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 Governors University, to explore how a former Amazon leader found the most meaningful fit of his career — and what it cost him to get there. Scott opens up about a brutal leadership feedback experience at Amazon that nearly broke his confidence, how that humbling moment became the foundation for his growth as a leader, and why attending a single WGU commencement convinced him this was the mission he'd been preparing for his entire career. We cover what Amazon's culture of customer obsession taught him, why he now hires for motivation over expertise, and what the future of education looks like in an AI-driven world.

Key Takeaways:

• Brutal feedback, delivered well, can be the most important catalyst in a leader's development
• The right fit isn't just about the role — it's about the mission, the context, and the moment
• Customer obsession and process discipline are not opposites; they are multipliers of each other
• Startup CEOs often centralize decision-making in ways that prevent scale — great leaders learn to delegate authority and accountability together
• Hiring for expertise without weighting motivation and people skills produces only a fraction of the intended impact
• Potential, reasoning ability, and beginner's mind often matter more than prior experience at scale
• Executive search and hiring criteria that overweight past experience can systematically exclude the best candidates
• Tech fluency — particularly AI fluency — is becoming table stakes regardless of industry or career path
• The job-to-be-done framework applies to education decisions just as powerfully as to product strategy
• Serving others is not a drain on a leader's energy — it is the fuel

Connect with Jason: https://www.linkedin.com/in/jasonbaumgarten/
Email the show here: fithappens.fm

• (00:00) - Introduction & episode theme
• (00:33) - Scott's welcome
• (00:44) - First job: bookkeeper at 14
• (01:15) - Early career superpower: rapid learning
• (02:26) - Knowing the job to be done
• (03:07) - From Sterling Commerce to Amazon
• (05:00) - The leadership feedback program at Amazon
• (07:00) - Losing confidence — and rebuilding
• (07:52) - What brutal feedback taught Scott
• (08:30) - Seeking the right context to grow
• (10:10) - Becoming a steward, not a star
• (11:55) - Before WGU entered the picture
• (12:20) - Why a commencement changed everything
• (15:00) - Talent is universal — WGU's mission
• (16:00) - WGU explained for the uninitiated
• (16:12) - Competency-based education at scale
• (18:00) - 70,000 graduates a year — and counting
• (19:25) - Unlocking people's full potential
• (20:02) - The graduate counter on the wall
• (20:42) - Amazon's customer obsession lesson
• (21:30) - Student obsession as organizational north star
• (22:45) - Process as a scale enabler, not bureaucracy
• (24:11) - Startup CEOs and process problems
• (24:35) - Delegating decision-making authority
• (27:00) - Autonomy paired with accountability
• (28:10) - Flow states and leadership superpowers
• (28:53) - When Scott finds his flow
• (30:30) - Envisioning future state — the whiteboard moment
• (32:36) - When the leader must evolve with the org
• (33:28) - Board expectations: 40–50% on innovation
• (34:52) - Building the right team
• (35:31) - Shifting from expertise to motivation
• (38:40) - Experience vs. potential in hiring
• (39:12) - Why Scott himself wouldn't have passed traditional criteria
• (41:04) - Potential, beginner's mind, and fit
• (42:13) - What Scott chose to bring from Amazon
• (44:23) - Advice for parents on education and AI
• (44:51) - Job-to-be-done framework for education
• (48:00) - AI fluency as the new table stakes
• (49:15) - Speed round begins
• (49:28) - Leadership advice Scott thinks is actually harmful
• (50:33) - A skill he's changed his mind about
• (51:24) - The biggest surprise of being a CEO
• (51:58) - Book & TV recommendations
• (52:46) - Scott's go-to zone-out hobby
• (53:10) - Closing reflections

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 important sentence any executive can write: "I was hired to do X, as measured by Y, while avoiding Z, and by building systems and teams that make it repeatable." Whether you're stepping into a new C-suite role or six months into one, mandate clarity is the difference between performance and misalignment. I walk through a practical framework covering how to define your real mandate (X), understand how success will be judged (Y), navigate organizational third rails (Z), and build systems that make results durable — not dependent on your personal heroics.

Key Takeaways:

1. Most executive failures are a fit problem, not a capability problem.
2. The X — your true mandate — is not a job description; it's the specific problem you were hired to solve, right now.
3. The Y — your scorecard — must be explicitly aligned with your boss or board, not assumed.
4. Distinguish between input metrics you control and output metrics that may be beyond your reach.
5. Every role has third rails (Z) — unwritten rules that can derail you if you don't surface them early.
6. The Kodak story: perceived third rails are often not third rails at all. Probe before assuming.
7. Building a system — not just delivering results — is what makes leadership impact durable.
8. In your first 30 days, prioritize mandate alignment over proving yourself.
9. Ask your hiring authority: "If you could only pick one outcome for me this year, what is it?"
10. Circulate the mandate with your team — if they can't articulate it, alignment hasn't happened yet.

Connect with Jason: https://www.linkedin.com/in/jasonbaumgarten/
Email the show here: fithappens.fm

• (00:00) - Introduction & The Core Question
• (00:23) - Why Executives Solve the Wrong Problem
• (01:11) - Transformation Leader vs. Caretaker
• (01:41) - Performance Is a Fit Problem
• (02:10) - The One Sentence Framework
• (02:31) - X: Defining Your Real Mandate
• (03:35) - Y: How Will Success Be Judged?
• (04:14) - Hard Metrics vs. Soft Metrics
• (05:00) - Input vs. Output Metrics
• (06:33) - The Seattle Office Story
• (08:05) - Z: Third Rails & What Can Go Wrong
• (09:33) - The Kodak Leadership Story
• (10:30) - Probing Assumed Third Rails
• (10:54) - Building the System (Repeat)
• (12:03) - The First 30 Days Approach
• (12:16) - The Mandate Conversation Questions
• (13:16) - Validating With Broader Stakeholders
• (14:07) - Building Systems That Deliver
• (15:01) - Common Ways Executives Get This Wrong
• (15:53) - Your Assignment: Write the Sentence
• (16:09) - Where Fit Happens

She left a dream job at peak success — because she finally discovered what true alignment feels like.

In this episode of Fit Happens, Jason Baumgarten sits down with Kara Nortman, managing partner of Monarch Collective — the only investment platform exclusively focused on women's sports. Kara's career spans Morgan Stanley, IAC, Battery Ventures, Upfront Ventures, and co-founding Angel City Football Club alongside Natalie Portman. She talks candidly about what it took to leave a role she was thriving in to pursue a fit she didn't know she needed, the role of coaching and personality frameworks in her growth, and what she's learned about assessing people across decades of investing.

Key Takeaways:

1. True alignment feels different from just being good at your job — and recognizing that gap is a gift.
2. Flow isn't something that arrives; it requires deliberately building the right container of habits and environment.
3. Women often take longer than men to recognize and fully own their natural strengths — and this has real career costs.
4. Using tools like the Enneagram and Human Design can help leaders identify patterns and lead more self-aware teams.
5. The victim, villain, hero framework is a powerful lens for reframing how you respond to difficult circumstances at work.
6. Job crafting works: Kara's decision to write a venture blog in 2004 directly led to her role at IAC.
7. The best hires often have broken resumes and something to prove — perfection on paper can be a red flag.
8. Interviewing is no better than a coin toss even for skilled practitioners — but starts improving when you define what you actually need.
9. Reference calls work best when referencers feel they're helping you succeed with the person, not judging whether to hire them.
10. Partnering well — knowing what you're great at and building complementary teams around it — is the long-term driver of enduring companies.

Connect with Jason: https://www.linkedin.com/in/jasonbaumgarten/
Email the show here: fithappens.fm

• (00:00) - Introduction
• (00:43) - First job: Ben & Jerry's
• (02:16) - Defining strengths early in career
• (03:18) - Kara's career overview
• (05:28) - The Women's World Cup moment
• (08:17) - Leaving a dream job for a greater fit
• (11:13) - Flow: building the right container
• (13:30) - Nobody is always in flow
• (14:22) - The jobs that didn't feel right
• (15:55) - Paths to Power & the mailroom principle
• (18:01) - Victim, villain, hero framework
• (19:30) - Enneagram & personality profiling tools
• (21:00) - Blog as job crafting: Battery to IAC
• (22:30) - Incubating Tinder at CitySearch
• (23:30) - Side hustles and what's next
• (25:00) - The loneliness epidemic
• (27:02) - Staying connected outside work identity
• (29:04) - What makes a good assessor of people
• (33:54) - Are you a good picker?
• (34:42) - Why skilled interviewers are still coin tosses
• (35:47) - Blemishes, broken resumes & what they signal
• (37:58) - How to reference the right way
• (39:14) - AI, careers & parenting the next generation
• (43:57) - Rapid fire: five questions
• (49:26) - Sign-off