Oliver Garside: The Art of Building for the Forgotten Market

In this episode of The Wisdom Of... Show, host Simon Bowen speaks with Oliver Garside, Co-Founder and Director of Rounded App, a beautifully simple accounting and invoicing application built specifically for freelancers and sole traders. Oliver shares the profound insights gained from nearly a decade of serving an underserved market, achieving an extraordinary 99% customer satisfaction rating, and discovering the infinite creativity of the Australian freelance economy. Learn about first principles thinking, customer-centric design philosophy, and the wisdom of building for humans rather than systems.

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Episode Breakdown

00:00 Introduction and Oliver's journey from corporate redundancy to co-founding Rounded

05:30 The origin story: Meeting technical founders who built beautiful software but needed market strategy

12:45 First principles thinking: Building for end users, not their accountants

18:20 The philosophy behind "beautifully simple accounting" and challenging industry conventions

25:40 Market diversity: From sheep ultrasound specialists to yacht sail makers

32:15 Achieving 99% customer satisfaction through customer-centric design

38:50 Co-founder dynamics and navigating business tensions with ego aside

44:20 The freelance economy wisdom: Diversity of capability and confidence gaps

51:10 Mission beyond product: Stewardship of the freelancer community

57:30 Scaling challenges: Maintaining core genius while growing the business

About Oliver Garside

Oliver Garside is the Co-Founder and Director of Rounded, a beautifully simple accounting and invoicing app built specifically for freelancers and sole traders. With a passion for empowering self-employed professionals, Oliver has played a pivotal role in creating a platform that takes the stress out of managing finances, making it easier for creatives, consultants, and contractors to focus on doing what they love.

With a background in marketing, customer experience, and startup growth, Oliver brings a user-first approach to everything he does. Under his leadership, Rounded has become one of Australia's most loved tools for solo business owners, achieving an exceptional 99% customer satisfaction rating through its commitment to simplicity, efficiency, and human-centric design.

Connect with Oliver Garside: 

LinkedIn: https://www.linkedin.com/in/olivergarside/

Website: https://rounded.io

Instagram: https://www.instagram.com/roundedapp/

About Simon Bowen

Simon has spent over two decades working with influential leaders across complex industries. His focus is on elevating thinking in organizations, recognizing that success is directly proportional to the quality of thinking and ideas within a business. Simon leads the renaissance of thinking through his work with global leaders and organizations.

Connect with Simon

LinkedIn: https://www.linkedin.com/in/simonbowen-mm/

Instagram: https://www.instagram.com/officialsimonbowen/

Website: https://thesimonbowen.com/

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