Business Transition Roadmap with Elizabeth Ledoux

Elizabeth Ledoux
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How do communities thrive? When businesses experience healthy growth and transition. Join CEO of The Transition Strategists, Elizabeth Ledoux as she and her guests identify what makes a successful business transition roadmap. If you know you want to transition or exit your business “one day”, today is the right day to start planning. This show will give you the roadmap.

  1. 5d ago

    She Went From Five Days a Week to Two and the Company Grew Faster

    Most owners assume the business runs through them because it always has. Ariel Steele believed that for about twenty years, and then she changed it. Ariel bought Tax Credit Connection at the end of 2005, when the company was barely a year old, after six months of running it for the previous owner. Twenty one years later she still owns all of it. What has changed is everything about how her week looks. She works two days, her five employees handle prospecting, contracts, negotiation, wires, and closings without her review, and she could be gone for a month without the company missing a step. Elizabeth frames the move against the three part structure she uses in transition strategy, which separates role, big decision making, and ownership. Ariel released most of her role and shares a good deal of the decision making with her management team while keeping full ownership. That combination is what a lot of owners want and very few name out loud. The honest part of this conversation is how long it took and what got in the way. Ariel spent years thinking the answer was the right hire or the perfect formula. It wasn't. She was holding on too tightly, and the people around her had no certainty about what their jobs actually required. Once she got clear on that, the build itself ran about three years of documented processes, training videos recorded during every training, and better tools so everyone knows when their part comes up. She also stepped down in stages, moving from five days to four to three to two, and every time she took a day back she had to decide what came off her plate and which meetings she was leaving. The second half turns to what happened with the time. Ariel wanted to be bored and never quite got there. She spent a year on health optimization and calls it a failed experiment. She traveled to India with her parents, helped them with a book, and eventually asked herself why she was so much happier than she had been a few years earlier. That question turned into Unexpected Happiness, a long format interview show where she talks with people who have come through serious personal challenges about how they managed themselves through it. She hired a producer in November, launched in March, and has about a dozen episodes out. Key takeaways from the conversation: You can release the role and keep the ownership. Ariel still owns one hundred percent of a company she rarely works in.The mindset work comes before the systems work. Ariel had to change what she believed about her own necessity before any process could stick.People need certainty about what their jobs require. Vague direction from an entrepreneurial owner reads as risk to the team.Step down in stages rather than all at once. Each day Ariel gave up forced a decision about what left her plate.Growth did not suffer. Ariel's most profitable year came after the team was in place, and she now hears compliments about her people rather than about herself.Talented people cost money. Top of range salaries, strong retention, and a pension plan are part of the arithmetic here. Elizabeth closes on the belief loop she taught at the Evolve group labs earlier this year, which is that another person's growth ties directly to how much they believe in your belief in them. Ariel's version of that is simpler. She had been afraid, she behaved like it was not safe to make a mistake around her, and letting go of the fear is what let her team grow. Connect with Ariel Steele: Linkedin: linkedin.com/in/ariel-steele-63241b415 Unexpected Happiness podcast: https://unexpectedhappiness.net/ Connect with Elizabeth Ledoux and The Transition Strategists: Website: https://transitionstrategists.com/ Get Your Copy of The Second Edition of It's A Journey: https://a.co/d/0btloXYk Subscribe to "The Business Transition Roadmap": Spotify: https://spoti.fi/3MxSYA2 Apple Podcasts: https://apple.co/3IhMMux Our Sister Show Your Next Gen Friend Hosted by Andrea Carpenter: Your Next Gen Friend is for the next generation stepping into leadership in family and private businesses. If you're a successor figuring out your path, this show is for you. Website: https://yournextgenfriend.com/ Instagram: https://www.instagram.com/yournextgenfriend/ YouTube: https://www.youtube.com/@yournextgenfriend Andrea on LinkedIn: https://www.linkedin.com/in/andreakcarpenter/ Spotify: https://yournextgenfriend.com/open-spotify Apple Podcasts: https://yournextgenfriend.com/apple-podcast

    She Went From Five Days a Week to Two and the Company Grew Faster

  2. Sep 15

    Why Your Books Decide What Happens When Private Equity Comes Knocking

    A private equity group knocks on your door tomorrow. What do your last three years of financials say about your company? In this episode, Elizabeth Ledoux talks with Brian Kofford, CPA and founder of Striv CPAs, about the work that happens long before anyone signs anything. Brian has owned his practice since 2001 and works almost entirely with growth-minded, founder-led businesses. He opens with a story about a Florida practice that grew from roughly seven million in revenue to more than forty million in five years. A private equity group came looking, saw the books, and walked away. After a couple of months of cleanup, the same company went back to market with an investment bank, received nine letters of intent, and closed a hundred million dollar transaction. Brian and Elizabeth get into why that pattern repeats. Owners are often excellent at vision, sales, and creating something from nothing, and far less interested in the details underneath. That gap shows up as books that were never converted to accrual, personal spending mixed into business expenses, and no historical record a buyer can make sense of. Brian also names the harder version of the same problem, which is the owner who is so central to every decision that there is nothing for a successor to step into. The conversation then turns to what Brian calls the million dollar ceiling. He shares a recent example of a company that grew from 2.3 million in revenue to 4.8 million in a single year, and from 400,000 in profit to 1.3 million. Their tax bill came back at 450,000, more than the entire prior year's profit, because nobody preparing the return had eyes on the growth while it was happening. On the strategy side, Brian walks through what has to be handled in advance. Estate work, trusts, charitable remainder trusts, and donor advised funds all depend on moving value at a lower valuation before a transaction, and the IRS pays attention to how much time sits between the planning and the payday. Elizabeth adds a story of two brothers who agreed verbally that one owned forty percent, never documented it, and created a taxable event on the way to a sale that could have been zero with earlier action. Key takeaways from the conversation: Buyers typically want two to three years of clean, accrual-basis financials, and five years is better if you can build the record now.Clean books matter just as much for a successor inside the family or the company. A younger successor needs numbers that make sense on their own.A lifestyle business consumes what it earns, which leaves nothing to fund the strategies that would lower the tax bill later.Tax liability climbs exponentially rather than in a straight line, and owners crossing a million in profit for the first time are often unprepared for it.Preparation is the same work no matter which path you take. Third party, employee, or family, the financials and the systems have to hold up either way. Brian and Elizabeth close on the part nobody puts in a spreadsheet. Brian compares founders to professional athletes who cannot let go of the game, and both agree that the abrupt version of this change is the hardest on the owner, the family, and the company. Long timelines give room for the tax work, the successor development, and the identity shift to happen in stages. Connect with Brian Kofford Striv CPAs: https://strivcpas.com/ Linkedin: https://www.linkedin.com/in/brian-kofford-cpa/ Connect with Elizabeth Ledoux and The Transition Strategists: Website: https://transitionstrategists.com/ Get Your Copy of The Second Edition of It's A Journey: https://a.co/d/0btloXYk Subscribe to "The Business Transition Roadmap": Spotify: https://spoti.fi/3MxSYA2 Apple Podcasts: https://apple.co/3IhMMux Our Sister Show Your Next Gen Friend Hosted by Andrea Carpenter: Your Next Gen Friend is for the next generation stepping into leadership in family and private businesses. If you're a successor figuring out your path, this show is for you. Website: https://yournextgenfriend.com/ Instagram: https://www.instagram.com/yournextgenfriend/ YouTube: https://www.youtube.com/@yournextgenfriend Andrea on LinkedIn: https://www.linkedin.com/in/andreakcarpenter/ Spotify: https://yournextgenfriend.com/open-spotify Apple Podcasts: https://yournextgenfriend.com/apple-podcast

    Why Your Books Decide What Happens When Private Equity Comes Knocking

  3. Sep 1

    Lessons from a Successor Turned Transitioner with Laura Chiesman

    What happens when the person who wrote the roadmap has to follow it twice? In this episode, Elizabeth Ledoux sits down with Laura Chiesman, managing partner and financial advisor with Savant Wealth Management and Elizabeth's co-author on It's a Journey. Laura has experienced transition from both seats. As a successor, she purchased her firm from its original founder in 2015. As a transitioner, she later merged that firm with Savant Wealth Management, guided by the same process the two of them outline in the book. Laura shares what made her first transition work: the pre-work the founder did before ever extending the invitation, the people-first approach that kept a longtime friendship intact, and the communication plan that reached team members, key clients, and pivotal vendors before anyone heard the news secondhand. She's honest about the hard parts too, including the legal contingency work that forced her to plan for outcomes she hoped would never happen. Then Laura switches to her advisor lens. With over 30 years in wealth management, she has seen owners fixate on a dollar amount with no rhyme or reason behind it, and she has taken calls from sellers a week before closing who have no idea what they'll owe in taxes. Her answer is a financial planning process that projects the life you envision and takes you to a real number, so you can winnow out deals that don't fit and negotiate with confidence for the ones that do. Key takeaways from the conversation: A transition roadmap gives a successor confidence from the first conversation. Laura knew there was a path to follow, even for the biggest financial decision of her life.Freedom was Laura's driver as a transitioner. Not freedom to stop working, but the option to choose on her own timeline while protecting the people who depend on her.Knowing your number changes the negotiation. If a deal covers what you actually need, fighting for the last dollar can cost you a good outcome and a good relationship.The net matters more than the headline price. Taxes, healthcare costs, and lifestyle expenses the business used to carry all come out of the planning process.Start early. Three years minimum for a third-party sale, five or more if you plan to mentor a successor, and be ready for the timeline to stretch. Whether you're a future successor, an owner beginning to think about your next adventure, or an advisor guiding clients through it, Laura's story is proof that the process works on both sides of the table. This conversation also touches on the newly released Second Edition of It's a Journey, including a brand-new chapter on Transition 3.0 and how to bring people into the process. Details in the links below. Connect with Laura Chiesman Savant Wealth Management: https://savantwealth.com/ Linkedin: https://www.linkedin.com/in/laurachiesman/ Get Your Copy of The Second Edition of It's A Journey: https://a.co/d/0btloXYk Connect with Elizabeth Ledoux and The Transition Strategists: Website: https://transitionstrategists.com/ Subscribe to "The Business Transition Roadmap": Spotify: https://spoti.fi/3MxSYA2 Apple Podcasts: https://apple.co/3IhMMux Our Sister Show Your Next Gen Friend Hosted by Andrea Carpenter: Your Next Gen Friend is for the next generation stepping into leadership in family and private businesses. If you're a successor figuring out your path, this show is for you. Website: https://yournextgenfriend.com/ Instagram: https://www.instagram.com/yournextgenfriend/ YouTube: https://www.youtube.com/@yournextgenfriend Andrea on LinkedIn: https://www.linkedin.com/in/andreakcarpenter/ Spotify: https://yournextgenfriend.com/open-spotify Apple Podcasts: https://yournextgenfriend.com/apple-podcast

    Lessons from a Successor Turned Transitioner with Laura Chiesman

  4. Aug 18

    Five Things That Compound When You Plan and Stay

    What if a transition strategy started paying you back years before you ever stepped back? In this episode, Elizabeth Ledoux continues her conversation with the still-building visionaries, the owners who are still growing their companies and still the reason so much of the business works. Last episode broke the countdown myth, the belief that planning equals leaving. This one is about what happens once you stop believing it. Elizabeth calls it the multiplier effect, and she walks through five specific things that compound the moment you start planning while you're still fully in the seat. She also opens up about her own transition, including what she told her incoming successor about the moment a transition truly succeeds, and tells the story of an early client whose strategic work positioned him to absorb 700% growth in a single year when his biggest competitor sold to private equity. Key Takeaways: Your people grow when the strategy is bigger than you. Talking about a multi-generational business removes the "end feeling" for loyal employees and invites them to build judgment and make decisions without you. You're already doing transition work. Every time you teach someone to do what you used to do, that's transition. A bigger strategy just gets you a bigger multiplier out of it. A business that depends on one person is fragile. Moving decision making, vision, and energy off of yourself makes the company more valuable to a buyer, a lender, your family, and your employees. Readiness beats prediction. You never know what's coming around the corner. The strategic work is what lets you pivot when the market shifts. Freedom is a mindset shift, not just free time. The strategy work opens up the question of what you might move toward, whether that's writing, speaking, or something new entirely. Hard conversations get easier without a crisis. Dig your well before you're thirsty. Designing from a calm place gives everyone more context and less to defend. Sharp decisions come from a visible roadmap. When you can see five or ten years out, the choices you make today actually get you there, instead of needing to be redone later. Don't wait for the surprise. Health scares, burnout, and unsolicited private equity offers are arriving more often. Planning early means responding on your terms and your timeline. Connect with Elizabeth Ledoux and The Transition Strategists: Website: https://transitionstrategists.com/ Subscribe to "The Business Transition Roadmap": Spotify: https://spoti.fi/3MxSYA2 Apple Podcasts: https://apple.co/3IhMMux Our Sister Show Your Next Gen Friend Hosted by Andrea Carpenter: Your Next Gen Friend is for the next generation stepping into leadership in family and private businesses. If you're a successor figuring out your path, this show is for you. Website: https://yournextgenfriend.com/ Instagram: https://www.instagram.com/yournextgenfriend/ YouTube: https://www.youtube.com/@yournextgenfriend Andrea on LinkedIn: https://www.linkedin.com/in/andreakcarpenter/ Spotify: https://yournextgenfriend.com/open-spotify Apple Podcasts: https://yournextgenfriend.com/apple-podcast

    Five Things That Compound When You Plan and Stay

  5. Aug 4

    Why a Transition Strategy Is a Multiplier, Not a Countdown

    What if the reason you keep pushing "start transition planning" down your to-do list has nothing to do with being busy? In this episode, Elizabeth Ledoux speaks to the owners who are still building. Not winding down, not stepping back, still fully in it. For these owners, the phrase transition planning often lands like an ending: a date, a handoff, a last day. Elizabeth calls this the countdown myth, and it keeps successful owners stuck in a quiet trap where the business runs through them and planning starts to feel like the only thing left is goodbye. Then she flips it. A transition strategy is not a countdown. It's a multiplier. It multiplies your clarity, your options, your people's trust, and your own bandwidth. Elizabeth shares her own story of building her strategy five years ago, long before she knew who her successor would be, and how that work led to a new business partner and a company that's now multiplying. Key takeaways from the episode: The clock is already running. Avoiding a strategy doesn't keep the clock off; the business is aging, your people are waiting, and the market keeps shifting.The more successful you are, the more the business runs through you, even if you've stepped back from the day to day. That dependence is the quiet trap.You can fully plan and stay another decade or two. A strategy is a direction, not a departure date.A strategy is only intention on paper. The real value is in the planning process itself, the deep reflection on what you want and how you want your people treated.Starting early puts the odds in your favor. No plan means choosing from whatever's left when the day comes.Blend your transition strategy into your business strategy. The business moves, and you start moving with it.Roughly two thirds of businesses fail in transition. The ones that succeed treat time as an asset, not a threat. Connect with Elizabeth Ledoux and The Transition Strategists: Website: https://transitionstrategists.com/ Subscribe to "The Business Transition Roadmap": Spotify: https://spoti.fi/3MxSYA2 Apple Podcasts: https://apple.co/3IhMMux Our Sister Show Your Next Gen Friend Hosted by Andrea Carpenter: Your Next Gen Friend is for the next generation stepping into leadership in family and private businesses. If you're a successor figuring out your path, this show is for you. Website: https://yournextgenfriend.com/ Instagram: https://www.instagram.com/yournextgenfriend/ YouTube: https://www.youtube.com/@yournextgenfriend Andrea on LinkedIn: https://www.linkedin.com/in/andreakcarpenter/ Spotify: https://yournextgenfriend.com/open-spotify Apple Podcasts: https://yournextgenfriend.com/apple-podcast

    Why a Transition Strategy Is a Multiplier, Not a Countdown

  6. Jul 21

    What It Actually Takes to Hand a Family Business to the Next Generation

    What does it actually take to prepare the next generation for ownership? In this special replay episode, Elizabeth Ledoux and Andrea Carpenter join Family Business Magazine for a live webinar on designing a win-win-win handoff, a transition where the transitioner, the successor, and the business itself all get what matters most to them. Elizabeth and Andrea introduce two of TTS's core tools, the Transition Compass (the why, what, who, when, how, and how much) and the Objectives Matrix, and explain why assumptions, not conflict, are usually what derail a family transition. Then Laurie and Brad Irish-Jones of Irish Family Companies, a fourth-generation family business founded in 1932, join to share their own story. Laurie, the former CEO, describes what it felt like to be one of five sisters running the business together in their fifties with no clear timeline for who was leaving when. Brad, from the next generation, describes the frustration of "deal fatigue" and what it took for sixteen grandchildren across the family to find their footing. Together they discuss what held the family together through the harder conversations, what it actually felt like to let go, and what they would tell any family standing where they once stood. Zach Needles of Family Business Magazine moderates an extended audience Q&A covering board governance, sibling disagreement over who wants in, and how often a transition plan should be revisited once it's built. Connect with Elizabeth Ledoux and The Transition Strategists: Website: https://transitionstrategists.com/ Subscribe to "The Business Transition Roadmap": Spotify: https://spoti.fi/3MxSYA2 Apple Podcasts: https://apple.co/3IhMMux Our Sister Show Your Next Gen Friend Hosted by Andrea Carpenter: Your Next Gen Friend is for the next generation stepping into leadership in family and private businesses. If you're a successor figuring out your path, this show is for you. Website: https://yournextgenfriend.com/ Instagram: https://www.instagram.com/yournextgenfriend/ YouTube: https://www.youtube.com/@yournextgenfriend Andrea on LinkedIn: https://www.linkedin.com/in/andreakcarpenter/ Spotify: https://yournextgenfriend.com/open-spotify Apple Podcasts: https://yournextgenfriend.com/apple-podcast

    What It Actually Takes to Hand a Family Business to the Next Generation

  7. Jul 7

    Drones, Renters, or Owners: Leading People Through Transition

    What if the hardest part of leading through change is not building the plan, but accepting that the plan will never survive contact with reality? In this episode, Elizabeth Ledoux talks with Mike Wettlaufer, a retired Navy rear admiral and lifelong entrepreneur, about leading people through change. Across 38 years and thousands of people, Mike learned that a straight line from A to B is a fantasy. You hope you land somewhere near where you aimed, but the value was never the plan itself. It lives in the planning: the relationships you build, the options you explore, and the readiness to pivot when something you never saw coming arrives. Mike and Elizabeth get into the human side of transition, from why communication is the hardest work a leader does to how you win the middle of a room instead of exhausting yourself on the people who will never come along. Mike maps his own framework of drones, renters, and owners directly onto Elizabeth's Transition 1.0, 2.0, and 3.0, and he makes the case that ownership is something you build in a successor over time, not something you hand them on day one. If you are a business owner thinking about bringing successors into the process, this conversation is a practical look at how to start early and how to do it well. Key takeaways from this episode: The plan is never the point. The planning is. A straight line from A to B does not happen, and the real value lives in the process, the relationships, and staying ready to pivot when something you never planned for shows up.Communication is the hardest work a leader does. People take in information differently, and when someone "doesn't understand," it usually means you have not yet found the way to reach them.You do not need the whole room. Roughly twenty percent will follow you because you are the boss, twenty percent never will, and the real work is the middle sixty percent. You only need momentum from about a third of them to start moving.Sudden change creates drones. When a decision lands with no warning, people resist it like a threat. Warm the room early so they build antibodies instead of fighting the decision.Ownership is built, not handed over. You create owners by giving successors real, low-stakes work early and letting them own the result, not by putting them in the C-suite on day one. Coach instead of correct, and let the honest assessment come from them.Without a debrief, there is no learning. Plan, prepare, and execute, then sit down and debrief. That is where the plan gets adjusted and where people actually grow.Start early enough that leaving is not too soon. Owners often step back before their successors are ready. Beginning the process years earlier lets you find the gaps at the five-year mark and still have time to pivot. Connect with Mike Wettlaufer on Linkedin: https://www.linkedin.com/in/wettlauferm/ Connect with Elizabeth Ledoux and The Transition Strategists: Website: https://transitionstrategists.com/ Subscribe to "The Business Transition Roadmap": Spotify: https://spoti.fi/3MxSYA2 Apple Podcasts: https://apple.co/3IhMMux Our Sister Show Your Next Gen Friend Hosted by Andrea Carpenter: Your Next Gen Friend is for the next generation stepping into leadership in family and private businesses. If you're a successor figuring out your path, this show is for you. Website: https://yournextgenfriend.com/ Instagram: https://www.instagram.com/yournextgenfriend/ YouTube: https://www.youtube.com/@yournextgenfriend Andrea on LinkedIn: https://www.linkedin.com/in/andreakcarpenter/ Spotify: https://yournextgenfriend.com/open-spotify Apple Podcasts: https://yournextgenfriend.com/apple-podcast

    Drones, Renters, or Owners: Leading People Through Transition

  8. Jun 23

    The Signals Are Already There

    What if the hardest part of transition is not the planning, but admitting to yourself that something has already started to shift? In this solo episode, Elizabeth Ledoux talks about the signals most owners notice long before they say them out loud. They rarely arrive as a clear decision. They show up as a low-grade restlessness, a shorter runway, less appetite for the next big risk, or a quiet gut feeling that you are not reaching as hard as you used to. Elizabeth walks through what those signals look like, what tends to happen when owners keep explaining them away, and what opens up when they finally stop. She shares two stories from her work. One is about an owner who kept saying not yet until a cancer diagnosis gave him six months and a sudden willingness to do the work, surfacing years of family conversations that could have happened sooner. The other is about a road-worn owner who arrived certain he wanted a fast third-party sale, until his own lawyer told him to slow down and figure out what he truly wanted. What he discovered changed the entire shape of his transition and gave him years of fulfillment on his own terms. Key takeaways from this episode: Transition signals do not announce themselves. They show up quietly, in ways that are easy to rationalize because they feel small."I'll deal with it when things calm down" is a loop. Things rarely calm down, and the urge to wait can itself be a signal that your runway is getting shorter.A lower appetite for risk is not a flaw. As the runway shortens, many owners take smaller risks because they have less time to recover, and noticing that shift is the point.The people around you carry signals too. A spouse who keeps mentioning travel, a child asking to buy in, a key employee quietly stepping up, these are information, not just interruptions.Your gut instinct got you here. If it is telling you that you are not as interested in the next decade of growth, that is worth honoring.This discomfort is usually not burnout. More often it means you are outgrowing your current chapter, and that can be a beautiful place to shift from when you are ready. Connect with Elizabeth Ledoux and The Transition Strategists: Website: https://transitionstrategists.com/ Subscribe to "The Business Transition Roadmap": Spotify: https://spoti.fi/3MxSYA2 Apple Podcasts: https://apple.co/3IhMMux Our Sister Show Your Next Gen Friend Hosted by Andrea Carpenter: Your Next Gen Friend is for the next generation stepping into leadership in family and private businesses. If you're a successor figuring out your path, this show is for you. Website: https://yournextgenfriend.com/ Instagram: https://www.instagram.com/yournextgenfriend/ YouTube: https://www.youtube.com/@yournextgenfriend Andrea on LinkedIn: https://www.linkedin.com/in/andreakcarpenter/ Spotify: https://yournextgenfriend.com/open-spotify Apple Podcasts: https://yournextgenfriend.com/apple-podcast

    The Signals Are Already There
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How do communities thrive? When businesses experience healthy growth and transition. Join CEO of The Transition Strategists, Elizabeth Ledoux as she and her guests identify what makes a successful business transition roadmap. If you know you want to transition or exit your business “one day”, today is the right day to start planning. This show will give you the roadmap.

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