk about what it's like to be an unprepared inheritor and the steep learning curve that comes with it. They get into the entitlement myth (spoiler: neither of them has ever met an entitled rising gen), what it looks like to bring a spouse into the family enterprise, and why communication and having grace for the leading gen might be the most important things you can practice this week. Key takeaways from this episode: * Being an unprepared inheritor is more common than you'd think, and the learning curve in your thirties is steep when nobody talked about it earlier * The rising gens showing up to do this work aren't entitled. They want to be seen, heard, and given a chance to be responsible stewards * If you don't know what's in your trust or how it impacts your life, you're allowed to ask. Frame it around education and what you're learning on your own * Integrating a spouse into the family enterprise is deeply personal and every family does it differently, but openness early on makes everything easier * Leading gens often don't know where to start either. Sometimes your questions actually take pressure off of them * Have grace for the generation above you. They're doing this without a playbook too Connect with Celine Fitzgerald Linkedin: https://www.linkedin.com/in/celine-fitzgerald-3603a18/ [https://www.linkedin.com/in/celine-fitzgerald-3603a18/] In Three Generations Website: https://www.inthreegenerations.com/ [https://www.inthreegenerations.com/] Connect with Andrea Carpenter and Your Next Gen Friend: Website: https://yournextgenfriend.com [https://yournextgenfriend.com/] Instagram: https://www.instagram.com/yournextgenfriend/ [https://www.instagram.com/yournextgenfriend/] YouTube: https://www.youtube.com/@yournextgenfriend [https://www.youtube.com/@yournextgenfriend] LinkedIn: https://www.linkedin.com/in/andreashaver/ [https://www.linkedin.com/in/andreashaver/] Subscribe to Your Next Gen Friend on your favorite podcast player: Spotify: https://yournextgenfriend.com/open-spotify [https://yournextgenfriend.com/open-spotify] Apple Podcasts: https://yournextgenfriend.com/apple-podcast [https://yournextgenfriend.com/apple-podcast] Podcast theme music by Transistor.fm.

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 [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 [https://yournextgenfriend.com/] Instagram: https://www.instagram.com/yournextgenfriend/ [https://www.instagram.com/yournextgenfriend/] YouTube: https://www.youtube.com/@yournextgenfriend [https://www.youtube.com/@yournextgenfriend] LinkedIn: https://www.linkedin.com/in/andreashaver/ [https://www.linkedin.com/in/andreashaver/] Subscribe to Your Next Gen Friend on your favorite podcast player: Spotify: https://yournextgenfriend.com/open-spotify [https://yournextgenfriend.com/open-spotify] Apple Podcasts: https://yournextgenfriend.com/apple-podcast [https://yournextgenfriend.com/apple-podcast] Podcast theme music by Transistor.fm.

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/ [https://www.linkedin.com/in/joshua-robinson-401739ba/] Argonaut Liquor: https://www.argonautliquor.com/ [https://www.argonautliquor.com/] Connect with Andrea Carpenter and Your Next Gen Friend: Website: https://yournextgenfriend.com [https://yournextgenfriend.com/] Instagram: https://www.instagram.com/yournextgenfriend/ [https://www.instagram.com/yournextgenfriend/] YouTube: https://www.youtube.com/@yournextgenfriend [https://www.youtube.com/@yournextgenfriend] LinkedIn: https://www.linkedin.com/in/andreashaver/ [https://www.linkedin.com/in/andreashaver/] Subscribe to Your Next Gen Friend on your favorite podcast player: Spotify: https://yournextgenfriend.com/open-spotify [https://yournextgenfriend.com/open-spotify] Apple Podcasts: https://yournextgenfriend.com/apple-podcast [https://yournextgenfriend.com/apple-podcast] Podcast theme music by Transistor.fm.