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On The Brink with Castle Island

Apr 29, 2022

Matt and Nic are back with news and deals of the week, joined by Dave Gray, Head of Workplace Retirement Offerings and Platforms at Fidelity Investments, who joins us to talk about Fidelity's new Bitcoin 401(k) product. In this episode: 

  • Are airdrops taxable?
  • CheckTemplateVerify drama in Bitcoin
  • Central African...

Apr 27, 2022

Longtime Bitcoiner Bruce Fenton re-joins the show. In this episode we discuss:

  • Bruce’s career and the events that led him to discovering Bitcoin
  • Bitcoin’s social layer and how Bruce has managed to stay close to the project through so many chapters of the journey
  • His view on the tokenization of securities and why he...

Apr 25, 2022

Pat Larsen, founder and CEO of crypto tax prep company ZenLedger, joins the show for a timely discussion on how investors should be thinking about taxes this tax season. In this episode: 

  • The outlook for crypto taxes in 2022
  • Tax accounting for specific transactions
  • Clarifications and improvements to tax regulation

Apr 22, 2022

Matt and Nic return for another week of news and deals. In this episode: 

  • The OTB music debate rages on
  • Nic survives Covid
  • Should we bring back dueling?
  • Ancient altcoin dramas
  • Coinbase launches NFTs
  • Elon has financing to buy Twitter
  • Product suggestions for Twitter
  • The US sanctions Russian miners BitRiver
  • Is Russia...

Apr 20, 2022

Adam Jackson, co-founder and CEO of Braintrust, a web3 talent network joins the show. In this episode we discuss:

  • Marketplace business models and how web3 models will improve on web2 dynamics
  • How Adam came to the insight to launch Braintrust and how the platform works
  • The regulatory environment in the United States and...