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 — Scott Osborn, advisor to commercial airline pilots across the major carriers.
A practice shaped
by a single profession.
Airline retirement is fundamentally different from retirement in any other profession. You face a mandatory retirement age, complex pension calculations, benefit windows that open and close on specific timelines — and decisions that are often irreversible once made.
Retirement Planning
The 65 cliff, pension lump-sum vs. annuity decisions, benefit windows, sequence-of-returns risk. Where pilots actually need a specialist.
Retirement Account Strategy
From 401(k) MBCPB optimization to Roth vs. Traditional IRA decisions and non-401(k) account management, we build a tax-efficient account structure designed around pilot income patterns and mandatory retirement timelines.
Tax-Aware Planning
Variable income, premium pay, trip trading, deferred comp. Roth conversion ladders, bracket management, tax-loss harvesting.
Investment Management
Globally diversified portfolios designed for high incomes and the transition to retirement income — cash flow, not just total return.
Career-Stage Planning
First officer accumulation, captain peak earnings, pre-retirement consolidation. The plan changes — your advisor should change with you.
Ongoing Advisory
Contract changes, benefit updates, and life events — marriage, new children, divorce, major purchases — we adjust the plan as your life unfolds. A relationship, not a transaction.
Run the numbers in 30 seconds.
Plug in your W-2, age, and contribution rate. I'll show you a realistic projection — including the 18% airline DC match most pilots forget to model.
- Models 401(k) MBCPB match precisely
- Roth conversion windows visualized
- Pre-65 vs post-65 income paths
What could yours actually look like?
The advisor who built this practice for one profession.
I'm Scott Osborn — engineer by training, Notre Dame MBA, Army officer who came home from a 2011 deployment to Afghanistan and decided to build a financial practice exclusively for pilots. The decision wasn't accidental — it was the byproduct of years serving alongside aviators, watching careers transition from military service to the flight deck.
"Better data. Better decisions. Better results."
The Wealthy Pilot's Podcast: When to Stop Maxing the 401(k)
With an 18% DC match on the table, every dollar after the limit gets complicated. Where the math actually crosses over — and what to do about it.
The Dichotomy of Wealth
Scott's plain-English playbook for pilot retirement timing, pension elections, and the 65 cliff.
Get a free copyThe Wealthy Pilot Toolkit
Annual checklists, withholding worksheets, and benefit-window calendars for every major carrier.
Download toolkitYou 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.