

Old Men, New Money®: Bitcoin, Blockchain & Tokenization
Douglas Borthwick, Phil Larmon and Ali Davoudi
The Authority's Guide to Tokenization & Digital Assets. Tired of crypto advice from influencers who've never executed a real securities offering? Douglas Borthwick (pioneer of the first SEC-registered security token IPO), Phil Larmon, and Ali Davoudi bring decades of Wall Street experience to blockchain innovation—and they're not here to sell you the latest memecoin. What makes us different: Douglas made history raising $85 million in the world's first regulated token IPO. We've survived multiple market crashes, built real wealth through traditional investing, and now we're showing how tokenization reshapes serious portfolios. No hype. Just the creator of the "Insumer Model" asking questions crypto Twitter won't. Every episode delivers: Exclusive interviews with industry pioneers (not Twitter personalities), Real tokenization opportunities from someone who's actually executed them
Security token strategies that work within regulatory frameworks, Market analysis from the author of 5 blockchain books. Perfect for: Executives and institutional investors exploring tokenization without the learning curve. If you're making real investment decisions, this show is for you. Recent guests include: Samson Mow, former FTX executives, and entertainment industry pioneers. New episodes every Tuesday. Subscribe and join 13,000+ investors learning from the person who literally wrote the book on tokenization. Warning: We occasionally reference SEC filings and things before Bitcoin existed. oldmennewmoney.substack.com
Security token strategies that work within regulatory frameworks, Market analysis from the author of 5 blockchain books. Perfect for: Executives and institutional investors exploring tokenization without the learning curve. If you're making real investment decisions, this show is for you. Recent guests include: Samson Mow, former FTX executives, and entertainment industry pioneers. New episodes every Tuesday. Subscribe and join 13,000+ investors learning from the person who literally wrote the book on tokenization. Warning: We occasionally reference SEC filings and things before Bitcoin existed. oldmennewmoney.substack.com
Episodes
Mentioned books

Nov 21, 2025 • 17min
Episode 16: Private Equity Tokenization: Democratizing Alternative Assets
Unlocking Private Equity: The Future of TokenizationIn this final episode of Module Four on Real World Asset Tokenization, Ali Davoudi discusses the transformative potential of private equity tokenization. He explains why private equity matters, highlighting its $10 trillion global value but noting that access is limited to accredited investors. Ali explores three models for tokenizing private equity: tokenizing fund shares, direct investments in private companies, and secondary markets for existing stakes. He delves into the challenges, such as regulatory compliance and governance, and shares examples of successful implementations. He also provides practical advice for investors, underscoring the importance of understanding underlying investments, evaluating platforms, and reading legal documents. Ali concludes with his vision for the next decade, outlining a future where tokenization could democratize access and improve liquidity in private markets.00:00 Introduction to Private Equity Tokenization00:52 Why Private Markets Matter02:18 Approaches to Tokenizing Private Equity03:46 Tokenizing Private Equity Funds05:17 Direct Tokenization of Private Companies06:42 Secondary Markets for Private Equity07:59 Regulatory Challenges09:23 Personal Insights on Private Investing10:22 Success Stories and Future Vision12:52 Lessons from Real World Asset Tokenization14:08 Investor's Guide to Tokenized Private Equity15:37 Connecting to the Next Module16:21 Closing Thoughts Get full access to Bitcoin, Blockchain and Tokenization at oldmennewmoney.substack.com/subscribe

Nov 20, 2025 • 17min
Episode 15: Tokenizing Public Equity: The Next Frontier
Exploring Tokenization of Public Equity: Innovations and ChallengesIn this episode of Old Men New Money, Ali Davoudi discusses the emerging trend of tokenizing public company shares, illustrating how it could reshape global equity markets. He explains the difference between direct tokenization (as done by Galaxy Digital) and wrapped tokenization (as pursued by Backed and INX). Ali dives into the benefits, such as 24/7 trading and instant settlement, but also outlines challenges such as liquidity fragmentation and regulatory complexity. Through detailed examination, he balances the potential advantages against the current practical challenges and provides insights into the future of tokenized public equity, comparing it to the early internet era. Finally, he previews the next episode, which will focus on the potential of private equity tokenization.00:00 Introduction to Tokenized Public Equity00:45 Understanding Public Equity Tokenization00:58 Direct vs. Wrapped Tokenization Models01:58 Galaxy Digital's Innovative Move03:26 The Wrapped Tokenization Model04:52 Value Propositions of Tokenized Equity06:27 Challenges of Tokenized Public Equity07:57 Personal Views and Predictions11:40 Lessons from Real World Asset Tokenization13:02 Investor Guidance on Tokenized Public Equity14:28 Connecting to Private Equity Tokenization15:21 Closing Thoughts Get full access to Bitcoin, Blockchain and Tokenization at oldmennewmoney.substack.com/subscribe

Nov 19, 2025 • 18min
Episode 14: Tokenized Treasuries: Blackrock's BUIDL and Beyond
Success in Asset Tokenization: Why Treasuries Outshine Real EstateIn 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 Treasuries00:51 What Are Tokenized Treasuries?01:59 Why Tokenized Treasuries Succeed03:32 Key Players in Tokenized Treasuries05:13 Use Cases for Tokenized Treasuries06:55 Economics for Asset Managers09:20 Risks and Considerations10:41 Personal Take and Future Predictions13:06 Lessons for Other Asset Classes16:21 Closing Thoughts and Next Episodes Get full access to Bitcoin, Blockchain and Tokenization at oldmennewmoney.substack.com/subscribe

Nov 17, 2025 • 19min
Episode 13: Real Estate Tokenization: Lessons Learned and Future Directions
The Truth About Real Estate Tokenization: Why It Hasn't Worked and What Needs to ChangeIn 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 Tokenization00:56 The Hype and Promise of Real Estate Tokenization02:09 Why Real Estate Tokenization Has Failed04:13 Structural Challenges in Real Estate Tokenization05:57 Examples of Failed Tokenization Projects07:52 What Needs to Change for Real Estate Tokenization to Succeed09:49 Potential Models for Successful Tokenization14:17 Lessons for Tokenizing Other Asset Classes15:32 Investor Advice and Looking Ahead18:08 Conclusion and Future Topics Get full access to Bitcoin, Blockchain and Tokenization at oldmennewmoney.substack.com/subscribe

Nov 14, 2025 • 21min
Episode 12: Treasury Companies: Risks You Need to Understand
Understanding the Risks of Investing in Treasury CompaniesIn 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 Strategies00:45 Understanding Major Risk Categories02:37 Asset Price Risk Explained04:14 NAV Premium Compression05:46 Dilution Risks06:56 Debt and Leverage Risks08:14 Regulatory and Legal Risks09:36 Key Person Risk10:46 Execution Risk12:20 Competition and Technological Disruption15:23 Managing Risks and Position Sizing16:30 Who Should and Shouldn't Invest18:09 Final Thoughts and Next Module Preview Get full access to Bitcoin, Blockchain and Tokenization at oldmennewmoney.substack.com/subscribe

Nov 13, 2025 • 20min
Episode 11: Sol Strategies: The Infrastructure Revenue Model
Understanding SOL Strategies: The Future of Treasury CompaniesIn 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 Strategies00:48 Overview of SOL Strategies06:28 Revenue Streams Explained08:19 Validator Economics and Operations12:02 Institutional Partnerships and Clients15:36 Risks and Challenges19:18 Conclusion and Next Steps Get full access to Bitcoin, Blockchain and Tokenization at oldmennewmoney.substack.com/subscribe

Nov 12, 2025 • 18min
Episode 10: The Ethereum Treasury Model: BitMine's Bold Bet
Bitmine's Ambitious Ethereum Accumulation Strategy ExplainedIn 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 Strategies00:19 Bitmine's Bold Ethereum Strategy01:10 Tom Lee's Vision and Strategic Pivot01:43 Ethereum's Supercycle and Institutional Adoption03:14 Bitmine's Accumulation and Staking Strategy08:19 Liquidity and Market Position09:09 Valuation and Future Prospects13:37 Risks and Comparisons15:59 Conclusion and Next Episode Preview Get full access to Bitcoin, Blockchain and Tokenization at oldmennewmoney.substack.com/subscribe

Nov 10, 2025 • 25min
Episode 9: Treasury Companies 101: The MicroStrategy Playbook
Understanding Treasury Companies: The Strategy PlaybookIn 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 Three00:14 The Rise of Treasury Companies00:36 MicroStrategy's Bold Move01:16 Understanding the Strategy Playbook04:21 Financial Engineering and Bitcoin Yield09:32 Valuation and Market Dynamics17:42 Risks and Considerations22:53 Conclusion and Next Steps Get full access to Bitcoin, Blockchain and Tokenization at oldmennewmoney.substack.com/subscribe

Nov 6, 2025 • 19min
Episode 8: Wallets, Private Keys, and Digital Custody
Demystifying Digital Wallets and Key ManagementIn 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 Securities00:51 Understanding Digital Wallets03:21 Hot Wallets vs Cold Wallets05:47 The Importance of Seed Phrases07:00 Custodial vs Non-Custodial Wallets09:31 Multisig Wallets for Institutional Custody10:25 Common Mistakes and Best Practices11:32 Popular Wallet Options12:45 Regulatory Perspective on Custody14:53 Future of Digital Custody16:04 Practical Steps for Secure Custody16:58 Conclusion and Next Steps Get full access to Bitcoin, Blockchain and Tokenization at oldmennewmoney.substack.com/subscribe

Nov 5, 2025 • 18min
Episode 7: Stablecoins: The Bridge Between TradFi and Crypto
Discover the fascinating world of stablecoins and their pivotal role in digital finance. These cryptocurrencies, pegged to stable assets, enable instant and low-cost global transactions. Learn about the major players like USDT and USDC, and how they maintain their value through innovative mechanisms. Explore their significance in decentralized finance and tokenized securities, alongside the regulatory challenges they face. With insights into adoption by institutions and potential risks, this discussion showcases stablecoins as the future of finance.


