Riding Unicorns: Venture Capital | Entrepreneurship | Technology

Riding Unicorns Productions
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Riding Unicorns is the go-to podcast for anyone interested in venture capital and high-growth 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 candid 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. Harrison Rose, Co-Founder at GoodFit on Mapping Your Market, Modern Go To Market, and Lessons from Building Paddle

    1D AGO

    Harrison Rose, Co-Founder at GoodFit on Mapping Your Market, Modern Go To Market, and Lessons from Building Paddle

    Harrison Rose co-founded Paddle, one of the UK’s standout B2B billing and payments companies. Now he is building GoodFit, a go to market platform helping teams prioritise the right accounts, at the right time, with the right data. In this episode, Harrison breaks down a simple idea most teams still get wrong: before you buy another shiny GTM tool, make sure you are actually selling to qualified customers. He shares how Paddle approached go to market from first principles, why the “execution layer” has exploded (16,000 tools and counting), and why fundamentals like market mapping and qualification still matter most. We also get into what he learned on a 10-year unicorn journey, the reality of hard days (including the moment Paddle’s whole sales team quit), and what motivates him second time around when failure is no longer existential.

    32 min
  2. Ben Freeman, Co-Founder & CEO at Omnea on Building an AI Native Procurement Platform, Talent Density, and Founder Paranoia

    JAN 28

    Ben Freeman, Co-Founder & CEO at Omnea on Building an AI Native Procurement Platform, Talent Density, and Founder Paranoia

    Ben Freeman is the Co-founder and CEO of Omnea, an AI native procurement and supplier management platform used by companies from the mid-market through to enterprise, including Synthesia, Typeform, Spotify, Monzo, Albertsons, and The Adecco Group. Ben’s path to procurement was not obvious. From running a bootstrapped events business in Manchester (and dropping out of uni), to a stint in investment banking at Lazard, to scaling cybersecurity company Tessian in New York, he accidentally discovered just how broken procurement can be inside otherwise world class organisations. In this conversation, Ben breaks down how he found conviction for Omnea through hundreds of user interviews, why procurement is a horizontal problem that touches every employee, and how macro shifts are making procurement a board-level priority. We also go deep on what Omnea is known for internally: talent density. Ben shares how they hired their early team, what “mutual fit” really means, why they are willing to pass on an “8”, and how he thinks about building an enduring company with a flat, player coach org structure. We cover: How to do customer discovery properly (and when to walk away)Why procurement is a huge market hiding in plain sightThe trade off between speed and shipping the right product for enterpriseHiring for traits over skills and what Ben looks for in interviewsFounder paranoia, time management, and staying close to customersBen’s dinner party guests and the future unicorn he is backing

    39 min
  3. Why "AI Visibility" is critical for your brand with James Cadwallader, Co-Founder & CEO at Profound

    12/17/2025

    Why "AI Visibility" is critical for your brand with James Cadwallader, Co-Founder & CEO at Profound

    James and Hector sit down with James Cadwallader, CEO and Co Founder of Profound, to unpack how AI is reshaping the internet and what that means for every brand on the planet. James explains why large language models are not just a new interface, but a fundamental platform shift in how people retrieve information. Instead of humans clicking blue links, user agents now visit the web on our behalf, read content, and answer questions directly. Profound sits in the middle of this change, helping some of the worlds biggest brands understand if and how they show up in AI answers, and then create content that is designed for bots rather than humans. The conversation covers what GEO (generative engine optimisation) actually is, how Profound uses a huge consumer prompt panel and reasoning models to map where AI gets its answers from, and why SEO teams are surprisingly well placed to become the heroes of this next era. James also shares his view on how ads will work inside products like ChatGPT, why this may finally break the search monopoly, and how he thinks marketers will work in a world where AI creates, distributes and measures most of their campaigns. James talks through Profounds rapid journey from idea to working with Fortune 10 brands, the fundraising story with Sequoia, Kleiner Perkins and others, and why this is the last company he plans to build.

    50 min
  4. From Formula 3 to AI Accountants: Ariel Harmoko, Co-Founder & CEO @ Artifact

    12/10/2025

    From Formula 3 to AI Accountants: Ariel Harmoko, Co-Founder & CEO @ Artifact

    Ariel Harmoko is the Co Founder and CEO of Artifact AI. Ariel joined James and Hector for a conversation that moves from race tracks to reconciliation engines. Ariel grew up in Jakarta, was thrown into Go Karts at eight, and went on to race professionally all the way to Formula 3 alongside the likes of Lando Norris and George Russell. That early immersion in high performance teams, engineering and discipline shaped how he now operates as a founder. He shares how a love of maths and science took him to boarding school in the UK, then into machine learning research at Cambridge while still a teenager, working on early diagnosis in medtech and later deploying internal GPT tools at JP Morgan. Today Ariel is building Artifact AI, an “agent accountant” that sits on top of existing ledgers like Xero, QuickBooks and NetSuite. The product tackles two huge problems for accounting firms. Fragmented legacy stacks and chronic staff shortages. Ariel explains how their agents ingest data, reconcile, post to ledgers and learn from human review, and why accuracy, auditability and trust are non negotiable in this space. The conversation covers selling into one of the most conservative industries on earth, founder led FDE style implementations, why advisory is the real margin in accounting, and how vertical AI and agentic workflows could reshape professional services.

    36 min
  5. Building the AI Super Connector with Andrew D’Souza, Founder of Boardy and Clearco

    12/03/2025

    Building the AI Super Connector with Andrew D’Souza, Founder of Boardy and Clearco

    Andrew D’Souza is the Founder of Boardy, the Creandum backed AI super connector reshaping how founders and investors meet and build trust. Before Boardy, Andrew co-founded Clearco, one of the first revenue based financing companies. Clearco deployed over $5bn to thousands of businesses, scaled to six hundred employees, and passed one hundred million dollars in revenue. Andrew is one of the few founders who has built a nine figure company before starting again. Clearco’s early AI work and Andrew’s interest in generative AI since 2020 sparked the idea for Boardy. Boardy is a voice based AI that speaks to founders and investors, remembers context instantly, and makes high quality introductions at scale. What started as a side experiment is now one of the fastest growing AI products in fundraising. We also cover Boardy’s newest chapter. After helping founders secure meetings, term sheets and oversubscribed rounds through his recent campaign, Boardy has launched Boardy Ventures, the world’s first AI led venture fund, allowing him to back the founders he already supports. We explore the journey from bedroom prototype to top tier backing from Creandum, and how Boardy is building powerful emergent network effects. In this episode we get into:  🧠 The Clearco story and lessons from hypergrowth  🤖 Early GPT-3 experiments and the Clear Angel project  📞 Why voice matters and why intelligence beats latency  🎯 How Boardy creates uncannily strong introductions  📈 Network effects and solving the cold start problem  💸 How founders are already closing rounds through Boardy  🧪 The superpowered version now helping founders and VC firms  🧩 The long-term vision from venture partner to AI holding company  🎨 Creativity, identity and why great companies reflect their founders A sharp and thought provoking conversation on AI, networks and entrepreneurial energy.

    47 min
  6. Inside SVB's dramatic acquisition and the Future of UK Venture with Erin Platts, CEO of Octopus Ventures

    11/26/2025

    Inside SVB's dramatic acquisition and the Future of UK Venture with Erin Platts, CEO of Octopus Ventures

    Erin Platts is the CEO of Octopus Ventures and former CEO of Silicon Valley Bank UK & Europe — one of the most pivotal figures in the UK tech ecosystem. In this conversation, Erin opens up in remarkable detail about her personal journey from two decades inside SVB to leading one of Europe’s most active venture firms. She shares the inside story of the SVB collapse — the all-nighters, the adrenaline, the leadership decisions made under extreme pressure, and what it was really like to shoulder responsibility for thousands of founders, operators and employees during a once-in-a-generation crisis. We then explore Erin’s new chapter at Octopus Ventures, and how she's shaping a platform that spans pre-seed to growth investing, powered by the unique capital model of the wider Octopus Group. We discuss the future of the UK ecosystem, the evolution of UK capital markets, and what needs to change to ensure the best founders choose to build and list here. In this episode we dive into:  🔥 The inside view of the SVB implosion — four days, 90 minutes of sleep, and how the team navigated full-blown crisis  🧭 Leadership principles forged through chaos: communication, context and visible leadership  🏦 Why Erin joined Octopus Ventures and how she plans to scale a multi-fund, multi-stage European VC platform  🌍 The capital continuum — and how the UK can close the growth and public-markets gap  ⚡ Why founders underestimate their own agency in shaping the future of the ecosystem  🏛️ Erin’s role in the Capital Markets Industry Taskforce and what a healthier UK exit landscape could look like  🏫 Octopus’ growing footprint in education, financial services, and energy, including the rise of Octopus Legacy This is one of the most candid conversations we’ve recorded — a masterclass in leadership, resilience and building through volatility.

    43 min
  7. How SuperAwesome Built the World’s Biggest Kid Tech Platform with Co-founder Lee Veitch

    11/19/2025

    How SuperAwesome Built the World’s Biggest Kid Tech Platform with Co-founder Lee Veitch

    Lee Veitch is the Co-Founder and Managing Director of SuperAwesome, the world’s leading kid-tech and youth marketing platform. SuperAwesome powers billions of kid-safe digital transactions every month — helping brands like LEGO, Disney, and Nickelodeon connect with young audiences responsibly and safely. Lee takes us behind the scenes of a remarkable 13-year journey — from the early days of fear, frustration, and opportunity, to scaling globally, being acquired by Epic Games, and then buying the business back to continue its mission independently. In this episode we dive into:  👶 Why the internet needed a safe space for kids — and how SuperAwesome built it  📺 The shift from TV to digital — and how the youth ad economy evolved  ⚖️ Balancing commercial success with mission and ethics  💡 The strategic choice not to build a programmatic platform  🧱 Lessons from the Epic Games acquisition and buyback  🔐 How regulation like COPPA and GDPR-K shaped the company’s tech  🌍 Using influence to drive global policy change  🔥 Founder energy, culture, and why humour builds great teams Lee also shares what’s next for SuperAwesome — from global expansion and M&A to building Awesome Intelligence, a new data platform that helps brands understand kids’ digital lives without compromising safety.

    43 min
  8. Pioneering the AI-rollup model in the property management space with Dan Lifshits, Co-Founder @ Dwelly

    11/12/2025

    Pioneering the AI-rollup model in the property management space with Dan Lifshits, Co-Founder @ Dwelly

    The AI rollup transforming property management This week on Riding Unicorns, we sit down with Dan Lifshits, Co-Founder & COO of Dwelly — the AI-first lettings and property management platform reinventing how landlords, tenants, and agents interact. Dwelly is on a mission to modernise the UK rental market by acquiring traditional letting agencies and rebuilding them with technology at their core. The business is growing fast, backed by General Catalyst and other leading investors, combining the operational rigour of real estate with the scalability of AI. Before founding Dwelly, Dan was one of the youngest associates at McKinsey, then helped scale Gett (the ride-hailing company) from early stage to over $1bn in GMV and 1,000+ employees — experience that now shapes Dwelly’s operational DNA. In this episode, we dive into:  🏢 The rollup model — why Dwelly is buying agencies instead of building from scratch  💡 Applying AI to traditional services — from lettings to maintenance and communication  🌍 Moving to Hull — and why the founding team relocated to be closer to their first acquisition  🚀 Turning investor scepticism into conviction: why rollups might define the next decade  🤖 Using data to discover the “perfect process” across thousands of lettings  💼 How to balance being a product builder, operator, and M&A organisation  🔥 Lessons from Gett and McKinsey on scaling complex, real-world businesses Dan also shares his view on the coming wave of AI-enabled rollups, why the UK rental market is “crying out for disruption,” and what founders can learn from industries still running on manual workflows.

    45 min
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Riding Unicorns is the go-to podcast for anyone interested in venture capital and high-growth 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 candid 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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