Avoid the Million Dollar Mistake with your Stock Options

The right decision could save you millions. Learn how to protect and grow your wealth with strategic planning.

What is the Million Dollar Mistake?

The Million Dollar Mistake is a common pitfall for people with concentrated stock positions, one of the most common being Incentive Stock Options (ISOs).

At KB Financial Advisors, we’ve seen it firsthand: a $5 million opportunity can quickly shrink to under $500,000 if the right decisions aren’t made. Let’s break it down with two real-world examples.

1
Exercise ISOs
2
Decide to Hold or Sell
3
Financial Outcome

A Tale of Two Decisions
(Client 1 vs. Client 2)

Meet Client 1 and Client 2. Both started with the same stock options, stock price, and potential value. What set them apart? Their decisions. Over three years, Client 1’s portfolio shrank by 92%, while Client 2’s diversified investments grew steadily.
The Million Dollar Mistake: The High Cost of Mishandling Your Stock Option Wealth
Total value ($M)
Client 1
Client 2
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4
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3
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2
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1
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0
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Year 1
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Year 2
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Year 3
Time (Months)

Here’s how their stories unfolded

March, Year 1:

Both clients exercise 50,000 shares at $1/share with a stock price of $35/share. Total value: $1.75 million.

September, Year 1: Stock peaks at $100/share

  • Client 1 holds, hoping for higher prices and want to avoid paying higher taxes. They do not have a target price identified.
  • Client 2 sells, paying $1.8 million in taxes but securing $3.12 million net. They have a target price identified.

March, Year 2: Stock falls to $40/share

  • Client 1 is forced to sell shares to pay a $476k AMT tax bill.
  • Client 2 reinvests into a diversified portfolio.

December, Year 3: Stock price drops to $10/share

  • Client 1’s portfolio is now worth just $381k.
  • Client 2’s diversified investments have grown to $3.2 million.

The Result

Client 1
$1.75M
$381K
Client 2
$1.75M
$3.2M

The financial impact in numbers

When you compare Client 1 and Client 2, the numbers speak for themselves. By focusing on price rather than taxes, Client 2 preserved their wealth and avoided the Million Dollar Mistake.

Metric
Initial Stock Value
AMT Exposure
Tax Paid
New After Taxes (Year 1)
Final Value (Year 3)
Client 1 (Hold)
$1.75M
$476k
$0
$1.5M
$381k
Client 1 (Sell & Diversify)
$1.75M
$476k
$1.83M
$3.12M
$3.2M

The Lesson?

It’s tempting to hold stock to avoid paying taxes, but this often leads to bigger losses. Client 1 tried to avoid a $1.8 million tax bill-and ended up losing over $4 million in stock value. Client 2 understood that taxes are a cost of securing wealth and made a strategic decision to sell and diversify.

Selling at the right time ensures you protect your wealth, even if it means paying taxes now. Diversification adds a layer of safety, guarding against single-stock declines.

How We Help You Avoid the Million Dollar Mistake

At KB Financial Advisors, we specialize in helping clients with stock options make smarter decisions.

Strategic sell/hold analysis
Tax impact assessment and planning
Diversified investment strategies for long-term growth

Make your investments work as hard as you do with KB Financial Advisors

Book your introductory call to see how we can help.