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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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Send us a text 00:00 - Intro 00:08 - Tether's $500B Valuation 00:54 - OpenAI-Nvidia $100B AI Powerhouse Deal 02:10 - Stripe BuyBack at $106.7B 02:48 - TikTok US Valuation at Only $14B! 03:45 - Fermi's $13B IPO for AI Data Center Energy 04:18 - 1X Robotics' $10B+ Valuation 05:21 - Anthropic for Microsoft AI Copilot 05:51 - Databricks-OpenAI $100M En…
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Send us a text Nick Fusco = CEO at PM Insights, a pre-IPO secondary market pricing company …X - @TheFuscoKid …LinkedIn - www.linkedin.com/in/nickfusco Evan Cohen = Founder/COO of withVincent.com, a media company focused on alternative investments …X - @evvcohen …LinkedIn - www.linkedin.com/in/evcohen Clint Sorenson = Chief Investment Officer at Wea…
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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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Send us a text 00:00 - Intro 00:55 - Groq's $750M Funding, $6.9B Valuation 02:23 - Figure's $1B+ Robotics Raise, $39B Valuation 03:20 - Workday's $1.1B Sana Acquisition for AI Agents 04:12 - Irregular's $80M AI Security Boost 05:34 - xAI's 64M User Milestone 06:27 - OpenAI's New ChatGPT Usage Report 07:59 - OpenAI to Cut Microsoft Rev Share 08:45 -…
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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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Send us a text 00:00 - Intro 00:02 - SpaceX to enter the cell service business 04:26 - Anduril wins $1.26b of new deals 12:43 - OpenAI + Microsoft work out non-profit to for-profit switch 17:33 - Will AI/robotics yield a decade long bull market? Nick Fusco = CEO at PM Insights, a pre-IPO secondary market pricing company …X - @TheFuscoKid …LinkedIn …
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Send us a text 00:00 - Intro 00:51 - Klarna's $15.1B IPO + Up in Public Markets (as of Thu, Sep 11) 01:51 - Cognition's $400M Raise at $10.2B Valuation 02:43 - ElevenLabs' $100M Tender at Doubled $6.6B Valuation 03:05 - Replit's $250M Funding at $3B Valuation 04:05 - X Square Robot's $140M Raise, New Robot OS Released 04:41 - Mistral Finalizes $1.5…
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Send us a text 00:00 - Intro 00:11 - Revolut $75b valuation after 72% yoy revenue growth, 35 million customers 11:09 - AI App investment cases; Sierra AI Agents and OpenEvidence Nick Fusco = CEO at PM Insights, a pre-IPO secondary market pricing company …X - @TheFuscoKid …LinkedIn - www.linkedin.com/in/nickfusco Evan Cohen = Founder/COO of withVinc…
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Send us a text 00:00 - Intro 00:54 - Anthropic Secures $183B Valuation Funding Milestone 01:32 - Revolut Achieves $75B Valuation Share Sale 02:10 - OpenAI Expands Tender from $6B to $10.3B 03:07 - OpenAI Completes $1.1B Statsig Acquisition 04:00 - OpenAI Launches Proprietary AI Chip Development Initiative 04:47 - Lambda $6B Round + IPO Preparation …
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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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Send us a text 00:00 - Intro 00:52 - ByteDance Buyback at $330B, More Revenue vs Meta 02:17 - Klarna IPO Back On 03:28 - Framer $2B Valuation Series D 04:21 - Rain Raises $58M for Stablecoin Payments Platform 05:34 - Commonwealth $863M for Fusion Prototype 06:38 - SpaceX 10th Starship Test a Huge Win 07:42 - Anthropic Launches Chrome AI Agent 08:47…
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Send us a text 00:00 - Databricks Targets $100b in New Round 08:42 - Canva Launches Tender at $42b Valuation 15:27 - Eight Sleep Raises $100m at $1.5b Nick Fusco = CEO at PM Insights, a pre-IPO secondary market pricing company …X - @TheFuscoKid …LinkedIn - www.linkedin.com/in/nickfusco Evan Cohen = Founder/COO of withVincent.com, a media company fo…
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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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Send us a text 00:00 - Intro 00:54 - Databricks Targets $100b in New Round 01:53 - Canva Launches Tender at $42b Valuation 02:49 - Crusoe Eyes $1b Raise at $10b Valuation 03:27 - Anthropic Doubles Raise to $10b at $170b 04:15 - Eight Sleep Raises $100m at $1.5b 04:47 - Manus Hits $90m ARR in 6 Months 05:17 - Anduril Sponsors Ohio State Athletics 06…
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Is now the right time to buy real estate or to hold cash? In this episode, Tait Duryea and Ryan Gibson sit down with Hunter Thompson, founder of Asym Capital and host of Cash Flow Connections, to unpack today’s real estate market. They cover cycles, debt structures, the COVID impact, rising interest rates, and why current distress is more about fin…
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Send us a text 00:00 – OpenAI Tender Eyes $500b Valuation 06:32 – Cohere Raises at $6b Valuation 12:11 – n8n Raises at $2.3b Pre-Money Nick Fusco = CEO at PM Insights, a pre-IPO secondary market pricing company …X - @TheFuscoKid …LinkedIn - www.linkedin.com/in/nickfusco Evan Cohen = Founder/COO of withVincent.com, a media company focused on alterna…
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What if your life insurance could help you invest without selling a single asset? Tait Duryea and Ryan Gibson welcome back Rod Zabriskie of Money Insights to demystify how whole life insurance can be used as a wealth-building tool. They break down the differences between term and whole life, how cash value grows, and why this strategy avoids risks …
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Send us a text 00:00 - Intro 00:54 - OpenAI Tender Eyes $500b Valuation 01:38 - OpenAI Offers Govt ChatGPT for $1 02:14 - OpenAI Releases Open-Weight Models 02:57 - OpenAI Launches GPT-5 Model 03:33 - Bullish Targets $4.23b IPO Valuation 04:46 - n8n Raises at $2.3b Pre-Money 05:47 - Figure Technology Files $3.3b IPO 06:37 - Clay Raises $100m at $3.…
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What if your first home turned into your first big win? Tait Duryea and Ryan Gibson welcome Brad Hilton and Aubrey Carlson, a powerhouse pilot couple who turned a VA loan into a cash-flowing real estate business. From renovating a dated beach house to designing destination-worthy cabins in Julian, CA, Brad and Aubrey break down how they scaled a sh…
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Send us a text 00:00 - Intro 00:52 - Figma Surges 250% on NYSE Debut to $56b 02:10 - Anthropic Triples Valuation to $170b in New Round 03:01 - Ramp Jumps 40% to $22.5b in 45 Days 04:23 - iCapital Raises $820m to $7.5b Valuation 05:28 - BitGo Files IPO at $3.43b Secondary Valuation 06:05 - Substack Boosts 70% to $1.1b on $100m Raise 06:51 - Shein Po…
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Send us a text CHAPTERS 00:00 – Anthropic $150b valuation (now $170b!!!) 15:13 – xAI + Valor for GPUs 29:55 – Figma IPO valuation set at $15-$16b PARTICIPANTS Nick Fusco = CEO at PM Insights, a pre-IPO secondary market pricing company …X - @TheFuscoKid …LinkedIn - www.linkedin.com/in/nickfusco Evan Cohen = Founder/COO of withVincent.com, a media co…
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What separates a solid real estate deal from a costly mistake? In this episode, hosts Tait Duryea and Ryan Gibson welcome Derrick Harris, SVP at Spartan Investment Group, to walk us through the real-world process of evaluating markets, properties, and operational risks. With a portfolio that spans millions of square feet, Derrick shares what works,…
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Send us a text 00:00 - Intro 00:53 - Anthropic Targets $100B Valuation 02:21 - Anthropic Launches Claude 4 Financial Tools 03:20 - Thinking Machines Raises $2B at $12B Valuation 04:58 - OpenEvidence Secures $210M at $3.5B Valuation 07:11 - Xtend Adds $30M to Reach $100M Total Funding 09:10 - Cognition Acquires Windsurf with $82M ARR 11:12 - Via Fil…
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What if your rental property is a lawsuit away from costing you everything? Tait Duryea connects with asset protection expert Adam Kintigh of Nevada Corporate Headquarters to break down what every investor should know about shielding wealth. From piercing the corporate veil to choosing between LLCs and real estate privacy trusts, this episode cover…
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Send us a text 00:00 – Aquihires in AI: A better form of M&A? 13:02 – JPMorgan's Data Fees: Innovation Killer in Fintech? 26:03 – Mega Funding Rounds: Revolut, SpaceX, Groq, Mistral, Harmonic, xAI(?) 41:39 - Electricity as Commodity: Does anyone have a guy? Nick Fusco = CEO at PM Insights, a pre-IPO secondary market pricing company …X - @TheFuscoKi…
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Get ready to demystify the 2025 Tax Bill. Hosts Tait Duryea and Ryan Gibson sit down with Nathan Sosa, tax strategist at Hall CPA, to uncover what this sweeping legislation really means for pilots and high-income earners. From the return of 100% bonus depreciation to new deductions for auto loans and overtime, Nathan breaks down exactly who benefit…
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Send us a text 00:00 - Intro 00:55 - SpaceX Soars to $400B Valuation 01:46 - Revolut Banks on $65B Valuation Boost 02:37 - Groq Chips In at $6B Valuation 03:42 - Mistral AI Storms to $1B+ Raise 04:41 - Harmonic AI Tunes Up to $875M Valuation 05:36 - xAI Unleashes Grok 4 at PhD-Level Smarts 07:32 - X's Yaccarino Exits After X Merger 08:19 - Perplexi…
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Send us a text 00:00 – Groq is the private market Nvidia? 07:24 – Figma’s IPO a buy? 13:30 – Robinhood’s pre-IPO stock tokenization legal and good for investors? PARTICIPANTS Nick Fusco = CEO at PM Insights, a pre-IPO secondary market pricing company …X - @TheFuscoKid …LinkedIn - www.linkedin.com/in/nickfusco Evan Cohen = Founder/COO of withVincent…
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Ever wonder what happens when you invest in a syndication? In this episode, hosts Tait Duryea and Ryan Gibson break down how real estate syndications work, from deal sourcing and underwriting to legal docs, fees, and investor returns. Learn how passive investors get access to large-scale deals, what to look for in a sponsor, and what happens after …
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Send us a text The Compound is a go to source of financial news and insights for me on a weekly basis. What Are Your Thoughts on Tuesdays, Animal Spirits on Wednesdays, and The Compound and Friends on Friday. Incredible insights from Josh, Michael, and Ben Carlson. I highly recommend a Youtube subscribe at https://www.youtube.com/@TheCompoundNews .…
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Send us a text 00:00 - Harvey disrupting the law firm industry, or driving it to new revenue levels? 15:41 - Wealthfront a buy post-IPO? 24:45 - Prediction markets a business with staying power?By AG Dillon & Co
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Send us a text 00:00 - Intro 00:53 - Harvey Eyes $5B Primary Valuation Amid Legal AI Surge 01:58 - Wealthfront Preps IPO After Strong $290M Revenue 02:42 - Snyk Acquires Invariant to Secure AI Risks 03:47 - PlayAI In Acquisition Talks With Meta 04:46 - OpenAI and Microsoft Clash Over AGI Clause 06:12 - Kalshi Hits $2B Primary Valuation Amid Legal W…
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What could cost you your flying career? Not being prepared for your medical. Hosts Tait Duryea and Ryan Gibson welcome back Dan Monlux of Wingman Med to discuss how pilots can protect their FAA medical certificates. Dan breaks down what happens during a medical exam, the importance of primary care, and why early detection matters. This is a must-li…
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Send us a text 00:00 - Intro 00:39 – OpenAI proposes Microsoft own 33% equity in for-profit transition 11:10 – Cluely records everything you see, say, and hear 25:32 – Canva secondary deal at $37b valuation 31:54 – What is Scale’s secondary valuation post-Meta deal?By AG Dillon & Co
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Send us a text 00:00 - Intro 00:54 - OpenAI Strikes Defense Deal, Hits $314B in Secondaries 01:54 - OpenAI-Microsoft Standoff Over Equity, Revenue, IP, and AGI 03:07 - xAI Burns Billions, Seeks $9.3B More Amid $121B Valuation 04:13 - Anysphere Doubles Valuation Weeks After Raise 05:30 - GENIUS Act Sets Stage for Stablecoin Innovation 06:39 - X Buil…
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Get ready to uncover the secrets of one of commercial real estate’s most resilient and misunderstood asset classes: self-storage. In this in-depth episode, Tait Duryea and Ryan Gibson explore why self-storage continues to outperform in uncertain times, how millennials are transforming storage use, and what makes it such a powerful wealth vehicle fo…
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Send us a text 00:00 - Intro 00:51 - Scale AI gets $14.3B from Meta, hits $29B valuation 02:03 - Starlink doubles subs to 6M, adds 100K in Africa 03:22 - SpaceX expands Starship launch capacity in Florida 04:08 - Databricks adds Google Gemini, hits $72.8B valuation 05:09 - Perplexity partners with Nvidia, eyes $14B raise 06:08 - Glean raises $150M …
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In this episode, hosts Tait Duryea and Ryan Gibson sit down with attorney Amanda Wynalda from Anderson Advisors to unpack everything pilots and high-income earners need to know about trusts, wills, and asset protection. From revocable vs. irrevocable trusts to layering LLCs and avoiding the due-on-sale clause, this episode is a blueprint for protec…
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In this episode, hosts Tait Duryea and Ryan Gibson talk with chief economist Dr. Peter Linneman to demystify interest rates, the national deficit, and how it all affects pilots, real estate investors, and entrepreneurs. Discover why U.S. debt may not be the threat it’s made out to be, how capital flows drive values, and what most people get wrong a…
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Send us a text 00:00 - Intro 00:46 - Musk's political bets pay off 08:21 - Future of personal devices (Neuralink, OpenAI/Ive, Meta/Google glasses) 22:42 - AI Apps the next huge investment opportunity?By AG Dillon & Co
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In this episode, Tait Duryea and Ryan Gibson welcome CPA Thomas Castelli of Hall CPA to break down the latest tax developments affecting high-income earners. From the potential return of 100% bonus depreciation to how the real estate professional status works in practice, Tom shares key strategies to help you keep more of what you earn. Whether you…
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Get ready to fast-track your financial freedom. In this power-packed solo episode, Tait Duryea and Ryan Gibson share the top strategies from over 110 episodes of Passive Income Pilots. From unlocking hidden cash in your 401(k) and home equity to leveraging life insurance and short-term rentals for major tax breaks, they distill years of pilot-speci…
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In this episode, hosts Tait Duryea and Ryan Gibson welcome Ramez Fakhoury from IRA Club. This episode dives into how pilots can unlock old 401(k)s, TSPs, and HSAs for real estate and other alternative investments. Hear a detailed story of a Southwest pilot transitioning to American Airlines and learn what decisions made the biggest impact. Whether …
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Send us a text 00:00 - Intro 00:07 - SpaceX Cleared for 25 Starship Launches at Starbase 00:58 - Wonder Raises $600M at $7B+ Valuation 01:46 - Function Health Seeks $2B Valuation After Ezra Deal 02:38 - OpenAI Seeks to Restructure Microsoft Deal 03:51 - OpenAI Appoints Instacart CEO to Lead Applications Division 05:26 - Stargate Plans $500B Global …
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In this episode, hosts Tait Duryea and Ryan Gibson deliver an in-depth, pilot-friendly primer on syndications and passive real estate investing. They break down the risk spectrum from core to opportunistic deals, while sharing real-world analogies and experiences from their own projects, like the Canyon City land entitlement. Learn how to properly …
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Send us a text 00:00 - Intro 00:21 - Nick in Omaha for Warren Buffett 13:14 - eToro IPO is happening! 19:09 - Epic wins vs Apple, Fortnite back on iOS 28:52 - Starlink winning in Africa, Congo approvalBy AG Dillon & Co
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