Ryan Fleming

The Pilot’s Advisor Podcast

Business EN ↓ 219 episodes

Financial and retirement planning guidance from pilot and financial advisor Ryan Fleming. The show will help you figure out how to take your financial plan from takeoff to landing with smooth sailing along the journey.

Author

Ryan Fleming

Category

Business

Podcast website

pilotsadvisor.podbean.com

Latest episode

Jul 7, 2026

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Episodes

Not Your Father’s Retirement 02.09.2021

If you’re of the age that your mom and dad retired 20 or 30 years ago, the world was a much different place when they walked away from their paychecks. Let’s talk about how things are different now. Show Notes & Info: Website: https://retirepilots.com/ Free Webinar:  https://retirepilots.com/videos/ Toolkit: https://3mvamj4f.pages.infusionsoft.net/

Learning Through Uncommon Sense 19.08.2021

At first glance, each of these statements seem like basic common sense that everyone agrees with. But when we look at the way people actually behave with their money, it seems that common sense is actually a bit uncommon. Show Notes & Info: Website: https://retirepilots.com/ Free Webinar:  https://retirepilots.com/videos/ Toolkit: https://3mvamj4f.pages.infusionsoft.net/

The Double-Edged Sword 05.08.2021

Many financial circumstances that you’ll find yourself in have both positive and negative aspects. Decisions that you can make have both good and bad consequences. Or as Sir Isaac Newton put it: ”For every action, there is an equal and opposite reaction.” Let’s talk about the way that an advisor should walk people through the thought processes that go along with various predicaments. Show Notes &...

Financial Fact Or Fiction 15.07.2021

Sometimes the easiest way to learn about something is make it really simple. Like some of the first true/false tests you might have taken in school, let’s play a round of fact or fiction to test your financial planning acuity. Show Notes & Info: Fleming FG Website:  https://www.flemingfg.com/ Free Webinar:  http://www.flemingfg.com/watch-ryan-pick-apart-a-pilots-401k

Revealing The Financial World’s Dirty Little Secrets 01.07.2021

If you understand some of the dirty little secrets of the financial world, it’ll help you cut through the clutter and allow you to focus on what’s most important. So, let’s reveal some of those secrets on this episode. Show Notes & Info: Fleming FG Website:  https://www.flemingfg.com/ Free Webinar:  http://www.flemingfg.com/watch-ryan-pick-apart-a-pilots-401k

Where Crisis & Opportunity Meet 17.06.2021

To write the Chinese word for “crisis,” you combine elements of two different Chinese characters. One character means “danger” while the other one means “opportunity.” Translated into English, it means “opportunity riding on a dangerous wind.” Let’s discuss how some of these crises might actually be opportunities, depending on your situation and perspective. Show Notes & Info: Fleming FG Website: ...

The Status Of The American Pension Plan 03.06.2021

Are pension plans truly disappearing across the country? Let’s take a look at the status of pension plans in America and how changes in that space impact you when planning for retirement. Show Notes & Info: Fleming FG Website:  https://www.flemingfg.com/ Free Webinar:  http://www.flemingfg.com/watch-ryan-pick-apart-a-pilots-401k

Kids Playing For Kids Charity 20.05.2021

On this week's show, we invite Jan "Tav" Tavrytzky to talk about his organization, Kids Playing For Kids. He initially started this organization to be more involved with his own children, but very quickly found that he had a passion in mentoring and coaching young kids. Tav talks to Ryan about some of the goals of the organization and how a program like this aids in teaching life lessons that the...

How I Lost My Retirement 06.05.2021

In March of 2020, the market took a huge downturn with the news of the Coronavirus. Since the massive drop, the market has been performing very well since that time, which has made some people feel overconfident in their investing skills. Ryan invites Lee Hyder back to the show to help explain some of the more dangerous investing methods they have recently seen. Show Notes & Info: Fleming FG Websi...

Money Lessons From The Richest Musicians 15.04.2021

Let’s look at some of the richest people in the music industry and see what lessons we can learn from them that we can apply to our own retirement planning. Show Notes & Info: Fleming FG Website:  https://www.flemingfg.com/ Free Webinar:  http://www.flemingfg.com/watch-ryan-pick-apart-a-pilots-401k

2021 Tax Tips With Zach Smith 01.04.2021

After his introduction last week, Zach Smith joins us again to answer some common questions people have about their taxes this year. Show Notes & Info: Fleming FG Website:  https://www.flemingfg.com/ Free Webinar:  http://www.flemingfg.com/watch-ryan-pick-apart-a-pilots-401k Pilot-Tax Website: https://pilot-tax.com/ Pilot-Tax Phone Number: 317-984-7666

Introducing Zach Smith & Pilot-Tax 18.03.2021

Ryan introduces his new partnership with Zach Smith and his firm, Pilot-Tax. They discuss their new partnership together, and Zach gives insight into how his firm serves clients and will work alongside the Pilot's Advisor. Show Notes & Info: Fleming FG Website:  https://www.flemingfg.com/ Free Webinar:  http://www.flemingfg.com/watch-ryan-pick-apart-a-pilots-401k Pilot-Tax Website: https://pilot-t...

This Is Why You Never Assume 04.03.2021

We often see people making certain assumptions about retirement that just aren’t correct. Let’s explore some of those. Show Notes & Info: Fleming FG Website:  https://www.flemingfg.com/ Free Webinar:  http://www.flemingfg.com/watch-ryan-pick-apart-a-pilots-401k

Can We Invest Like Billionaires? 18.02.2021

Most billionaires aren’t shy about doling out advice, quipping about what makes them successful, or trying to inspire those who seek to be like them. But with Billionaires on such a different universe when it comes to financial status, can we really take what they say and apply it to our “normal” situations? Show Notes & Info: Fleming FG Website:  https://www.flemingfg.com/ Free Webinar:  http://w...

Lessons From The Market Crash Hall Of Fame 04.02.2021

Let’s see what lessons can be learned from the most famous market crashes in United States history. From Black Tuesday to the Coronavirus pandemic, we'll take a look back to see what the past can tell us about how to prepare for the next market crash. Show Notes & Info: Fleming FG Website:  https://www.flemingfg.com/ Free Webinar:  http://www.flemingfg.com/watch-ryan-pick-apart-a-pilots-401k

The Outlandish Things That Nobody Says 21.01.2021

You’ve probably never heard anyone make these statements that we’ll provide on today’s episode. And there are some great reasons why… Show Notes & Info: Fleming FG Website:  https://www.flemingfg.com/ Free Webinar:  http://www.flemingfg.com/watch-ryan-pick-apart-a-pilots-401k

Memories Of Kevin Greene, Happy New Year, And What’s Your Retirement Lifestyle? 07.01.2021

Have you thought about what life is going to be like for you in retirement? Is there a particular lifestyle you’re seeking? Not all retirement planning is about the finances. Let’s look at some of the lifestyles that are popular among retirees and discuss some of the financial things to consider if you’re going to try to live out one of these particular living situations. Ryan will also share his...

What Should I Do With My Old 401(k) Accounts? 17.12.2020

As 2020 winds down, it might be a good time to take an inventory of your financial life to make sure everything is running smoothly to set you up for success for the new year. Many people forget about thier 401(k) accounts once they leave that employer. Ryan talks to us today about the opportunity you may have to rollover these accounts as well as telling us a story on saving taxes. Show Notes & I...

A Review Of The Top Places To Retire 03.12.2020

Is the place where you’d like to retire on the Top 15 list? On this episode, we’ll review the US News & World Report’s top 15 retirement locations and share stories of past clients who made the decision to move somewhere else for retirement and what went into those decisions from an emotional and financial standpoint. Show Notes & Info: Fleming FG Website:  https://www.flemingfg.com/ Free Webinar:...

The Financial Forecaster 19.11.2020

There are plenty of financial lessons to be learned from almost every area of life. And since the Weather Channel is everyone’s favorite station to let play in the background for hours at a time, let’s see what we can learn about retirement planning from the world of weather. Show Notes & Info: Fleming FG Website:  https://www.flemingfg.com/ Free Webinar:  http://www.flemingfg.com/watch-ryan-pick-...

Even Financial Hindsight Is 20/20 05.11.2020

Just like any decision in life, making financial choices would be a lot easier with the benefit of hindsight. Let’s talk about some of the things we might hear from people who wish they’d done things differently after looking in the rear view mirror. Show Notes & Info: Fleming FG Website:  https://www.flemingfg.com/ Free Webinar:  http://www.flemingfg.com/watch-ryan-pick-apart-a-pilots-401k

The Customer Isn’t Always Right 30.10.2020

Ryan checks in from Belgium as the election nears and coronavirus cases increase. And the lessons being learned right now relate well to that old saying in the retail world, “the customer is always right.” But when it comes to financial planning, it’s probably not wise to subscribe to that mentality 100 percent of the time. What’s the point of having a financial coach if your advice is better than...

Does The Presidential Election Matter To My Portfolio? 22.10.2020

This year's election is on the horizon and many people have strong emotions and opinions going into it. Emotions can take over during this time and cause people to make unwise financial decisions. Ryan discusses why we shouldn't sweat the upcoming election and the importance of recognizing recency bias. Show Notes & Info: Watch Ryan's Presentation: https://financeinsights.net/qdruw2VhxAm7TOJvYugne...

Life Advice From Those Who Have Lived Through Retirement 15.10.2020

This episode won’t be all about financial stuff. Sometimes it’s nice just to step back and listen to the experience of those who have come before us. We gathered some of the top life advice from those who have lived through most of their retirement already to see what we might be able to learn from their experiences. Show Notes & Info: Fleming FG Website:  https://www.flemingfg.com/ Free Webinar: ...

Eye Opening Stats Showing How Americans Save 08.10.2020

Vanguard’s “How America Saves 2020” report is packed with lots of intriguing stats and findings about Americans and how they save for retirement in the crazy year that is 2020 (most of the recent data is technically from 2019 although some figures are current through the Spring of 2020). Let’s look at some of the top takeaways from the study and how you might compare to the “normal” savings behavi...

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