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Passive Income Pilots

Tait Duryea and Ryan Gibson

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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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AI & I

Dan Shipper

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Learn how the smartest people in the world are using AI to think, create, and relate. Each week I interview founders, filmmakers, writers, investors, and others about how they use AI tools like ChatGPT, Claude, and Midjourney in their work and in their lives. We screen-share through their historical chats and then experiment with AI live on the show. Join us to discover how AI is changing how we think about our world—and ourselves. For more essays, interviews, and experiments at the forefron ...
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Welcome back to Passive Income Pilots! In this special "Friday for Flyers" episode, we're diving into a critical topic for every pilot – medical certifications and aeromedical issues. Today, we have the honor of hosting Dr. Dan Monlux, an experienced AME, former F-18 pilot, and founder of Wingman Med. Dr. Monlux brings a wealth of knowledge and exp…
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Welcome to another exciting episode of Passive Income Pilots! We're diving into a fascinating and often overlooked passive income stream: vending machines. Our guest, Mike Hoffmann, also known as "Mr. Passive," shares his journey of creating a vending machine empire and how this low-barrier investment can yield significant returns. Whether you're a…
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In this episode we welcome special guest Alex Racey, a renowned personal performance coach with an extensive background in the military. The discussion focuses on the importance of maintaining physical and mental health, particularly for aviators, frequent flyers, and professionals who sit for long periods. Alex Racey, who served 25 years in the U.…
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Claire Vo built ChatPRD—an on-demand chief product officer powered by AI. It’s now used by over 10,000 product managers and is pulling in six figures in revenue. The best part? Claire has a demanding day job as the CPO at LaunchDarkly. So she built all of ChatPRD herself—over the weekend—with AI. I sat down with Claire to talk about how ChatPRD wor…
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Welcome back to another episode of Passive Income Pilots! In this episode, Tait Duryea and Ryan Gibson sit down with Nick Friedman, co-founder of College Hunks Hauling Junk, who appeared on the pilot episode of Shark Tank. Nick shares his journey from starting a small moving and junk removal business in college to building a multi-million dollar fr…
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An interview with best-selling sci-fi novelist Robin Sloan One of my favorite fiction writers, New York Times best-selling author Robin Sloan, just wrote the first novel I’ve seen that’s inspired by LLMs. The book is called Moonbound, and Robin originally wanted to write it with language models. He tried doing this in 2016 with a rudimentary model …
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In this special episode, we have the honor of flying with Keith Rosenkranz, the legendary Delta Captain who chartered his own retirement flight. Keith's incredible story has captivated the aviation community, and today, he shares the details of his epic farewell flight, his career journey, and his strategies for building a financially secure retire…
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We use it to find bestselling author Steven Berlin Johnson’s next project. I sat down with bestselling author Steven Johnson to see if we could come up with a concept for his next project—using AI. The results were amazing. We loaded 200,000 words of NASA transcripts and all of Steven’s reading notes since 1999 into NotebookLM, Google’s personalize…
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Learn how the smartest people in the world are using AI to think, create, and relate. Each week I interview founders, filmmakers, writers, investors, and others about how they use AI tools like ChatGPT, Claude, and Midjourney in their work and in their lives. We screen-share through their historical chats and then experiment with AI live on the sho…
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Welcome back to Passive Income Pilots, where we dive into the intersection of aviation, finance, and personal success. Today, we have a special treat for both football enthusiasts and aspiring investors. Our guest is none other than Seattle Seahawk NFL Defensive Legend and Super Bowl Champion, Cliff Avril. Known for his ferocious defense and countl…
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Welcome to another episode of Passive Income Pilots! This week, your hosts Tait Duryea and Ryan Gibson are thrilled to bring you an insightful conversation with private equity mogul Collin Hathaway of Skylight Capital, a seasoned entrepreneur specializing in business acquisitions. In this episode Collin shares his journey from buying his first plum…
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New York Times journalist Kevin Roose has 18 new friends—none of whom are human. Kevin formed a collection of “friends”—AI personas with distinct personalities and backstories—using apps like Kindroid and Nomi. Among these were fitness guru Jared, San Francisco-based therapist Peter, and pragmatic trial lawyer Anna. He talked to them every day for …
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Welcome to another episode of Passive Income Pilots, where we delve into the burgeoning world of assisted living investments. Join hosts Tate Duryea and Ryan Gibson as they discuss the impact of the demographic shift known as the "Silver Tsunami" with Dwayne Clark, founder of Aegis Living. Dwayne shares his extensive experience in building a premie…
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Welcome back to Passive Income Pilots! In this episode we delve into essential tax strategies tailored specifically for pilots. With the expertise of Toby Mathis from Anderson Advisors, we explore five key ways you can reduce your tax liability effectively. Toby brings his depth of tax knowledge directly to our pilot audience, discussing everything…
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Nick Dobos, maker of the #1 programming GPT, on prompt-gramming with AI You can go from having an idea to deploying a live website in minutes. All you have to do is prompt Grimoire, the number-one custom GPT for programming, with an image or even a single word about your idea. As you watch the LLM process your request, Grimoire works with a web hos…
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Welcome to another thrilling episode of Passive Income Pilots, where we navigate the high-flying world of passive income opportunities. Today, we're joined by Joe Fairless, a titan in real estate investment and co-founder of Ashcroft Capital. Joe is renowned for his groundbreaking "Best Ever" conference, which is exactly where our hosts first cross…
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The future of AI technology isn’t just faster or more powerful—it’s empathetic. My guest for this episode, Alan Cowen, is leading the charge with the first-ever emotionally intelligent AI. Alan is the co-founder and CEO of Hume, an AI research laboratory developing models trained to identify and measure expressions of emotion from voice inflections…
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In this thought-provoking episode of Passive Income Pilots, we sit down with blockchain expert Hans Koning to navigate the complexities and opportunities within the blockchain landscape, especially in light of recent global events like the Bitcoin halving and rising geopolitical tensions. Hans shares his profound insights into how these factors inf…
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Learn how to use philosophy to run your business more effectively Reid Hoffman thinks a masters in philosophy will help you run your business better than an MBA. Reid is the cofounder of LinkedIn, a partner at venture capital firm Greylock Partners, the host of the Masters of Scale podcast, and a prolific author. But before he did any of these thin…
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Ever wonder how to turn your entrepreneurial dreams into reality? Tune into our latest episode of Passive Income Pilots as we soar into the world of angel investing and marketplace innovation with Nick Huzar, the CEO and founder of OfferUp! Discover how Nick's room full of unwanted items sparked the vision for a multi-billion-dollar company that re…
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Seth-Stephens Davidowitz wrote a book in 30 days—and he did it with ChatGPT. Seth is a data scientist, economist, and author who challenged himself to write a book—Who Makes the NBA?—in less than 1 month after realizing how fast he could work by using ChatGPT plugin Advanced Data Analysis. But along the way he discovered something else: Writing wit…
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Join us in this insightful episode of Passive Income Pilots as we explore the multifaceted world of real estate with Leka Devatha. From her early beginnings to overcoming the inherent challenges of the industry, Leka shares her journey of resilience, intuition, and strategic diversification. Discover actionable insights and inspiration whether you’…
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In today's episode hosts Tait Duryea and Ryan Gibson navigate through the vast skies of real estate investing with the guidance of real estate titan, Kathy Fettke. As a renowned expert and a beacon of knowledge in real estate and economics, Kathy brings invaluable insights into the current real estate market, investment strategies, and the future o…
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Unlock the potential of 1031 exchanges with Kyle Williams, Senior VP at Velocity 1031, on this enlightening episode of Passive Income Pilots. Designed for aviators aiming to navigate the complex skies of real estate investment, this discussion sheds light on tax deferral strategies that can significantly impact your financial trajectory. Whether yo…
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Nicholas Thorne is building Squarespace for the AI age. It’s called Audos, and it’s an AI chatbot to help any entrepreneur go from idea to: - Pitch deck - Working website - Custom GPT - User interviews with real customers All in just a few minutes. And he did it using ChatGPTapp. It’s AI all the way down—and it’s one of the most impressive AI busin…
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Antidepressants changed my life. I have OCD and antidepressants did what nearly a decade of therapy, meditation, and supplements couldn’t: they allowed me to live my life without being in a 24/7 spiral. (Bonus: they actually made therapy and meditation far more helpful once they started to work.) I think antidepressants are seriously misunderstood.…
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You can build and run a one-person internet business that earns half a million in annual revenue—with AI. Ben Tossell showed me exactly how in this episode. Ben is the founder of Ben’s Bites—one of the best daily AI newsletters out there, which I love reading every day—and an investor in a number of promising early-stage AI startups. Ben is also an…
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Join hosts Tait Duryea and Ryan Gibson on Passive Income Pilots as they engage in a profound conversation with Joe LoRusso, aviation law expert and Director of Aviation at Ramos Law. This episode takes an earnest look into pilot mental health and legal challenges, spotlighting the systemic issues and proposing a transformative approach to aviation …
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I made the greatest trade of my life with Jesse Beyroutey in 2019. We bought Nvidia shares when they were trading at $33. They’re worth nearly $800 today. I sat down with Jesse to top that trade in 90 minutes using Gemini Pro 1.5’s incredible 1 million token context window—and make a $1,000 trade live on the show. Jesse is a managing partner at IA …
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You can break into Hollywood with a movie you made alone in your room without using a single camera. Dave Clark showed me how live on this show. Dave Clark is a film director and commercial director with experience working with brands like HP and Intel who is now experimenting with cutting-edge AI technology. He recently produced a popular sci-fi s…
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Are you a curious person with a lot of ideas and little time? Anne-Laure Le Cunff can show you how to do it all. Anne-Laure is the founder of one of my favorite internet communities for curious minds, Ness Labs, a prolific writer, and a neuroscience PhD candidate. She’s also writing a book, Liminal Minds, that’ll be out later this year. And she sai…
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The next big idea is hiding in plain sight. It’s right here, scattered across the internet in incoherent fragments. Steph Smith, my guest for this episode, knows how to connect the dots. Steph Smith is a prolific online creator, host of the a16Z podcast, author of a book about building a successful blog called Doing Content Right, and creator of In…
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On this episode of Passive Income Pilots, Tait and Ryan interview David Phelps. Dr. David Phelps, founder of Freedom Founders, spent 27 years as a former general dentist and business owner. His life took a significant turn when his daughter Jenna faced leukemia. This personal crisis prompted Dr. Phelps to reassess his priorities and shift his focus…
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You can make a video game without writing a single line of code. Logan Kilpatrick uses ChatGPT to show me how. Logan is OpenAI’s first developer relations and advocacy hire. A big part of Logan’s job is supporting the community of builders using ChatGPT, DALL-E, and the OpenAI API. He’s also deeply invested in growing this community, convinced that…
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Dr. Gena Gorlin (https://twitter.com/Gena_I_Gorlin) is a clinical psychologist at UT Austin whose goal is to raise the ceiling on human potential. I sat down with her to discuss how ChatGPT has become a key tool in her quest for radical self-betterment. In this episode, she feeds ChatGPT a list of her old journal entries, and it conducts the most t…
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Today on Passive Income Pilots is Tait & Ryan's one-on-one episode. In this episode, Tait and Ryan reflect on past episodes and share insights on their favorites. Whether you're new to the show and would like to “catch up”, or a long time listener who could use a second listen to our most impactful episodes, this episode serves as a recap and calls…
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Tyler Cowen is an economist who has been thinking about the impact of technology on life, work, and the economy for the past decade. He is a prolific writer behind the leading economic blog Marginal Revolution, a professor of economics at George Mason University, and the author of 17 books. In this episode, I dive deep with him on how ChatGPT will …
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Today on Passive Income Pilots is Tait & Ryan's one-on-one episode. Tait and Ryan peel back the curtain on personal goal setting that actually works. This episode isn't about the fluff but the nitty-gritty of mapping out a future that aligns with your deepest ambitions in family, business, and investing. We're talking about effective goal-setting, …
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David Perell is one of the best known internet writers of his generation. He’s amassed almost a half million followers on X, hosts the popular podcast How I Write, and founded Write of Passage, which has taught thousands of students how to be digital writers. We go deep on using ChatGPT to: Doing deep reading of old books Finding anecdotes that spr…
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This show might be a first in the history of podcasts: Researcher ⁠Geoffrey Litt⁠ and I built an app together using ChatGPTapp and Replit in under 60 minutes—while we talked. We wanted to show how AI and ChatGPT change who gets to build software and how they usher in a world where everyone can ⁠modify⁠ and ⁠remix⁠ the apps they use every day. So we…
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On this episode of Passive Income Pilots, Tait and Ryan interview Christian Allen and Rod Zabriskie. Christian Allen and Rod Zabriskie from Money Insights Group join Tait in a riveting discussion about stepping off the beaten path of traditional investing and venturing into the world of max-funded cash value life insurance and real estate. They ill…
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Sometimes ChatGPT is a copilot, sitting beside you, taking directions, and guiding you as you fly through your work. At other times, it’s a subordinate. It’s not just an assistant or a companion, but a trusted deputy, someone—or something—that’ll heed instructions and complete tasks. This is how our guest, Nathan Labenz, thinks about ChatGPT. In th…
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On this episode of Passive Income Pilots, Tait and Ryan interview Derreck Long. Derreck Long, a former Senior IRA Specialist at Quest Trust Company, recently joined Eckard Enterprises. Eckard Enterprises is a family-owned and operated alternative investment and asset management firm specializing in the U.S. oil and gas industry. Derreck became a Se…
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TL;DR: Today we’re releasing a new episode of our podcast How Do You Use ChatGPT? I go in-depth with Notion research engineer Linus Lee on how he uses ChatGPT and Notion AI to maximize creative control. Watch on X, YouTube, or Spotify. You might think that being an AI researcher would mostly involve solving complicated programming problems and thin…
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On this episode of Passive Income Pilots, Tait and Ryan interview Alan Underwood. Momentum Capital Group co-founder Alan Underwood is a successful entrepreneur who found passive income in real estate after working in numerous businesses. Alan discusses his experience attending meetups, flipping properties, and developing a 90+ unit Arizona apartmen…
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In this week’s episode of the Passive Income Pilots, Ryan and Tait take on another one-on-one conversation. They discuss various year-end tax strategies to maximize deductions and reduce tax liability. They also explore the short-term rental loophole as a tax strategy and discuss the benefits of cost segregation studies and bonus depreciation. Tait…
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How Nat Eliason uses ChatGPT to write books:Nat Eliason is a shape-shifter.He’s a writer with a book deal from Random House, a crypto trader, a Roam Research aficionado, a marketer, a book podcaster, a parent, and a seed oil iconoclast. He's amassed thousands of newsletter subscribers, 70,000 followers on X, and 110,000 on TikTok. His secret weapon…
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About the show I believe that ChatGPT is the most important creative tool of the decade. I think it can help us write better, create art, efficiently ship products, build great businesses, make smart decisions, and even learn something about ourselves,. But it’s still so early. Most of us don’t even really know how to use ChatGPT. We have a feeling…
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Welcome back to another episode! Tait and Ryan talk about the lucrative world of commercial real estate investments, with a special focus on self-storage, a rising asset class rapidly gaining traction among investors. They discuss cap rates, why building is better than buying in the current market, underwriting self-storage, and rent growth. Enjoy …
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