Who’s Allowed to Win?

Why does venture funding still feel like an exclusive club and who’s paying the price?

In this episode of Human and the Machine, I sit down with Hattie Willis: founder, community builder, and the driving force behind Guestworks and IfWeRaise.

Hattie isn’t here to play by the old rules. She’s quietly redesigning how entrepreneurship is taught, funded, and made genuinely accessible, especially for the talent traditional systems leave out.

We talk about why the VC model remains broken for most, how “pattern recognition” in AI can reinforce old biases, and whether bootstrapping is really empowerment or just a new way of asking underrepresented founders to do more with less. Hattie shares the hard truths on equity, fundraising, and the real work of building communities that don’t just offer support, but actually shift power.

If you’re a founder, investor, or just questioning what it means to create change in a world shaped by algorithms, this conversation will challenge your thinking and maybe even your next move.

Listen in for:

• The nuanced risks of fundraising and why VC isn’t for everyone

• How AI in due diligence can accidentally entrench bias

• Bootstrapping vs. fundraising and what really serves underrepresented founders?

• The role of community as strategy, not just support

• How to stay bold, curious, and human in the era of intelligent machines

If this episode moves you, share it on and keep the tough conversations alive.

Find Hattie Willis and her work here:

- https://www.guessworks.co/corporates

-https://www.ifweraise.com/about