Dec 20, 2024 · 56m · sourcery
Cyan Banister & Lee Jacobs: Investing in 'The Magically Weird' | SpaceX, Uber, Anduril · Sourcery with Molly O'Shea
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In this episode of 'Sourcery,' host Molly O'Shea interviews venture capitalists Cyan Banister and Lee Jacobs of Long Journey Ventures about their unique 'magically weird' investment strategy, unconventional community-building methods, and the alignment of venture capital with higher purpose.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Molly holds 11.9% of the talking time here. How this is scored →
Molly as informed peer 3.6 Guest teaching 2.6 Guest disagreement 0.7 Molly pushing back 0.2
speaking balance: gold is Molly, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 40:00 Pushing back against superficial social impact investing
Lee and Cyan forcefully reject empty performative 'social impact' branding in VC, arguing standard capitalism creates real impact if grounded in solid economics rather than feel-good distortions.
Hardest push from Molly ▶ 44:10 Host probing founder cynicism across sectorsMolly presses back on where the cynicism lies in tech, directly summarizing founder complaints regarding VC capital hoarding and hyper-narrow AI/defense biases.
Biggest teaching moment ▶ 6:45 Thiel's reframing of shallow networking questionsCyan educates the audience and host on Peter Thiel's critique of asking 'what are you excited about,' explaining that it represents lazy outsourcing of curiosity.
Molly holds their own ▶ 37:40 Host contextualizes post-exit wealth psychologyMolly demonstrates industry literacy by synthesizing Morgan Housel's insights on founder psychology and the emotional bifurcation between building for pure wealth versus enduring meaning.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Molly as informed peer | Guest teaching | Guest disagreement | Molly pushing back | Why |
|---|---|---|---|---|---|---|
| Defining 'The Magically Weird' Investment Ethos | 3 | 3 | 1 | 0 | Molly opens by asking Lee and Cyan to define their 'magically weird' investment ethos. Lee and Cyan explain their thesis of backing counterintuitive, non-consensus founders and companies that initial VCs dismiss. | |
| Sourcing Unconventional Founders and Brand Compounding | 3 | 2 | 1 | 0 | Molly asks how Long Journey discovers these unusual deals. Lee and Cyan explain their deliberate branding, network compounding among independent thinkers, and aversion to standard, boring tech panel dinners. | |
| Designing Immersive Events and The Matrix Red Pill Story | 3 | 4 | 1 | 0 | Cyan shares an extended, vivid breakdown of how Long Journey creates experiential, immersive events to break down social facades, detailing the Matrix red-pill stunt that led to a one-night Michelin pop-up dinner. | |
| Interlude: Making Friends and Cyan's Candle Phobia | 3 | 1 | 0 | 0 | A lighthearted interlude where Molly mentions dinner conversation starters like phobias, prompting Cyan to reveal her genuine childhood phobia of candles. | |
| Lee's Unusual Story: The Austin Crow Incident | 2 | 1 | 0 | 0 | Lee tells a humorous personal anecdote about a crow landing directly on his head in Austin while walking with partner Arielle, keeping the dialogue informal and conversational. | |
| Targeting Misfit Founders & The Crusoe Energy Case Study | 4 | 3 | 1 | 0 | The conversation returns to fund strategy as Cyan and Lee unpack their focus on misfit founders, using Chase Lochmiller and Crusoe Energy's flare-gas mining origin as a prime case study. | |
| Long Journey's Fund Evolution and Founding Origins | 4 | 3 | 0 | 0 | Lee and Cyan outline the structural growth of Long Journey from angel investing and SPVs at AngelList and Founders Fund to building dedicated early and growth vehicles. | |
| Spirituality, Purpose, and Higher Callings in Silicon Valley | 4 | 3 | 1 | 0 | Molly observes the broader cultural shift toward spirituality and higher purpose among tech circles. Cyan explores post-pandemic existential reflections, dismantling ego, and aligning profit with purpose. | |
| Capitalism as Social Impact and Building for Meaning | 5 | 3 | 1 | 1 | Molly connects the purpose conversation to Morgan Housel's discussions on post-exit emptiness. Lee and Cyan push back against superficial 'social impact' labeling, asserting capitalism itself is impactful when directed toward enduring value. | |
| Venture Capital Cynicism, Liquidity Bottlenecks, and Hype Cycles | 5 | 3 | 1 | 1 | Molly prompts a breakdown of venture capital cynicism. Cyan and Lee analyze liquidity droughts, zombie funds, mark-up hangovers, and the overhyped challenges of government sales in defense tech. |
Statements from this episode (13)
Jacobs: Great companies look weird at the pre-seed and seed stage
“We've really honed in on what we think great companies look like at the time in which we invest, which is the pre-seed and seed. We think they look quite weird at the time.”
Jacobs: Sourcing Unconventional Founders Compounds Through Their Personal Networks
“When you invest in these people that are really independent thinkers and they end up in interesting companies and start great things, they tend to have friends like that. And so it really compounds on itself.”
Jacobs: Long Journey avoids hosting standard venture capitalist AI networking events
“We're never going to do an event that's like a boring AI event where it's like seven VCs and two founders and your job is to like talk about the future of AI”
Banister: VCs asking 'what are you excited about' exposes their own cluelessness
“When someone says, what are you excited about? It's because they don't know what to be excited about themselves. And so they're fishing you to try to get excited about something because they lack it in their lives. And so they're doing, they're outsourcing the…”
Banister: VC money is fungible; differentiation comes from ethics and values
“Well, if you think about it, all VCs are kind of, we have money, it's the same, right? It's not, the money's not different. So what makes us stand apart is our ethics, and who we are, and what we stand for, and our compass.”
Jacobs: Standard SaaS business models offer no investing alpha
“Not just like, hey, I've got a business plan, and I'm gonna go and sell SaaS, you know, things. It's gonna be nine 99, and people are gonna love it. Like, everyone says that. There's no alpha in that.”
Banister: Bible Sales Are Up 28% With Most Buyers First-Time Readers
“I think I saw a statistic the other day that Bible sales are on the rise by like 28%. And most of those are first time readers.”
Jacobs: Sequoia Capital names office conference rooms after its non-profit LPs
“If you go into their offices you walk in, all the conference names are their LPs. It's Ford Foundation or whomever else is the sort of the causes that back them. And whenever they have an IPO, the you know, the CEO of the company is on the front of the page, b…”
Banister: Most of her philanthropic donations fund constitutional amendment causes
“For me, I'm very, very passionate about the first amendment and most of the causes I donate to are first amendment related or second amendment or fourth amendment, anything constitutional.”
Banister: Founders must define higher purpose before building wealth
“I would advise every founder Before you start your company, think about the higher purpose that you want to serve so that when you are finally successful and you reach that end point, you know exactly what that money's for. And that way you're like, yep, that …”
Jacobs: Feel-good companies that are bad businesses create zero impact
“If it's, i.e. It's not a good business, but it feels good to do it that actually doesn't have an impact at all.”
Banister: M&A and IPO Markets Might Open Up Soon
“I think that's about to change, potentially, where M&A might open up in public markets. You know, you might see more companies go public than has been in the past, last four years.”
Banister: Defense tech venture investing is currently 'ahead of its skis'
“And then defense, I think is a little bit ahead of its skis. You know, we were just having a conversation earlier, Leah and I, about this, is, you know, selling into the government is really hard, and I think people don't understand that.”