Considering that 12 million businesses are still owned by Baby Boomers, exit strategy for this generation may not only be how to enter the Retirement phase of our lives, but how do we exit the business that we may have built up over the decades. In this section of the site, our Experts explore both our business lives and our personal lives in exiting our current Lifestyle and building for the future.
Retirement can be a complex process, especially for Baby Boomers who have accumulated wealth, businesses, or Family responsibilities over the years. An exit strategy isn’t just about leaving work behind—it’s about ensuring that all aspects of life are organized, from finances to legal matters, so that the next phase is as comfortable and secure as possible. An exit strategy goes beyond a traditional retirement plan. While a retirement plan focuses on saving and managing Money for life after work, an exit strategy encompasses succession planning, Estate planning, and healthcare considerations—ensuring that all aspects of life are addressed.
The retirement landscape has shifted drastically. It’s no longer just about kicking back after decades of hard work. Baby boomers face unique challenges, like longer life expectancies, evolving healthcare costs, and market volatility. An exit strategy isn’t just a nice-to-have—it’s a must! Crafting a successful exit strategy is about more than just planning for retirement. It’s about securing your financial future, ensuring your Legacy, and preparing for the next chapter of life with confidence.
Exit Specialists & Contributors
Rich Hall Certified Exit Planning Advisor | Business Advisor | Baby Boomer
Own a logistics business doing $2M+ in revenue? Apply for a Business Valuation Call to learn what your company is worth and how to increase its exit value: https://www.bizexitgrow.com/valuation-callA business cannot scale sustainably when its people, purpose, systems, and performance are out of alig…
Own a logistics business doing $2M+ in revenue? Apply for a Business Valuation Call to learn what your company is worth and how to increase its exit value: https://www.bizexitgrow.com/valuation-callA …
Own a logistics business doing $2M+ in revenue? Apply for a Business Valuation Call to learn what your company is worth and how to increase its exit value: https://www.bizexitgrow.com/valuation-callA business cannot scale sustainably when its people, purpose, systems, and performance are out of alignment.In this episode, Hanna Bauer explains how owners can reduce overwhelm, empower their employees, eliminate key-person risk, and build organizations that continue performing when the founder steps away.Hanna is an award-winning entrepreneur and leadership strategist with nearly 30 years of exper…
Anika sits down with Julie Ellis to explore the inflection point every founder dreads—the moment you've built the business, achieved the goal, and suddenly realize you have no idea who you are without it. Discover why selling an eight-figure business can feel like grief disguised as success, how d…
Anika sits down with Julie Ellis to explore the inflection point every founder dreads—the moment you've built the business, achieved the goal, and suddenly realize you have no idea who you are witho…
Anika sits down with Julie Ellis to explore the inflection point every founder dreads—the moment you've built the business, achieved the goal, and suddenly realize you have no idea who you are without it. Discover why selling an eight-figure business can feel like grief disguised as success, how delegation is the real bottleneck between scaling and plateauing, and the counterintuitive truth that derails most women entrepreneurs: it's never about having a bigger vision. It's about believing you're worthy of one—and whether you have the systems and people around you to make it real.In This E…
Money is emotional. Every financial decision we make is shaped by experiences, beliefs, fears, and behaviors that have nothing to do with spreadsheets or market performance.
In this episode of Behind The Numbers With Dave Bookbinder, Kate Duffy, Senior Vice President and Wealth Advisor at Bryn Mawr …
Money is emotional. Every financial decision we make is shaped by experiences, beliefs, fears, and behaviors that have nothing to do with spreadsheets or market performance.
In this episode of Behind …
Money is emotional. Every financial decision we make is shaped by experiences, beliefs, fears, and behaviors that have nothing to do with spreadsheets or market performance.
In this episode of Behind The Numbers With Dave Bookbinder, Kate Duffy, Senior Vice President and Wealth Advisor at Bryn Mawr Trust, pulls back the curtain on the psychology of wealth. As a Certified Financial Behavior Specialist and co-host of The Planning Perspectives Podcast, Kate explains why clients stall on logically perfect financial plans and explores the profound identity crisis entrepreneurs face when selling a b…
Own a logistics business doing $2M+ in revenue? Apply for a Business Valuation Call to learn what your company is worth and how to increase its exit value: https://www.bizexitgrow.com/valuation-call If your team constantly needs you to make decisions, solve problems, and keep work moving, you do no…
Own a logistics business doing $2M+ in revenue? Apply for a Business Valuation Call to learn what your company is worth and how to increase its exit value: https://www.bizexitgrow.com/valuation-call …
Own a logistics business doing $2M+ in revenue? Apply for a Business Valuation Call to learn what your company is worth and how to increase its exit value: https://www.bizexitgrow.com/valuation-call If your team constantly needs you to make decisions, solve problems, and keep work moving, you do not have a scalable business.In this episode, Lindsay White explains how founders can eliminate owner dependence by designing the right roles, developing capable leaders, and transferring critical knowledge into the business.Lindsay has more than 20 years of experience in human resources and is the fo…
Colin C. Campbell, is a Serial Entrepreneur and #1 best selling author in 15 categories and 13 awards on Amazon of Start. Scale. Exit. Repeat. Colin started, scaled, and exited over a dozen companies worth almost 1 billion dollars including Tucows, Hostopia, .CLUB Domains, GeeksforLess and Paw.com. …
Colin C. Campbell, is a Serial Entrepreneur and #1 best selling author in 15 categories and 13 awards on Amazon of Start. Scale. Exit. Repeat. Colin started, scaled, and exited over a dozen companies …
Colin C. Campbell, is a Serial Entrepreneur and #1 best selling author in 15 categories and 13 awards on Amazon of Start. Scale. Exit. Repeat. Colin started, scaled, and exited over a dozen companies worth almost 1 billion dollars including Tucows, Hostopia, .CLUB Domains, GeeksforLess and Paw.com. Colin also runs Startup Club with 1M members. Top 3 Value Bombs 1. Great entrepreneurs build wealth by knowing when to start, when to scale, and when to exit. Holding on forever can be far riskier than taking chips off the table at the right time. 2. The best business ideas solve real problems, scal…
Beth sits down with Lauren Pinkston, an independent candidate for governor of Tennessee, on the same day Governor Beshear sent Senator Mitch McConnell a letter asking about his month-long hospitalization. They use that story, plus Graham Platner's exit from the Maine Senate race, to get at something…
Beth sits down with Lauren Pinkston, an independent candidate for governor of Tennessee, on the same day Governor Beshear sent Senator Mitch McConnell a letter asking about his month-long hospitalizat…
Beth sits down with Lauren Pinkston, an independent candidate for governor of Tennessee, on the same day Governor Beshear sent Senator Mitch McConnell a letter asking about his month-long hospitalization. They use that story, plus Graham Platner's exit from the Maine Senate race, to get at something bigger: what "honor" means in public life when authenticity and elitism both fall short. Then they turn to what that looks like in practice — data centers, classrooms, and a possible return of family dinners to the governor's residence.
Topics discussed:
Transparency and elected officials' hea…
Most investors think market crashes are what destroy wealth.
They're wrong.
The fastest way to lose money in real estate is much simpler:
• Underestimating your expenses.
• Overestimating your rental income.
• Buying without a clear exit strategy.
In today's market, disciplined underwriting…
Most investors think market crashes are what destroy wealth.
They're wrong.
The fastest way to lose money in real estate is much simpler:
• Underestimating your expenses.
• Overestimating your r…
Most investors think market crashes are what destroy wealth.
They're wrong.
The fastest way to lose money in real estate is much simpler:
• Underestimating your expenses.
• Overestimating your rental income.
• Buying without a clear exit strategy.
In today's market, disciplined underwriting matters more than ever. Rising insurance costs, increasing property taxes, higher interest rates, and slowing rent growth have changed the rules of investing. If you're still using yesterday's assumptions, you could be setting yourself up for costly mistakes.
In this episode, Gino Barbaro explains …
Do you own a transportation or 3PL business doing $3M or more in revenue? Visit www.bizexitgrow.com to find out how we can help you grow, scale, and exit at maximum value.Ben Buckley got fired, had four kids to feed, and turned $50 TV installs into an eight-figure business serving Apple, Salesforce,…
Do you own a transportation or 3PL business doing $3M or more in revenue? Visit www.bizexitgrow.com to find out how we can help you grow, scale, and exit at maximum value.Ben Buckley got fired, had fo…
Do you own a transportation or 3PL business doing $3M or more in revenue? Visit www.bizexitgrow.com to find out how we can help you grow, scale, and exit at maximum value.Ben Buckley got fired, had four kids to feed, and turned $50 TV installs into an eight-figure business serving Apple, Salesforce, and Samsung. In this episode, we break down how he bootstrapped Digital Dreams, why the smallest details win and lose enterprise clients, and how he scaled a service business across dozens of states, with Ben Buckley.Ben is the owner of Digital Dreams, a Northern California commercial audio-visual …
Do you own a transportation or 3PL business doing $3M or more in revenue? Visit www.bizexitgrow.com to find out how we can help you grow, scale, and exit at maximum value.The same business with a $1M EBITDA can sell for $3M or $8M, and the difference comes down to systems, structure, and timing. In …
Do you own a transportation or 3PL business doing $3M or more in revenue? Visit www.bizexitgrow.com to find out how we can help you grow, scale, and exit at maximum value.The same business with a $1M …
Do you own a transportation or 3PL business doing $3M or more in revenue? Visit www.bizexitgrow.com to find out how we can help you grow, scale, and exit at maximum value.The same business with a $1M EBITDA can sell for $3M or $8M, and the difference comes down to systems, structure, and timing. In this episode, we break down how to prepare your company for a high-value exit, why entity structure matters, and how to legally protect your assets and reduce your tax burden, with Bobby Casey.Bobby is a lifelong entrepreneur, international tax strategist, managing partner of Global Wealth Protectio…
Sarah Jeanneault started as a schoolteacher. She did not plan a career in fintech. An unexpected life change pushed her toward a side project. The side project found an audience. The audience became a business. In this episode, Sarah walks through what that transition actually required: listening cl…
Sarah Jeanneault started as a schoolteacher. She did not plan a career in fintech. An unexpected life change pushed her toward a side project. The side project found an audience. The audience became a…
Sarah Jeanneault started as a schoolteacher. She did not plan a career in fintech. An unexpected life change pushed her toward a side project. The side project found an audience. The audience became a business. In this episode, Sarah walks through what that transition actually required: listening closely to early followers before the product was fully formed, building community through blogging and early Twitter before either of those was a recognized growth strategy, and staying honest about what was working and what was not in a way most founders avoid. She covers the moment she realized her…
Pete Vera
July 15, 2026
Anika Jackson 
Dave Bookbinder 
John Lee Dumas 
Sarah & Beth 
Gino Barbaro 
Dave Gulas