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The Thoughtful Entrepreneur

The Thoughtful Entrepreneur

By: Josh Elledge of UpMyInfluence.com
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You’re gonna love this DAILY, commercial-free entrepreneur spotlight show. We feature CEOs and founders of 6-9 figure B2B companies. Agencies, coaches, consultants, and other leaders share not only their success stories - but their advice for business leaders focused on business growth. You’re going to hear real stories from real people all in 15-25 minutes time - perfect for your commute. On this podcast, your host, Josh Elledge encourages entrepreneurs to share not only their expertise but their stories and their hearts. We believe that every person has a unique message which can positively impact the world. Even YOU! If you’d like to be featured on The Thoughtful Entrepreneur, apply here: https://UpMyInfluence.com/guest/https://upmyinfluence.com/privacy/ Economics Leadership Management Management & Leadership Marketing Marketing & Sales
Episodes
  • 2351 - Incorporating Joy and Humor into Your Leadership Style with Elizabeth Walker
    Dec 17 2025
    How Comedy Builds Trust, Connection, and Stronger Leadership Teams with Elizabeth Walker

    In this episode, host Josh Elledge speaks with Elizabeth Walker, host of the Dear Business Coach Podcast and a workplace communication expert who helps leaders use humor as a tool for connection and trust. Their conversation explores how comedy—when used intentionally—can break down barriers, improve communication, and create psychologically safe environments where teams thrive. This blog captures the most impactful insights from their discussion, offering leaders a fresh perspective on how humor can elevate leadership effectiveness and workplace culture.

    Using Humor as a Strategic Leadership Skill

    Elizabeth Walker reframes comedy as a leadership skill rather than entertainment, explaining that humor helps leaders communicate more effectively by making messages memorable and human. When leaders use light, intentional humor—especially through storytelling—they signal approachability and authenticity, making it easier for teams to engage, share ideas, and collaborate. Rather than relying on jokes, Elizabeth emphasizes humor rooted in shared experiences, everyday challenges, and honest reflection.

    A major focus of the conversation is self-effacing humor, which Elizabeth describes as a powerful way to build trust without undermining authority. By sharing moments of failure, awkwardness, or learning, leaders show they are human—inviting connection instead of hierarchy. Elizabeth cautions against self-disrespect, noting that effective self-effacing humor should create common ground rather than diminish confidence, helping teams feel safe enough to contribute openly.

    Elizabeth also shares how she teaches humor through workshops and exercises that guide participants to uncover their own “underdog stories.” These storytelling practices help individuals tap into authenticity, vulnerability, and relatability—key ingredients for strong leadership presence. By modeling openness and encouraging laughter rooted in empathy, leaders can foster cultures where trust grows, pressure eases, and teams become more resilient and engaged.


    About Elizabeth Walker

    Elizabeth Walker is a leadership communication coach, workshop facilitator, and host of the Dear Business Coach Podcast. She helps leaders, coaches, and teams use humor, storytelling, and authenticity to improve communication, build trust, and strengthen workplace culture. Connect with Elizabeth on LinkedIn or explore her work through the Dear Business Coach Podcast.


    About the Dear Business Coach Podcast

    The Dear Business Coach Podcast features conversations with coaches, leaders, and industry experts on practical strategies for professional growth, leadership development, and effective communication. The show focuses on real-world insights—covering everything from workplace dynamics to personal development tools leaders can apply immediately. Learn more at dearbusinesscoachpodcast.com.


    Links Mentioned in This Episode
    • Elizabeth Walker on LinkedIn
    • Dear Business Coach Podcast

    Key Episode Highlights
    • Comedy is a leadership tool—not entertainment
    • Humor improves communication...
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    14 mins
  • 2350 - Mastering Business Lessons from Pool Tables to Boardrooms with The Kronos Group's Jerry Brazie
    Dec 16 2025
    The Power of Peer-to-Peer Advisory Groups: How Jerry Brazie Helps Entrepreneurs Avoid Costly Mistakes

    In this episode, host Josh Elledge interviews Jerry Brazie, founder of The Kronos Group, to explore why entrepreneurship doesn’t have to be a lonely journey. Jerry shares how peer-to-peer advisory groups provide business owners with trusted insight, accountability, and real-world problem-solving that goes far beyond motivation or surface-level advice. Drawing from decades of experience building and advising companies, Jerry explains why consistent peer engagement can be the difference between costly mistakes and sustained growth.

    Why Peer-to-Peer Advisory Groups Create Stronger, Smarter Leaders

    Jerry Brazie compares entrepreneurship to mastering a skill like pool—progress doesn’t come from occasional participation, but from consistent, focused practice. In business, that consistency shows up through regularly meeting with peers who understand the pressure of leadership and growth. Advisory groups create an environment where business owners can openly discuss challenges, test ideas, and learn from others who have faced similar decisions, often preventing expensive missteps before they happen.

    A key distinction Jerry emphasizes is the difference between peer-to-peer advisory groups and traditional mastermind groups. While masterminds often focus on inspiration or high-level ideas, advisory groups are intentionally small and structured to deliver individualized feedback. Each member receives dedicated time to present real problems, receive candid input, and leave with clear next steps—turning discussion into execution rather than motivation without follow-through.

    Jerry also highlights the personal dimension of advisory groups, noting that leadership challenges rarely stop at the office door. Conversations often extend beyond operations and strategy into personal well-being, relationships, and balance. By addressing both business and life challenges, advisory groups help entrepreneurs make better decisions, stay grounded, and lead more sustainably over the long term.


    About Jerry Brazie

    Jerry Brazie is the founder of The Kronos Group, a peer-to-peer advisory organization serving business owners with revenues between $1M and $25M. With decades of experience building, scaling, and advising companies, Jerry is passionate about helping entrepreneurs avoid costly mistakes through accountability, candid feedback, and structured peer support. Connect with Jerry on LinkedIn.


    About The Kronos Group

    The Kronos Group (thekronosgroup.org) provides peer-to-peer advisory groups designed for growth-minded entrepreneurs. Through curated group experiences, monthly meetings, and one-on-one guidance, Kronos helps business owners gain clarity, improve decision-making, and accelerate growth while maintaining balance and perspective.


    Links Mentioned in This Episode
    • The Kronos Group Website
    • Jerry Brazie on LinkedIn

    Key Episode Highlights
    • Why entrepreneurship is often isolating—and how advisory groups solve that
    • The difference between peer-to-peer advisory groups and mastermind groups
    • How consistent participation drives better business decisions
    • Why accountability prevents costly mistakes as businesses scale
    • The value of...
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    17 mins
  • 2349 - ERP Solutions That Transform Heavy Equipment Dealerships with VitalEdge Technologies' Vikram Savkar
    Dec 15 2025
    How AI and Digital Transformation Are Reshaping Heavy Equipment Dealerships with Vikram Savkar

    In this episode, host Josh Elledge speaks with Vikram Savkar, CEO of VitalEdge Technologies, about how AI, ERP systems, and digital transformation are redefining heavy equipment dealerships across agriculture, construction, forestry, mining, and material handling. Vikram shares how industry-specific ERP platforms create operational leverage in a margin-sensitive environment and explains why incremental efficiency gains often produce the greatest competitive advantage. This blog captures the most important insights from their conversation, offering a clear roadmap for dealership leaders navigating modernization and AI adoption.

    Why Industry-Specific ERP and AI Matter in Heavy Equipment Dealerships

    Vikram explains that heavy equipment dealerships operate in a uniquely complex environment, where individual assets can cost hundreds of thousands—or even millions—of dollars and where service, inventory, finance, and field operations must function in perfect coordination. Generic ERP platforms often fall short because they are not built to handle equipment lifecycles, parts logistics, mobile technicians, or industry-specific workflows. Purpose-built ERP systems allow dealerships to gain visibility across operations, reduce inefficiencies, and make better decisions faster.

    Digital transformation, Vikram notes, is not about sweeping disruption but about stacking small operational improvements that compound over time. Faster service response, tighter inventory management, and improved procurement workflows can significantly impact cash flow and customer satisfaction. In industries where margins are tight, these “game-of-inches” improvements often determine long-term success.

    AI further accelerates this transformation by enabling predictive maintenance, smarter inventory forecasting, and deeper customer insights. Through VitalEdge AI Labs, Vikram and his team collaborate directly with dealers to prototype AI solutions that integrate seamlessly into real-world workflows. Rather than deploying AI for novelty, the focus remains on measurable outcomes—reduced downtime, improved uptime, and data-driven decision-making that scales with the business.


    About Vikram Savkar

    Vikram Savkar is the CEO of VitalEdge Technologies, where he leads innovation in ERP and AI solutions purpose-built for heavy equipment dealerships. With deep expertise in enterprise software and industry-specific transformation, Vikram focuses on helping dealers improve operational efficiency, embrace digital modernization, and gain sustainable competitive advantage. Connect with Vikram on LinkedIn.


    About VitalEdge Technologies

    VitalEdge Technologies provides industry-specific ERP solutions designed exclusively for heavy equipment dealerships across agriculture, construction, forestry, mining, and material handling. The platform integrates finance, inventory, service, CRM, mobile field operations, business intelligence, and AI-driven insights into a unified system. Learn more at vitaledge.com.


    Links Mentioned in This Episode
    • VitalEdge Technologies Website
    • Vikram Savkar on LinkedIn

    Key Episode Highlights
    • Why heavy equipment dealerships require industry-specific ERP systems
    • How...
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    18 mins
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