Beyond the K-1: Tax Strategy That Builds Investor Trust with Harisimran Khalsa

Avoid boot in your 1031 exchange before it triggers a surprise tax bill. Boot happens when you take cash out of the deal or your debt goes down. Either one can turn a tax-deferred 1031 exchange into a taxable event your investors never saw coming.

In this Wealth Unfiltered year-end tax planning finale, Harisimran Khalsa, CPA, President of Professional Services at SponsorCloud, explains how real estate sponsors can avoid 1031 exchange boot, when a reverse 1031 exchange makes more sense, and which tax strategies sophisticated sponsors use before year-end.

In This Episode, We Cover

  • 2:04 – Hari’s career path
  • 4:25 – Winning sponsor habits
  • 9:06 – Distribution tax myths
  • 12:12 – Tax season prep
  • 16:02 – Entity structure mistakes
  • 19:23 – Cost segregation explained
  • 21:57 – Depreciation recapture
  • 25:42 – Funds vs. SPVs
  • 30:17 – Opportunity Zones 2.0
  • 33:11 – Reverse 1031 exchanges
  • 36:09 – Real estate professional status
  • 43:02 – Why SponsorCloud

About Harisimran Khalsa

Harisimran brings 20+ years of finance and tax experience. At Ernst & Young, she led initiatives that generated over $50M in client tax savings. She has also served as VP Finance at Augmedix, Head of Finance at Housecall Pro, and CFO of KIIT Company Inc.

Find Harisimran Here

Listen to more Wealth Unfiltered for candid conversations about real estate investing, capital raising, wealth strategy, and the decisions that shape long-term financial success.

Disclaimer: This episode is for educational and informational purposes only and should not be considered individualized investment, legal, or tax advice. Consult qualified professionals regarding your specific circumstances.

Key Takeaways

  • Boot in a 1031 exchange happens when you take cash out of the deal or your debt goes down, and either one can turn a tax-deferred exchange into a taxable event.
  • A reverse 1031 exchange can make more sense than a traditional exchange in certain situations, and this episode explains when.
  • Sophisticated sponsors use year-end tax planning, including cost segregation and an understanding of depreciation recapture, to make tax outcomes more predictable for investors.
  • Entity structure matters: the conversation covers common structure mistakes and how funds compare with SPVs.
  • Distribution tax myths and tax season preparation are part of building investor trust.
  • Opportunity Zones 2.0 and real estate professional status round out the year-end planning picture.

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