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CtrlAltInvest

Jason Vondersmith

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🚀 Tired of Wall Street’s broken promises? Ctrl Alt Invest is the podcast for accredited investors, corporate warriors, and real estate pros who want to rewrite the rules of wealth. Hosted by Jason Vondersmith (data engineer by day, self-storage syndicator by passion), and James Goodwillie we’re tearing up the traditional playbook and replacing it with strategies that actually work: For Accredited Investors: Discover how self-storage syndication's deliver recession-proof cash flow, tax advant ...
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Think Wall Street’s rigged? This episode uncovers how two “quiet” giants—BlackRock and Vanguard—manage a combined $19 trillion+ in assets and hold majority stakes in almost 90 % of the S&P 500—yet most investors have never questioned their influence. Jason and James trace the playbook from J.P. Morgan’s 1907 panic rescue to BlackRock’s AI engine Al…
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Episode Summary Hedge funds were born as a clever way to hedge risk—so how did they become the ultimate financial gatekeepers? In this fiery Ctrl-Alt-Invest deep-dive, Jason Vondersmith and James Goodwillie trace hedge-fund history from Alfred Jones in 1949 to today’s billion-dollar family offices. Along the way we unpack junk-bond kings, insider-t…
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Welcome back to CtrlAltInvest! Jason Vondersmith and James Goodwillie are diving head-first into the vast, intriguing, and often misunderstood world of markets. From the historic roots of stock exchanges to the bizarre dynamics of modern finance, this episode is packed with insights, humor, and thought-provoking debates. 🎙️ In this episode, you’ll …
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Introduction Financial freedom rarely comes from playing Wall Street’s rigged game. In this eye-opening conversation, hosts Jason Vondersmith and James Goodwillie sit down with Jordan Brown—self-storage investor, Utah State Aggie, father of twins, and reformed financial advisor—to unpack his viral hot-take: “Diversification is a lie.” Together they…
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Brief Introduction Hosts Jason Vondersmith and James Goodwillie welcome finance executive Vinod Vangimalla—econ grad (UMD), MS-Finance (UC Irvine) and Director of Finance at Value Savers—to unpack how he scaled from single-family rentals to a portfolio of leased, residential assisted-living homes that cash-flow while he keeps his day job. ​ Episode…
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Taxes got you stressed? Join Control Alt Invest as Jason Vondersmith & James Goodwillie unpack the messy world of taxes—federal vs. state, income to capital gains. From Founding Fathers’ debates to today’s 4M-word tax code, learn why complexity hurts the little guy & how the wealthy game the system. Get tips to navigate tax season & build wealth sm…
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Dive into Control Alt Invest’s deep dive on tariffs—the 2025 buzzword shaking markets! Hosts Jason Vondersmith & James Goodwillie break down what tariffs mean for your 401(k), small biz, & global trade. From Hamilton’s era to Trump’s tweets, explore how taxes on imports spark volatility, crush China’s edge, & hit your wallet. Get actionable tips to…
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Leverage isn’t just for hedge fund bros—it’s the ultimate tool for rebels, contrarians, and anyone who knows the system is rigged. In this episode, we break down the good, the bad, and the ugly of leverage: how Wall Street abuses it, how you can use it smarter than they do, and why your 401k-loving financial advisor won’t touch this topic with a 10…
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Key Takeaways: The Instagram Facade: Social media platforms like Instagram often present a curated version of success, hiding the true costs and struggles behind the scenes. It's essential to look beyond the highlight reels. Time: The Ultimate Currency: Time is the most precious resource you have. Every decision should be evaluated based on how it …
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What does it really mean to be too big to fail? In this episode, we break down the history behind this phrase and its real-world implications. From the very first government bailout to the Great Depression and the taxpayer-funded rescue during the 2008 financial crisis, we examine how institutions grow so large that their failure could shake entire…
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Is your money really safe? In this episode, we break down the misconceptions around investment security, exploring the risks hidden in so-called "safe" assets like savings accounts, bonds, and even 401(k)s. We uncover how market volatility—driven by sentiment, not just performance—impacts stocks and discuss whether real estate investment trusts (RE…
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Tired of playing Wall Street’s rigged game? In this episode, we rip apart the 401(k) myth and expose how Wall Street gets rich while you take all the risk. Here’s what we cover: ✅ Why your 401(k) is designed to keep you broke while fund managers cash in ✅ The 2008 financial crisis—how Wall Street gambled with your money and walked away rich ✅ Why r…
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