Skippy and Doogles Talk Investing

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June 2025

Skippy & Doogles Weekly: Can Success Kill a Startup? Plus, YC’s Insane Returns & AI’s Internet Takeover
Circle’s stablecoin dream may be doomed by its own ambition. Plus: Cloudflare’s AI bombshell & why YC’s 6,000x wins are rare for a reason.
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Skippy & Doogles
Skippy & Doogles Weekly: Circle IPO Mania, Tip Tax Madness & Why Nobody Can Adult Anymore
This week: Circle’s wild IPO, the real winners of tip tax reform, and why Google is teaching us to adult.
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Skippy & Doogles

May 2025

Skippy & Doogles Weekly: Hidden Costs of Investing
Basic Capital wants to 5x your 401(k). Sounds brilliant—until you see the 0.5%, the 6.26%, the 5%, and the monthly fee. We break it all down.
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Skippy & Doogles
Skippy & Doogles Weekly: Is Buffett Really the GOAT?
Buffett’s the GOAT? Maybe. Maybe not. This episode unpacks the myth, the money, and the man.
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Skippy & Doogles
Skippy & Doogles Weekly: McRecession, Meet Reality
The economy’s weird, fast food’s expensive, and jobs are vanishing.
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Skippy & Doogles

April 2025

📨 Skippy & Doogles Weekly: Student Debt, Private Equity Panic, and Market Madness
Yale’s $6B move, student debt chaos, and YOLO investing makes a comeback.
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Skippy & Doogles
Skippy & Doogles Weekly: Foreigners Own $30 Trillion in U.S. Assets — Should We Be Nervous?
China’s calling itself a “safe haven,” private equity’s in trouble, and global capital might be heading for the exit. Skippy & Doogles break it all…
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Skippy & Doogles
Skippy and Doogles Weekly: Compounding in Chaos — How We’re Investing Anyway
Charlie Munger said never interrupt compounding unnecessarily. But what if the world’s on fire? We break down tariffs, bond market panic, and how to…
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Skippy & Doogles
Skippy and Doogles Weekly: Why the Market Tanked, and What Penguins Have to Do With It
Trump’s new tariff plan sparked market chaos, global backlash, and memes featuring penguins in suits.
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Skippy & Doogles

March 2025

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