In this episode of The Stroke It Podcast, Jenny sits down with entrepreneur and operations leader Emily McSherry, founder and CEO of Advize—a platform helping students explore careers through short, coffee chat-style alumni interviews and AI-powered recommendations.

Emily shares how a major pivot accelerated her path: after graduating from UCLA Anderson and getting laid off when her department was cut, she went all-in on Advize at the moment she had the least to lose. She opens up about the real tradeoffs of entrepreneurship—moving, saving, living lean, and choosing long-term impact over short-term comfort.

This conversation goes beyond careers into confidence, relationships, and action. Emily explains why students hesitate to reach out, how shared connections (like being alumni) make networking easier, and why a clear, specific ask changes everything.

Jenny and Emily also talk about health, balance, values, and boundaries—why rest matters, how burnout shows up, and how structuring your time around your values can reduce anxiety and help you work smarter.

They close with practical entrepreneurship lessons: stay close to the customer, test assumptions early, and build what your customer cares about. Emily leaves listeners with a challenge: write down your dream life, step into that identity, and take one aligned action today.

If you’re a student, parent, or professional craving clarity, this episode is a reminder that clarity follows movement—and opportunity can start with one conversation.

Resources Mentioned:

Advize (free student access): students.advizehub.com
LinkedIn: Emily McSherry
Advize Newsletter

Chapters

00:00 – Common ground + connection
01:20 – Meet Emily
03:00 – Layoff → going all in
05:00 – How Advize works
08:30 – Why students don’t reach out
12:30 – Action builds confidence
15:30 – Values + the “thirds” framework
20:00 – Workplace relationships + networking
27:00 – Make a clear ask
37:30 – Entrepreneurship tradeoffs
39:00 – Build for the customer
46:20 – Visualize it, then act

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Ep 214 How One Layoff Sparked a Career Platform for Students