We spend 90,000 hours of our lives at work—so why do we let one bad boss ruin it all?

In this episode of TruthWorks, I sit down with Eric Charran, Microsoft Chief Architect and author of the explosive new book Have You Ever Had a Boss That…? Eric isn't just a tech veteran; he’s a screenwriter and leadership expert who has mapped out the hidden "DNA" of dysfunctional workplaces.

We dig deep into the uncomfortable reality of modern leadership. Eric reveals the 9 Boss Archetypes that secretly govern your office (are you working for a "Firefighter" or an "Attack Sub"?), and we debate the difference between a "hard" culture and a "toxic" one.

As the former CHRO of Netflix, I thought I had seen it all—but Eric’s psychological breakdown of why bad bosses exist (and why we keep hiring them) completely shifted my perspective. If you feel stuck, undervalued, or burnt out, this conversation is the manual you didn't know you needed.

TOPICS DISCUSSED:

• The "Attack Sub": How to spot the boss who sinks you from the shadows.
• Netflix vs. Microsoft: Comparing the "Keeper Test" to Eric's "Dysfunctional Archetypes."
• The "Firefighter" Trap: Why your boss creates crises just to save the day.
• Managing Up: The exact scripts to use when your leader is the problem.
• The AI Boss: Will algorithms eventually replace middle management?

Jeff Seibert — CEO & Co-Founder of Digits, and the product builder behind Crashlytics (acquired by Twitter, used by nearly every major mobile app) — joins Jessica Neal on Truth Works for an honest breakdown of what it really takes to build world-changing products.

From early startup chaos to shipping tools that feel "invisible" and magical, Jeff shares the frameworks that shaped his thinking — and why finance needs an AI-native reinvention.

In this episode, we explore:
• The origin story of Crashlytics & lessons from hyper-scale
• The transition from Fabric → Digits and designing for clarity
• Why accounting is broken — and what AI can fix
• Product simplicity vs. complexity: the discipline behind it
• Leadership under pressure, momentum, burnout, and team trust
• How founders should think about automation, decision-making & AI tools
• What he wishes he knew earlier

A rare look inside the mind of a founder who repeatedly builds systems that billions rely on — and why his next bet might reshape how business finances run.

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.