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Passive Income Pilots

Tait Duryea and Ryan Gibson

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Weekly
 
Welcome to the Passive Income Pilots Podcast – the show designed to help pilots climb to new levels of financial success. Join Tait Duryea & Ryan Gibson, both airline pilots, business owners and investors, as they interview top experts and share practical knowledge on real estate, tax strategy, passive income and generational wealth. This one-of-a-kind show created specifically for professional pilots offers applicable strategies and tactics for improving your financial life. Whether you're ...
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A Wiser Retirement®

Wiser Wealth Management

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From retirement strategies to investing tips and financial planning guidance, our goal is to empower you with the knowledge you need to make smart financial decisions. Join us every week as we simplify complex financial topics, share real-life success stories, and guide you on your journey to financial freedom! A Wiser Retirement® Podcast is produced by Wiser Wealth Management, based in Marietta, Georgia. We specialize in Wealth Management and Flat Fee Financial Planning. To learn more about ...
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Welcome to the fascinating world of 'Trading Tomorrow - Navigating Trends in Capital Markets,' where finance, cutting-edge technology, and foresight intersect. In each episode, we embark on a journey to unravel the latest trends propelling the finance industry into the future. Join us as we dissect how technological advancements and market trends unite, shaping the strategies that businesses, investors, and financial experts rely on. From the inner workings of AI and ML to the transformative ...
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Pay or Quit

Shawn Austin Johnson

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Monthly
 
the podcast for entrepreneurs and business owners ready to face the raw truth of what it takes to succeed. Host Shawn Austin Johnson goes beyond polished success stories to explore the real, often messy, and challenging aspects of business ownership. This podcast is for those who feel isolated in their entrepreneurial journey, battle imposter syndrome, or face burnout. Shawn offers candid insights and isn't afraid to tackle tough conversations on what truly matters in business. Expect in-dep ...
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Most busy professionals, especially high-skilled, high-income earning first generation immigrants, tech professionals and doctors alike, are unaware of the ways of the ultra-wealthy in this country to grow, preserve, protect and pass the generational wealth. Think Outside the Stocks is a podcast focused on educating you to generate multiple streams of passive income, break out of wall street barrier, move towards financial freedom and a life of purpose and passion. Every week, your host Madh ...
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Curiosity alone won't change the world, but going Beyond Curious® will. The people that shape society are the explorers — the brave adventurers willing to take a voyage into the unknown to satisfy their curiosity, fulfill their purpose, and bring their ideas to life. This show is for those people. The ones that are relentlessly curious about themselves, their impact, their potential, the people they love, and the world around them. The ones who CONSTANTLY ask themselves, “What if…”, “I wonde ...
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The Pathless Path is hosted by Paul Millerd - a writer, creator, and consultant. He has conversations with freelancers, self-employed entrepreneurs, creators, and vagabonds who share their perspectives on their relationship with work, burnout, bootstrapping, indie hacking, remote work, reinvention, creativity, sabbaticals, leisure, self-employment, unconventional living, and digital nomadism. Past guests include Ali Abdaal, Russ Roberts, Kevin Kelly, Khe Hy, David Senra, Derek Sivers, Joe Hu ...
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In this episode of Trading Tomorrow – Navigating Trends in Capital Markets, host Jim Jockle speaks with Elemi Atigolo, Co-founder and Managing Partner of Consult Venture Partners, also known as ConsultVP, about the emergence of AI co-pilots in financial services. Atigolo outlines how AI co-pilots differ from general generative AI tools and describe…
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In this episode of A Wiser Retirement® Podcast, Casey Smith, President of Wiser Wealth Management and former airline pilot is with Grace Kennedy, Financial Planning Associate to discuss the unique financial needs of pilots and the smartest financial planning path for them. Airline pilots face a unique mix of high-but-variable income, mandatory reti…
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Today, I get to introduce you to someone who fundamentally helped create the personal development industry as we know it. In the 1970s, Marcia Martin was one of the original pioneers behind EST (now known as Landmark Forum). She was there during the very first 30-person seminar… and helped the organization grow to 800,000+ graduates, sparking a mov…
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Get the exact 5-step script that turned a broken sales process into an 80%+ conversion rate in under 90 days: https://game.findingpeak.com/masterclose/ Join our community of fearless leaders in search of unreasonable outcomes... Want to become a FEARLESS entrepreneur and leader? Go here: https://www.findingpeak.com Watch on YouTube: https://link.ry…
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In this episode of A Wiser Retirement® Podcast, Casey Smith, and Financial Advisor Michaela Dowdy dive into how retirement planning isn’t just about matching today’s income with today’s expenses. It’s about preparing for the future value of money. Related Podcast Episodes: Ep 245. Strategies for Early Retirement and Long-Term Security Ep 212. Medic…
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Get the exact 5-step script that turned a broken sales process into an 80%+ conversion rate in under 90 days: https://game.findingpeak.com/masterclose/ Join our community of fearless leaders in search of unreasonable outcomes... Want to become a FEARLESS entrepreneur and leader? Go here: https://www.findingpeak.com Watch on YouTube: https://link.ry…
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Why do so many high-earning pilots struggle to build real wealth? Hosts Tait Duryea and Ryan Gibson get candid about the habits, mindset, and blind spots that keep aviators from achieving true financial independence. They reveal the five biggest mistakes pilots make, from lifestyle creep and tax traps to ego-driven investing, and how to replace the…
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This episode explores the growing role of embedded finance in capital markets and beyond. We discuss how companies are approaching payments, lending, insurance, and investments, and examine the factors driving adoption across sectors and geographies. Guest Lars Markull, embedded finance consultant and founder of Embedded Finance Review, shares case…
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In this episode of the A Wiser Retirement® Podcast, Estate Planning Attorney Arun Gupta joins Shawna Theriault, CFP®, CPA, CDFA® to demystify trusts, what they are, who they’re for, and how 10 common trust types work in real life. Related Podcast Episodes: Ep 295: What Happens If You Die Without a Will? The Legal Nightmare Ep 279: What Should Paren…
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Replace your entire marketing stack with one powerful platform. Start your free GoHighLevel trial (no contracts) → https://link.ryanhanley.com/gohighlevel Download Free Inbound Sales Domination Workbook: https://game.findingpeak.com/masterclose/ Join our community of fearless leaders in search of unreasonable outcomes... Want to become a FEARLESS e…
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Open Banking Limited set the UK’s open banking standards, driving innovation and competition across retail banking. In this episode of Trading Tomorrow - Navigating Trends in Capital Markets, host Jim Jockle speaks with Nick Davey, their Head of Strategy, about how Open Banking Limited has developed, its successes for consumers and SMEs, and the ba…
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What do private placement memorandums really mean for you as an investor? Hosts Tait Duryea and Ryan Gibson sit down with attorney and real estate operator Seth Bradley to pull back the curtain on syndication documents, accreditation rules, and what truly protects investors. Seth shares his personal journey from med school to big law to entrepreneu…
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In this episode of A Wiser Retirement® Podcast, Casey Smith is joined by Robert Swarthout, CEO and Portfolio Manager of Teton Crypto Capital. Together, they dive into the latest crypto news, from the launch of new ETFs to the growing influence of stablecoins in U.S. Treasuries. The conversation explores how these developments could impact retiremen…
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Today’s episode is… a little strange. As the title suggests, I dissected an octopus. But don’t worry — no nine-brained, three-hearted, blue-blooded sea creatures were harmed in the making of this podcast 🐙. Instead, I brought back a dear friend and Curiosity Island citizen, Perry Knoppert — aka “Dr. Octopus” — the founder of the Octopus Movement, a…
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Stop paying $500/month for 8 different marketing tools. Try GoHighLevel's all-in-one platform free for 14 days → https://link.ryanhanley.com/gohighlevel Join our community of fearless leaders in search of unreasonable outcomes... Want to become a FEARLESS entrepreneur and leader? Go here: https://www.findingpeak.com Listen to Audio version: https:/…
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Send us a text From Combat Pilot to Gym Owner: Jason Santiago's Journey of Service and Entrepreneurship Join us in this episode of Pay or Quit as we sit down with Jason Santiago, a former Black Hawk helicopter pilot and military veteran, who has transformed his life from flying high-stakes missions to tackling the challenges of entrepreneurship and…
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In this episode of A Wiser Retirement® Podcast, Senior Financial Advisor Shawna Theriault, CFP®, CPA, CDFA® is joined by Financial Advisor William Medcalf, CFP® to discuss the financial implications of moving across state lines, and how a change in location can also mean major changes to your financial life. Related Podcast Episodes: - Ep 77: Tips …
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Agentic AI is moving from buzzword to experimentation in capital markets, but is it ready for large-scale adoption? In this episode of Trading Tomorrow – Navigating Trends in Capital Markets, host Jim Jockle speaks with Kieran Garvey, Head of AI Research at the University of Cambridge’s Centre for Alternative Finance, and Dr. Prateek Gupta, a postd…
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How protected is your wealth if something goes wrong? In this episode of Passive Income Pilots, Tait Duryea and Ryan Gibson sit down with asset protection expert Adam Kintigh to share practical strategies every pilot and high-income professional should know. From real estate privacy trusts that cut transfer taxes to Wyoming LLCs that safeguard synd…
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Join our community of fearless leaders in search of unreasonable outcomes... Want to become a FEARLESS entrepreneur and leader? Go here: https://www.findingpeak.com Watch on YouTube: https://link.ryanhanley.com/youtube TEDx Talk | "Stop Living a Life You Didn't Choose" - https://www.youtube.com/watch?v=9nWsxwgO83A The Influence Paradox: https://www…
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At 19, Anthony Englert thought he’d cracked the wealth code. He was living in a million-dollar mansion, cashing checks from a hedge fund with 12% monthly returns, and feeling on top of the world… …until his business partners accused him of not being willing to take enough risk, kicked him out of the company, and he lost everything — including his e…
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Join our community of fearless leaders in search of unreasonable outcomes... Want to become a FEARLESS entrepreneur and leader? Go here: https://www.findingpeak.com Listen to Audio version: https://linktr.ee/ryan_hanley Stop paying $500/month for 8 different marketing tools. Try GoHighLevel's all-in-one platform free for 14 days → https://link.ryan…
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In this episode of A Wiser Retirement® Podcast, Casey Smith and William Medcalf, CFP® dive into what it really means to be “quietly rich” and how smart habits, not flashy spending lay the foundation for financial independence. Related Podcast Episodes: - Ep 73: Leave a Legacy of Generosity - Ep 260: 10 Financial Habits That Lead to Long Term Succes…
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How do you reduce investor friction without dumbing down the experience? Podcast host, Jim Jockle, sits down with Eric Chu, CEO & Co-Founder, Tradesk Securities, to unpack how AI and behavioral UX can help time-pressed retail investors cut through noise, build better habits, and stay aligned to long-term goals. They dig into trust and transparency …
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What separates pilots who want to invest from those who actually succeed? In this episode, Tait Duryea and Ryan Gibson share the real stories behind their first deals, the mistakes they made, and the lessons that still guide them today. From disastrous single-family rentals to managing multifamily properties, they explain why failure is often the b…
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Join our community of fearless leaders in search of unreasonable outcomes... Want to become a FEARLESS entrepreneur and leader? Go here: https://www.findingpeak.com Watch on YouTube: https://link.ryanhanley.com/youtube Stop paying $500/month for 8 different marketing tools. Try GoHighLevel's all-in-one platform free for 14 days → https://link.ryanh…
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I’ll never forget my sophomore year of college, wandering the cobblestone streets of Sevilla, Spain, earbuds in… listening to something brand new to me at the time: Podcasts. One show in particular stood out: Entrepreneurs on Fire. Hearing real entrepreneurs talk about building businesses that made an impact felt revolutionary compared to the dry, …
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Send us a text Mastering Outbound Sales with Ben Smith In this episode, Shawn interviews Ben Smith, the founder of Bright Reach Sales, who has over seven years of experience in driving revenue through effective sales strategies. Ben shares his journey from insurance sales to founding Bright Reach, emphasizing the importance of outbound sales for bu…
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Join our community of fearless leaders in search of unreasonable outcomes... Want to become a FEARLESS entrepreneur and leader? Go here: https://www.findingpeak.com Watch on YouTube: https://link.ryanhanley.com/youtube Connect with Dr Brian Keating Into the Impossible Vol II: https://amzn.to/41StaXE Losing the Nobel Prize: https://amzn.to/4gpWNWq X…
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In this episode of A Wiser Retirement® Podcast, we discuss the importance of commercial airline pilot medical disability planning and why it’s often overlooked compared to life insurance. We explain how airline disability benefits work, the differences between short-term and long-term coverage, and why “own occupation” policies are essential. The c…
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Stop paying $500/month for 8 different marketing tools. Try GoHighLevel's all-in-one platform free for 14 days → https://link.ryanhanley.com/gohighlevel Join our community of fearless leaders in search of unreasonable outcomes... Want to become a FEARLESS entrepreneur and leader? Go here: https://www.findingpeak.com Watch on YouTube: https://link.r…
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Back in March, I hosted the first ever LIVE event for my community, Curiosity Island. We hired my friend and Curiosity Island “Castaway” Bob Regnerus to produce the video footage for our event: Click right here to watch the video Why am I sharing this with you? * Incoming humble brag * If you listen to that video, there was definitely a theme in wh…
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Click here to watch a video of this episode. Mentioned in the episode Andrew Taggart’s website Pathways to the Dao (Andrew’s Substack) Leisure: The Basis of Culture by Josef Pieper Secular Monks (article by Andrew Taggart) Why Buddhism is True by Robert Wright Pierre Hadot (Philosophy as a Way of Life) The Pathless Path by Paul Millerd (00:00) - In…
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Retirement isn’t just a finish line, it’s a brand new chapter. In this episode of A Wiser Retirement® Podcast, Casey Smith and Financial Advisor Michaela Dowdy outline eight key things you should focus on starting five years before retirement. While more time is always better, the 3–5 year mark is when many people get serious. Here's how to make th…
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I took questions from people for episode 200. Enjoy! Click here to watch a video of this episode. (00:00) - Introduction and Podcast Background (03:08) - Future of Education and Teaching (05:29) - Thoughts on Being a Prophet (06:09) - Current Pulling Forces and Changes (08:30) - Special Hardcover Edition Plans (10:05) - Managing Financial Anxiety (…
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In this episode of the A Wiser Retirement® Podcast, Casey Smith sits down with Robert Swarthout, founder and CEO of Teton Crypto Capital, to discuss how fast cryptocurrency is evolving and how banks are getting involved. - Ep 296: Crypto Update: Big Beautiful Bill, GENIUS Act, & Crypto Company IPOs - Ep 286: How can I evaluate crypto as a potential…
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Can oil and gas really be a smart play for high-income professionals? In this episode, Tait Duryea and Ryan Gibson sit down with Mark Fleming, petroleum engineer and Turbine Capital’s oil & gas advisor, to break it down. From the basics of how drilling works to the tax advantages that can offset W2 income, you’ll learn the realities of this often-m…
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Stop paying $500/month for 8 different marketing tools. Try GoHighLevel's all-in-one platform free for 14 days → https://link.ryanhanley.com/gohighlevel Join our community of fearless leaders in search of unreasonable outcomes... Want to become a FEARLESS entrepreneur and leader? Go here: https://www.findingpeak.com Watch on YouTube: https://link.r…
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Imagine this: You’re driving to a high-end coaching workshop—an event you’ve just spent a big chunk of money to attend. You’re hopeful, nervous, not totally sure if you even should be going… And then, mid-drive, you get into one final painful conversation with your mother—and decide, in that moment, to end the relationship. This was a pivotal momen…
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In this episode of A Wiser Retirement® Podcast, we celebrate hitting a major milestone, 300 episodes! In this special episode, President Casey Smith and Senior Financial Advisor Shawna Theriault, CFP®, CPA, CDFA®, reflect on the history of Wiser Wealth Management, the growth of the podcast, and the firm’s mission to provide real, relationship-drive…
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Join our community of fearless leaders in search of unreasonable outcomes... Want to become a FEARLESS entrepreneur and leader? Go here: https://www.findingpeak.com Watch on YouTube: https://link.ryanhanley.com/youtube Connect with Natalyn Lewis Website: https://nattyo.com/ Instagram: https://www.instagram.com/natty.o.lewis Performance coach Nataly…
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Tait Duryea and Ryan Gibson welcome Mat Sorensen, CEO of Directed IRA, for a powerful discussion on how pilots and high-income professionals can unlock private investment opportunities through retirement accounts. From self-directed IRAs to Solo Ks, Mat explains the mechanics of rolling over old 401(k)s, navigating recent regulatory changes, and ta…
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Join our community of fearless leaders in search of unreasonable outcomes... Want to become a FEARLESS entrepreneur and leader? Go here: https://www.findingpeak.com Watch on YouTube: https://link.ryanhanley.com/youtube Hanley reflects on his recent trip to Greenville, South Carolina, where he attended Mick Hunt's Lead Loud series leadership event. …
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One of my core values is something I call conscious storytelling. I believe the stories we tell — both internally to ourselves and externally to the world — create our reality. Change your story, and you can change your reality. That’s why in this Beyond Curious Time Machine episode, I wanted to hit both sides of storytelling: How do we tell more m…
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In this episode, I talk with Dennis Owen about his journey from a long career in the airline industry to building a purposeful and active retirement in Chiang Mai, Thailand. Dennis shares how he intentionally “retired to” a new life filled with volunteering, consulting, and community involvement, rather than just leaving work behind. We discuss the…
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In this episode of A Wiser Retirement® Podcast, Shawna Theriault, CFP®, CPA, CDFA® and Financial Advisor Michaela Dowdy dive into the essential financial conversations couples should have before saying “I do.” From discussing mindsets and money habits to navigating joint goals and future planning, they offer guidance on how to build a healthy finan…
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