In this episode of the DevReady Podcast, host Anthony Sapountzis is joined by Rohan McCloskey, CEO and Founder of GoGenerosity. With a background in hospitality and a passion for community impact, Rohan shares his journey from running successful restaurants to building a purpose-driven tech startup. GoGenerosity was born out of a crisis during COVID-19, evolving from a “pay it forward” idea into a scalable e-commerce solution that enables customers to donate at checkout. Now available via a Shopify app, GoGenerosity transforms small contributions into gift cards that are distributed to charity partners—creating tangible, trackable community outcomes.
Rohan delves into how GoGenerosity strikes a delicate balance between a frictionless user experience and meaningful consumer generosity. He shares how business values, rather than transaction size, often drive donation behaviour, and why simplicity in UX design is crucial to avoiding abandoned carts. The conversation also explores how the team navigates client feedback, using a structured approach to decide which feature requests are worth pursuing. By listening carefully—but not blindly—to customers, GoGenerosity has maintained its core vision while continuing to iterate in a data-driven way.
The discussion then turns to the importance of product–market fit. Rohan reflects on lessons learned from his early startup days, when raising capital seemed like the ultimate success metric. He admits that securing funding too soon, without clear validation of the product and its audience, led to costly missteps and unnecessary complexity. Now, he champions a more measured approach: build lean, test often, and only raise capital when it’s truly needed to accelerate growth—not just to stay afloat.
Touching on investor dynamics, Rohan offers an honest look at how the wrong timing and structure can make a business uninvestable, even if the product is strong. Fortunately, GoGenerosity attracted mission-aligned, philanthropic investors who value social impact as well as financial return. This support allowed the company to remain true to its vision, without the pressure of chasing unrealistic growth metrics. Rohan underscores the need for transparency and realistic expectations when engaging with investors, and encourages founders to avoid vanity metrics that serve ego more than strategy.
Finally, Rohan speaks about the emotional toll of transitioning from a secure, profitable business to the unpredictable world of startups. He credits his own naivety for giving him the confidence to leap, but also stresses the importance of clearly identifying your customer, especially in complex marketplaces. With GoGenerosity now focused on expanding into Australia and the US—targeting over 1.2 million Shopify merchants—Rohan reflects on the power of perseverance, clarity, and customer trust. His journey is a reminder that building a meaningful business takes more than just a good idea; it demands grit, focus, and constant learning.
Topics Covered
- From hospitality to tech entrepreneurship
- Origin of GoGenerosity and the “pay it forward” model
- Designing seamless UX for generosity at checkout
- Handling customer feedback and staying product-focused
- Fundraising pitfalls and the importance of product–market fit
- Identifying the true customer in a three-sided marketplace
- Building trust through third-party verification and transparency
- International expansion via Shopify (Australia, US, UK, Canada)
- The emotional risk of leaving a successful business
- The role of naivety in taking the startup leap
Important Time Stamps
- From Restaurants to Tech: How COVID Sparked a Generosity Revolution (0:07 – 5:45)
- How GoGenerosity Balances Heart, Data, and UX (5:46 – 12:09)
- Balancing Feedback & Focus: Inside GoGenerosity’s Product Strategy (12:10 – 15:09)
- What I’d Do Differently: Lessons from a First-Time Founder (15:10 – 19:56)
- Why Raising Capital Can Kill Your Startup (19:57 – 27:43)
- The Hardest Startup Lesson? Knowing Who Your Real Customer Is The Hardest Startup Lesson? Knowing Who Your Real Customer Is (28:29 – 40:17)
