In this episode of Turpentine VC, Erik interviews Lee Jacobs, Founder & Managing Partner of Long Journey. Lee shares his journey from early investments and his experience with AngelList to co-founding Long Journey with Cyan Banister and Arielle Zuckerberg. He discusses the firm’s unique focus on investing in "magically weird" companies and emphasizes the importance of values, mission orientation, and building trust in LP relationships. Lee also opens up about the challenges and rewards of early-stage fundraising, Long Journey’s operational strategies, and their vision for building a lasting, meaningful VC firm.

This show is produced by Turpentine: a network of podcasts, newsletters, and more, covering technology, business, and culture — all from the perspective of industry insiders and experts. We’re launching new shows every week, and we’re looking for industry-leading sponsors — if you think that might be you and your company, email us at erik@turpentine.co.

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LINKS:

Long Journey - https://www.longjourney.vc/

Lee Jacobs on Twitter - https://twitter.com/leejacobs

TIMESTAMPS:

(00:00) Intro

(01:54) Founding Long Journey and Early Investments

(03:28) Breakthrough with AngelList Syndicates

(04:09) Joining MHS Capital and Learning from Mark Sugarman

(05:04) Building Edelweiss at AngelList

(06:47) Partnering with Cyan Banister

(09:26) Challenges and Successes in Early Investments

(10:12) Doing SPVs at AngelList

(11:28) SPONSORS: Oracle | WorkOS

(13:30) Scaling the Fund and Bringing on Partners

(15:41) Building the Team and Decision Making

(18:56) Adding Arielle Zuckerberg to the Team

(20:17) Lee’s Vision for Long Journey

(22:26) SPONSOR: Squad

(23:54) Building an LP Base

(25:19) Becoming Institutional

(25:48) Opportunity Fund vs. Growth Fund

(27:43) The Generalist Fund Approach

(29:12) Venture Partner Strategy

(32:32) Core Values and Mission Orientation

(38:14) Lee’s Unique Approach to Venture Capital

(44:15) Portfolio Construction and Key Investments

(47:18) Wrap

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