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 The conversation also dives into:Lightyear’s mission to transform Europe’s outdated and costly investing infrastructureThe challenges and opportunities of building a pan-European fintech solutionLessons learned from Wise and the importance of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! 🎙️🦄

Edwina Johnson is the General Manager of MoneyGram Online International, responsible for overseeing the company’s digital consumer business outside of North America. In this episode of Riding Unicorns, Edwina joins James Pringle and Hector Mason to talk about her diverse career, ranging from working with startups to corporate roles, as well as her experience as an angel investor and startup advisor.Edwina shares her unique journey, beginning in digital media and advertising, co-founding an ad tech startup, and eventually moving into fintech, where she played a pivotal role at Startup Bootcamp and Alloy. She discusses the challenges and rewards of transitioning from a fast-growing startup to a well-established institution like MoneyGram, shedding light on the major shifts needed for traditional businesses to stay competitive in a digital age.Throughout the conversation, Edwina emphasises the importance of supporting underrepresented founders and shares insights from her own angel investing criteria, which focuses on B2B fintech, regtech, and SAS businesses led by founders from underestimated backgrounds. She also highlights the need for diversity in tech, particularly in the fintech space, and the barriers still present in early-stage investment networks.This episode offers valuable lessons in career adaptability, building diverse teams, and fostering innovation across sectors. If you’re interested in the intersection of fintech, startup culture, and angel investing, you won’t want to miss this episode.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 for more exciting episodes! 🎙️🦄

Paul Yacoubian is the Founder and CEO of Copy.ai, a company revolutionising the way businesses create marketing and sales copy by automating workflows with AI. Founded in 2020, Copy.ai initially helped distribute the value of GPT-3, but has since expanded to build an enterprise product streamlining go-to-market efforts for companies globally. In this episode, Paul joins hosts James Pringle and Hector Mason to discuss his journey from an accounting and hedge fund career to becoming a leading AI entrepreneur.They dive deep into Paul's entrepreneurial roots, the early days of Copy.ai, and how his experience working with venture-backed companies influenced his approach to building scalable solutions. Paul also shares insights on the evolving role of AI, how large language models are reshaping business processes, and why he believes in the future of automated business operations.The conversation touches on the challenges and opportunities in the AI space, the importance of talent density in startups, and how companies can leverage AI to drive growth. Paul’s passion for innovation shines through, offering founders, VCs, and anyone interested in the tech space valuable takeaways about building, scaling, and navigating the future of AI-driven companies.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! 🎙️🦄

Charles Wells is the Founder and CEO of HelloSelf, a technology business focused on personalised psychological advice aimed at self-betterment. In this episode, Charlie joins hosts James Pringle and Hector Mason to discuss his eclectic career in marketing, charity, angel investing, and entrepreneurship, as well as the story behind HelloSelf. The business provides personalised online therapy designed to help people feel better, faster and stay better, longer, and Charlie shares how his near-death experience inspired him to dive into the brain tech space and focus on mental health.Throughout the conversation, Charlie discusses his mapping of the emerging neurotechnology space, breaking it down into chemicals, hardware, and software categories. He also talks about the massive potential of AI in understanding our brains, while highlighting the importance of therapy that empowers individuals to become their own therapists.Charlie’s extraordinary journey, which includes surviving a category five brain haemorrhage and undergoing extensive neuro-rehabilitation, has profoundly shaped his outlook on life and business. His commitment to brain health and earth health drives his work, and his story offers valuable lessons about resilience, focus, and the power of incremental self-improvement.Curious about how HelloSelf could help you? HelloSelf are offering taster sessions with psychologists to give you a personalised glimpse into their services. Whether you're considering therapy for yourself or want to learn more about their approach to mental wellbeing, these no-obligation sessions are designed to help you take the first step toward feeling better, faster. Learn more and book your session here.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 for more episodes! 🎙️🦄

Simon Mellin is the Founder and CEO of The Modern Milkman. ​Their business started as a local milkround inspired by David Attenborough's Blue Planet and the need to reduce plastic waste. In the space of a few short years, they've grown from four friends and a truck to a vast network of milkmen and women working tirelessly to reduce consumer waste. Their mobile tech supports their 'eco-warriors on earlies' by connecting them to their customers via online ordering and driver apps, facilitating convenient doorstep deliveries. The tech also connects them to their network of independent dairies, farmers and suppliers who are mutually committed to sustainable produce and plastic-free packaging. Their mission is to revolutionise consumer habits by delivering fresh ways to return and reuse packaging, shop ethically and feel good about convenience.Simon joins James Pringle and Hector Mason to discuss key lessons from moving from farmer to founder, the idea behind The Modern Milkman, business expansion to the US, & so much more. Don't forget to like, subscribe, and follow The Riding Unicorns Podcast on our socials and your chosen podcast platform to stay up to date! 🎙️🦄