How to Pitch Benchmark

Investment Thesis

I invest at seed and Series A in consumer and marketplaces. I look for product founders who build things people actually love, who obsess over retention not acquisition, and who can articulate a 'hair-on-fire' problem. I back category-defining marketplaces and platforms. I care deeply about defensibility, capital efficiency, and the structural reasons incumbents can't easily replicate the business. I back the outlier — the founder who sees the world differently and has the conviction to bet on that vision.

What They Look For

Typical check size: $1000000M – $50000000M

Red Flags

Things Benchmark investors watch for — avoid these in your pitch.

• Cannot articulate the aha moment in the product
• Retention curve flattens or declines after week 1
• Founder obsessed with growth, dismissive of retention
• Burn multiple with no clear payback period
• No structural moat against a well-funded incumbent
• Burner businesses with no clear path to neutral contribution margin
• Founder who thinks exit is the strategy
• No big vision
• Logic falls apart on second pass

Questions They'll Ask

Prepare answers for these. The AI persona will challenge you on them.

• What's the moment in your product where someone first gets real value?
• Show me your D1, D7, D30 retention. Walk me through the curve.
• What did you learn from your first 100 users that changed the product?
• If I look at your cohort from 6 months ago, are they still active?
• Why won't the leader in this space just build this?
• What's the structural moat that compounds with scale?
• Walk me through the math of a single transaction for you.
• What do you believe that most people do not?

3 AI Personas to Pitch