135 - Our Biggest Investing Mistakes of 2025 And How They Sparked Process Upgrades

This episode is our yearly investing accountability report — the “Whoopsie Daisies” review where we openly break down the trades and decisions that didn’t go to plan.

We cover:

• Dividend suspensions and cuts that blindsided us (and what we do now when income goes to zero).
• Selling too early on winners and how we’re changing our  profit-taking rule so we stop prematurely ejecting from huge runners. (Last year's keep going up! WTF) 
• High-yield ETF experiments that didn’t  behave the way they should (and which YieldMax ETFs aren't absolute garbage). 
• Overpaying for great long-term holdings (UPS, LYB, TRMD) and how we use valuation, bands, and DCA to repair a bad entry without panic-selling.
• How we manage risk with a max position-size rule and why that one rule prevents a single holding from turning into a portfolio hostage situation.

This is our real process for how we navigate investing to reduce risk and keep compounding even when the market humbles us. 

***NOTE***

We did live streams on Thursday 12/18/2025 (today) and Friday 12/19/2025 on Our YouTube Channel to show where we allocated our $150,000 in condo sale proceeds.

Watch the replays below.

Thursday 12/18 Livestream --> watch here

Friday 12/19 Livestream --> watch here

Questions? Email Tim at [e-mail]

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**DISCLAIMER**
Ticker metrics change as markets and companies change, so always do your own research. The content in this podcast is based on personal experience and is for educational purposes, not financial advice. See full disclaimer here.

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