Success in Asset Tokenization: Why Treasuries Outshine Real Estate

In this episode of 'Old Men New Money,' Ali Davoudi explores the robust success of tokenized treasuries compared to the struggling attempts in real estate tokenization. He highlights the simplicity, liquidity, and regulatory clarity that make treasuries an ideal candidate for tokenization. By reviewing major players like BlackRock and Franklin Templeton, Davoudi explains the benefits, business models, and future growth of tokenized treasuries within the financial ecosystem. He also addresses key risks and provides practical advice for potential investors, emphasizing the lessons learned and future potential in tokenizing other asset classes.

00:00 Introduction to Tokenized Treasuries

00:51 What Are Tokenized Treasuries?

01:59 Why Tokenized Treasuries Succeed

03:32 Key Players in Tokenized Treasuries

05:13 Use Cases for Tokenized Treasuries

06:55 Economics for Asset Managers

09:20 Risks and Considerations

10:41 Personal Take and Future Predictions

13:06 Lessons for Other Asset Classes

16:21 Closing Thoughts and Next Episodes

The Truth About Real Estate Tokenization: Why It Hasn't Worked and What Needs to Change

In this episode of Old Men New Money, Ali Davoudi introduces the audience to module four of their educational series on digital securities, focusing on real world asset tokenization, specifically real estate. Ali explains why real estate tokenization, despite its exciting pitch of liquidity and fractional ownership, has largely failed due to regulatory complexities, liquidity illusions, and unclear value propositions. He offers insights into current approaches and suggests practical changes that could make real estate tokenization viable, such as focusing on tokenizing real estate funds or REITs and being honest about liquidity. Ali also shares lessons applicable to other asset classes and previews upcoming episodes covering tokenized treasuries, public equity, and private equity.

00:00 Introduction to Module Four: Real World Asset Tokenization

00:56 The Hype and Promise of Real Estate Tokenization

02:09 Why Real Estate Tokenization Has Failed

04:13 Structural Challenges in Real Estate Tokenization

05:57 Examples of Failed Tokenization Projects

07:52 What Needs to Change for Real Estate Tokenization to Succeed

09:49 Potential Models for Successful Tokenization

14:17 Lessons for Tokenizing Other Asset Classes

15:32 Investor Advice and Looking Ahead

18:08 Conclusion and Future Topics

Understanding the Risks of Investing in Treasury Companies

In the latest episode of Old Men New Money, Douglas Borthwick delves into the various risks associated with investing in corporate treasury companies that are heavily involved in crypto assets. The episode covers seven major risk categories including asset price risk, NAV premium compression, dilution, debt leverage, regulatory issues, key person risk, and execution risk. Borthwick emphasizes the importance of understanding and managing these risks, especially in volatile market conditions, and provides guidance on position sizing, monitoring metrics, and establishing clear exit rules. He also cautions against treating these investments as conservative or core holdings, recommending them only for those with high risk tolerance and speculative capital.

00:00 Introduction to Corporate Treasury Strategies

00:45 Understanding Major Risk Categories

02:37 Asset Price Risk Explained

04:14 NAV Premium Compression

05:46 Dilution Risks

06:56 Debt and Leverage Risks

08:14 Regulatory and Legal Risks

09:36 Key Person Risk

10:46 Execution Risk

12:20 Competition and Technological Disruption

15:23 Managing Risks and Position Sizing

16:30 Who Should and Shouldn't Invest

18:09 Final Thoughts and Next Module Preview

Understanding SOL Strategies: The Future of Treasury Companies

In this episode of 'Old Men New Money,' Douglas Borthwick explores SOL Strategies (ticker: STKE), a pioneering Solana Treasury company that goes beyond simple asset accumulation. Unlike other treasury companies, SOL Strategies also operates validator infrastructure, earning fees from institutional clients and building a recurring revenue business. They manage over 3.6 million SOL and provide staking services for major institutions like ARC Invest and VanEck. The episode delves into their revenue streams, including staking yield, validator fees, and purchasing locked SOL at a 15% discount from the Solana Foundation. Borthwick also discusses why Solana's high throughput and low-cost blockchain make it the ideal platform for institutional applications. The episode concludes with an analysis of risks and strategic advantages, positioning SOL Strategies as a model for the future of treasury companies.

00:00 Introduction to SOL Strategies

00:48 Overview of SOL Strategies

06:28 Revenue Streams Explained

08:19 Validator Economics and Operations

12:02 Institutional Partnerships and Clients

15:36 Risks and Challenges

19:18 Conclusion and Next Steps

Bitmine's Ambitious Ethereum Accumulation Strategy Explained

In this episode of Old Men New Money, host Douglas Borthwick delves into Bitmine's strategic pivot from Bitcoin mining to becoming the world's largest Ethereum treasury. Led by Tom Lee of Fundstrat, Bitmine aims to accumulate 5% of all Ethereum by leveraging capital markets and staking ETH for yield. This episode examines the differences between Bitcoin and Ethereum as assets, Bitmine's innovative immersion cooling technology, and the company's ambitious goal to position itself as a primary counterparty for institutional Ethereum transactions. The episode also highlights the risks involved and compares Bitmine's model to MicroStrategy's Bitcoin accumulation approach.

00:00 Introduction to Corporate Treasury Strategies

00:19 Bitmine's Bold Ethereum Strategy

01:10 Tom Lee's Vision and Strategic Pivot

01:43 Ethereum's Supercycle and Institutional Adoption

03:14 Bitmine's Accumulation and Staking Strategy

08:19 Liquidity and Market Position

09:09 Valuation and Future Prospects

13:37 Risks and Comparisons

15:59 Conclusion and Next Episode Preview

Understanding Treasury Companies: The Strategy Playbook

In this episode of Old Men New Money, Douglas Borthwick introduces module three of the educational series, focusing on treasury companies that use their corporate balance sheets to accumulate crypto assets, primarily Bitcoin. Borthwick explores the pioneering case of MicroStrategy, now called Strategy, which began converting its corporate treasury into Bitcoin in August 2020. The episode details Strategy’s financial engineering tactics, their Bitcoin yield metrics, and the associated risks. It also discusses the broader market implications, highlighting how over 70 public companies have adopted similar strategies. The episode concludes by emphasizing the critical role of Bitcoin’s price trajectory in the success of these treasury companies.

00:00 Introduction to Module Three

00:14 The Rise of Treasury Companies

00:36 MicroStrategy's Bold Move

01:16 Understanding the Strategy Playbook

04:21 Financial Engineering and Bitcoin Yield

09:32 Valuation and Market Dynamics

17:42 Risks and Considerations

22:53 Conclusion and Next Steps

Demystifying Digital Wallets and Key Management

In this episode of Old Men New Money, Douglas Borthwick addresses the fears traditional investors have about digital securities, specifically focusing on private keys and digital wallets. He explains the importance of digital wallets, how custody works, and why security tokens offer safety advantages over pure cryptocurrencies. Douglas clarifies key concepts such as hot and cold wallets, seed phrases, and multisignature wallets, providing insights on the security and practicality of each option. He also discusses the regulatory landscape for digital asset custody, the role of custodians, and the future developments in the field. Key takeaways include understanding the critical nature of seed phrases, practicing wallet setup, and considering custodial versus non-custodial solutions.

00:00 Introduction to Digital Securities

00:51 Understanding Digital Wallets

03:21 Hot Wallets vs Cold Wallets

05:47 The Importance of Seed Phrases

07:00 Custodial vs Non-Custodial Wallets

09:31 Multisig Wallets for Institutional Custody

10:25 Common Mistakes and Best Practices

11:32 Popular Wallet Options

12:45 Regulatory Perspective on Custody

14:53 Future of Digital Custody

16:04 Practical Steps for Secure Custody

16:58 Conclusion and Next Steps

Stablecoins: The Unsung Heroes of Digital Finance

In this episode of 'Old Men New Money,' Douglas Borthwick delves into the significance of stablecoins—cryptocurrencies pegged to stable assets like the US dollar. With over $284 billion in circulation as of October 2025, stablecoins are revolutionizing financial transactions by providing instant, low-cost, 24/7 global transfers. Borthwick explains how stablecoins like USDT, USDC, PY Dollar, and DAI operate, their regulatory landscapes, and their crucial role in digital securities and decentralized finance (DeFi). He highlights the advantages of stablecoins over traditional banking methods, their growing adoption by major institutions like PayPal and Visa, and the potential risks and future of stablecoins in the financial ecosystem.

00:00 Introduction to Stable Coins

00:44 What Are Stable Coins?

03:25 The Main Players in Stable Coins

05:23 How Stable Coins Maintain Their Value

06:56 Stable Coins in Digital Securities

08:24 Regulation and Compliance

09:47 Stable Coins in Decentralized Finance (DeFi)

10:54 The Growing Adoption of Stable Coins

13:36 Potential Risks and Challenges

15:00 Central Bank Digital Currencies (CBDCs)

16:03 Practical Steps and Conclusion

Ethereum vs. Solana: The Future of Tokenized Equity

In this episode of 'Old Men New Money,' Douglas Borthwick discusses the major infrastructure decision in digital securities: Ethereum versus Solana. He highlights Galaxy Digital's choice to tokenize NASDAQ-listed shares on Solana, marking a significant shift from Ethereum due to Solana's high performance and lower costs. Borthwick argues that while Ethereum has institutional credibility and regulatory comfort, it falls short in terms of transaction speed and cost compared to Solana. He provides a detailed comparison of the two blockchains, emphasizing Solana's advantages for high-frequency trading and consumer-facing applications. Borthwick concludes that trends in developer migration and transaction volume favor Solana, marking it as the future leader in smart contract platforms. The episode also teases a future discussion on stablecoins.

00:00 Introduction to the Debate: Ethereum vs. Solana

00:12 Galaxy Digital's Groundbreaking Move

00:58 Ethereum vs. Solana: A Performance Comparison

02:26 The Regulatory Shift and Its Implications

04:42 Ethereum's Struggles in High-Frequency Markets

05:27 Why Solana is the Future for High Throughput Applications

06:31 Developer Migration to Solana

07:36 Solana's Real-World Usage and Efficiency

09:48 The Layer Two Debate and Solana's Unified Approach

10:40 Ethereum's Strengths and Limitations

11:42 Solana's Security and Network Stability

14:19 Future Predictions and Strategic Advice

18:07 Conclusion and Next Episode Preview

Blockchain Basics: Understanding the Technology that Powers Digital Securities

In this episode of Old Men New Money, Douglas Borthwick begins module two of the educational series on digital securities, focusing on blockchain technology. He explains what a blockchain is, its security features, and the differences between public and private blockchains. The episode covers the benefits of blockchain for finance, including instant settlement, fractional ownership, and programmable compliance. Borthwick emphasizes the importance of understanding the technology as major financial institutions implement blockchain strategies. He also discusses the economic models of various blockchains and highlights their adoption and risks. The concluding advice urges finance professionals to gain hands-on experience and follow thought leaders in the blockchain space.

00:00 Introduction to Module Two: Blockchain Technology

00:53 Understanding Blockchain Basics

01:38 The Importance of Blockchain in Finance

02:32 How Blockchain Settlement Works

03:39 Detailed Explanation of Blockchain Mechanics

06:16 Public vs. Private Blockchains

07:47 Smart Contracts and Their Impact

09:05 Blockchain's Advantages for Digital Securities

10:46 Decentralization and Its Significance

13:34 Performance and Scalability of Blockchains

15:00 Consensus Mechanisms Explained

16:11 Current Blockchain Adoption and Statistics

17:15 Risks and Challenges of Blockchain

18:22 Practical Steps to Engage with Blockchain

19:31 Conclusion and Next Episode Preview