Mark had poured three decades into building his business. When the opportunity came to sell, the deal felt right—but also overwhelming.

He now had a significant amount of liquidity for the first time in his life, and a lot of new questions:

• How do I turn this into long-term income?
  
• What’s the smartest way to handle taxes on the sale?
  
• Do I need to start investing immediately—or wait?
  
• What’s next for me personally and financially?
  

Mark didn’t want to go it alone, and he didn’t want “just an investment guy.” He wanted a team that understood the full picture—income, tax strategy, lifestyle goals, and legacy.

The Challenge

While Mark felt relieved and proud of his successful exit, he also knew that a windfall without a plan can become a burden.

He needed:

• A way to structure his income now that there were no paychecks
  
• A tax strategy to spread out the impact of the sale over multiple years
  
• Help deciding how much to set aside vs. invest
  
• Guidance on when to start Social Security or leverage Roth conversions
  
• A clear path forward, especially as he considered part-time consulting and travel
  

Our Approach

We began by understanding the deal terms, working closely with Mark’s CPA to model out the after-tax proceeds and identify opportunities to reduce his long-term tax exposure.

Then we:

• Created a bucket strategy to allocate funds for near-term needs, mid-term goals, and long-term growth
  
• Implemented tax-loss harvesting and charitable giving strategies to offset capital gains
  
• Designed a custom income stream that matched his lifestyle plans and withdrawal needs
  
• Helped him evaluate future consulting work within the context of his tax bracket and retirement goals
  
• Built a comprehensive financial dashboard so Mark could see exactly how his money was working—without feeling like he had to go back to managing a business
  

The Result

Mark now says he feels the same kind of peace of mind he had when his business was running smoothly—only now, he doesn’t have to be the one doing the work.

He has a retirement income system that adjusts with his needs, a tax plan that looks years ahead, and the confidence that his wealth is aligned with his life—not just the market.

Note: This case study is hypothetical and does not involve an actual Demars Financial client. No portion of this content should be interpreted as a guarantee of specific outcomes.