Riding Unicorns: Venture Capital | Entrepreneurship | Technology

Mandeep Singh is an angel investor and co-founder and former CEO of Trouva, a marketplace for independent boutiques that was acquired by Made.com.Mandeep takes us through his journey from founding Trouva, navigating its growth, and the eventual exit, to his current role as an active angel investor with a portfolio of over 80 companies.In this episode, we dive into:The story behind Trouva’s evolution, including the pivots and lessons learned from building both B2B and consumer propositionsThe challenges of building a marketplace, balancing stakeholders, and achieving product-market fitReflections on fundraising, scaling, and navigating acquisitionsMandeep’s approach to angel investing, what he looks for in founders, and his perspective on valuation at the earliest stagesLessons on resilience, grit, and determination, drawn from his entrepreneurial journeyMandeep also shares unique insights into the European startup ecosystem, including the challenges of scaling marketplaces and the capital landscape for ambitious founders.Whether you’re a founder, investor, or just curious about the behind-the-scenes of startup life, this episode is packed with valuable takeaways. Don’t forget to like, subscribe, and follow The Riding Unicorns podcast on your favourite platform and stay connected with us on social media for more inspiring episodes! 🎙️🦄

Tim Chong is the Co-Founder and CEO of Yonder, a modern lifestyle rewards credit card designed for young city adventurers.Tim shares his journey from growing up in Australia and a career in consulting to working at ClearScore and ultimately founding Yonder. We delve into the evolution of the Yonder product and brand, from solving credit challenges for expats to becoming a lifestyle companion for urban explorers.In this episode, we explore:The pivotal insights that shaped Yonder’s unique proposition and its focus on restaurant and travel rewardsLessons on customer discovery, why it’s crucial for founders, and how to execute it effectivelyBuilding a high-frequency, habit-forming product that becomes a primary card for usersThe importance of organisational design, culture, and language in scaling startupsInsights into raising funding through challenging market conditions and the importance of patience in building a generational companyTim also reflects on his role as a first-time founder, the art of adapting as a CEO, and why building great companies takes time, vision, and conviction.Whether you’re a founder, operator, or just curious about building products and brands, this episode is packed with actionable insights and inspiration. 🎙️

This week on Riding Unicorns, we’re joined by Romina Savova, Founder & CEO of PensionBee, the platform transforming how people manage their pensions. With over 260,000 customers and £5.5 billion in assets under management, PensionBee has become a household name in the UK. Romina shares the journey of building a public company that empowers consumers to take control of their retirement savings.In this episode, we explore: 🎙️ Romina's career shift from investment banking to founding PensionBee🔍 How PensionBee approached the complexities of trust-building in the pensions industry🏟️ Their thoughtful brand partnerships, including sponsorship of Brentford FC and National Geographic💡 The decision to go public, raising £55 million and the benefits of transparency and simplified ownership structures🇺🇸 The exciting expansion into the US market and the parallels between UK and US pension landscapes👩‍💼 Hiring strategies that prioritise internal progression and a deep understanding of customer needsRomina also shares insights into navigating the political landscape surrounding pensions, the importance of long-term thinking, and how PensionBee stays focused amidst external noise. Plus, don’t miss her Future Unicorn prediction and a fascinating dinner party guest list that blends business and politics!Tune in to hear how Romina and her team have built PensionBee into a trusted brand and what’s next for the company as they continue their mission to give consumers “extra time” in retirement. 🚀Enjoying Riding Unicorns? Don’t forget to subscribe, rate, and share on your favourite podcast platform! 🎧

This week on Riding Unicorns, we're joined by Dom Hallas, Executive Director at the Startup Coalition, the policy voice for UK tech startups and scaleups. Dom brings a wealth of insight into the intersection of tech, venture, and public policy, offering a fascinating look into the state of the UK ecosystem during a time of governmental and economic change.Dom discusses the Startup Coalition's mission to advocate for startups and investors by addressing key challenges such as access to talent, funding, and regulatory clarity. He also shares valuable perspectives on how policy can shape the future of startups across areas like AI, climate tech, and FinTech.In this episode, we explore: 🎙️ The impact of the new UK government and Autumn Budget on startups and investors📊 The state of venture funding, including changes to tax incentives, capital gains, and carried interest📍 Regional disparities in startup funding and the Coalition's "Funding the Underfunded" project tackling inequalities across gender, race, class, and geography🤖 The future of AI regulation and how the UK can become a global leader in building and applying AI technologies💡 Opportunities for the UK to leverage its strengths in sectors like finance and healthcare to remain competitive on the global stageDom also shares his personal passion for football and sports, offering a light-hearted end to an episode packed with actionable insights for founders, investors, and policymakers alike.Don’t forget to like, subscribe, and follow The Riding Unicorns podcast on your favourite platform and stay connected with us on social media for more inspiring episodes! 🎙️🦄

Ron Levin is the Managing Partner at Alumni Ventures, the most active venture capital firm in the US. Hector spoke to Ron to discuss his journey from entrepreneur to investor and his insights on scaling ventures and building impactful companies.Ron shares his fascinating career story, from organising trading card shows as a teenager to founding the travel-tech unicorn TravelPerk and eventually joining Alumni Ventures, where he leads their dedicated Seed Fund. The conversation dives into:Ron’s unique career trajectory, blending tech, travel, and entrepreneurshipFounding TravelPerk and the lessons learned from pivoting earlyAlumni Ventures' innovative model and how they empower founders while co-investingThe importance of serendipity, curiosity, and acting on opportunities in building a careerHis philosophy on investing for impact and solving big societal problemsThis episode is packed with wisdom and actionable advice for founders, investors, and anyone interested in venture capital and entrepreneurship.Don’t forget to like, subscribe, and follow The Riding Unicorns podcast on your favourite platform and stay connected with us on social media for more inspiring episodes! 🎙️🦄

Martin Sokk is the Co-Founder and CEO of Lightyear. He joined Hector to discuss his journey from product management at Wise (formerly TransferWise) to building a company revolutionising retail investing in Europe.Martin shares how his product-driven mindset and relentless curiosity have shaped his career, offering insights into creating 10x products, scaling startups, and understanding customer needs through direct engagement. The conversation also dives into:Lightyear’s mission to transform Europe’s outdated and costly investing infrastructureThe challenges and opportunities of building a pan-European fintech solutionLessons learned from Wise and the importance of fostering entrepreneurial talentThe role of resilience in navigating crises and maintaining focus on long-term goalsMartin’s story is packed with actionable advice and inspiration for founders, operators, and anyone passionate about fintech innovation.Don’t forget to like, subscribe, and follow The Riding Unicorns podcast on your favourite platform and stay connected with us on social media for more inspiring episodes! 🎙️🦄

In this episode of Riding Unicorns, James is joined by Matt Chandler, Principal at Octopus Ventures, one of Europe’s leading early-stage venture capital firms. Known for his focus on consumer tech, Matt shares his journey from aspiring oil painter to venture capitalist, weaving creativity into every step of his career.Matt discusses the unique dynamics at Octopus Ventures, including their thematic investment approach and their mission to back transformative startups across sectors like gaming, consumer AI, and niche communities. He provides fascinating insights into the "practicalities of change," lessons learned from his entrepreneurial past, and how to maintain focus on core customers during periods of growth.The conversation dives into Octopus’s recent investments, including their backing of Onibi, a groundbreaking MMO gaming platform introducing innovative physics to user-generated worlds. Matt also explores overlooked themes in venture capital, including loneliness, consumer AI, and the evolving world of niche communities.This episode is packed with actionable insights for founders and investors alike. Tune in to hear how Octopus Ventures is championing underdog consumer startups and how Matt’s creative approach is shaping the future of venture capital.Don’t forget to like, subscribe, and follow The Riding Unicorns podcast on your favourite platform and stay connected with us on social media for more inspiring episodes! 🎙️🦄

Sasha Kaletsky, Managing Partner at Creator Ventures, joins James Pringle on Riding Unicorns to discuss his journey into venture capital, the evolution of Creator Ventures, and the unique insights creators bring to consumer internet investing.In this episode, Sasha dives into:The transition from an investment club to a $20M fundBacking transformative startups like beehiiv, Praktika.ai, & ElevenLabsLeveraging creator expertise to navigate social media strategies and consumer trendsThe importance of team and market defensibility in early-stage investingSasha also shares his views on running a nimble, founder-led fund, scaling sustainably, and the future of AI-driven consumer products.This is a must-listen for anyone interested in consumer-focused venture capital and the intersection of creators and startups.Don’t forget to like, subscribe, and follow The Riding Unicorns podcast on your favourite platform and stay connected with us on social media for more inspiring episodes! 🎙️🦄

Rory Sutherland, Vice Chairman of Ogilvy UK, joins James Pringle and Hector Mason on Riding Unicorns to delve into the fascinating intersection of behavioural science, marketing, and business strategy. With a career dedicated to understanding human decision-making, Rory shares his unique perspective on how psychological insights can unlock growth and create competitive advantages in today's business landscape.In this episode, Rory explores why even the most brilliant ideas can fail without the right marketing approach and how concepts like the Netflix subscription model and the reliability of brands like McDonald's and Five Guys build customer trust through consistency. He introduces the concept of “inshittification” — when successful companies lose their way by prioritising profits over user experience — and critiques the tech industry’s obsession with automation at the expense of user needs.Rory’s thought-provoking insights touch on everything from counterintuitive customer behaviour and the hidden power of psychological hacks to why founders need to consider both product and distribution as essential locks to unlocking success. This episode offers practical takeaways for founders, VCs, and creatives on how to better align products with consumer psychology and navigate today’s competitive market.Listen now for Rory Sutherland’s refreshing take on behavioural science and its unexpected impact on business growth.Don't forget to like, subscribe, and follow The Riding Unicorns Podcast on your favourite podcast platform and stay connected with us on social media to never miss an episode! 🎙️🦄

Vidu Shanmugarajah is a Partner at GV (formerly Google Ventures), where he invests in transformative tech companies across Europe. In this episode of Riding Unicorns, Vidu joins James Pringle and Hector Mason to share his journey from corporate law to venture capital, highlighting how his unique background has shaped his approach to investing.Vidu discusses his atypical career path, starting as an M&A lawyer before transitioning to private equity and eventually venturing into tech as an entrepreneur and investor. He sheds light on GV's distinct model as an independent venture firm backed by Alphabet, explaining how it leverages Alphabet’s resources while maintaining a startup-focused ethos. Throughout the conversation, Vidu offers insights into his investment strategy, emphasizing the importance of identifying standout founders, the growing role of AI, and the value of diversity in venture capital.This episode provides a compelling look into the mindset of a successful VC, the nuances of investing in tech, and the evolving landscape of European startups. Whether you’re a founder, investor, or just curious about the venture capital world, you won’t want to miss Vidu’s insights on building and scaling impactful tech companies.Don’t forget to like, subscribe, and follow The Riding Unicorns podcast on your favourite platform and stay connected with us on social media for more inspiring episodes! 🎙️🦄