From Getting Venmo Off The Ground to Co-Founding Long Journey Ventures w/ Lee Jacobs

The Dealroom with Shamus Madan

In this episode, Shamus Madan converses with Lee Jacobs about his early investment journey, the influence of sociology on business, and his experiences with AngelList. They discuss venture capital competition, Jacobs' unique investment strategies, and provide advice for founders in crowded markets. They analyze an investment in Notion and forecast economic trends for 2022 and 2023.

Today, we have a very special guest Lee Jacobs the Founder and General Partner of Long Journey VC. Lee has been an investor for over a decade, investing in notable companies in the world like Loom, Wonderschool, and Pipefy, along with Cyan Banister and the team with experience in investing in SpaceX, Uber, Thumbtack, Notion, Affirm, and many more.

On the show, we will discuss how he worked to help get Venmo funded off the campus of UPenn, where he studied sociology, his journey into venture investing in the first Angel List syndicate with Naval, and little-known areas the firm is taking a look at what may be the next big thing.

Twitter of Host (Shamus Madan): @mbitpodcast

Twitter of Guest (Lee Jacobs): @LeeJacobs

(0:00) Introduction and Lee Jacobs' early investment journey (2:04) The role of sociology in business and venture capital (3:38) Traditional vs. networking routes in business (8:38) Lee Jacobs' experience with AngelList and its impact on his career (12:31) Competitive situations in venture capital and the values of Jacobs' firm (15:16) Investing strategy in out-of-the-ordinary companies (18:05) Advice for founders in crowded markets and how to stand out (20:24) Case study: Investing in Notion (21:09) Economic challenges and opportunities in 2022 and 2023 (23:14) Wrap-up of the episode