Learnings and Missteps by Depth Builder

Jesse
  • 5.0 (19)
  • Self-Improvement
  • Updated Biweekly

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 path to Becoming the Promise You are Intended to Be.Through these interviews you will learn about the buttons you can push to be a better leader, carve your own path, and build your influence. Find yourself in their stories and know that your path is still ahead of you.

  1. 3d ago

    Construction Leadership Lab: The Room Where the Real Talk Happens

    Leadership in construction is lonely. The 2 a.m. gut-check calls. The mistakes nobody at the office needs to know about. The moments where "fake it till you make it" stops working and you just need someone who gets it. This episode, Jesse opens the door to something new: the Construction Leadership Lab: a peer community built for leaders who are done pretending they have it all figured out. This isn't a networking group. It isn't a highlight reel. It's a room for GCs, subs, owners reps, coaches, and service providers across the U.S. and Canada who are ready to trade the polished version of leadership for the real one. What's inside: Monthly live calls — recorded and shared as a members-only podcast, so nobody misses a sessionFishbowl coaching — bring real problems, get real input, leave with a real commitmentBook study — one book every three months, discussed as a group, not just read aloneSelfish Servant Cheat Sheets — a weekly newsletter built to make leadership stickThe Vault — templates and checklists ready to use on the job, not just in theoryThree rules keep the room honest: be generous, be fearless, be cool. Ask how people want to be treated. Be more interested than interesting. Know when to pass the mic. If leadership in construction has ever cost you sleep, this is the group built for that. Listen now. Then go save your seat in the Lab. 00:00 Leadership Is Human 00:20 Why Leaders Need Support 01:52 Introducing The Lab 02:50 Core Features Overview 04:52 Calls Schedule and Focus 05:09 Book Study Deep Dives 08:12 Fishbowl Problem Solving 11:07 Commitments and Accountability 13:05 Weekly Newsletter Value 13:46 Content Vault Resources 15:17 Mission and Purpose 16:17 Community Guidelines 21:53 Join or Keep Listening Lets leave the Construction Industry Better than We Found It https://www.depthbuilder.com/construction-leadership-lab Download the free PDF copy of Becoming the Promise You are Intended to Be

    Construction Leadership Lab: The Room Where the Real Talk Happens

  2. Jul 30

    Why "Pass/Fail" Thinking Is Killing Your Momentum

    Ever quit on a goal the moment it stopped feeling like a win? This week's episode breaks down why treating progress as pass/fail is the quiet reason so many goals stall out before they get traction. He unpacks the start-stop cycle: new goals always run into friction from commitments you already have, and pass/fail thinking punishes you for that friction instead of accounting for it. Using fitness as the example, Jesse shows how to build momentum differently, going from zero to one, chaining back-to-back reps, hitting a three-time streak, and only then raising the bar. Small wins aren't consolation prizes. They're the mechanism. Next Jesse introduces "bookends": instead of judging a goal week to week, you set a real time horizon and a single checkpoint down the road; like committing to a podcast for 12 months no matter what the download numbers say early on. That container is what lets you actually learn, build relationships, and stumble into upside you couldn't have planned for (Jesse points to finding his own voice as one example). Lastly, Jesse closes on why this matters beyond the goal itself, framing success not around hitting a number, but around impact, using his own book as the example: if it helps even one person, it did its job. 00:00 Escape Win Lose Thinking 03:04 Celebrate Zero to One 06:07 Back to Back and Streaks 10:01 Feedback Loops Beat Perfection 12:20 Shift Two Bookends 15:54 Podcast Bookend Example 18:51 Discovering Your Voice 20:58 Impact Based Goals 23:05 Book Link and Share It 24:19 Wrap Up and Next Steps Lets leave the Construction Industry Better than We Found It https://www.depthbuilder.com/construction-leadership-lab Download the free PDF copy of Becoming the Promise You are Intended to Be

    Why "Pass/Fail" Thinking Is Killing Your Momentum

  3. Jul 23

    The Real Reason Construction Tech Dies in the Field with AJ Waters

    AJ Waters wanted to design stadiums. Instead, he ended up rebuilding the operating system for one of the largest construction companies in the world and learning, the hard way, why so many digital transformations quietly collapse in the field. In this episode, AJ takes Jesse inside the messy reality of tech adoption at scale: what it was really like leading a major platform overhaul at Kiewit, why executives sometimes override the "right" decision for reasons that have nothing to do with the data, and the uncomfortable truth about who construction software has historically been built for and who's been left out. They also get into: Why teams keep optimizing for the back office while the people actually swinging hammers get ignoredWhat evaluating project management platforms for Google's data center builds taught AJ about alignment vs. politicsThe surprising throughline between his childhood Lego obsession and how he approaches problem-solving todayWhy AJ started The Engineered Life to talk about "superpowers" most people don't even know they haveIf you've ever wondered why the tools that look perfect in a boardroom fall apart on-site, or why subcontractors always seem to get the short end of the software stick, this one's for you. By the end, you'll understand why AJ measures success by one simple standard: whether he left people, and situations, better than he found them. 00:00 Executive Override Reality 00:18 Meet AJ Waters 02:00 Lego Builds and Movie Nerd 03:23 Rebuilding Memorial Stadium 05:38 Dreaming of Stadiums 08:31 Not Smart Enough to Engineer 11:01 Design vs Construction Life 11:23 LnM Listener Shoutout 13:55 Why Construction Fits People 17:48 First Digital Takeoff Win 20:16 Resourcefulness and Problem Solving 25:17 iPhone Sparked Tech Interest 27:56 Volunteering for Transformation 29:48 Change Resistance on Site 31:32 Design for Field Users 33:20 Workarounds and Training Gaps 34:58 From Internal Tools to Innate 35:50 Owner Side Lessons at Google 40:07 Systems vs Human Behavior 42:50 Procore vs PlanGrid Politics 44:50 Tech Ignores Subs and Owners 46:27 AI and Platform Advantage 51:15 EngiNerd Life Origin Story Lets leave the Construction Industry Better than We Found It https://www.depthbuilder.com/construction-leadership-lab Download the free PDF copy of Becoming the Promise You are Intended to Be

    The Real Reason Construction Tech Dies in the Field with AJ Waters

  4. Jul 16

    Too Much for Some, Just Right for Others: Amy Cordero-Houk on Being Authentic, Unapologetic, and Done with Chasing Everyone's Approval

    There's a version of "authentic" that's just an excuse to be obnoxious. Amy Houk isn't that version. Amy is the president of National Lien Services and RSC Preliminary Lien Services and joins Jesse to talk about turning 50 and how that moment changed everything: she stopped caring about most things and started caring a lot more about the things that mattered. She gets real about the line between authenticity and being difficult, why she owns her role in conflict instead of playing the victim, and the apology she almost didn't give (but did).  They also dig into saying the quiet part out loud, why boundaries beat manipulation every time, and how to spot a narcissistic dynamic before it costs you. Then Amy pulls back the curtain on the side of construction most people ignore until it's too late — protecting your payments and mitigating risk before a project turns into a collections nightmare. Listen now, and find Amy online for more on risk, contracts, and getting paid what you're owed. https://www.linkedin.com/in/amyhouk/    00:00 Not Too Much 00:18 Meet Amy Houck 02:59 Desert Whales Icebreaker 04:49 Writing Like Yourself 06:23 Authenticity As Brand 09:20 Finding Courage At Fifty 09:54 Mom The Powerhouse 12:19 Shout Out Segment 13:13 Authentic Not Obnoxious 18:01 Men Versus Boys 18:19 Gen X Follow Up Email 22:24 Truth With Kindness 25:16 Narcissism Talk 29:41 What Lien Services Do 32:31 Leading By Educating 34:32 Monthly Live Webinars 35:24 Respecting Construction Risk 37:37 Ranch Roots Work Ethic 39:07 Service Driven Leadership 42:10 Authenticity And Influence 45:02 Posers And Being Enough 47:37 Honesty With Responsibility 49:06 Narcissist Fallout Lesson 53:29 How To Start Authentic 58:31 Promise To Stay Open 01:02:32 Where To Find Amy Lets leave the Construction Industry Better than We Found It https://www.depthbuilder.com/construction-leadership-lab Download the free PDF copy of Becoming the Promise You are Intended to Be

    Too Much for Some, Just Right for Others: Amy Cordero-Houk on Being Authentic, Unapologetic, and Done with Chasing Everyone's Approval

  5. Jul 9

    Stop Giving Feedback - Have this Conversation Instead

    Feedback is optional. Performance isn't. Most managers default to soft, vague feedback, the "poo-poo sandwich" of compliment, critique, compliment, because it feels safe. But feedback is suggestive by nature, appropriate for social settings or volunteer environments where the stakes are low. Performance conversations are different. They require clarity, accountability, and follow-through. This episode breaks down a 3-part framework for having real performance conversations: Anchor language — Use words that stick: if there is a failure, or expectations not met. Vague language gets forgotten. Anchor language gets remembered.Explicit consequences — Name what happens next: reassignment, termination. Ambiguity protects no one.Resources and support — Pair the hard conversation with a real path forward: tools, check-ins, and support to close the gap.Two examples bring the framework to life: a 90-day team member and a third-year apprentice, both of whom turned performance around after clear expectations, defined tool requirements, weekly check-ins, and stated consequences were put on the table. The result isn't a harder conversation; it's a clearer one. And clarity is what actually changes behavior. Lets leave the Construction Industry Better than We Found It https://www.depthbuilder.com/construction-leadership-lab Download the free PDF copy of Becoming the Promise You are Intended to Be

    Stop Giving Feedback - Have this Conversation Instead

  6. Jul 2

    No Excuses, No Victims: Bradley Henderson on Radical Ownership and Closing the Divide

    Bradley Henderson built a company that bridges the field-office gap in construction, but the story of how he got there is the one worth hearing. Plumb Line Operations founder and field worker advocate Bradley Henderson joins Jesse to talk about the personal cost of traveling construction work, what addiction and prison taught him about radical ownership, and why he now builds a "second chance" lane connecting skilled workers with structured employers. Jesse opens up about his own 10 years of sobriety as the two get honest about the long road from victim mentality to accountability and what it really looks like to make amends and turn your worst chapter into your purpose. 00:00 Turning Pain Into Magic 00:14 Meet Bradley Henderson 01:34 The Toll of Travel Work 04:31 LinkedIn Style and Accountability 05:37 Addiction Prison and Ownership 07:52 Sobriety and Compounding Change 11:47 Shoutout and Viktor Frankl Lesson 14:14 Owning Mistakes in the Field 16:04 Rebuilding After a Record 19:49 From Manipulation to Influence 22:02 Rehab Story and Shame Release 24:28 Sharing the Shame 24:52 Why the Rooms Work 26:30 Turning Pain Into Help 27:27 Owing It Forward 28:57 Making Amends for Real 35:03 Gratitude and Second Chances 36:42 Building a Coaching Calling 38:02 Second Chance Workforce Plan Lets leave the Construction Industry Better than We Found It https://www.depthbuilder.com/construction-leadership-lab Download the free PDF copy of Becoming the Promise You are Intended to Be

    No Excuses, No Victims: Bradley Henderson on Radical Ownership and Closing the Divide

  7. Jun 25

    Accountability, Vulnerability, and Culture Change in Construction with Coralee Beatty

    Most construction leaders think they have an accountability problem. What they actually have is a clarity problem, and they're pointing the finger in the wrong direction. Coralee Beatty, founder of Thrive HQ and one of the most honest voices in the construction leadership space, joins Jesse to get into the real reasons teams underperform, people quit, and culture stays stuck. From her point of view the fix is simpler (and harder) than most leaders want to admit. In this episode, Coralee reframes accountability entirely, it's not a hammer, it's a scaffold. Real accountability means your people have what they need to succeed, and they know it's still on them to show up. When those two things are true at the same time, everything changes. They get into why so many construction leaders default to blaming the crew when the real gap is in how roles, expectations, and commitments were set up in the first place. If your team doesn't know exactly what "good" looks like, you don't have an accountability problem, you have a leadership gap. Coralee also talks about what it actually took to exit a business she built, the childhood abandonment that wired her to fear judgment and chase "good enough," and how she turned that into fuel. She doesn't dress it up. That's what makes it land. And she makes the case that vulnerability isn't soft, it's a jobsite skill. When leaders show up honestly, teams feel safe enough to do the same. That's where trust actually gets built. If your retention is struggling, your culture feels flat, or you're tired of having the same performance conversations with no real change, this episode is worth your full attention. 00:00 Why Accountability Matters 00:50 Meet Coralie Beatty 02:13 Clubhouse Community Era 04:07 Defining Accountability 05:42 Commitment Versus Control 10:06 Listener Shoutout Break 11:05 Building Accountable Teams 14:40 Leadership And The Denominator 16:16 No Master Plan Just Iteration 18:22 Resilience And Fear Of Judgment 22:05 Roots Of Not Enough 26:29 Sharing Lived Experience 27:54 Changing Minds Online 29:19 Construction Culture Shift 30:00 Appreciation Wins Talent 31:00 Acknowledgment Changes Everything 34:00 From Hardass to Human 36:32 Who Gets to Help 39:35 Vulnerability Builds Trust 47:39 Simple Culture Fixes 51:58 Connection Is the Cure Lets leave the Construction Industry Better than We Found It https://www.depthbuilder.com/construction-leadership-lab Download the free PDF copy of Becoming the Promise You are Intended to Be

    Accountability, Vulnerability, and Culture Change in Construction with Coralee Beatty

  8. Jun 18

    Become Your Best Advocate: Do an Inventory and Get Clear on Expectations

    Every time you say yes to avoid discomfort, you're saying no to yourself. Over time, that trade leads straight to burnout — and to showing up for everyone else at a fraction of your capacity. In this episode, Jesse breaks down two foundational steps to stop operating on everyone else's terms and start advocating for yourself for real. What you'll hear: Step 1 — Do an inventory. Jesse walks you through a simple two-column exercise: what you do because you want to, versus what you do because someone else wants or expects it. Most people who do this exercise are surprised by what they find; over-delivering for others while their own wellness, growth, health, and relationships sit at the bottom of the list. This inventory tells you exactly where boundaries are needed and who actually values your time. Step 2 — Get clear on whose expectations you're actually living by. Here's the thing: most of the expectations running your life were never explicitly stated. They're assumed. Jesse shares real career examples of paths he walked away from like project management and corporate roles, once he got honest about what he actually valued. He also addresses the reality check: if someone's paying your bills, some expectations are non-negotiable. Knowing the difference is the whole game. If you've been feeling stretched thin, resentful, or like you're constantly serving everyone but yourself, this episode is a direct answer to why. 00:00 Stop Saying Yes 00:42 Two Advocacy Steps 01:45 Do An Inventory 02:53 Two Column Exercise 05:02 Reality Check Results 06:14 Friend Favor Trap 08:11 Boundaries And Progress 09:46 From Salty To Clarity 14:27 Get Clear On Expectations 17:56 Career Path Wake Up 19:35 Choosing Your Own Path 21:51 Balancing Life Priorities 28:18 Invest In Internal Teams 29:31 Quick Summary And Goodbye Lets leave the Construction Industry Better than We Found It https://www.depthbuilder.com/construction-leadership-lab Download the free PDF copy of Becoming the Promise You are Intended to Be

    Become Your Best Advocate: Do an Inventory and Get Clear on Expectations
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About

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 path to Becoming the Promise You are Intended to Be.Through these interviews you will learn about the buttons you can push to be a better leader, carve your own path, and build your influence. Find yourself in their stories and know that your path is still ahead of you.

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