Small Business Tax Savings Podcast Sell Your Company with $0 Taxes? QSBS Explained
9 snips
Sep 3, 2025 Alessandro Chesser, a tax strategist from Get Dynasty, dives into the world of Qualified Small Business Stock (QSBS) – a powerful tool that can enable entrepreneurs to sell their companies tax-free. He explains who qualifies and how specific industries can benefit, along with recent changes that raised exclusion limits and introduced strategic planning around trusts. Listen to learn about the best timing for QSBS and how to turn a transition from LLC to C-Corp into substantial tax savings!
AI Snips
Chapters
Transcript
Episode notes
QSBS Is A Massive Federal Exclusion
- Qualified Small Business Stock (QSBS) can exclude up to $10M (older rules) or $15M (new rules) of federal capital gains for qualifying startup founders, employees, and investors.
- Qualification depends on industry (tech/innovation favored), asset limits, and holding period requirements that recently changed.
Consider Timing Before Flipping To C‑Corp
- If you're an LLC or S‑Corp planning an exit, consider flipping to a C‑Corp to gain QSBS benefits but expect the five‑year holding clock to restart.
- Evaluate tradeoffs between current pass‑through tax advantages and potential future QSBS exclusions before converting.
Founder Example: $14M Became $126M QSBS
- Get Dynasty's founder described flipping her own LLC into a C‑Corp during a priced VC round to capture QSBS value.
- That flip converted a $14M pre‑money valuation into $126M of QSBS eligibility shared among founders.