Critical Moments

Conversations with leaders about one specific moment in their career that changed everything. I talk with founders, CEOs, and leaders about the decisions that defined them; the hard calls, the lessons, the things they wish they knew.

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What Liana Douillet Guzman Couldn't Unsee

Folx Health CEO Liana Douillet Guzman shares how the SVB collapse revealed deeper business truths and tested her leadership during crisis.

Jacob Ross on Trusting Yourself and Building the Business You Can See

PebblePost CEO Jacob Ross shares how trusting yourself leads to better strategic decisions and the difference between good and great opportunities.

Sue Heilbronner on Losing a Role, Choosing Herself, and Selling Without Selling

Sue Heilbronner shares how losing her job became the catalyst for building a successful coaching practice without traditional selling.

When the World Stopped: Chris Grosso on Leading an IRL Business Through Covid

Intersection CEO Chris Grosso shares how he led his out-of-home advertising company through a 75% revenue collapse during COVID.

Tapas for One: How Clara Ma Turned Burnout into a Booming Business

Clara Ma shares how walking away from startup burnout accidentally sparked Ask a Chief of Staff, a thriving coaching business.

Perfectly Enough: Jaclyn Fu's Leap from Product Marketer to Purpose-Driven Founder

Pepper founder Jaclyn Fu shares her leap from product marketer to purpose-driven founder and building a bootstrapped business.

You Need a Soulmate, Not Just a Cofounder: Paul Canetti on Building MAZ

MAZ founder Paul Canetti shares why you need a soulmate, not just a cofounder, and how a cold LinkedIn message changed everything.

Julie Samuels of Tech:NYC: The Power of Coming Back

Tech:NYC CEO Julie Samuels shares her journey of returning to lead the organization she founded and navigating crisis as a leader.

99% Blocked — and Andrew Racine Had No Idea

Andrew Racine discovered 99% heart blockage with no symptoms. He shares lessons on stress, health, and mortality for high-achievers.

Your Career Is Not a Suicide Pact — with Chris Gannett

Entertainment executive Chris Gannett rethinks ambition after missing life milestones and losing his father.

Keep Calm and Call John McCarthy, Tech's Mr. Wolf

Fractional CFO John McCarthy shares how he guides panicked CEOs through financial emergencies and cash crises.

We Had to Bet the Company — Nick Francis on Reinventing Help Scout

Help Scout CEO Nick Francis shares how he bet the company by killing a decade-old pricing model to align values with business reality.

Untethered: Nick Gould on Rediscovering Purpose After the Exit

Nick Gould shares the five months of uncertainty after selling the company that defined him and rediscovering purpose.

The Knockout Punch: How Kara Berklich Weber Turned Crisis into Opportunity

First-time president Kara Berklich Weber led through pandemic disruption to a successful exit with Dapper Labs.

David Siegel on Surviving the Impossible: The Day Meetup Went Online

Meetup CEO David Siegel shares how he pivoted the company's entire mission online in 48 hours when COVID hit.