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  1. We Study Billionaires - The Investor’s Podcast Network
  2. TIP755: My Process for Finding Great Investments w/ Kyle Grieve
TIP755: My Process for Finding Great Investments w/ Kyle Grieve

TIP755: My Process for Finding Great Investments w/ Kyle Grieve

We Study Billionaires - The Investor’s Podcast Network · Sep 21, 2025

An investor's philosophy: doubling capital every 5 years by focusing on quality compounders, micro-cap inflections, and behavioral discipline.

Exploit Market Under-Reaction to Acquisitions by Serial Acquirers

A specific arbitrage opportunity exists with serial acquirers. When they announce a deal that will significantly increase future earnings per share, the market often under-reacts. An investor can buy shares at a compressed forward multiple before the full impact of the acquisition is priced in.

TIP755: My Process for Finding Great Investments w/ Kyle Grieve thumbnail

TIP755: My Process for Finding Great Investments w/ Kyle Grieve

We Study Billionaires - The Investor’s Podcast Network·5 months ago

Design Your Environment to Foster Inaction for Better Investment Returns

Most investing environments encourage constant, often harmful, action. The speaker actively engineers an environment for inaction by eliminating visual stimuli like financial TV and filtering social media noise. This counteracts behavioral biases and promotes the patience required for long-term compounding.

TIP755: My Process for Finding Great Investments w/ Kyle Grieve thumbnail

TIP755: My Process for Finding Great Investments w/ Kyle Grieve

We Study Billionaires - The Investor’s Podcast Network·5 months ago

Adopt a 'Business Owner' Mindset to Hold Compounders Through Volatility

To avoid panic selling, the speaker imagines the management of his portfolio companies as close personal associates. This mental model fosters trust and patience, allowing him to hold onto strong compounders through inevitable headwinds, just as one would when backing a friend's business.

TIP755: My Process for Finding Great Investments w/ Kyle Grieve thumbnail

TIP755: My Process for Finding Great Investments w/ Kyle Grieve

We Study Billionaires - The Investor’s Podcast Network·5 months ago

Aiming to Double Capital Every Five Years Forces a Focus on True Multi-Baggers

Instead of focusing on relative performance against an index, the speaker sets an absolute goal of doubling capital every five years. This forces a highly selective process, screening for businesses with the potential to be 10x, 50x, or 100x winners, and treats benchmarks merely as an indicator of opportunity cost.

TIP755: My Process for Finding Great Investments w/ Kyle Grieve thumbnail

TIP755: My Process for Finding Great Investments w/ Kyle Grieve

We Study Billionaires - The Investor’s Podcast Network·5 months ago

Average Up on Winners, Don't Just Average Down on Losers

Challenging traditional value investing dogma, the speaker advocates for averaging up—buying more of a stock as its price rises. This strategy treats price appreciation as confirmation of a correct thesis, allowing an investor to build a larger position in their best-performing ideas rather than just adding to laggards.

TIP755: My Process for Finding Great Investments w/ Kyle Grieve thumbnail

TIP755: My Process for Finding Great Investments w/ Kyle Grieve

We Study Billionaires - The Investor’s Podcast Network·5 months ago

Split Your Portfolio Into 'Quality' and 'Micro-Cap Inflection' Buckets

The speaker divides his portfolio into two distinct categories: stable, long-term "Quality Businesses" and high-growth "Micro-cap Inflection Point" businesses. Each bucket has its own specific criteria, allowing for a balanced approach between reliable compounding and high-upside opportunities.

TIP755: My Process for Finding Great Investments w/ Kyle Grieve thumbnail

TIP755: My Process for Finding Great Investments w/ Kyle Grieve

We Study Billionaires - The Investor’s Podcast Network·5 months ago

A 97% Crypto Loss Provided a Better Investing Foundation Than Stock Market Wins

The speaker's catastrophic early foray into leveraged crypto speculation, resulting in a 97% loss, provided the foundational lessons for his successful value investing approach in stocks. This failure taught him to avoid technical indicators, leverage, and shorting, and to only buy assets he understands.

TIP755: My Process for Finding Great Investments w/ Kyle Grieve thumbnail

TIP755: My Process for Finding Great Investments w/ Kyle Grieve

We Study Billionaires - The Investor’s Podcast Network·5 months ago

Your Biggest Mistakes Are Often the Winning Stocks You Failed to Buy

Beyond analyzing losing positions (errors of commission), the speaker emphasizes studying mistakes of omission—high-quality businesses he understood but failed to invest in. This reflective practice helps identify flaws in process, time management, or conviction, which can be more instructive for future success than reviewing simple losses.

TIP755: My Process for Finding Great Investments w/ Kyle Grieve thumbnail

TIP755: My Process for Finding Great Investments w/ Kyle Grieve

We Study Billionaires - The Investor’s Podcast Network·5 months ago

Measure Success by a Company's Operating Results, Not Its Stock Price

Following Warren Buffett, the speaker measures investment success by tracking a company's "owner's earnings" (cash from operations minus maintenance capex), not its stock price. If operating results are growing as expected, short-term price drops become irrelevant, preventing emotional decisions and reinforcing a long-term, business-focused perspective.

TIP755: My Process for Finding Great Investments w/ Kyle Grieve thumbnail

TIP755: My Process for Finding Great Investments w/ Kyle Grieve

We Study Billionaires - The Investor’s Podcast Network·5 months ago