Skippy and Doogles Talk Investing

Skippy & Doogles take on the $40B youth sports industrial complex, the myth of "smart money," and why partying might actually be dead in America. From private equity buying baseball fields to billionaires going broke, this episode unpacks the psychology behind bad investments—financial and social. Plus, we dive into Victor Haghani's “The Missing Billionaires” and what most financial advice gets totally wrong. Join the Skippy and Doogles fan club [https://skippydoogles.supercast.com/]. You can also get more details about the show at skippydoogles.com [http://skippydoogles.com/], show notes on our Substack [https://skippydoogles.substack.com/], and send comments or questions to skippydoogles@gmail.com [skippydoogles@gmail.com].

Skippy & Doogles dig into the fine print of the “Trump Accounts” and discover… it’s not what the headlines promised. Is it an investing tool or just legislative cosplay? Then they hit the gas on private equity performance myths and finish strong with a discussion on incentivized stupidity—from lawn chairs and balloons to CEOs pumping their own stock. Join the Skippy and Doogles fan club [https://skippydoogles.supercast.com/]. You can also get more details about the show at skippydoogles.com [http://skippydoogles.com/], show notes on our Substack [https://skippydoogles.substack.com/], and send comments or questions to skippydoogles@gmail.com [skippydoogles@gmail.com].

Skippy and Doogles are back in your mentals with a triple-header of investing greatness. First up, a stablecoin thought experiment gone dark—what if Circle succeeds too much? Then, Cloudflare’s CEO drops jaw-dropping data on how AI is nuking the internet’s original traffic model. Finally, we break down two blog posts on venture fund returns—including Y Combinator's staggering 6,000x win with Airbnb. Plus: Amazon’s long shadow over local business and why Skippy might owe central banks an apology. Join the Skippy and Doogles fan club [https://skippydoogles.supercast.com/]. You can also get more details about the show at skippydoogles.com [http://skippydoogles.com/], show notes on our Substack [https://skippydoogles.substack.com/], and send comments or questions to skippydoogles@gmail.com [skippydoogles@gmail.com].

This week, Skippy & Doogles break down the real risks (and hype) around stablecoins — why they’re booming, what regulators just did, and why most “innovations” here just rebuild the same old financial system. Plus: how to think clearly when your investment 10X’s overnight (and why that’s often a red flag). Join the Skippy and Doogles fan club [https://skippydoogles.supercast.com/]. You can also get more details about the show at skippydoogles.com [http://skippydoogles.com/], show notes on our Substack [https://skippydoogles.substack.com/], and send comments or questions to skippydoogles@gmail.com [skippydoogles@gmail.com].

This week, we break down the Circle IPO frenzy — is this stablecoin stock the next big thing or pure speculation? 🚀 Then we dive into the new tip tax law and why it’s creating unexpected winners and losers. Finally, we explore America’s adulting crisis: why are so many young adults Googling “how to use a mop”? 🤯 Topics covered: * Circle Internet Group (CRCL) IPO: is the hype justified? * The surprising math behind “no taxes on tips” * Why basic life skills are trending on Google * Listener mail: when should startup founders hire a finance pro? Join the Skippy and Doogles fan club [https://skippydoogles.supercast.com/]. You can also get more details about the show at skippydoogles.com [http://skippydoogles.com/], show notes on our Substack [https://skippydoogles.substack.com/], and send comments or questions to skippydoogles@gmail.com [skippydoogles@gmail.com].