You’re going to fail after your exit. The only question is: how badly?
The Crisis Nobody Talks About After You Sell
You work your whole life to build a successful business. You survive the stress, scale up, and finally exit. But what comes next?
Most entrepreneurs fall flat—financially secure, but emotionally bankrupt. Lost. Unfulfilled. Searching for purpose.
Scott Couchenour knows this pain. After nearly 30 years in his family’s business, he was forced to shut it down. At age 50, he found himself broke, jobless, and questioning everything.
Today, Scott is a sought-after legacy transition expert who helps successful entrepreneurs over 45 create a powerful second act.
In this no-fluff conversation, he reveals why you’re almost guaranteed to fail after your exit—and the proven strategies to turn that failure into a reinvention.
The Phone Call That Changed Everything
It started like any other day. Scott’s team was counting on a major church construction project to start. It didn’t.
“The pastor had been caught in a scandal. Just like that, the project was pulled,” Scott said. “That single moment collapsed everything.”
Despite $20M in projects in the pipeline, cash flow dried up. Within months, a 44-year-old business with 760 completed projects ceased to exist.
It wasn’t just a business loss—it was an identity crisis.
Who Are You Without the Title?
Scott calls this the “Moonlight Principle.” The moon looks like it’s shining—but it’s just reflecting the sun. Your role as CEO or founder? That’s moonlight.
“The business is not who you are. It’s how others experience who you are,” he says. “When the business is gone, you’re still here.”
But most entrepreneurs never realize this until it’s too late. They cling to the identity of business owner like a life raft—and sink when it’s gone.
That’s why post-exit failure is so common.
The Hidden Danger of Entrepreneurial Success
Scott references Jim Collins’ How the Mighty Fall. The first stage of decline? A hubris born of success.
“We kept saying, ‘We’ve been doing this for 40 years. The market will come back.’ But it didn’t,” Scott recalls.
This overconfidence blinds entrepreneurs. What worked yesterday won’t necessarily work tomorrow. And if you wait too long to reinvent yourself, the cost is massive.
The Six-Pillar Framework to Reclaim Your Life
Scott’s transformation—and now his coaching system—is built around six life pillars:
- Spiritually Anchored – Find purpose beyond profit
- Physically Fit – Stay sharp and energized for the long haul
- Relationally Rich – Build meaningful personal connections
- Emotionally Healthy – Manage stress, uncertainty, and loss
- Vocationally Aligned – Create work that fits your identity today
- Financially Free – Reframe wealth as a tool for impact
This isn’t theory—it’s a battle-tested blueprint for living by design, not by default.
Why You Need 90-Day Sprints
Instead of vague life goals, Scott coaches clients through structured 90-day sprints—actionable blocks that build momentum and clarity fast.
His system uses a “FILMS Review” (Forward, Intuition, Learn, Measure, So What) to reflect and reset every quarter.
“Entrepreneurs thrive on progress,” he says. “Without direction, they drift. These sprints create alignment and acceleration.”
The outcome? Founders go from lost to laser-focused.
Agency: The Most Underrated Post-Exit Asset
At the core of Scott’s message is agency—the belief that you have control and options.
“When you’re living by default, you feel like life is happening to you. But when you regain agency, you design your life proactively.”
This shift doesn’t happen overnight—but it starts with a decision: to stop surviving and start designing.
Faith, Failure, and Finding What Matters
Scott’s journey is deeply rooted in faith. His spiritual framework sustained him through deep personal and professional loss.
But you don’t need to share his beliefs to benefit. His real message is universal:
“In uncertainty, faith grows. And when everything falls apart, you find what truly matters.”
Your Exit Is the Beginning, Not the End
If you’ve sold your business or are preparing to exit, this episode is your wake-up call.
Don’t wait for the crash. Don’t wait to lose everything before you start building what’s next.
Legacy Expert Scott Couchenour has lived the failure—and engineered the fix.
This episode delivers the mindset, strategy, and truth every entrepreneur needs before and after the exit.
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Today, Feldberg's passion is helping you extract your deep wealth. The 90-day Deep Wealth Mastery program helps create a solid foundation for three areas: increasing profits to enterprise value and optimizing post-exit life. Deep Wealth Mastery offers strategies and insights drawn from Feldberg's rich experience. The strategies from the trenches get results. Jeffrey's vision is to increase the social fabric of society one entrepreneur at a time.
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- You’re Going to Fail After Your Exit: Legacy Expert Scott Couchenour Shares the Strategies You Don’t Know (Yet)
- Post-Exit Entrepreneurs AJ Wasserstein & Jeff Swearingen Reveal 6 Critical Decisions You MUST Make After Selling Your Business (Or Else You’ll Regret It)
- The Hero Hiring Playbook: 9-Figure Post-Exit Entrepreneur Reveals How To Skyrocket Profits And Nail Your Exit
