Ep. 66 - Jesse Randall

Jesse Randall is the CEO of Sweater Ventures, which he founded in 2018 after 20 years of experience in venture capital (VC) and startups. He dropped the idea of a traditional VC fund due to his ineligibility as an accredited investor and worked with the SEC to create a structure for everyday investors to access the asset class. Randall previously founded six companies and ran a software accelerator where he worked with more than 200 startups. He is dedicated to leveling the playing field in the venture ecosystem and empowering retail investors to participate in the future economy. In this episode of Inside Startup Investing, host Chris Lustrino talks to Jesse about how Sweater Ventures’ innovative approach to venture capital makes it more accessible to everyday investors. They discuss the benefits of an evergreen fund structure, the challenges in managing fund growth, and how the concept of large portfolio theory guides Sweater Ventures’ investment strategy. See video timestamps below. [06:25] The inspiration behind Sweater Ventures [11:05] Understanding the Cashmere Fund: An evergreen fund structure [17:40] The investment strategy and large portfolio theory [25:06] Exit events and distributions in the Cashmere Fund [26:25] Management fees and incentive structure for Sweater Ventures [28:08] Balancing fund size and returns for optimal performance [31:24] Re-envisioning venture capital and unicorn hunting