Building Culture while Scaling Startups with Josh Domingues, Founder of MedWallet & FlashFood

In this episode, Josh Domingues shares the journey from hockey and finance to building Flashfood and launching MedWallet, offering an honest look at startup leadership, hiring, and building culture while scaling fast. The conversation explores how intuition, transparency, and human connection shape both product decisions and team dynamics, especially during moments of crisis and rapid growth. Josh also challenges traditional workplace practices like job descriptions and performance reviews while sharing his vision for the future of healthcare powered by AI.

00:00 - Introduction
04:22 - From Hockey Player to Finance to Consulting to Startups
09:50 - First Startup Failure
10:43 - Flashfood Idea: Solving Food Waste
11:45 - Scaling Flashfood & Raising $25M 
17:23 - Founder Intuition & Being Early to Big Trends
20:23 - Building Culture & Motivating Frontline Workers
21:45 - COVID Crisis
24:05 - Leadership Lessons From Supporting Employees
28:00 - Why Companies Are Teams, Not Families
30:54 - Flashfood Culture, Systems & Rituals
32:55 - Why Performance Reviews Don’t Work
35:16 - How to Grow Fast in a Startup (Ignore Job Descriptions)
38:10 - Leadership Style: Strong Opinions Loosely Held
40:10 - Psychological Safety & Firing a Toxic Manager
43:52 - Spotting Bad Teammates (Sports → Business)
46:51 - MedWallet Origin Story
49:19 - Healthcare System Problems & Personal Experiences
49:50 - MedWallet Product Explained
52:20 - AI + Healthcare Future
53:30 - Final Advice: Authenticity in the AI Era