You wake up Monday post-exit, millions in the bank—no purpose, no rhythm, just a haunting “What now?” That’s not freedom—it’s a trap most entrepreneurs fall into. In Episode 439 of The Deep Wealth Podcast, post-exit entrepreneurs AJ Wasserstein and Jeff Swearingen expose the raw truth about life after the deal.
Their data-driven playbook, backed by a survey of post-exit founders, reveals six critical decisions you MUST make to avoid regret and thrive. Ready to dodge the pitfalls that derail 80% of entrepreneurs? Let’s dive in.
Freedom’s Hidden Cost
You’ve sprinted to the finish line—years of grind, late nights, payrolls made by a whisker. You sell. You win. Then what? Wasserstein and Swearingen warn: freedom comes with a brutal cost. “The entrepreneur swaps their company for freedom,” they write, “but with that comes confusion, a sense of loss, and a lack of purpose, identity, and goals.” Their data shocks: only 20% of post-exit entrepreneurs plan for life after the sale, and just 22% find it matches their dreams.
Wasserstein, a Yale lecturer who scaled and sold two national companies, lays it bare: “The vast majority aren’t thinking about this at all.” Swearingen, who bootstrapped SecureLink to a nine-figure exit, admits: “I missed the meetings, the grind, the pressure. They gave my life rhythm. When that disappeared, I didn’t know who I was.” The result? A staggering 60% of entrepreneurs, even six years post-exit, still haven’t found purpose or identity.
Question 1: How Will I Manage My Wealth?
Wealth isn’t about chasing returns—it’s about dodging chaos. Despite an average net worth of $32 million, their dataset’s entrepreneurs crave $65 million yet ditch private equity and hedge funds, held by 84% but desired by only 33%. “The premium isn’t worth the complexity,” Wasserstein says. Index funds? Six times more coveted.
Swearingen is blunt: “Show me a managed portfolio that beats low-cost index funds long-term. It doesn’t exist.” He learned the hard way, buried in “head trash” from complex investments. Their fix? A set-it-and-forget-it index fund strategy—simple, elegant, and freeing.
Question 2: What’s My Spending Strategy?
More money, more problems? Absolutely. Their data shows 80% of post-exit entrepreneurs spend under 3% of their wealth yearly, despite 7-8% returns. “We’re not spending what we could, yet we want more,” Swearingen marvels. The risk? Underspending—missing joy for fear of loss.
Their case note slams “toys” like boats or multiple homes: “They drain time, energy, and cash with taxes and upkeep.” Swearingen confesses: “Four houses? Too much work.” Spend 1-4% of your assets intentionally to live richly without sleepless nights.
Question 3: What’s My Approach to Philanthropy?
Philanthropy sounds noble, but the data disappoints: 84% plan to give less than 50% of their wealth, with 28% at 5-10%. “I hoped for more generosity, sooner,” Wasserstein says. Swearingen adds: “We’re stewards, not owners, yet we hoard.” Why the delay? “Nonprofits want your money, not your time or talent,” Swearingen notes. “It’s slower than business.”
Their advice? Start now. Wasserstein’s family gives annually post-Thanksgiving, a deliberate ritual. “Find causes that light you up,” he urges, “and don’t wait for ‘someday.’” Purpose awaits—listen to this episode now to unlock their playbook.
Question 4: How Will I Structure My Daily Routine?
Post-exit life lacks your business’s scaffolding—meetings, forecasts, teams. “Those things you hated held your life together,” Swearingen reflects. Without structure, days feel hollow. Only 40% find purpose, and it takes years: zero in the first two, 8% by year four, 50% after a decade.
Wasserstein’s fix? “Architect your life with the same precision as your business.” Mentor startups, join boards, or find hobbies with rhythm. Swearingen struggled: “A calendar event grinds when you crave freedom.” Experiment early to balance structure and flexibility. “Freedom without purpose is a prison,” Wasserstein warns.
Question 5: Where Will I Live?
Location shapes your life, but complexity kills. Swearingen’s four homes were a nightmare: “Everything needed fixing. A broken fountain meant constant repairs.” Their mantra is clear: choose a home base that fuels your values—family, community, adventure—without draining you. “I see mansions now and think, who maintains that?” Swearingen says.
Question 6: How Will I Redefine My Identity and Purpose?
The toughest question? Your identity. “Reflecting on who you are now is your biggest opportunity,” Wasserstein urges. Yet, 56% are happier post-exit, while nearly half miss being CEOs. Why? Success habits—control, optimization—sabotage retirement. Swearingen unlearned his fix-everything instinct: “You can’t spreadsheet head trash.”
Their data shows a 7.5 happiness score, barely above the U.S.’s 6.7. “Good energy is everything,” Swearingen says. “Chase experiences, not money.” Wasserstein adds: “More wealth won’t make you happier.” Without your business, who are you? Start answering now.
Plan Now or Regret Later
The biggest mistake? Waiting until the wire hits. “You can’t start planning early enough,” Wasserstein insists. “If you’re with bankers, you’re late.” Swearingen wishes he’d focused on energy, not dollars: “The world pushes more—money, houses, toys. They added stress, not meaning.”
Their case note is a wake-up call: “Post-exit life is a trade. The pros can be crushed by cons if you’re not ready.” Don’t let freedom become silence. Ask these six questions now, whether your exit is tomorrow or a decade out.
Listen Now, Thrive Later
AJ Wasserstein and Jeff Swearingen’s battle-tested wisdom is your lifeline. Their data-driven playbook, forged from mistakes and clarity, will save you from the regret haunting most entrepreneurs. Don’t miss Episode 439 of The Deep Wealth Podcast to master the six decisions that shape your future.
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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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