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Learnings and Missteps

Learnings and Missteps

By: Jesse
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About this listen

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.

© 2025 Learnings and Missteps
Economics Leadership Management & Leadership Personal Development Personal Success
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Episodes
  • Adventures in Estimation: How Jake Jones Transformed His Career
    May 15 2025

    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're in the wrong job." What followed was a career transformation that led him through various companies where he consistently found ways to optimize estimation processes, turning handwritten takeoffs into sophisticated spreadsheet systems. One simple macro he developed saved his company approximately 40 man-hours annually – exemplifying his philosophy that small improvements can yield significant results.

    The pandemic proved to be a turning point for Jake when he discovered he could be even more productive working remotely. When faced with ultimatums to return to the office, he made the bold decision to launch his own fractional estimating business. Now, he helps contractors who need estimation expertise but can't afford full-time specialists while enjoying the freedom to work from anywhere. Currently based in Santiago, Chile, with previous stops in Argentina and Uruguay, Jake and his wife have embraced minimalism, paring down their possessions to just a few suitcases.

    For those considering a similar path, Jake offers practical advice about the realities of entrepreneurship, emphasizing the importance of understanding business fundamentals and building strong support networks. His story demonstrates how specialized expertise combined with process optimization can create opportunities for both professional fulfillment and personal freedom.

    Whether you're a contractor seeking to improve your bidding processes or someone dreaming of location independence, Jake's experiences provide valuable insights into building a business that serves others while supporting the lifestyle you desire. What small improvements could transform your workflow and open new possibilities in your career?

    Jakes Jones:

    http://www.archerestimation.com/

    mailto:info@archerestimation.com

    https://www.linkedin.com/in/jake-j-73ba2516

    Make yourself a priority and get more done: https://www.depthbuilder.com/do-the-damn-thing

    Download a PDF copy of Becoming the Promise You are Intended to Be
    https://www.depthbuilder.com/books

    Show More Show Less
    1 hr and 3 mins
  • Building Bridges, Not Walls: Kimberly Sauceda on Connection and Leadership
    May 8 2025

    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 at 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 truth about mutual relationship investment. "Hi mama, I'm here to build a bridge," he said, mirroring her own approach and revealing the essential nature of two-sided connection.

    We explore how leaders unknowingly "pluck the feathers of eagles," transforming potential high-performers into disengaged team members through dismissive behaviors and unclear expectations. As Kimberly wisely notes, "unset expectations are predetermined disappointment." The bridge metaphor extends beyond the workplace into all human connections, offering a framework built on trust, respect, and genuine interest in others.

    The conversation takes a fascinating turn when we discuss conflict's crucial role in relationship building. Rather than viewing conflict as something to avoid, Kimberly reframes it as an opportunity to strengthen connections through curiosity and listening. High-trust teams are five times more productive precisely because they can navigate disagreement effectively.

    For those working under limiting leadership, Kimberly offers practical strategies: decide who you want to be regardless of circumstances, find alternative sources for validation, and develop a personal "board of directors" for perspective and support. This approach maintains integrity while strategically working toward roles where your contributions are valued.

    Ready to transform your professional and personal relationships? Start by asking yourself which bridges you're building and whether you're inviting others to build alongside you. Check out Kimberly's book and leadership programs at fromO2U.com to learn how to move from overwhelmed to unstoppable through the power of connection.

    Connect with Kimberly at:

    https://fromo2u.com/

    https://www.linkedin.com/in/kimberlysauceda/

    Make yourself a priority and get more done: https://www.depthbuilder.com/do-the-damn-thing

    Download a PDF copy of Becoming the Promise You are Intended to Be
    https://www.depthbuilder.com/books

    Show More Show Less
    1 hr and 10 mins
  • Mario Acosta on Mindset, Teamwork, and Trust: The Building Blocks of Champions
    Apr 16 2025

    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 nearly derailed his career. His vulnerability creates an immediate connection with anyone who's ever questioned their place in their profession. Mario's guidance on building championship teams—whether on construction projects or soccer fields—centers on trust as the non-negotiable foundation. "When you have a strong team that works as a unit, you can trust each other and not worry about checking their work all the time."

    The conversation takes a powerful turn when Mario addresses the rarely discussed isolation that comes with advancement. "The higher you move up, the lonelier you're going to be," he explains, detailing how leadership positions often mean fewer peers, less positive feedback, and increased pressure. His advice to have honest conversations with family about the sacrifices required for career growth comes from painful personal experience, offering listeners wisdom that could save relationships while pursuing professional goals.

    What separates this leadership conversation from countless others is Mario's focus on practical application rather than theoretical concepts. From eliminating "I" from your vocabulary to encouraging team problem-solving without dictating methods, his approach transforms leadership from a position of authority to one of service. Listen now to discover how to build your own championship team and leave a lasting impact through sharing your wisdom with others who follow in your footsteps.

    Connect with Mario at: https://www.linkedin.com/in/mario-acosta-36281a286/

    Make yourself a priority and get more done: https://www.depthbuilder.com/do-the-damn-thing

    Download a PDF copy of Becoming the Promise You are Intended to Be
    https://www.depthbuilder.com/books

    Show More Show Less
    1 hr and 5 mins

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