FailCraft

Do you have a dream you’ve been sitting on for years, but you secretly feel like you’ve "aged out" or it’s simply too late to start? Buddy Howard spent decades as a high-stakes Mergers & Acquisitions executive and financial expert witness. But at age 67, he decided to completely start over as a novice and publish his debut legal thriller, The Burden of Evidence. This episode dives in...

Why do so many expensive corporate leadership programs end up collecting dust in a drawer? Maren Perry, Founder & CEO of Arden Coaching, has spent nearly two decades navigating the messy, human side of leadership. She joins the show to reveal why traditional leadership training fails (hint: it's not a lack of data) and how to break through the egos and excuses of highly resistant executive...

Do you feel like you are just drifting through life—going through the motions, lacking pride, and secretly knowing you aren't living up to your potential? Maxim Shapiro, a Men’s Action Life Coach, knows that feeling intimately. For 40 years, he lived a "rudderless" life, trapped in a cycle of high-functioning depression and self-deception. It took a brutal wake-up call and the fierce...

Dianna Deeney is a product development expert with over 25 years of experience spanning the manufacturing floor to leading design teams. She specializes in the "fuzzy front end" of creation, helping engineering teams transform early-stage ideas into clear, user-focused designs. Dianna is the founder of Quality During Design, the author of "Pierce the Design Fog," and the creato...

What happens when the financial expert who supposedly "has it all figured out" loses everything and ends up on food stamps? Chris Miles, founder of Money Ripples and the "Anti-Financial Advisor," achieved the ultimate dream of retiring at age 28. But when the Great Recession hit, his real estate portfolio crumbled, leaving him over $1,000,000 in debt. Facing foreclosure, repo m...

What do you do when your life spirals into complete chaos—navigating an unexpected divorce, two kids at home, and the sudden, terrifying birth of micro-preemie twins weighing less than two pounds each? Tami Gaines, founder of Sage Enterprises and author of Preemie Parents, shares the raw, emotional story of living inside the Neonatal Intensive Care Unit (NICU). Instead of crumbling under the relen...

Are you pushing your teenager onto a "conveyor belt" toward a 4-year college just because it's what you are supposed to do? Prasant Nukalapati, an admissions expert and founder of What Comes Next Ed Consulting, has spent 27 years watching the traditional high-school-to-college pipeline leave too many students feeling anxious, lost, and directionless. In this episode, he exposes the m...

Do you feel like you are stuck in an endless scroll, mindlessly consuming content, or burning out on dating apps that never lead to real connection? Tobias Mark Jensen, a legal technology expert and author of Death to Algorithms, joins the show to expose the invisible forces shaping our daily lives. He breaks down how the algorithms we trust for entertainment, romance, and information are fundamen...

What do you do when the only life plan you ever had—being a stay-at-home mom—suddenly ends in divorce after 21 years? Lorie Kleiner Eckert found herself facing this exact crisis at age 42. Instead of freezing, she decided to turn her hobby of quilting into a professional speaking career—inventing a "quilt lecture circuit" that didn't even exist! Fast forward 30 years, and Lorie is no...

How do you keep living when the banks take your properties, your personal belongings, and lock you out of your own home while slapping you with a $5,000,000 debt? Roy Coughlan, a serial entrepreneur who has founded over 20 companies across 5 countries, shares the harrowing reality of losing everything during the 2008 financial crash. He opens up about the devastating emotional toll of watching his...

Why do smart leaders make terrible decisions under pressure? And why does giving feedback often backfire and ruin team morale? Yosi Kossowsky, an executive coach and former Chief Technology Officer, joins the show to explain the fascinating neuroscience behind leadership failures. He breaks down how our brains literally shut off access to our executive thinking function (the prefrontal cortex) whe...

What do you do when you've dedicated nearly 30 years to the corporate IT world, only to have your position eliminated right before your 60th birthday? Jim Hauck, founder of JP Hauck Adventures and co-host of the *Life in the Baggage Claim* podcast, shares the reality of facing a forced career pivot later in life. Instead of desperately searching for another corporate job, Jim decided to walk a...

How do you go from flipping burgers as an immigrant kid in Dallas to being named the "Oracle of Austin" by Forbes and managing a multi-billion-dollar real estate empire? You fail. A lot. Ari Rastegar, Private Equity CEO and author of the *New York Times* bestseller *The Gift of Failure*, sits down to share the unfiltered truth about what it really takes to scale to the top. He opens up a...

Andrea LeDew was trained as a lawyer to fight with briefs and contracts, but when the systems around her began to fail, she found a different weapon: creative writing and poetry. In this episode, Andrea shares her journey of stepping away from a legal career to raise a child with autism and intellectual disabilities. She opens up about the heartbreaking moment her son internalized the cruelty of s...

What happens when a West Point graduate and combat veteran takes his hypervigilance to Wall Street, only to realize the "tough it out" mentality is slowly killing him? Omar Ritter, a former Army officer and CFO, shares his incredible journey of surviving war, corporate burnout, and an 18-hour brain surgery. He opens up about the devastating string of suicides among his friends that serve...

What happens when your picture-perfect life is shattered overnight, and the dream you were building suddenly disappears? Chanoa Inez, author of *Dream On* and creator of MAGNETIZE YOUR PERSONAL BRAND™, shares the devastating story of losing her boyfriend suddenly while on a trip to Montenegro. She opens up about the dark years that followed, how the trauma manifested as physical health issues, and...

What happens when a doctor looks you in the eye and tells you that if you don't change your lifestyle immediately, you won't live to see your five-year-old daughter grow up? Hipolito Montero was faced with this terrifying reality in 2019 when chest pains led to a shocking diagnosis: his heart was 53% larger than normal. Weighing 130kg and struggling with severe self-doubt, he was given an...

What happens when you spend your entire life outrunning childhood trauma by being the "perfect" mom, wife, and professional—until the mask finally falls off? Katie Baker, author of *When The Universe Holds Your Hair Back*, shares her raw and unflinching journey from high-functioning survival mode to hitting rock bottom in her late 40s. She opens up about the devastating moment her teenag...

What do you do when you spend decades climbing the corporate ladder, only to realize it's leaning against the wrong wall? Daniel C. Rodgers, a former program manager at tech giants like Microsoft and Google, reached the peak of his career and realized he was trapped on a high-paying treadmill. He achieved financial independence and retired at 43, but the hardest part wasn't the math—it was...

Are you pouring hours into your podcast or content marketing, only to hear crickets and see zero ROI? Virginia Elder, founder of Podcast Abundance, joins the show to explain why the "Do It All Yourself" content grind is a one-way ticket to burnout. She shares the ironic story of running a successful podcast agency while her own podcast sat dead in the water, and how she finally built sys...

What happens when an engineer tries to apply logic to the most broken, irrational system in America: politics? Dan Schaefer, an engineer and progressive candidate, ran for the Missouri House of Representatives in a deep-red district. He lost the election, but he didn't lose his resolve. Dan joins the show to discuss why the real failure isn't losing a vote—it's refusing to enter the ar...

What happens when you build the "perfect" life—the house, the career, the family—but your body literally breaks down to stop you from living it? Karina, who writes under the pen name K.K. Biernath, shares her powerful story of immigrating from Poland to the US, checking every box of societal success, and running herself into the ground. She opens up about the physical toll of perfectioni...

What happens when a near-death experience violently forces your mind and soul wide open? Nancy Orlen Weber, a former registered nurse, survived a horrifying domestic attack while five months pregnant by pretending to be dead. That profound trauma became the unexpected doorway to a life-altering awakening. For the last 40 years, Nancy has used her resulting intuitive gifts as a psychic detective—he...

What do you do when you are a highly successful business coach with 30 years of experience, a stable marriage, and all the personal development tools in the world—yet you feel completely flat and resigned inside? Laura Watson, founder of Venture Coaching International, shares her vulnerable journey of hitting a mid-life wall. Despite knowing all the coaching frameworks, she found herself secretly...

What happens when your spouse calls you with a cancer diagnosis, and your terrifying second thought is, "We can't afford to fight this"? Bart Merrell, a serial entrepreneur and amputee, shares his wild and inspiring journey of surviving life's hardest curveballs. From taking the first commercial bungee jump to Japan (and jumping while holding the cord with his bare hands), to los...