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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-l ...
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On Season 2, Melissa Kwan (Cofounder of eWebinar) and Todd Parmley (COO) relive their "Journey to $1M" ARR, bootstrapping eWebinar from day one. Each episode goes in depth into one major aspect of the journey, as Melissa and Todd share war stories, mistakes, and lessons learned as they grew the company to a million in annual recurring revenue, over a period of 36 months from product launch. If you’re a bootstrapper who wants a window into the day-to-day lives of other scrappy bootstrappers n ...
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One Wild Ride is the exploration of a more meaningful life. A place where personal stories collide with good business and positive impact. Here we dive deep into the mindset, musings and strategies of incredible humans doing extraordinary things. Theirs are stories of positivity, hope, expansion and evolution. Host Pru Chapman knows good business. As the founder of Owners Collective she has helped over 15,000 founders launch, leverage, and lead their businesses. She's passionate about using ...
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Subscribe to the Reading Unicorns newsletter here. Follow Riding Unicorns on LinkedIn here. Subscribe to the Riding Unicorns YouTube channel here. In this episode of Riding Unicorns, James Pringle and Hector Mason are joined by Mark Beeston, Founder and Managing Partner at Illuminate Financial—a thesis-driven venture capital firm investing in B2B F…
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Subscribe to the Reading Unicorns newsletter here. Follow Riding Unicorns on LinkedIn here. Subscribe to the Riding Unicorns YouTube channel here. This episode sees James Pringle and Hector Mason sit down with Staffan Helgesson, General Partner of Creandum. Creandum is one of Europe's top early stage investors focused on Seed and Series A across a …
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Subscribe to our newsletter here. Follow us on LinkedIn here. Subscribe to our YouTube channel here. Joseph Pizzolato is the Founder & General Partner at Defiant VC, a newly launched venture fund bringing a tech-first approach to investing. Joseph shares his journey from engineering to venture capital, his experiences at Vitruvian Partners and Feli…
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It took eWebinar 16 months to go from idea to product launch, then another 36 months to hit $1M ARR; this is the core theme of this season. That's a total of 52 months from incorporation date. You might have read about companies that get to $1M in a year, much less now with AI startups and the world riding that wave. Those are outliers and not the …
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Subscribe to our newsletter here. Follow us on LinkedIn here. Subscribe to our YouTube channel here. In this episode of Riding Unicorns, we’re joined by Aidan Rushby, Founder & CEO of Carmoola, a fintech company reinventing the way people buy used cars through a seamless, mobile-first car finance experience. Aidan shares his journey from running a …
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Subscribe to our newsletter here. Follow us on LinkedIn here. Subscribe to our YouTube channel here. Mike Smeed, Managing Director at InMotion Ventures, Jaguar Land Rover’s corporate venture capital arm. Mike shares his journey from a career in finance to leading one of the most active CVCs in the UK. He provides unique insights into the role of co…
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When Melissa cofounded eWebinar, she had no idea it was going to be “product-led”. Before becoming an entrepreneur, she had always been in B2B sales and biz dev roles. She was always a sales-led founder as both her previous startups were enterprise SaaS. The word “product-led growth” didn’t even exist in her vocabulary! When she ran out of leads to…
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Subscribe to our newsletter here. Follow us on LinkedIn here. Subscribe to our YouTube channel here. This week on Riding Unicorns, we’re joined by Adam Norris, Founder & CEO of Pure Electric, one of the leading premium electric scooter brands. Adam is also well known for playing a key role in managing the career of his son, Lando Norris, McLaren F1…
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“This is fine as a lifestyle business.” Says every VC with a slight look of disdain after you pitch them your brilliant idea they don’t want to invest in. The industry has given “lifestyle business” such a bad reputation by commonly using it to describe non-venture scalable businesses with less ambitious founders. Only 1% of startups are venture fu…
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Stefano Vaccino is the Founder and CEO of Yapily, a leading open banking infrastructure provider. Stefano shares his unique journey from a career in nanotransistor research and investment banking to discovering his passion for technology and founding Yapily. We explore how open banking regulations like PSD2 inspired him to create a mission-driven c…
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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 epi…
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Should you “do right by your customers” at the expense of the company, your team, and your own wellbeing? Your answer might be “yes”, until you realize a small change that customers would barely feel could mean instant profitability for your bootstrapped startup. Having said that, hindsight is always 20/20. There are some mistakes that you just hav…
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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…
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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 consumer…
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Most companies think the answer to more revenue is to sell enterprise, but they aren't aware of the massive hassle and costs that come with going upmarket. There's no such thing as free money. The bigger the deal, the more attention you need to give your customer. The more customizations you offer, the more versions of your product you have to main…
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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…
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Hiring is one of the biggest challenges every company faces. For bootstrapped startups, this challenge is even bigger as we have to compete against funded companies and tech giants. Part of building a startup is trial and error, throwing things against the wall to see what sticks. Hiring is no different - it’s a learning process that can sometimes …
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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 th…
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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 produc…
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eWebinar was built in a silo for 18 months before the first person signed up for a trial. Melissa and her team had no idea if this business would become “real”, and if people were going to pay for the service. On this episode, Melissa and Todd recount stories of when they knew they were onto something, through customer interactions and feedback, ou…
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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 dyn…
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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 fund Backing transform…
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If you’ve been following Melissa on LinkedIn, you’ll know that she’s a frequent contributor on the platform, sharing lessons and stories from her journey bootstrapping three startups. What you might not know is the backstory of WHY she turned to social selling after running out of leads to sell to. On this episode, Melissa shares her “hacks” of bui…
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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 a…
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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…
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Spending money on marketing is often not an option for bootstrapped startups, at least not enough to make a meaningful impact. Without an abundance of resources, there’s no choice but to get creative. While found-led sales can get you off the ground, your network can exhaust pretty quickly, leaving you with the challenge of figuring out new ways to…
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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 …
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Companies like Amazon and Costco who pride themselves on customer service conditioned consumers (me and you) to think that customers are always right - but, are they? In the faceless world of software, customer demands can be brutal, leading to soul crushing and demoralizing support. Training your customers to respect your team and product sets the…
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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 th…
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15 years ago, Dropbox spread like wildfire with their freemium product and that gave us the impression that free = more users. It deluded companies to think that giving something away for free is a go-to-market strategy, when it’s far from that. Giving away something for free has many negative implications that aren’t often talked about. The most i…
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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 bu…
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Chloe de Winter is the co-founder of Nala, a wildly better underwear brand that has gained a cult following for its comfortable and affordable bras and undies. Nala is dedicated to creating sustainable, stylish underwear that doesn't compromise on comfort or design. Using bio-based fabrics and ethical practices, the brand caters to all genders and …
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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. …
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If you have a great product and offer a commission for people to promote it, they’d happily do it and you’d just make money, right? Not so fast… On this episode, Melissa and Todd recount the painful memories of spending $130k on affiliate marketing over 10 months; an experience Melissa considers the “biggest financial mistake she’s made in her care…
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David Jarvis is the Co-Founder and CEO of Griffin. ​Griffin puts the bank in Banking as a Service. They combine the secure, regulated infrastructure of a bank with the speed and power of modern software into one powerful full-stack BaaS platform. Their goal is to empower companies to embed banking into their products quickly and safely. With purpos…
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Jessica Maguire is an internationally published author, TEDx speaker, and leading nervous system educator who has impacted over 15,000 students worldwide. With a Master’s in Physiotherapy and nearly two decades of experience, Jessica has pioneered a global movement in nervous system education. Through her innovative approaches, Jessica provides cle…
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Sharnee Thorpe is the creative entrepreneur and renowned print designer behind Byron Bay's beloved brand, Wandering Folk. As the founder, owner, and creative director, Sharnee's passion for creating premium picnic essentials has captivated adventure and art lovers worldwide. Her love for nature and exploration blossomed early, leading to a life enr…
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Everyone says you need to measure everything so you can make data-driven decisions on your product. That's exactly the strategy eWebinar DID NOT follow, especially when there's not going to be enough data when you don't have enough users. On this episode, Melissa and Todd shares how they decided on priorities even before having a significant custom…
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Mike Soutar worked in the media and entertainment industry since the mid-1980s, starting as a magazine journalist and editor before becoming a Publisher and Managing Director working across print, digital, and broadcast platforms in the UK and America. In 2000 Mike joined the Board of Britain’s largest magazine publisher, IPC, and was part of the B…
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Founded by Julia and Jordy Kay, Great Wrap is leading the charge with innovative solutions to tackle the staggering 150,000 tonnes of plastic stretch wrap dumped into our landfills annually. Recently awarded B Corp Certification and recognised with numerous awards including as a Category Innovator in the AFR Sustainability Leaders List Great Wrap s…
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George Henry is a General Partner at LocalGlobe. LocalGlobe is a venture capital firm that focuses on seed and impact investments. They have seeded impactful founders since 1999 at places like Citymapper, Improbable, Lovefilm, Moo, Wise, and Zoopla. They invest in startups selling to consumers, small businesses, and enterprises. They are lean, data…
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Jasmin Daly is the Executive Director of Ingrained Foundation, a not-for-profit funding platform taking an interconnected and collaborative approach to improving social and environmental wellbeing. Based on Bundjalung Country (Northern NSW), Ingrained has donated over $2 million in the last 5 years to focus on resilience, well-being, inclusion, div…
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Richard Anton is the Co-Founder and General Partner at Oxx. Oxx partners with the most promising European B2B software companies at the scale-up stage. As a specialist SaaS investor, Oxx provides each entrepreneur with a support system of unique specialist expertise and network, and a culture of unfaltering partnership and absolute conviction. The …
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Erika Geraerts is the founder of cult beauty brand Fluff. Fluff was created in 2018 as an antidote to the current beauty industry narrative, for anyone who thinks that the world doesn't need more products, just better products, and responsible, transparent messaging. Their products are all about keeping it simple: good for your skin, your thoughts,…
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Running a startup is a lot of throwing things against the wall to see what sticks (and what doesn't). The hard truth is, majority of things you do won't work...but you need to do them anyway to find the few things that do. On this episode, Melissa and Todd dives into the 10 go-to-marketing strategies that didn't work for them, why, and what they le…
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Frankie Layton is the founder of The Dirt Company, Australia’s first circular packaging brand. Frankie’s passion for sustainability began while working on superyachts, witnessing ocean waste. With a background in strategic consulting, she launched The Dirt Company to tackle household product packaging waste. Since 2017, The Dirt Company has gained …
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Tim Creswick is the CEO and Founder of Vorboss. Vorboss is a dedicated fibre network and internet service purpose-built for the needs of London’s most demanding businesses. They are the only internet service provider that offers 10Gbps as a minimum—meaning that their network can cope with the demands of the most data-hungry businesses for the next …
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In the last 13 years, Melissa has worked with over 10 marketing agencies/contractors to execute a content strategy. Most couldn't deliver on their promise. It was incredibly frustrating. You may have experienced something similar. The vicious cycle went something like this: → Hire company experienced in digital marketing for min 3-6 months → Get pr…
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Oana Andreea Jinga is a CCO and Co-founder of Dexory. They develop robotics and AI logistics solutions to drive better business decisions. Through their DexoryView platform, they automate data collection and build real-time fed digital twin technology that unlocks insights across all levels of warehouse operations. Oana joins James Pringle and Hect…
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Melissa and Todd talks about how they stay super lead as a bootstrapped startup, how they decide what to and what not to spend money on, and how to avoid money mistakes they've made in the last few years. Takeaways: • What "lean" means especially for bootstrapped startups • The importance of optimizing cost versus being cheap • What to spend money …
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