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.

00:17 – 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

1. “If BlackRock were a country, it would be the biggest economy on earth.” — James
2. “In America, when you seize on chaos, you don’t become a dictator—you own a bank.” — Jason
3. “You don’t have to outrun the bear—just the slower investors still trusting autopilot 401(k)s.” — James

1. Audit your retirement plan – Check which BlackRock or Vanguard funds your 401(k) automatically buys; rebalance intentionally.
2. Reallocate 10-20 % into alternatives – Consider real estate syndications, private credit, or crypto for true diversification and cash flow.
3. Follow the power, not the hype – Track policy hires and bailouts tied to BlackRock/Vanguard; they telegraph market moves.
4. Measure wealth in time – Use passive-income plays to buy back hours, not just portfolio points.
5. Keep an “Aladdin radar” – Monitor emerging AI-driven funds so you’re not the last to know where risk is being off-loaded.

• “All the Worst Humans” by Phil Elwood
• “Meditations” by Marcus Aurelius
• "All The Presidents' Bankers" by Nomi Prins

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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-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.

00:00 – 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

• Hedge-fund history: From Alfred Jones to Bridgewater and Citadel
• Scandals decoded: Madoff, SAC Capital, Archegos, junk-bond era
• Regulation paradox: How new rules can entrench gatekeepers
• Oligarchy vs. democracy: Concentrated wealth, political capture
• Tax arbitrage: Puerto-Rico Act 60 loopholes for fund managers
• Action steps: Community investing, diversified indexing, policy engagement

• Books: “Principles” by Ray Dalio, “All the Presidents’ Bankers” by Nomi Prins
• Docs: Netflix “Madoff: The Monster of Wall Street,” PBS “The Crash of 2008”
• Tools: SEC Edgar filings, FINRA Investor Education

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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.

• 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?

• 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.

Is modern America built on separating people from their money? Jason and James tackle this provocative question head-on!

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CtrlAltInvest: Resetting the way you think about wealth creation.