EP 04: The Exit You Can’t Avoid: Preparing Your Business—and Life—for What’s Next episode artwork

EPISODE · Jul 28, 2025 · 38 MIN

EP 04: The Exit You Can’t Avoid: Preparing Your Business—and Life—for What’s Next

from SEASON 2: Beyond the Exit Show · host Steve Adams

What do 100% of business owners have in common? They will exit—either by choice or by circumstance.In this episode, Steve Adams sits down with certified exit planning advisor Kelli Olsheski to reveal the hidden risks most business owners face when exiting their companies—and how to turn your business into a sellable, valuable asset long before you're ready to leave.Whether you're five months or five years away from an exit, Kelli’s insights will shift your mindset from reactive to strategic. You’ll learn how to build business value, prepare for lifestyle funding, and design a post-exit life that’s meaningful—not aimless.💡 What You’ll Learn:✔️ Why 80% of business owners feel lost one year after selling ✔️ The “Five Ds” that force 70% of exits—and how to avoid them ✔️ Why maximizing EBITDA isn’t enough—you need transferable value ✔️ Four capital areas every buyer evaluates (and how to boost each one) ✔️ How to plan your life after the exit, not just your finances ✔️ The overlooked cost of running personal expenses through your business ✔️ Why purpose, structure, and legacy must drive your next chapter00:00 Starting Strong03:33 Business Owner Insights08:22 Key Wealth Steps15:57 Building Business Value23:51 The Five Ds30:41 Personal Planning35:57 Family and Legacy37:49 Final TakeawaysLearn more about the Tiger Health Assessment here -  http://www.tigerhealthassessment.com Learn more here: https://www.tigermi.com/

What do 100% of business owners have in common? They will exit—either by choice or by circumstance.In this episode, Steve Adams sits down with certified exit planning advisor Kelli Olsheski to reveal the hidden risks most business owners face when exiting their companies—and how to turn your business into a sellable, valuable asset long before you're ready to leave.Whether you're five months or five years away from an exit, Kelli’s insights will shift your mindset from reactive to strategic. You’ll learn how to build business value, prepare for lifestyle funding, and design a post-exit life that’s meaningful—not aimless.💡 What You’ll Learn:✔️ Why 80% of business owners feel lost one year after selling ✔️ The “Five Ds” that force 70% of exits—and how to avoid them ✔️ Why maximizing EBITDA isn’t enough—you need transferable value ✔️ Four capital areas every buyer evaluates (and how to boost each one) ✔️ How to plan your life after the exit, not just your finances ✔️ The overlooked cost of running personal expenses through your business ✔️ Why purpose, structure, and legacy must drive your next chapter00:00 Starting Strong03:33 Business Owner Insights08:22 Key Wealth Steps15:57 Building Business Value23:51 The Five Ds30:41 Personal Planning35:57 Family and Legacy37:49 Final TakeawaysLearn more about the Tiger Health Assessment here -  http://www.tigerhealthassessment.com Learn more here: https://www.tigermi.com/

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EP 04: The Exit You Can’t Avoid: Preparing Your Business—and Life—for What’s Next

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How long is this episode of SEASON 2: Beyond the Exit Show?

This episode is 38 minutes long.

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This episode was published on July 28, 2025.

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What do 100% of business owners have in common? They will exit—either by choice or by circumstance.In this episode, Steve Adams sits down with certified exit planning advisor Kelli Olsheski to reveal the hidden risks most business owners face when...

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