My First Million
The best business ideas come from noticing what's working and doing it better, faster, or for a different audience.
Risk Perception Changes with Experience
Experienced entrepreneurs perceive less risk in activities they've done repeatedly, while others see the same activities as highly risky
Decision Rule
When evaluating 'risky' opportunities, ask whether your risk assessment is based on inexperience or genuine danger
How It Works
Repeated exposure to business acquisition, deal-making, or specific industries creates pattern recognition that reduces perceived uncertainty
Failure Modes
Overconfidence from past success in different contexts
Dismissing legitimate new risks due to familiarity bias
Assuming others share your risk tolerance
Example Decision
“Experienced acquirer sees buying 10 magazines for $5M as low-risk because they know the value unlock playbook, while first-time buyer sees it as extremely risky”
Related Knowledge
Patient capital enables better business building than venture timelines
Entrepreneurs should seek capital sources aligned with their business development timeline rather than accepting standar
Negative Customer Acquisition Cost Model
A business model where customers pay you to become customers, then you sell them higher-value products or services
Content-Informed Commerce Strategy
Using content engagement data to identify and validate high-value commercial opportunities before building them
Acquire and consolidate dying magazines into profitable commerce-driven media business
Portfolio of 20+ magazines generating $50M+ revenue with 18%+ EBITDA margins by selling high-value products to engaged a
people pay for the magazine and so that is how he acquires a customer
Customers pay to become customers, creating negative acquisition costs
let content inform the commercial decisions that we made
Use content engagement data to validate commercial opportunities before building them