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.

_______________________________

Connect with us:

Host: Vince Chan | Guest: Waverly Deutsch

--Chief Change Officer--

Change Ambitiously. Outgrow Yourself.

Open a World of Expansive Human Intelligence

for Transformation Gurus, Black Sheep,

Unsung Visionaries & Bold Hearts.

EdTech Leadership Awards 2025 Finalist.

20 Million+ All-Time Downloads.

80+ Countries Reached Daily.

Global Top 1% Podcast.

Top 5 US Business.

Top 1 US Careers.

>>>200,000+ are outgrowing. Act Today.<<<

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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:

From Book Smarts to Business Savvy

“Entrepreneurship is a process—whether you’re 20 or 50.”

At Booth, Waverly coached a wildly diverse mix: undergrads with unchecked imagination, MBAs with ideas but risk aversion, and execs who played it too safe. Her role? Adjusting the dials between wild dreams and grounded strategy—always pushing people to think just a little bigger (or a little sharper).

Love for the Logical Skeptics

“If you, the entrepreneur, don’t believe you’re building a $50M company, why should the investor?”

Her job wasn’t to sugarcoat—it was to stretch minds. She shares how she helped overly rational MBAs move from “safe” ideas to bold, fundable visions—and overly optimistic young founders get real about execution. Her coaching mantra? Meet them where they are—and nudge from there.

The Muffin That Grew a Billion Dollars

“This could be the Betty Crocker of the 21st century.”

A standout case: Simple Mills founder Caitlin Smith. What began as a gluten-free side hustle turned into a billion-dollar brand—thanks in part to Waverly’s nudge to imagine bigger. It’s a masterclass in how one coach reframed a story and sparked a scale-worthy vision.

Coaching in the Wild

“I’m an English-to-English translator.”

Post-Booth, Waverly now works with a broader crowd: from seasoned pros to small business owners without MBAs. Her key lesson? Listen deeply, strip away jargon, and tailor advice to meet people where they are—because real coaching starts with trust, not templates.

Can AI Be Your Coach? Nope.

“If marriage is ‘til death do us part, investment is ‘til exit do us part.”

Waverly doesn’t see AI as competition—yet. A pitch deck might be AI-generated, but building investor trust, interpreting nuance, and navigating founder doubt? That’s strictly human territory. Coaching is about relationships, not just logic—and for that, love still wins.

_______________________________

Connect with us:

Host: Vince Chan | Guest: Waverly Deutsch

--Chief Change Officer--

Change Ambitiously. Outgrow Yourself.

Open a World of Expansive Human Intelligence

for Transformation Gurus, Black Sheep,

Unsung Visionaries & Bold Hearts.

EdTech Leadership Awards 2025 Finalist.

20 Million+ All-Time Downloads.

80+ Countries Reached Daily.

Global Top 1% Podcast.

Top 5 US Business.

Top 1 US Careers.

>>>200,000+ are outgrowing. Act Today.<<<

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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:

The Computer Scientist Who Loved Shakespeare

“I’ve always had a foot in both worlds—logic and emotion, code and creativity.”

How Waverly’s dual passions for computer science and theatre shaped her approach to business.

The Pivot Into Entrepreneurship

“I didn’t want to write code anymore. I wanted to solve problems worth solving.”

Why she left tech to help build a startup—and never looked back.

Real Lessons, Not Just Case Studies

“Harvard cases are great, but I wanted to teach with my own stories.”

How she built her curriculum at Booth from lived experience.

Founders Aren’t Born

“They’re shaped by experience, community, and the right mindset.”

What makes someone capable of starting—and sustaining—a business.

Emotion Belongs in the Room

“Business is about people. If you’re not teaching that, you’re missing the point.”

Why she teaches soft skills just as seriously as finance and ops.

_______________________________

Connect with us:

Host: Vince Chan | Guest: Waverly Deutsch

--Chief Change Officer--

Change Ambitiously. Outgrow Yourself.

Open a World of Expansive Human Intelligence

for Transformation Gurus, Black Sheep,

Unsung Visionaries & Bold Hearts.

EdTech Leadership Awards 2025 Finalist.

20 Million+ All-Time Downloads.

80+ Countries Reached Daily.

Global Top 1% Podcast.

Top 5 US Business.

Top 1 US Careers.

>>>200,000+ are outgrowing. Act Today.<<<

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In Part Two, Brian opens up about what it really cost him to tell the truth inside a political system built on avoidance. From surviving misinformation attacks to refusing to play nice for the sake of power, he reflects on the risks and responsibilities that come with using your platform when it might backfire. We also hear how he rebuilt after the storm—why starting over matters, and what he’s doing differently this time around.

Key Highlights of Our Interview:

The Price of Authenticity

“I didn’t lose because I lacked support—I lost because I refused to lie.”

What really happened during his run for lieutenant governor.

Party Loyalty vs. Personal Truth

“I wasn’t going to smile and play along just to move up.”

When doing the right thing means going against your own team.

Retaliation Isn’t Always Loud

“It’s the silence. The meetings you stop getting invited to.”

How quiet resistance can be louder than shouting.

Redefining Leadership

“I don’t want to lead the way they taught us. I want to lead in a way that reflects my truth.”

Why he’s rebuilding his leadership from the ground up.

The Work Continues—But Differently

“My goal now isn’t to win office. It’s to win trust.”

From political power to public service, on his own terms.

_______________________________

Connect with us:

Host: Vince Chan | Guest: Brian Sims

--Chief Change Officer--

Change Ambitiously. Outgrow Yourself.

Open a World of Expansive Human Intelligence

for Transformation Gurus, Black Sheep,

Unsung Visionaries & Bold Hearts.

EdTech Leadership Awards 2025 Finalist.

20 Million+ All-Time Downloads.

80+ Countries Reached Daily.

Global Top 1% Podcast.

Top 5 US Business.

Top 1 US Careers.

>>>200,000+ are outgrowing. Act Today.<<<

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In Part One, Brian walks us through the pivotal moments that shaped his path—from coming out as a college athlete to confronting power structures as a civil rights lawyer. He shares how being raised by military parents shaped his moral compass, how football taught him about leadership under pressure, and why he believes his queerness has made him a better, sharper advocate. This is the story of a public servant forged in fire—and not afraid to stay loud.

Key Highlights of Our Interview:

The Day Job and the Gay Job

“There was work I did to earn a living. And work I did to sleep at night.”

Brian’s legal path wasn’t linear—it was moral. Disability law by day, LGBTQ+ advocacy by choice. The real career came when he fused both.

Feminist Lawyer at Age 12

“I told people I wanted to be a feminist lawyer… before I even knew what that fully meant.”

His mother’s defiance of gender roles shaped more than his politics. It gave him a framework for justice—before he ever came out.

Raised by a Combat Nurse with a Crew Cut

“She probably got accused of being a lesbian once a week in the military. It didn’t harden her—it strengthened her.”

Growing up with two military parents meant discipline and love. But it was his mother’s quiet power that taught him to be an upstander, not a bystander.

Coming Out—and Coming Into Power

“My teammates waited until they knew I’d be safe to ask me if I was gay.”

Brian’s coming out wasn’t loud—it was supported. That emotional safety net shaped how he now builds space for others.

From Closet to Capitol

“Eight months before I took office, I knew I was the only out person in the room. But I also knew I wasn’t the only one.”

Brian didn’t just fight for LGBTQ+ rights—he stood up for racial justice, reproductive rights, and equality as a full strategy. Being gay got him elected. Being an ally kept him effective.

_______________________________

Connect with us:

Host: Vince Chan | Guest: Brian Sims

--Chief Change Officer--

Change Ambitiously. Outgrow Yourself.

Open a World of Expansive Human Intelligence

for Transformation Gurus, Black Sheep,

Unsung Visionaries & Bold Hearts.

EdTech Leadership Awards 2025 Finalist.

20 Million+ All-Time Downloads.

80+ Countries Reached Daily.

Global Top 1% Podcast.

Top 5 US Business.

Top 1 US Careers.

>>>200,000+ are outgrowing. Act Today.<<<

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In Part Two, Kevin Eikenberry challenges the myth that leadership is just for those with formal authority. He unpacks the idea of “leadership by choice,” reflects on the rise of remote work, and shares practical advice for building influence, trust, and connection—especially when you’re not in the same room. With insights from decades of coaching and his own mistakes, Kevin makes a compelling case: the future of work belongs to people who choose to lead, wherever they are.

Key Highlights of Our Interview:

Leadership Isn’t a Title

“You don’t need a position to lead. You just need to make the choice.”

Why influence, not authority, defines real leadership.

From Compliance to Commitment

“Command and control can get people to do the work. But it won’t make them care.”

How great leaders inspire action—not just obedience.

Remote Work Is Here to Stay

“Hybrid is the reality. The leaders who adapt will win.”

Why resisting change isn’t a strategy—and what to do instead.

Trust Can Travel

“Distance doesn’t have to mean disconnection.”

Building rapport, connection, and shared purpose in remote teams.

Be a Student of Your Own Leadership

“Every leader needs a development plan—just like athletes have coaches.”

Why leadership is a daily practice, not a fixed identity.

____________________________

Connect with us:

Host: Vince Chan | Guest: Kevin Eikenberry

>>>Your $79 free gift is here for you to accept -- not a scam, it's a personal gift from Kevin to you.

--Chief Change Officer--

Change Ambitiously. Outgrow Yourself.

Open a World of Expansive Human Intelligence

for Transformation Gurus, Black Sheep,

Unsung Visionaries & Bold Hearts.

EdTech Leadership Awards 2025 Finalist.

20 Million+ All-Time Downloads.

80+ Countries Reached Daily.

Global Top 1% Podcast.

Top 5 US Business.

Top 1 US Careers.

>>>200,000+ are outgrowing. Act Today.<<<

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In Part One, Kevin shares the personal and professional journey that shaped his leadership philosophy—from farm life to corporate training to becoming a global thought leader. He explains why leadership isn’t about innate traits or job titles, but about everyday choices. Drawing from his early career, client work, and lessons from home, Kevin lays out why leading by default isn’t enough—and how you can start leading by design.

Key Highlights of Our Interview:

From the Farm to the Front of the Room

“I didn’t grow up thinking I’d teach leadership. But I grew up watching it.”

How growing up on a farm quietly planted the seeds of leadership.

Default Mode Isn’t Leadership

“Too many people lead by accident. They react. They wing it. And it shows.”

Why awareness and intention are the real foundations of influence.

Leadership Is Learned, Not Born

“No one gets promoted and magically becomes a leader.”

The myth of the ‘natural leader’—and why it holds people back.

Everyday Moments Matter Most

“Leadership shows up in the way you write an email, run a meeting, or give feedback.”

The seemingly small actions that build—or break—trust.

The First Step Is a Mirror

“If you want to lead others, you have to lead yourself first.”

Why self-awareness is the starting point of every leadership journey.

____________________________

Connect with us:

Host: Vince Chan | Guest: Kevin Eikenberry

--Chief Change Officer--

Change Ambitiously. Outgrow Yourself.

Open a World of Expansive Human Intelligence

for Transformation Gurus, Black Sheep,

Unsung Visionaries & Bold Hearts.

EdTech Leadership Awards 2025 Finalist.

20 Million+ All-Time Downloads.

80+ Countries Reached Daily.

Global Top 1% Podcast.

Top 5 US Business.

Top 1 US Careers.

>>>200,000+ are outgrowing. Act Today.<<<

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In Part Two, Adaira Landry goes beyond storytelling and gets strategic—explaining how to stop saying yes to everything, avoid burnout, and take back control of your time. She shares how the original title of her book almost became Chisel, why Micro Skills isn’t meant to be read cover to cover, and what FOMO vs. JOMO really means in your career.

This episode is a mindset shift for anyone who’s overcommitted, overextended, or overdue for some clarity. Her message is simple but powerful: just because you can do something, doesn’t mean you should.

Key Highlights of Our Interview:

The Book Almost Had Another Name

“We wanted to call it Chisel. But it didn’t land the way we hoped. Micro Skills captured it better—it’s about precise, meaningful action.”

Ambition Without Boundaries Isn’t Sustainable

“I used to say yes to everything. Then I realized—none of it was helping me grow upward. It was just clutter.”

Say No to Say Yes

“JOMO—the joy of missing out—is real. You don’t need to chase every opportunity. You need to choose the right ones.”

The Burnout Trap

“If you’re always working horizontally, you never move vertically. That’s not growth. That’s noise.”

Fast Impact, Not Magic

“You don’t need a new degree or a big life change. You just need to start—small, now, and with purpose.”

_____________________

Connect with us:

Host: Vince Chan | Guest: Adaira Landry MD

--Chief Change Officer--

Change Ambitiously. Outgrow Yourself.

Open a World of Expansive Human Intelligence

for Transformation Gurus, Black Sheep,

Unsung Visionaries & Bold Hearts.

EdTech Leadership Awards 2025 Finalist.

20 Million+ All-Time Downloads.

80+ Countries Reached Daily.

Global Top 1% Podcast.

Top 5 US Business.

Top 1 US Careers.

>>>200,000+ are outgrowing. Act Today.<<<

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.