When ETA entrepreneurs finally reach the exit they've spent years grinding toward, the tax decisions made in that moment can cost them millions — or save them millions.
Boulay Wealth Partner Nathan Faith breaks down the strategies many financial advisors don't know exist, from Flex SMAs that harvest losses, to the Section 1202 exclusion. If you're an ETA searcher anyhere on the journey — buying, running, or approaching an exit — this is the conversation that could change the financial outcome of everything you've worked for.
Key takeaways from this Search Party episode:
• Some newly wealthy ETA searchers don't know what to make of it. Even the most driven entrepreneurs can find themselves "hyperventilating" over numbers they spent years chasing but never quite believed would arrive, Faith says.
• Most post-exit ETA searchers opt not to run another business. According to Faith, most discover that the grind takes enough out of them that they'd rather invest in and mentor the next generation of searchers than saddle up again themselves.
• The 'three buckets' for ETA exit wealth. After Uncle Sam takes his cut, your exit proceeds belong in one of three places: taxes owed, an end zone fund sized to support you for life without working another day, and a legacy bucket where you can afford to take real risk again.
• How does a Flex SMA offset capital gains? A Flex SMA uses a margin loan to amplify your market exposure, then systematically harvests the resulting losses — in either direction — to offset the capital gain from your exit, potentially sheltering thirty to one hundred percent of your gain in the same tax year you report it.
• Entrepreneurs, ask your tax advisor about the 1202 gain exclusion. If you've held stock in a qualifying C corporation for at least five years, Section 1202 may allow you to exit with up to $15 million in profits completely tax-free — and most accountants either don't know it exists or don't bother to check whether you qualify.
• Ask your tax advisor about the 'stack and pack' strategy. By distributing shares into trusts established for each of your children before an exit, you may be able to turn a nine-figure exit into a tax-free event.
Access a full transcript and searchable content archive on the Search Party Substack.
Lead Sponsor:
NCL Partners https://www.nclpartners.com/
Sponsors:
Boulay https://boulaygroup.com/services/search-funds/
Kilpatrick https://ktslaw.com/
Oberle https://oberle-risk.com/landing-page/search-party/
#searchparty #eta #privateequity #tax
