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:

Schedule A Call with Scott: http://callosborn.com/

Scott's Book, A Pilot's Guide To Maximizing Wealth & Cashflow In Retirement: https://amzn.to/3xSn1ii

The Pilot's Planner Website: https://thepilotsplanner.com/

Watch the podcast on YouTube! https://www.youtube.com/@ThePilotsPlanner

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:

Schedule A Call with Scott: http://callosborn.com/

Scott's Book, A Pilot's Guide To Maximizing Wealth & Cashflow In Retirement: https://amzn.to/3xSn1ii

The Pilot's Planner Website: https://thepilotsplanner.com/

Watch the podcast on YouTube! https://www.youtube.com/@ThePilotsPlanner

Recession fears are back in the headlines, but should they be back in your financial plan, too? We’re in the middle of earnings season and data is coming in, so Scott will tackle the question: Are we heading for a recession?

With shrinking GDP, rising inflation, and uncertain interest rate moves by the Fed, we’ll try to decipher what the latest economic signals really mean and discuss how investors should think about their portfolios right now.

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

📉 What GDP shrinkage really means for investors

⏳ Why timing the market rarely works

📆 How to prepare for a recession if you're near retirement

🔁 Understanding sequence-of-return risk

📈 History shows the market rebounds before the economy does

Resources:

Schedule A Call with Scott: http://callosborn.com/

Scott's Book, A Pilot's Guide To Maximizing Wealth & Cashflow In Retirement: https://amzn.to/3xSn1ii

The Pilot's Planner Website: https://thepilotsplanner.com/

Watch the podcast on YouTube! https://www.youtube.com/@ThePilotsPlanner

In part two of this special Masters series, Scott takes us to the “back nine”- the final stretch of retirement planning where pressure builds and smart decisions matter most. From avoiding risky plays in your 50s and 60s to understanding how emotions can derail your strategy, Scott lays out what it really means to finish strong.

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

⛳ Why “Amen Corner” = age 50+ in your financial life

🎯 Avoiding the urge to overcorrect under pressure

🧠 Discipline vs. emotion in your investment decisions

📉 Why playing too safe can be just as risky

📊 The power of consistency over flashy wins

Resources:

Schedule A Call with Scott: http://callosborn.com/

Scott's Book, A Pilot's Guide To Maximizing Wealth & Cashflow In Retirement: https://amzn.to/3xSn1ii

The Pilot's Planner Website: https://thepilotsplanner.com/

Watch the podcast on YouTube! https://www.youtube.com/@ThePilotsPlanner

The Masters is a beautiful reminder of just how much strategy, patience, and long-term focus goes into a great round of golf. Turns out, retirement works a lot like the game. Today, we’re teeing up a few key lessons from the course and how they translate into smarter planning for your financial future.

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

⛳ What golf teaches us about investing

⚠️ Avoiding overconfidence after short-term wins

📉 Why steady strategy beats risky moves

🏌️‍♂️ Diversification = using every club in your bag

🛠️ The value of planning your shots (and your retirement)

Resources:

Schedule A Call with Scott: http://callosborn.com/

Scott's Book, A Pilot's Guide To Maximizing Wealth & Cashflow In Retirement: https://amzn.to/3xSn1ii

The Pilot's Planner Website: https://thepilotsplanner.com/

Watch the podcast on YouTube! https://www.youtube.com/@ThePilotsPlanner

Plenty of people have concerns about stock market volatility, a potential recession on the horizon, and fears for the economy amidst federal layoffs and tariffs. What if you’ve had 2025 marked on the calendar for a while as the year you plan to retire? Is this a bad time to do it?

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

0:00 – Intro

2:08 – Headline response to market

3:49 – Sequence of returns risk

6:19 – Different market sectors

8:07 – The tendency to chase performance

9:36 – Investor sentiment and diversification

Resources:

Schedule A Call with Scott: http://callosborn.com/

Scott's Book, A Pilot's Guide To Maximizing Wealth & Cashflow In Retirement: https://amzn.to/3xSn1ii

The Pilot's Planner Website: https://thepilotsplanner.com/

Watch the podcast on YouTube! https://www.youtube.com/@ThePilotsPlanner

What if you could become your own banker and take control of the way you finance your life? Today we’re excited to welcome on Brian Moody and Hans Tooey of Remnant Finance to explore the Infinite Banking Concept- a financial strategy designed to help you protect, save, and grow your wealth without relying on traditional banks.

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

0:00 – Intro

1:00 – Background on our guests

4:50 – The Infinite Banking concept

13:25 – Flipping financing

22:03 – Controlling the banking function

25:07 – Different types of insurance policies

36:05 – Case study

40:08 – How value accrues

47:30 – Final thoughts

Resources for this episode:

Learn more about Remnant Finance: https://remnantfinance.com/

Resources:

Schedule A Call with Scott: http://callosborn.com/

Scott's Book, A Pilot's Guide To Maximizing Wealth & Cashflow In Retirement: https://amzn.to/3xSn1ii

The Pilot's Planner Website: https://thepilotsplanner.com/

Watch the podcast on YouTube! https://www.youtube.com/@ThePilotsPlanner

Thinking about starting a side gig? Many pilots explore side hustles like real estate or passion projects, but how do these extra income streams impact retirement planning? Are there tax advantages you should be taking advantage of? And how can you ensure your side hustle is working for you, not creating extra stress?

In this episode, Scott breaks down the impact of side gigs on your long-term financial plan. We’ll discuss the most common side hustles for pilots, the tax benefits of structuring them properly, and why having multiple income streams can be a game changer for your financial security.

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

0:00 – Intro

2:11 – Real estate as a side gig

3:13 – Consulting and passion projects

5:01 – Tax efficiency and diversification of income

9:02 – Final thoughts on side gigs

Resources:

Schedule A Call with Scott: http://callosborn.com/

Scott's Book, A Pilot's Guide To Maximizing Wealth & Cashflow In Retirement: https://amzn.to/3xSn1ii

The Pilot's Planner Website: https://thepilotsplanner.com/

Watch the podcast on YouTube! https://www.youtube.com/@ThePilotsPlanner