Riding Unicorns: Venture Capital | Entrepreneurship | Technology
Riding Unicorns is a podcast featuring the world's best minds from venture and startups. Hosted by VCs James Pringle and Hector Mason, the show explores what it takes to build and back successful tech unicorns. Each episode features conversations with top founders, operators, and investors unpacking the strategies, challenges, and insights behind scaling category-defining companies. From fundraising and product-market fit to hiring, growth, and beyond, no topic is off-limits. Whether you're a founder, VC, angel investor, or just curious about the world of startups, you’ll find valuable takeaways in every episode.
Riding Unicorns: Venture Capital | Entrepreneurship | Technology
Matt Wilson, Co-Founder & CEO at Jack and Jill, on AI Career Agents, Talent Density, and Building the Next Network-Effect Marketplace
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This week on Riding Unicorns, Matt Wilson returns to the podcast. Matt previously joined us in September 2022 to talk about Omnipresent, which has since been acquired by Deel. He is now back building Jack and Jill, one of the most talked-about venture-backed companies in Europe right now.
Jack and Jill is bringing conversational AI to job hunting and hiring, with two agents built for two audiences:
- Jack, an AI agent for individuals that learns who you are, what you want, and monitors the job market for you, while also helping with career coaching, CVs, and interview prep.
- Jill, an AI agent for companies that learns what you are hiring for, then works with Jack to make high-signal introductions at scale.
In this episode, we cover:
- Why careers and hiring remain massively under-optimised, and why that matters
- How Jack and Jill avoids the marketplace cold start by winning in “single-player mode” first
- Why Matt is building a flatter, leaner org this time, and staying closer to the action
- Talent density in an AI-native company, and why paying above-market is a deliberate strategy
- What “escape velocity” looks like in a two-sided marketplace, and the metric they track
- The long-term moat: network effects over features
- Matt’s future unicorn picks, plus dinner party guests (with Steve Jobs, Reid Hoffman, and a very specific competitive curiosity)
If you care about AI agents, marketplaces, or how recruiting changes when everyone has an AI working on their behalf, you’ll enjoy this one.
