The Hurdle Rate Podcast

Episode 66: Social Investing


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In this week’s Hurdle Rate, the crew breaks down the slow summer market and strategy's focus on building up its balance sheet to improve credit quality. We explore how Strategy and Strive are navigating macro uncertainty, steadying operations, and executing consistent Bitcoin buys through the summer doldrums. We also dig into the derivatives market, short interest dynamics for ASST and SATA, and how lending out shares ultimately impacts corporate dividend payments and tax treatment. We close with a broader discussion on structured finance, the emergence of AI agents in retail investing, and the long-term potential of building durable digital credit structures to onboard massive institutional capital into the Bitcoin era.

Here’s the latest with Tim Kotzman, Matt Cole, Jeff Walton, and Ben Werkman.

Timestamps:

00:00 – Welcome Back to the Hurdle Rate
11:09 – Trading Volumes: MSTR vs. IBIT
12:33 – Analysis of Short Interest & Derivatives Markets
16:04 – Tax Treatments for Lending Shares & Manufactured Dividends
20:10 – Short Squeezes & Conserved Energy in Equities
28:49 – Robinhood Retail AI Trading Agents
30:00 – Deconstructing Chamath’s Crypto Tweet
31:59 – Unlocking Institutional & Corporate Demand for Bitcoin
32:52 – Private Credit Markets, Structured Finance & Insurers
51:50 – Step Function Improvements in Leverage Solutions
56:28 – Battle Testing Management Teams & Risk-First Approaches

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Disclaimer: The content in this video is for informational and educational purposes only and should not be considered financial advice. We are not financial advisors, and you should consult with a qualified professional before making any financial decisions. All investments involve risks, and you are responsible for your own decisions.

True North does not intend for anything herein to be considered an offer or sale of any securities, including those of Strive. True North encourages listeners to consult with their tax and investment advisors. Additional information on any securities or issuers referenced herein can be found in such issuers’ filings with the Securities and Exchange Commission (“SEC”), including any registration statements, prospectuses and prospectus supplements for each issuers’ securities. Listeners should read such documents and other documents incorporated by reference therein or that such issuer has filed with the SEC for more complete information. You may get these documents for free by visiting EDGAR on the SEC website at [www.sec.gov](http://www.sec.gov).*

Any securities referred to herein, including those of True North’s parent Strive, are not collateralized by underlying bitcoin holdings and may be subordinated to senior claims. There are no guarantee of returns liquidity or future performance. The securities referred to herein are neither bank deposits, nor FDIC insured, nor regulated in the same way, and do not have the same regulatory and other protections as bank accounts, money market funds, treasuries, or similar investments and as a result may not be comparable investments. Current trading prices and effective yields may vary, current rates are not indicative of future rates, and in some cases rates are subject to frequent adjustments and may be significantly lower than discussed herein. Cash dividends are not guaranteed. In some cases, dividends have not been paid and may not be paid in the future. Ownership of securities referred to in herein does not confer ownership in the underlying assets, including bitcoin.

 

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