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Welcome back fellow investopreneurs!

Let’s get one thing straight:
You don’t need venture capital to make a big exit.
You just need to play the game like an investor.

And if you’re not planning your exit from day one with tools like QSBS and trust stacking, you're probably going to leave millions on the table—millions you could have kept tax-free.

That’s why I kicked off Episode 1 of Bootstrapping to Billions with Alessandro Chesser of GetDynasty.com, because this one legal loophole—called QSBS—might be the greatest wealth hack most founders still don’t know about.

Let’s break it down like we did on the show:

What is QSBS (and Why Should You Care)?

QSBS stands for Qualified Small Business Stock, and it’s the tax code’s way of rewarding founders, early employees, and investors who take a bet on building small companies.

Here’s the juicy part:
If your stock qualifies and you hold it long enough, you can exclude up to $10 million—or even $15 million (as of July 4, 2025)—in capital gains from federal taxes.

No, that’s not a typo.
$15M in gains. Zero federal tax.
And in 45 states? Zero state tax too.

The Why Behind QSBS

This isn't some shady loophole. It was baked into the U.S. tax code in the 1990s to fuel startup investment.

Think about it:
If the government wants people betting on risky, innovative businesses instead of stuffing money into S&P index funds, they need to make it worth your while.

QSBS is the carrot.
And with the latest update (post-July 4, 2025), the carrot just got even juicier.

Do You Qualify for QSBS?

Here’s the checklist:

• ✅ You’re a C Corporation (not an LLC or S Corp)

• ✅ You acquired shares when the company had < $50M in assets (or <$75M after July 4, 2025)

• ✅ You hold the shares for at least 5 years (or 3 years for partial exemption post-2025)

• ✅ You’re not in an excluded industry (e.g., financial services, law, etc.)

• ✅ You got the shares directly from the company (founder or investor stock, not secondhand)

If that’s you? You’re sitting on a tax-free exit waiting to happen.

Bootstrappers, You’re Sitting on a Goldmine

I get it—you’re building without outside funding. That’s the point.

But here’s where things get interesting:
QSBS isn’t just for VCs.
If anything, you stand to benefit the most—because you own a bigger chunk of your company.

Let’s say you build a business and sell it for $10M.
With QSBS, that entire $10M could be tax-free.
Without it? You could owe $2.3M+ in federal taxes alone.

That’s the difference between retirement and still hustling.

Trust Stacking: The Move Nobody Talks About

Here’s where Alessandro blew my mind.

QSBS gives you a $10M–$15M exemption per person or trust.
So what do the wealthy do?
They stack trusts.

You can gift shares to irrevocable trusts for your kids, your spouse, your dog (okay, maybe not the dog). Each trust gets its own exemption.

Four trusts? $60M in tax-free gains.

And don’t worry—you can still manage the money:

• Pay yourself a salary from the trust's LLC

• Borrow from the trust (and pay it back to yourself)

• Buy a house through the trust, pay rent to the trust…
  (Yes, this is real. No, it’s not a scam.)

Timing is Everything

The biggest mistake I see bootstrappers make?

Waiting too long.

QSBS benefits only kick in after you start the clock.
That means forming a C Corp, getting a valuation, issuing stock—and if you're trust stacking—gifting shares early.

Pro tip: Get a third-party valuation done (Carta works) to document your cap table and set your QSBS eligibility. It costs maybe $1,000 and saves millions later.

What’s New in the 2025 Update?

Congress went full “Build Back Better 2.0” with the July 4, 2025 changes. Here’s what’s new:

• 💰 Exemption increased to $15M

• ⏳ Partial exemptions now possible at 3 and 4 years

• 📈 Gross asset cap raised to $75M

• 🔁 Rollover option: Sell early? You can reinvest gains into another QSBS-eligible company and defer taxes (1031-style)

Translation: more founders can qualify, more upside is protected, and the window for planning is wider than ever.

How to Set It All Up (Without Getting Ripped Off)

Traditional estate planning firms will charge $30K–$100K+ for what Alessandro’s team at GetDynasty.com does for $1,500.

Here’s the step-by-step:

1. Go to GetDynasty.com

2. Pay $1,500 for up to 4 Nevada-based irrevocable trusts

3. Choose your beneficiaries

4. Do a kickoff call

5. Get your gift valuation done (via Carta)

6. Get board approval

7. Transfer the shares

Boom—QSBS stacked, dynasty built.

Final Word: Stop Building for the IRS

If you’re building a valuable business and don’t have a plan to protect that value, you’re basically building for the government.

QSBS is how you flip the script.
You keep your upside, reward your family, and build multi-generational wealth the legal, ethical, totally above-board way.

Your Move:

• Already a C Corp? Set up trusts today.

• Still an LLC? Time to consider converting.

• Not sure where to start? Go watch Episode 1 of Bootstrapping to Billions and connect with Alessandro on LinkedIn or at GetDynasty.com.

This is the game they don’t teach in school.

But we’re teaching it now—one episode at a time.

— Chris
Founder of Bootstrapper.ai | Host of Bootstrapping to Billions
"Build Equity. Unlock Capital. Exit With Ownership."

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