Never Ready, Never Alone: Suneel Gupta on Playing the Game of Now

What if “I’m not ready” is the biggest lie holding you back? In this episode of Truth Works, Jessica Neal sits down with Suneel Gupta — once literally the “poster child for failure” in The New York Times — to unpack how failure, exhaustion, and uncertainty can become fuel for a more courageous, energized life.

Suneel shares how going from failed founder and Groupon’s hyper-growth implosion to successful health-tech exit, Harvard faculty, and Amazon Prime host wasn’t about having a perfect plan — it was about playing what he calls the game of now instead of the game of “someday.” He breaks down why none of the extraordinary people he’s studied ever felt “ready,” how they acted anyway, and how they managed their energy (not just their time) to stay in the game.

You’ll hear:

• Why “I’m not ready” quietly kills careers and ideas
• How being the face of failure opened doors to Oscar winners, founders & leaders
• The “game of now” vs. the “game of someday” — and how to start today
• Why courage is not the absence of fear (and why fear is required)
• Emotional runway vs. financial runway for founders and teams
• Rhythmic renewal: the 55:5 model for building breaks into every day
• Why vacations don’t fix burnout — and what actually does
• “Rest is not a reward, it’s a resource” — a new mantra for high performers
• The simplest definition of happiness: never worry alone

If you’ve ever felt behind, burned out, or paralyzed waiting for the perfect moment, this conversation will give you language, tools, and a different way to move forward — one small action at a time.