In this episode of Checkout, we sit down with Hamish McKay, the co-founder of OrderEditing, an innovative Shopify app that enables customers to edit their orders post-purchase. In the last 15 months the app has taken the industry by storm and now serves over 620 merchants including household names like Sheet Society, Represent Clo, and The Oodie. Hamish opens up about the weirdest purchase he’s made online, the tools that keep his business running smoothly, and the challenges of maintaining a work-life balance while expanding his company in a new country.
Spicy Shopping: Things Get a Little…Personal
When asked about his most bizarre online purchase, Hamish didn’t hesitate: “Can I say sex toys? While he didn’t go into specifics, he acknowledged the humour in his admission. “It’s either that or clothing,” he added with a laugh. While it’s a bold admission, it’s a reminder that many of us use the wonderful world wide web to purchase more personal items that we might not want to buy in person.
Represent Clo: A Brand That’s Built More Than Just Clothing
When it comes to inspiration, Hamish looks to UK streetwear brand Represent Clo, a brand known for its bold style and strong community ties. “They’ve built the coolest community surrounding a brand,” Hamish shared, expressing his admiration for the way Represent engages their audience far beyond just selling clothes. The founders of Represent host events like run clubs that bring customers together in person, creating a loyal following that interacts with the brand in real life.
“I’m going to their run club this weekend in LA,” Hamish mentioned and is always excited to experience the brand’s community-focused culture firsthand. Represent Clo’s ability to connect with customers through events and experiences is a strategy that Hamish finds both fascinating and inspiring, especially as he continues to grow his own business. It’s an important reminder for us all that great brands are more than products or services, they create meaningful connections and communities.
Organising the Chaos: HubSpot to the Rescue
Managing the rapid growth of OrderEditing requires structure, and Hamish swears by HubSpot to keep things running smoothly. “I live and die by HubSpot,” he said, explaining that he uses the tool to manage email follow-ups and track conversations. Hamish makes sure that every email has a task associated with it, ensuring that no communication falls through the cracks. “I add a task every time I send an email, even if it’s just to remind me to follow up in a few days,” he explained.
This simple but powerful platform seamlessly connects data, teams, and customers, allowing him to stay on top of everything, even as his responsibilities multiply.
If I didn’t have a way to track conversations, things would get missed—it’s all about staying on top of those touchpoints. It’s a tool worth checking out for those juggling client communications, follow-ups, and the fast-paced demands of a rapidly scaling business.
The Power of Therapy: Maybe You Should Talk to Someone
As a passionate mental health advocate, Hamish doesn’t shy away from sharing the role therapy plays in his life. His book recommendation, Maybe You Should Talk to Someone by Lori Gottlieb, is a reflection of his dedication to maintaining mental well-being while navigating the pressures of running a business.
“It’s the best book I’ve read in the last three years,” Hamish said, praising the therapist-author’s ability to blend her clients’ stories with her own personal experiences. Hamish has been attending therapy for over a year, and the book’s themes deeply resonated with him. “Therapy has been huge for keeping me aligned with what I want in life,” he shared, underscoring just how important it is to stay grounded—even when life gets hectic.
For something more light-hearted, Hamish recommended business podcast Underqualified, which is run by his friends, Sean Hark, Ed Holland, and Andre Barber. “They’ve got great guests and they tell a compelling story,” he said, highlighting the podcast’s fun, laid-back approach to business conversations. For anyone looking for a mix of good laughs and valuable business insights, this is a great listen.
Balancing Business and Life: A Founder’s Challenge in a New Country
Moving to the US to expand OrderEditing has been a big adventure for Hamish, but it’s definitely come with its challenges—especially when it comes to finding balance. “It’s been 7 a.m. to midnight, Monday to Friday,” he admitted, describing the non-stop pace he’s faced since relocating. But it’s not just the long hours that are tough. Hamish opened up about how hard it is to switch off mentally.
You’re hanging out with someone, but you’re thinking about work and tempted to check your phone.
Despite the constant demands, Hamish is working on carving out some downtime for himself, whether it’s through reading, listening to music, or just spending time with people who help him unwind. Adjusting to a new country and growing a business at the same time isn’t easy, but it’s important to always strive for a healthy work-life balance while still pushing your business forward.
Building Success with Structure and Balance
Hamish has shown that building a successful business isn’t just about rapid growth, it’s about finding a rhythm that works. His focus on maintaining structure, fostering community, and prioritising mental health demonstrates that scaling a business requires more than just hard work, it takes personal balance too. By keeping an eye on what truly matters—both in business and life—Hamish reminds us that sustainable success comes from a blend of passion and purpose and making space for yourself along the way.
The Checkout is a short snippet of our conversations.
