📱 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

📱 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

📱 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

📱 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

📱 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

📱 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