CtrlAltInvest

Jason Vondersmith
  • 3.7 (3)
  • INVESTING

🚀 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 advantages, and real passive income (no plumbing emergencies, we promise). For W2 Employees: Learn to hack your 401k and invest in real estate like the pros (no Wall Street middlemen required). For CRE Sellers: Find out what today’s top syndicator's look for in self-storage deals (spoiler: it’s all about data). 🔥 What You’ll Hear: Raw breakdowns of live self-storage deals (the good, the bad, and the ugly). Interviews with rebels who ditched Wall Street to build 7-figure portfolios. Tactics to turn retirement accounts into real estate empires (yes, it’s legal). Rants about why your 401k is not a retirement plan (and what to do instead). 🎙️ New episodes drop [weekly/biweekly]. Subscribe now and join the rebellion. “Because wealth shouldn’t be a secret handshake—it’s time to Ctrl Alt the System.”

  1. 11/21/2025

    Throwing Shit at the Wall: 50-Year Mortgages, Tariff Dividends, and Why Nobody Owns Anything Anymore

    Jason and James dive deep into the housing affordability crisis and the increasingly absurd solutions being floated by policymakers. From 50-year mortgages to portable loans to $2,000 tariff dividend checks, it seems like we're in the era of "throw it at the wall and see what sticks" economic policy. Topics CoveredControl R (News Roundup) Car repos hit highest levels since 2009 - what it signals about consumer stress Portable and assumable mortgages: Fannie/Freddie's new experiment The 50-year mortgage proposal and why it might not actually help affordability Trump's $2,000 tariff dividend checks (and why Scott Bessent is walking it back) Alt View (Deep Dive) How Blackstone became America's largest single-family landlord The real impact of private equity on neighborhoods and rent prices 2008 to today: Median home prices doubled ($200k → $420k) while incomes barely budged ($52k → $75k) Why extending mortgage terms won't solve the affordability crisis Baby boomers holding 42% of primary homes - the inventory crisis nobody talks about Potential solutions: Removing capital gains taxes on boomer home sales Control Panel (Q&A) Why tariff dividend checks are a terrible idea (even if we were profitable as a country)Where tariff revenue should actually go Looking Ahead Government shutdown impacts on markets Michael Burry closes his company Is it time to start a business instead of buying one? Key Quotes"So 2008 median home price was $200,000. Today, it's $420,000. Holy shit. But don't worry, median household income came right along, right? Nope." "It's the presidency of throwing shit at the wall and seeing what sticks." "We're not a country, we're not a business... Once you taste that money, you're never giving it back."

    44 min

  2. 11/20/2025

    Ctrl Alt Invest Returns: Cash, Crashes, and Why Private Equity is Eating Your HVAC Guy

    The pivot is here. After a summer break, Ctrl Alt Invest is back with a new format but the same mission: cut through Wall Street's BS and talk about what actually matters to regular investors. In this episode: Government Shutdown Reality Check The right-wing talking point that "the government's been shut down and your life hasn't changed" ignores the TSA workers directing planes without paychecks and families living paycheck-to-paycheck being forced to drive Uber just to survive. Plus: October saw the most private sector layoffs since 2003, and CEOs are blaming "AI" for everything. NYC's New Mayor & Socialist Fears Mom Donnie (Mondami) won, and conservatives are freaking out. Is he actually a socialist, or is this just more political theater? We break down what city-level policy actually means when the federal government isn't playing ball. Commercial Real Estate's Ticking Time Bomb Everyone talks about residential mortgages, but commercial mortgage-backed securities—especially multifamily—are showing serious cracks. Defaults are climbing fast, but here's the thing: commercial defaults work differently than residential. Banks don't want your 200-unit building. They'll negotiate. We explain what this means for average investors and why your local strip mall might be in trouble. Being "In Cash" in a Volatile Market Warren Buffett is sitting on $380 billion in cash. Should you be hoarding cash too, or is that just preparing for discounts? We discuss currency devaluation risks, what Buffett's actually doing with that money (spoiler: Treasury bills), and whether the doomsday bread-line scenario is actually coming. Control Panel: Private Equity is a Problem Listener question: Is now a good time to invest in private equity? Our take: Hell no. Private equity firms are buying up mom-and-pop businesses—HVAC companies, service providers—slapping iPads on contractors, implementing dynamic pricing (charge the guy with the Mercedes more), and running these businesses into the ground. Real example: PE firm buys successful HVAC company, pivots entire business to just selling generators because of margins. Spoiler: It's failing. The problem? Financial guys with spreadsheets don't know jack about selling HVAC systems. Just because you can make money in markets doesn't mean you know how to run a plumbing business. Looking Ahead: James is watching Palantir's trajectoryJason's tracking gaming stocks and the DraftKings/ESPN partnership (after Penn pulled out) This isn't a reboot. It's a hard pivot. Welcome back.

    34 min

  3. 10/24/2025

    Beyond Stocks & Bonds: Kim Flynn Shows Retail Investors the Real Game

    Beyond Stocks & Bonds: Kim Flynn Shows Retail Investors the Real Game🔓 Episode Summary For decades, the best investment opportunities have been locked behind a velvet rope marked "Accredited Investors Only." While institutional investors and the ultra-wealthy have been quietly building fortunes through private equity, hedge funds, venture capital, and commercial real estate, everyday investors have been stuck with mutual funds and ETFs. Not anymore. In this game-changing episode, Jason and James sit down with Kim Flynn from XA Investments to pull back the curtain on alternative investments and reveal how retail investors can finally access the strategies that Wall Street has kept to itself. From real estate syndications to private credit, from venture capital to commodities—Kim breaks down what alternative investments actually are, why they matter, and most importantly, how regular investors can get in the game. If you've ever felt like the financial system was rigged against you, this episode is your playbook for fighting back. What You'll Learn✅ The difference between alternative and traditional investments (and why it matters) ✅ Why alternatives can provide better returns and lower correlation to stock market volatility ✅ How recent regulatory changes are opening doors for retail investors ✅ The specific types of alternative investments available to everyday investors ✅ Red flags to watch for when evaluating alternative investment opportunities ✅ How to start investing in alternatives with as little as $500-$5,000 ✅ Tax advantages that come with certain alternative investments ✅ Portfolio allocation strategies: How much should you put into alternatives? Connect with Kim Flynn: 🌐 XA Investments: xainvestments.com 💼 LinkedIn: linkedin.com/in/kimberlyannflynn Take ActionReady to Ctrl Alt Your Portfolio? Visit vondiecapital.com for your free wealth plan and discover how self-storage syndications can deliver passive income and tax advantages that Wall Street can't match. Mention this podcast episode to skip the waitlist! Rate & Review: If this episode opened your eyes to new investment possibilities, drop us 5 stars on Apple Podcasts or Spotify. Your reviews help other investors find their way out of the Wall Street maze. Who's This For?📍 W2 employees tired of watching their 401(k) go nowhere 📍 Retail investors ready to diversify beyond stocks and bonds 📍 Anyone who's ever felt shut out of the "good" investment deals 📍 Investors looking for passive income streams and tax advantages 📍 People curious about the alternatives the wealthy have been using for decades Tags#AlternativeInvestments #WealthBuilding #PassiveIncome #RealEstateInvesting #PrivateEquity #RetailInvesting #FinancialFreedom #Investing #VentureCapital #PrivateCredit #Syndication #TaxAdvantages #PortfolioDiversification #InvestmentStrategy #MoneyMindset About Ctrl Alt InvestHosted by Jason Vondersmith and James Goodwillie, Ctrl Alt Invest is the podcast that's pressing reset on wealth creation. We're done with Wall Street's

    42 min

  4. 05/28/2025

    $19 Trillion Power Play: How BlackRock Dominates Wall Street & Your 401(k)

    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 Aladdin, revealing why the system bends to a select few—and what you can do about it. KEY TOPICS COVERED00:17 – Why “tear down the facade” of traditional wealth advice still matters today 02:45 – The psychological pivot away from Wall Street’s comfort narrative 08:10 – BlackRock + Vanguard’s $19–22 T grip and majority ownership of 90 % of S&P 500 firms—what that means for your 401(k) 14:20 – How the Fed handed BlackRock $750 B in 2020 to “stabilize” markets—and BlackRock bought its own ETFs 22:05 – Aladdin: the proprietary AI that de-risks trillions and fuels BlackRock’s shadow power 30:40 – Money vs. power: why Larry Fink’s personal wealth is dwarfed by his influence—and how that affects policy 36:10 – Alternative paths: outrunning the “bear” by diversifying into off-Wall-Street plays QUOTABLE MOMENTS“If BlackRock were a country, it would be the biggest economy on earth.” — James “In America, when you seize on chaos, you don’t become a dictator—you own a bank.” — Jason “You don’t have to outrun the bear—just the slower investors still trusting autopilot 401(k)s.” — James ACTIONABLE TAKEAWAYSAudit your retirement plan – Check which BlackRock or Vanguard funds your 401(k) automatically buys; rebalance intentionally.Reallocate 10-20 % into alternatives – Consider real estate syndications, private credit, or crypto for true diversification and cash flow.Follow the power, not the hype – Track policy hires and bailouts tied to BlackRock/Vanguard; they telegraph market moves.Measure wealth in time – Use passive-income plays to buy back hours, not just portfolio points.Keep an “Aladdin radar” – Monitor emerging AI-driven funds so you’re not the last to know where risk is being off-loaded. BOOKS MENTIONED“All the Worst Humans” by Phil Elwood“Meditations” by Marcus Aurelius"All The Presidents' Bankers" by Nomi Prins Be sure to subscribe to our Youtube to check out clips and full videos of our pods!

    39 min

  5. 05/21/2025

    Gatekeeping the Greed: How Hedge Funds, Regulation & Power Shape Your Wallet

    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-trading crackdowns, meme-stock revolts, Puerto-Rican tax havens, and whether America has quietly slipped into oligarchy. You’ll learn why “regulation” can create more gatekeepers, how market shake-ups hit your 401(k), and what collective action really takes. If you’ve ever wondered why the rich stay rich—and what you can do about it—press play. Quick Navigation00:00 – Introduction to Gatekeeping in Finance 03:03 – The Genesis of Hedge Funds 05:54 – The Evolution of Hedge Funds & Key Figures 09:02 – The Dark Side of Hedge Funds 11:58 – Regulation & the Hedge Fund Market 14:57 – Scandals & Failures in Hedge Fund History 18:05 – The Impact of Hedge Funds on the Economy 20:58 – The Role of Government & Regulation 24:06 – Oligarchy & Corporate Influence 27:03 – Privacy, Surveillance & Corporate Power 28:30 – Historical Perspectives on Wealth & Power 30:49 – The Role of Oligarchs in Modern Society 34:06 – Government Influence & Economic Policies 37:01 – The Hedge Fund Landscape & Its Implications 39:58 – Tax Strategies & Wealth Management 45:00 – Regulation & Its Impact on the Market 49:47 – The Future of Wealth Distribution 55:04 – Collective Action Against Financial Inequities Key TakeawaysHedge-fund history: From Alfred Jones to Bridgewater and CitadelScandals decoded: Madoff, SAC Capital, Archegos, junk-bond eraRegulation paradox: How new rules can entrench gatekeepersOligarchy vs. democracy: Concentrated wealth, political captureTax arbitrage: Puerto-Rico Act 60 loopholes for fund managersAction steps: Community investing, diversified indexing, policy engagement Resources MentionedBooks: “Principles” by Ray Dalio, “All the Presidents’ Bankers” by Nomi PrinsDocs: Netflix “Madoff: The Monster of Wall Street,” PBS “The Crash of 2008”Tools: SEC Edgar filings, FINRA Investor Education ⭐️ Love the show? Rate & review on Apple & Spotify Podcasts—it helps fellow rebels find us! Subscribe to our channel on Youtube for videos!

    47 min

  6. 05/09/2025

    Markets Unmasked: From Dutch Spice Ships to Meme Stock Mania

    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 hear about:The Birth of the Stock Market: How did the Dutch East India Trading Company pave the way for the first shareholders?Casino Capitalism: Is the modern stock market more about gambling than investing? Jason and James peel back the layers.Market Manipulation: From Black Monday to GameStop—how billionaires and hedge funds shape financial narratives.Comparing Markets: Labor, real estate, cryptocurrency, baseball cards—how do they stack up against traditional financial markets?The Scam Spectrum: Marketing vs. scams—where do gurus like Grant Cardone and his "10x" mantra fall?Michael Burry & Predictions: When does being early become indistinguishable from being wrong? 🔥 Key Takeaways:What truly defines a market, and why is money always at its core?Understanding how markets work helps you see through hype and manipulation.Not all markets are created equal—learn how to spot which ones can actually help build sustainable wealth. 🚨 Hot Take Alert:Is modern America built on separating people from their money? Jason and James tackle this provocative question head-on! Join the conversation! Subscribe to CtrlAltInvest to keep exploring how wealth, finance, and markets intersect in today's rapidly changing world. Don't forget to rate, review, and share the podcast with friends who love smart insights with a side of laughs! Check us out on Youtube! CtrlAltInvest: Resetting the way you think about wealth creation.

    43 min

  7. 05/02/2025

    Why Diversification Is a Lie: Jordan Brown on Self-Storage Syndications & Building Real Wealth

    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 explore why concentrating on a niche you control (like cash-flowing storage facilities) can crush a “401(k) & hope” strategy, how to raise capital through real-estate syndications, and the mindset shift from instant to delayed gratification. Key Takeaways 03:30 – The origin of Jordan’s “diversification is a lie” post08:15 – What working inside a brokerage taught him about hidden fees & limited products18:40 – Why he chose self-storage over duplexes, office, or multifamily24:10 – “You don’t need your own money to buy real estate” — the sweat-equity playbook31:45 – Structuring a $3.5 M storage syndication (raising $1.8 M in equity)41:00 – Teaching kids delayed gratification in an instant-gratification world45:50 – Action steps for listeners: meetups, masterminds & leveraging your specialty Episode HighlightsThe Diversification Myth — Asset-allocation funds have trailed the S&P 500 for 15 straight years; broad diversification can actually dilute returns when only a handful of “Magnificent 7” stocks move the index.Own the Casino, Don’t Play It — Jordan explains why buying “ugly, bullet-proof ATMs” (storage units) beats gambling on meme stocks or index funds.Sweat Equity Matters — How beginners can trade hustle for equity shares in larger commercial deals.Family & Finance — Building generational wealth and teaching children that real estate is a “get-rich-slow” scam worth running. About Our Guest — Jordan BrownDirector of Investor Relations turned full-time self-storage operatorPortfolio: 177-unit facility plus commercial suites & duplexes (since 2019)Passionate about mentoring new investors & riding dirt bikes between diaper changes Connect with Jordan: Vondiecapital.com (book a call) Call to ActionSubscribe & Review Ctrl Alt Invest on Apple Podcasts or Spotify—your 5-star review helps more investors escape Wall Street groupthink.Follow us on YouTube for behind-the-scenes clips & market updates.

    44 min

  8. 04/25/2025

    From Rentals to Care Homes: Vinod’s Wealth Blueprint

    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 Highlights[00:07:57] Why you don’t need your own money to start—contacts, knowledge and a solid deal matter more.[00:09:04] Vinod’s first two rentals in the 2009 crash and his 20-25 % capital rule.[00:13:00] Underwriting an apartment syndication: cash-flow, IRR and five-year exit math.[00:23:40] Accredited-investor “gatekeepers” and how to work around them legally.[00:29:45] The aha-moment that turned a headache facility into a hands-off, triple-net lease.[00:34:12] Why REITs haven’t touched small care homes—yet—and what that could mean for your exit.[00:37:20] Plant the seed, let it sprout: compounding cash-flows without quitting your W-2. Topics CoveredReal Estate vs. the Stock MarketVolatility, control and why Vinod still funds his 401(k) but chases higher, steadier yields in property. From Single-Family to Multifamily2009 bargains, Excel models and scaling into apartment complexes with partners. Assisted-Living Cash-CowsResidential care homes (8–10 beds) as an overlooked niche riding the baby-boomer wave.Licensing, ADA retrofits and leasing to professional operators instead of self-managing. Funding & Diversification Strategies20–25 % personal capital cap; bringing in investors for the rest.Passive LP positions in out-of-state deals for geographic spread. Time Management for Busy ProfessionalsUsing property managers, automating reporting and carving out due-diligence “micro-blocks” during the workday. Exit Options & REIT PotentialPackaging 10–20 care homes for an institutional buyout as the sector institutionalizes. Key TakeawaysLeverage knowledge, not just cash. A well-modeled deal attracts money.Think demographics. Aging boomers = decades of demand for assisted living.Cap your risk. Vinod never invests more than a quarter of his own capital in a single deal.Stay diversified. Stocks, storage, apartments and care homes all play a role.Make it passive. Lease to operators or hire managers so your portfolio works while you do. Guest InformationVinod Vangimalla is a finance director, real-estate investor and former Atlantic City poker finalist. He owns and leases multiple residential assisted-living facilities in Arizona and invests passively in multifamily across the U.S. Connect via LinkedIn (https://www.linkedin.com/in/vinodvangimalla/) or request his contact details at vondiecapital.com. Call-to-ActionIf you learned something new, subscribe, rate and review the Ctrl Alt Invest Podcast on your favorite app.

    43 min
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Ratings & Reviews

3.7
out of 5
3 Ratings

About

🚀 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 advantages, and real passive income (no plumbing emergencies, we promise). For W2 Employees: Learn to hack your 401k and invest in real estate like the pros (no Wall Street middlemen required). For CRE Sellers: Find out what today’s top syndicator's look for in self-storage deals (spoiler: it’s all about data). 🔥 What You’ll Hear: Raw breakdowns of live self-storage deals (the good, the bad, and the ugly). Interviews with rebels who ditched Wall Street to build 7-figure portfolios. Tactics to turn retirement accounts into real estate empires (yes, it’s legal). Rants about why your 401k is not a retirement plan (and what to do instead). 🎙️ New episodes drop [weekly/biweekly]. Subscribe now and join the rebellion. “Because wealth shouldn’t be a secret handshake—it’s time to Ctrl Alt the System.”

Information

  • Creator
    Jason Vondersmith
  • Years Active
    2K
  • Episodes
    15
  • Rating
    Explicit
  • Copyright
    © Copyright 2025 Jason Vondersmith
  • Show Website
    CtrlAltInvest