Pitching Investors at 10,000 Feet—Lessons From a Day in the Sky

Pitching Investors at 10,000 Feet—Lessons From a Day in the Sky

Lesson: Investor Decks Are a Lot Like Air-Traffic Control

I spent ten straight hours with BoomPop CEO Healey Cypher working on his fundraising strategy—then capped the day by flying a small plane over the Golden Gate Bridge. Turns out pitching and piloting share the same core requirements:

1. Clear Destination – Investors (and passengers) want to know exactly where you’re headed.
   
   
2. Defensible Flight Path – When someone questions your route, you need crisp, data-driven answers.
   
   
3. Zero Surprises Mid-Flight – Nobody enjoys turbulence at 10,000 feet or slide 10. Over-prepare so your journey feels smooth.
   
   

Bonus lesson: turbulence is inevitable. How you handle it earns trust and confidence.

Insight: Map, Communicate, Reassure

• Map the Route: Your deck should outline the journey from runway to runway—problem, solution, market, revenue, and exit.
  
  
• Communicate Early & Often: Keep stakeholders in the loop; silence equals uncertainty.
  
  
• Reassure With Contingencies: A solid “what if” plan calms nerves when the unexpected hits.
  
  

Pilots call it cockpit resource management; founders call it proactive investor relations. Different jargon, same principle: safety—and confidence—come from preparation.

Action Item: Conduct a “Pre-Flight Check” on Your Deck

1. Destination Slide – Is your vision unmistakably clear in the first 90 seconds?
   
   
2. Flight Path Slide – Can you defend every metric and milestone?
   
   
3. Turbulence Slide – Do you address risks head-on and show contingency plans?
   
   

Run through these checks before your next pitch, and watch investor anxiety (and questions) fade.