The Pilot Money Guy Podcast

Scott Osborn
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  • Investing
  • Updated 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. 4d ago

    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

  2. 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

  3. 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

  4. 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

  5. Sep 3

    Shiny Object Syndrome: The 401(k) Mistakes That Cost Pilots

    📱 Get your customized planning started by booking a call: http://callosborn.com/  ✈️ Order your no-cost Pilot Money Toolkit today: https://pilotmoneyguy.com/toolkit/ It’s easy to get distracted by the latest hot investment, market headline, or fund that just had a great run. For the 100th episode, Scott is celebrating by tackling Shiny Object Syndrome and the investing habits that can pull a long-term retirement strategy off course. He also introduces his new book, Cleared to Retire, built to help pilots make smarter decisions inside their 401(k) and prepare for the transition into retirement. Here’s some of what we discuss in this episode: ✨ Shiny Objects: Excitement can derail strategy ⏱️ Market Timing: Don’t disrupt compounding 🎯 Default Funds: Convenience isn’t always optimal 🔙 Past Performance: Don’t chase yesterday’s winners 📈 Stock Picking: More risk can mean less return 🧭 Contribution Strategy: Use the right accounts 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. Aug 27

    The 5 D’s of Retirement

    📱 Get your customized planning started by booking a call: http://callosborn.com/  ✈️ Order your no-cost Pilot Money Toolkit today: https://pilotmoneyguy.com/toolkit/ According to a recent Kiplinger article, there are five keys to a retirement plan that hold up over time. They all happen to start with the same letter— which either means it's a great framework or someone really wanted it to work out that way. In this episode, Scott walks through the “5 D’s” of retirement planning and how each one plays a role in helping retirees build a plan that can hold up over time. Here’s some of what we discuss in this episode: 🧺 Diversification: Balance growth and income ⏳ Duration: Plan across generations 🛡️ Downside Protection: Prepare for market declines 💵 Income Needs: Separate fixed and flexible 🧾 Tax Drag: Reduce long-term headwinds How to Turn a $1 Million Nest Egg Into a Lifetime Income Machine https://www.kiplinger.com/retirement/retirement-plans/how-to-turn-a-usd1-million-nest-egg-into-a-lifetime-income-machine 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. Aug 20

    Why Politics (and the Midterms) Are Bad Investment Policy

    📱 Get your customized planning started by booking a call: http://callosborn.com/  ✈️ Order your no-cost Pilot Money Toolkit today: https://pilotmoneyguy.com/toolkit/ Politics and portfolios don’t always mix, but midterm season makes it really tempting to try. Scott breaks down why election headlines can lure investors into market timing, even though the data just doesn’t back bailing on a long-term plan. You’ll hear what history says about markets around midterms and why discipline usually beats predictions. If you’ve ever thought “I’ll just wait to see what happens in November,” this one might change your mind. Here’s some of what we discuss in this episode: 🗳️ Midterm Elections: Uncertainty can influence investors 🧠 Behavioral Traps: Emotions can hurt decisions 📊 Historical Data: Patterns offer useful context 📉 Market Volatility: Elections can increase uncertainty ⏳ Time Horizon: Long-term goals still matter 🎯 Investment Discipline: Stick with your strategy 🔇 Political Noise: Don’t invest by headlines 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. Aug 6

    3 Key Money Moves for New Major Airline Pilots

    📱 Get your customized planning started by booking a call: http://callosborn.com/  ✈️ Order your no-cost Pilot Money Toolkit today: https://pilotmoneyguy.com/toolkit/ Making it to a major airline can feel like reaching the destination, but financially, it is really the start of a new flight plan. In this episode, Scott explains why new hires should give themselves time to settle into training and onboarding, then quickly turn their attention to the financial decisions that can shape the rest of their careers. He also explains why pilots should start with the end in mind, so every contribution supports the retirement they ultimately want. Here’s some of what we discuss in this episode: ✈️ New Hire Planning: Settle in, then act quickly 🗂️ Account Consolidation: Organize old plans in one place 💰 Contribution Strategy: Coordinate Roth and pre-tax savings 🎯 End Goal: Reverse engineer the retirement you want 📈 Intentional Investing: Give every contribution a purpose ✅ Start Early: Let time strengthen your financial plan 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
    103
  • 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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