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On The Brink with Castle Island

Latest episodes

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Apr 27, 2020 • 51min

Peter Johnson (Jump Capital) on Fintech Investing (EP.72)

Peter Johnson, Head of Fintech and Crypto Investing at Jump Capital joins the show. In this episode we discuss: Peter’s fintech thesis and the categories that he is most excited about Jump Trading’s crypto journey and how Jump Capital works with the core trading business Cryptoasset market infrastructure and the categories that need to exist in order for this industry to thrive Learn more about Jump Capital at www.jumpcap.com and follow Peter @TheChicagoVC
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Apr 24, 2020 • 31min

Weekly News Roundup 4/24/20 (RenTech trading Bitcoin, It's Time to Build, dForce) (EP.71)

Matt and Nic review the top stories of the week in the cryptoasset industry. This week’s topics include: Deals of the week Our changing view of the halving Renaissance Technologies' announcement that they have the capacity to trade Bitcoin Our reaction to Mark Andreessen's "It's Time To Build" The dForce hack Ripple's lawsuit against Youtube Nic's defense of Coors Light
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Apr 22, 2020 • 40min

Michael Sonnenshein on building a Crypto-Asset Management Franchise (EP.70)

Michael Sonnenshein, Managing Director at Grayscale Investments joins the show. In this episode we discuss: Grayscale’s record quarter, raising $503.7 million in Q1 2020 The pace of institutional adoption of passively managed crypto asset products Thoughts on Libra, the halvening and other upcoming events in the cryptoasset industry Learn more about Grayscale at Grayscale.co and follow them on Twitter @GrayscaleInvest
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Apr 20, 2020 • 39min

Sal Ternullo (KPMG) on Enterprise Adoption of Cryptoassets

Sal Ternullo, Director and Cryptoasset Services Co-Lead at KPMG joins the show. In this episode we discuss: KPMG’s cryptoasset practice and the types of engagements they are leading for large enterprises Sal’s views on cryptoassets and security tokens including barriers to adoption for enterprises The outlook for M&A activity in this industry Learn more about KPMG’s cryptoasset practice here.
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Apr 17, 2020 • 39min

Weekly News Roundup 4/17/20 (Libra 2.0, MKR lawsuit, and Grayscale's big Q1) (EP.68)

Matt and Nic review the top stories of the week in the cryptoasset industry. This week’s topics include: Deal activity More bailout angst A discussion of Libra's second iteration The lawsuit against the Maker Foundation Grayscale's monster Q1 Blogs we enjoyed reading this week
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Apr 15, 2020 • 45min

Bob Davis (Highland Capital Partners) on Investing in Disruptive Technologies (EP.67)

Bob Davis, the founder of Lycos and General Partner at Highland Capital Partners joins the show. In this episode we discuss: Bob’s entrepreneurial journey, from taking Lycos from founding to IPO in 9 months, to an eventual $5.5 billion exit Perspectives on the venture industry and the impact of COVID-19 on the capital formation environment Comparisons of the blockchain industry to the early internet era General thoughts on Bitcoin’s macro narrative and the evolution of the market infrastructure to support this asset   Learn more about Highland Capital Partners at www.hcp.com
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Apr 13, 2020 • 56min

Brian Klein (Baker Marquart) on High-Stakes Crypto Litigation (EP.66)

Brian Klein, trial attorney at Baker Marquart, joins the show. Brian has represented clients in the crypto industry since 2014 and has been involved in some of the most impactful cases in that time. In this episode: How he got his start at the San Jose bitcoin conference in 2013 Representing Erik Voorhees in a case relating to SatoshiDice Whether the SEC has provided sufficient clarity on the application of the Howey test to token issuance Brian's view on the Hinman guidance on the security to commodity transmutation Brian's take on the SAFT Brian's take on disclosure in the industry The little-known variables that affect sentencing outcomes in criminal cases Brian's experiencing representing Marcus Hutchins Why Brian allocates so much time and effort to pro bono cases
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Apr 10, 2020 • 41min

Weekly News Roundup 4/10/20 (Bailouts, asteroid mining, and office plants) (EP.65)

Matt and Nic review the top stories of the week in the cryptoasset industry. This week’s topics include: Fidelity connecting to ErisX The sad fate of office plants Gold mining on asteroids More crypto dollarization The class action suits against Bitfinex, Block One, and others Retail vs institutional buying of Bitcoin The best articles published this week and much more 
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Apr 9, 2020 • 51min

Tom Jessop (Fidelity) and Tom Chippas (ErisX) on building institutional infrastructure (EP.64)

Tom Jessop, the President of Fidelity Digital Asset Services and Tom Chippas, the CEO of ErisX join the podcast. In this episode we discuss:  - Today's announcement that Fidelity Digital Assets is now connecting to ErisX as a venue for procuring cryptoassets - General perspectives on how COVID-19 impacts blockchain companies - Fidelity and ErisX's respective roadmaps and plans for 2020 Learn more about ErisX at www.ErisX.com  Learn more about Fidelity Digital Assets at www.fidelitydigitalassets.com  
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Apr 6, 2020 • 1h 14min

Alex Treece (Zabo) on Cryptoasset Value Accrual (EP.63)

Alex Treece, the president and cofounder of Zabo, joins the show.  How a background in private equity equipped him to think about crypto as a asset class Why Alex founded his startup, Zabo Why there are so few successful examples of utility tokens How tokens sit in the asset class taxonomy Why token value accretion is reliant on an informal contract with the issuer Distinctions between tokens that represent real world securities and natively accretive cash flow tokens which resemble securities Why he’s thinks that blockbuster token sales are a thing of the past Revisiting his old prediction that Bitcoin would outperform in a recession

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