Cracking the Code: Modern Strategies for Capital Gains Tax Deferral, with Brett Swarts

·48 min·4 clips

Justin Goodbread reveals how taxes prevent DecaMillionaire status and introduces an expert to crack the capital gains code.

Justin Goodbread introduces the episode by highlighting the common frustration with taxes eroding net worth for business owners. Guest Brett Swarts, author of 'Building a Capital Gains Tax Exit Plan', joins to discuss modern strategies for deferring capital gains taxes. Swarts begins by differentiating capital gains from income tax, using an analogy of building an asset without planning its exit like flying a plane with no landing place. He shares a poignant story about a client named Steve who lost his $50 million real estate portfolio and marriage during the 2008 financial crash due to lack of tax planning, linking it to Swarts' own family experience. Swarts then discusses the mindset shift needed, emphasizing not trading profitable assets for priceless time, illustrated by clients Warren and Catherine who sold a property to gain more family time. He outlines three key factors for successful tax planning: clear family mission/vision/values, defining truly passive income, and overcoming fear with faith. Swarts explains the Deferred Sales Trust strategy, which involves selling an asset to a third-party trust via an installment sale to defer taxes, increase cash flow, and allow investment diversification. He details how it works for assets like businesses, real estate, Bitcoin, or collectibles with at least $1 million in gain. Technical aspects are covered, including controls, fees, and tax implications on withdrawals. Swarts also touches on estate planning versions of the trust to avoid estate taxes and involve beneficiaries. The conversation includes philanthropic considerations, with Swarts advising careful alignment with values. Goodbread asks about timing, and Swarts recommends starting early, offering a no-obligation consultation. The episode concludes with resources and a call to action for listeners.

As heard by us

A focused conversation on tax planning, business value, and the clarity owners need before a sale.

Tax planning becomes the pressure point in this PlayNext episode, as Justin Goodbread and Brett look at what can happen when a service-based business reaches a $10 million-plus valuation and the owner is staring at a possible $2 million to $5 million tax bill.

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Why you'd press play

You want to think about a valuable business sale before the tax bill turns the win into stress.

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