Cyan Banister & Lee Jacobs Investing in the Magically Weird | SpaceX, Uber, Anduril, Crusoe

Spirituality, Purpose, VC Cynicism, Meaningful Connections

Magically Weird, & Very Good at it

I couldn’t be more thrilled to share our latest conversation with Cyan Banister and Lee Jacobs, Founding Partners of Long Journey Ventures. We discuss their unique investment strategy focusing on their ethos of the 'Magically Weird,' how they build a community of independent thinkers, create memorable events, and foster authentic connections among founders. Notable investments include breakout companies like SpaceX, Uber, Anduril, Crusoe, Notion, DeepMind, Loom, Postmates, and more.

"We're looking for misfits, free thinking people." - Cyan

Sticking with the theme, this conversation is not the typical VC chat, we go deep into the rise of spirituality in Silicon Valley, the importance of aligning profit with purpose, and the shift in venture capital sentiment, highlighting the cynicism among founders and investors. The dialogue culminates in reflections on the future of startups and the significance of community and shared values in achieving meaningful success.

→ Listen on Spotify, YouTube, Apple

Timestamps below, along with resources, a breakdown of each topic (non-consensus & right, recipes for memorable events, rise in spirituality, aligning profit with purpose), and the fascinating story behind it all.

Timestamps

• 0:00 - A Dynamic Duo: Cyan & Lee

• 3:00 - Long Journey's Unique Strategy

• 6:00 - Crafting Memorable Events, Creating A Community

• 18:30 - What Is "Magically Weird" And Who Does It Attract?

• 24:00 - Origins Of The Fund

• 30:30 - Spirituality In Silicon Valley

• 37:30 - Aligning Profit & Purpose: Building For Wealth vs. Meaning

• 42:25 - State Of Startups: Cynicisms In VC

• 50:30 - 2024 Highlights & What Cyan & Lee are excited for in 2025

Angel Investing → Long Journey Ventures

Lee Jacobs and Cyan Banister first met many years ago while investing in the early days through AngelList with Naval Ravikant. Cyan was already an active angel investor, while Lee did the first angel Syndicate and a lot of SPVs - joining Naval full-time in 2015. After Cyan moved to Founders Fund, Lee continued to impress her with his eye for "magically weird" investments—unconventional opportunities with remarkable potential—safe to say, they collaborated a lot.

“some of our best deals at Founders Fund came from Lee”

When Cyan decided to leave Founders Fund, she approached Lee to co-found Long Journey Ventures.. his response was “duh.” Their partnership thrived on their complementary strengths and shared ethos of supporting independent thinkers and unconventional founders.

Together, they built Long Journey Ventures into a values-driven firm that not only invests in transformative companies but also fosters a unique community through immersive and creatively curated events. Their journey is rooted in a shared belief in aligning profit with purpose, supporting founders with bold visions, and creating lasting impact.

Long Journey Ventures have collectively been a part of 30+ unicorns from the earliest days. Writing some of the earliest checks to companies like SpaceX, Uber, Compound (COMP), Postmates, Affirm, Notion, Loom, Rappi, Crusoe Energy, Mindbloom, Flexport, Niantic, IRL, and many more.

Non-Consensus and Right

Long Journey Ventures has a distinctive investment strategy focused on backing "magically weird" founders and ideas, which they define as unconventional, non-consensus, and often misunderstood at the time of investment. These investments are characterized by their uniqueness and initial dismissal by others, such as Uber's early concept of strangers sharing rides, or Crusoe Energy's idea of mining Bitcoin using gas flares in North Dakota. The firm seeks out misfits and free thinkers—founders with big visions and life missions that drive them to create transformative businesses.