ABOUT US
Scott Osborn is the founder of Retire Airlines and an independent, fiduciary financial advisor who works exclusively with airline pilots. His 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.
Scott’s passion for this work started long before his career. Growing up in a hardworking family where money was often uncertain, he saw firsthand how lack of guidance, not lack of effort, can limit opportunity. That perspective drives his commitment to helping pilots simplify their finances and plan with confidence.
Today, Scott brings deep experience, professional credentials, and a pilot-specific focus to every relationship, delivering objective advice aligned solely with his clients’ best interests.
HOW WE HELP PILOTS
PILOT RETIREMENT PLANNING
PILOT RETIREMENT PLANNING
Airline retirement decisions are different, and the stakes are higher. We help pilots understand how their airline’s retirement benefits actually work, so they can make confident decisions about timing, income, and life after flying.
INVESTMENT MANAGEMENT
INVESTMENT MANAGEMENT
Your investment strategy should reflect how airline pilots earn, save, and retire. We manage portfolios designed for high incomes, career volatility, and the transition from accumulation to retirement income.
TAX-AWARE WEALTH PLANNING
TAX-AWARE WEALTH PLANNING
Airline retirement decisions are different, and the stakes are higher. We help pilots understand how their airline’s retirement benefits actually work, so they can make confident decisions about timing, income, and life after flying.
CAREER-STAGE FINANCIAL PLANNING
CAREER-STAGE FINANCIAL PLANNING
A First Officer early in their career needs a very different plan than a Captain approaching retirement. We tailor financial strategies to where you are in your airline career.
ONGOING FINANCIAL ADVISORY
ONGOING FINANCIAL ADVISORY
We work with pilots over the long term, proactively adjusting strategies as markets change, benefits update, and life evolves. You get clarity, accountability, and a trusted advisor who understands the realities of airline life.
THE WEALTHY PILOT’S PODCAST
your guide to financial takeoff
Join financial advisor Scott Osborn as he guides you on your financial journey, from takeoff to landing and everything in between. Whether you’re a pilot or not, we’ll help you chart a course to a successful financial future.
Learn how to navigate 401(k)s, IRAs, retirement taxes, long-term care needs, and much more. The Wealthy Pilot’s Podcast is your one-stop shop for all your financial questions.
Why Choose Retire Airlines?
Retire Airlines was built exclusively for airline pilots who want clear, confident financial and retirement guidance, without generic advice or sales pressure. We understand the unique pay structures, benefits, and career timelines that come with flying for a living, and we design strategies specifically around those realities.
As independent fiduciaries, our focus is on clarity over complexity and long-term confidence over short-term tactics. We don’t offer one-size-fits-all plans or product-driven recommendations. Instead, we build ongoing advisory relationships that evolve with your career, simplify big decisions, and help you move forward with confidence.
