Financial Expert Reveals Shocking Truth About Equity Compensation | Stock Options

Answer Box: TL;DR

Equity compensation and variable pay can be an incredible wealth builder—or a major missed opportunity. In this video, Dan explains why bonuses, commissions, and equity packages (ISOs, NSOs, RSUs, etc.) require a deliberate strategy: understanding how bonuses are really taxed, how and when to exercise and sell equity, how to benchmark your total comp, and how to use lower-income transition periods for tax planning moves like Roth conversions. The core message: don’t just earn a big package—turn it into lasting, after-tax wealth with a real plan.

Key Takeaways

Bonuses and commissions are taxed differently than salary.
- Most bonuses are treated as supplemental wages and withheld at a flat rate (often around 22%).
- If you’re actually in a higher tax bracket (e.g., 32%–37%+), that flat withholding can leave you under-withheld.
- Result: a surprise tax bill at filing time if you don’t plan ahead.
Timing your bonus can be a tax lever.
- If you can negotiate when a large bonus is paid (this year vs. next, early vs. late), you may be able to land it in a lower-income year.
- That can reduce your marginal tax rate on the bonus and potentially save you thousands.
Equity compensation is powerful—but unpredictable.
- We all hear the big win stories, but reality often includes market downturns, disappointing exits, or underperforming stock.
- Without a clear strategy, professionals end up with far less than they expected from “great” equity packages.
- You need a plan for when to exercise, when to sell, and how to reinvest proceeds.
Benchmarking your comp is about more than averages.
- Industry averages are a starting point, not the full story.
- Your role, company trajectory, stage, risk profile, and equity structure all influence what “good” compensation really is.
- Dan encourages looking beyond base salary to the full package: cash, bonus, equity, and upside.
Career transitions are hidden tax-planning windows.
- Lower-income periods between roles can be ideal for Roth conversions and other tax moves.
- In those years, you may pay tax at a lower rate to shift money into tax-free growth for the future.
- Thoughtful planning during transitions can create six- or seven-figure long-term benefits.
Bottom line: your comp package is a wealth engine—if you plan it.
- Bonuses, variable comp, and equity are complex, but with the right strategy they can become one of your most powerful wealth-building tools.
- Without a strategy, you risk unnecessary taxes, poor timing, and underused opportunities.
- Sales leaders and go-to-market executives should treat compensation management like a core part of their financial plan, not an afterthought.

Key Moments

(00:00) – The real question about equity comp. Dan opens by reframing the focus from “how much you make” with stock options to “how much you actually keep” after taxes and strategy.
(00:00–00:36) – Dan’s background & who he helps. He introduces himself as founder and CEO of Tailored Wealth and a former CRO/sales leader, highlighting his experience with bonuses, variable comp, equity, and transitions.
(00:36–01:11) – How bonuses are really taxed. Dan explains that bonuses are classified as supplemental wages and often withheld at 22%, which can be far below the true tax rate for high earners.
(01:11–01:50) – Smart timing for big bonuses. He suggests that, where possible, negotiating bonus timing into a lower-income year can meaningfully reduce taxes.
(01:50–02:25) – Equity reality vs. equity hype. Dan contrasts the success stories with the more common experience of market downturns, weak exits, and underwhelming stock performance—and stresses the need for a real exercise/sale plan.
(01:50–02:25) – Benchmarking beyond averages. He notes that industry averages don’t capture the full picture; role, company trajectory, and equity structure all matter.
(02:25–end) – Career moves as planning opportunities. Dan closes by pointing out that lower-income transition periods are big tax-planning windows (e.g., Roth conversions) and invites sales leaders and GTM executives to connect with Tailored Wealth to maximize their compensation strategy.

Episode Summary

In this short, targeted video, Dan speaks directly to go-to-market leaders and sales professionals whose pay is heavily driven by bonuses, commissions, and equity. He starts by asking the question most people overlook: not how much you’re going to make with stock options and variable comp, but how much you’ll actually keep after taxes and timing. Having sat in the seat as a former Chief Revenue Officer and sales leader, he understands both the upside and complexity of modern compensation structures.

Dan begins with bonuses and commissions, explaining that these are treated as supplemental wages and often withheld at a flat 22%. For high earners, that can be well below their true marginal tax rate—sometimes 37% or more. The result is under-withholding and expensive tax surprises if you’re not planning ahead. One practical lever he highlights is timing: when possible, negotiating the payment of a large bonus into a lower-income year can lower your tax bill without changing the bonus amount itself.

He then turns to equity compensation, noting that while the headlines celebrate massive wins, many professionals experience the flip side—market downturns, disappointing exits, and stock that doesn’t live up to its initial promise. That’s why he stresses having a clear plan for when to exercise options, when to sell, and how to reinvest proceeds, rather than simply hoping for the best. Dan also points out that benchmarking comp by industry averages alone is insufficient; the true value of a package depends on your role, your company’s trajectory, and the specific equity structure.

Finally, he frames career transitions as powerful—but often ignored—tax planning windows. Lower-income periods between roles can be ideal times to execute Roth conversions and other strategic shifts, paying taxes at a lower rate today to build more tax-free growth later. Throughout, his message is clear: your compensation package is complex, but with intentional planning it can become one of your greatest wealth-building tools. He closes by inviting sales leaders and go-to-market executives to connect via yourtailoredwealth.com to ensure they’re actually maximizing what they earn.

Full Transcript

Dan: Bonuses, variable comp, equity packages that sound great but don’t always deliver. If you’re a go-to-market leader or sales professional, you know that managing your compensation package strategically is just as important as earning it. But most people don’t have a plan for it, and that’s where they miss major wealth opportunities.

Dan: I’m Dan Pascone, founder and CEO of Tailored Wealth, and I’ve been in your shoes. As a former Chief Revenue Officer and sales leader myself, I know firsthand the complexities that come with bonuses, variable compensation, equity, and career transitions, and I’ve seen how the right financial strategy can help go-to-market leaders turn their income into real, lasting wealth.

Dan: Let’s start with bonuses and commissions. Most people don’t realize that bonuses are classified as supplemental wages, so they’re taxed differently than your salary. Most companies withhold a flat 22%, but if you’re in a higher tax bracket, your actual rate could be more like 37% or even higher. That means you could be under-withholding, leading to a surprise tax bill if you don’t plan ahead.

Dan: Here’s a smarter approach: if you’re expecting a big bonus, consider timing. If you’re able to negotiate the timing of a bonus to come in a lower-income year, it could save you thousands.

Dan: Equity comp is another huge factor. We’ve all heard the success stories, but the reality often includes market downturns, bad exits, and underwhelming stock performance that have left many professionals with far less than they had originally expected. That’s why you need a clear strategy for when to exercise, sell, and reinvest.

Dan: Then there’s benchmarking your comp. Industry averages are great, but do they tell the full story? Your role, your company’s trajectory, and the type of equity package all determine what your comp is actually worth.

Dan: And if you’re considering a career move, you need to think beyond salary. You should also consider lower-income transition periods as big tax planning opportunities—to make moves like Roth conversions, where you pay the taxes now but can experience tax-free growth down the road.

Dan: Bottom line, your compensation package is complex, but with the right planning, it can be one of your greatest wealth-building tools. So if you’re a sales leader or go-to-market executive and want to make sure you’re maximizing your compensation package the right way, hit that like button, subscribe, and check out yourtailoredwealth.com for more.

Resources & Concepts Mentioned

Supplemental wage taxation: How bonuses and commissions are withheld differently from base salary.
Equity compensation strategy: Planning when to exercise, sell, and reinvest stock options and other equity.
Compensation benchmarking: Comparing your full package (cash + equity) to role-, stage-, and industry-specific norms.
Roth conversions: Converting pre-tax retirement assets to Roth in lower-income years to build tax-free future income.
Career transitions as planning windows: Using lower-income periods between roles for proactive tax and wealth planning.

FAQs

Why are my bonuses taxed so differently from my regular salary?

Bonuses and commissions are generally treated as supplemental wages, so employers often withhold at a flat rate (commonly around 22%). If your true marginal tax bracket is higher, this can leave you under-withheld, resulting in a bigger tax bill at filing time unless you plan and adjust.

How should I think about the value of my equity package?

Don’t just focus on the headline number. Consider your company’s trajectory, vesting schedule, liquidity risk, and concentration risk. You also need a plan for when to exercise, when to sell, and how to reinvest. The right strategy can help you translate paper value into real, after-tax wealth.

What’s a smart way to plan around a big bonus year?

If possible, discuss timing with your employer—sometimes moving a bonus into a lower-income year can reduce the tax hit. You may also want to adjust withholding, set aside cash for taxes, and coordinate with other events like option exercises or asset sales so you’re not stacking multiple big tax items in the same year.

How can a career transition help my long-term tax plan?

Lower-income transition years can be ideal for Roth conversions and other strategic tax moves. Converting pre-tax dollars at a lower marginal rate lets you pay less tax now in exchange for more tax-free growth and withdrawals later, which can be a major long-term advantage if done thoughtfully.

Do I need a specialist to help with my equity and variable comp?

It’s often wise to work with an advisor who understands executive and sales compensation, stock options, and tax planning. The complexity and stakes are high, and a well-designed strategy can easily justify the cost by helping you avoid big mistakes and capture opportunities you might otherwise miss.

Disclaimer

This video and written summary are for educational and informational purposes only and do not constitute financial, tax, or legal advice. They do not create a client relationship with Tailored Wealth or any related entity.

Equity compensation, bonuses, and tax strategies involve risks and trade-offs that depend on your specific circumstances. Before making any decisions, you should consult with:

A licensed financial advisor or planner
A qualified tax professional (CPA or EA)
Legal counsel, where appropriate

Any examples mentioned are illustrative only and not guarantees of results. Actual outcomes will vary based on your personal situation and future changes in tax law and markets.

Next Steps

List your comp components: Base, bonus, commissions, equity types (ISOs, NSOs, RSUs, etc.).
Review bonus taxation: Check how your employer withholds on bonuses and whether you’re likely under-withheld.
Map your equity: Document vesting schedules, strike prices, and key dates; identify concentration risk.
Plan around transitions: Look ahead to potential lower-income years where Roth conversions and other tax moves could make sense.
Talk to a specialist: Schedule a conversation with an advisor experienced in sales and go-to-market compensation to turn your income into a longer-term wealth strategy.

Your compensation is more than a paycheck—it’s a powerful engine for long-term wealth if you design a strategy around how and when you earn, exercise, sell, and reinvest.