Welcome back to the second episode of the Ideas to Impact podcast, powered by Techscaler, where we bring you candid conversations with startup founders and key players in the tech ecosystem. Each episode explores the journey of entrepreneurs who have transformed their ideas into impactful businesses, sharing insights, lessons, and inspiration along the way.
In this episode, we sit down with Rory Buchanan, co-founder of Ask Vinny, to explore how he’s transforming property management through AI and automation. What began as a simple WhatsApp service has evolved into a smart, scalable platform that’s reshaping the rental experience for landlords and tenants alike. We dive into the power of customer feedback, the realities of pivoting in sales strategy, and why relentless user focus and rapid prototyping are central to his approach.
Rory Buchanan, co-founder of Ask Vinny, discusses the company’s evolution from a simple WhatsApp service to an AI-driven property automation platform, emphasising adaptability and customer feedback.
Founded by Rory Buchanan and Johnny Siu during their Antler residency in the UK, Ask Vinny’s AI-driven maintenance service bridges the gap in property management. The platform offers a cost-effective, efficient solution to enhance the renting experience for both landlords and tenants from start to finish.
The conversation covers co-founding with a trusted partner, sales strategy pivots, early-stage fundraising challenges, and the significance of product progress and user engagement. Rory emphasises breaking self-imposed limits, fundraising resilience, and balancing operational pragmatism with tech innovation. He advocates for relentless customer obsession, prototyping with AI tools, and fostering a community-driven mindset.
“I was like, damn, I’m making so much money for these other people. And it’s great, I have the solid foundation of the product that they’ve already built, but I think that I can take the exact same ethos I have there and apply it to my own company.
Rory Buchanan, Co-Founder of Ask Vinny
Rory Buchanan is the Co-Founder of Ask Vinny, an AI-powered property management platform reinventing how residents and property managers interact. By turning everyday building services into seamless, chat-based experiences, Ask Vinny brings concierge-style support to residential living, improving satisfaction while cutting admin overhead for building operators.
Before founding Ask Vinny, Rory built his career in product at companies like Deel, Trustpilot, and Bulb, where he led high-impact initiatives across B2B SaaS and consumer marketplaces. But his path into tech wasn’t traditional. After completing a law degree, he pivoted into the startup world, joining renewable energy disruptor Bulb as a customer service agent. Fueled by curiosity and a desire to solve problems, he taught himself SQL and Python to analyse customer behavior and streamline operations, eventually working his way into product management as the company scaled from 30 employees to over 1,000.
That self-starter mentality has defined Rory’s career ever since. Whether as a product leader or founder, he’s known for rolling up his sleeves to get things done, whether that means coding a solution, rallying a team, or responding to customer needs in real-time. He continued that mindset at Deel, where he learned the power of speed and responsiveness in high-growth environments.
Now at Ask Vinny, Rory blends his deep product expertise with a relentless focus on user experience to reimagine building management for the modern age.
In this episode, we dive into the entrepreneurial journey of Rory Buchanan, co-founder of Ask Vinny, a fast-growing startup transforming the property management space with AI-driven automation. What began as a simple WhatsApp boiler triage tool has evolved into a smart, scalable platform reshaping how landlords and tenants manage issues, communicate, and engage with their buildings.
Rory shares the early origins of the idea, developed during his time at Antler, and how customer feedback, particularly from their very first client in Milton Keynes, shaped the direction of the product. He opens up about the often messy reality of early-stage startups, where adaptability, speed, and constant iteration are essential for survival.
Listeners are taken through Rory’s unconventional path from studying law to becoming a product leader and founder. He reflects on his formative experience at Bulb, where he taught himself SQL and Python just to solve customer problems no one else had time to tackle. That scrappy, solutions-first mindset has defined every step of his career, from working at high-growth companies like Trustpilot and Deel, to building Ask Vinny from the ground up.
The conversation also delves into the emotional and strategic complexities of co-founding with a friend, highlighting the importance of trust, candid communication, and shared ambition. Rory discusses the art of selling a new category product, the lessons learned from hiring a Business Development Representative, and how refining their sales process led to better outcomes and faster customer growth.
We also explore the challenges of raising investment with a product still in motion, including Rory’s reflections on rejection, resilience, and the low close rate most founders face. He talks candidly about what it takes to keep pushing forward, balancing pragmatism with a vision for the future, and how the team tracks meaningful product metrics as they scale.
Whether you’re a founder, product builder, or just curious about what it takes to bring a startup to life, this episode is packed with honest insights on learning by doing, failing forward, and staying obsessively close to your customers.
Listen to the full episode wherever you get your podcasts, and don’t forget to subscribe to stay updated on future conversations with founders and exciting guests.
Connect with Rory Buchanan on LinkedIn and through his website.
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