Medici

Diaz started Medici around 2016 after recognizing a critical gap in how companies manage distributed workforces. The pandemic accelerated this pain point—how do you maintain operational rigor and truly understand employee satisfaction when your team is spread across locations? Unlike traditional annual surveys, Medici aimed to provide real-time, objective insights into how employees work, their preferences, and their performance.

The founder bootstrapped the company with over $100,000 of his own money, spending heavily on hosting, contractors, and design work. Rather than chase fast growth, Diaz deliberately moved slowly, reinvesting carefully and turning down funding three times. He wanted to achieve product-market fit before taking external capital. Two years into the journey, the team paused to completely redesign their go-to-market strategy and target audience based on customer feedback.

The first customer came from family—Diaz's mother used the solution in her consulting company, which had a distributed workforce. The second customer was a friend running for mayor of Seattle who needed workforce management for his campaign. Growth remained gradual, and by year six, the company had just three active pilots. Each pilot customer paid between $5,000 and $10,000 during the typical three-month beta period, translating to roughly $2,000 per month if they continued past the pilot phase.

The deliberate, bootstrapped approach allowed Diaz to stay independent and avoid board pressure, but it also meant slow traction. By six years in, having only three pilots felt like a plateau. The founder continued working full-time at Zillow running campaign strategy while building Medici nights and weekends. This split focus likely constrained growth, though it provided financial stability. The core product—using 18 different attributes to predict employee inclusion, on-time delivery, and sentiment—resonated with early customers, but scaling beyond pilots proved challenging.

With two full-time team members (Diaz as product lead and a co-founder who is an aeronautical engineer), the company is exploring new growth vectors: white-labeling to complementary partners and targeting niche communities like digital nomads. Diaz was actively exploring bringing on a COO and planning to eventually transition to full-time work at Medici. While not chasing a "hockey stick," he aims to prove Medici can become a sustainable, profitable business serving distributed teams.