My First Million
The best business ideas come from noticing what's working and doing it better, faster, or for a different audience.
Jockey Over Horse Investment Philosophy
Prioritizing the quality and capabilities of the founder/team over the business idea when making investment decisions.
How It Works
Evaluates founder's track record, adaptability, learning speed, and execution capability as the primary investment criteria, treating the business model as secondary since ideas pivot but founders don't.
Components
Assess founder's previous execution track record
Evaluate their ability to learn and adapt quickly
Test their self-awareness about strengths and weaknesses
Review how they've handled previous failures or pivots
Determine if both person AND idea are A+ quality
If either person or idea isn't A+, pass on the opportunity
When to Use
When making early-stage investments, hiring key executives, or choosing business partners where uncertainty is high and adaptability is crucial.
When Not to Use
For mature businesses with proven models, highly regulated industries where compliance matters more than adaptability, or when the business model has massive structural advantages regardless of operator.
Anti-Patterns to Avoid
Example
“Two startups pitch AI customer service tools. Company A has a PhD team with weak communication skills. Company B has a founder who previously built and sold a SaaS company, shows customer obsession, and learns quickly. Despite Company A's superior technology, invest in Company B because the founder will adapt and execute better over time.”