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

What It Covers

Kyle Grieve shares his complete investing framework that generated 18.7% annualized returns since 2020, covering his evolution from cryptocurrency speculation losses to disciplined value investing through quality businesses and microcap inflection points.

Key Questions Answered

• •Portfolio Structure: Divide holdings into two buckets: quality businesses (63% of portfolio) requiring 15%+ ROIC and competitive moats for long-term compounding, and microcap inflection points (37%) showing two consecutive quarters of 25%+ revenue and earnings growth for faster gains.
• •Position Sizing Strategy: Start quality positions at 2-3% cost basis, allowing growth to 10% maximum, while microcap positions begin at 1% and cap at 5-6%. Never trim winners regardless of absolute portfolio weight, as top performers often reach 20-28% through appreciation without intervention.
• •Three-Part Sell Discipline: Exit positions only when finding better risk-reward opportunities, when price pulls forward five to ten years of expected returns, or when investment thesis breaks. Ignore sunk costs and focus solely on forward-looking fundamentals rather than purchase price when evaluating holds.
• •Management Evaluation Framework: Assess executives across twelve criteria including insider ownership percentage relative to net worth, capital allocation discipline, transparency consistency during downturns, and compensation structure. Management integrity ranks as non-negotiable requirement, warranting immediate exit if any cracks appear in trustworthiness.
• •Performance Measurement Method: Track owner earnings (operating cash flow minus maintenance capex) growth rather than stock price movements to evaluate investment success. Require 15%+ annual owner earnings growth for quality holdings and 25%+ for microcaps, checking quarterly against probability-weighted scenarios using Bayesian updating.