★ Your Financial Co-Pilot
Financial Planning Built for Pilots
Independent, fiduciary advice designed around airline pay, benefits, and retirement timelines. No generic plans. No sales pressure. Just clear guidance from someone who gets it.
Proudly Serving Pilots From
What I Do
How I Help Pilots
From your first day in the right seat to your last flight as captain — and every financial decision in between.
Retirement Planning
Airline retirement is different. Mandatory age limits, complex pension calculations, and benefit windows that close. I help you navigate the timing and strategy.
Learn More →Investment Management
Your portfolio should reflect how airline pilots earn, save, and retire. I manage investments designed for high incomes, career volatility, and the transition to retirement income.
Learn More →Tax-Aware Planning
Variable income, premium pay, trip trading — your tax picture is complex. I build strategies around Roth conversions, tax-loss harvesting, and bracket management.
Learn More →Career-Stage Planning
A First Officer early in their career needs a different plan than a Captain approaching retirement. I tailor strategies to where you are right now.
Learn More →Ongoing Advisory
I work with pilots over the long term — adjusting strategies as markets shift, benefits update, and life evolves. Clarity, accountability, and a trusted advisor who understands.
Learn More →Start Your 401(k) Analysis
Upload your statements and let me show you where you stand — and where you could be.
Get Your Free AnalysisAbout
Meet Scott Osborn
I'm the founder of Pilot Money Guy and an independent, fiduciary financial advisor who works exclusively with airline pilots.
My mission is simple: help pilots protect what they've built, cut through confusing financial noise, and make confident decisions without sales pressure or product-driven advice.
Growing up in a family where money was often uncertain, I saw firsthand how lack of guidance — not lack of effort — can limit opportunity. That drives everything I do.
Listen & Learn
The Wealthy Pilot's Podcast
Your guide to financial takeoff.
Join me as I break down 401(k)s, IRAs, retirement taxes, long-term care, and everything else pilots need to know about building wealth. Whether you're new to the left seat or counting down to retirement — there's an episode for you.
Browse Episodes →Free Resource
Get The Dichotomy of Wealth
Airline pilots face financial challenges most advisors don't understand — variable income, airline-specific 401(k) rules, forced retirement ages, and more.
- Variable income, premium pay & trip trading strategies
- Airline-specific 401(k), pension & profit-sharing rules
- Early retirement windows & mandatory retirement age planning
It All 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 opportunity to see if my approach fits your situation and goals.