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. Matt Wilson, Co-Founder & CEO at Jack and Jill, on AI Career Agents, Talent Density, and Building the Next Network-Effect Marketplace

    2D AGO

    Matt Wilson, Co-Founder & CEO at Jack and Jill, on AI Career Agents, Talent Density, and Building the Next Network-Effect Marketplace

    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 mattersHow Jack and Jill avoids the marketplace cold start by winning in “single-player mode” firstWhy Matt is building a flatter, leaner org this time, and staying closer to the actionTalent density in an AI-native company, and why paying above-market is a deliberate strategyWhat “escape velocity” looks like in a two-sided marketplace, and the metric they trackThe long-term moat: network effects over featuresMatt’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.

    36 min
  2. Nicolò Frisiani, Co-Founder & CEO at Lupa, on Building the AI Operating System for Vets, Enterprise Sales, and Scaling at Speed

    MAR 4

    Nicolò Frisiani, Co-Founder & CEO at Lupa, on Building the AI Operating System for Vets, Enterprise Sales, and Scaling at Speed

    Nicolò Frisiani is Co-Founder & CEO of Lupa, the world’s first enterprise-ready AI operating system for veterinary clinics. Lupa has raised over $25m from investors including Singular and Firstminute Capital, and is on a mission to modernise a sector still running on 1980s technology. In this episode, Nicolò shares: Why Lupa started as a consumer app and quickly pivoted to a full-stack operating systemHow note-taking became the wedge product into a much bigger platform visionWhat he learned from sending his co-founder to work as a vet receptionist for a monthThe complexity of selling into PE-backed veterinary groupsWhy speed and momentum drove two fundraises in quick successionThe long-term vision: from clinic OS, to monetisation infrastructure, to unlocking veterinary data for AI-driven medical researchWe also discuss the realities of scaling enterprise SaaS, underestimating sales cycles, hiring challenges, and how a consulting background shapes early-stage founders. If you’re interested in vertical SaaS, AI infrastructure, or how to go from scrappy MVP to enterprise-ready platform, this one is worth your time.

    30 min
  3. George Davis, Founder & CEO at Lorum on Rebuilding Global Clearing, Why Dollars Are Broken, and Building a Payments Only Bank

    FEB 25

    George Davis, Founder & CEO at Lorum on Rebuilding Global Clearing, Why Dollars Are Broken, and Building a Payments Only Bank

    George Davis, Founder and CEO of Lorum. George has been deep in payments for years: Head of Product at TrueLayer, then co-founder of BVNK, and now building Lorum to tackle the hardest layer of the stack: global clearing. We get into: Why payments becomes an obsession if you look closely enoughWhat “rebuilding clearing from the ground up” actually means, in plain EnglishVirtual accounts, ledgering, Swift, and why settlement speed still mattersThe real opportunity: fixing dollar clearing and cross border flowsHow Lorum makes money, and why being “payments only” changes the incentivesThe fundraising sprint, choosing Northzone, and what great investors actually do day to dayThe hardest part early on: banking reality versus licensing theory in the Middle EastHow George runs transparency, morale, and intensity during high growthA simple lesson for founders: do not start a company unless you care deeply about the problem

    27 min
  4. David von Rosen, Founder of Lottoland on Majority Stake Investing, Loving Risk, Dubai’s Energy, and the Steve Jobs Turtleneck Story

    FEB 18

    David von Rosen, Founder of Lottoland on Majority Stake Investing, Loving Risk, Dubai’s Energy, and the Steve Jobs Turtleneck Story

    James sits down with Dr. David von Rosen, the serial founder behind Lottoland and 25 Degrees, and the Principal of the VONROSEN family office, through which he invests globally and pan-sector in fast-growth pre-IPO startups. David does not pretend to have one neat playbook. He prefers volatility, backs ideas that feel genuinely new, and invests like an operator, often taking a significant stake so he can get involved properly. We talk about: Why David prefers fewer bets with bigger ownershipHow he thinks about hiring generalists and spotting motivation over credentialsWhat most people misunderstand about risk, and how his relationship with risk has changed with ageWhy Dubai feels like a magnet for talent, capital, and momentumThe origin story of Lottoland, and the clever regulatory workaround that made it possibleHis future unicorn pick: Tytan TechnologiesDinner party guests, featuring Alex Honnold and RihannaPlus, a brilliant story from David’s past: how his fashion brand ended up on Steve Jobs during an Apple WWDC keynote, and what happened next. If you like founder psychology, unconventional investing, and real operator stories, you’ll enjoy this one.

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

    FEB 11

    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
  6. 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
  7. 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
  8. 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
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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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