Venture Capital Through the Web3 Lookingalass Trad 
VC vs. Web3 VC

With Special Guest
Brooke Pollack
Stephen Mckeon


In this Episode, we peel back the layers of venture capital investment, contrasting the traditional VC approach with the emerging trends in the Web3 space. Our guests share their narratives on entering the world of web3 investing, revealing the allure of the sector and their varied experiences with its volatile market cycles.

In this Episode we cover:

  • Understanding the essence of traditional venture capital, including its setup, stakeholders, and the lifecycle of deals.
  • Insights into the transition into Web3 investing, exploring what drew investors to the space, their experiences with its volatility, and how the culture of Web3 informs their investment decisions.
  • Discussion on how newer VC models, like syndicates and investment DAOs, are learning from and adapting to the Web3 revolution.
  • The distinctions between Web3 VC and other sectors are examined, alongside the unique opportunities and hurdles that come with investing in the Web3 domain and how it has changed investment practices.
  • The potential of Web3 culture and technology to expand who can invest in VC and the nature of competition with new market entrants.
  • An analysis of the past crypto bull markets, highlighting the shift in investment sources and strategies, and pondering the future of crypto market cycles and VC funding.

Show Notes


  • 0:02 - Traditional VC vs. Web3 venture investing with industry experts. 
  • 1:57 - Crypto investing and the future of Web3 with Brooke and Steven. 
  • 5:44 - Venture capital investing and deal sourcing. 
  • 12:01 - Fund of funds investing in crypto and blockchain startups. 
  • 15:23 - Investing in crypto space, conviction, and market cycles. 
  • 18:52 - Investing in Web3, differences from traditional venture capital. 
  • 25:56 - Web3 VC investing differences.
  • 29:39 - Web3 investing, market cycles, and their impact on early-stage startups. 
  • 35:44 - Crypto funding sources in 2017 and 2021. 
  • 39:13 - Crypto cycles, institutional interest, and future growth. 
  • 42:17 - The future of blockchain technology and its potential impact on the way we raise funds and participate in projects.
  • 47:40 - Using blockchain for securities and equity assets.
  • 49:41 - Impact of blockchain on IPOs and investor protections.