Winning is Fun, with Jane App Co-founder Trevor Johnston

Trevor Johnston shares the story of how Jane App was founded back in 2011. It began when a friend asked for a website for her healthcare practice, which sparked the idea of building an online booking and practice management software. The initial version was built within six weeks and launched with features that were creatively integrated into her clinic's website. Their unexpected success came from other clinics inquiring about the software after seeing it in use, leading Trevor to consider turning the project into a full-fledged business.

Throughout the podcast, Trevor emphasizes the bootstrapped nature of Jane App, which has led to a unique path compared to the usual venture-capital-fueled startup journey. The company adopted a philosophy of growing responsibly by ensuring they made more money than they spent, which allowed them to focus on quality product-market fit and customer service. This grounded approach resulted in a steady, mathematical growth curve driven by referrals from satisfied users.

Trevor discusses the power of referrals in their growth strategy, explaining how about 85% of new customers come from existing customer recommendations. He elaborates on the non-competitive nature of the healthcare practitioners that Jane serves, which fosters collaboration and encourages recommendations. This unique market dynamic has allowed Jane App to thrive through organic growth from dedicated and happy customers.

The conversation shifts towards the evolution of Jane App's organizational structure. As the team grew beyond Dunbar's number, challenges arose in communication and collaboration. Trevor reflects on the importance of establishing better separation of roles and responsibilities within the organization, particularly regarding product management and engineering, which allowed Jane to scale effectively.

Trevor shares his personal journey about transitioning from a hands-on builder to a leader who influences and guides the team's direction. He reflects on the struggle of finding fulfillment in roles that are less tangible, such as attending long meetings, and how he has learned to define success in his new role by focusing on outcomes and the broader mission of Jane App.

In this segment, Trevor touches on the technical evolution of Jane App, built initially on Ruby on Rails. He acknowledges the inherent challenges and trade-offs of maintaining a Rails monolith as the company grows, but also emphasizes the benefits it has provided in terms of rapid initial development. Looking ahead, he discusses the exploration of new technologies and the importance of diversifying Jane's tech stack as they continue to grow.