The Pilot Money Guy Podcast

📱 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

📱 Get your customized planning started by booking a call: http://callosborn.com/ 

✈️ Order your no-cost Pilot Money Toolkit today: https://pilotmoneyguy.com/toolkit/

Hitting age 50 in the cockpit? That’s your cue to get serious about the next mission, turning years of flying into a well-fueled retirement plan. In this episode, Scott walks pilots through how to rethink contributions and start building more tax-efficient income for life after mandatory retirement. Don’t skip this pre-flight check if you’re a pilot staring down the runway to retirement.

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

✈️ Next Mission: Age 50 shifts focus toward retirement

💰 Catch-Up Options: New contributions expand Roth opportunities

📊 Contribution Strategy: Coordinate airline, employee, and spillover funds

🧾 Tax Buckets: Build flexible retirement income sources

🔭 Future Focus: Reverse engineer retirement from age 75

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

📱 Get your customized planning started by booking a call: http://callosborn.com/ 

✈️ Order your no-cost Pilot Money Toolkit today: https://pilotmoneyguy.com/toolkit/

Wondering if these new “Trump accounts” are really worth your attention as a pilot? Scott breaks down where these kids’ IRAs fit into your overall flight plan and why funding priorities matter more than chasing the latest headline strategy. Stick around to see whether these new accounts actually deserve a place in your cockpit, or just a note in the logbook.

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

💰 New Accounts: Children can invest without earned income

💵 Contribution Limits: Families may add five thousand annually

⚖️ Tax Tradeoffs: Other accounts may offer better treatment

📋 Funding Priorities: Handle core financial goals first

✈️ Pilot Strategy: Match contributions to broader planning needs

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

📱 Get your customized planning started by booking a call: http://callosborn.com/ 

✈️ Order your no-cost Pilot Money Toolkit today: https://pilotmoneyguy.com/toolkit/

When the market keeps hitting new highs, it’s easy to wonder whether you should keep investing, sit in cash, or wait for the next dip. But expensive markets don’t automatically mean bad opportunities — and sitting on the sidelines can create risks of its own. Scott explains why all-time highs should be understood in context. The real key is having a disciplined strategy that helps you stay invested, manage risk, and avoid turning fear into a long-term mistake.

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

🌎 Beyond S&P: Explore other asset classes

⚠️ Cash Risk: Sitting out has consequences

🧮 P/E Ratios: Valuations need context

🧺 Diversification: Avoid one expensive basket

⚖️ Rebalancing: Manage risk with intention

🧠 Long View: Don’t fear strong markets

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

📱 Get your customized planning started by booking a call: http://callosborn.com/ 

✈️ Order your no-cost Pilot Money Toolkit today: https://pilotmoneyguy.com/toolkit/

What does it really take to turn a career’s worth of savings into a reliable retirement paycheck? In this episode, Scott breaks down how pilots can start thinking about retirement income without overcomplicating the process. It’s a practical conversation about gaining clarity, making smarter decisions, and building confidence before the next chapter begins. 

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

💸 Monthly Expenses: Know what hits home

🧾 Tax Planning: Your biggest retirement expense

🔁 Tax Efficiency: Create Roth conversion windows

🏦 Fixed Income: Measure reliable income sources

🧠 Risk Tolerance: Use data, not feelings

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

📱 Get your customized planning started by booking a call: http://callosborn.com/ 

✈️ Order your no-cost Pilot Money Toolkit today: https://pilotmoneyguy.com/toolkit/

What does financial freedom actually mean, and how do you achieve it? In this special Independence Day episode, Scott uses America's 250th anniversary as a reminder that financial independence is built through intentional decisions, not luck. Break free from autopilot and start intentionally marching toward financial freedom. Plus, stick around to discover one of the most powerful moves you can make this year.

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

🧠 Wealth Mindset – Thinking like a future millionaire.

💼 Income Balance – Growing wealth without lifestyle creep.

📈 Compound Growth – Letting time build your wealth.

🗺️ Financial Planning – Creating a roadmap for success.

✅ Take Action – Overcoming procrastination and getting started.

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

📱 Get your customized planning started by booking a call: http://callosborn.com/ 

✈️ Order your no-cost “Wealthy Pilot Toolkit” today: https://retireairlines.com/pilot-retirement-toolkit/

The House has overwhelmingly approved legislation that would raise the mandatory airline pilot retirement age from 65 to 67, sparking debate across the aviation industry. In this episode, Scott explores what the Let Experienced Pilots Fly Act could mean for pilots and why the bigger question isn't whether the law changes- it's whether your financial plan is prepared for multiple career outcomes. 

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

✈️ Career Planning: Preparing for multiple outcomes

⚠️ Hidden Risks: Why assumptions can be dangerous

🛡️ Financial Resilience: Building flexibility into retirement

💰 Income Reality: Overtime isn't guaranteed

🎯 Take Control: Focus on what you can influence

🚀 Early Readiness: Be prepared before required

Resources:

Our website: https://retireairlines.com/

Phone: (419) 314-4139

Schedule an introductory call: http://callosborn.com/

Check us out on YouTube: https://www.youtube.com/channel/UC_hNGqqVjqgtuoYZlu9i4yQ

📱 Get your customized planning started by booking a call: http://callosborn.com/ 

✈️ Order your no-cost “Wealthy Pilot Toolkit” today: https://retireairlines.com/pilot-retirement-toolkit/

SpaceX's highly anticipated public debut has investors everywhere wondering if they're missing the next big opportunity. Scott breaks down the hype surrounding IPOs and explores how disciplined investors can avoid costly emotional decisions. He shares practical guidance on treating IPOs like speculative “Vegas money” and keeping new opportunities aligned with a long-term retirement and investment plan. 

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

📉 Track Record: Most IPOs lag markets

👨‍✈️ Pilot Risks: Avoid chasing hot investments

📊 Index Exposure: Owning SpaceX indirectly

💸 FOMO Trap: Emotional investing can backfire

🔁 Smart Entry: Dollar-cost averaging individual stocks

🚀 Stay Disciplined: Process beats excitement every time

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

📱 Get your customized planning started by booking a call: http://callosborn.com/ 

✈️ Order your no-cost “Wealthy Pilot Toolkit” today: https://retireairlines.com/pilot-retirement-toolkit/

High income can feel like freedom, but for many pilots it quietly becomes a trap. In this episode, Scott unpacks the “golden handcuffs” that show up as lifestyle creep, overwork, and financial pressure. You’ll hear why simply making more money isn’t the solution, and how a few mindset shifts can restore flexibility and control. Tune in if you want your pay increases to buy you freedom, not stress.

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

🔒 Golden Handcuffs: When lifestyle limits your freedom

📈 Lifestyle Creep: Why raises don't always create wealth

⚠️ Income Illusion: High earners can still feel trapped

📊 Household Audit: Managing money like a business

✈️ Financial Margin: Building flexibility before you need it

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

📱 Get your customized planning started by booking a call: http://callosborn.com/ 

✈️ Order your no-cost “Wealthy Pilot Toolkit” today: https://retireairlines.com/pilot-retirement-toolkit/

Tax deductions sound great… until you start looking at the tradeoffs hiding underneath the surface. In this episode, Scott breaks down the hidden risks of market-based cash balance plans and why many pilots may be overvaluing short-term tax deferral while overlooking long-term consequences. He explains how these “spillover” retirement accounts work, why they often underperform broader markets, and how they can create future tax problems, liquidity issues, and less control over your money.

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

✈️ Spillover Plan Basics

💰 Tax Deferral vs Savings

📉 Hidden Performance Problems

🔒 Liquidity & Control Risks

📊 Building Tax Flexibility

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