Old Men, New Money®: Bitcoin, Blockchain, Tokenization & Agentics

The Critical Role of Infrastructure in Digital Securities

In 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 Infrastructure

00:10 The Importance of Infrastructure in Digital Securities

00:44 Building the Necessary Infrastructure

01:09 Critical Components of Digital Securities Infrastructure

03:20 Custody Models and Providers

07:08 Role of Transfer Agents

10:41 Trading Venues and Market Liquidity

15:39 Global Developments and Regulatory Landscape

20:00 Future of Digital Securities Infrastructure

21:15 Practical Advice for Issuers and Investors

24:10 Conclusion and Future Modules

The Complete Guide to Security Token Offerings (STOs): Costs, Process, and Pitfalls

In 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 Offerings

00:14 Understanding the STO Process

02:02 Key Players in an STO

04:44 Detailed Breakdown of the STO Timeline

13:48 Common Mistakes and How to Avoid Them

15:31 Successful STO Case Study: INX

17:17 Practical Advice for STOs

19:05 Conclusion and Next Steps

Navigating the Regulatory Maze for Digital Securities: Reg D, Reg S, and Reg CF Explained

In 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 Roadmap

00:27 Importance of Understanding Regulations

01:10 Overview of Regulatory Exemptions

03:26 Deep Dive into Reg D

05:52 Exploring Reg S

07:09 Understanding Reg CF

08:00 Full Registration Process

09:09 Compliance and Common Mistakes

12:00 Future of Digital Securities Regulations

12:47 Practical Advice for Investors and Founders

13:35 Conclusion and Next Episode Preview

Understanding Digital Securities: Distinguishing from Crypto

In 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 Securities

00:42 Understanding Digital Securities vs. Cryptocurrencies

02:52 Types of Blockchain Tokens

04:20 The Howey Test and Security Tokens

06:04 The Advantages of Digital Securities

07:15 Real-World Examples and Success Stories

09:16 The Future of Digital Securities

09:55 Risks and Challenges in Digital Securities

11:14 Traditional Finance vs. Blockchain

13:04 Actionable Steps and Conclusion

Episode Summary:

Douglas Borthwick reveals why Galaxy Digital's decision to tokenize their NASDAQ-listed shares on Solana—not Ethereum—signals a seismic shift in blockchain adoption. This historic SEC-registered public equity tokenization exposes the trillion-dollar infrastructure mistake Wall Street is making by betting on brand recognition over performance.

Key Insights:

Solana processes 40x more transactions than Ethereum with 10,000x lower fees ($0.00025 vs $20-50)

93.5 million daily transactions in Q3 2025 vs Ethereum's 1.6 million

Solana captured 81% of all blockchain DEX transactions and 43% of global DEX volume

First time since 2016 a blockchain attracted more developers than Ethereum (7,625 vs 6,456)

Transaction finality dropping to 150 milliseconds with Alpenglow upgrade

$271 million in Q2 2025 network revenue—leading all blockchains for 3 consecutive quarters

Douglas Borthwick, who was part of the INX team behind the first SEC-registered security token offering, explains why traditional finance institutions like BlackRock, JPMorgan, and Franklin Templeton are backing the wrong blockchain for public markets.

Episode Timestamps:

00:00 - Introduction: Galaxy Digital's Groundbreaking Solana Tokenization

01:01 - Why Wall Street Defaults to Ethereum (And Why That's Wrong)

02:20 - Shocking Performance Data: Solana's 85x Transaction Advantage

05:12 - The Performance Gap That Matters: Speed, Cost & Finality

08:29 - Stablecoin Efficiency: Why Each Solana Dollar Works 8x Harder

11:01 - Debunking the "Security vs Speed" Myth

12:44 - The Coming Migration: What Happens in Next 24 Months

16:46 - Final Takeaway: Why TradFi Needs to Wake Up Now

Topics Covered: Blockchain comparison, Ethereum vs Solana, cryptocurrency adoption, DeFi, decentralized exchanges (DEX), stablecoins, tokenized securities, SEC regulations, institutional blockchain, Web3, public equity tokenization, transaction throughput, gas fees, developer migration, Alpenglow upgrade

Host: Douglas Borthwick | Follow on X: @DCBorthwickLearn more at OldMenNewMoney.com

Crypto Treasuries: Bitcoin, Ethereum, and Solana Strategic Plays

In this episode of 'Old Men New Money,' Douglas Borthwick explores the emerging trend of corporations leveraging cryptocurrencies within their treasury models. Starting with MicroStrategy's pioneering move to convert its treasury into Bitcoin in 2020, the landscape now includes a variety of approaches: MicroStrategy (rebranded to Strategy) focusing on Bitcoin, Bit Mine on Ethereum, and Solve Strategies on Solana. Borthwick breaks down the operations, risks, yields, and strategic advantages of each model, highlighting their unique approaches to financing and revenue generation. Suitable for those looking to understand different corporate cryptocurrency treasury strategies and their potential impact on portfolios.

00:00 Introduction to Crypto Treasury Companies

01:36 MicroStrategy's Bitcoin Strategy

04:35 Bit Mine's Ethereum Accumulation

07:19 Solana Infrastructure with Saul's Strategies

11:05 Comparing the Three Models

14:35 Investment Risks and Considerations

15:50 Choosing the Right Crypto Treasury Company

16:46 Conclusion and Next Steps

Solana: The Next Generation of Blockchain Technology

The podcast discusses the unprecedented evaporation of $19 billion in crypto positions on October 11, 2025, emphasizing Solana's resilience in handling high transaction volumes. Using an analogy of the 1800s railroad boom, the speaker compares Solana to pioneering railroads that succeeded due to their high traffic, low costs, and reliability. The script explains how Solana's blockchain works, the role of SOL as fuel, and how validators maintain the network while earning rewards. It also guides regular people on how to buy and stake SOL for passive income, highlights Solana's capacity for supporting decentralized apps, and addresses the risks of crypto volatility. Ultimately, the podcast underscores the significance of Solana's technology in the evolving blockchain landscape.

00:00 Introduction: The $19 Billion Crypto Crash

01:03 The Railroad Analogy: Understanding Solana

02:13 How Blockchains Actually Work

03:03 The Validators: Keeping Solana Running

04:11 How Regular People Get Involved

04:48 Staking Your SOL: Earning Passive Income

05:47 What Actually Runs on Solana

06:48 The Actual Numbers: Solana's Performance

08:28 The Risks You Need to Know

09:34 The Bigger Picture: Blockchain's Future

10:39 Outro: Getting Started with Solana

Digital Securities and Consumer Equity: The Revolution and Risks

In 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 Kickoff

00:56 The Impact of the Genius Act and Clarity Act

01:58 Understanding Digital Securities and Consumer Models

02:26 Practical Applications and Benefits of Digital Securities

05:01 Challenges and Considerations in Digital Securities

05:29 Future of Payments and Loyalty Programs

08:12 Equity Ownership and Consumer Privacy Concerns

09:21 Debating the Viability of Tokenized Equity

10:54 Potential Issues and Real-World Examples

13:54 The Need for Thoughtful Implementation

24:01 Conclusion and Final Thoughts

26:30 Costco Gold Purchase Dilemma

27:50 Crypto Arbitrage and Kimchi Premium

28:46 Tokenization and Equity Concerns

30:07 Universal Basic Income and COVID

30:29 Naked Shorting and GameStop

33:10 Digital Securities and NFTs

45:27 Strategic Reserves and National Security

47:58 Fiat Money and Economic Constructs

48:14 Concluding Thoughts and Future Discussions

The Rise of Investment Crowdfunding with Yvan De Munck

In 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 Promotion

01:03 Interview with Yvan De Munck: Investment Crowdfunding Expert

01:43 Yvan's Journey into Crowdfunding

02:16 The Birth of Lending Club and Marketplace Lending

04:16 Institutionalization of Crowdfunding

07:07 The Rise of Online Lending

09:23 Investment Crowdfunding vs. Venture Capital

10:54 The Role of Data in Crowdfunding Success

12:47 CClear.ai and the Future of Crowdfunding

14:19 Competitive Benchmarking and Market Insights

16:04 The Importance of Data in Crowdfunding

18:47 Capital Pulse Ratings and Offering Insights

25:50 Understanding Platform Incentives

27:15 The Role of Community in Crowdfunding Success

28:04 Examples of Successful Crowdfunding Exits

29:23 Analyzing Crowdfunding Success Rates

32:15 Marketing Strategies for Crowdfunding

33:46 The Importance of Digital Marketing

34:35 Investor Ratings and Metrics

40:55 VC Involvement in Crowdfunding

44:12 The Future of Tokenization and Liquidity

47:23 Final Thoughts and Conclusion

Revolutionizing Trucking Finance with Blockchain: A Conversation with Todd Ziegler

In 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 Blockchain

00:59 Todd Ziegler's Background and Entry into Blockchain

02:43 Challenges in the Trucking Industry

04:27 Factoring in the Trucking Industry

10:53 TCS Blockchain's Solution for Truckers

19:10 How TCS Token Works

21:44 Understanding Secondary Market Participation

22:11 Regulatory Environment and Future Incentives

24:15 Factoring Beyond Trucking

24:38 Scaling and Industry Expansion

25:48 Challenges and Opportunities in Factoring

26:59 Acquisition Interest and Market Position

28:15 Blockchain and Digital Assets in B2B Settlement

29:28 Current Operations and Future Plans

31:05 Funding and Capital Management

39:21 Crowdfunding and Token Economics

41:37 Conclusion and Contact Information