Bourbon in the Boardroom

William Hagood
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Bourbon in the Boardroom is where real leadership gets talked about the way it actually happens—unfiltered, under pressure, and without the corporate script. This isn’t about titles or positions. It’s about what actually makes leaders successful—the experiences that shaped them, the mentors who challenged them, the relationships that grounded them, and the moments that defined how they lead. This isn’t theory. It’s not polished soundbites. It’s the kind of conversation leaders have when the stakes are real, the decisions matter, and the room gets quiet. From strategy to execution, from wins to hard lessons—nothing’s off the table. We may not be your cup of tea… but we might be your shot of whiskey.

Episodes

  1. Nov 4

    Two William's One Boardroom

    Two Williams, One Boardroom | William T. Olsen III It’s a first for Bourbon in the Boardroom: two Williams in one room. I’ve already conceded. He’s got “the Third” on his name. I’ve just got a podcast. William T. Olsen III leads complex federal construction, infrastructure, and mission-critical programs, where every step is regulated and every mistake is expensive. He has overseen multi-million-dollar portfolios for federal agencies, built high-performing teams from the ground up, and has a habit of turning chaos into systems that actually work. In this episode, we get into: 🥃 How to keep big projects on track when the oversight never stops 🥃 Turning messy operations into standards, structure, and accountability 🥃 Building cultures where accountability and trust work together instead of against each other 🥃 Why leaving people, projects, and communities better than you found them is a leadership philosophy, not just a construction one Whether you run projects, lead a team, or are trying to scale without losing control, pour something good and pull up a chair. 🥃 Subscribe so you never miss a pour 📩 Join The Pour newsletter: https://bourbonintheboardroom.com/landing 🛒 Shop The Pour store: https://thepour.bourbonintheboardroom.com 🌐 https://bourbonintheboardroom.com #BourbonInTheBoardroom #Leadership #ExecutiveLeadership #Construction #OperationalExcellence

  2. Oct 21

    Get punched in the face and be happy with it....Caleb Johnson

    The biggest mistake new investors make is thinking safety comes from a W-2. Caleb Johnson learned the hard way that real security comes from ownership, financial literacy, and buying when everyone else is scared.At 28, Caleb is already building a real estate engine that spans acquisitions, property management, and resident education. As founder of Red Sea Capital and co-founder of Arkstone Property Management, he breaks down how he scaled into commercial multifamily, why he targets distressed assets in Phoenix, and why he believes softening rents can create the best buying opportunities.You’ll discover:How a single family story shaped his entire investing philosophyThe house-hacking strategy that launched him into real estateWhy vertical integration matters when you own and manage your own assetsThe GP vs LP difference explained simply, without the jargonHow he thinks about market diversity, data centers, and avoiding overconcentration in one industryThe leadership lesson that cost him money, but protected his investorsWhy he teaches residents basic financial literacy, from debt to credit to savingsWilliam Hagood pushes Caleb into the real numbers and the real pressure behind scaling apartment deals, including a 14-unit bank-owned turnaround in South Phoenix, a 16-unit Oklahoma City lesson that exposed hidden plumbing risk, and the mindset required to keep going when the stakes get personal.Caleb also shares the mentor who changed his path, the role faith plays in how he leads, and the simple truth that separates people who dream about investing from people who actually do it: action.Essential listening if you want to understand multifamily investing, leadership under pressure, and what it really takes to build wealth from the ground up.

  3. Oct 7

    Curiosity in leadership...Dani Chou

    Curiosity in Leadership - What if curiosity could help us lead with more empathy, connect more deeply, and become better humans? In this episode, William Hagood welcomes Dani Raschel Chou for an open, thoughtful conversation about leadership, career growth, and the power of genuine connection.Dani brings a wealth of knowledge and shares it generously—from her experience in city planning and executive support to her work as a consultant, podcaster, writer, and endurance athlete. Along the way, she opens up about the pressures leaders face, the quiet weight of confidential work, and the challenges of building friendships and community as adults.Together, William and Dani explore why networking is about more than exchanging job titles. Finding people through shared interests, building a trusted circle, and staying curious about perspectives different from our own can help us feel less alone and communicate with greater understanding.They also discuss the power and pitfalls of “what if” thinking, learning through failure, hiring the person rather than the paper, and asking difficult questions in ways that invite people to open up instead of shutting down.If you’re looking for an honest conversation about leadership, curiosity, and creating more meaningful connections, this episode is for you. https://www.youtube.com/@withhatandcattle https://www.youtube.com/@casachoupoms https://www.linkedin.com/company/withhatandcattle/ https://www.linkedin.com/in/daniraschel/ Music licensed through Soundstripe. Code: LVTB98BU9MXGZDWT

  4. Sep 23

    Don't go cheap on things that connect you to the ground! - Chad King

    Most companies think they need to buy more software. Chad King is betting they need to rent the right one instead.He joins Bourbon in the Boardroom to break down a model that’s helping businesses scale without adding headcount, slash waste in disconnected systems, and turn custom software from a half-million-dollar CapEx headache into an affordable monthly OpEx. William Hagood and Chad also dig into the leadership lessons behind the work—from Marine Corps discipline and mission focus to the hard calls around protecting your team, trusting people quickly, and knowing when to pivot before a bad decision becomes a costly one. You’ll discover: Why Chad says the best leaders are often forged by bad leadershipHow he quantifies the cost of broken systems down to the dollarWhy “the right person for the job” matters more than a perfect résuméHow trust is built by giving responsibility early, not hiding itThe real reason some companies refuse to cut corners, even when it costs them deals Along the way, they get into bourbon, barbecue, and the patience it takes to do either well. Chad shares the bottles he reaches for, why William LaRue Weller sits at the top of his collection, and what whiskey has to teach leaders about timing, process, and waiting for the right result. He also drops a line that’s worth remembering: don’t go cheap on the things that connect you to the ground—shoes, tires, and even your mattress. If you’re a founder, operator, or team leader trying to build something durable, this conversation is packed with practical leadership, sharp business instincts, and a few great pours along the way. Chad King is one of the masters behind Ayoka Systems, a custom software company helping businesses scale with tailored, modular solutions. Known for blending technology, sales, and leadership, he brings a rare perspective from the Marine Corps, corporate America, and the small-business world. Perfect for leaders who care about team culture, operational efficiency, and making smarter decisions before the cracks show.

  5. Sep 3

    I am stubborn, but now I realize it..Addison Hagood

    This episode took a hard left turn — in the best way. I brought my daughter onto the show to talk leadership, legacy, and… how to properly cook bacon. She's a student at Tarrant County College headed to UNT next year, aiming to become a teacher (with a marketing backup plan, because she's smart enough to have one). She's stubborn, sharp, and fully convinced she's the funniest person in the room, and honestly, she thinks I never give her enough credit for it. Still figuring out exactly how she's going to shake up the world, but I'd bet money she does. This one's less "boardroom strategy" and more "kitchen table wisdom," and honestly? It might be my favorite episode yet. Music licensed through Soundstripe. Code: LVTB98BU9MXGZDWT

  6. Aug 19

    Great leadership isn’t about having all the answers...Brandon Denmon

    Keep Climbing Great leadership isn’t about having all the answers — it’s about building a culture where people feel seen, supported, and aligned toward something bigger. Brandon Denmon shares why culture drives execution, how hard decisions shape strong teams, and why the best leaders help others reach the summit. You can find Brandon Denmon all of the DFW metro as well as here: youtube.com/@BrandonDenmon https://www.linkedin.com/in/brandon-denmon-b496bb6a/ https://peakexecutivesolutions.com bdenmon@peakexecutivesolutions.com #Leadership #Culture #ExecutiveLeadership #ServantLeadership #BusinessGrowth #Teamwork #LeadershipDevelopment #PeakExecutiveSolutions #BourbonAndTheBoardroom Music licensed through Soundstripe. Code: LVTB98BU9MXGZDWT

  7. Aug 5

    Making it fun is where the magic is...Tyler White

    Tyler White is Senior Recruiting Director at Coda Search and Staffing, VP at CISO Ascent and CIO Ascent — where he gets CIOs and CISOs out of the boardroom and onto a trail in a National Park — and co-host of his own podcast, Timeout with Leaders. Recruiter, community builder, podcaster — same guy, same gift. Let's pour one and get into it." https://www.linkedin.com/in/woopigtylerwhite/ https://codarecruitment.com/ https://cisoascent.com/ https://cioascent.com/ https://www.youtube.com/@timeoutwithleaders8635 Music licensed through Soundstripe. Code: LVTB98BU9MXGZDWT

  • 7 Episodes

About

Bourbon in the Boardroom is where real leadership gets talked about the way it actually happens—unfiltered, under pressure, and without the corporate script. This isn’t about titles or positions. It’s about what actually makes leaders successful—the experiences that shaped them, the mentors who challenged them, the relationships that grounded them, and the moments that defined how they lead. This isn’t theory. It’s not polished soundbites. It’s the kind of conversation leaders have when the stakes are real, the decisions matter, and the room gets quiet. From strategy to execution, from wins to hard lessons—nothing’s off the table. We may not be your cup of tea… but we might be your shot of whiskey.

Information

  • Creator
    William Hagood
  • Years Active
    2026
  • Episodes
    7
  • Rating
    Explicit
  • Copyright
    © 2026 William Hagood
  • Show Website
    Bourbon in the Boardroom