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Ep 305 Mid 8-Figure Exit Lessons: How to Avoid Millions in Taxes and Regret After the Sale with Nathan Collins

Profit Answer Man: Scaling with Profit First & Beyond

Release Date: 01/21/2026

Ep 305 Mid 8-Figure Exit Lessons: How to Avoid Millions in Taxes and Regret After the Sale with Nathan Collins

Profit Answer Man: Scaling with Profit First & Beyond

Mid 8-Figure Exit Lessons: How to Avoid Millions in Taxes and Regret After the Sale with Nathan Collins Find Rocky Lalvani @ or email him at Most business owners think the hardest part of selling a business is the deal. But the real danger often shows up after the sale: the taxes you didn’t plan for and the identity shift you didn’t expect In this episode of Profit Answer Man, Rocky Lalvani sits down with , a former CEO who sold his business for a mid-eight-figure exit—and then realized he wasn’t personally...

Ep 304 From Bankruptcy at 24 to $35M: Building Profitable Business Through Discipline and Purpose with Mike Chaput

Profit Answer Man: Scaling with Profit First & Beyond

Find Rocky Lalvani @ or email him at From Bankruptcy at 24 to $35M: Building Profitable Business Through Discipline and Purpose with Mike Chaput What if the worst business failure of your life became the foundation for 26 years of unbroken profitability? At 24, Michael Chaput bought a business that went bankrupt. At 50, he runs a $35 million company that hasn't had a single unprofitable month in 26 years—not through 2008, not through COVID, not ever. In this episode, Michael shares the hard-won lessons from hitting rock bottom and how financial discipline, tough...

Ep 303 How to Legally Pay Less Tax as a Business Owner with Former IRS Agent Carlotta Thompson

Profit Answer Man: Scaling with Profit First & Beyond

How to Legally Pay Less Tax as a Business Owner with Former IRS Agent Carlotta Thompson With Former IRS Agent Carlotta Thompson Most business owners believe high taxes are just the price of success. They’re wrong. In this episode of Profit Answer Man, Rocky sits down with former IRS agent turned tax strategist Carlotta Thompson to reveal how the tax system really works, what actually triggers audits, and how profitable business owners legally keep more of what they earn. This is not about loopholes or risky moves. It’s about understanding the rules well enough to play the...

Ep 302 The Financial Model Every 7–8 Figure Business Needs for Predictable Profit with Salvatore Tirabassi

Profit Answer Man: Scaling with Profit First & Beyond

The Financial Model Every 7–8 Figure Business Needs for Predictable Profit with Salvatore Tirabassi Most business owners don’t lack data. They lack clarity. They have a P&L, a balance sheet, maybe even a dashboard. But when a real decision shows up—Can I afford this hire? Should I scale marketing? Why did margins drop again?—the numbers don’t give a clear answer. That’s where growth starts to feel chaotic. In this episode of Profit Answer Man, Rocky Lalvani sits down with fractional CFO and former private equity investor Salvatore Tirabassi to unpack...

Ep 301 How to Build a Business Fortress: Liquidity, Cash Flow, and Exit Readiness with David Barnett

Profit Answer Man: Scaling with Profit First & Beyond

How to Build a Business Fortress: Liquidity, Cash Flow, and Exit Readiness with David Barnett Build a Business Fortress: Why Liquidity Beats Leverage and Most Businesses Never Sell Most owners assume the big payoff will come when they finally sell the business. The hard truth is that roughly 80 percent of small businesses listed for sale never actually sell as going concerns. The real payoff is in the years of ownership: the cash flow you extract, the wealth you build outside the business, and the resilience you create so you can survive the next punch in the face. In this...

Ep 300 The Referable Client Experience with Stacey Brown Randall

Profit Answer Man: Scaling with Profit First & Beyond

The Referable Client Experience with Stacey Brown Randall Most business owners say they want more referrals. Very few are actually drowning in them. The default strategy is to do good work, hope people notice, and maybe ask for introductions when things get slow. In this episode of Profit Answer Man, I sit down again with referral expert and author Stacey Brown Randall to talk about why that approach does not work and how to build a truly referrable client experience. Stacey has spent years helping small business owners generate referrals without asking, without incentives, and...

Ep 299 How to Build a Business You Can Actually Sell with Saul Cohen

Profit Answer Man: Scaling with Profit First & Beyond

How to Build a Business You Can Actually Sell with Saul Cohen Most business owners say the same thing: “I want to grow as big as I can.” But when you press them on what they really want—time freedom, a great income, flexibility with their family—they’re actually describing a lifestyle business, not a high-growth scale-up destined for a huge exit. In this episode of Profit Answer Man, Rocky Lalvani talks with Saul Cohen, an accountant and advisor who helps ambitious entrepreneurs grow through acquisition and prepare for a successful exit. Together, they unpack the...

Ep 298 From Chaos to Cash Flow: How Business Owners Can Scale with Less Stress with David Forster

Profit Answer Man: Scaling with Profit First & Beyond

From Chaos to Cash Flow: How Business Owners Can Scale with Less Stress with David Forster “Slow is smooth, smooth is fast.” If you’re stuck reacting all day, this episode with David Forster hands you the blueprint: clarify roles, codify the 80%, install scorecards that measure what matters, and make Profit First automatic so cash is where you need it—when you need it. In This Episode, You’ll Learn: Why “boring, repeatable systems” beat heroics—and how to build them for people who crave structure. The clarity–consistency–accountability trio: what...

Ep 297 Profit First with Megan Schwan

Profit Answer Man: Scaling with Profit First & Beyond

Profit First with Megan Schwan Most owners chase revenue and wonder why cash keeps disappearing. In this episode, Rocky sits down with Megan Schwan—CEO of Sidekick Accounting and a certified Profit First Professional—to unpack the simple systems that turn chaos into cash: clean books, pricing discipline, expense sweeps, and a short list of actionable KPIs. If you want fewer surprises and fatter reserves, start here. In This Episode, You’ll Learn: Why “good books” are your #1 tax saver—and the foundation for pricing and fraud control. How Profit First creates...

Ep 296 Simple Numbers, Big Profits with Greg Crabtree: How to Scale Without Debt or Chaos

Profit Answer Man: Scaling with Profit First & Beyond

Simple Numbers, Big Profits with Greg Crabtree: How to Scale Without Debt or Chaos Most business owners chase revenue—and lose sight of profit. In this episode of Profit Answer Man, Rocky Lalvani sits down with Greg Crabtree, author of Simple Numbers, Straight Talk, Big Profits, to cut through the noise and talk about what really drives a successful business. A self-described “recovering accountant,” Greg shares how data—not opinions—can transform how entrepreneurs see their numbers, make decisions, and grow sustainably. If you’ve ever felt like your financial reports...

More Episodes

Mid 8-Figure Exit Lessons: How to Avoid Millions in Taxes and Regret After the Sale with Nathan Collins

Find Rocky Lalvani @ www.ProfitComesFirst.com or email him at rocky@profitcomesfirst.com

Most business owners think the hardest part of selling a business is the deal.

But the real danger often shows up after the sale:

the taxes you didn’t plan for
and the identity shift you didn’t expect

In this episode of Profit Answer Man, Rocky Lalvani sits down with Nathan Collins, a former CEO who sold his business for a mid-eight-figure exit—and then realized he wasn’t personally prepared for what came next. Nathan shares what he wishes he’d done differently, how business owners should think about diversifying outside the business, and why “exit readiness” is about far more than financials.

In This Episode, You’ll Learn:

Why many business owners hesitate to take money out of the business and invest elsewhere—and how that lack of diversification increases risk.
The difference between preparing your business for sale vs preparing your life for the exit.
The common “cheap” mistake founders make that can cost millions in avoidable taxes.
Why your CPA and financial advisor often don’t proactively plan together—and how that gap hurts business owners.
What happens emotionally the day after the sale (and why so many owners feel lost even after a big win).
The “liminal phase” after an exit—and how to prepare for it with purpose, community, and health.
How systems like EOS/Traction and having the right people in the right seats can make your company stronger—and more sellable.
Why many exits are forced (not planned) and why “exit-ready” equals resilience.

The Big Takeaway:

A profitable exit is not the finish line.

If your identity, purpose, and community are built entirely around your company, selling can create a void—fast. And if you haven’t done personal tax planning ahead of time, the IRS can take a bigger share than necessary.

Exit planning is not just about maximizing the sale price. It’s about being ready financially and personally—so you can enjoy the outcome you worked so hard to create.

Bio:

Nathan Collins is a wealth manager at Raymond James and a former CEO who sold his business through a successful middle-market process. He now helps business owners optimize business value, plan for liquidity events, and avoid the costly personal and financial mistakes that often happen around exits.

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

Conclusion:

Whether you plan to sell in 3 years or 30 years, the best time to prepare is now. Build a business that can run without you, diversify so you’re not financially trapped in one asset, and make sure you’re building a life you actually want to “retire into.”

#ProfitAnswerMan #ProfitFirst #BusinessProfit #CashFlow #BusinessOwners #ExitPlanning #TaxPlanning #WealthManagement #EOS #Traction

Watch the full episode on YouTube: https://www.youtube.com/@profitanswerman Source

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Relay Bank (affiliate link):

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My podcast about living a richer more meaningful life: http://richersoul.com/ Source

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.

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