Tax Flow, Not Just Cashflow: How to Exit Smart and Buy Back Time with Brett Swarts

Jim Oliver sits down with Brett Swarts to tackle the part of exiting most owners ignore until it’s painful: Taxes. Brett is the founder of Capital Gains Tax Solutions, a real estate broker and tax strategy specialist with deep expertise in Deferred Sales Trusts (DST), Delaware Statutory Trusts, and 1031 exchanges. He hosts the “Build It to Billions” and “Capital Gains Tax Solutions” podcasts.

Together, Jim and Brett lay out how purpose-driven entrepreneurs can engineer an exit that prioritizes tax flow, converts to truly passive income, and preserves control and flexibility.

What You’ll Learn:
- Why most CPAs “report the score” and how a true tax strategist changes outcomes
- Tax flow vs. cashflow: deferring cap gains to compound what would’ve gone to the IRS
- A “2.0” exit for larger deals: using a Deferred Sales Trust for cap gains and estate tax planning
- When 1031s become a “shotgun wedding”—and smarter blends (partial 1031 + DST + cost seg)
- How to define and build TPI (truly passive income) so your time, not the asset, drives your life

Action Steps:
1. Build the Exit Blueprint
Quantify net proceeds, gain, debt, and estate exposure. Set a clear monthly TPI target before signing an LOI.

2. Upgrade the Bench
Add a tax strategist alongside CPA/attorney. Evaluate DST, partial 1031, bonus depreciation, and insurance—pick tools, not dogma.

3. Allocate for TPI
Diversify post-sale capital into vehicles that deliver durable, hands-off cashflow while keeping optionality for future deals.

Brett Swarts’ Final Word
“Truly passive income is to your freedom and impact what compounding interest is to your money. Lead with tax flow—and let it compound.”

Chapters
00:00 Introduction to Tax Flow Strategies
02:46 Understanding Capital Gains Tax and Its Implications
05:30 Evaluating Real Estate Strategies and Tax Exemptions
08:28 Navigating High Net Worth Exits and Estate Tax Challenges
11:39 The Importance of Flexibility in Tax Strategies
14:25 The Role of Passive Income in Wealth Management
17:25 Legal Considerations and Audit Defense in Tax Strategies
20:14 Transformational Outcomes of Deferred Sales Trusts
23:08 The 3D Mindset: Cash Flow, Tax Flow, and Debt Flow
25:52 Building a Capital Gains Tax Exit Plan
28:58 Final Thoughts and Advice for Entrepreneurs

Connect with Brett Swarts:
Website: https://capitalgainstaxsolutions.com/
Website https://brettswarts.com/
YouTube: http://www.youtube.com/@CapitalGainsTaxSolutions
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