Waverly Deutsch doesn’t just coach entrepreneurs—she translates English to English, reframes stories with strategy, and helps even the most logic-trained professionals tap into their conviction. In this three-part series, we walk through her unusual path from consulting to Chicago Booth to founding WyseHeart, her pitch strategy firm.

Each episode reveals a new dimension of her journey: the personal (Part 1), the academic and instructional (Part 2), and the entrepreneurial, including her bold take on how to co-exist with AI (Part 3). Across every chapter, Waverly models what it means to coach with both love and logic—bringing clear frameworks to messy human dreams.

Key Highlights of Our Interview:

What Investors Actually Want

“Good ideas are everywhere. I invest in people who know how to execute.”

Lessons from both sides of the table: raising capital and writing checks.

You Are Not Your Company

“When a startup fails, it doesn’t mean you failed.”

Helping founders detach identity from outcome.

The Metrics That Really Matter

“Sometimes traction isn’t revenue—it’s retention, referrals, or even the right kind of no.”

How she helps founders track the right signals.

Managing the Urge to Please

“Women, especially, are taught to be agreeable. That doesn’t work in fundraising.”

Teaching confidence without arrogance.

Love and Logic, Always

“Lead with empathy. Decide with data. And know which one to use when.”

Her golden rule for founders—and herself.

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Host: Vince Chan | Guest: Waverly Deutsch

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#427 Waverly Deutsch: Love and Logic—Building Businesses That Actually Work—Part Three