Episode 66: Social Investing

Episode 66: Social Investing

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 Follow us on X: https://x.com/HurdleRatePod All episodes now live: https://tnorth.com/shows/hurdle-rate/ 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.

Episode 65: Shifting Institutional

Shifting Institutional | The Hurdle Rate Podcast | Ep. 65 In this week’s Hurdle Rate, the crew opens with updates from Strategy, Strive, and the digital credit market before recapping the major developments from Q2. We cover Strategy’s growing cash reserve, market feedback, and the evolution of Bitcoin-backed credit. We also explore institutional adoption, structured products, AI, intellectual property, and the limits of government intervention in the debt crisis. We close it off with thoughts on outdated financial systems and Bitcoin’s expanding role in traditional capital markets. Here’s the latest with Tim Kotzman, Matt Cole, Jeff Walton, and Ben Werkman. Time Stamps: 0:00 Welcome to The Hurdle Rate 5:19 Digital Credit During Quiet Markets 8:01 Strategy Rebuilds Its Cash Reserve 11:51 Market Uncertainty And Bullish Catalysts 17:21 STRC And Convertible Debt 19:37 AI, The Fed, And Protecting IP 24:14 The U.S. Debt Crisis 31:39 Bitcoin-Backed Institutional Credit 35:30 Building Structured Bitcoin Products 43:12 Growing Institutional Bitcoin Interest 48:02 Stablecoins And Outdated Settlements 53:05 Bitcoin Stewardship And Constructive Engagement 58:29 Closing Thoughts Follow us on X: https://x.com/HurdleRatePod [https://x.com/HurdleRatePod] All episodes now live: https://tnorth.com/shows/hurdle-rate/ [https://tnorth.com/shows/hurdle-rate/] 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.

Episode 64: Building The Track Record

Episode 64: Building The Track Record In this week’s Hurdle Rate, the crew breaks down Strategy’s sale of Bitcoin to fund dividend payments and why the market’s reaction may signal growing confidence in Bitcoin as a liquid capital asset. We explore how Strategy and Strive are using balance sheet management, digital credit, and capital markets access to keep their models moving through volatility. We  also dig into SATA’s short interest, the idea of a “controlled burn,” and how Strive is thinking about protecting shareholders while allowing the market to function. We close with a broader discussion on patience, positioning, and building durable structures in the Bitcoin capital markets era. Here's the latest with Tim Kotzman, Matt Cole, Jeff Walton, and Ben Werkman. Time Stamps: 00:00 Welcome to the Hurdle Rate 03:20 Why Selling Bitcoin Helps STRC Confidence 05:37 Matt Cole on Strategy’s Long-Term Move 09:05 Bitcoin Absorbs the Sale 13:53 Bitcoin Liquidity Compared to Real Estate 17:29 Why the Model Still Works Without Capital Markets 19:03 Bitcoin CAGR + Balance Sheet Strength 23:14 Strive’s Dividend Math Compared to Strategy 27:40 SATA Short Interest + “Controlled Burn” 34:20 Jeff Explains Controlled Burns and Wildfire Incentives 41:56 Why Strive May Let SATA Trade Freely 44:05 Patience, Positioning, and Market Discipline 45:07 Closing Thoughts

Episode 63: The Digital Credit Capital Framework

Episode 63: The Digital Credit Capital Framework In this week's Hurdle Rate, the crew opens with the latest on digital credit volatility and the broader market backdrop, before digging into Strategy's capital framework and how management is navigating stress in the system. The conversation turns to institutional behavior, the realities of managing a cash balance sheet, and the dynamics of leverage and short interest within digital credit. We unpack high yield investing perspectives, what resilience and company DNA actually look like in this market, and the specific investor protections built into SATA. We close with reflections on what it takes to build durable structures in the digital credit era.

Episode 62: Digital Credit Weakness

Episode 62: Digital Credit Weakness Full episodes: https://tnorth.com/hurdle-rate/ [https://tnorth.com/hurdle-rate/] In this week's Hurdle Rate, the crew breaks down the mechanics of volatility and liquidation events, before turning to shifting investor behavior and how markets react to sudden liquidations. We dig into how digital credit stacks up against traditional financial instruments, the innovations shaping the future of the lending landscape, and what it takes for protocols to remain resilient in brutal bear markets. We close with a deeper look at the Federal Reserve, the opinions surrounding Kevin Warsh, and why navigating economic uncertainty requires a unique strategy for the anticipated super cycle ahead. Here’s the latest with Tim Kotzman, Matt Cole, Jeff Walton, and Ben Werkman. 00:00 - Welcome To The Hurdle Rate 06:24 - Analyzing Volatility and Liquidation Events 11:28 - Understanding Market Reactions and Investor Behavior 17:23 - Comparing Digital Credit to Traditional Financial Instruments 22:11 - The Future of Digital Credit and Market Innovations 30:52 - Resilience in Bear Markets 36:07 - Opinions on Kevin Warsh and the Fed 41:48 - Navigating Economic Uncertainty 51:53 - Optimism for a Super Cycle