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In this episode of the DevReady Podcast, Anthony Sapountzis, CTO and Co-Founder of Aerion Technologies and DevReady.Ai, speaks with Jay Mon, Founder of City Swapp, Product Design Lead at Exceed Business Intelligence, and Founder and Lead Designer at Innomad Digital Solutions. Jay shares how her journey from broadcast media into product design and startup building was shaped by solving real-world problems, navigating the challenges of software development and learning how to build digital products more strategically. From launching her first travel-focused startup to developing City Swapp for remote workers, she reflects on the technical, financial and product lessons that changed the way she approaches startups, MVPs, marketplace growth and product validation.
Jay’s first startup began with a simple problem she noticed while hosting on Airbnb. A guest needed somewhere to leave their luggage after checkout, and Jay saw an opportunity to connect travellers with nearby convenience stores that had unused storage space. The idea evolved into a digital product, but with no technical background, Jay and her co-founder found themselves navigating outsourced development teams, rising costs, delays and difficult technical decisions. The experience showed her how important it is for founders to understand enough about technology to ask the right questions, assess advice and stay involved in the development process.
The startup eventually reached beta testing, but COVID disrupted the travel market and forced the project to pause. During that time, the technology became outdated, maintenance stopped and the cost of rebuilding became difficult to justify. Jay and Anthony discuss how this highlighted a broader lesson for founders: software requires ongoing investment in infrastructure, updates, documentation, maintenance and technical planning. They also explore how poorly structured code and short-term development decisions can create expensive rescue projects later, particularly when an MVP is built without considering the longer-term product vision.
Those experiences directly influenced the way Jay approached City Swapp, a house-swapping and subleasing platform designed for remote workers. This time, she chose a leaner web-based model, worked with an experienced full-stack developer and selected cloud services that could scale alongside usage. Her product design experience also gave her greater ownership over the user experience, interface and technical conversations. Jay explains how staying close to the engineering process, retaining access to repositories and logins, and asking better questions helped her build with more control and fewer unnecessary costs.
City Swapp also taught Jay a different set of lessons about marketplace businesses. She initially launched the platform with a subscription model, but quickly discovered the familiar marketplace challenge of balancing supply and demand. With too few listings, users had little reason to pay, prompting her to rethink monetisation and focus first on growing supply, validating demand and learning from real users. She reflects on how founder conviction can sometimes become rigidity, and why listening to feedback, validating earlier and building smaller can help founders make better product decisions.
Looking ahead, Jay is repositioning City Swapp around free listings and user growth, supported by a manual KYC and verification process designed to create a safer subleasing experience for remote workers. The immediate priority is to build a strong supply of listings, grow the community and gather meaningful feedback before introducing monetisation. Throughout the conversation, Jay’s experience reinforces a practical message for startup founders: understand the problem deeply, stay flexible about the solution, plan beyond the MVP and treat every stage of product development as an opportunity to learn.
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