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

Today's episode explores three ideas that caught my attention:

1. 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.
2. “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.
3. QSBS claims are low-hanging fruit for IRS audits. Claiming a zero-tax outcome on a big winner almost guarantees scrutiny. Make sure your documentation is in order.

I explore these ideas and more with Startup Wealth Strategist Bryan Hasling. Bryan Hasling is a Partner at Modern Financial Planning, a firm specializing in advanced tax and wealth management for families navigating the complexities of tech careers and startup equity. As both a practicing wealth advisor and an active angel investor with roots in Silicon Valley, Bryan brings a rare perspective: he lives on both sides of the table, helping clients extract maximum after-tax value from their investments while making those same bets himself. His work sits at the intersection of early-stage portfolio strategy and tax code fluency, giving him a uniquely practical lens on the tools many angels leave on the table. 

During our conversation, Bryan shares:

• A breakdown of the five qualifying criteria a startup must meet to be considered a Qualified Small Business, including why the $75 million gross asset threshold matters more than most investors realize and how easy it is to accidentally miss it.
• The case for why 1244 ordinary income losses are arguably the more relevant tax tool for most angel portfolios, offering up to $100,000 in deductions for married filers against regular income when a startup shuts down.
• A practical documentation protocol for angel groups, including which records to collect at the time of investment to build an audit-ready file long before a liquidity event forces the issue.

Connect with Bryan: 

LinkedIn | Website

Stuff We Reference

• Qualified Small Business Stock (QSBS) – Section 1202
• One Big Beautiful Bill Act (OBBBA)
• John Harbison
• What does the Big Beautiful Bill Mean for Angel Investors? –A special podcast episode 

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All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice.