Episode 305 | The Profit Answer Man
Selling your business can be one of the most rewarding moments of your entrepreneurial life—and one of the most disorienting. In this episode of The Profit Answer Man, host Rocky Lalvani sits down with wealth manager and former CEO Nathan Collins, who shares what happened after he sold his company for a mid-eight-figure exit… and why he wishes someone had warned him earlier.
Nathan’s story is a masterclass in two areas most entrepreneurs don’t plan for enough: (1) tax and financial preparation and (2) the emotional impact of exiting a business. If you’re building a company you may sell someday—or if you simply want a stronger, safer business today—this episode is for you.
In This Episode, You’ll Learn
Nathan breaks down the two biggest categories of mistakes he made—and how business owners can protect themselves:
1) Why business owners hesitate to invest outside their company
Rocky challenges a common pattern: many entrepreneurs would rather buy equipment (like a vehicle) than fund retirement accounts or invest profits outside the business. Nathan explains the mindset behind it—bootstrapping habits, uncertainty, and the perceived tax advantages of keeping money in the business.
He also points out that for highly profitable businesses, there may be retirement plan options that allow very large tax-advantaged contributions—far beyond what many owners realize.
2) The #1 exit mistake: planning the sale, but not planning your life
Nathan did a lot right operationally: investment banker, M&A attorney, and quality-of-earnings support. Where he fell short was personal preparation—especially around taxes—leading to millions in avoidable taxes (especially painful given New York City’s high tax burden).
He’s blunt about the root causes: “personal arrogance” (thinking he knew enough) and being “cheap” (not engaging the right advisors early).
3) The emotional crash after an exit (the part nobody talks about)
This is where the conversation gets powerful.
Nathan describes the day after you sell: the wire hits your account, it feels amazing… and then the feeling fades quickly. Suddenly, no one calls. Your title is gone. Your identity changes overnight.
He shares that he personally went through years of depression-like feelings—not necessarily clinical, but deeply difficult—and explains why it’s so common for founders to struggle after they exit.
The “Liminal Phase” (and Why Entrepreneurs Regret Selling)
Nathan references research describing a post-exit “liminal phase”—a transition period marked by uncertainty, regret, confusion, and loss of identity. He also cites that many owners regret selling within a year, not because the deal was bad, but because they weren’t prepared for what came next.
Rocky connects this to a principle he emphasizes on his other show: you don’t retire from something—you retire to something. Time off is great, but you need a real “next chapter” plan.
The 3 Drivers of Real Fulfillment After an Exit
Nathan offers a simple framework for thriving after entrepreneurship:
Purpose — something bigger than yourself
Community — relationships outside your company
Health — mental and physical wellbeing (starting now, not “someday”)
His point is one every entrepreneur needs to hear: personal prosperity doesn’t automatically create personal fulfillment.
How Nathan Built a More Valuable (and More Sellable) Company
When Rocky asks how Nathan revitalized the business he took over, Nathan doesn’t claim brilliance—he credits:
- Building the right team (even if it took time and turnover)
- Aligning people around vision
- Implementing structured operating systems, including principles from Traction / EOS
- Creating predictable communication rhythms so the business could run without him Source
That’s the essence of an exit-ready business: it isn’t dependent on the owner.
A Reminder: Many Exits Are Forced (Not Planned)
Rocky and Nathan also touch on a critical reality: many business owners don’t sell because they’re ready—they sell because life forces a decision (health, conflict, cashflow, etc.). That’s why building an exit-ready business is not just about selling—it’s about resilience and options.
Don’t wait until the wire hits to realize you weren’t prepared.
Nathan sold his business for a mid-eight-figure exit—and still paid millions in avoidable taxes because he didn’t plan personally ahead of time. Listen to the full interview here: ————
Connect with Nathan Collins
Nathan says the easiest way to reach him is via email: nate.collins@raymondjames.com and he can also be found on LinkedIn by searching his name + Raymond James. He also invites listeners to attend his free quarterly business exit planning workshop webinar, which includes an interactive workbook and action steps.
Links:
Website: https://www.raymondjames.com/founderwealthstrategies/
LinkedIn https://www.linkedin.com/in/nate-collins/
Exit Planning Workshop Webinar: https://www.raymondjames.com/founderwealthstrategies/events
nate.collins@raymondjames.com
Hear Nathan Collins’ real-world lessons from a mid 8‑figure business exit—what he wishes he’d planned (taxes) and what nobody warned him about (identity after the sale).
👉 Listen here: EP 305: https://profitcomesfirst.com/ep-305-mid-8-figure-exit-lessons-how-to-avoid-millions-in-taxes-and-regret-after-the-sale-with-nathan-collins/
Watch the full episode on YouTube: https://www.youtube.com/@profitanswerman
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Music provided by Junan from Junan Podcast
Any financial advice is for educational purposes only and you should consult with an expert for your specific needs.