Riding Unicorns: Venture Capital | Entrepreneurship | Technology

Riding Unicorns
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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.

  1. How Cleo Reached $400M ARR: Barney Hussey-Yeo on AI, Growth, and Building a Consumer Fintech Unicorn

    1d ago

    How Cleo Reached $400M ARR: Barney Hussey-Yeo on AI, Growth, and Building a Consumer Fintech Unicorn

    What does it take to build an AI company a decade before the world realises AI is the future? In this episode of Riding Unicorns, James and Hector sit down with Barney Hussey-Yeo, Founder & CEO of Cleo, the AI financial assistant helping millions of consumers make smarter money decisions. Barney started building Cleo years before ChatGPT brought AI into the mainstream. Today, Cleo has grown into one of the UK's leading fintech success stories, reaching $400M ARR and becoming a category-defining consumer AI company. The conversation explores the realities of scaling from zero revenue to hundreds of millions in ARR, surviving the shift from the ZIRP era to COVID, and building a product-led company that endured long before AI became fashionable. Barney also shares how AI is transforming the way Cleo operates internally, why every executive team member is now shipping code, and how founder behaviour, company culture, and execution speed are changing in the age of AI. Topics Covered: • Building an AI company before the AI boom  • The origins of Cleo and the vision for an AI financial assistant  • Growing from $0 to $400M ARR  • Why the first $100M is the hardest milestone  • Surviving COVID and finding product-market fit  • Building data moats and defensibility in AI  • Why AI has transformed customer acquisition  • How Cleo uses AI internally across engineering and operations  • The rise of AI-native companies and the future of work  • Why some employees thrive with AI and others fall behind  • The best AI tools Barney is using today  • Advice for founders on fundraising, execution, and building great products  • The next generation of AI startups and future unicorn predictions A candid conversation about ambition, execution, AI, and what it really takes to build a generational technology company.

    25 min
  2. The Future of Finance is AI-Native: Jonathan Sanders, CEO of Light, on Organic Software, AI Agents, and Rebuilding Business Finance

    Jun 10

    The Future of Finance is AI-Native: Jonathan Sanders, CEO of Light, on Organic Software, AI Agents, and Rebuilding Business Finance

    What happens when software adapts to humans, rather than humans adapting to software? In this episode of Riding Unicorns, James and Hector sit down with Jonathan Sanders, Founder & CEO of Light, the AI-native finance platform redefining how businesses manage money. Jonathan's journey spans investment banking, consulting, Pleo, founding Juni, and now building Light. Along the way, he has developed a unique perspective on technology, AI, and what the next generation of business software will look like. The conversation explores Jonathan's concept of "organic software" where AI agents learn, adapt, and operate alongside teams, reducing complexity and transforming finance from a reporting function into a strategic intelligence layer. Jonathan shares real-world examples of AI agents managing company spend, monitoring compliance, automating finance workflows, and generating insights that would have been impossible just a few years ago. The discussion also covers founder psychology, building through uncertainty, AI-first organisations, and how leadership teams must evolve in a world where software development, product design, and operations are increasingly powered by AI. Topics Covered: • Jonathan's journey from finance and consulting into startups • Why founding a company is one of the hardest ways to create change • The concept of "organic software" and AI-native business tools • How AI agents learn from company behaviour and improve over time • Building finance software that tells stories instead of generating reports • Real-world examples of autonomous finance workflows • Why AI is changing the role of CFOs and finance teams • How Light uses AI internally across product, engineering, and operations • The rise of AI-first organisations and new ways of working • Founder resilience, stress, and the realities of building companies • Why software development is changing faster than most people realise • The future of business operations in an AI-native world This is a conversation about the next generation of software, the future of work, and what happens when AI becomes a true operating system for businesses.

    29 min
  3. Steve Domin, Founder & CEO @ Duffel – Rebuilding Travel Infrastructure, Surviving COVID, and the Future of API-First Companies

    May 20

    Steve Domin, Founder & CEO @ Duffel – Rebuilding Travel Infrastructure, Surviving COVID, and the Future of API-First Companies

    Steve Domin, Founder & CEO of Duffel, the company rebuilding the infrastructure layer of the global travel industry. Duffel is taking on one of the most complex and outdated sectors, creating modern, developer-first APIs for flights, hotels, and more. Backed by investors including Index Ventures and Benchmark, the company has raised over $50M to transform how travel is bought and sold. Steve shares the journey of building Duffel from scratch, including:  Why the travel industry is fundamentally broken  The insight that led to Duffel’s API-first approach  Building deep supply-side integrations with airlines and incumbents  Navigating COVID when travel demand dropped to zero  The painful reality of scaling, resetting, and rebuilding product-market fit  Where long-term defensibility comes from in complex infrastructure businesses We also explore:  What makes companies like GoCardless “talent factories”  How AI is changing how modern engineering teams are built  The future of smaller, highly efficient companies  Steve’s view on the next generation of AI-native products This is a masterclass in persistence, infrastructure thinking, and building through uncertainty.

    26 min
  4. Building the backbone of AI with Mahdi Yahya, Co-Founder @ Radiant on Compute, Power and the Future of Infrastructure

    May 13

    Building the backbone of AI with Mahdi Yahya, Co-Founder @ Radiant on Compute, Power and the Future of Infrastructure

    Mahdi Yahya, Founder and CEO of Ori, is now part of Radiant following its partnership with Brookfield. Mahdi is building at the centre of one of the most important shifts in technology: the global race to scale AI infrastructure. We cover:  From telecoms to data centres: lessons from building infrastructure businesses from age 20  Why Ori chose the harder path of building for a future that did not yet exist  What “AI infrastructure” actually means, from GPU clusters to orchestration software  The Radiant model: combining capital, power, compute and software into a single platform  Why AI is becoming sovereign infrastructure and what that means for governments  Where value will accrue in the AI stack across hardware, infrastructure and applications  The importance of vertical integration and marginal gains in a capital-intensive market  Two pivotal decisions that shaped the company, including early acquisition and moving into physical infrastructure  Founder resilience and the simple rule: stay alive Mahdi also shares his perspective on the next wave of AI companies, the opportunity in inference, and why robotics could be the next breakout category. This is a conversation about building at civilisational scale and what it takes to operate where technology, capital and infrastructure collide.

    27 min
  5. Charlotte Palmer, VP of Venture Capital at Integra Global Advisors on Backing Emerging Managers, Access, and Venture Fundraising

    May 6

    Charlotte Palmer, VP of Venture Capital at Integra Global Advisors on Backing Emerging Managers, Access, and Venture Fundraising

    This week on Riding Unicorns, we’re joined by Charlotte Palmer, Vice President of Venture Capital at Integra Global Advisors. Charlotte sits on the other side of the table as an LP, backing emerging venture funds globally. In this episode, she lifts the lid on how LPs actually evaluate VCs, what really matters beyond headline performance, and why many GPs still get fundraising wrong. We cover: • How LPs really underwrite venture funds and why early DPI is often misunderstood • What matters more than performance in the early years of a fund • Why access and ownership drive returns more than anything else • The reality of backing emerging managers and why smaller funds win • Team dynamics, attribution, and how LPs assess partners under the hood • Why fewer funds are getting backed and what’s changed in the market • The shift in venture towards early-stage and how late-stage AI impacts LP strategy • Portfolio construction from an LP perspective and how diversification actually works • The role of co-investments and why LPs increasingly lean into them • How GPs can create urgency in fundraising and what actually cuts through Charlotte also shares practical advice for GPs, including how to re-engage LPs, how to position a fund without strong DPI, and why most outreach fails to land. A clear, honest view from the LP side on what it takes to get backed and build a fund that lasts.

    30 min
  6. Inside Fuse Energy: Alan Chang on Building a $5B Energy Giant and Chasing £1B ARR

    Apr 29

    Inside Fuse Energy: Alan Chang on Building a $5B Energy Giant and Chasing £1B ARR

    This week on Riding Unicorns, we welcome back Alan Chang, Founder and CEO of Fuse Energy. Since his last appearance, Fuse has scaled rapidly, reaching a $5B valuation and setting its sights on £1B ARR. In this episode, Alan breaks down what it really takes to build a full-stack energy company from scratch, and why solving energy is one of the hardest and most important challenges of our time. We cover: • Why lowering the cost of energy is a trillion-pound opportunity  • The reality of building in a deeply complex, regulated industry  • What it actually means to “buy the grid” and why it matters  • How Fuse has already reduced energy costs by 15%  • The next big product: plug-and-play solar and battery for every home  • Why time, not capital, is the biggest constraint in building a company  • Hiring world-class engineers and building a high-performance culture  • Lessons from Revolut and applying them to energy  • Why the best founders are obsessed with speed, not comfort Alan also shares his mindset as a founder, why he rarely looks back at achievements, and why he’s more convinced than ever that this problem can be solved. Clear thinking on how to build a generational company in one of the world’s most complex industries.

    21 min
  7. What Makes a Top VC Fund Today? Dave Neumann at Schroders Capital on LP Thinking, DPI and Venture Returns

    Apr 22

    What Makes a Top VC Fund Today? Dave Neumann at Schroders Capital on LP Thinking, DPI and Venture Returns

    What does a genuinely great VC fund look like today, from an LP’s perspective? In this episode, James and Hector are joined by Dave Neumann, Investment Manager at Schroders Capital, one of the most experienced institutional investors in venture. With a career spanning decades and exposure to top-tier global funds, Dave shares how leading LPs actually evaluate venture firms, and where many GPs get it wrong. The conversation covers what separates top quartile funds from the rest, why venture is increasingly about building a firm rather than just making investments, and how the best managers create a long-term flywheel across talent, track record and capital. They also go deep on often overlooked topics including DPI, liquidity, fund size, and portfolio construction. Dave explains why access is everything in venture, why consistency matters more than one-off performance, and how LPs think about returns in a world where companies stay private for longer. A sharp, practical look at venture through the LP lens and what it takes to build a durable, high-performing fund. Topics Covered  What defines a top VC fund today  The LP perspective on venture performance  Why venture is about building a firm, not just investing  Top quartile vs lower quartile returns and the compounding effect  Talent, incentives and the VC flywheel  Portfolio construction myths vs reality  Fund size and where returns are really made  DPI, liquidity and secondaries in Europe  How LPs think about risk, time horizons and outcomes  Why access is the biggest advantage in venture

    28 min
  8. Tony Jamous & Hadi Moussa at Oyster HR on leadership transition, CEO succession and unlocking global talent

    Apr 15

    Tony Jamous & Hadi Moussa at Oyster HR on leadership transition, CEO succession and unlocking global talent

    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

    41 min
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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.

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