The Pilot Money Guy Podcast

Scott Osborn
  • 0.0 (0)
  • Investing
  • Weekly

Welcome to The Pilot Money Guy Podcast, where we navigate the skies of financial success with your host, Scott Osborn. Each episode, we soar through the challenges and opportunities unique to pilots, from debunking myths to mastering best practices in financial planning and investing. As demand for pilots reaches new heights, so too does the complexity of their financial landscapes. With Scott's expertise, we tackle common pitfalls and strategic wins that can significantly boost a pilot's financial trajectory. Whether you're an aviation professional or just fascinated by the financial skies pilots navigate, this podcast promises insights that can help anyone plot a course toward financial independence. https://pilotmoneyguy.com/ 

  1. 5d ago

    Pilots: Get Your Estate Plan Done This Year!

    📱 Get your customized planning started by booking a call: http://callosborn.com/  ✈️ Order your no-cost Pilot Money Toolkit today: https://pilotmoneyguy.com/toolkit/ Open enrollment season is here, and pilots may be overlooking one of the most valuable benefits available through their airlines. In this episode of the Pilot Money Guy, Scott explains how employer-sponsored legal plans can make estate planning more affordable and accessible. We explore the importance of trusts, beneficiary designations, and protecting your family from unnecessary complications. Plus, Scott shares his personal “When I Die” binder and how a little preparation today can make life much easier for your loved ones tomorrow. Here’s some of what we discuss in this episode: ✈️ Open Enrollment: Don't overlook your legal benefits ⚖️ Estate Planning: Affordable options for airline pilots 📝 Beneficiary Check: Avoid costly designation mistakes 🏡 Trust Planning: Protect assets and minimize probate 👨‍👩‍👧 Family Protection: Plan for your children's future 📂 When I Die: Create your family's emergency binder Resources: Our website: https://pilotmoneyguy.com/ Phone: (419) 314-4139 Schedule an introductory call: http://callosborn.com/ Get your copy of “Cleared to Retire:” https://pilotmoneyguy.com/toolkit/ Check us out on YouTube: https://www.youtube.com/channel/UC_hNGqqVjqgtuoYZlu9i4yQ

  2. Oct 22

    Pilots: Don't Miss These Year-End 401(k) Moves!

    📱 Get your customized planning started by booking a call: http://callosborn.com/  ✈️ Order your no-cost Pilot Money Toolkit today: https://pilotmoneyguy.com/toolkit/ The clock is ticking on your 2026 retirement planning! Are you making the most of your 401(k) before the year ends? Scot breaks down the contribution limits, catch-up opportunities, and Roth strategies airline pilots should review before December 31. Whether you're early in your flying career or approaching retirement, a few timely adjustments could make a meaningful difference in your long-term savings.  Here’s some of what we discuss in this episode: ✈️ 401(k) Limits: Know your 2026 contribution ceilings 💰 Catch-Up Contributions: Maximize age-based savings opportunities 📊 Contribution Check: Review balances before year-end 🔄 Roth Strategies: Explore after-tax conversion opportunities ⏰ Important Deadlines: Understand contributions versus conversions ⚠️ Spillover Accounts: Know where excess contributions go ✅ Payroll Verification: Confirm contributions are coded correctly Resources: Our website: https://pilotmoneyguy.com/ Phone: (419) 314-4139 Schedule an introductory call: http://callosborn.com/ Get your copy of “Cleared to Retire:” https://pilotmoneyguy.com/toolkit/ Check us out on YouTube: https://www.youtube.com/channel/UC_hNGqqVjqgtuoYZlu9i4yQ

  3. Oct 15

    Why Target Date Funds Are Failing Pilots in Their Final Decade

    📱 Get your customized planning started by booking a call: http://callosborn.com/  ✈️ Order your no-cost Pilot Money Toolkit today: https://pilotmoneyguy.com/toolkit/ Target date funds make retirement investing easy, but could that convenience be costing you as your career progresses? Scott explains why these popular 401(k) investments can be a useful starting point for younger pilots but may become less effective as retirement approaches. He explores how growing account balances, retirement income needs, and other investments should influence your strategy. If you've been relying on the same default investment for years, it might be time to reconsider whether it's still working for you. Here’s some of what we discuss in this episode: ✈️ Target Date Funds: Why convenience has limitations 📈 Growing Portfolios: When investment performance matters more 🎯 Retirement Goals: Why age shouldn't dictate allocation 📝 Income Planning: Matching investments to withdrawal needs ⚠️ Risk Management: Avoiding overly conservative or aggressive strategies 🧭 Personalized Planning: Looking beyond your default 401(k) Resources: Our website: https://pilotmoneyguy.com/ Phone: (419) 314-4139 Schedule an introductory call: http://callosborn.com/ Get your copy of “Cleared to Retire:” https://pilotmoneyguy.com/toolkit/ Check us out on YouTube: https://www.youtube.com/channel/UC_hNGqqVjqgtuoYZlu9i4yQ

  4. Oct 8

    Treasury Yield Drama: What the Headlines Are Missing

    📱 Get your customized planning started by booking a call: http://callosborn.com/  ✈️ Order your no-cost Pilot Money Toolkit today: https://pilotmoneyguy.com/toolkit/ Treasury yields are climbing, headlines are getting louder, and investors are wondering what it all means for their retirement plans. Scott breaks down why Treasury yields are rising, how higher rates can affect bonds and stocks, and why the difference between bond price and income matters. For pilots approaching retirement, understanding how and when your investments will provide income is critical. The bigger lesson? Don’t let today’s financial noise distract you from a disciplined, long-term plan. Here’s some of what we discuss in this episode: 📈 Why Treasury yields are rising- What’s driving the recent movement 🥊 Higher yields change the equation- How Treasuries compete for investor dollars 🔄 Bond prices and rates- Understanding their inverse relationship 🧩 Build your income intentionally- Know how retirement assets pay you ✈️ Tune out the noise- Stay focused on long-term goals Resources: Our website: https://pilotmoneyguy.com/ Phone: (419) 314-4139 Schedule an introductory call: http://callosborn.com/ Get your copy of “Cleared to Retire:” https://pilotmoneyguy.com/toolkit/ Check us out on YouTube: https://www.youtube.com/channel/UC_hNGqqVjqgtuoYZlu9i4yQ

  5. Oct 1

    Funding the Big Purchase Without Wrecking Your Portfolio

    📱 Get your customized planning started by booking a call: http://callosborn.com/  ✈️ Order your no-cost Pilot Money Toolkit today: https://pilotmoneyguy.com/toolkit/ Big purchases are part of life, but they can create problems when you make a funding decision without looking at the bigger financial picture. Scott walks through several ways pilots can pay for major expenses while balancing liquidity, taxes, investment growth, and debt. He also explains why these purchases shouldn’t always be treated like financial surprises if they’re likely to happen at some point anyway. A better approach is to build them into the plan before you need the money. Here’s some of what we discuss in this episode: 🏠 HELOCs: Weighing home equity and rate risk 🧾 Inherited Assets: Using inheritances with tax awareness 💼 401(k) Loans: Borrowing while sacrificing market growth 📈 Brokerage Accounts: Flexible funding for future purchases ⚠️ Margin Risk: Borrowing against volatile investments 🧠 Decision Framework: Comparing taxes, interest, and liquidity 📅 Midterm Savings: Building a dedicated spending bucket Resources: Our website: https://pilotmoneyguy.com/ Phone: (419) 314-4139 Schedule an introductory call: http://callosborn.com/ Get your copy of “Cleared to Retire:” https://pilotmoneyguy.com/toolkit/ Check us out on YouTube: https://www.youtube.com/channel/UC_hNGqqVjqgtuoYZlu9i4yQ

  6. Sep 24

    Interest Rates Move Markets — Why They Shouldn't Move You

    📱 Get your customized planning started by booking a call: http://callosborn.com/  ✈️ Order your no-cost Pilot Money Toolkit today: https://pilotmoneyguy.com/toolkit/ Fed decisions can dominate the financial headlines, but that doesn’t mean every announcement should trigger a change in your portfolio. Today, Scott explains why investors can get into trouble when short-term economic news begins driving long-term financial decisions. He looks at how a well-built plan can provide perspective when markets and headlines get noisy. The bigger question whether your strategy was built to handle whatever comes next. Here’s some of what we discuss in this episode: 📊 Stock Valuations: How borrowing costs and discount rates can influence company valuations 💵 Investor Choices: Why higher yields can make fixed-income investments more attractive relative to stocks 📺 Market Noise: How headlines surrounding Fed decisions can magnify short-term anxiety 🧠 Behavioral Risk: Why reacting emotionally to rate changes can turn into market timing 🏠 Mortgage Rates: Why anticipated Fed moves may already be reflected in borrowing costs 📈 Long-Term Investing: Staying focused on quality assets and consistent investing despite short-term volatility Resources: Our website: https://pilotmoneyguy.com/ Phone: (419) 314-4139 Schedule an introductory call: http://callosborn.com/ Get your copy of “Cleared to Retire:” https://pilotmoneyguy.com/toolkit/ Check us out on YouTube: https://www.youtube.com/channel/UC_hNGqqVjqgtuoYZlu9i4yQ

  7. Sep 17

    Five Ways Pilots Can Cut Their Tax Bills

    📱 Get your customized planning started by booking a call: http://callosborn.com/  ✈️ Order your no-cost Pilot Money Toolkit today: https://pilotmoneyguy.com/toolkit/ High-income pilots often feel like there aren’t many meaningful ways to reduce taxes without getting overly complicated or taking unnecessary risks. In this episode, Scott looks at five key strategies that may help pilots become more tax-efficient today while also thinking ahead to retirement. The real win is finding ways to keep more of what you earn without creating a bigger problem down the road. Here’s some of what we discuss in this episode: 🏠 Real Estate: Using rental properties and short-term rentals as potential tax-efficient assets 📈 Brokerage Accounts: Building after-tax investment assets and using tax-loss harvesting strategically 🎁 Charitable Giving: Donating appreciated stock and using donor-advised funds more efficiently 💼 401(k) Strategy: Reassessing Roth versus pre-tax contributions as income rises 🧾 Side Income: Exploring SEP IRAs, cash balance plans, and other options for self-employment income ⚠️ Tax Traps: Avoiding investments that look attractive only because of the promised write-off 🛫 Retirement Planning: Connecting today’s tax decisions to tomorrow’s income strategy Resources: Our website: https://pilotmoneyguy.com/ Phone: (419) 314-4139 Schedule an introductory call: http://callosborn.com/ Get your copy of “Cleared to Retire:” https://pilotmoneyguy.com/toolkit/ Check us out on YouTube: https://www.youtube.com/channel/UC_hNGqqVjqgtuoYZlu9i4yQ

  8. Sep 10

    Inheriting the Nest Egg- What Pilots Need to Know

    📱 Get your customized planning started by booking a call: http://callosborn.com/  ✈️ Order your no-cost Pilot Money Toolkit today: https://pilotmoneyguy.com/toolkit/ Inheriting money can create opportunities, but it can also bring unexpected taxes, paperwork, and family complications. Scott explains why families should “rehearse” the inheritance process before it happens, including reviewing estate plans, beneficiary designations, trusts, and probate exposure. He also breaks down how inherited Roth, pre-tax, and taxable assets are treated differently. With some prior planning, families can reduce surprises, improve tax efficiency, and make the inheritance process much easier to navigate.  Here’s some of what we discuss in this episode: 🛫 Rehearse the Plan: Know what happens before it happens  📄 Check Beneficiaries: Avoid costly designation mistakes  ⚖️ Understand Probate: Know which assets bypass the process  🎁 Know the Tax: Different assets inherit differently 🎯 Use It Wisely: Let inheritance support your own goals Resources: Our website: https://pilotmoneyguy.com/ Phone: (419) 314-4139 Schedule an introductory call: http://callosborn.com/ Get your copy of “Cleared to Retire:” https://pilotmoneyguy.com/toolkit/ Check us out on YouTube: https://www.youtube.com/channel/UC_hNGqqVjqgtuoYZlu9i4yQ

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About

Welcome to The Pilot Money Guy Podcast, where we navigate the skies of financial success with your host, Scott Osborn. Each episode, we soar through the challenges and opportunities unique to pilots, from debunking myths to mastering best practices in financial planning and investing. As demand for pilots reaches new heights, so too does the complexity of their financial landscapes. With Scott's expertise, we tackle common pitfalls and strategic wins that can significantly boost a pilot's financial trajectory. Whether you're an aviation professional or just fascinated by the financial skies pilots navigate, this podcast promises insights that can help anyone plot a course toward financial independence. https://pilotmoneyguy.com/ 

Information

  • Creator
    Scott Osborn
  • Years Active
    2024 - 2026
  • Episodes
    107
  • Rating
    Clean
  • Copyright
    © 2026 © 2024 The Wealthy Pilot's Podcast: Financial Flight Controls for Today's Commercial Airline Pilots
  • Show Website
    The Pilot Money Guy Podcast

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