Fit Happens: The Executive Search Podcast

No One Works Here: What AI Actually Changes About Work

MIT built a job title from scratch because Paul Cheek didn't fit any that existed. Now he's ranking the S&P 500 on AI maturity, and the results may surprise you. We get i

Why Nobody Tells the CEO the Truth

Seventy-three seconds after launch, the warning that could have stopped the Challenger disaster had already been softened beyond recognition. In this solo episode, I brea

He Left Silicon Valley to Run a Retreat in the Andes

He traded Silicon Valley for the Andes and built a life around a completely different definition of leadership. In this episode, I talk with Terry Cumes, CEO of Wilkatika

Why Six Months Can Turn You Into a Better CEO Candidate

Boards rarely hire the most capable person. They hire the one who feels the safest to defend. In this solo episode, Jason Baumgarten breaks down signaling theory and wha

Why Krishna Iyer Left Big Tech for a 170-Year-Old Railroad

He spent two decades at the frontier of tech. Then he chose a 177-year-old railroad instead. In this episode, I talk with Krishna Iyer, head of software engineering at B

The 100 Day Plan Is a Lie. Here's What Actually Works.

A new CEO's hundred day plan sounds smart. The research says it's mostly fiction. In this solo episode, Jason Baumgarten traces the hundred day myth back to its real ori

Group Intelligence Beats Individual Genius with Lexy Franklin

Loneliness and bad fit can feel identical, but they are not the same thing at all. Lexy Franklin, founder of Sidebar and former Facebook product leader behind Messenger K

Don't Cast a Halo: Why Great Leaders Get Blamed for Bad Luck

One stock price swing can turn the same leader from visionary genius to reckless failure overnight. In this solo episode, I break down the halo effect, the century-old ps

Why Your Best Salesperson Makes Your Worst Manager

Your best salesperson just got promoted to manager. Here's why that's often a mistake. In this solo episode, Jason Baumgarten unpacks the Peter Principle, the half-centu

Why Busy Leaders Still Don't Control Their Own Calendar

If time is your most valuable asset, who's actually deciding how yours gets spent? In this solo episode, I unpack a paradox I see constantly in the leaders I work with:

Why the Obvious CEO Hire Is So Often the Wrong One

What if the same leader, running the same playbook, could fail in one place and win big in another? That's the question at the heart of my conversation with Jim Citrin,

Beyond Employee Engagement: How Mattering Transforms Leadership and Executive Search

What if the thing quietly undermining your team's performance isn't strategy, compensation, or culture decks, but whether people feel like they matter? Jennifer Wallace

The Boardroom Is Broken: How AI Changes Executive Leadership Forever

The boardroom is the last line of defense for AI governance — and most directors aren't ready. Steven Wolfe Pereira has spent 30 years at the intersection of technology,

Your Schedule Is Your Job — How AI Affects Job Fit

What if the job you have today quietly becomes the job you never agreed to take? In this solo episode, Jason Baumgarten breaks down one of the most underestimated risks

The Spikiness Principle: What Executive Search Gets Wrong About Talent and Fit

The investors closest to the best founders have a front-row seat to what great fit really looks like. In this episode of Fit Happens, I sit down with Laela Sturdy, Manag

Is Your Job Worth It? The Hidden Cost of Being in the Wrong Role Too Long

You have roughly 4,000 weeks. Are you spending them on work that actually deserves them? In this solo episode, Jason Baumgarten — senior partner and executive search spe

From Google to the Grill: Dan Gertsacov on Career Fit and Leading Big Green Egg

Dan Gertsacov, CEO of Big Green Egg, has built a career by saying no to money and yes to fit — four times over. In this episode, we dig into his non-linear path from soci

CEO Burnout Is Destroying Your Judgment — Here's How to Stop It

Most executives aren't failing loudly — they're quietly eroding from the inside out. Nearly a quarter of CEOs report feeling burned out daily. But burnout isn't just a p

How Scott Pulsipher Found His Fit as CEO of a 200,000-Student University

What does it really take to find the role you were built for — and lead it at scale? In this episode of Fit Happens, I sit down with Scott Pulsipher, CEO of Western Gove

The One Sentence Every Executive Should Write Before Day One

Most executives fail not because they lack talent — but because they're solving the wrong problem. In this solo episode of Fit Happens, I'm breaking down the single most