Gusto – Entrepreneurial Journeys
Challenge
Gusto wanted to understand the lived experiences of people in the first few years of building a small to medium sized business. The goal was to uncover the motivations, challenges, and behaviors that define the modern entrepreneur.
Approach:
We designed a study that went beyond surface-level insights or startup myths. Instead, we captured the full texture of what it means to build a business from scratch—not just the practical steps, but the emotional, cultural, and systemic undercurrents that shape entrepreneurial identity. The study ran in iterative waves, blending short and long interviews, with recruitment, data collection, and analysis happening in parallel. This allowed us to scale up the dataset while maintaining rich qualitative depth and refine themes in real-time.
Interesting Insight:
No matter how they started their journey, every entrepreneur will hit a turning point: the tension between “doing the work” and “running the business.” Overcoming this moment develops a particular skill set that reshapes how they see opportunity. We call this the moment they put on their “entrepreneurial glasses” – a new lens to planning where building is not just for survival, but strategy, creativity, and momentum. Many are eager to do it again, only this time, better.
Impact:
We built an extensible, foundational data set for internal, cross-team innovation work, and a suite of applied insights. The insights resulted in new segmentation, informed product development for new and returning customers, and identified real spokespeople for better marketing and outreach.
Related Work:
This was not our first time working in the entrepreneurial sector. We have also previously worked on several projects including burnout among business leaders and toxic workplace cultures. Our work went on to inform and inspire two books and the development of an assessment used in leadership training.