Skip to content
About · Scott Osborn

From the cockpit of an MRAP
to the flight deck of your finances.

I'm Scott. I help airline pilots make better financial decisions — not because it's a profitable niche, but because I spent a decade in uniform alongside future captains and watched too many sharp operators land at retirement without a plan.

Scott Osborn
The credentials
Notre Dame
MBA, Finance
U.S. Army
Officer · Combat veteran
Bronze Star
Awarded 2011, Afghanistan
CIB
Combat Infantryman's Badge
Series 65
Investment Adviser Rep.
Fiduciary
Always. By law and by oath.
Why pilots, why this

The story, the short version.

In Afghanistan, I watched a captain three weeks from her terminal leave realize she'd never opened her TSP. She wasn't lazy. She wasn't dumb. She was just busy keeping people alive, and nobody had ever sat her down for the conversation. That's the story I keep coming back to.

I came home, finished my MBA at Notre Dame, and went into wealth management. The big firms wanted me to be a generalist with revenue targets. I wanted to be a specialist for one specific kind of client — high-earning, time-poor, with a benefits package nobody outside their cockpit understood.

In 2018 I founded an independent practice for pilots. Today I work with 411 pilot households across Delta, United, American, Southwest, FedEx, and UPS. I am independent. I am a fiduciary. I am not affiliated with any airline. And I will tell you the truth even when it costs me the engagement — that's the only version of this practice worth running.

Timeline

How I got here.

2003
Notre Dame, B.S. Mechanical Engineering
2007
Commissioned, U.S. Army Officer
2011
Bronze Star · Combat Infantryman's Badge — Afghanistan
2014
Notre Dame Mendoza, MBA — Finance
2018
Founded an independent practice — by pilots, for pilots
2024
Launched The Wealthy Pilot's Podcast
It Starts with a Conversation

You don't need to have everything figured out.

A simple conversation is often the first step toward clarity — no pressure, no sales pitch, just an honest look at whether my approach fits your situation.