The Pilot Money Guy Podcast

Some financial gurus love to predict doom and gloom, but what happens when their “I told you so” doesn’t actually hold up? In this episode, Scott takes a hard look at the loudest voices in the industry and why chasing their bold claims often leaves investors worse off.

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

📰 Beware of fear-driven financial “gurus”

📉 Predictions of collapse rarely pan out

📊 Trust the data, not the noise

⏳ Patience and discipline beat market timing

🛡️ Building a plan rooted in evidence

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

Downsizing in retirement often sounds like an easy decision, but it’s rarely that simple. In this episode, Scott breaks down some of the most common downsizing myths - like whether a smaller home really lowers monthly expenses - and explains why the numbers don’t always add up.

Tune in for practical insights to help you weigh whether moving to a smaller home is truly the right choice for you. 

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

🏡 Downsizing doesn't always lower costs

💰 Using home equity for debt or savings isn’t always the best move

🛠️ Simple home modifications can prepare you for long-term care needs

🏖️ Know your retirement goals before making big decisions

👨‍👩‍👧‍👦 Family dynamics should play a role in your decision

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

September and October often get a bad rap in the investing world, but are they truly risky months? In this episode, Scott breaks down the truth behind these "turbulent" months. While data shows September's historical slight negative returns, it’s important to peel back the layers. If you're nearing retirement, it's crucial to understand the data and avoid knee-jerk reactions to monthly trends.

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

📉 September’s performance: Is it as bad as it seems? 

📊 Data vs. headlines: Making informed decisions

💰 The impact of staying invested during market volatility

⏳ Retirement strategies that consider the whole picture

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

Falling behind on retirement savings can feel overwhelming, especially if you’re only just hitting your financial stride in your 30s, 40s, or even 50s. In this episode, Scott tackles the big question: How do you catch up if you feel late to the retirement party? From military pilots transitioning into airlines to career changers carrying student loans, many people wonder if they’ve missed their window to build a stronger nest egg. The good news? With the right strategy, time, and income, you can still get on track.

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

✈️ Different paths to the airline career = different financial starting points

🎯 Two critical levers for catching up: tax efficiency & investment returns

💸 Maxing out your 401k & exploring smart savings options beyond it

🛡️ Insurance and risk management are part of “catching up”

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

According to a recent survey, the emotional and financial burden of paying for college often exceeds expectations. And it’s affecting everything from retirement plans to mental health. In this episode, Scott unpacks what families are really facing and how to make smarter decisions that won’t derail your own future.

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

💰 Why pausing retirement savings can be a costly mistake

🎓 The cost of college vs. return on investment

👨‍👩‍👧 New survey data on parents’ sacrifices

🔧 Alternatives like trades, scholarships, and CCP programs

Resources for this episode:

Citizens Financial Group’s 2024 College Planning Study 

Sallie Mae’s “How America Pays for College” Report 

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

Most people don’t feel wealthy. But what if your day-to-day habits are quietly building serious financial strength? A recent article from Kiplinger outlined five surprising signs that you might be richer than you think. And none of them involve yachts or private jets. In this episode, Scott analyzes the habits that signal real, lasting wealth and what to do if you are (or aren’t) on the right track.

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

💰 Emergency funds: your safety net for life’s surprises

⚖️ The importance of living below your means 

🚀 Building diversified accounts vs. just target-date funds

🔑 The power of multiple income streams

🕰️ Why patience builds lasting wealth

Kiplinger Article: 

7 Signs You’re Secretly Getting Rich (and Don’t Even Know It)

https://www.kiplinger.com/personal-finance/signs-youre-secretly-getting-rich-and-dont-even-know-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

The kids may be heading back to class, but it’s not a bad time for adults to hit the books too, especially when it comes to retirement. So, let’s test your knowledge with a quick financial pop quiz and see how ready you really are.

Here are the quiz questions for today:

📝 At what age do you get full Social Security if born after 1960?
 📝 Max IRA contribution for those 50+ in 2025?
 📝 Which retirement account requires RMDs?
 📝 What does the 4% rule mean in retirement planning?
 📝 True or False: Target Date Funds are always the best choice.
 📝 What financial risk do retirees face most?

4% Rule Episode:

https://www.buzzsprout.com/2384642/episodes/17315990

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

This week, Scott sits down with Jason Watson from WCG CPAs and Advisors to talk about the top 3 mistakes high-income pilots should avoid when investing in rental properties. As pilots and other high earners look for ways to diversify their income beyond their primary careers, rental properties offer a powerful path to building lasting wealth- if you approach it the right way.

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

🛫 Why pilots’ schedules make rentals a uniquely attractive investment

📉 The #1 misconception about rentals as a tax-saving strategy

🏠 Short-term rental loophole explained and how to qualify

💰 Using cost segregation and bonus depreciation to your advantage

📋 Which personality types make the best landlords

Resources for this episode:

Get Jason’s book, I Just Got a Rental, What Do I Do?

https://www.amazon.com/Just-Got-Rental-What-Considerations/dp/B0DJBY6ZQ3

WCG CPAs and Advisors 

https://wcginc.com/

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

We’re back for Part 2 of the “7 Deadly Sins of Investing,” and these final three may be the hardest to overcome, because they’re not technical; they’re emotional. Scott explores how fear, greed, and impatience can quietly creep into our financial decisions and derail long-term success. These aren’t just feelings; they’re patterns that lead to poor timing, unnecessary risk, and abandoning a perfectly good plan.

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

🛣️ How emotional reactions pull people off track

😵‍💫 Why fear leads to bad financial decisions

🎰 Greed often turns investing into a gamble

⏱️ The ticking trap of impatience

🛶 The power of discipline and staying the course

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

We’re kicking off a special two-part series on the “7 Deadly Sins of Investing.” In this first installment, Scott unpacks four of the biggest behavioral missteps investors make, especially when emotions run high or market headlines dominate the news. If you're over 50 and starting to think seriously about protecting your nest egg, this is one episode you won’t want to miss.

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

🌪️ Why market timing usually backfires

🧺 The trap of owning “too much” of everything

🚫 How overconfidence could lead to under-diversification 

🚀 Why past performance isn’t a future guarantee 

💰 Discipline beats chasing returns 

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