Brett Swarts is a best-selling author of Building the Capital Gains Tax Exit Plan and host of two finance podcasts. We spoke about how entrepreneurs, investors, and even Bitcoin holders can legally defer millions in taxes when selling highly appreciated assets. As founder of Capital Gains Tax Solutions, Brett has helped close over half a billion dollars in transactions.

He explained why traditional tools like the Delaware Statutory Trust often fail business and crypto owners, noting, “It ties up your capital for five, seven or ten years with no diversification.” Instead, he advocates the Deferred Sales Trust (DST), based on IRS code 453, which allows sellers to act as “the bank” and only pay tax when they receive payments. He shared how one Bitcoin owner avoided a $1.85M tax hit and redirected the proceeds into a startup venture.

For Brett, the real value lies in freedom and purpose. “You spent 5, 10, 20 years building your business… the government wants to take 40%,” he warned, before showing how a few hours of planning can preserve wealth, fund new ventures, and even eliminate estate taxes. This conversation offers clear, practical insight for anyone facing a major exit.

Key takeaways

• Why Delaware Statutory Trusts are too inflexible for entrepreneurs and crypto owners
• How Deferred Sales Trusts use IRS code 453 to legally defer taxes
• Real case: $50M Bitcoin exit with $1.85M tax deferred
• Steps to calculate your true gain before planning a sale
• How DSTs let you diversify into ventures, real estate, or stocks
• Strategies to reduce both capital gains and estate taxes permanently