6 days ago

No Handouts, No Excuses | Skyler Logdson

Today we sit down with Skyler Logsdon — a high-performing entrepreneur who went from detailing cars as a teenager to being mentored by the founder of Shazam and building multi-million dollar startups.

Skyler shares his inspiring journey of grit, hustle, and relentless execution. From a blue-collar upbringing and football injuries to launching his first app, crushing it in Silicon Valley, and now building Boomerang — the future of lost & found — this conversation is packed with hard-earned wisdom, startup tactics, and life-changing mindset shifts.

00:00 - Intro: Why Skylar’s story is different
01:30 - Sid's personal story & how it relates to Skylar
03:00 - Skylar’s blue-collar childhood in Ojai, CA
05:00 - Starting businesses as a teen: detailing cars & flipping dirt bikes
07:00 - Football injury that led to unexpected leadership lessons
09:00 - Breaking school records and learning from failure
12:00 - Choosing not to play college football: chasing entrepreneurship
14:00 - How Skylar landed full scholarships from Boeing & KPMG
16:00 - Creating a haircut-tracking app in college
19:00 - Mentorship with Shazam founder Felipe
23:00 - Lessons from Silicon Valley and startup #1
25:00 - What Skylar learned selling to Amazon & Goldman Sachs
27:00 - Founding Tatari: Building a TV ad tech company from scratch
30:00 - Helicopter rides, Nobu dinners & closing massive deals
34:00 - Why humility + consistency opens doors
36:00 - The philosophy behind Boomerang — the future of lost & found
40:00 - Core Medical Event reflection & the power of real community
44:00 - Mentorship, legacy, and why Skylar’s story matters now more than ever

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No Handouts, No Excuses | Skyler Logdson

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