Tony Jamous first joined Riding Unicorns in January 2023, just after Oyster became a unicorn. Since then, the company has raised its Series D, Tony has moved into the Executive Chairman role, and Hadi Moussa has stepped in as CEO.

In this episode, James sits down with both Tony and Hadi to unpack what really happens when a founder hands over the CEO role in a high-growth company. They discuss why Tony knew Oyster needed a different kind of leader for its next stage, how the search process unfolded, and what Hadi has focused on in his first months in the role.

They also go deep on scaling leadership, building operational rhythm, giving effective feedback, and how to turn a strong remote culture into a genuinely high-performing organisation. The conversation then shifts to the future of global employment, the impact of AI on hiring, and why Oyster still sees a huge opportunity ahead.

A candid episode on succession, self-awareness, scale, and what it takes to lead a mission-driven company through its next chapter.

Topics covered:

• Why Tony stepped aside as CEO
• How Oyster prepared for a leadership transition
• What Hadi is changing in his first months as CEO
• Founder-led vision vs operator-led execution
• Building a high-performing remote team
• Feedback, vulnerability, and leadership maturity
• AI’s impact on hiring and global talent
• The future of Oyster and global employment

Nikola Mrkšić is the Co-Founder and CEO of PolyAI, one of the world’s leading voice AI companies, helping enterprises automate customer service through conversational AI at massive scale.

Before PolyAI, Nikola was a machine learning researcher and part of the team behind Siri. In this episode, he joins James to unpack what the world is only now starting to understand about voice AI, why most automation still misses the point, and how PolyAI has built a full stack enterprise product that goes far beyond simply reducing call queues.

They discuss how PolyAI is used by major brands across hospitality, utilities, retail, banking and insurance, and why the real opportunity is not just handling calls, but turning the contact centre into an intelligence layer for the whole business. Nikola also explains why enterprise voice AI is harder than it looks, where the moat really sits, and why owning the models and the application layer matters.

The conversation covers Siri, Gordon Ramsay, pricing power, Nvidia, enterprise stickiness, and what it takes to build a category leader from Europe.

Topics include:

• Why Siri was too early for the vision it was aiming at
• Why PolyAI focused on the step between clunky IVR and true AI assistants
• How voice AI can improve revenue, customer experience and operational insight
• Why enterprise deployments become hard to rip out
• The difference between real voice AI companies and wrappers
• Whether voice AI is becoming commoditised
• How PolyAI thinks about pricing, margins and defensibility
• Why Nikola believes many “AI companies” are borrowing from the future
• Gordon Ramsay as a customer and brand partner
• Nikola’s future unicorn pick: Paid.ai

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.