The traditional path isn’t the only path. Sarah and Kayleigh unpack the idea of “The Third Door," the unconventional way people often break into careers, opportunities, and rooms they weren’t supposed to be in. Through stories from their own careers and lives, they share how thinking differently, taking risks, and pursuing non-traditional routes opened doors they didn’t even know existed. Because sometimes the side door is the one that actually works.

For more:

• Follow Kayleigh on Instagram
• Follow Sarah on Instagram

Produced by Peoples Media

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

So much has changed since we first hit record on this podcast. In this episode, Sarah and Kayleigh take a moment to reintroduce themselves, sharing where they’re living now, what they’re working on, and how their careers and lives have evolved since the podcast began. From unexpected pivots to new chapters, this conversation is an honest update on where things stand today. Consider this the reset before what’s next.

For more:

• Follow Kayleigh on Instagram
• Follow Sarah on Instagram

Produced by Peoples Media

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

Everything is getting more expensive, but most people don’t feel like their income is keeping up. You can cut your costs, or you can find ways to make more money. With only 29% of millennials engaged at work, many people feel stuck in jobs that don’t pay enough and aren’t sure how to change it. Sarah and Kayleigh share how they’re thinking about earning more in 2026, from new income opportunities to unconventional career strategies that go beyond the traditional path.

Produced by Peoples Media

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

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

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.

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

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.

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

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.

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