Long Journey Ventures Research
Investment Thesis
Long Journey Ventures is an early-stage venture capital firm that believes in backing "magically weird" founders building unconventional solutions. Founded by Lee Jacobs and Cyan Banister, the firm explicitly positions itself as a "second believer"—the early supporter who sees potential before it's obvious. Their tagline, "The second believers in the magically weird," captures their core philosophy: they seek founders working on ideas that others describe as ridiculous or stupid, combined with bold personalities who challenge the status quo.
The firm's investment approach is rooted in long-termism and founder support. They describe their relationship model as "being a bubbe"—a Yiddish term for grandmother—emphasizing hospitality, wisdom, protectiveness, directness, and unconditional support paired with uncompromising integrity. They view their character alignment as "Chaotic Good" (a Dungeons & Dragons reference), combining good hearts with free spirits, valuing freedom and individual autonomy above all else.
Stage and Check Size Focus
Long Journey Ventures is definitively an early-stage investor, focusing on pre-seed and seed-stage companies. Their portfolio companies span from concept stage through Series A/B. Based on visible portfolio activity, they write checks in the range of $500K-$2M+ for seed investments, with smaller checks for pre-seed.
Investment Activity
The firm has been actively deploying with significant momentum. Notable recent investments visible on their website include:
- Crusoe Energy (energy infrastructure, Series funding)
- Together AI (AI infrastructure)
- Loom (async video communication)
- Notion (productivity software)
- Uber, SpaceX, Postmates (via earlier checks)
- Flock Security (physical security)
- AnduriL (defense technology)
- TrueMed (health payments)
- Flexport (logistics)
Their portfolio demonstrates breadth across sectors including:
- AI & ML infrastructure (Together AI, Arcee AI, Numeric.io)
- Energy & climate (Crusoe, Bedrock Energy, Northwood Space)
- Health & biotech (TrueMed, Babylon Bio, Levels, Photon Health)
- Consumer apps (Loom, Notion, Wonderschool)
- Infrastructure & developer tools (Deno, Density, BitGo)
- Deep tech (AnduriL, Titan Dynamics, Northwood Space)
Team & Partners
General Partners:
- Lee Jacobs, Co-Founder & Managing Partner: Entrepreneur-turned-investor, early Founders Fund participant, strong background in identifying early-stage companies at concept stage. Invested in Crusoe, Together AI, Loom.
- Cyan Banister, Co-Founder & General Partner: Highly respected Silicon Valley early-stage investor, former Partner at Founders Fund. Early checks into Uber, PostMates, SpaceX, Flock Security. Passionate about founders creating jobs and enabling individual freedom.
- Arielle Zuckerberg, General Partner: Product-first mindset from background in product management. Previously at Coatue, helped design firm's first early-stage fund.
Venture Partners:
- Jonathan Bruck (serial founder, exits: Pocket/Mozilla, IndexTank/LinkedIn, Xoopit/Yahoo)
- Justin Mares (CEO/Co-founder of TrueMed, founder Kettle & Fire)
- Pascal Levy-Garboua (9th employee at Checkr, founded Noosa Labs)
- Scott Banister (PayPal founder, IronPort founder/Cisco $830M exit)
Notable Advisors:
- Elaine Wherry (Co-founder Meebo/Google acquisition, Dandelion Chocolate)
- Brian Balfour (Founder Reforge, VP Growth HubSpot)
- Aaron VanDevender (Founder Methid, ex-Chief Scientist Founders Fund)
- Andrew Look (ML engineer, Notion AI)
Operations Team:
- Dani Tustin (Head of Operations, tax attorney background in venture funds)
- Mike Wang (Head of Platform, higher education innovation background)
- Carolena Leon (Platform Associate, Microsoft PM background)
- Kelsey Muller (Executive Assistant, ex-Crusoe)
Investment Preferences & Decision Process
Long Journey explicitly seeks founders who are:
- "Magically weird"—unconventional, bold, willing to break norms
- "Second believers" themselves—operating on conviction before market consensus
- Building solutions to real problems with non-obvious answers
- Willing to sacrifice comfort for their vision
- Combining good hearts with free spirits (Chaotic Good)
Their decision process appears to be partnership-driven with Lee Jacobs as managing partner supported by strong GP team with deep sector expertise. The firm maintains a "bubbe" operational philosophy, prioritizing authentic relationships, community events (hosted as intimate dinner-like gatherings), direct communication, and hands-on support.
Geographic Focus
Primary focus on US-based founders (San Francisco, Silicon Valley bias evident), but portfolio includes some international companies. Co-founder Lee is based in San Francisco.
Recent Activity & Fund Status
The firm appears to be in active deployment mode with consistent investments across 2024-2025. Portfolio diversity and advisor network suggest strong deployment velocity. No indication of fund-raising or between-fund status.
Notable Philosophy
The firm's values reveal deep philosophical commitments:
- "Chase the magically weird": Unconventional ideas, quirky personalities
- "Be a bubbe": Hospitality, wisdom, protectiveness with integrity
- "Chaotic Good character alignment": Balance freedom with doing good
- "It's not Monopoly money": Serious stewardship of LP capital, not reckless
These principles suggest they're not mercenary venture capitalists but impact-oriented investors with personality and principles.