Episode 58: "$15 Million in Capital Gains: Gone" Startup Wealth Strategist Bryan Hasling on What Angel Investors Need to Know About QSBS, Maximizing the Tax Benefits of a Losing Investment, and the Limits of Tax-Driven Deal Selection

Episode 58: "$15 Million in Capital Gains: Gone" Startup Wealth Strategist Bryan Hasling on What Angel Investors Need to Know About QSBS, Maximizing the Tax Benefits of a Losing Investment, and the Limits of Tax-Driven Deal Selection

March 31, 2026 · 52 min · Season 1 · Episode 58

About this episode

The episode discusses tax strategies for angel investors, focusing on QSBS and the benefits of 1244 losses.

Today's episode explores three ideas that caught my attention: The most important tax provision you’ve never heard of: 1244 losses. Bryan made the case (and I agree 100%) that most angels will benefit as much or more from ordinary income deductions on losses than from capital gains exclusions on wins.“We’re QSBS-eligible” is nice but not everything. Founders advertising QSBS eligibility can subtly distort investor judgment. Don’t let the tail wag the dog.QSBS claims are low-hanging fruit for ...

More episodes of The Diligent Observer Podcast

Explore listener stats, chart rankings, contacts and more on the The Diligent Observer Podcast podcast page.