The Broke Millionaires

E49 | We Don't Sell Properties. So Why Are We Selling This One?

Lauryn & Joshua Massari Episode 49

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What happens when a fully permitted, ground-up rebuild in one of California's most in-demand neighborhoods stops making financial sense to hold — and selling it could generate up to $800K tax-free? In Episode 49, we pull back the curtain on the exact strategy we're exploring to make that happen, plus the creative finance scandal making national news, the hidden IRS tax trap destroying sellers in 0% seller-finance deals, and a $2,000 education savings strategy that could fund years of private school tuition completely tax-free.

What You'll Learn:

  • Why irresponsible sub-2 investors are causing innocent sellers to face foreclosure — and what ethical creative finance looks like
  • The IRS imputed interest rule creating hidden tax bills in 0% seller-finance deals
  • How bonus depreciation (back for 2026) can legally eliminate a six-figure capital gains tax bill
  • Why we didn't sell last year — and why this summer may be the right window
  • What a cost segregation study is and how to use it to turn tax liability into new investment properties
  • The honest math behind a property that barely cash-flows despite renting for $13,500–$15,000/month
  • The Coverdell ESA strategy: how $2,000 could fund 12+ years of private school and college tuition tax-free
  • How HostShare and Home Exchange funded a family snow trip for nearly free
  • Why we shifted from equity-building to cash-flow-focused investing — and what that means for our next moves
  • The free School community we're launching: weekly office hours, Q&A, and deeper dives on every episode topic

Resources & Links:

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Legal Disclaimer:

This podcast is for informational and entertainment purposes only. Nothing discussed constitutes financial, legal, tax, or investment advice. Consult a licensed CPA, financial advisor, or attorney before making any investment or tax decisions. Real estate investing involves risk, including potential loss of capital.