Unconventional Wisdom About Conventional Wisdom

Kim Miller - Hershon
  • 5.0 (4)
  • ENTREPRENEURSHIP

Unconventional Wisdom About Conventional Wisdom: Where clichés come to retire and fresh thinking we inspire. Smart minds don’t think alike—and that’s the point. Unconventional Wisdom About Conventional Wisdom takes you inside the messy, brilliant, and bold thought processes of high-achieving leaders, entrepreneurs, and out-of-the-box thinkers. We skip the clichés and spotlight the real talk: the strange decisions that worked, the brilliant ideas that bombed, and the thought patterns that defy the rulebook—but still lead to growth, impact, and the occasional mic drop. If you’re tired of surface-level advice and crave the kind of wisdom that makes you pause, laugh, and level up—this is your new favorite listen. Because let’s face it: playing it safe never built anything worth bragging about.

  1. 6H AGO

    Stop “Shoulding” on Yourself Webinar: 3 Leadership Decisions That Create More Revenue and Less Overwhelm

    Leadership doesn’t have to mean carrying everything alone. If your business is growing, but somehow everything still lands back on your desk, it may not be a time management issue — it may be the decisions shaping your leadership. Join my FREE live webinar where I’ll walk you through 3 key decisions that help leaders increase revenue without adding more hours to their schedule. 👉 Save your spot here: https://webinar.kimmillerhershon.com Stop being the bottleneck. Start leading with more clarity, focus, and freedom. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

    6 min
  2. Breaking the Rules of Leadership: Authenticity, Confidence & Challenging Convention with Patrick McCann

    7H AGO

    Breaking the Rules of Leadership: Authenticity, Confidence & Challenging Convention with Patrick McCann

    In this episode of Unconventional Wisdom About Conventional Wisdom, Kim Miller-Hershon sits down with Patrick McCann — Chief Executive of the City of London Law Society, co-founder of multiple legal diversity initiatives, former Director of Learning at Linklaters, and one of the most visible LGBTQ+ voices in the UK legal sector. Patrick brings an energizing, deeply human perspective to leadership, challenging the rigid conventions often embedded in traditional industries like law. From his early career as a lawyer navigating hierarchical systems that rewarded conformity, to simultaneously teaching aerobics classes for over two decades, Patrick shares how breaking rules, embracing individuality, and prioritizing people over positional power shaped his unconventional path. This conversation explores what leadership really looks like beyond titles, status, and traditional authority. Patrick opens up about navigating anxiety, late-diagnosed ADHD, imposter syndrome (or as he calls it, becoming an “imposter”), and the ways leaders can create environments where people actually feel seen, supported, and able to thrive. Beyond leadership, this episode dives into identity, self-awareness, inclusion, and why the most impactful leaders are often the ones willing to challenge outdated systems while staying grounded in kindness and authenticity.   We explore: - Why “follow the rules” can be some of the worst career advice you ever receive - Patrick’s unexpected journey from lawyer to sought-after aerobics instructor - The hidden class systems and hierarchies inside elite professional environments - Why great leaders focus more on people than titles, profits, or ego - The importance of recognizing and calling out people’s strengths specifically - How anxiety, ADHD, and losing things became part of Patrick’s leadership self-awareness - Why self-doubt can become self-indulgent if left unchecked Patrick’s perspective is a reminder that leadership isn’t about becoming more polished, more hierarchical, or more intimidating — it’s about becoming more yourself, more intentional, and more committed to helping others grow. If you’ve ever questioned traditional leadership models, struggled with self-doubt, or wondered how to succeed without sacrificing authenticity, this episode will leave you both inspired and rethinking what effective leadership actually looks like. Connect with me here: Website: https://www.kimmillerhershon.com LinkedIn: https://www.linkedin.com/in/kmillerhershon Newsletter: https://link.kimmillerhershon.com/widget/form/aEdmdA1W5MhoMCMfy5O8 Webinar: https://webinar.kimmillerhershon.com/?utm_source=Podcast Guest Details: Organization: City of London Law Society LinkedIn: https://www.linkedin.com/in/patrick-mccann-066017207/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

    38 min

  3. 2D AGO

    Stop “Shoulding” on Yourself Webinar: 3 Leadership Decisions That Create More Revenue and Less Overwhelm

    Leadership doesn’t have to mean carrying everything alone. If your business is growing, but somehow everything still lands back on your desk, it may not be a time management issue — it may be the decisions shaping your leadership. Join my FREE live webinar where I’ll walk you through 3 key decisions that help leaders increase revenue without adding more hours to their schedule. 👉 Save your spot here: https://webinar.kimmillerhershon.com Stop being the bottleneck. Start leading with more clarity, focus, and freedom. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

    6 min
  4. The Leadership Lie Everyone Believes: Why Being Authentic Isn’t Enough

    3D AGO

    The Leadership Lie Everyone Believes: Why Being Authentic Isn’t Enough

    In this episode of Unconventional Wisdom About Conventional Wisdom, Kim Miller-Hershon sits down with Nick Jain — co-founder of Eagle Rock CFO Services, Harvard Business School graduate, former professional investor, and finance leader who has helped scale businesses across trucking, software, and e-commerce to over $100M in revenue. Nick brings a refreshingly analytical and unconventional perspective to leadership, challenging many of the “feel-good” business rules people are often taught early in their careers. From questioning the popular advice to simply “be yourself” as a leader, to explaining why successful businesses should be built through small experiments instead of big all-or-nothing bets, Nick shares practical lessons shaped by years of experience leading finance and operations teams. This conversation dives into the realities of leadership, decision-making, entrepreneurship, and what it looks like to build an AI-native consulting business from the ground up. Nick also opens up about the challenges of sticking to decisions, managing uncertainty, navigating partnership dynamics, and why leadership is often less glamorous and far more methodical than popular culture suggests. Beyond business strategy, Nick shares his thoughts on AI, entrepreneurship, and how math, experimentation, and calm decision-making shape both his work and mindset. We explore: Why the advice to “just be yourself” can actually hurt aspiring leaders Why successful leaders are often more analytical than charismatic The struggle of sticking with decisions after they’ve been made How Nick and his co-founder are building an AI-native advisory firm Why smaller, highly efficient businesses may outperform traditional large firms The realities of co-founder communication, role clarity, and partnership agreements Nick’s perspective is a reminder that leadership isn’t always about confidence, charisma, or bold speeches — often, it’s about clear thinking, thoughtful experimentation, and building systems that let businesses grow smarter. If you’ve ever questioned traditional leadership advice or wondered what modern entrepreneurship really looks like in the AI era, this episode will give you a lot to think about. Connect with me here: Website: https://www.kimmillerhershon.com LinkedIn: https://www.linkedin.com/in/kmillerhershon Newsletter: https://link.kimmillerhershon.com/widget/form/aEdmdA1W5MhoMCMfy5O8 Webinar: https://webinar.kimmillerhershon.com/?utm_source=Podcast Guest Details: Company: Eagle Rock CFO Services Website: https://eaglerockcfo.com LinkedIn: https://www.linkedin.com/in/nickmjain/ If you’re building, leading, or scaling a business — and want a more practical, grounded perspective on leadership, finance, and experimentation-driven growth — this conversation offers both strategy and insight. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

    28 min
  5. Stop “Shoulding” on Yourself Webinar: 3 Leadership Decisions That Create More Revenue and Less Overwhelm

    4D AGO

    Stop “Shoulding” on Yourself Webinar: 3 Leadership Decisions That Create More Revenue and Less Overwhelm

    Leadership doesn’t have to mean carrying everything alone. If your business is growing, but somehow everything still lands back on your desk, it may not be a time management issue — it may be the decisions shaping your leadership. Join my FREE live webinar where I’ll walk you through 3 key decisions that help leaders increase revenue without adding more hours to their schedule. 👉 Save your spot here: https://webinar.kimmillerhershon.com Stop being the bottleneck. Start leading with more clarity, focus, and freedom. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

    6 min
  6. Chaos to Cash Flow: The Real Story Behind Multiple 7-Figure Businesses with Kevin Oneil

    MAY 1

    Chaos to Cash Flow: The Real Story Behind Multiple 7-Figure Businesses with Kevin Oneil

    In this episode of Unconventional Wisdom About Conventional Wisdom, Kim Miller-Hershon sits down with Kevin O'Neill — a multi-business owner who has built and scaled several seven-figure lifestyle businesses in the water sports industry. Kevin brings a raw, unfiltered, and refreshingly honest perspective on entrepreneurship, sharing the highs, the failures, and the unconventional path that led him to success. From growing up in Detroit with no connection to boating, to building a thriving water-based business empire, his story challenges the idea that success follows a straight line. He opens up about navigating ADHD, overcoming self-doubt, and learning business the hard way — through experience, mistakes, and relentless curiosity. Kevin also breaks down why blindly following traditional business advice (like over-leveraging or rigid systems too early) can actually hurt your growth. Beyond business, Kevin’s personality shines through — whether it’s raving in his late 40s, traveling the world, or building a life centered around freedom, fun, and family. This conversation dives deep into what it really takes to build something meaningful — and why knowing yourself is the ultimate advantage. We explore: Why “leverage everything” isn’t always smart business advice The reality of imposter syndrome — even at high levels of success Why financial literacy is a skill many entrepreneurs learn too late Building businesses that fund your lifestyle — not consume it The importance of hiring people better than you Why authenticity and self-awareness beat traditional leadership playbooks The power of exploring multiple business models instead of sticking to one lane How confidence is built by being in the room — even when you feel out of place Kevin’s story is proof that there’s no single formula for success. By embracing curiosity, leaning into your strengths, and staying open to opportunity, you can build a life and business that actually works for you — not one dictated by outdated rules. Connect with me here: Website: https://www.kimmillerhershon.com LinkedIn: https://www.linkedin.com/in/kmillerhershon Newsletter: https://link.kimmillerhershon.com/widget/form/aEdmdA1W5MhoMCMfy5O8 Webinar: https://webinar.kimmillerhershon.com/?utm_source=Podcast Guest Details: Book: Mate to Millionaire (available on Amazon) Website: (Coming soon) KevinAndGregLive.com If you’ve ever felt like you don’t quite fit the “traditional” mold of success — this episode will show you that might actually be your greatest advantage. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

    51 min
  7. Stop Shooting on Yourself Free Webinar

    APR 29

    Stop Shooting on Yourself Free Webinar

    Leadership doesn’t have to mean carrying everything alone. If your business is growing, but somehow everything still lands back on your desk, it may not be a time management issue — it may be the decisions shaping your leadership. Join my FREE live webinar where I’ll walk you through 3 key decisions that help leaders increase revenue without adding more hours to their schedule. 👉 Save your spot here: https://webinar.kimmillerhershon.com Stop being the bottleneck. Start leading with more clarity, focus, and freedom. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

    6 min
  8. The Truth About Leadership No One Tells You (From a CEO Who Built It Without Funding) with Dusty Gulleson

    APR 28

    The Truth About Leadership No One Tells You (From a CEO Who Built It Without Funding) with Dusty Gulleson

    In this episode of Unconventional Wisdom About Conventional Wisdom, Kim Miller-Hershon sits down with Dusty Goldson — CEO of Tectonic, a company he built over 25+ years without outside funding, hype cycles, or chasing trends. Dusty shares a grounded, no-nonsense perspective on leadership and growth, shaped by real-world experience scaling teams, navigating five acquisitions, and building businesses rooted in trust, consistency, and long-term relationships. His approach challenges the idea that success comes from rigid systems or quick wins — instead, he makes the case for clarity, adaptability, and people-first leadership. From rethinking decision-making styles to navigating the messy realities of acquisitions, Dusty opens up about what actually happens behind the scenes of “successful” businesses — including the expectations that don’t match reality, the people challenges leaders often underestimate, and the importance of self-awareness in high-stakes environments. Beyond business strategy, this conversation dives into leadership psychology — from managing impulsiveness and fast thinking, to embracing imposter syndrome as a tool for growth rather than something to avoid. We explore: - Why “bullet point thinking” can limit better decision-making - The hidden challenges behind acquisitions — especially people and culture - Why early success can sometimes create long-term problems - The myth of “we’re all family” in business — and what to believe instead - Why great leaders focus more on people than processes or platforms - The importance of self-awareness and moderating your natural tendencies - Building a culture of accountability — and not tolerating underperformance - Why solving problems (not selling solutions) is the key to long-term success - How imposter syndrome can actually be a healthy and necessary signal - The value of surrounding yourself with people who think differently Dusty’s perspective is a reminder that leadership isn’t about having all the answers — it’s about making decisions, learning fast, and staying honest about the realities of building and scaling a business. If you’ve ever felt the gap between how business is supposed to work and how it actually unfolds in real life — this episode will resonate. Connect with me here: Website: https://www.kimmillerhershon.com LinkedIn: https://www.linkedin.com/in/kmillerhershon Newsletter: https://link.kimmillerhershon.com/widget/form/aEdmdA1W5MhoMCMfy5O8 Webinar: https://webinar.kimmillerhershon.com Guest Details: Company: Tectonic Website: https://teamtectonic.com LinkedIn: https://www.linkedin.com/in/dustygulleson/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

    41 min
See All (72)

Ratings & Reviews

5
out of 5
4 Ratings

About

Unconventional Wisdom About Conventional Wisdom: Where clichés come to retire and fresh thinking we inspire. Smart minds don’t think alike—and that’s the point. Unconventional Wisdom About Conventional Wisdom takes you inside the messy, brilliant, and bold thought processes of high-achieving leaders, entrepreneurs, and out-of-the-box thinkers. We skip the clichés and spotlight the real talk: the strange decisions that worked, the brilliant ideas that bombed, and the thought patterns that defy the rulebook—but still lead to growth, impact, and the occasional mic drop. If you’re tired of surface-level advice and crave the kind of wisdom that makes you pause, laugh, and level up—this is your new favorite listen. Because let’s face it: playing it safe never built anything worth bragging about.

Information