Lee Jacobs

Background

Lee Jacobs is a San Francisco-based entrepreneur turned venture capitalist and co-founder and managing partner of Long Journey Ventures ^{1 2}. He attended the University of Pennsylvania, where he studied sociology and co-founded CampusDock, an online classified marketplace for college students, graduating in 2008 ^{3 4}.

After college, Jacobs worked as a product manager at Comcast Interactive Media ⁴. In 2011, he founded Colingo, a peer-to-peer language learning company focused on helping young professionals in Brazil learn English; the company raised $2.4 million from Silicon Valley investors ^{4 5}.

Following Colingo, Jacobs worked as an investor at MHS Capital, a San Francisco-based seed fund with investments in companies including Thumbtack, Opower, Outreach, and Udemy, from approximately 2014 to 2015 ^{4 6}. In 2013, Jacobs completed the first-ever outside syndicate on AngelList for Descomplica, a Brazilian education company ^{3 7}. He subsequently joined AngelList as a partner around 2015, helping top angel investors deploy capital more effectively through the platform’s syndicate tools ^{3 7}.

Around 2015, Jacobs co-founded Edelweiss, a micro-fund focused on early-stage investments, alongside Brian Balfour, Elaine Wherry, and Jonathan Bruck ³. Through Edelweiss, the group backed companies including Blue Bottle, Whistle, Kettle & Fire, and Gametime ³. In 2020, the fund was renamed Long Journey Ventures and expanded with new partners including Cyan Banister (formerly of Founders Fund) and Pascal Levy-Garboua ^{3 8}. In March 2025, the firm closed its fourth fund, Long Journey IV, at $181,818,181.80, bringing total capital raised to approximately $450 million across roughly 130 investments ^{9 10}.

Stated Thesis

Jacobs publicly describes his investment approach as seeking “magically weird” founders — those with independently derived insights and the courage to pursue ideas that others initially dismiss. He has stated: “The magically weird are founders with independently derived insights…the ones who arrive at unique conclusions through their own path” ¹¹.

Jacobs positions himself as a “second believer” investor, explaining: “Starting a company is lonely. There’s this burning belief in something only you can see. What’s needed isn’t skepticism — it’s someone with the curiosity to stand beside you and see what you see” ¹².

He has described the firm’s approach as a “Federation of Angels/Operators,” combining experienced entrepreneurs with investing activity, which he says allows them to “attract world class talent as true partners and keep our fund relatively small” ³. He has also stated: “We understand founders and their journey. We’ve walked that path and we feel we can be good sherpas for the travels they have ahead of them” ³.

The Mercury investor database describes Jacobs as a “generalist, and invests in most industries outside of Biotech and Hardware” ¹³. He has expressed a deep interest in hard tech and physical infrastructure, and frequently highlights companies building complex industrial systems such as teams working on lasers, ground stations for space, or restoring the domestic chip industry ¹⁴.

On the qualities he looks for in founders, Jacobs has said he appreciates people who are “ridiculously talented,” have strong track records, and are “scrappy hustlers who do what it takes to get things done and are self-driven” ¹⁵.

Inferred Thesis

Based on 25 verified investments attributed to Jacobs or Long Journey Ventures below (a subset of the firm’s claimed 130 total investments across all partners), the following patterns emerge. Note: this sample represents roughly 19% of the firm’s total claimed portfolio, and many investments are shared with co-founder Cyan Banister, so percentages are directional rather than definitive for Jacobs individually.

Stage distribution: Predominantly seed and pre-seed. Jacobs’ stated check size of $100K-$1M and his role as an early-stage “second believer” align with observed behavior. The Signal NFX profile lists his investment range as $100K minimum, $500K target, $1M maximum ¹⁶. Mercury lists his check size as $500K-$1M at pre-seed and seed ¹³.

Sector breakdown: Based on 25 verified investments: 5 in AI/deeptech (20%) including Together AI, DeepMind, Anduril, Arcee, and Deno; 4 in energy/climate/hardware (16%) including Crusoe Energy, Bedrock Energy, Stoke Space, and Diamond Foundry; 4 in fintech/commerce (16%) including Affirm, Checkr, Carta, and AtoB; 3 in consumer/marketplace (12%) including Uber, Postmates, and Thumbtack; 3 in health/wellness (12%) including Mindbloom, Superpower, and TrueMed; 2 in education (8%) including Wonderschool and Nectir; 4 across other sectors (16%) including Notion, Loom, Flock Safety, and Flexport.

Notable pattern — hard tech and capital-intensive bets: Despite the Mercury database describing Jacobs as a generalist who avoids hardware, his portfolio shows significant investment in capital-intensive companies (Crusoe Energy, Stoke Space, Bedrock Energy, Diamond Foundry, SpaceX via the firm). This suggests a willingness to back hard-tech founders when the “magically weird” thesis applies, particularly at the intersection of energy and computing infrastructure.

Geographic focus: Primarily U.S.-based companies, with some international exposure (Rappi in Latin America). His early career working with Brazilian startups via Colingo and Descomplica suggests comfort with international founders ^{4 5}.

Founder profile: Jacobs appears to favor founders with deep domain expertise and contrarian conviction. The Crusoe Energy investment (Bitcoin mining from gas flares, later pivoting to AI infrastructure) and Together AI (open-source AI infrastructure) both exemplify founders pursuing ideas initially seen as unconventional ^{11 17}.

Co-investor patterns: Based on verified portfolio data, frequent co-investors include Cyan Banister (co-founder, shared across most Long Journey deals), Scott Banister (venture partner at LJV, PayPal founding board member), and the broader Long Journey Ventures team including Arielle Zuckerberg and Pascal Levy-Garboua ².

Portfolio

Note: Many “Early” dates reflect that sources confirm the investment but not the specific year. This table represents approximately 19% of the firm’s claimed 130 investments. Companies marked with early dates such as Uber and SpaceX were primarily invested through Cyan Banister and Scott Banister prior to the formal founding of Long Journey Ventures; they are listed here as firm-level portfolio companies.

In Their Own Words

“The magically weird are founders with independently derived insights…the ones who arrive at unique conclusions through their own path, not by following the crowd.” — Lee Jacobs, Long Journey Ventures Fund IV announcement, March 2025 ¹¹

“Starting a company is lonely. There’s this burning belief in something only you can see. What’s needed isn’t skepticism — it’s someone with the curiosity to stand beside you and see what you see.” — Lee Jacobs, X/Twitter, 2025 ¹²

“We understand founders and their journey. We’ve walked that path and we feel we can be good sherpas for the travels they have ahead of them.” — Lee Jacobs, Long Journey Ventures blog ³

“In Jewish numerology, 18 represents ‘chai’ or ‘life.’ Growing up, I was often given gifts in increments of 18; it was a blessing for life.” — Lee Jacobs, on the significance of the $181,818,181.80 Fund IV size, Jewish Telegraphic Agency, March 2025 ⁹

“The horrific attacks in Israel on October 7th awakened something dormant at my core — a deep inner knowing of my purpose and what I’m willing to fight for.” — Lee Jacobs, blog post referenced by Jewish Insider, April 2025 ²⁰

“Sharing our values is a very important piece of the puzzle.” — Lee Jacobs, on selecting limited partners aligned with the firm’s values, Jewish Insider, April 2025 ²⁰

What Founders Say

Together AI co-founder and CEO Vipul Ved Prakash credited Long Journey’s “willingness to go along with the thought experiment” during early discussions about the company ¹⁰.

Crusoe Energy co-founder Chase Lochmiller has described how Jacobs became the company’s first advisor after a meeting at Dandelion Chocolate in San Francisco in 2018, where Lochmiller explained his vision for Bitcoin mining using natural gas flares. Lochmiller recalled how Jacobs stayed calm and encouraging during the company’s development and helped him put together the seed round ^{17 21}. Crusoe is now valued at approximately $3 billion ¹⁰.

No additional independently sourced founder testimonials found beyond the above. The firm’s “Be a Bubbe” philosophy — treating founders with the unconditional tough love of a Yiddish grandmother — is self-reported by the firm rather than confirmed by external founders ¹¹.

Connections

• Co-Founder, Long Journey Ventures — alongside Cyan Banister (Co-Founder & GP) and Arielle Zuckerberg (GP) ²
• Former Partner, AngelList (~2015) — worked with Naval Ravikant on syndicate infrastructure ^{3 7}
• Co-Founder, Edelweiss (~2015) — alongside Brian Balfour (CEO of Reforge), Elaine Wherry (co-founder of Meebo), and Jonathan Bruck (founder of Pocket) ³
• First Advisor, Crusoe Energy (2018-present) — helped Chase Lochmiller with seed fundraising ¹⁷
• Venture Partner relationship with Scott Banister — PayPal founding board member and co-inventor of keyword auction advertising; venture partner at Long Journey ²

Sources