Embracing Bitcoin: A Conversation with Jay Bluestine of Blue Square Wealth (E2)

Navigating the Digital Asset Landscape with Jay Bluestine from Blue Square WealthIn this episode of 'Old Men, New Money,' hosts Phil Larmon and Douglas Borthwick welcome Jay Bluestine from Blue Square Wealth. The discussion covers Jay’s transition from traditional finance at UBS, Smith Barney, and Morgan Stanley to founding Blue Square in 2018, his journey into Bitcoin investments, and the launch of risk-managed digital asset hedge funds. Jay explains the mechanics of hedge funds, the importance of regulated investment environments, and strategies for mitigating volatility in digital assets. The conversation also delves into the potential of blockchain technology, the future of institutional adoption, and the broader implications of Bitcoin and other digital assets on the financial landscape. This episode offers valuable insights for both seasoned investors and those new to digital assets, highlighting the convergence of traditional finance with decentralized finance.00:00 Introduction to Old Men, New Money00:17 Meet Jay Bluestine from Blue Square Wealth00:54 The Evolution of Blue Square and Digital Assets03:13 Understanding Hedge Funds and Investment Strategies05:51 Investment Options and Tax Considerations07:09 Exploring Bitcoin and Other Digital Assets13:28 Solana and the Future of Blockchain20:02 Institutional Adoption and Market Dynamics27:43 Understanding ETF Approvals and Institutional Adoption28:31 Regulatory Stamp of Approval and Its Implications29:22 Challenges for Wealth Managers and Institutional Involvement30:44 Volatility and Institutional Adoption34:17 Tokenization and the Future of Digital Assets41:39 Investment Strategies and Risk Management45:52 The Entrepreneurial Ecosystem and Future Opportunities47:51 Closing Remarks and Final Thoughts Get full access to Bitcoin, Blockchain & Tokenization at oldmennewmoney.substack.com/subscribe

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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