/
© 2026 RiffOn. All rights reserved.
  1. We Study Billionaires - The Investor’s Podcast Network
  2. TIP778: How My Thinking About Investing Evolved in 2025 w/ Kyle Grieve
TIP778: How My Thinking About Investing Evolved in 2025 w/ Kyle Grieve

TIP778: How My Thinking About Investing Evolved in 2025 w/ Kyle Grieve

We Study Billionaires - The Investor’s Podcast Network · Dec 26, 2025

Host Kyle Grieve shares his 9 biggest investing lessons from 2025, focusing on flexible conviction, company DNA, and combating psychological bias.

The Mark of a Legendary Founder Is Building a Company DNA That Makes Them Non-Essential

Great companies survive not because of a founder's continued presence, but because the founder codified a culture and operational DNA that outlives them. Companies like Home Depot and Amazon continue to thrive because their core principles are deeply embedded and replicable.

TIP778: How My Thinking About Investing Evolved in 2025 w/ Kyle Grieve thumbnail

TIP778: How My Thinking About Investing Evolved in 2025 w/ Kyle Grieve

We Study Billionaires - The Investor’s Podcast Network·2 months ago

A Company's Culture is the Upstream Predictor of its Long-Term Financial Performance

Financial results are a downstream outcome. The true upstream driver is a company's culture—its talent density, hiring practices, and incentive systems. A strong culture creates a reinforcing feedback loop that attracts talent, improves decisions, and fuels compounding for decades.

TIP778: How My Thinking About Investing Evolved in 2025 w/ Kyle Grieve thumbnail

TIP778: How My Thinking About Investing Evolved in 2025 w/ Kyle Grieve

We Study Billionaires - The Investor’s Podcast Network·2 months ago

View Portfolio Inactivity as an Engineering Choice, Not Laziness, to Protect Compounding

Compounding is a fragile process. Every portfolio adjustment, like trimming or panic selling, is like opening a door and letting heat escape. Treating your portfolio as a contained machine that works best when untouched reframes "doing nothing" as a strategic, structural advantage.

TIP778: How My Thinking About Investing Evolved in 2025 w/ Kyle Grieve thumbnail

TIP778: How My Thinking About Investing Evolved in 2025 w/ Kyle Grieve

We Study Billionaires - The Investor’s Podcast Network·2 months ago

A "Sufficient Generalist" Outperforms a "Deep Diver" by Focusing Only on Material Variables

The goal isn't to know everything about an industry, which has diminishing returns and leads to overconfidence. A better edge comes from efficiently understanding the few critical variables that matter most across multiple opportunities, while consciously ignoring immaterial details.

TIP778: How My Thinking About Investing Evolved in 2025 w/ Kyle Grieve thumbnail

TIP778: How My Thinking About Investing Evolved in 2025 w/ Kyle Grieve

We Study Billionaires - The Investor’s Podcast Network·2 months ago

Compounding is Shockingly Fragile and Requires a Focus on Downside Protection

Investors often underestimate how easily years of compounded gains can be erased by a single bad decision, such as using excess leverage or making an emotional choice. Downside protection is not merely a defensive strategy; it's a vital, offensive component for ensuring the compounding engine survives to continue running.

TIP778: How My Thinking About Investing Evolved in 2025 w/ Kyle Grieve thumbnail

TIP778: How My Thinking About Investing Evolved in 2025 w/ Kyle Grieve

We Study Billionaires - The Investor’s Podcast Network·2 months ago

Adopt "Strong Convictions, Weakly Held" to Avoid Stubborn Investing Mistakes

Regularly re-evaluate your investment theses. Stubbornly holding onto an initial belief despite new, contradictory information can lead to significant losses. This framework encourages adaptation by forcing you to re-earn your conviction at regular intervals, preventing belief calcification.

TIP778: How My Thinking About Investing Evolved in 2025 w/ Kyle Grieve thumbnail

TIP778: How My Thinking About Investing Evolved in 2025 w/ Kyle Grieve

We Study Billionaires - The Investor’s Podcast Network·2 months ago

Use a Monthly "Conviction Ranking" Journal to Make More Decisive Investment Moves

Objectively track whether new information strengthens or weakens your belief in each holding on a monthly basis. This simple journaling practice forces a regular review, helping you decide whether to add capital or trim a position based on fundamentals, not share price movement.

TIP778: How My Thinking About Investing Evolved in 2025 w/ Kyle Grieve thumbnail

TIP778: How My Thinking About Investing Evolved in 2025 w/ Kyle Grieve

We Study Billionaires - The Investor’s Podcast Network·2 months ago

Incentives Don't Just Drive Behavior; They Actively Warp Perception to Justify It

As Charlie Munger taught, incentive-caused bias is powerful because it causes people to rationalize actions they might otherwise find unethical. When compensation depends on a certain behavior, the human brain twists reality to justify that behavior, as seen in the Wells Fargo fake accounts scandal.

TIP778: How My Thinking About Investing Evolved in 2025 w/ Kyle Grieve thumbnail

TIP778: How My Thinking About Investing Evolved in 2025 w/ Kyle Grieve

We Study Billionaires - The Investor’s Podcast Network·2 months ago

Unmanaged Emotions Don't Disappear; They Evolve to Become Better at Deceiving You

As you gain experience, your emotional biases don't vanish. Instead, they become more sophisticated, articulate, and adept at hiding within what appears to be rational analysis. This makes them even more dangerous over time, requiring constant vigilance to separate logic from emotion.

TIP778: How My Thinking About Investing Evolved in 2025 w/ Kyle Grieve thumbnail

TIP778: How My Thinking About Investing Evolved in 2025 w/ Kyle Grieve

We Study Billionaires - The Investor’s Podcast Network·2 months ago