The Pilot Money Guy Podcast

The market’s hitting record highs, but does that mean it’s too risky to invest right now? In this episode, Scott breaks down what all-time highs actually mean for long-term investors. You’ll hear how short-term fear often leads to poor decisions and why zooming out can help you stay grounded.

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

📈 Why investing at all-time highs isn’t as scary as it seems

⏳ Why time in the market beats timing the market

📉 What short-term pullbacks really mean for long-term gains

🧠 The emotional traps investors fall into at market highs

🔄 The importance of discipline and consistency through market ups and downs

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

Dave Ramsey is one of the most recognized voices in personal finance. His 9-step retirement plan is simple, direct, and built for mass appeal. But is it really the best path for your retirement? 

You'll hear where Scott agrees, where he diverges, and what every pilot needs to know about balancing tax strategies, health care costs, and when to bring in an advisor. 

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

🚨 What mass-market advice misses + how intentional planning can change your retirement

📊 Why 15% retirement savings isn’t a one-size-fits-all answer

✈️ The power of maximizing your 401(k) performance as an airline pilot

🏥 Using HSAs for tax-free healthcare expenses

💼 DIY vs. Advisor: Knowing when it's time to hand off the controls

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 Big Beautiful Bill (BBB) is here, and with it comes tax updates that could shape your financial strategy for years to come. In this episode, Scott and Marc break it all down in clear, practical terms: what stays, what changes, and what it means for pilots, high earners, and retirees alike. But here’s the catch: many of these changes are temporary, so smart planning now could make a big difference later.

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

🧠 Taking advantage of today’s low tax rates while they last 

🏡 Location, location, location… How moving states could slash your tax bill

👴 Are seniors getting a bigger tax break? 

🎯 New planning opportunities for families- from baby accounts to Roth strategies

⏳ The clock’s ticking- the expiration of these benefits 

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

As we celebrate the Fourth of July, this episode explores what independence truly looks like in retirement, beyond fireworks and freedom. Scott dives into five core areas of independence that every retiree (or future retiree) should be aiming for as they prepare for life after work. It's not just about having enough money, but having control, peace of mind, and a plan that works.

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

📆 Retiring on your schedule, not because you have to 

💰 Ditching debt and covering fixed expenses 

🚫 Minimizing fear of government changes and taxes 

🏝️ Maintaining your lifestyle in retirement 

👨‍👩‍👧‍👦 Leaving a legacy, not a mess, for your family

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

Estate planning is something we all know we should do, but it’s often pushed to the bottom of the list. In this episode, Scott shares a heartbreaking real-life story: a close friend’s brother died suddenly at 42. Recently divorced, with two young sons and no estate plan in place, the aftermath was a painful legal tangle. It’s a tragic example of what happens when planning is left undone, and how the people you love end up bearing the weight.

Listen in as Scott talks through the essentials of estate planning – from why a simple will isn’t enough to the key life events that should prompt updates. 

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

🛑 Real-life story: the tragedy of having no plan

📜 Why a will isn’t a complete estate plan

🚨 Key life events that should trigger updates

👨‍👩‍👧‍👦 The risk of family conflict without communication

⚖️ How to avoid probate and protect your intent

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 4% rule gets talked about like gospel in retirement planning. But let’s be honest, it’s always been more of a rough guess than a golden rule. Now, its original creator is revising it to 4.7%. So, does that mean your retirement paycheck just got a raise, or is this just another headline that oversimplifies a complex decision?

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

📏 Why the 4% rule became the “default” retirement planning guide

🔍 What the 4.7% update really means (and doesn’t mean)

🖩 Why drag-and-drop spreadsheets can create false confidence

🧩 Building your retirement around your actual lifestyle, risk tolerance and income mix 

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

Target-date funds just passed $4 trillion in assets. They’re now the default investment in many 401(k)s, and millions of Americans are using them without really understanding how they work. So, are they a smart choice… or just the easiest one? 

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

🧭 Why defaulting to a target-date fund could misalign with your goals

📉 How these funds reduce risk—but possibly too early or too much

⚠️ The hidden costs and risks that go beyond fees

🎯 What to do instead if you're ready for more control

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

A little hope is good for the soul, but when it comes to retirement planning, wishful thinking can lead to serious financial mistakes. Today, Scott’s walking through five common examples of wishful thinking that can quietly damage your retirement, and how you can build a plan that protects your future instead of relying on luck.

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

🧾 A major tax myth you need to face

🏠 Does cost of living ever drop?

⚠️ The dangers of DIY Planning

🎢 Market return assumptions that could backfire

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

Today, we’re talking about Type A personalities. If you’re driven, competitive, and goal-oriented, then you’re part of the club that often struggles during difficult markets. When things get tough, your instinct is to work harder, push more, and fix the problem. But in investing, that instinct can sometimes backfire. 

In this episode, Scott breaks down the challenges Type A investors face when market volatility strikes and why a high-performance mindset doesn’t always translate into better investment results. 

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

💼 Why Type A traits often clash with market discipline

📉 The danger of overreacting in volatile conditions

🔄 Rebalancing vs. tinkering: knowing the difference

🧠 Staying calm and following a proven process

📋 The power of an investing “checklist” during chaos

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’ve all heard that Americans don’t save enough for retirement, but what if the opposite is true for you? Can you save too much? In this episode, Scott tackles a surprising but important question raised by a listener: “Are we over-saving at the expense of living now?” As an airline professional, it can be easy to feel like you’re doing too little, or maybe even too much. This conversation helps you find the balance.

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

💸 Can you save too much for retirement?

🧭 Why “starting with the end in mind” matters most

📉 The real risk of under-saving and over-saving

🧠 How your past shapes your money biases today

✈️ What pilots need to know about timing, taxes, and lifestyle

T. Rowe Price Calculator: 

https://www.troweprice.com/personal-investing/resources/insights/youre-age-35-50-or-60-how-much-should-you-have-by-now.html

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