The Wealthy Pilot's Podcast: Financial Flight Controls for Today's Commercial Airline Pilots

In part two of this special Masters series, Scott takes us to the “back nine”- the final stretch of retirement planning where pressure builds and smart decisions matter most. From avoiding risky plays in your 50s and 60s to understanding how emotions can derail your strategy, Scott lays out what it really means to finish strong.

Here’s some of what we discuss in this episode:

⛳ Why “Amen Corner” = age 50+ in your financial life

🎯 Avo...

The Masters is a beautiful reminder of just how much strategy, patience, and long-term focus goes into a great round of golf. Turns out, retirement works a lot like the game. Today, we’re teeing up a few key lessons from the course and how they translate into smarter planning for your financial future.

Here’s some of what we discuss in this episode:

⛳ What golf teaches us about investing

⚠️ Avoiding overconfidence after short-term win...

Plenty of people have concerns about stock market volatility, a potential recession on the horizon, and fears for the economy amidst federal layoffs and tariffs. What if you’ve had 2025 marked on the calendar for a while as the year you plan to retire? Is this a bad time to do it?

Here’s some of what we discuss in this episode:

0:00 – Intro

2:08 – Headline response to market

3:49 – Sequence of returns risk

6:19 – Different market sector...

What if you could become your own banker and take control of the way you finance your life? Today we’re excited to welcome on Brian Moody and Hans Tooey of Remnant Finance to explore the Infinite Banking Concept- a financial strategy designed to help you protect, save, and grow your wealth without relying on traditional banks.

Here’s some of what we discuss in this episode:

0:00 – Intro

1:00 – Background on our guests

4:50 – The Infini...

Thinking about starting a side gig? Many pilots explore side hustles like real estate or passion projects, but how do these extra income streams impact retirement planning? Are there tax advantages you should be taking advantage of? And how can you ensure your side hustle is working for you, not creating extra stress?

In this episode, Scott breaks down the impact of side gigs on your long-term financial plan. We’ll discuss the most ...

If you’ve spent years successfully managing your own investments, do you really need a financial advisor? Scott works with a lot of highly skilled, intelligent professionals. So, for someone like this, is working with an advisor just an extra expense, or could it actually add real value?

In this episode, we break down when and why even experienced investors might benefit from professional guidance and when they’re probably fine on t...

The day President Trump took office, he announced plans to implement a 25 percent tariff on goods from Mexico and Canada. Additional tariff conversations have exploded since that day. How might this impact your personal finances and the economy?

In this episode, we’ll take a closer look at the backstory of tariffs- what they are, why governments impose them, and the historical context of them. We’ll also break down the new tariffs t...

Valentine’s season is all about love, but let’s be honest, money plays a huge role in any relationship. Whether you’ve been together for decades or are just starting out, financial stress can put a strain on even the strongest partnerships. So, how do you talk about money without killing the romance?

In today’s episode, we’re looking at the questions every couple should ask about finances and retirement. 

Here’s some of what we discu...

Whether it's for a home remodel, a major purchase, or just to cover unexpected expenses, where should you turn for cash when you need it? In today’s episode, Scott breaks down the three primary avenues for obtaining cash: 401(k) loans, Home Equity Lines of Credit (HELOCs), and personal loans. 

We’ll explore the pros and cons of each option and what pilots should keep in mind before borrowing. As always, be sure to consult a qua...

Should you own airline stock? With the airline industry experiencing a rollercoaster of performance this past year alone, it’s an interesting question to discuss. In this week’s episode, Scott and Marc explore the complexities of investing in airline stocks and how emotional biases can influence investment decisions. 

Here’s some of what we discuss in this episode:

0:00 – Intro

2:24 – Company bias and emotional investing

6:47...

Delta’s record-breaking $1.4 billion profit-sharing payout for 2024 has employees buzzing, with many set to receive an average of five weeks’ pay as their share. If you’re a pilot benefiting from this bonus, what’s the best way to put it to good use?

Join Scott and Marc as they explore how to strike the right balance between celebration and strategic financial planning. From bolstering emergency funds to maxing out 401(k) contributi...

In this episode, Scott and Marc chat about a recent lawsuit filed by an American Airlines pilot, which challenged the integration of ESG criteria into the company’s 401k plans. This opens up a wider discussion about the importance of transparency and fiduciary responsibility in retirement planning.

Listen in as Scott explains the difference between fiduciary and suitability standards and why understanding this could help you make mo...

We’ve all heard about the importance of contributing to a 401(k) for retirement. But is it really enough on its own? For some, maybe it is, but it’s always wise to explore other options and keep an open mind.

In this episode, Scott dives into a range of strategies that could help you build wealth for retirement, from Roth IRAs and the "backdoor" Roth to life insurance, real estate investments, and tax loss harvesting. 

Here...

In this episode of the Wealthy Pilots Podcast, Scott Osborn breaks down where to contribute your money in 2025. Learn why diversifying your savings across Roth, tax-deferred, and taxable accounts can help you retire with more flexibility and fewer tax headaches. Discover simple tweaks that can make a big difference for your future—whether you’re just starting or already maxing out your 401(k).

Here’s what you’ll learn on t...

In this episode of The Wealthy Pilot's Podcast, we discuss recent developments in market-based cash balance plans within the airline industry, focusing on United Airlines pilots’ rejection of their proposed 2024 contract. Scott and Marc break down how these unique retirement plans work and why pilots are concerned about their long-term financial benefits.

They also explore the trade-offs between opting into market-based cash ba...

In this episode of The Wealthy Pilot's Podcast, Scott and Marc break down the latest Federal Reserve rate cuts and explore what they mean for the economy, businesses, and financial planning. With interest rates on the decline, they discuss how this could impact mortgage affordability in 2025 and why large companies are likely to make more aggressive investments. They also dive into the potential opportunities these rate cuts p...

As the year draws to a close, it's the perfect time to take a step back and review your financial planning. In this episode, Scott discusses important year-end strategies to help you optimize your finances before December 31. He covers key topics like Roth conversions, tax loss harvesting, HSA contributions, and other essential tasks that could make a big impact on your financial situation.

Plus, Scott offers a look ahead to 20...

In this episode of The Wealthy Pilots Podcast, Marc and Scott dive into the current state of the airline industry and chat about both the challenges and successes some airlines are facing. From record travel numbers to struggling airlines like JetBlue and Spirit, they discuss how rising fuel costs and labor issues are affecting profitability. 

With larger airlines doing well, smaller regional carriers are left to fight for...

In Scott’s line of work, it’s common to see pilots who are juggling a side hustle or business. That’s why this week, we’re diving into the Beneficial Ownership Information Report (BOIR), part of the Corporate Transparency Act (CTA). What is it, why does it matter, and how does it impact pilots and their side hustles?

Join us as Scott breaks down the penalties for non-compliance and what you need to do to ensure you’re squa...