This episode is for anyone who’s thought about making a “this could either make me a multimillionaire or blow up my life” career move. Kayleigh walks through journey from Germany at Amazon to Bay Area tech startup to stability as an executive in Nashville.

She shares the chaos, the lessons learned the hard way, and the clarity that only comes after things fall apart. She dives into risk, stability, self-protection, and why success looks very different once you stop chasing titles and start building a sustainable, fulfilling life.

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2025 broke everything Sarah thought she was building. In this episode, she shares the reality of career and her relationship status - and the emotional aftermath that followed.

This isn’t a highlight reel. It’s an honest conversation about identity loss, rebuilding confidence, and finding meaning again when everything feels uncertain. Sarah also talks through the tools that helped her move forward and what she’s focusing on next as she starts over.

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For the first time, Sarah interviews her sister Amanda, known as “Robby,” for a raw conversation about ambition, risk, and redefining success. As a solo female General Partner in venture capital, Amanda defied the odds by leaving her job as a Partner at an established venture capital fund and raising $22 million for her own fund, Modern Technical Fund (MTF), during one of the most difficult fundraising environments.

In this episode, she shares the realities behind the headlines: the challenges, the internal recalibrations, and what it really takes to build something independently in a cutthroat, highly competitive industry. A must-listen for founders, investors, and anyone questioning whether they want to build something of their own.

Hosted on Acast. See acast.com/privacy for more information.