My Worst Investment Ever Podcast

Laurie Barkman - Don't Wait Until You're Exiting to Plan Your Exit

May 18, 2026·39 min
Episode Description from the Publisher

BIO: Laurie Barkman is a Certified Exit Planner, M&A Advisor, and founder of The Business Transition Sherpa®.STORY: Laurie explains why it's important to start planning your exit plan five to seven years before and what you need to do during that period.LEARNING: Don't wait until you're exiting to plan your exit. "Don't wait to do exit planning when you're exiting, it will be too late. Start five to seven years out. This gives you time to make an impact for change, make the business more attractive and ready, and to also make yourself more ready." Laurie Barkman Guest profileLaurie Barkman is a Certified Exit Planner, M&A Advisor, and founder of The Business Transition Sherpa®. As the former CEO who led a $100 million company through acquisition, she helps business owners build valuable, sellable companies and exit on their terms.Laurie is the Amazon best-selling author of The Business Transition Handbook: How to Avoid Succession Pitfalls and Create Valuable Exit Options and hosts the award-winning podcast Succession Stories, rated in the top 2.5% of podcasts globally.Get a complimentary business assessment. See how an acquirer would evaluate your business, enabling you to focus today on what will be important down the road. Learn what changes could double the value of your business.Return visit: what's changed and what hasn'tThree years ago, Laurie joined Andrew on Ep727: Quit Often Quit Fast to share her own worst investment ever. This time, she's back with something arguably more valuable: a masterclass on the single most common mistake business owners make: waiting too long to plan their exit."I wish I knew this sooner." That phrase, Laurie says, is the number one thing she hears from business owners who've gone through a transition without proper planning. By the time they're ready to sell, it's already too late to improve the business, attract better buyers, or close the wealth gap they've been quietly ignoring.If you haven't heard Episode 727, go back and listen to Laurie's personal story. In this episode, she brings that same honesty, this time pointed squarely at what you, as a business owner, need to be doing right now.Exit planning is not an exit-day activityThe most important insight Laurie delivers in this episode is deceptively simple: exit planning needs to start long before you're planning to exit.If a prospective client tells her they're thinking about selling their business in one to three years, her response is direct: "You're already behind." A well-structured exit takes five to seven years to execute properly. That's not because the paperwork is complicated. It's because building a more attractive, more valuable, more transferable business takes time. And so does getting you personally ready for what comes after.Laurie works with two very different kinds of readiness:Business readiness: Making the business more attractive, more operationally independent, and more valuable to a future buyer.Personal readiness: Preparing the owner emotionally and financially for the life that comes after the company. Too many founders kick this can down the road, only to find the finish line overwhelming when it finally arrives.The exit timeline exerciseOne of Laurie's most practical tools is what she calls the Exit Timeline Exercise. She sits with clients and literally maps out, year by year, what needs to happen (both in the business and in their personal lives) to set them up for a successful transition.This isn't a generic checklist. It's built around the owner's specific situation: their age, their family's ages, their life stage, and what they actually want their next chapter to look like.Understanding the numbers: wealth gap

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