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The Pilot’s Advisor Podcast
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The Pilot’s Advisor Podcast

Author: Ryan Fleming

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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. We’ll teach both pilots and non-pilots what it takes to have a successful financial future. The Pilot’s Advisor Podcast® will answer your questions about 401(k)s, IRAs, taxes in retirement, long term care needs and much more.
133 Episodes
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Every generation likes to talk about how much harder things used to be when they were kids. Like all of the people who used to have to walk five miles to school, in the snow, uphill both ways. But they had at least one thing that was EASIER…and that was retirement planning.   Here’s what we cover in this episode: 0:00 – Intro 2:21 – Change from generation to generation 3:30 – Company loyalty 4:51 – Housing market 6:30 – Reliance on personal savings 8:58 – Investment options 10:07 – Interest rates 15:03 – Healthcare costs 18:00 – Sandwich generation 24:11 – Education   Retire Pilots - https://retirepilots.com   Get your FREE Retirement Toolkit - https://bit.ly/3ZmZsaX   Pilot Tax - https://pilot-tax.com/   The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2
Are you planning for your retirement with the confidence that you're making all the right moves? In today's episode, we'll unveil the crucial income planning mistakes that could jeopardize your retirement. Tune in to ensure your retirement strategy is foolproof against common pitfalls and ready to secure your financial future.   Here’s what we cover in this episode:   0:00 – Intro 4:38 – Planning to be retired for years instead of decades 6:39 – Starting Social Security too early 11:59 – Assuming bonds will be your main source of income 14:06 – Ignoring the impact of inflation 17:19 – Forgetting to create lifetime income streams outside of Social Security 17:19 – Failing to review and adjust your plan regularly   Retire Pilots - https://retirepilots.com   Get your FREE Retirement Toolkit - https://bit.ly/3ZmZsaX   Pilot Tax - https://pilot-tax.com/   The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2
Being a better investor doesn’t require you to spend hours and hours researching the latest trends and market data. The most important change people can make is taking emotions out of their decision-making. It’s much easier said than done, which is why we see people make these same emotional mistakes time and time again.   We’re excited to bring on Lee Hyder of Lee Hyder & Associates today to discuss this common challenge that pilots and other investors face when managing their finances. Why do we repeat these mistakes and what can we do to remove emotions from our investing? We’ll explore that in this video and provide you with some guidance on how to overcome this emotional pitfall.   Here’s some of what we discuss in this episode: 0:00 – Intro 0:22 – Emotional investing 2:32 – Being active doesn’t mean more success 6:30 – Advice for pilots 9:00 – Watching someone make mistakes   Retire Pilots - https://retirepilots.com   Get your FREE Retirement Toolkit - https://bit.ly/3ZmZsaX   Pilot Tax - https://pilot-tax.com/   The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2
Today we’re going to catch up with Coach Fedora to reflect on a successful career in the sport. We want to hear some of his best stories about Air Force and other stops, but we’ll also talk about life off the field as well. From a social media picture that went viral to a weightlifting scare, this show will cover a lot of ground with someone we respect highly. Plus, we’ll get his opinion on the state of college football and whether he’s happy to be enjoying retirement rather than being back on the grind in this new landscape.   Here’s what we cover in this episode: 0:00 – Intro 0:50 – Championship team at Air Force 4:34 – Position coach vs Head coach 7:45 – Demar Dotson story 10:26 – Managing different personalities 12:46 – Differences coaching at Air Force 14:09 – Favorite recruiting stories 16:36 – Enjoying retirement 21:02 – Social media photo 22:53 – How he met his wife 27:10 – Handling adversity 30:21 – Turning 60 and the workout accident 36:05 – Where he draws motivation from 40:39 – Meeting Michael Jordan 46:12 – Red Bull 48:14 – Current landscape of college football   Retire Pilots - https://retirepilots.com   Get your FREE Retirement Toolkit - https://bit.ly/3ZmZsaX   Pilot Tax - https://pilot-tax.com/   The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2
Delta paid out a large profit-sharing bonus this month, which is great for those pilots who received a check on Valentine’s Day. The question we get a lot when these bonuses get paid is what should you be doing with it? We wanted to shoot this short video to provide some general guidance for pilots who have some extra money to invest or save. It might not be specific advice but it should give you some ideas for how you’ll use the bonus. We’d love to talk to you more about your investment strategies if you have additional questions.   Retire Pilots - https://retirepilots.com   Get your FREE Retirement Toolkit - https://bit.ly/3ZmZsaX   Pilot Tax - https://pilot-tax.com/   The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2
We’re excited to bring on Lee Hyder of Lee Hyder & Associates today to share insights and stories from 30+ years of experience. Join us as we go back and forth on the highs and lows investors face, underscoring the need for resilience and a long-term outlook when building a portfolio for retirement. We spend the first part of the how discussing fees and how you should approach them with your investment portfolio. Who wouldn’t pay a percent or two to get an extra three or four percent return? That’s part of what you should be evaluating and we’ll get Lee’s insight on how he evaluates investments for clients. Plus, let’s take a look at the S&P 500 and why it isn’t the way to get true diversification in your portfolio.   Here’s some of what we discuss in this episode: 0:00 – Intro 0:49 – Howard Capital portfolios 7:21 – S&P 500 10:33 – Educating pilots   12:27 – Distribution phase 14:23 – Final wisdom from Lee   Retire Pilots - https://retirepilots.com   Get your FREE Retirement Toolkit - https://bit.ly/3ZmZsaX   Pilot Tax - https://pilot-tax.com/   The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2  
Everyone wants to know. Will the economy boom or bust in 2024? Join us as we explore a range of expert predictions, from the shifting trends in housing prices to the looming question of a potential recession or stock market crash. We'll balance our discussion with both optimistic and pessimistic perspectives from an array of sources to give you a comprehensive view. Ryan will also weigh in with his own perspective on each of the financial topics so tune in to navigate the uncertainties and opportunities of 2024's economic landscape and equip yourself with knowledge for the year ahead.   Here’s some of what we discuss in this episode: 0:00 – Intro 2:55 – The stock market in 2024 13:04 – The economy in 2024 15:32 – Housing in 2024 Retire Pilots - https://retirepilots.com   Get your FREE Retirement Toolkit - https://bit.ly/3ZmZsaX   Pilot Tax - https://pilot-tax.com/   The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2
We’re excited to bring on Lee Hyder of Lee Hyder & Associates today to share insights and stories from 30+ years of experience. Join us as we go back and forth on the highs and lows investors face, underscoring the need for resilience and a long-term outlook.   Here’s some of what we discuss in this episode: 0:00 – Intro 2:41 – Keeping up with change in the industry 4:07 – Using technology to trade 6:58 – Returns 13:26 – Managing expectations 16:56 – Greed vs Fear   About our guest: https://www.leehyder.com/    Retire Pilots - https://retirepilots.com   Get your FREE Retirement Toolkit - https://bit.ly/3ZmZsaX   Pilot Tax - https://pilot-tax.com/   The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2
This episode is going to delve into the significant new Tentative Agreement for Southwest Airlines pilots and break it all down so you know the most important details. By the end of the show, you should be up-to-date on the impact and the implications of the TA. We’ve invited Captain Robert Ecklund of Southwest Airlines to talk about some of the key aspects of the contract that's coming out, including compensation, disability benefits, retirement plans, and the implementation schedule. We’ll focus on some of the intricacies of the cash balance plan, the exceptional disability benefits and that compensation increase. Stay tuned after our conversation with Rob because we’ll bring on Zach Smith, Managing Partner, CPA to dive into all the tax details so you’ll have a better idea of what this could mean on your bottom line.   Here’s some of what we discuss in this episode: 0:00 – Intro 1:45 – Guest intro 5:36 – Overview of the TA 7:03 – Cash balance plan 11:35 – Changes in disability 17:30 – Company contributions 21:55 – Tax rates 26:22 – Compensation details 33:30 – TA Tax implications with Zach Smith from Pilot-Tax   Connect with Pilot-Tax: https://pilot-tax.com/   Retire Pilots - https://retirepilots.com   Get your FREE Retirement Toolkit - https://bit.ly/3ZmZsaX   Pilot Tax - https://pilot-tax.com/   The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2
Sometimes it’s hard to make financial sacrifices when the reward might not be seen until several years in the future, but the idea of delayed gratification is at the core of retirement planning. In this episode we’ll talk about some of the situations where you might be inclined to take the immediate benefit when you should really consider the delayed rewards.    Here’s some of what we discuss in this episode: 0:00 – Intro 3:55 – A lesson instilled 4:32 – Passing up the company match 7:01 – Saving in tax-deferred accounts 9:33 – Emergency fund 11:55 – Pulling out of retirement account early 15:15 – Home maintenance and upgrades 17:38 – Social Security 20:36 – Health check-ups 23:16 – Working with an advisor   Retire Pilots - https://retirepilots.com   Get your FREE Retirement Toolkit - https://bit.ly/3ZmZsaX   Pilot Tax - https://pilot-tax.com/   The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2
The goal for the show today is to provide you with a broad picture of being offered and share some things from our research that Delta pilots should be aware of and think through. Plus, we’ll offer some alternative options to this GVUL policy for pilots looking for a safe asset. If you’re just looking for a quick cliff notes version of what we discuss, skip to the final few minutes to hear us summarize all of our thoughts.   Also, make sure you check out this sequence of returns explanation Ryan recorded to understand this risk: https://www.youtube.com/watch?v=vSsR7Km5XRw   Here’s some of what we discuss in this episode: 0:00 – Intro 2:15 – What is this new policy and what is it replacing? 4:50 – The difference between term life and permanent life? 7:38 – 3 reasons why a Delta pilot might want to do this. 12:42 – The cons for this specific GVUL option that you need to be aware of. 21:52 – What could cause a policy like this blow up? 23:59 – Alternative options 33:02 – Structuring the policy for someone that isn’t concerned about the death benefit.   Retire Pilots - https://retirepilots.com   Get your FREE Retirement Toolkit - https://bit.ly/3ZmZsaX   Pilot Tax - https://pilot-tax.com/   The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2
The idea we’ve been exposed to about investing is that our money can only be in one place at a time, right? That’s all we’ve ever heard, but that’s not exactly true. Your money can work for you in two different places thanks to the Infinite Banking Concept. It’s a strategy that we’ve previously discussed with today’s guest, Dave Befort, but today we want to dive into how to truly harness the power of being your own bank.   Here’s some of what we discuss in this episode: 0:00 – Intro 4:24 – The Infinite Banking Concept 7:59 – Why Dave does this   14:45 – The amount the average person pays towards debt 18:52 – Using this vehicle to replace a Roth 21:46 – Having access to your money 25:13 – Why should a pilot consider this? 32:49 – Why Ryan won’t invest in any fixed income again 35:57 – How do you get to a point where you’re putting all your money in here?   Learn more about Dave: https://maxperformancefinancial.com/about/ Read ‘Becoming Your Own Banker’ by Nelson Nash: https://www.amazon.com/Becoming-Your-Own-Banker-Infinite/dp/B001NZO1DS   Resources for Pilots: Retire Pilots - https://retirepilots.com Get your FREE Retirement Toolkit - https://bit.ly/3ZmZsaX Pilot Tax - https://pilot-tax.com/ The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2
Many of the FedEx and UPS pilots still have a pension and they often ask what to do about the survivor benefits. Many of them are inclined to lean towards the 50% survivor benefit, but that’s not typically the best option. To help us explore some of these other options, we’ve invited Dave Befort onto the podcast today. He’s an expert in the Infinite Banking Concept for pilots as well as many other aspects of retirement, and we’re going to talk today about different survivor benefit options and how they play into your overall retirement strategy. Dave believes strongly in using life insurance to help you control your money and he’ll explain some of these strategies in this video. #pilotlife #infinitebanking #survivorbenefits   Here are some of the highlights from this episode: 0:00 – Intro 2:06 – The math behind the 50% survivor benefit 6:02 – The questions you need to be asking 12:02 – Another option: permanent life insurance 19:35 – The benefits of the Infinite Banking Concept 22:49 – Tax strategies 29:24 – Sequence of return risk   Learn more about Dave: https://maxperformancefinancial.com/about/   Retire Pilots - https://retirepilots.com Get your FREE Retirement Toolkit - https://bit.ly/3ZmZsaX Pilot Tax - https://pilot-tax.com/ The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2
We’ve talked about it some already on the show, but the South Carolina Coaches for Charity event has become a passion of ours. The money raised goes to help some outstanding charities, including the Fisher DeBerry Foundation started by Ryan’s former head coach. Our goal for the 2023 event was to pour our time and effort into helping the organizers continue to grow the event and build on the success they’ve already seen. To help us do that, we brought in Steve Sharp of Sharp Digital Marketing. He’s the man behind everything we do at The Pilot’s Advisor and his expertise made a huge impact on results for this year’s Coaches for Charity event.  We spent a little time with Steve after the event to talk more about what we were able to do and what we thought about the way everything turned out. Plus, we wanted to introduce him so you could learn more about someone who has been a big part of our growth here on the show.  Here are some of the highlights from this episode:  0:00 – Intro 3:11 – Background on South Carolina Coaches for Charity 8:08 – Feeling of being a part of a team again  13:26 – The kids meeting Steve 17:01 – The work Steve did with the coaches' event  21:40 – The Community MVP we honored 24:45 – An emotional night for Coach DeBerry   Learn more about Steve: https://sharpdigitalmarketing.com/    Learn more about Coaches for Charity: https://southcarolinacoaches.com/  --------------------------------------------------------------------------------------------------------- Retire Pilots - https://retirepilots.com Get your FREE Retirement Toolkit - https://bit.ly/3ZmZsaX Pilot Tax - https://pilot-tax.com/ The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2  
Imagine being addicted to meth and leading an organized crime ring, only to be arrested and sentenced to life in prison. That was the reality for our guest today, the best-selling author and motivational speaker Damon West. His story of transformation is unlike any other, filled with tales of resilience, hope, and a unique perspective on life that only prison walls could provide. He went from being a college quarterback with a bright professional future in business to a life sentence in a matter of years. But a prison mentor named Mr. Jackson changed his life with the coffee bean message. We met Damon during the South Carolina Coaches for Charity event this summer and were blown away by his remarkable story. That’s why we wanted to bring it hear and share it with you. Since leaving prison in 2015, he’s spoken to college football teams like Clemson, Alabama, Oklahoma and expanded in a way that requires him to travel 24 days out of each month. His life-altering insights are a testament to the power of change, and the strength of the human spirit to rise above adversity and we’re excited to share that with you today.   Here are some of the highlights from this episode: 0:00 – Intro 1:50 – His life of drugs and crime 15 years ago 3:47 – How ‘be a coffee bean’ started 8:09 – Success since being paroled 12:41 – His first encounter with Dabo Swinney 17:42 – Talking to the Clemson football team 19:24 – How the coffee bean message exploded   Learn more about Damon: https://damonwest.org/ Check out some of his appearances here: https://damonwest.org/resources/ South Carolina Coaches for Charity: https://bit.ly/3Ro0Dog   Resources: Retire Pilots - https://retirepilots.com Get your FREE Retirement Toolkit - https://bit.ly/3ZmZsaX Pilot Tax - https://pilot-tax.com/ The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2    
In this episode, we construct a helpful conversation about the role of real estate in a retirement strategy, exploring everything from rental income to reverse mortgages. Whether you're a pre-retiree with a portfolio of properties or just curious about leveraging your home equity, this discussion offers thoughtful insights for anyone navigating the crossroads of real estate and retirement.   Home Equity Video: https://vimeo.com/848469893   Show Notes & Info: Retire Pilots Website - https://retirepilots.com/ Retirement Toolkit - https://retirepilots.com/toolkit-2/ Pilot Tax - https://pilot-tax.com/
Are you nearing “retirement age”? If so, let’s explore that pivotal question you’ll soon face: Should you retire or continue working? We’ll unravel the intricacies of this decision, addressing both financial and emotional aspects, and help you find out if you’re truly ready to retire.   Show Notes & Info: Retire Pilots Website - https://retirepilots.com/ Retirement Toolkit - https://retirepilots.com/toolkit-2/ Pilot Tax - https://pilot-tax.com/
Legendary football coach Fisher DeBerry joins Ryan to discuss the South Carolina Coaches for Charity Event. This year might be the biggest event yet. Listen to learn about their mission. You can also learn more online at https://southcarolinacoaches.com and if you're nearby, consider attending the annual gala on Monday, July 17, 2023.   Show Notes & Info: Retire Pilots Website - https://retirepilots.com/ Retirement Toolkit - https://retirepilots.com/toolkit-2/ Pilot Tax - https://pilot-tax.com/
Are you a golfer? Even if you're not, the game of golf can teach us valuable lessons about retirement planning. For example, hitting a hole-in-one might be thrilling, but it won't necessarily guarantee your overall success. And just like you need different clubs in your golf bag to play a round, you need a well-balanced approach to your investments in retirement. But perhaps the most important lesson from golf is the value of having a caddy. In retirement planning, a financial advisor can help you navigate the hazards and make the most of your financial "clubs." Tune in to this episode to learn more about how the game of golf can help you plan for a successful retirement. Here's a link to the "golf" Dude Perfect battle video we mention during the show: https://www.youtube.com/watch?v=heIKaaamvdc   Show Notes & Info: Retire Pilots Website - https://retirepilots.com/ Retirement Toolkit - https://retirepilots.com/toolkit-2/ Pilot Tax - https://pilot-tax.com/
Today we are joined by Dave Befort, CEO of Max Performance Financial and IBC practitioner. In this episode, Dave will explain how utilizing IBC can enhance retirement planning by eliminating the risk associated with a sequence of returns and offering a volatility buffer. Learn how borrowing tax-free income from the insurance policy can protect your retirement portfolio during market downturns, the advantages of building a tax-free jet engine for retirement, and the flexibility it provides in controlling your tax bracket.   Show Notes & Info: Retire Pilots Website - https://retirepilots.com/ Retirement Toolkit - https://retirepilots.com/toolkit-2/ Pilot Tax - https://pilot-tax.com/
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