5 Selling Rules — Keep Your Portfolio in Check!

Knowing when to sell is the number 1 struggle among investors. We know that because we’ve worked with investors for over a decade. Today, we share 5 Selling Rules to help you take action confidently.

Join us for a FREE live webinar on Thursday, March 20th at 1 PM ET, where Mike will walk you through 5 simple steps to clean up your portfolio with confidence.

You’ll Learn

Set a Minimum & Maximum Number of Holdings
Mike recommends keeping between 20 and 40 stocks to maintain focus and efficiency.

Too few stocks? High concentration risk, no room for mistakes.
Too many stocks? Hard to monitor, possible duplication, lack of impact.

Sell Insignificant Positions
Any stock below 1-2% of your portfolio doesn’t contribute meaningfully to returns.

Small positions create noise and analysis paralysis.
Example: Debated selling CAE and DIS—since they were under 2%, it made no impact.
Key questions to ask:
- Is this stock aligned with my strategy?
- Why did I buy it?
- What’s my investment thesis?
- Do I believe in it enough to bring it back to 2-3%?

Get Rid of Duplicates
Investors don’t need every stock in a sector—choose the best one.

Avoid “Pokémon investing” (trying to catch them all!).
Example: Comparing Intel vs. Broadcom, or Bank of Nova Scotia vs. National Bank.
Stock comparison tools can help analyze performance and financials.

Sell Bad Stocks
Holding onto losers because of emotional attachment is dangerous.

Compare thesis vs. numbers. If the dividend triangle declines, consider selling.
Set a timeframe and metrics to track. Example: How Alimentation Couche-Tard (ATD) maintained its value.
Patience is key: Holding for 5 years is still short-term investing!

Let Go of Good Stocks When Needed
Sometimes, even great stocks need to be sold.

Hold winners for a long time, but be flexible.
Companies evolve over time, and so should your portfolio.
Example: BlackRock (BLK) no longer fits the investment thesis.
Trimming winners helps protect gains and balance the portfolio.

Bonus: Why Stock Price Alone Shouldn’t Dictate Selling Decisions

Selling at a 50% profit could prevent you from earning hundreds of percent.
Selling at a 25% loss could have led to selling everything during COVID.
Example: Microsoft’s (MSFT) dip in 2022—those who sold missed a major return.

Free Webinar: 5 Steps to Clean Your Portfolio – March 20th at 1 pm ET

Many investors feel overwhelmed by messy portfolios, unsure of what to keep or toss. But ignoring it could be costly.

Join us for a FREE live webinar on Thursday, March 20th at 1 PM ET, where Mike will walk you through 5 simple steps to clean up your portfolio with confidence.