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

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 [e-mail]

 

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

[e-mail]

 

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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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.