

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

Oct 30, 2025 • 26min
Episode 4: Unmasking the Unseen: The Infrastructure Powering Digital Securities
The Critical Role of Infrastructure in Digital SecuritiesIn this episode of Old Men New Money, Douglas Borthwick discusses the often-overlooked but essential role of infrastructure in the digital securities market. He emphasizes the importance of alternative trading systems, transfer agents, and custodians in ensuring the smooth functioning of digital securities. Douglas draws from his experience at INX to explain how they built their own infrastructure to support digital assets, including the acquisition of Open Finance and Tokensoft's transfer agent. He explains the different custody models, the role of transfer agents in maintaining accurate records and compliance, and the challenges ATSs face in achieving liquidity. The episode concludes with an outlook for the future of digital securities infrastructure and practical advice for issuers and investors. This comprehensive discussion highlights the critical importance of robust infrastructure in the success and growth of the digital securities market.00:00 Introduction to Digital Securities Infrastructure00:10 The Importance of Infrastructure in Digital Securities00:44 Building the Necessary Infrastructure01:09 Critical Components of Digital Securities Infrastructure03:20 Custody Models and Providers07:08 Role of Transfer Agents10:41 Trading Venues and Market Liquidity15:39 Global Developments and Regulatory Landscape20:00 Future of Digital Securities Infrastructure21:15 Practical Advice for Issuers and Investors24:10 Conclusion and Future Modules Get full access to Bitcoin, Blockchain and Tokenization at oldmennewmoney.substack.com/subscribe

Oct 29, 2025 • 20min
Episode 3: Demystifying Security Token Offerings: The Real Process Behind the Buzz
The Complete Guide to Security Token Offerings (STOs): Costs, Process, and PitfallsIn this episode of Old Men, New Money, Douglas Borthwick demystifies the intricate process of Security Token Offerings (STOs). He details the entire journey from planning to execution, highlighting key parties involved: issuers, securities lawyers, blockchain developers, transfer agents, broker dealers, and custody providers. The episode breaks down costs, timelines, and common pitfalls that companies face. Borthwick draws from his experience at INX, providing practical insights into legal documentation, smart contract creation, investor relations, and compliance. The episode serves as a comprehensive guide for companies considering STOs, underlining the importance of professional execution.00:00 Introduction to Security Token Offerings00:14 Understanding the STO Process02:02 Key Players in an STO04:44 Detailed Breakdown of the STO Timeline13:48 Common Mistakes and How to Avoid Them15:31 Successful STO Case Study: INX17:17 Practical Advice for STOs19:05 Conclusion and Next Steps Get full access to Bitcoin, Blockchain and Tokenization at oldmennewmoney.substack.com/subscribe

Oct 28, 2025 • 15min
Episode 2: Navigating the Regulatory Landscape: A Must-Know for Digital Securities
Navigating the Regulatory Maze for Digital Securities: Reg D, Reg S, and Reg CF ExplainedIn this episode of 'Old Men New Money,' Douglas Borthwick delves into the complexities of regulatory frameworks surrounding digital securities. Focused on SEC's Reg D, Reg S, and Reg CF, Borthwick highlights the importance of understanding these regulations to avoid financial losses. He shares insights from his experience at INX, discussing the challenges and benefits of complying with these exemptions. The episode covers the specifics of each regulation, reporting requirements, resale restrictions, and common mistakes companies make. This foundational understanding is crucial for investors and founders to navigate the evolving landscape of digital securities successfully.00:00 Introduction to Regulatory Roadmap00:27 Importance of Understanding Regulations01:10 Overview of Regulatory Exemptions03:26 Deep Dive into Reg D05:52 Exploring Reg S07:09 Understanding Reg CF08:00 Full Registration Process09:09 Compliance and Common Mistakes12:00 Future of Digital Securities Regulations12:47 Practical Advice for Investors and Founders13:35 Conclusion and Next Episode Preview Get full access to Bitcoin, Blockchain and Tokenization at oldmennewmoney.substack.com/subscribe

Oct 27, 2025 • 15min
Episode 1: What Are Digital Securities? (And Why They're Not Crypto)
Understanding Digital Securities: Distinguishing from CryptoIn this episode of Old Men New Money, Douglas Borthwick clarifies the crucial differences between digital securities and cryptocurrencies, dispelling common misconceptions. Drawing from his experience as Chief Business Officer at INX, Borthwick explains how digital securities represent actual securities like stocks and bonds on the blockchain, regulated by the SEC, unlike cryptocurrencies which are considered commodities. He discusses the advantages of digital securities, including instant settlement, 24/7 markets, and legal protections, citing examples from key industry players like BlackRock, Galaxy Digital, and INX. Borthwick also highlights the potential growth and challenges within the space, emphasizing the need for education and adaptation in the traditional finance sector.00:00 Introduction to Digital Securities00:42 Understanding Digital Securities vs. Cryptocurrencies02:52 Types of Blockchain Tokens04:20 The Howey Test and Security Tokens06:04 The Advantages of Digital Securities07:15 Real-World Examples and Success Stories09:16 The Future of Digital Securities09:55 Risks and Challenges in Digital Securities11:14 Traditional Finance vs. Blockchain13:04 Actionable Steps and Conclusion Get full access to Bitcoin, Blockchain and Tokenization at oldmennewmoney.substack.com/subscribe

Oct 19, 2025 • 17min
Solana vs Ethereum: The Financial Market Game Changer
The discussion dives into Galaxy Digital's groundbreaking decision to tokenize on Solana, highlighting a major shift in blockchain use. Solana boasts processing 40 times more transactions than Ethereum at a fraction of the cost. With Solana attracting more developers and better performance metrics, the conversation emphasizes the looming trillion-dollar mistake made by traditional finance in favoring brand recognition over technical superiority. Insights into Solana's efficiency, network revenue, and the potential for institutional migrations are shared.

Oct 17, 2025 • 19min
Bitcoin, Ethereum & Solana Treasury Companies Compared
Douglas Borthwick dives into the fascinating world of corporate cryptocurrency treasuries. He discusses how MicroStrategy led the charge in Bitcoin investment, while Bitmine rapidly pivoted to Ethereum, leveraging yields through staking. Sol Strategies capitalizes on Solana with impressive staking yields and unique advantages. The episode highlights the strategic differences between these companies, their risks, and the benefits of choosing corporate treasury over direct crypto investments. It's a must-listen for anyone curious about the future of corporate finance in the crypto space.

Oct 15, 2025 • 11min
Breaking Down Solana: Speed, Scale, and Success in Crypto
Explore Solana's groundbreaking blockchain technology, likening it to the 1800s railroad boom in terms of efficiency and reliability. Discover how SOL fuels transactions and the critical role of validators in maintaining the network. Learn how everyday users can buy and stake SOL for passive income while navigating the risks of crypto volatility. Delve into Solana's robust performance metrics and its vast applications from decentralized exchanges to NFTs, illustrating its essential place in the evolving blockchain ecosystem.

Aug 8, 2025 • 49min
Navigating the Future of Digital Securities: An In-Depth Conversation
Digital Securities and Consumer Equity: The Revolution and RisksIn this episode, Phil Larmon, Ali Davoudi, and Douglas Borthwick discuss the implications of the new Genius Act and Clarity Act on the economy, specifically focusing on the rise of digital securities and consumer equity - What ouglas calls The Insumer Model. They delve into the potential for stablecoins and digital wallets becoming ubiquitous, transforming how consumers and investors interact. The conversation touches on issues of interoperability among digital security platforms, potential benefits for shareholders in consumer loyalty models, and the challenges and risks companies might face in implementing such systems. Concerns about privacy, liability, and the feasibility of peer-to-peer trading without intermediary platforms are debated, highlighting the complex landscape and the need for more thorough discussion and planning.00:00 Introduction and Episode Kickoff00:56 The Impact of the Genius Act and Clarity Act01:58 Understanding Digital Securities and Consumer Models02:26 Practical Applications and Benefits of Digital Securities05:01 Challenges and Considerations in Digital Securities05:29 Future of Payments and Loyalty Programs08:12 Equity Ownership and Consumer Privacy Concerns09:21 Debating the Viability of Tokenized Equity10:54 Potential Issues and Real-World Examples13:54 The Need for Thoughtful Implementation24:01 Conclusion and Final Thoughts26:30 Costco Gold Purchase Dilemma27:50 Crypto Arbitrage and Kimchi Premium28:46 Tokenization and Equity Concerns30:07 Universal Basic Income and COVID30:29 Naked Shorting and GameStop33:10 Digital Securities and NFTs45:27 Strategic Reserves and National Security47:58 Fiat Money and Economic Constructs48:14 Concluding Thoughts and Future Discussions Get full access to Bitcoin, Blockchain and Tokenization at oldmennewmoney.substack.com/subscribe

Jun 19, 2025 • 48min
The Rise of Investment Crowdfunding: A Revolution in Venture Capital
The Rise of Investment Crowdfunding with Yvan De MunckIn this episode of 'Old Men, New Money,' hosts Phil Larmon and Douglas Borthwick interview Yvan De Munck, an expert in investment crowdfunding. Yvan shares his extensive experience in the crowdfunding space, tracing the evolution from early platforms like Lending Club to the current possibilities in investment crowdfunding. He discusses the benefits of using data analytics to predict successful crowdfunding investments and how platforms like CClear.ai can empower individual investors to act like VCs. Yvan also touches on how the industry is set to explode, driven by increased participation, the rise of tokenization, and the potential for investment crowdfunding to rival traditional VC models.00:00 Introduction and Social Media Promotion01:03 Interview with Yvan De Munck: Investment Crowdfunding Expert01:43 Yvan's Journey into Crowdfunding02:16 The Birth of Lending Club and Marketplace Lending04:16 Institutionalization of Crowdfunding07:07 The Rise of Online Lending09:23 Investment Crowdfunding vs. Venture Capital10:54 The Role of Data in Crowdfunding Success12:47 CClear.ai and the Future of Crowdfunding14:19 Competitive Benchmarking and Market Insights16:04 The Importance of Data in Crowdfunding18:47 Capital Pulse Ratings and Offering Insights25:50 Understanding Platform Incentives27:15 The Role of Community in Crowdfunding Success28:04 Examples of Successful Crowdfunding Exits29:23 Analyzing Crowdfunding Success Rates32:15 Marketing Strategies for Crowdfunding33:46 The Importance of Digital Marketing34:35 Investor Ratings and Metrics40:55 VC Involvement in Crowdfunding44:12 The Future of Tokenization and Liquidity47:23 Final Thoughts and Conclusion Get full access to Bitcoin, Blockchain and Tokenization at oldmennewmoney.substack.com/subscribe

Jun 10, 2025 • 42min
Revolutionizing the Trucking Industry
Revolutionizing Trucking Finance with Blockchain: A Conversation with Todd ZieglerIn this episode of Old Man, New Money, Ali Davoudi and Douglas Borthwick speak with Todd Ziegler, CEO of TCS Blockchain. Todd explains how TCS is transforming the trucking industry by addressing the high cost of capital, a major problem in the $2 trillion US supply chain. Utilizing blockchain technology, TCS offers faster and cheaper settlements for transportation companies by disintermediating traditional factoring companies. Todd shares his journey from the trucking industry to blockchain, detailing the benefits of their ERC 20 token on the INX platform, and how it significantly reduces costs for truckers. The episode delves into the complexities of factoring, the inefficiencies in current systems, and TCS's innovative solutions, including potential scaling into other industries.Learn More Here: https://www.tcsblockchain.com/00:00 Introduction to the Guest and TCS Blockchain00:59 Todd Ziegler's Background and Entry into Blockchain02:43 Challenges in the Trucking Industry04:27 Factoring in the Trucking Industry10:53 TCS Blockchain's Solution for Truckers19:10 How TCS Token Works21:44 Understanding Secondary Market Participation22:11 Regulatory Environment and Future Incentives24:15 Factoring Beyond Trucking24:38 Scaling and Industry Expansion25:48 Challenges and Opportunities in Factoring26:59 Acquisition Interest and Market Position28:15 Blockchain and Digital Assets in B2B Settlement29:28 Current Operations and Future Plans31:05 Funding and Capital Management39:21 Crowdfunding and Token Economics41:37 Conclusion and Contact Information Get full access to Bitcoin, Blockchain and Tokenization at oldmennewmoney.substack.com/subscribe


