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Unconventional Wisdom About Conventional Wisdom

Unconventional Wisdom About Conventional Wisdom

By: Kim Miller - Hershon
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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.Copyright 2025 All rights reserved. Economics Leadership Management & Leadership
Episodes
  • Career Pivots, Lifelong Learning, and Building a Business After an AI Layoff with Ryan Drumheller

    Career Pivots, Lifelong Learning, and Building a Business After an AI Layoff with Ryan Drumheller
    Jun 26 2026
    In this episode of Unconventional Wisdom About Conventional Wisdom, Kim Miller-Hershon sits down with Ryan Drumheller a self-described extroverted IT leader, fractional CIO, and founder of StellarHorn Group, where he helps businesses cut through the noise of technology and AI to drive real, measurable results. With over 20 years of experience in IT and leadership, Ryan is a relentless lifelong learner: two master's degrees, a bachelor's, more than 170 certifications, and doctoral ambitions still on the table. Outside of work, he's into music, sports, and video games and lately, golf. Ryan's path to all those credentials was anything but linear. He flamed out of community college after a year, landed an IT job quickly, and spent his twenties working hard without much of a plan. His parents young, with his dad a corrections officer steered him toward trade school, but Ryan was already taking apart PCs at night and quietly betting that IT was the future. The career epiphany didn't hit until his late twenties, when he looked at the hours he was putting in and thought, it can be different. That's when he went back for his bachelor's, then his master's, and never really stopped. In this conversation, Ryan challenges one of the most rigid beliefs in our culture: that there's one right path high school, straight to college, straight to career and that falling outside it means you won't amount to much. He's living proof otherwise. He and Kim get into how traditional education rewards a single narrow kind of intelligence, and how much talent gets boxed out because it doesn't fit. Ryan aced the technical classes he cared about even student-taught a programming course in high school while checking out of everything else. His bachelor's forced him through courses he found irrelevant; his master's, at a school built around relevant coursework, was night and day. Proof, as Kim puts it, that it can be done differently if we're open to it. Ryan and Kim also dig into the hard, honest math of going out on your own. Faced with a likely steady paycheck versus chasing the dream, Ryan landed on doing both taking the guarantee while building the product in the shadows. Along the way he learned something important about himself: he sells a product he believes in with total confidence, but selling himself as a service always felt like a stumble. The deeper realization is that he works better with people than as a solopreneur and instead of fighting his own nature, he's building something that fits it. Underneath it all, he's candid that imposter syndrome shows up in every phase, and that his answer is the same each time: look at the evidence, and remember that he's always figured it out before. This episode explores: Why the linear path — high school, college, career — isn't the only route to successHow a community-college flameout became a 170-certification careerWhy traditional education rewards one narrow kind of intelligenceUsing what you're good at to help you learn what's hardThe career epiphany: realizing "it can be different"Turning a job loss in the AI wave into a deliberate pivotHow a hobby meant to escape technology became the work itselfThe honest math of a steady paycheck vs. chasing the dream — and doing bothWhy if you can't sell, you don't have a businessBuilding around your nature instead of fighting it (team player vs. solopreneur)Using AI as a creative thought partner, not a human replacementWhy imposter syndrome shows up at every stage — and how evidence pulls you out"You're not a victim, you're a survivor": owning your experience and doing the work Ryan's perspective is a powerful reminder that there's no single timeline for figuring it out — and that the disruptions we don't choose can point us toward the work we're actually built for. His journey from a checked-out high schooler to a credential-stacking CIO building a company around the game he loves shows that you can take the unconventional route and still arrive somewhere that feels like home. If you're a leader, technologist, career-changer, or anyone who took the long way around, this conversation offers practical perspective, hard-won honesty, and a refreshing case that you can pick yourself up, pivot, and keep moving — no cheat codes required. Connect with me here: Website: https://www.kimmillerhershon.comLinkedIn: https://www.linkedin.com/in/kmillerhershonNewsletter: https://link.kimmillerhershon.com/widget/form/aEdmdA1W5MhoMCMfy5O8Webinar: https://webinar.kimmillerhershon.com/?utm_source=Podcast Guest Details: Guest: Ryan DrumhellerCompany: StellarHorn GroupFocus: Fractional CIO services; building golf technology software Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.
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    44 mins
  • From Abandoned at 11 to Trusted Advisor to Millionaires: Victoria Woods' Story

    From Abandoned at 11 to Trusted Advisor to Millionaires: Victoria Woods' Story
    Jun 23 2026
    In this episode of Unconventional Wisdom About Conventional Wisdom, Kim Miller-Hershon sits down with Victoria Woods wealth advisor, trusted advisor to millionaires, and founder and CEO of Chapelwood Financial Services, where she specializes in high-net-worth investment advisory. Victoria has been featured in Newsweek, named one of 100 Women to Know in America in 2023, and is the author of It's All About the Money, Honey. Victoria's story doesn't begin with wealth. It begins with a father who abandoned the family when she was eleven, a stay-at-home mom suddenly raising four kids on $96-a-month rent, and a childhood spent cooking for her siblings on a hot plate. She started babysitting at twelve and quickly went from minding one child to running six at a time. She built a celebrated retail career, walked away from the corporate world at twenty-three, and eventually built three companies over three decades. In this conversation, Victoria challenges one of the most paralyzing beliefs in business: the idea that you have to have all the answers before you're allowed to lead. Early on, she pretended she had it all figured out confident on the outside, "sweat running down my back" on the inside. What she learned was that nobody expects you to know everything, and admitting you don't isn't weakness. The real skill is being clear about who you are and where you're going, then having the nerve to ask for help getting there. A turning point came the night she asked her store manager for a raise she had earned top sales, most departments and was told the money was going to "Lazy Bill" in furniture instead, because Bill was married with children and she was single. By the next morning she was clear: she would never again let someone else decide her worth. It's the moment that crystallized the phrase she still lives by in the absence of courage, do it scared. Much of the episode is a masterclass in asking for what you want. Victoria describes the goal card she created in her fifties her photo, a QR code, and a handful of specific annual goals which she hands to powerful people across the table, then sits back in silence and lets them volunteer how they can help. She writes their names down, names the commitment out loud, and follows up. Even her own business coach was left speechless watching it work. Victoria and Kim also dig into generosity as a discipline rather than a reward "give while you're living" and the lesson that what you give out rarely returns from the direction you sent it, but always returns. They talk about the loneliness of building something that eventually doesn't need you, which is exactly the point: if the company depends on the founder, Victoria says flatly, you don't have a business, you have a hobby. And underneath it all, she's candid that imposter syndrome never fully leaves her answer is the same as always: keep serving, keep moving, and don't take advice from broke people. This episode explores: Why you don't need all the answers to start — and why pretending you do holds you backHow a childhood of scarcity became an entrepreneurial educationThe raise that wasn't, and the "fork in the road" moment that changed everything"In the absence of courage, do it scared" as a working philosophyThe goal-card method for asking powerful people for help — and why silence is the secretWhy asking for advice is a strength, not a weaknessGiving while you're living, and treating generosity as a responsibilityThat you don't have to be rich to help: a dollar's a dollarWhy a business that depends on its founder isn't really a businessThe bittersweet goal of training your team so well that clients stop needing youWhy imposter syndrome can persist at every level of successSpeaking to clients in plain English instead of jargon"Don't take advice from broke people" — and how to vet credibility before you listen Victoria's perspective is a powerful reminder that success isn't about arriving with all the answers it's about clarity, courage, and a willingness to keep serving even when you're scared. Her journey from a broken stove and floated checks to one of the most respected women-owned advisory firms in the country shows that you can build real wealth without losing your warmth. If you're an entrepreneur, advisor, leader, or anyone who's ever felt like they don't quite belong in the room, this conversation offers practical tools, hard-won wisdom, and a refreshing case that the bravest thing you can do is ask for what you want and then do the work. Connect with me here: Website: https://www.kimmillerhershon.comLinkedIn: https://www.linkedin.com/in/kmillerhershonNewsletter: https://link.kimmillerhershon.com/widget/form/aEdmdA1W5MhoMCMfy5O8Webinar: https://webinar.kimmillerhershon.com/?utm_source=Podcast Guest Details: Guest: Victoria WoodsCompany: Chapelwood Financial ServicesBook: It's All About the Money, Honey (also available as an audiobook) Website: FinancialDiva.com Hosted by Simplecast, an AdsWizz ...
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    48 mins
  • From Special Ops to $70M in Real Estate: Leadership, Letting Go, and Profits With Purpose with Jesse Sells

    From Special Ops to $70M in Real Estate: Leadership, Letting Go, and Profits With Purpose with Jesse Sells
    Jun 19 2026
    In this episode of Unconventional Wisdom About Conventional Wisdom, Kim Miller-Hershon sits down with Jesse Sells co-founder and chief operating officer of Impact Growth Capital, where he runs the daily operations of a diverse portfolio of properties and companies. With a strong passion for creating meaningful change, Jesse connects strategic vision with concrete results, making sure each project not only hits its goals but lifts up the community and the wider market along the way. Jesse's path was anything but conventional. He grew up poor in rural Oklahoma at times without running water before moving to Texas and joining the military, where he spent his twenties in military intelligence and was picked up by Special Operations. His work in foreign internal defense took him across the Middle East, where he learned Arabic and learned, over countless glasses of tea, how trust actually gets built. After leaving the service, he and his brother pooled roughly $20,000 in life savings and, within a few years, built a portfolio of nearly 1,500 units focused on affordable and workforce housing partnering with nonprofits to bring mental health and community services to the people living in them. In this conversation, Jesse challenges one of the most stubborn beliefs in business: the idea that you have to choose between making money and doing good. Raised to resent wealth — he admits that as a kid he saw a new truck and thought "showoffs" he carried the common stigma that profit and purpose can't share a room. Over time, he came to see that as flat-out wrong. The more he earned, the more he could change: pay for nieces and nephews, fund services, and get a seat at the tables where real decisions get made. As he and Kim put it, you can't shift policy from the outside; you have to be in the room. Jesse and Kim also dig into the limits of conventional success advice — especially the "millionaire in 60 days" promise and the social-media fantasy that one viral moment equals a career. Both push back hard. Real success, Jesse argues, is more available than ever but never overnight, and a candle that burns that bright tends to burn out fast. Much of the episode turns on leadership and the hardest lesson of scaling: letting go. Drawing on the military's clarity about "left and right limits," Jesse explains how he set clear boundaries and then trusted his people to make decisions inside them supporting each one the way they needed, not the way he preferred. Kim adds the piece she sees leaders miss most: it's not just about deciding which decisions belong to whom, it's about the *feelings and identity* wrapped up in handing them over. When a founder's whole sense of self is "I'm the decision-maker," they'll claw the work back no matter how good the system is. Throughout the conversation, Jesse is candid about imposter syndrome, the messiness of "building the plane while flying it," and the quiet discipline behind his growth daily study, daily meditation, and a relentless focus on the 80/20 of what actually moves the needle. His trick for staying grounded in any room, even across from a billionaire: find the human first. This episode explores: * Why the "money vs. meaning" trade-off is a false choice * How profits and purpose can reinforce each other rather than compete * Why real impact requires a seat at the table, not just good intentions * The Fort Worth bus-stop story and what creativity-plus-legwork really looks like * Why "overnight success" and viral fame are traps, not strategies * What the military teaches about leadership that the civilian world often doesn't * Why your calendar, not your intentions, reveals your real priorities * How to beat imposter syndrome by finding the human in the room * Why cultural awareness changes how you lead, sell, and connect If you're an entrepreneur, investor, leader, or business owner trying to grow something that matters without losing yourself in the process, this conversation offers practical insight, hard-won leadership lessons, and a refreshing case that doing well and doing good were never meant to be separate. 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: * Guest: Jesse Sells * Company: Impact Growth Capital * Focus: Affordable housing, infrastructure, and AI * LinkedIn: https://www.linkedin.com/in/jesse-sells/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.
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    35 mins
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