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Learnings and Missteps
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Learnings and Missteps

Author: Jesse

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The Learnings and Missteps Podcast is about unconventional roads to success and the life lessons learned along the way.

You will find a library of interviews packed with actionable take aways that you can apply as you progress on your career path.

Through these interviews you will learn about the buttons you can push to be a better leader, launch a business, and build your influence.


Find yourself in their stories and know that your path is still ahead of you.

199 Episodes
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Ever feel overwhelmed by your to-do list? That sensation of drowning in tasks while your most important work gets pushed aside? You're not alone—and there's a solution hiding in plain sight. In this eye-opening episode, Jesse breaks down a deceptively simple framework for identifying exactly which tasks in your life and business should be automated or outsourced. Using a visual "bucket and drops" system, you'll discover how to categorize your work, break large responsibilities into manageabl...
In this episode of the Learnings and Missteps podcast, host Jesse interviews Joseph Richards, the owner and chief takeoff officer at Flooring Takeoffs. Joseph discusses his unique career path, transitioning from an English teacher to a business owner, and the challenges he faced along the way. He talks about the importance of transparency, learning from mistakes, and the role of AI in the estimating world. The discussion also delves into the value of social media in growing a business, the si...
In this episode of the Learnings and Missteps podcast, host Jesse engages with Dr. Alejandra Rodriguez-Mielke, an expert in talent development and organizational analysis, who offers insights on cultural competence and adaptability. Dr. Alejandra shares her journey from Monterey, Mexico, to the United States, highlighting the importance of learning and teaching throughout her career. She emphasizes the significance of interpersonal skills, understanding cultural scripts, and being respectfull...
The Guilt-Free Future Planning method helps prioritize personal goals that consistently get pushed aside when we're busy making things happen for everyone else. This three-step process—Brain Dump, DAMN Matrix, and Walking the Plank—creates a framework for getting your goals out of your head, prioritizing them, and committing to action. • Brain Dump: List all your goals in three categories—business/professional growth, personal growth, and meaningful connections • Focus only on what YOU want,...
In this insightful episode of the Learnings and Missteps podcast, host Jesse interviews Kabri Luhrman Schmid, a nationally recognized construction influencer and project superintendent at Hensel Phelps. Kabri shares her 18-year journey in the construction industry, focusing on complex projects and redefining leadership. The conversation delves into her approach to jobsite leadership, emphasizing the importance of creating environments where workers feel valued and empowered to contribute. K...
In this episode of the Learnings and Missteps podcast, Jesse revisits a conversation with Heather Jones of Archer Estimation and Consulting. Heather shares her insights on battling estimator burnout and stress, her journey to starting a business with her husband, Jake, and their lifestyle as digital nomads. They discuss the impact of traveling on reducing work stress, the importance of learning the local language, and how they manage their business on the go. Heather emphasizes the need for p...
We explore a comprehensive time management framework designed specifically for high achievers who excel at delivering for others but struggle to prioritize themselves. This system helps you honor personal commitments without sacrificing performance, using a three-phase approach that reduces stress and increases focus. • The Self-First Time Mastery Framework addresses the common problem of deprioritizing personal goals • Guilt-Free Future Planning helps extract priorities from your mind and o...
Reclaiming the Voice of Professional Moms with Chelsea Boateng In this episode of the Learnings and Missteps podcast, host Jesse interviews Chelsea Boateng, founder of The Professional Parent. Chelsea shares her expertise in helping high-achieving women navigate the intersection of professional and motherhood identities. They discuss the mental and emotional load carried by mothers, the importance of reclaiming one's voice, and the steps women can take to design a life that aligns with thei...
Overcoming Fear: Helping Leaders Speak with Confidence In this episode of the Learnings and Missteps podcast, host Jesse interviews Jimmy Cannon, a voice and public speaking coach from the UK. Jimmy shares his journey from being a performer and singer to becoming a specialist in helping leaders speak without fear. The conversation covers the importance of energy, finding sincerity, and overcoming performance anxiety. Jimmy discusses his work with clients across various industries, helping th...
In this episode, Jesse welcomes Ms. Phyllis Winters, a seasoned expert with 30 years of experience across various industries like nuclear, healthcare, and construction. Phyllis discusses her journey from overcoming a challenging childhood to achieving significant milestones in the world of tech and business strategy. She emphasizes the importance of a problem-solving mindset and shares valuable insights on leveraging AI and technology for business growth. The episode covers practical tips for...
In this episode of the Learnings and Missteps podcast, host Jesse engages in a deep conversation with Mr. Jose Miguel Berlanga, an international entrepreneur with over 35 years of experience. Jose shares his journey from being a struggling student to becoming a successful real estate magnate and author. They discuss the importance of following one's interests, the harsh realities of entrepreneurship, the significance of continuous learning, and the unexpected link between economics and philo...
Ever found yourself asking too many questions or giving too many answers? You're not alone. This Solo-cast episode dives deep into the delicate balance leaders must strike between inquiry and instruction. At the heart of this episode is the "coaching scale" - a powerful framework for understanding when to ask open-ended questions and when to provide direct guidance. The key insight: your approach must match your team member's capability level. For those with high competence, questions like "...
What happens when you create a vision so clear that every decision becomes obvious? Joshua McMahon, owner of McMahon Custom Homes, reveals how he transformed from laborer to business owner by focusing relentlessly on his three-year vision. The entrepreneurial journey is rarely a straight path. Joshua candidly shares how he built his business foundation 18 months before leaving his secure job—posting consistently on social media, networking with key industry players, and sharing his vision re...
What drives someone to rise from mechanical trades to vice president multiple times? For Pansy Romo of InTech Mechanical, the answer lies not in credentials or connections, but in authentic servant leadership and an unwavering commitment to valuing people. This conversation delves into Pansy's remarkable journey—one that began without a college degree but flourished through intentional relationship-building and genuine appreciation for others. "When you invest in people and value them truly f...
Emotional intelligence pioneer Brent Darnell takes us through his remarkable 25-year journey transforming the construction industry's approach to people. With disarming honesty and profound insights, he reveals how human connection stands at the core of solving our industry's most pressing challenges—from mental health crises to workforce development struggles. "It goes beyond just being a better leader or a better manager of a construction process," Brent explains. "They become better human...
What happens when a talented estimator decides to break free from the confines of office life and build a business that serves multiple contractors while traveling the world? Jake Jones, co-founder of Archer Estimation and Consulting, shares his remarkable journey from geology student to nomadic entrepreneur in this thought-provoking conversation. Jake's natural talent for estimation was discovered almost by accident when his mentor reviewed a project budget he'd prepared and declared, "You'...
What happens when only one side builds a relationship? You end up with a lookout, not a bridge. This profound realization forms the heart of my conversation with Kimberly Sauceda, bestselling author of "Meet Me on the Bridge" and a relationship expert with over 20 years of experience working with organizations like Apple. Kimberly shares the touching origin story behind her bridge-building philosophy - a spontaneous moment with her teenage son during COVID lockdown that crystallized the trut...
Mario's journey from the soccer field to the construction site reveals profound leadership insights that transform how we think about success. Originally dreaming of becoming a doctor, his unexpected path to becoming a senior project manager with over 20 years of experience in the painting industry demonstrates how our greatest plans often give way to our greatest purpose. "The hardest person I had to deal with was myself," Mario confesses while sharing how internal battles with self-doubt n...
Dr. Carrie Graham brings over 25 years of expertise in adult workplace learning to this eye-opening conversation about why most corporate training fails to deliver meaningful results. With refreshing candor and profound insights, she challenges conventional approaches that prioritize content over people. "If you're not thinking about the people, what the hell are you doing?" This powerful question cuts to the heart of where training programs go wrong. Graham explains that organizations repea...
When Greg Crumpton pulls up his sleeve to reveal his Kaizen tattoo, you understand immediately this isn't just another trades professional – this is someone who has infused continuous improvement into every fiber of his being. The veteran HVAC expert, author, and industry advocate shares a career journey that spans from scribbling notes in a black book while running service calls in the 1980s to building and selling a successful mission-critical air conditioning company. His perspective cuts...
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