Invest In Unregretted Expenses

A strategy for investing in companies whose products you heavily use and value, based on analyzing your profit & loss statement expenses.

Core Concept

• Look at expenses in your P&L that are:
  • Meaningful line items you notice
  • Expenses you don't regret
  • Worth more than what they cost
• These represent opportunities to invest in companies you already validate through usage

Investment Approach

• Identify products you're an early/power user of
• Look for companies where you deeply understand the product
• Consider companies where you can add value beyond capital
• Approach companies as a potential partner/investor
• Be willing to take equity instead of just being a customer

Real World Example (Shepherd)

• Started as a heavy user of overseas talent recruitment
• Recognized it as significant unregretted expense
• Approached company about partnership opportunity
• Leveraged audience and influence as value-add
• Resulted in significant value growth (3x in one year)

Keys to Success

• Must genuinely understand and use the product
• Should have ability to help grow the business
• Need to bring more than just capital to the table
• Look for products with strong unit economics
• Focus on businesses with clear value proposition

Benefits

• Lower risk due to deep product understanding
• Natural alignment between investor and company
• Ability to validate product-market fit firsthand
• Can leverage existing experience with product
• Potential to influence product direction and growth

Common Mistake to Avoid

• Not investing in tools/products you heavily use
• Missing opportunity to convert expenses into equity
• Focusing only on new opportunities vs. existing relationships
• Overlooking the value of being a power user