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Darren Pleasance's aviation journey began serendipitously at age 13 in Livermore, California, sparked by witnessing model airplane flying in a local park (02:32)
Boy Scouts aviation merit badge provided first airplane flight experience with troop leader who was also a flight instructor
Airport proximity advantage allowed daily after-school bicycle rides to Livermore Airport for hands-on learning
Mentorship network development through open hangar visits led to free flight instruction from CFI named Doug
Accelerated certification timeline: solo at 16, private at 17, commercial instrument flight instructor at 18
College funding strategy utilized flight instruction income to pay for education expenses
Life decision framework established early: "When faced with difficult decision, choose one that makes for better story" (07:03)
McKinsey departure decision after 14 years applied this principle to join Google despite financial spreadsheet analysis
Alaska bush pilot choice over completing engineering master's degree exemplified same philosophy
Career diversification approach created multiple aviation experiences: corporate jets, glider towing, competition aerobatics, bush flying
Color vision deficiency discovery at age 16 during first medical examination created major career obstacle (09:16)
Initial medical restriction: "not valid for night flight or color signals" threatened professional pilot aspirations
Demonstrated ability waiver process required FAA flight examination demonstrating ability to distinguish aviation-relevant colors
Testing requirements included: identifying plowed vs. unplowed fields, recognizing taxiway centerline lights, runway edge lights, beacon colors
Airline career impact: even with eventual first-class medical clearance, airlines wouldn't hire pilots with any medical history complications
Blessing in disguise outcome: forced exploration of diverse aviation opportunities including John Travolta corporate pilot work, competition aerobatics, P-51 flying
McKinsey consulting foundation provided comprehensive business function exposure across marketing, sales, finance, organizational strategy (05:58)
High-tech specialization and sales/marketing focus opened door to Google global team leadership opportunity
14-year tenure built expertise in helping management teams improve business performance worldwide
Diverse client experience across multiple industries and business functions created versatile skill set
Google and Cisco leadership roles combined with continuous aviation involvement maintained dual expertise (12:51)
Weekend flying commitment included teaching aerobatics at Bedford Airport's Executive Flyers Aviation
Competition aerobatics involvement led to EAA board connections and industry networking
P-51 flying experience enhanced aviation credibility and public profile
Unique qualification combination merged deep aviation passion with Fortune 500 business leadership experience (12:51)
200+ employee organization requires substantial business management capabilities
Public speaking requirements for member events, donor relations, political advocacy, airport community relations
Aviation credibility essential for representing pilot community interests and understanding operational challenges
Advocacy experience needed for communicating aviation value to non-pilot stakeholders
Current aircraft ownership maintains grassroots GA connection through Sea Ray amphibious aircraft and RV-6 ownership (15:11)
Recent flying examples: Priest Lake, Idaho seaplane fly-in participation, formation flying with friends
Backcountry flying engagement demonstrates continued hands-on small aircraft experience
Cost-conscious operations understanding through Rotax-powered aircraft ownership
Base membership value proposition at $89 annually provides extensive pilot support services (20:40)