Best Josh Chernikoff Podcasts (2025)

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You Crushed the Demo—But Still Can’t Close: The $100K Mistake Education Founders Keep Making 18:58

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5d ago18:58

18:58

You crushed the demo. The buyer smiled. They nodded. They even said, “This is exactly what we need.” And then… nothing. That silence isn’t harmless. Every “We’ll be in touch” costs you weeks of follow-up, lost momentum, and deals that should already be on your books. In Part 1, “Your Demo Is the Problem” with John Gamba, Entrepreneur in Residence a…

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Looking Back: Katie Anderson & Isao Yoshino on Learning, Leadership, and Mistakes 39:35

10d ago39:35

39:35

We’re going back to Episode 30 from January 2021, featuring Katie Anderson — author of Learning to Lead, Leading to Learn — and Isao Yoshino, the longtime Toyota leader whose career and lessons inspired her book. Episode page with video, transcript, and more It was such a privilege to talk with them then, and even more meaningful now, because I rec…

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From Betrayal and Courtroom Battles to Closed Deals: Robespierre Reyes on Rebuilding Credibility, Team Alignment, and Education Deals That Close 19:05

12d ago19:05

19:05

Robespierre Reyes had funding, traction, and a winning idea. Then came the lawsuits, burnout, and partners who betrayed him. Four companies, three failures, one courtroom showdown. His confidence, credibility, and pipeline of leads were all at risk. Most founders would quit. Rob didn’t. Instead, he rebuilt everything that actually drives qualified …

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From the Wrong Business to the Right Voice: Emily Aborn on Finding Purpose Through Mistakes 42:03

17d ago42:03

42:03

My guest for Episode #328 of the My Favorite Mistake podcast is Emily Aborn, a small business copywriter, speaker, and host of the Small Business Casual podcast. Episode page with video, transcript, and more Emily helps entrepreneurs bring clarity, creativity, and authenticity to their marketing. Before finding her true calling, she owned a brick-a…

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From Confusion to Clarity: JD Mosley-Matchett on the Message Shift That Turns Unclear Offers into Scalable, Trust-Building Growth for Education Founders 18:36

19d ago18:36

18:36

Most education founders and EdTech leaders think their problem is marketing. But sometimes, the real issue is something more critical: Clarity If your message isn’t clear, your market stops listening, no matter how brilliant your solution is. That was the hard truth J.D. Mosley-Matchett, PhD had to face. As the Founder & CEO of InforMaven.AI, JD’s …

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Can AI Be Humble? Maya Ackerman on What Machines Teach Us About Creativity 43:16

24d ago43:16

43:16

My guest for Episode #327 of the My Favorite Mistake podcast is Dr. Maya Ackerman, AI pioneer, researcher, and CEO of WaveAI. She’s also an associate professor of Computer Science and Engineering at Santa Clara University and the author of the new book Creative Machines: AI, Art, and Us. EPISODE PAGE WITH VIDEO, TRANSCRIPT, AND MORE In this episode…

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The Mindset Reset: Mitch Weisburgh On How Education Founders Can Master Mindset, Beat Burnout, and Close Strong Deals 36:54

26d ago36:54

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You’ve got the product, the drive, and the skills, but when pressure hits, your mindset starts to crack. Suddenly, deals stall, momentum fades, and even your warmest prospects go quiet. The harder you push, the less it seems to move forward. Most education founders panic. They double down on demos, CRMs, late nights, and new pitches, thinking more …

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Trust, Leadership, and Learning From Mistakes: William Harvey on Building a Safe and Excellent Workplace 47:24

1M ago47:24

47:24

My guest for Episode #326 of the My Favorite Mistake podcast is Dr. William Harvey, a manufacturing executive and university professor whose career is defined by developing people, strengthening systems, and driving organizational excellence. A proud U.S. Marine, William carries forward a deep tradition of service and leadership. He also serves as …

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Stop Delegating Sales: Why Education Founders Must Sell Their Solution First Or Watch Their Pipeline Die 14:05

1M ago14:05

14:05

Most education founders think the next rep, agency, or AI tool will solve their sales problem. It won’t. Here’s the truth: if you can’t sell your own offer clearly, no one else can. Every lead you hand off too early is wasted time, lost money, and a pipeline headed for collapse. Every day you delay founder-led sales is another day your growth stall…

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Archives: From Shame to Self-Awareness — A Leadership Transformation with Sabrina Moon 36:13

1M ago36:13

36:13

In this bonus re-release, we revisit an important and timely conversation with Sabrina Moon, Founder and CEO of The Problem Solving Institute and a certified Dare to Lead™ facilitator. Originally aired as Episode #35 of My Favorite Mistake, this conversation remains one of the most powerful and honest reflections on leadership, shame, and transform…

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From Lost Leads to Locked Contracts: Paul King on Niche Focus, Pilots That Convert, and Closing Education Deals 32:38

1M ago32:38

32:38

What happens when you stop trying to serve every school and start solving one urgent problem for the right schools? It’s the positioning shift most founders resist—but it’s the exact move that transforms “just another vendor” into a mission-critical partner. That’s why this episode of Breaking the Grade is essential listening: Josh sits down with P…

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Failing My Way to Success: Phillip Cantrell on Scaling vs. Scrambling in Business 39:01

2M ago39:01

39:01

My guest for Episode #325 of the My Favorite Mistake podcast is Phillip Cantrell, EVP of Strategy at United Real Estate, founder of Benchmark Realty, and author of Failing My Way to Success: Lessons from 42 Years of Winning and Losing in Business. EPISODE PAGE WITH VIDEO, TRANSCRIPT, AND MORE Phillip reflects on more than four decades of entreprene…

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The Education Founder’s Blueprint: Kevin Chavous on Turning Setbacks Into Proof Points, Credibility, and Growth That Lasts 47:41

2M ago47:41

47:41

Most education founders think buyers want the perfect pitch, the flashy product, or the right political connection. But Kevin Chavous—national education reformer, bestselling author, and President of Stride, Inc. proves that none of those close deals. What does? Credibility, proof, and persistence. This episode is extra special because Kevin was th…

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Spinal Tap’s Greatest Mistakes — And Why They Still Matter 41 Years Later 13:40

2M ago13:40

13:40

In this very special solo episode of My Favorite Mistake, Mark Graban breaks down the gloriously ridiculous — and surprisingly instructive — mistakes made by the characters in his all-time favorite film, This Is Spinal Tap. With the long-awaited sequel, Spinal Tap II: The End Continues, now in theaters, Mark explores why Spinal Tap endures not just…

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The Guarantee Shift: Karim Kuperhause on How Education Founders Build Trust and Win Qualified Leads Without Sounding Desperate 44:59

2M ago44:59

44:59

What happens when a superintendent or a higher ed leader—looks you in the eye and asks: “What happens if this doesn’t work?” For most education founders, that’s the deal-killer moment. They freeze. They dodge. They hide behind buzzwords. And the buyer walks away unconvinced. But here’s the truth: In today’s market, whether it’s K–12 districts or hi…

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How an MLM Failure Taught Trevor Schade to Lead, Grow, and Succeed in Real Estate 45:02

2M ago45:02

45:02

My guest for Episode #324 of the My Favorite Mistake podcast is Trevor Schade. Episode page with video, transcript, and more Trevor began his career as a Lean Six Sigma Black Belt with a strong background in coding and process improvement. He consulted on business efficiency and outsourcing before shifting into real estate in 2008. After earning hi…

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From Invisible to Irresistible: Michael Campbell on Using Research and Proof to Build Trust, Generate Leads, and Drive Education Growth 28:31

2M ago28:31

28:31

Every education founder, EdTech CEO, and school leader wants growth. But here’s the mistake almost everyone makes: they chase revenue before they’ve earned trust. In education, trust is the real currency—it turns a pitch into a meeting, and a meeting into a deal. In this episode, I’m joined by Michael Campbell, president of Advancing Global EDU, In…

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$9M Raised, Zero Guesswork: How YourWay Raised $9M by Solving the Lead Gen Problem Most Education Founders Ignore 27:14

2M ago27:14

27:14

Most education founders don’t fail because of bad ideas. They fail because they lean too hard on “AI-powered” buzzwords, skip the research-to-practice proof buyers demand, and don’t form the partnerships that give them credibility and attract the right leads. That’s the cycle YourWay Learning set out to break. Back in January, at the IFE Conference…

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NFL Kickers on Mistakes, Pressure, Rejection, and How to Succeed in Football and Life 10:03

2M ago10:03

10:03

In this special episode of My Favorite Mistake, host Mark Graban celebrates the kickoff of football season with a unique perspective: five legendary kickers who know what it means to perform under pressure. Guests include former NFL kickers Jay Feely, Shane Graham, David Akers, Nick Lowry, and University of South Carolina’s all-time leading scorer …

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Mistakes in Houses and Hospitals: Grace Bourke on Trust, Verification, and Lasting Improvement 53:45

2M ago53:45

53:45

My guest for Episode #323 of the My Favorite Mistake podcast is Grace Bourke, Consulting Director of the Performance Excellence Practice at Baker Tilly. With nearly 40 years of experience in healthcare quality improvement and industrial engineering, Grace has worked in clinical care, biotech, global public health, and senior leadership roles at org…

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From “Great Pitch” to Signed Contract: Paul Vallas on the Buyer’s Lens That Closes Education Deals 23:56

2M ago23:56

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What happens when you finally land the big meeting… and walk out with nothing but “We’ll think about it”? It’s the growth killer most founders don’t see coming—your pitch isn’t aligned with how education buyers actually make decisions. That’s why this live Breaking the Grade episode from ASU-GSV (the edtech conference each April in sunny San Diego)…

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Quitting My PhD: Rob Dorgan on Redefining Success, Beating Burnout, and Finding Purpose 43:32

3M ago43:32

43:32

My guest for Episode #322 of the My Favorite Mistake podcast is Rob Dorgan, a multi-talented professional whose career path has taken him from paralegal to college professor, retail store owner, manufacturing company president, and now licensed massage therapist, certified yoga educator, meditation teacher, and astrologer. Rob is also the author of…

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(Re-Air) The Signature Solution: Your Proven Blueprint to a Clear Offer That Generates Leads and Wins the Education Market 17:08

3M ago17:08

17:08

What if your biggest lead gen problem isn’t visibility — but the fact that your offer isn’t clear enough to close? Most EdTech founders think they have a marketing problem. Some think it’s a sales problem. But what they actually have is this: ❌ An offer that’s vague ❌ A proven model that’s undefined ❌ And no document that makes buyers say “yes” on …

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Why Listening to Yourself Is the First Step to Better Communication — Cynthia Kane on Learning to Pause 42:19

3M ago42:19

42:19

My guest for Episode #321 of the My Favorite Mistake podcast is Cynthia Kane, founder and CEO of the Kane Intentional Communication Institute and author of several books, including How to Communicate Like a Buddhist and The Pause: How to Keep Your Cool in Tough Situations. Cynthia shares a pivotal mistake from early in her life: letting other peopl…

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From $10M in Sales to Losing Her Company: What Education Founders Learn the Hard Way About Selling, Scaling, and Staying Aligned 26:12

3M ago26:12

26:12

Most founders think their growth problem is sales. But Jolene Levin, entrepreneur, innovator and founder of NorvaNivel proved it’s the other way around: your sales reveal your growth problem. Jolene founded a classroom furniture company in Australia, scaled it across schools, and then brought it to the U.S. Three months after launching in the U.S.,…

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From Lab Work to Leadership: Dr. Jen Heemstra’s Guide to Thriving in Science Careers 11:39

3M ago11:39

11:39

🎙️ In this bonus episode of My Favorite Mistake, Mark Graban welcomes back Dr. Jen Heemstra, Charles Allen Thomas Professor and Chair of Chemistry at Washington University in St. Louis. Jen joins us to talk about her new book, Lab Work to Leadership: A Concise Guide to Thriving in the Science Job You Weren’t Trained For. She shares how the book was…

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The Costly Expansion Mistake That Made Damon Lembi a Better 'Learn it All' CEO 43:53

3M ago43:53

43:53

My guest for Episode #320 of the My Favorite Mistake podcast is Damon Lembi, CEO of Learnit, a live learning and development platform that has helped upskill over 2 million professionals. Episode page with video, transcript, and more A former college baseball player and now a two-time bestselling author, Damon shares the story of how youthful ambit…

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(Best of) Your Demo Is the Problem: What Education Founders Must Do—and Stop Doing—to Close More Deals With Their Demos 35:20

3M ago35:20

35:20

Most EdTech demos fall flat because they focus on product—not pain. They walk through features—but skip the funding strategy. They sound polished—but feel disconnected. And when the call ends? No buy-in. No follow-up. No deal. That’s where John Gamba changes the game. John isn’t just an expert in EdTech innovation—he’s coached thousands of educatio…

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Your Work Won’t Speak for Itself: Mistakes & Branding Lessons from Sapna Pieroux 44:46

3M ago44:46

44:46

My guest for Episode #319 of the My Favorite Mistake podcast is Sapna Pieroux, award-winning author of Let’s Get Visible!, a branding consultant, and the founder of Inner Visions ID. Episode page with video, transcript, and more With a background spanning 20 years in media and experience working with major brands like Toyota, Sony, and L’Oréal, Sap…

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From Collapse to Credibility: Robert Martellacci’s Blueprint to Win Back Influence and Close Deals in the Education Space 33:37

3M ago33:37

33:37

What happens when your billion-dollar success story ends—and the market forgets your name? Robert Martellacci knows. And he didn’t quit—he reinvented. This episode isn’t just about resilience. It’s about the bold mindset shift it takes to reclaim relevance, rebuild trust, and restart traction when everything you built gets wiped off the board. Robe…

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The Art of Preventing Stupid: Lawyer and Author Matthew Davis on Business Mistakes and Growth 45:12

4M ago45:12

45:12

My guest for Episode #318 of the My Favorite Mistake podcast is Matthew Neal Davis, an attorney, entrepreneur, and author of the provocative book The Art of Preventing Stupid. Episode page with video and more Matthew is the founder and managing partner of Davis Business Law, which has grown more than 1,000% in six years, earning a spot on the Inc. …

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From Dead-End to C-Suite: An Edtech’s Messaging Framework That Converts Education Conversations into Contracts 15:33

4M ago15:33

15:33

Here's the Messaging Fix You Didn’t Know You Needed If your EdTech offer sounds “nice” but never gets past your perfect client to respond… this episode is your wake-up call. Carlos Zapata, founder of Unicorn Academy, joins me live from the IFE Conference in Monterrey, Mexico — and pulls back the curtain on the exact moment his company stopped stall…

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Why Going to Law School Was Her Favorite Mistake – Davina Frederick of Wealthy Woman Lawyer 44:47

4M ago44:47

44:47

My guest for Episode #316 of the My Favorite Mistake podcast is Davina Frederick, founder of Wealthy Woman Lawyer, host of the Wealthy Woman Lawyer Podcast, and a business coach who has helped women law firm owners scale their practices to seven figures and beyond. Episode page with video, transcript, and more In our conversation, Davina shares why…

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Your Summer Fix: How Education Founders Can Rebuild Lead Flow Before Back-to-School 14:38

4M ago14:38

14:38

Let’s get one thing straight: September doesn’t start in September. It starts now—in June, July, and August. Because the biggest mistake founders make in summer isn’t taking a break. It’s confusing rest with silence. You can recharge and still generate leads. But most EdTech founders go dark. They hunker down. Rebuild ops. Tweak product. And comple…

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The Danger of Optimism: CEO Jim Schleckser on His Biggest Leadership Mistake 49:22

4M ago49:22

49:22

My guest for Episode #316 of the My Favorite Mistake podcast is Jim Schleckser, founder and CEO of The CEO Project. Episode page with video, transcript, and more Jim is a seasoned business leader, bestselling author, and trusted advisor to CEOs around the world. With experience spanning 42 countries and multiple industries, Jim has spent decades he…

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From Quiet Posts to Real Revenue: How Anissa Used LinkedIn to Build Trust and Attract Qualified Leads 41:07

4M ago41:07

41:07

Most EdTech founders are still chasing views. Anissa Bouderraoui is closing pilots. She didn’t wait to go viral. She showed up consistently—with clarity, credibility, and the kind of messaging school leaders actually respond to. The result? No gimmicks. No funnels. Just a pipeline built on trust. Bolstered by LinkedIn consistency. 🎯 When Anissa sta…

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Why 100 Coffee Meetings Didn’t Work—And What Kat Halushka Did Instead 37:43

4M ago37:43

37:43

My guest for Episode #315 of the My Favorite Mistake podcast is Kat Halushka, a business and visibility strategist for coaches, consultants, and speakers. She’s the founder of Profitable Impact Academy, where she helps entrepreneurs grow their audience, automate marketing, and land clients through speaking and streamlined funnels. EPISODE PAGE Kat’…

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The Rest Advantage: How Education Founders Use Strategic Pauses to Spark Lead Gen Breakthroughs 14:31

4M ago14:31

14:31

Most education founders treat traction like a treadmill. When the leads slow down, they don’t stop to ask why—they sprint faster. More posts. More emails. More calls. More grind. But here’s what most founders miss: 📉 Motion ≠ Momentum 📉 Hustle ≠ Clarity 📉 Activity ≠ Conversion In this episode, Josh goes solo to unpack a hidden truth in EdTech sales…

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How Culture Creates Freedom and Profit: Josh Cunningham Returns to Share His New Book 13:57

4M ago13:57

13:57

In this special bonus episode of My Favorite Mistake, host Mark Graban welcomes back Josh Cunningham, founder and CEO of Rokrbox and guest from Episode 244. Josh returns to share insights from his brand-new book, Culture Is the Key: How to Unlock Massive Profits and Freedom. We dive into: How Josh built a culture-first company that’s thriving—even …

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The Mistake of Unrealistic Expectations: Mark Struczewski’s Solopreneur Journey 44:03

5M ago44:03

44:03

My guest for Episode #314 of the My Favorite Mistake podcast is Mark Struczewski, also known as “Mister Productivity.” Mark is a Houston-based productivity coach, speaker, and host of The Mister Productivity Podcast, with over 1,300 episodes to his name. He helps overwhelmed professionals cut through distractions and focus on what truly matters. Ep…

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Clearer Messaging, Consistent Leads: What EdTech Founders Can Learn from MindShifting 36:11

5M ago36:11

36:11

Most education companies don’t lose leads because their product is weak. They lose them because the message doesn’t land. They try to sound professional. Strategic. Smart. But polish ≠ presence. And clever ≠ clear. In this episode, Josh sits down with Mitch Weisburgh—a lifelong educator, EdTech veteran, and founder of MindShifting with Mitch—to unp…

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Avoiding Bad Marketing: Amber Gaige on Mistakes, AI, and the Four Cs 32:41

5M ago32:41

32:41

My guest for Episode #313 of the My Favorite Mistake podcast is Amber Gaige, a marketing strategist, international bestselling author, and founder of Far Beyond Marketing. With over 20 years of experience, Amber helps entrepreneurs simplify their marketing and drive real results. She’s also the author of The Far Beyond Marketing Guidebook: Stop Bei…

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Do the Opposite of Everything You’ve Been Doing: How Seinfeld’s George Costanza Unlocks Lead Gen Clarity for EdTech Founders 17:42

5M ago17:42

17:42

Let’s start with a sitcom—and a truth bomb. In Seinfeld Season 5, Episode 22 ("The Opposite"), George Costanza hits rock bottom. No job. No love life. No confidence. So he flips the script. “If every instinct I have is wrong, then the opposite must be right.” And suddenly? He orders chicken salad instead of tuna. He tells the girl he’s unemployed a…

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Ballet, Mistakes, and Masked Performances: Jared Redick’s Story of Grace Under Pressure 42:44

5M ago42:44

42:44

OOPS! Due to an editing mistake, I had to reupload the file. Again. My guest for Episode #312 of the My Favorite Mistake podcast is Jared Redick, a third-generation ballet dancer, choreographer, and award-winning educator. Episode page with links and more Jared is a full professor and Assistant Dean of Dance at the University of North Carolina Scho…

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Breaking Borders: How Smart EdTech Founders Build Scalable Companies Without Losing Local Trust 33:06

5M ago33:06

33:06

If you’re trying to grow your education business beyond where you started—this episode is for you. Because whether you’re moving from one country to another, or just one state to the next… The real challenge isn’t translation. It’s trust. In this episode of Breaking the Grade, I sit down with Denise Abulafia—EdTech founder, Penn GSE professor, and …

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How a Mistake in Confronting Workplace Discrimination Shaped a Leadership Career – Karin Hurt on Speaking Up the Right Way 40:51

5M ago40:51

40:51

My guest for Episode #311 of the My Favorite Mistake podcast is Karin Hurt, CEO of Let’s Grow Leaders, a global leadership development firm. Karin is a former Verizon Wireless executive and the award-winning author of five books, including her latest, Powerful Phrases for Dealing with Workplace Conflict. Episode page with video, transcript, and mor…

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The Speaking Strategy: How Education Founders Fast-Track Credibility, Confidence, and Sales Momentum 20:34

5M ago20:34

20:34

LinkedIn builds your credibility — Speaking amplifies it. In this episode of Breaking the Grade, I’m sharing how I went from avoiding stages entirely to speaking at in the last 13 months at Penn GSE, the University of Chicago, SXSW EDU, DC Startup Week, Education Research and Development Institute, XEdu, Institute for the Future of Education in Mex…

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What Nearly Killed Andrew Laws’ Business—and Why He’s Now Grateful for It 41:48

5M ago41:48

41:48

My guest for Episode #310 of the My Favorite Mistake podcast is Andrew Laws, Founder of the SEO agency Yeseo IO and host of The Business Amplifier Podcast. Andrew has been working in digital marketing for over 25 years and has seen just about every shift in the SEO landscape. But one of the biggest lessons of his career came not from Google’s algor…

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From Ghosted to Booked: How Ashton Tate Filled His Calendar with Qualified School Leads 26:03

6M ago26:03

26:03

You’re not afraid of hard work. You’ve put in the hours. You’ve sent the emails. You’ve done the demos. And still—no one’s biting. That was Ashton Tate. Founder of The Form Curriculum. Fitness coach-turned-EdTech founder. 500 cold calls deep… and still stuck. Then he changed one thing. He stopped selling—and started listening. In this episode of Br…

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How Busy Teams Can Better Execute Growth Plans: Andrea Jones on 'Executagility' and Mistakes 14:20

6M ago14:20

14:20

In this special bonus episode of My Favorite Mistake, Mark Graban talks again with Andrea Jones, Principal at AJC and CEO of The Executagility Company. Andrea was previously featured in Episode 105, and she returns to discuss the release of her new book: The Executagility Field Guide: How Busy Teams Can Execute Growth Plans. Andrea shares a new “fa…