📱 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/

Is successful investing about skill or simply being lucky? In this St. Patrick’s Day–themed episode, the conversation explores the popular idea of “luck” in investing and why relying on it can be risky. Scott explains how many investors mistake lucky outcomes- like a winning stock pick or perfectly timed trade- for strategy. Instead, he highlights the value of discipline, diversification, and a long-term process.

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

🍀 Luck vs. strategy in investing – Why lucky outcomes can mislead investors into risky habits

📉 The danger of stock picking and market timing

🧭 Why successful investors follow a plan instead of chasing trends

📊 Diversification and rebalancing – Core practices that improve long-term results

⏳ The power of compounding – Staying invested allows dividends and growth to quietly build wealth over 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/

For many people, retirement saving feels simple: contribute to the 401(k) and call it a day. But what happens when you want to save more than that? Scott explains how to think about saving and investing outside a workplace plan and why a good strategy includes more than just your retirement account. He also walks through the financial “order of operations,” and how to think about building a broader portfolio that supports both long-term growth as you near retirement. 

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

✈️ Beyond The 401(k): Other ways to build wealth

📈 Brokerage Accounts: Flexible investing without contribution limits

🎯 Savings Goals: Match accounts to future needs

🧠 Portfolio Mindset: Manage wealth across all assets

📋 Financial Order: Prioritize saving and investing decisions

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/

Every time global tensions flare up, the same question resurfaces: should investors make a move? Oil spikes. Headlines turn dramatic and talking heads predict disaster. Scott zooms out and examines what history shows, what usually happens next, and how to avoid letting short-term fear override long-term progress.

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

🌍 Geopolitical Risk – Conflict and global uncertainty

🧠 Emotional Discipline – Avoiding reactionary decisions

🧩 Diversification – Managing sector concentration risk

📰 News Noise – Headlines vs market pricing

📊 Market Resilience – Historical recovery patterns

⏳ Long-Term Focus – Staying aligned with time horizon

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 “Backdoor Roth” might sound complicated - or even questionable - but it’s completely legal and incredibly powerful. In this episode, Scott demystifies how high-income earners can legally build tax-free retirement income using a simple, repeatable strategy. He explains income limits, the pro rata rule, and why small annual contributions can quietly grow into seven figures over time. If you’ve outgrown Roth contribution limits but still want tax-free growth, this is low-hanging fruit you don’t want to ignore.

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

✈️ Why high earners get blocked from direct Roth contributions
 💰 How the non-deductible IRA + conversion strategy works
 ⚠️ The pro rata rule and why mixing IRA dollars can create tax headaches
 📈 The power of compounding small annual contributions
 🚀 Mega Backdoor Roth vs. standard Backdoor Roth explained

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/

Filing your taxes checks a box, but it doesn’t tell you if you’re leaving opportunities on the table. Scott breaks down the difference between simply getting a return done and having a long-term tax plan. You’ll also hear why timing, coordination, and follow-through matter just as much as accuracy. It’s a practical reminder that smart tax decisions rarely happen at the last minute and without proper planning.

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

🧾 Filing vs. Planning: Compliance versus long-term strategy

⚠️ Procrastination Risks: How delays create mistakes

📋 Filing Checklist: Key items people overlook

🔍 Return Review: Using last year to plan ahead

🔁 Advanced Strategies: Roth conversions and more

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/

Most people know financial planning is important, but few really understand what happens after you say “yes” and become a client. Scott pulls back the curtain on his step‑by‑step planning process, specifically through the lens of pilots. You’ll get a feel for how he analyzes your situation and helps you follow through without getting bogged down in complexity. If you’ve ever wondered what happens behind the scenes when you hire a financial advisor, this episode gives you a clear, no‑nonsense look.

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

🧭 Initial Review: Understanding the full financial picture

🎯 Plan Design: Aligning goals with strategy

🛠️ Implementation: Putting the plan into motion

🔄 Ongoing Management: Adjusting as life and markets change

🗣️ Communication: Staying aligned over 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://keap.page/lde199/the-pilot-s-planner-toolkit.html

Geopolitical headlines are louder than ever- but should they influence your investment decisions? In this episode, Scott explains why reacting to global events, elections, or policy noise often does more harm than good. Using real-world examples, aviation parallels, and disciplined portfolio principles, Scott breaks down how investors can stay grounded, avoid emotional mistakes, and focus on long-term outcomes.

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

✈️ Why geopolitical headlines are a poor investing compass 

🧠 The danger of emotional and reactionary decisions 

📈 Why long-term perspective beats short-term noise 

🔄 Understanding second- and third-order economic effects

📋 Investing with a checklist, not a headline 

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://keap.page/lde199/the-pilot-s-planner-toolkit.html

After a year marked by volatility, uncertainty, and more than a few economic curveballs, it’s understandable if optimism doesn’t come easily. But at least one economist is arguing that the outlook for 2026 may be brighter than many people expect. Today, Scott breaks down the case for a stronger economy ahead- while also explaining why pilots should be cautious about letting economic predictions drive their financial decisions.

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

📊 The economy and the market are not the same thing 

💰 Why consumer cash flow could improve in 2026 

⛽ How energy prices and interest rates impact growth 

⚠️ The dangers of relying on economic predictions 

🎯 What investors can actually control long term

Bloomberg News Opinion Column:

https://www.fa-mag.com/news/five-reasons-to-be-optimistic-about-the-2026-economy-85324.html?section=68

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://keap.page/lde199/the-pilot-s-planner-toolkit.html

A new government-backed savings account for kids is on the way, and on the surface, it sounds like a win. Free money, long-term investing, and a head start for the next generation. But once you look closer, Trump Accounts raise some questions. Scott walks through the pros, the trade-offs, and how to decide whether these accounts fit into your family’s broader plan.

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

👶 New Kids’ Accounts: What Trump Accounts are and who qualifies

💰 Free Money Factor: Why the government contribution matters

🧾 Rules & Restrictions: Contribution limits and account mechanics

⚖️ Pros vs. Cons: Where these accounts help and where they fall short

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://keap.page/lde199/the-pilot-s-planner-toolkit.html

A new year is the perfect time to revisit the numbers driving your retirement plan- and in this episode, Scott walks through the most important 401(k) updates pilots need to understand for 2026. From standard contribution limits to catch-up and “super catch-up” opportunities, Scott explains what’s changed, who it affects, and why contribution strategy matters just as much as contribution size. The conversation goes deeper into new rules requiring catch-up contributions to go into Roth accounts, the long-term value of tax diversification, and the hidden risks of relying too heavily on pre-tax savings.

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

💡 401(k) contribution and catch-up limits for 2026 

🦸 “Super catch-up” opportunities for ages 60–63 

🧾 New rules requiring catch-up contributions to be Roth 

⚖️ Pre-tax vs. Roth strategy and tax diversification 

🚨 The hidden risk of the widow’s tax trap 

🎯 Why contribution strategy matters as much as contribution amount

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