#336 Waverly Deutsch: Coaching the Logical, Leading with Love

In Part 2, Waverly Deutsch opens up about her decades at Chicago Booth, where she helped founders refine not just their business models but their ability to lead. She discusses how emotional connection strengthens logic, why confident delivery isn’t enough, and how AI is changing but not replacing human insight. For Gen Xers mentoring across generations or rethinking their own leadership, this episode is a reminder: great guidance begins with deep listening.>>Coaching Across the Confidence Spectrum“Some people came in over-confident. Some barely made eye contact.”She explains how coaching required tailoring—not templating—entrepreneurs’ thinking.>>Why Love Belongs in Leadership“If you can’t connect with your idea, why should anyone else?”Waverly talks about the human element most founders overlook when presenting.>>Building Trust Across Generations“EMBAs bring wisdom. Undergrads bring fire.”She shares the challenge—and joy—of coaching both seasoned execs and young dreamers.>>Relearning Her Own Leadership“Coaching taught me how much I still had to unlearn.”She reflects on what working with thousands of students revealed about her own blind spots.>>AI Is Here—Now What?“AI can write your pitch. But can it build your conviction?”She discusses how tech is changing communication—and why human trust still drives every great pitch._________________________Connect with Us:Host: Vince Chan | Guest: Waverly Deutsch  --Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.EdTech Leadership Awards 2025 Finalist.15 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>150,000+ are outgrowing. Act Today.<<<

We meet Waverly Deutsch not as a Chicago Booth professor or coach for entrepreneurs, but as a real human navigating career decisions in a world that often asks us to pick between passion and practicality. From falling in love with theater to entering computer science as one of only three women in a class of 30, Waverly’s story is one of blending head and heart across every career twist. She shares the real story behind leaving academia for Forrester Research, breaking down in a meeting and still making her case, and learning how to navigate gut instinct and logic without losing either. For Gen Xers raised on rules, she shows what it means to rewrite your own—with emotional truth and strategic clarity.>>Two Majors, One Mindset“I ended up with two majors—one in theater and one in computer science.”Waverly explains how her early passions—performance and programming—formed a lifelong blend of emotion and logic.>>Early Outsider, Early Awareness“There were three or four women in a class of 30.”She shares what it was like being one of the only women in computer science, and how that shaped her views on identity and acceptance.>>Teaching as a Lifelong Thread“I knew that what I wanted to do was teach. That was truly my calling.”From undergrad to her PhD in theater history, teaching remained her throughline—even as industries changed.>>Forrester and the First Real Pivot“I was employee number 27.”She tells the story of joining Forrester Research during its startup phase, helping it scale through the internet boom, and falling in love with entrepreneurship.>>The Crying Meeting“George, I can cry and think at the same time.”Waverly recounts the pivotal moment when she stopped hiding her emotions at work—and started integrating her whole self into how she leads._________________________Connect with Us:Host: Vince Chan | Guest: Waverly Deutsch  --Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.EdTech Leadership Awards 2025 Finalist.15 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>150,000+ are outgrowing. Act Today.<<<

Dominic Carter, CEO of the Carter Group, shares how a personal frustration with his aging parents’ care became a long-term mission: building real, user-driven aging tech in one of the world’s oldest—and most demanding—markets. From human-centric research to venture studio development, Dominic shows how Gen Xers can lead the future of aging by solving the problems we’re all going to face. This isn’t just eldercare innovation—it’s preemptive, practical system design. For those over 50 building what comes next, this episode is a field guide to action rooted in empathy, not hype.>>From Personal Wake-Up Call to Business Blueprint“I wanted better options for my parents—and for myself one day.”Dominic shares how watching his parents’ struggle with aging became the catalyst for a venture into real, human-first aging innovation.>>Aging Tech Isn’t Just for the Elderly“Aging begins at 50—and the opportunity starts there.”He reframes aged tech not as a niche, but as a massive, underserved market hiding in plain sight.>>Start with the User—or Don’t Start at All“If you don’t listen, you’ll waste time, money, and trust.”Dominic explains why most aging tech fails: founders fall in love with ideas, not problems—and skip the hard part: listening.>>Culture Is More Than Geography“The cultural gap between 55 and 75 is as wide as the one between Japan and the West.”He unpacks why aging solutions must be co-designed with users—and adapted not just to national cultures, but age-based subcultures.>>Building Credibility One Win at a Time“Get the use case. Prove the value. Then scale.”Dominic outlines his venture studio strategy—prioritizing two user-validated products (a friction-reducing linen set and a wearable tremor device) to establish proof before expansion.______________________Connect with us:Host: Vince Chan | Guests: Dominic Carter  --Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.EdTech Leadership Awards 2025 Finalist.15 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>150,000+ are outgrowing. Act Today.<<<

Dominic Carter, the CEO of the Carter Group, didn’t become an aging tech founder by chasing trends—he got there by building slowly, listening deeply, and surviving the kind of early burnout that forces reinvention. In Part 1, he shares how moving to Japan, launching businesses, and failing hard shaped the systems-thinking approach that now powers his work on aging innovation. This isn’t a startup story—it’s a Gen X blueprint: steady, lived, built from purpose long before it had a name.>>Leaving, Burning Out, Coming Back“I opened a Tokyo office at 24—and broke myself in the process.”Dominic talks about how early success nearly ruined him, and why walking away was the start of everything good that followed.>>A Life Rebuilt Through Listening“Research made me better—not just at business, but at understanding people.”He shares how market research and consulting sharpened his ability to listen deeply and solve real problems over time.>>No Pivot. Just Evolution.“Every business I built grew from the one before it.”Dominic explains how his work in research, media, and software wasn’t a series of pivots—it was a slow, deliberate build toward relevance.>>Staying in Japan by Choice“I could’ve gone home—but Japan became the place I wanted to change from.”He reflects on the emotional pull of Japan and how the country’s demographic trajectory mirrored something deeper he was starting to feel.>>When Profit Isn’t the Point“I’ve never been obsessed with money. I’ve been obsessed with meaning.”Dominic explains why mission-aligned work—not exits—has always been his driver, even if it meant a longer, less glamorous path.______________________Connect with us:Host: Vince Chan | Guests: Dominic Carter  --Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.EdTech Leadership Awards 2025 Finalist.15 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>150,000+ are outgrowing. Act Today.<<<

This episode offers you $79 worth of value—completely free. Read till the end for the gift.In Part 2, Kevin introduces the core ideas behind his latest book, Flexible Leadership. He explains why leading isn’t about finding the perfect style—it’s about flexing based on the situation without abandoning your principles. We break down how intention, context, and flexors all work together, why rigid leadership labels backfire, and why the best leaders never stop adjusting how they show up.Key Highlights of Our Interview:Why Human Nature Hasn’t Changed“The tools have changed. People haven’t.”Start with Intention“Flexibility doesn’t mean random. It means choosing your leadership moves on purpose.”Context Is Everything“If you don’t read the situation right, no style will save you.”Flexors, Not Labels“You’re not just a ‘visionary’ or a ‘coach.’ Labels can help, but they can also trap.”Compliance vs. Commitment“Sometimes you need quick compliance. Sometimes you need lasting commitment. Know what you’re asking for.”____________________________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 Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.EdTech Leadership Awards 2025 Finalist.15 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>150,000+ are outgrowing. Act Today.<<<

Kevin Eikenberry didn’t start in a leadership lab—he started on a farm where animals had to be fed no matter what else was happening. In Part 1, he shares how early lessons in discipline and systems thinking carried into his leadership work decades later. From his unexpected pivot from fertilizer sales to corporate training, to founding the Kevin Eikenberry Group, Kevin talks about the mistakes, pivots, and realities that shaped his approach to helping others lead better.Key Highlights of Our Interview:Feeding Hogs, Learning Discipline“No matter what else was happening, you had to feed the animals. Non-negotiable.”From Agriculture to Human Systems“I studied mechanical and biological systems. Now I work with human ones.”An Accidental Pivot into Training“I volunteered once at Chevron—and ended up reshaping my whole career.”The Easy Exit, the Harder Lesson“Leaving with projects lined up made it easier—but delayed learning how to market myself.”Keeping the Business Alive“You can’t just be good at the work. You have to keep finding the next work.”____________________________Connect with us:Host: Vince Chan | Guest: Kevin Eikenberry  --Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.EdTech Leadership Awards 2025 Finalist.15 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>150,000+ are outgrowing. Act Today.<<<

In Part 2 of his conversation, Tokyo-based American Gary Bremermann moves beyond his own story to share the frameworks and realities that shape career reinvention today. From his Seven Steps to Career Clarity to his candid views on Japan’s ageist hiring market, Gary offers a Gen X blueprint for change: slow, thoughtful, grounded in values, and fiercely human. For anyone tired of chasing titles and ready to build a career worth living on their own terms, this episode delivers both the hard truths and the hope.>>Coaching the Opportunity Seekers“Mid-career professionals weren’t asking what they wanted—they were asking what was available.”Gary explains why so many talented people get trapped following default paths—and how coaching helps them reconnect with what they actually want.>>Your Story Is the Starting Point“Your past holds the clues to your future—you just have to read it differently.”He breaks down why career clarity begins with mining your real life for patterns, strengths, and missed signals.>>Values Before Vision“Forget the mission statement—start with your values.”Gary shares why starting with personal values, not corporate buzzwords, is the foundation for sustainable career growth.>>Practical Dreaming“One dream job without limits. One dream job grounded in reality.”He explains how a two-track dream job exercise helps people balance ambition with achievable moves.>>Japan’s Aging Workforce and Recruiting Reality“The labor pool is shrinking, but the hiring practices haven’t caught up.”Gary shares firsthand insights on ageism, cultural resistance to change, and why Japan remains one of the hardest recruiting markets in the world._____________________Connect with us:Host: Vince Chan | Guest: Gary Bremermann  --Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.EdTech Leadership Awards 2025 Finalist.15 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>150,000+ are outgrowing. Act Today.<<<

Tokyo-based American Gary Bremermann didn’t stumble into career clarity—he fought for it across countries, careers, and crises. From hitchhiking North America to building and burning out of his first company, Gary’s story is a blueprint for real Gen X reinvention: practical, nonlinear, and painfully honest. In this first of a two-part series, he shares how early travel, entrepreneurial scars, and the brutal experience of misaligned success shaped the recruiter and career coach he is today. For Gen Xers still figuring out their next chapter—or building a life while surviving their own rough drafts—this episode offers both grit and grounded hope.>>The National Geographic Kid“I grew up with every issue ever printed—and a mind wired to explore.”Gary shares how childhood dreams of travel sparked a lifelong hunger for exploration, curiosity, and career experimentation.>>Hitchhiking Lessons You Don’t Learn in Business School“I learned how to talk to anyone, anywhere, about anything.”Gary reflects on how crossing the U.S. and Canada on foot and rail taught him real-world communication skills he still uses as a recruiter and coach.>>Dropping Out—Twice“School couldn’t hold me—but neither could drifting forever.”He talks about his struggles with traditional education, dropping out, traveling the world, and ultimately rebuilding himself on his own terms.>>Entrepreneurial Burnout: The Hidden Cost of Chasing Money“I was expanding globally—and being crushed by my own business.”Gary shares how chasing financial success without personal alignment almost destroyed him—and why selling his first company saved his life.>>Finding Freedom on Different Terms“Money isn’t the goal. Alignment is.”After exiting his business and hiring a life-changing coach, Gary explains how he reframed financial success as a byproduct of purpose, not the point._____________________Connect with us:Host: Vince Chan | Guest: Gary Bremermann  --Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.EdTech Leadership Awards 2025 Finalist.15 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>150,000+ are outgrowing. Act Today.<<<

In the second half of his conversation, Collin Plume moves beyond financial products into financial legacy—sharing how Gen Xers can teach resilience, ownership, and critical thinking to the next generation. From diversifying income streams to protecting family futures with real assets, Collin reveals why wealth isn’t about a flashy portfolio—it’s about building something that lasts, even when systems shift. For Gen Xers tired of flashy advice and ready to raise wiser, stronger humans, this episode delivers the quiet tools for lifelong financial independence.>>Inflation, Instability, and the Fight for Financial Control“Gold has kept up with the cost of living for over 150 years.”Collin explains why owning tangible assets isn’t just smart investing—it’s a fight for personal freedom and future-proofing your life against system shocks.>>Diversification Isn’t Optional Anymore“The mistake isn’t just losing—it’s being stuck in one idea forever.”He shares why today’s market demands diversified thinking, constant learning, and rejecting loyalty to any one asset class—including real estate.>>Retirement Will Never Look the Same“People aren’t retiring—they’re reworking life.”Collin talks about the shifting realities of work, aging, and how side gigs, flexible income, and purpose-driven work are rewriting retirement for Gen X and beyond.>>The Rise—and Risk—of Finfluencers“Algorithms reward appeal, not expertise.”He calls out the dangers of taking financial advice from unverified influencers, and why critical thinking is the real currency in today’s information economy.>>Teaching Kids the Real Value of Money“Experience and education over stuff.”Collin shares how he’s raising his three kids to value assets over toys, experiences over things, and knowledge over hype—with gold and silver as real-world teaching tools.______________________Connect with us:Host: Vince Chan | Guest: Collin Plume  --Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.EdTech Leadership Awards 2025 Finalist.15 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>150,000+ are outgrowing. Act Today.<<<

Collin Plume didn’t build Noble Gold to chase hype—he built it to restore trust in a system Gen X knows can break. In this first of a two-part series, Collin shares how early lessons from insurance sales, real estate, and recession-era survival shaped his people-first approach to wealth building. He explains why real assets like gold and silver aren’t just investments—they’re anchors of ownership in a world increasingly built on debt and paper. For Gen Xers who value resilience over rhetoric, and control over hype, this episode delivers the human side of financial security.>>Learning the Hard Way“Customer service wasn’t a department—it was survival.”Collin reflects on early lessons selling insurance and real estate, where trust and loyalty mattered more than shiny marketing.>>Why People Stay—and Why They Leave“Employees don’t stay because of ping-pong tables. They stay because they’re seen.”He shares how mentorship and genuine relationship-building shaped his leadership style at Noble Gold.>>Selling Without the Sleaze“I don’t care what you’re selling—if you don’t care about people, you lose.”Collin talks about why prioritizing people over products isn’t soft—it’s the only strategy that survives downturns.>>Precious Metals: The Ownership Play“When everything else feels intangible, gold and silver are still yours.”He explains why real assets like precious metals offer Gen Xers a hedge—not just against inflation, but against an unstable system.>>Family, Fear, and Financial Freedom“You’re not just buying an asset—you’re buying options.”Collin connects gold ownership to a deeper human need: protecting family, future, and dignity through real, controllable wealth.______________________Connect with us:Host: Vince Chan | Guest: Collin Plume --Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.EdTech Leadership Awards 2025 Finalist.15 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>150,000+ are outgrowing. Act Today.<<<