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In this episode of Human and the Machine, we go deep with Hattie Willis—a founder, community builder, and the powerhouse behind Guestworks and If We Raise. Hattie has been quietly (but powerfully) redesigning the startup landscape to make it more equitable for those who’ve historically been left out, especially underrepresented founders.

We dig into the uncomfortable truths behind venture funding: why the system was never built for everyone, how “pattern recognition” (even in AI) can reinforce bias, and why not every founder needs to play the VC game. Is bootstrapping really empowering—or just a new way of asking people to do more with less? Hattie shares what she’s learned on the frontlines and why community isn’t just a support system—it’s infrastructure, strategy, and resistance.

Timestamps:
0:00 Intro & Hattie’s mission
5:20 The broken VC model—who really benefits?
14:40 How AI is entrenching bias in startup funding
22:15 Bootstrapping vs fundraising: which path?
31:40 The power (and limits) of community
41:00 Rewriting the rules: what would you build first?
51:15 What does it mean to be human in the age of intelligent machines?

Learn more about Hattie Willis and her work:
🔗 Guestworks: https://www.guessworks.co/corporates
🔗 If We Raise: https://www.ifweraise.com/about

If this conversation made you rethink what’s possible, subscribe for more bold conversations on how technology is changing not just what we build, but who gets to build it. Drop your thoughts in the comments—let’s keep asking the tough questions.

All the zest 🍋