Career Fit Beyond VC: Kara Nortman's Path to Women's Sports Leadership

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