When Jack Hooper co-founded Take Command Health, it wasn't a leap off a cliff; it was more like stepping off a curb. With two infants at home and a full-time role at a major consulting firm, he built the business in the margins—working weekends and holidays testing demand, speaking with early funders, and watching usage grow before making the jump. He began with a plan to help individuals navigate insurance through a more personal, transparent model. That “TurboTax for health plans” idea eventually became the foundation for a SaaS platform that now serves over 7,000 employers and simplifies health reimbursement arrangements (HRAs) for the modern workforce.
Today, Take Command is pushing forward a shift in how health benefits are structured, not just administered. The platform goes beyond simply digitizing enrollment to moving purchasing power to employees, making coverage more personalized, portable, and transparent. Hooper’s story is a reminder for entrepreneurs that you don’t need to make a dramatic leap to start something transformative—but you do need to start.
