E49: Long Journey's Strategy for Chasing "Magically Weird" Companies

"Turpentine VC" | Venture Capital and Investing

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 [e-mail].

--

RECOMMENDED PODCASTS:

🎙️1 to 100 | Hypergrowth Companies Worth Joining

Every week we sit down with the founder of a hyper-growth company you should consider joining. Our goal is to give you the inside story behind breakout, early stage companies potentially worth betting your career on. This season, discover how the founders of Modal Labs, Clay, Mercor, and more built their products, cultures, and companies.

Spotify:https://open.spotify.com/show/70NOWtWDY995C8qDqojxGw

Apple: https://podcasts.apple.com/podcast/id1762756034

-

ECON 102 W/ NOAH SMITH

Keeping econ entertaining - Noahpinion author Noah Smith and Erik Torenberg break down business news and politics every week.

Apple: https://podcasts.apple.com/podcast/id1696419056

Spotify: https://open.spotify.com/show/6q7Gn5lP8TTtBPuV1NJSGs

--

SPONSORS:

☁️Oracle Cloud Infrastructure (OCI) is a single platform for your infrastructure, database, application development, and AI needs. OCI has four to eight times the bandwidth of other clouds and offers one consistent price. Oracle is offering to cut your cloud bill in half. See if your company qualifies at oracle.com/turpentine

🛠️ Building an enterprise-ready SaaS app? WorkOS has got you covered with easy-to-integrate APIs for SAML, SCIM, and more. Join top startups like Vercel, Perplexity, Jasper & Webflow in powering your app with WorkOS. Enjoy a free tier for up to 1M users! Start now at https://bit.ly/WorkOS-Turpentine

💥 Head to Squad to access global engineering without the headache and at a fraction of the cost: head to https://choosesquad.com/ and mention “Turpentine” to skip the waitlist.

--

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