On The Brink with Castle Island

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

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.

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

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

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

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

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

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

Matt and Nic review the top stories of the week in the cryptoasset industry. This week's topics include: Binance's acquisition of CoinMarketCap Factom's insolvency Telegram's latest setback in court Recent stablecoin growth Nic's piece on bailouts in Coindesk and much more news of the week

Adam Draper, co-founder of BoostVC, an accelerator and venture fund focused on Sci-Fi technologies joins the show. In this episode we discuss: - Adam's advice for portfolio companies navigating the current COVID 19 crisis - His thesis on Virtual Reality and what categories he is most excited about - His journey in crypto, from being an early investor in Coinbase to present - Book recommendations Learn more about Boost at Boost.vc and follow Adam on Twitter @adamdraper