38: Molly Mielke McCarthy - The Art of Peopling
Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
Podcast Summary
In this captivating episode, Molly Mielke McCarthy, founder of Moth Fund, shares her unique approach to early-stage investing focused on finding "moths" - quirky, quiet, mission-driven founders who are often undervalued by traditional venture capital. (00:33) The conversation explores her "three-month rule" for evaluating exceptional people, the distinction between agency and ambition, and why she believes magnetism is a byproduct of authenticity. (03:48) Throughout their discussion, they delve into commerciality, self-knowledge, uncertainty tolerance, and the dance between legibility and illegibility in both investing and life.
- Core themes include people evaluation, authentic leadership, commercial instincts, self-awareness, and the balance between being understood and maintaining originality
Speakers
Molly Mielke McCarthy
Molly is an investor, writer, and founder of Moth Fund, an early-stage fund focused on backing "moths": quirky, quiet, mission-driven founders who are often underpriced by traditional venture capital. Her career has been a dance between "peopling" and making, holding design, product, and editorial roles at Figma, Notion, Stripe Press, and The Browser Company before exploring venture capital as a Sequoia scout and eventually starting her own fund.
Key Takeaways
The Three-Month Rule for Evaluating Exceptional People
Molly's approach to identifying exceptional talent requires a minimum of three months of observation to accurately assess someone's slope of growth. (05:54) She looks for the strangest, most spiky people and tracks which ones start gaining momentum and tackling their previous weaknesses. This timeframe allows her to see genuine progress rather than just initial impressions, helping her distinguish between those who will continue improving versus those who remain stagnant. The key is watching how people allocate their time and what they're neglecting, which reveals their true priorities and growth potential.
Magnetism as a Byproduct of Authenticity
True magnetism comes from living authentically according to one's vocation rather than performing charisma, according to Molly. (15:45) She believes there's a right thing for each person to work on, and when someone aligns with their authentic path, they naturally attract the right people while repelling those who aren't meant to work with them. This authentic magnetism is more durable than performed charisma because it doesn't drain the person and creates deeper, more meaningful connections with those who resonate with their genuine self.
Agency Requires Presence, Not Just Future Planning
Agency isn't just about making moves in the world - it requires being present to both reality and oneself to ensure those moves are in the right direction. (21:54) Molly emphasizes that true agency means being present to your feelings, wants, and needs, not just having the ability to act. Without this presence, what looks like agency might just be movement that isn't authentic to who you are or where you should be going. The most agentic people have high feedback loops from consistently "just doing things" while staying aligned with their authentic path.
Commercial Instincts Can Be Developed Through Exposure
Commerciality - knowing how to capture value you create and having hunger for it - is more learnable than people assume. (36:29) While some people are naturally commercial from childhood, others can develop these instincts by being around highly commercial people and observing how they see the world in terms of money flows and value capture. The key difference between mission-driven founders and purely commercial ones is that moths care so much about their mission that they understand the necessity of the commercial flywheel to achieve their goals.
The Power of Playing Your Own Game
Success comes from creating your own rules rather than trying to win at games others have designed. (45:47) Molly built Moth Fund as an "out of the flow" strategy that only makes sense for her, focusing on attracting people who feel misunderstood rather than competing for obviously credentialed founders. This approach requires sending a clear bat signal that generates as many nos as yeses, ensuring you attract exactly the right people while filtering out those who aren't a good fit. The goal is legitimizing undervalued archetypes rather than playing the traditional venture game.
Statistics & Facts
- Molly requires a minimum of three months to accurately evaluate whether someone is exceptional, as this timeframe allows her to see their true slope of growth and progress trajectory. (05:54)
- 50% of Molly's best investments in Fund One came from direct relationships with founders, while the other 50% came from people in her network who understood what a "moth" looked like. (56:41)
- The context reveals that Molly defines herself as an Enneagram Type 4 while her husband Tom is a Type 7, representing opposite personality types that complement each other well in their relationship. (100:25)
