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
5
4
3
2
1
0
Year 1
Year 2
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.