How Founders Save Millions in Taxes using QSBS on Exit Day
  • Aug 13, 2025

How Founders Save Millions in Taxes using QSBS on Exit Day

0:00
0:00
Advertising will end in
play_arrow
pause
replay_10
forward_10
volume_up
volume_down
volume_off
share
speed
Skip ad
close
close
close
close
close
Share:

About Podcast

What if you could legally exclude up to $10 million from taxes when selling your startup? Richard Levychin from Galleros Robinson breaks down the Qualified Small Business Stock (QSBS) Section 1202 tax code that most founders overlook until it's too late. In this episode of Startups with Stu with host Stuart Draper, Richard explains how proper entity structure and timing can save entrepreneurs millions during exit events, sharing real cases where clients turned $100K investments into $9 million payouts. Stuart Draper explores the critical setup requirements, five year holding periods, and conversion strategies for LLCs and S-Corps looking to qualify. From Delaware C-Corporation benefits to advanced tax mitigation techniques rated on a 1 to 10 risk scale, this conversation delivers actionable insights for companies in their growth stage. Richard also reveals common due diligence pitfalls that kill deals and why having the right advisory team makes the difference between keeping your wealth and losing it to Uncle Sam.

Follow Richard Levychin:
LinkedIn: https://www.linkedin.com/in/richard-levychin-cpa-cgma-b22386/

Follow Startups with Stu:
Website: https://www.startupswithstu.com/

YouTube: https://www.youtube.com/@StartupsWithStu
Instagram: https://www.instagram.com/StartupswithStu/

Follow Stuart Draper:

LinkedIn: https://www.linkedin.com/in/draperstu/
Instagram: https://www.instagram.com/draperstu/

Related Episodes

This Founder Raised $5.6 Million in Seed Round Seven Years After Launch

This Founder Raised $5.6 Million in Seed Round Seven Years After Launch

What does it take to bootstrap a startup for five years and then raise millions in funding? Shane Murphy, founder of Boostly, reveals his extraordinary journey from living frugally to revolutionizing restaurant marketing. Discover the unexpected benefits of joining Y Combinator and learn how to maintain control through multiple funding rounds. Join Shane and Stu as they dive deep into pivoting products, scaling sales teams, and the art of the startup exit. Gain invaluable insights on bootstrapping, fundraising, and building a business poised for exponential growth to fuel your startup success.

Play
The Unconventional Marketing Tactics That Built An 8-Figure EdTech Company

The Unconventional Marketing Tactics That Built An 8-Figure EdTech Company

We showed up to conferences and we had humans all over our booth. So many humans that our neighbours were complaining" - this is how Trevor Erikson describes Stukent's early disruptive entry into the academic publishing space, where he served as the company's first hire and CMO. From pioneering personalized marketing campaigns (including tracking down professors' favorite candy bars from around the world) to scaling email strategies that helped grow Stukent to tens of millions in valuation, Trevor reveals the innovative tactics that transformed a basement startup into an educational technology leader serving over a million students. His experience juggling side hustles while building companies offers a real playbook for both marketers and founders. Now at Deviant Ink, he's proving that mixing digital innovation with passion markets is a winning formula. For entrepreneurs looking to scale through authentic marketing, this episode shows why personal touches and real connections beat conventional marketing every time.

Play
$200M Without a Single Investor: The Marketing Genius Behind Portland Leather Goods

$200M Without a Single Investor: The Marketing Genius Behind Portland Leather Goods

"You're not a marketing genius. You don't even have a job. You do yoga all the time." These were the words Curtis Matsko's girlfriend hurled at him when he boldly declared he was going to quit his job and start a hundred-million-dollar company selling leather journals. Her response? "That's the stupidest idea ever." Fast forward to today, and Curtis Matsko didn't just prove her wrong - he built a $200 million global leather goods empire that sells one product every three seconds on Black Friday. From hustling at art festivals to building a 600,000 square foot international operation, Matsko's journey is a masterclass in entrepreneurial audacity and marketing genius. What happens when you ignore everyone who says your idea is crazy and instead bet everything on your vision? By treating marketing as his primary product and breaking through every limitation, Curtis reveals the unconventional strategies that transformed Portland Leather Goods from a garage startup to a rapidly expanding brand. With raw honesty and infectious energy, he shares critical lessons about surrounding yourself with motivated people, breaking through your own expectations, and why data should always serve decision-making. This isn't just another startup story - it's a blueprint for turning seemingly impossible dreams into world-changing businesses. If you're an entrepreneur looking for real-world inspiration and tactical insights, this episode will light a fire under your ambitions.

Play

Comments