Exit Tax Planning Starts With the Right Questions
How much will you actually keep? Does your stock qualify for QSBS? Is a secondary worth it?
Our four calculators are built for venture-backed founders navigating $20M+ exits. Run the scenarios yourself and compare your options.
KEYSTONE RECOGNITION
Capital Gains Tax Calculator
Estimate your federal and state capital gains tax on a startup exit, including how much you could eliminate through QSBS. Model long-term vs. short-term treatment, apply QSBS exclusion rules, and see state conformity side by side.
QSBS Eligibility Navigator
Not sure if your shares qualify? Walk through the core Section 1202 requirements (company structure, gross asset tests, holding period, and shareholder-level criteria) to understand your QSBS position.
QSBS Calculator
See how much QSBS could save you on your exit. Model the basic exclusion, legacy and post-OBBBA tiers, state conformity, and simplified stacking strategies across multiple taxpayers, all in one place.
Secondary Sale Calculator
Weighing a secondary sale or tender offer? Compare selling now versus holding to exit in after-tax dollars, accounting for QSBS timing, basis, state tax, and what happens if you reinvest your proceeds.
Run the Numbers. Then Let's Talk.
If running the numbers brought up questions you want to work through, let's have a conversation. The process is straightforward, low-pressure, and designed to give you clarity before you make any decisions.
Intro Call
30 minutes to make sure your situation matches our expertise. There's no pitch. Just an honest conversation about whether we're the right fit.
Discovery Meeting
We ask the questions most advisors skip: your equity structure, QSBS position, state exposure, timeline, and goals. We want to give you advice that's specific to your scenario.
Our Analysis
We take what we learned and build a custom plan. As independent fiduciaries, our only job is to find the best outcome for you.
Strategy Meeting
We walk you through what we found: tax savings opportunities, trust structures, QSBS strategies, and anything else on the table given your timeline.
Think on It
We're looking for long-term relationships, not quick closes. Take whatever time you need to make the decision that's right for you.
Going Live
Once you're ready, we start executing. For most clients, that means getting organized, opening accounts, and building out the full pre-exit plan before your deal closes.
What Founders Say About Us
Real outcomes from venture-backed founders who engaged Keystone years before their exits.
Partnering with Keystone completely transformed my exit outcome. Their team began planning years in advance, building a highly tailored QSBS and trust optimization strategy that leveraged multiple non-grantor trusts, charitable structures, and careful jurisdictional planning. Their depth of expertise meant every detail was anticipated and executed flawlessly, allowing my exit to unfold smoothly and with total confidence. We achieved more than $31 million in tax savings across multiple entities.
The QSBS, charitable, and state planning alone saved me $15M. Having Keystone in my corner starting 12 months out meant I could focus on building the company while they optimized everything on the personal side. I can't imagine going through an exit without this level of planning. I should have started working with them sooner.
Ready to Go Beyond the Calculator?
The tools give you a starting point. But founders with $20M+ exits almost always benefit from a deeper dive with someone who knows your cap table, your state exposure, and your timeline. Schedule a conversation today. No cost, no commitment.
