AskVinny’s journey from a WhatsApp boiler triage tool to a high-growth PropTech platform is a masterclass in moving fast, staying close to the customer, and building while flying. In this blog, we dive deep into how founders Rory Buchanan and Johnny Siu built momentum through rapid pivots, real-world feedback, and grit-fuelled execution.
Rory has also shared his journey on CodeBase’s Ideas to Impact podcast, powered by Techscaler — which you can listen to or watch below — and explored his reasons for joining Techscaler, along with the programme’s impact on AskVinny so far, in his founder case study. Now’s your chance to see how it all connects.
From Boiler Fixes to B2B SaaS: A Relentless Pivot Strategy
AskVinny’s early days were far from glamorous. What started as a boiler triage service shared over social media became a profitable micro-business within hours. But just as quickly as it began, the team realised the idea wasn’t scalable. That awareness, and the willingness to abandon good ideas in pursuit of great ones, became a defining characteristic of their journey.
Rather than spend months crafting business plans or debating strategy, the founders embraced action. Drawing on their experience in the Antler incubator, they sidestepped the common trap of “analysis paralysis” and instead focused on execution. This approach led them to pivot again and again, from point solutions to a more comprehensive B2B offering - always expanding the scope in response to customer needs and market viability.
"Build the Plane as You Fly It": Scaling Through Imperfection
In our recent interview with AskVinny Founder, Rory Buchanan, he explained the company's growth through his metaphor of “building the plane while flying it.” As a high-growth company, the team accepted that software engineering would remain a bottleneck and leaned into rapid development and customer delivery regardless.
Rather than wait for perfection, they put their foot on the gas, prioritising growth even when the product wasn’t fully ready. This willingness to sell ahead of full readiness, while staying up until 3 or 4am to fix issues, proved essential in creating a feedback loop between sales and product development.
Customer Obsession at the Core
The AskVinny team is relentless in their pursuit of customer insight. A key turning point came from a customer in Milton Keynes who opened their entire operation to the startup. The founders embedded themselves in their operations, attended internal meetings, and used that proximity to design tailored solutions. That same customer later became an investor, a testament to the strength of the relationship and product alignment.
Even today, AskVinny maintains a weekly on-site presence with key customers. As Buchanan explains, being "the friendliest, brightest, most energetic person" in a customer’s software buying journey often tips the scale in their favour. Velocity and responsiveness, not rigid product roadmaps, define their approach.
Sales-Led Growth Backed by Data and Grit
AskVinny’s growth engine is built on high-volume, data-driven outbound sales. Their business development representative (BDR), Ryan, sends 500+ LinkedIn messages per week, tracking conversion rates meticulously from message to demo. This has helped them double their monthly closed deals compared to late last year.
The process has also proven to be a powerful product validation loop. If messaging doesn’t resonate, the team assumes the product or market fit is off - not the channel. This insight-led iteration has helped the team refine not only what they sell, but how they describe it.
To complement short-term wins from outbound sales, AskVinny recently hired a CMO to build a longer-term marketing funnel. While those results are expected to pay off in the future, outbound remains their dominant growth channel for now.
Cofounder Dynamics: Division of Labour, Shared Vision
The partnership between Rory and Johnny has been a cornerstone of AskVinny’s momentum. Though both founders share product backgrounds, they initially split responsibilities to align with investor expectations: Rory as CTO (technical) and Johnny as CEO (sales). Over time, they leaned into their strengths more intentionally, with Johnny focusing almost exclusively on sales and Rory picking up everything else.
This flexibility has been critical. In Rory’s words, “If he’s not selling, we’re not growing.” That clarity has allowed them to scale more efficiently and delegate lower-impact work effectively, with the hiring of a BDR cited as one of the company's most impactful decisions to date.
Community, Mentorship, and the Value of Founder Support
While AskVinny is remote-first, Buchanan has found tremendous value in connecting with the local startup ecosystem in Scotland, particularly through Techscaler and communities like CodeBase. He credits advisors like Andrew, a Techscaler Entrepreneur in Residence, with helping refine strategic decisions on hires and marketing spend.
Through informal mentorship and peer support, AskVinny has also landed new customers and investor connections, underscoring the power of founder-first, no-strings-attached communities in building early-stage startups.
Breaking Frames and Rewriting Expectations
Perhaps the most powerful insight from AskVinny’s journey is psychological. Building the company has fundamentally shifted the founders’ perception of what’s possible. From signing early £100/month deals to seeing large venture rounds land in the bank account, each milestone has helped “break the frame” of what they believed was achievable.
Today, they operate from a mindset of possibility. As Buchanan puts it, "This path is for anyone who wants it - not just an elite few." He remarks that even if the company were to fail, the skills, resilience, and relationships developed would make him and his team more employable than ever before.
Final Word
AskVinny’s story isn’t about a singular genius idea - it’s about relentless iteration, obsession with customer problems, and executing faster than the competition. It’s a blueprint for modern founders: start small, pivot fast, stay close to the customer, and never stop selling.
In a world of venture-backed startups chasing scale, AskVinny is proving that speed, humility, and customer-first thinking can still win.
