Unconventional Wisdom About Conventional Wisdom

Kim Miller - Hershon
  • 5.0 (5)
  • 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. 8h ago

    You’re More Ready Than You Think: Why You Don’t Need It All Figured Out to Start | Liz Mbwambo

    In this episode of Unconventional Wisdom About Conventional Wisdom, Kim Miller-Hershon sits down with Liz Mbwambo, founder of Upwynn Marketing, an agency built on a simple belief: established businesses deserve a marketing partner who truly understands what moves the needle. For most of her career, Liz worked on the vendor side of marketing, managing millions of dollars in annual media spend for brands ranging from national household names to local businesses. She saw firsthand how agencies make decisions, understood the incentives behind them, and recognized the gap between what clients were promised and what actually delivered results. After years entrusted with major marketing budgets, she left her six-figure career and bootstrapped her own agency from scratch, no investors, no safety net. A self-described hyper-planner (the one at the airport handing out the tickets), she opens the episode with the most out-of-character thing she's ever done: a last-minute trip to Spain where she planned absolutely nothing, and learned she doesn't have to be in control all the time. In this conversation, Liz challenges the misconception that you have to have it all figured out before you start a business. She always pictured the movie version, the polished business plan, the whole outline, and when her husband told her to go quit (warning she'd keep moving the goalpost otherwise), she jumped without it all mapped out. She barely had a business name, and rebranded a year later. Kim adds the nuance that keeps it honest: you don't need everything figured out, but Liz did bring real marketing expertise, which lowered the bar. As Liz puts it, borrowing Dave Ramsey's image, she pulled the boat closer to the dock so that when she jumped, she wouldn't land in the water. A rich, practical thread is who you surround yourself with, and what you share with whom. Liz's husband was the only person who knew her plan until the very end, not because her parents were naysayers but because she didn't want their protective fears (six figures, the health benefits her son depended on) to influence a decision that was really between her and her husband. She and Kim build it into genuinely useful advice: find mentors in different areas (the marriage you admire, the finances you want), look for people five years ahead of you, and if the people closest to you won't support your dreams, don't share them, talk about the weather instead and practice radical acceptance. Liz's reframe on the old "money makes you greedy" belief lands it: money magnifies what you already are, so a giving person with more money gives more. Liz is refreshingly candid that the "she's got it all figured out" image is a myth, every single day. People she worked with doubted she'd make it, and now, nearly two years in with a team of nine after fast growth, she still puts her pants on the same way, gets fevers, and has days she just wants to be a couch potato. There's no magic potion CEOs drink in the morning. She spent the entire year on operations because they were messy, and told a new senior hire that every system sits at about 80% done, no bow on it, you'll take it the last 20% of the way. The deeper lesson she's had to mourn: the picture of handing things off her plate and finally coasting never arrives. As a founder, you're always being looped into the next phase, which is really a lesson in adjusting your expectations. Her biggest leadership challenge is a live transition: she just hired a senior marketing manager so the team reports to him instead of coming straight to her, and she knows the adjustment (for them and for her) will take time as she steps back to work on the bigger picture. She and Kim bond over both building agentic AI workforces, Liz's CMO agent "Lizzie," Kim's "Moxie," both running on the Hermes platform, and Liz's tip to any founder: block off two days, build the agents, and your time will be far better suited long term. Her most unconventional growth habit this year is deceptively simple: taking care of Liz. Year one was head-down, business-business-business; this year she added a workout routine, slow mornings (coffee, the dogs, the morning sun) that have shifted her mind considerably, and firm boundaries, closing the laptop at five and keeping her home office for work only, so work doesn't bleed across the kitchen table. On imposter syndrome, she's honest it hits all the time, fueled by a social-media algorithm full of marketers who seem to have it all figured out, and sharpened by the pressure women put on themselves to be excellent wife, mom, friend, and owner all at once. Her fix is to talk to herself in facts (you didn't get much time with your son today, but you had a real conversation in the car, and watched a movie yesterday, you're a good mom), because imposter syndrome is mostly comparison and lies. Kim adds Dan Sullivan's horizon metaphor, measuring yourself against where you were last quarter rather than an ever-receding ideal, and Liz closes on the one she gives her own friends: talk to yourself the way you'd talk to a friend. This episode explores: Why you don't need it all figured out to start a businessPulling the boat closer to the dock before you jumpGuarding who you share your dreams with, and radical acceptanceFinding different mentors for different parts of your lifeWhy money magnifies what you already areWhy there's no magic potion, and every system is 80% doneMourning the picture of finally coasting, and adjusting expectationsTransitioning the team to report to a new leaderBuilding an AI workforce to free up a founder's timeTaking care of yourself: slow mornings, workouts, and real boundariesKeeping work from bleeding into homeBeating imposter syndrome by talking to yourself in factsMeasuring against your past self, not an ever-moving horizonTalking to yourself the way you'd talk to a friendLiz's perspective is a powerful reminder that readiness is a myth, that the support you surround yourself with matters as much as your expertise, and that building a business you can sustain means building a life you can sustain alongside it. Her journey from a six-figure corporate career to a fast-growing agency of nine shows that you can jump before you have it all figured out, as long as you pull the boat close to the dock first and keep talking to yourself in facts. If you're a founder, marketer, or anyone standing at the edge of a leap, this conversation offers practical insight, honest talk about imposter syndrome and boundaries, and a refreshing case that you're far more ready than the voice in your head is telling you. 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=PodcastGuest Details: Guest: Liz Mbwambo, Founder, Upwynn MarketingFocus: Marketing agency for established businesses; brings an insider's vendor-side perspective (millions in annual media spend managed) to help businesses make smarter marketing decisions and avoid strategies that don't serve their goalsWebsite: https://upwynnmarketing.com Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

    You’re More Ready Than You Think: Why You Don’t Need It All Figured Out to Start | Liz Mbwambo

  2. 3d ago

    Why You Don't Have to Tear It Down to Modernize a Legacy Business | Chad Bauer

    In this episode of Unconventional Wisdom About Conventional Wisdom, Kim Miller-Hershon sits down with Chad Bauer, president and owner of SR&B Advertising, an independent Baltimore agency that's been in business for more than 60 years. The second generation to lead the company, Chad took over from his father and transformed SR&B from a traditional ad shop into a performance-driven marketing agency. A lifelong entrepreneur who started, grew, and sold his first business before college, he's doubled the agency's revenue since taking the helm, built primarily through relationships and referrals, with a 94% client retention rate and a net promoter score of nine. He and Kim open the episode bonding over a shared obsession: competitive barbecue (she has the rib trophies to prove it; he's got the smoker and a friendly, unspoken cook-off running with his wife). A rich thread is the value of his unglamorous early experience, cutting grass and building a landscaping company from 13 to 18, then selling cars through college. None of it taught him payroll or benefits (the fire-hydrant realities he had to drink in later, working day to day beside his father), but all of it taught him relationship management, how to build genuine rapport that isn't a facade, with people decades older than him. He still gets Christmas cards from car-buyers twenty-five years later. He and Kim land on a shared conviction that even in an AI world, people are what make it all go round, and that asking better questions (his go-to: "what haven't I thought to ask?") isn't a sign of weakness but of genuineness and respect. Chad and Kim also take on the "we'll just use AI, we don't need you" objection head-on, with a story of a prospect's attorney-minded team insisting they'd just use Gemini or ChatGPT for their brand refresh. His answer: if you think AI can build what you envision, why are we even talking? AI gets you to the 20-yard line, or the two-foot putt, but the ball still has to go over the line, and that takes a trained professional who knows how to ask the right questions and pull what's actually in a client's head onto the page. He and Kim riff on the beauty and the limits of AI (it's predictive, it can't weigh all the human factors a brand actually requires), and the reframe that not knowing a prospect's industry can be the edge, because you see it through a fresh lens their competitors can't. His biggest leadership challenge, and his proudest fix, is structure. Through most of the company's history there were few real processes; his father was an owner-operator who called the shots. Growing meant building and documenting processes (then learning they go stale in a year if you don't set a review cadence), and it meant redesigning how the team meets. Inspired by Death by Meeting, Chad spent six weeks building a rhythm: daily ten-to-fifteen-minute stand-ups for alignment, weekly tacticals with a 90-second lightning round that surfaces the strategic topics, and monthly strategic sessions for the big picture, deliberately never mixing the day-to-day with the strategic. Decisions no longer wait for him, accountability is up, and he was explicit with the team that the goal isn't to be corporate, it's to be better than corporate while protecting a small, culture-driven shop. Kim adds her own meeting tool: put the desired outcome next to every agenda item (inform, brainstorm, decide) and a time allotment, because meetings drag most when the person who brought the item never got clear on what they actually needed. This episode explores: Why tearing down a legacy business is the wrong instinctLegacy plus transformation as a real competitive advantageHow early jobs taught relationship-building that still pays offWhy asking better questions is a sign of genuineness, not weaknessAnswering the "we'll just use AI" objection with confidenceWhy AI gets you to the 20-yard line but a human carries it overWhy not knowing an industry can be a fresh-lens advantageBuilding process discipline and keeping it from going staleA meeting rhythm that separates tactical from strategicPutting the outcome and time allotment on every agenda itemStudying yourself, not just the market, to find your true valueWhy a business can't grow beyond what its leader can seeGetting out of your own way so the company becomes an enterpriseBeating imposter syndrome by being the expert in what you bring, then listeningIf you're a founder, agency owner, or next-generation leader stepping into something built before you, this conversation offers practical insight, honest talk about process and imposter syndrome, and a refreshing case that legacy and transformation belong together. 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=PodcastGuest Details: Guest: Chad Bauer, President & Owner, SR&B AdvertisingFocus: Independent Baltimore marketing agency (60+ years); performance-driven marketing built on relationships and referrals, 94% client retention and an NPS of 9LinkedIn: https://www.linkedin.com/in/chadgbauer/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

    Why You Don't Have to Tear It Down to Modernize a Legacy Business | Chad Bauer

  3. Oct 2

    Stop Shrinking Yourself: On Owning Who You Are Later in Your Career | Victoria Woods

    In this episode of Unconventional Wisdom About Conventional Wisdom, Kim Miller-Hershon welcomes back a guest listeners already know and love, Victoria Woods, founder and CEO of Chapelwood Financial Services and a chief investment advisor with over 30 years of experience. Victoria is the author of It's All About the Money, Honey and has hosted a weekly radio show by the same name for over 20 years, and she and her team provide the "Millionaire Experience" with a special focus on empowering women investors to take control of their financial futures. Their first conversation was so good they came back for a second, this time on a subject both women are living in real time: what it actually takes to grow a business in your 50s, 60s, 70s, and beyond, at a stage when their own parents were handed a gold watch and shown the door. In this conversation, Victoria challenges the most entrenched piece of conventional wisdom about age: that you're supposed to wind down, retire at 65, and get out of the way. She's having none of it. If you choose to stay on planet Earth, she says, you need to be contributing value every single day, and ambition doesn't expire. What gets better with age, she argues, is that you finally figure out who you are. She calls it being bulletproof: you know your values, your work ethic, and how you want to show up, so when someone tells you that you can't wear pink nail polish in financial services or that you'd better "pull back the reins," you can simply say "next" and keep moving. That theme of self-editing runs deep, and it's where Victoria and Kim meet most honestly. Victoria recounts the Dallas executive who told her, decades ago, "this is not Dallas, you might want to pull back the reins just a little," and how that kind of comment lodges in your head and sends you spinning. But both women land on the harder truth: often no one has to shrink us, because we do it to ourselves. Kim admits it's taken her a long time to stop self-editing and fully embrace the whole gestalt of who she is, and they celebrate the view from this stage of life, bulletproof, unapologetic, occasionally lonely, but entirely their own. Much of the episode is a practical masterclass in energy and time. Victoria's non-negotiable belief is that the one thing you can never replace is time, which is why her firm runs on a simple promise: we don't waste time, money, or opportunity. When you're young, every opportunity feels like the last one, so you take them all and wear yourself out. Older and wiser, she runs each one through a filter, does this align with my vision, values, and goals?, and protects her energy fiercely, choosing just three speaking engagements each spring and three each fall. Her structure is tight but not rigid (80% planned, room to pivot on a dime), she does the three hardest things first each morning, and she's made her health a first priority after years of treating it as sporadic. Kim adds her own version: working smarter, guarding downtime, and releasing the guilt, echoing a friend's line, "you're allowed." This episode explores: Why retirement at 65 is an outdated idea, and ambition doesn't expireFinally figuring out who you are, and becoming "bulletproof"Refusing to shrink yourself, and catching the ways you self-editWhy time is the one thing you can never replaceRunning every opportunity through your vision, values, and goalsProtecting your energy and choosing commitments out of desire, not obligationStructure, doing the hardest three things first, and prioritizing healthReleasing the guilt around rest: "you're allowed"How ambition matures into legacy and pouring into your teamWhy a book is thought leadership, not a marketing trinketTurning down a big opportunity to protect your reputationWhy not every opportunity is really an opportunityHandling discrimination and the raise that changed her lifeWhy it's never too late to start, and doing it scared"Don't take advice from broke people, physically, financially, or spiritually"If you're building a business later in life, or anyone who's ever edited themselves smaller to make others comfortable, this conversation offers practical wisdom on energy, ambition, and legacy, honest talk about courage and discrimination, and a refreshing case that it's never too late to skid in sideways yelling "what a ride." 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=PodcastGuest Details: Guest: Victoria WoodsCompany: Chapelwood Financial ServicesBook: It's All About the Money, Honey (also available as an audiobook) Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

    Stop Shrinking Yourself: On Owning Who You Are Later in Your Career | Victoria Woods

  4. Sep 29

    Work Smart, Not Hard: The 80/20 Reframe That Changed How She Runs Her Business | Cherry Lao

    In this episode of Unconventional Wisdom About Conventional Wisdom, Kim Miller-Hershon sits down with Cherry Lao, founder and CEO of Citizen Best, a brand marketing agency that helps growing companies align how they show up with where the business is headed. Over the past several years, her team has worked with brands like Netflix, HBO Max, Mars, and TechCrunch, plus a run of fast-growing lifestyle and food-and-beverage companies, on the moments that actually move a business: a launch, a repositioning, or a stretch of growth the brand hasn't caught up to yet. Citizen Best partners with founders and marketing leaders navigating pivotal moments, where the collaborative process is the product and creative excellence is the baseline. Off the clock, Cherry is a devoted dancer (Cuban dance, reggaeton, whatever the Bay Area's rich dance community is teaching), and she finds the dance floor sparks creativity for her clients' work. In this conversation, Cherry challenges a piece of conventional wisdom she believed for years: hustle harder, work harder, and the trajectory only goes up. She was always the last one to leave the office, whether at a small agency, a big corporation, or her own co-working space with the building lights half out, quietly treating that as a badge of honor. What finally reframed it was motherhood. Two pregnancies taught her that her body allowed only a certain capacity, which forced the real question: if the day is shortened, what are the critical few things that actually move the business forward? She'd heard the "work smart, not hard" 80/20 wisdom forever, but being stubborn, she had to live it firsthand before it clicked. That opens into a rich thread on priorities and the tyranny of the calendar. Kim tells the story of a CPA client who showed up to a coaching call a month out from a filing deadline, drowning in work, and when Kim asked why she was even there, the honest answer was "because it was on my calendar." They name the hamster wheel of doing things simply because that's how things are, and the harder discipline of pausing to ask whether this is really how the week should be structured, especially when your own initiatives compete with the always-urgent client work. Kim extends it to the difficult-conversation version: we don't actually decide, we just procrastinate, and either have the conversation or consciously take it off the list, because keeping undone things there just feeds a negative self-talk reel that quietly undermines you. Cherry is candid that outsiders assume she has every aspect of business figured out, and the truth is there are always gaps. It took her until year 11 to confidently say she's the CEO of a company. The first half of the decade she stepped into ownership from her creative strength as an art and creative director, fluent in that language but facing a huge gap around finance, operations, and HR, the critical functions that exist even with a seven-person team. The through-line she's landed on is resilience: no matter your stage, you'll always not know something, you'll always get metaphorically punched in the face, and the work is learning how to keep getting up and pull yourself out of the dip. She and Kim bond over a shared leap of faith. Both are stepping out of their comfort zones, Kim prioritizing the podcast and social media around her January book, Cherry finally taking Citizen Best out of "best-kept secret" mode to create content, speak, and launch a product. The clarity work they do for clients (what's your story, what's unique about you) is exactly what took Cherry longest to do for herself, and once she had it, the desire to get out there unlocked, not for fame, but to share the impact of the work. They agree on the core bet: you don't know the outcome, but if you don't take the leap and start, it definitely won't work. Kim's parallel from writing her book lands it: what everyone sells as a marketing tool turned out to be her intellectual property and thought leadership, something bigger than her that needed to get into the world. Her biggest leadership challenge is building culture and camaraderie across a remote team split between the US and Bangkok, without a water cooler or a ping-pong table, and keeping the core values thriving. It sparks a warm exchange about wanting to feed and care for far-flung teams, and both women manifest a team retreat out loud, Cherry's in Thailand, Kim's in Europe with her Nigeria-based team. Her unconventional growth habit is simply to ask for help, delegate, and stop trying to know it all, leaning on both her team (who do many things better than she can) and the right business coach and network to lift her up so she can lift everyone else. Kim adds the delegation nuance she returns to often: when someone doesn't deliver, it's frequently a management error, not an employee one, because seeing a finished product for the first time at the deadline means you never set them up for success. The deeper leadership move, as Cherry puts it, isn't instilling your own way of doing things but recognizing how each team member works and creating the space and workflow for them to own it, and, sometimes, taking responsibility when it breaks down anyway. This episode explores: Why "hustle harder" is the wrong measure, and working smart matters moreHow motherhood forced a real reckoning with capacity and prioritiesThe 80/20 question: what few things actually move the business forwardThe tyranny of doing things just because they're on your calendarDeciding to have (or not have) the hard conversation instead of procrastinatingClearing your to-do list to quiet the negative self-talk reelWhy it took 11 years to feel like the CEO, and the finance/ops/HR gapResilience as the real through-line of entrepreneurshipTaking the leap on content, speaking, and a new productWhy a book (or a brand) is thought leadership, not just a marketing toolBuilding culture and camaraderie across a remote, two-country teamAsking for help, delegating, and refusing to know it allWhy a missed deadline is often a management error, not an employee oneLeading to each person's working style and letting them own the workflowCherry's perspective is a powerful reminder that success isn't about being the last one in the office or having every gap filled, it's about clarity, resilience, and the willingness to keep getting up and take the leap even when the outcome is unknown. Her journey from creative director to eleven-years-in CEO shows that the clarity we give others is often the hardest to give ourselves, and that leaning on your team and your community is what lets you lift everyone else. If you're a founder, marketer, or creative stepping into a bigger version of your business, this conversation offers practical insight, honest talk about priorities and resilience, and a refreshing case that working smart and asking for help will carry you further than hustling alone. 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=PodcastGuest Details: Guest: Cherry Lao, Founder & CEO, Citizen BestFocus: Brand marketing agency helping growing companies align how they show up with where the business is headed; work with founders and marketing leaders through repositioning, fundraising, launches, and growth (clients include Netflix, HBO Max, Mars, and TechCrunch)Website: https://citizenbest.comLinkedIn: https://www.linkedin.com/in/cherrylao/Special offer for listeners: Brand Signal Assessment A fast, focused read on where your brand stands, a brief survey, AI-assisted analysis, and an experienced human strategist in the loop, so you walk away knowing where the gap is, what it's costing you, and where to focus first. Normally $595, discounted to $395 for listeners (promo code to come). Learn more: https://citizenbest.com/brand-signal-assessment/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

    Work Smart, Not Hard: The 80/20 Reframe That Changed How She Runs Her Business | Cherry Lao

  5. Sep 25

    Why People Leave Corporate to Buy a Franchise — and What Makes or Breaks the Deal | Adam Goldman

    In this episode of Unconventional Wisdom About Conventional Wisdom, Kim Miller-Hershon sits down with Adam Goldman, a franchise coach, consultant, author, and entrepreneur who has spent the last nine years helping hundreds of people transform their lives through franchise business ownership. As the author of The Franchise Lifestyle, Adam breaks down what it takes to find the right opportunity and what can make or break a deal. He's also the founder of Franchise Visa, where he helps foreign investors pursue US E-2 visas through franchise investment, bridging the gap between entrepreneurial ambition and US immigration goals. Off the clock, he's an avid jigsaw puzzler who finds the strategy of it (and the process of elimination) genuinely therapeutic. In this conversation, Adam pushes back on the very premise, since he's never really been a conventional-wisdom person. Graduating from the University of Illinois into traditional recruiting with the likes of ADM, Ford, and Toyota, he decided instead, in the 1990s, to launch his career in Eastern Europe through an internship in Budapest. That instinct shapes how he sees his clients: most people, he says, underestimate how powerful social norms are, doing what they're "supposed" to do without being able to explain why, which for many means getting a corporate job by default. The switch that finally turns for them is almost always emotional, family they can't show up for, or being tired of making someone else rich when they always wanted to build something themselves but never had the guts. That leads into one of the episode's richer threads, the pull between practical safety and natural inclination. Kim names the pattern she sees constantly: people take the corporate job because it's what you're supposed to do, spend 10, 15, 20 years quietly miserable, and get hooked on the predictable paycheck and the responsibilities that make it so hard to leave, something both she and Adam, as entrepreneurs, know well. They connect it to the previous episode's guest, Alex Sanfilippo, wired for entrepreneurship at age 10, who still went and got a corporate job as an adult, proof of how strong the conventional current runs even in people built to swim against it. Adam is refreshingly honest that his business is only as good as the leads at the top of his funnel, and that lead flow, getting enough high-caliber people in the door, is his single biggest challenge. It's compounded by a moment where people increasingly assume AI can do what he does, which he considers misfounded, the equivalent of asking Google which franchise to buy. Kim's reframe lands it: anyone who thinks they can substitute your judgment, subtlety, and matchmaking with a chatbot probably isn't the right client anyway, because they likely won't succeed at running a business on their own. And a harder truth underneath: many people don't even know his profession exists, so the real climb is getting a stranger to invest 90 minutes exploring franchise brands with a free service from someone they don't yet trust. The two also dig into positioning in a rapidly shifting world, and the myth that social media is the answer. Adam is blunt that you won't find the right franchise brand on Instagram or TikTok, and that seasoned professionals further along in their careers simply aren't there looking. The good news, he argues, is that the current moment has renewed people's appreciation for relationships, face-to-face connection, and someone actually spending time and energy on them, which is exactly what a relationship business built on a free consultation offers. Kim adds her standard antidote to economy-doom thinking: you don't need all the people, just enough to keep your enterprise going. His unconventional growth habit is a conviction that success lives in the agency of others. Most people pay lip service to it, choosing 100% of their own effort over 1% of a hundred others', but Adam credits his team as the secret sauce and isn't afraid to say he's totally reliant on them. It sparks a delightful exchange about Kim building an AI operating system for her own business, not to replace her people but to enhance them, and both note how much more often they're hearing that enhance-not-replace framing lately, a welcome contrast to the big tech layoffs. On imposter syndrome, Adam's answer is the four words he coaches his daughters with in sports: "So what? Now what?" Don't dwell on the placements you didn't make, focus on now. Kim loves it because it treats a setback as a circumstance outside you rather than an identity, and they close on the shared insight that tying your identity to success is just as dangerous as tying it to failure, because you have to have the lows to know what the highs feel like. This episode explores: Why so many people take the corporate path simply because it's expectedThe emotional switch that finally moves people toward ownershipHow practical safety and the steady paycheck override natural inclinationWhy lead flow is the perennial challenge of any relationship businessWhy AI can't replace the judgment and subtlety of real matchmakingWhy the right client isn't the one who'd hand the decision to a chatbotThe challenge of a profession most people don't know existsWhy social media isn't where seasoned professionals find their next chapterThe renewed appreciation for face-to-face relationships"You don't need all the people, just enough"Success lives in the agency of others, and naming your team as the secret sauceUsing AI to enhance your team, not replace it"So what? Now what?" as a reset for setbacksWhy tying identity to success is as risky as tying it to failureAdam's perspective is a powerful reminder that the safe, expected path isn't the only one, and that building a business, or a life, worth wanting often means going against the current of what you're supposed to do. His journey from turning down traditional recruiting for an internship in Budapest to helping hundreds of people find their own franchises shows that the human element (relationships, judgment, and someone genuinely invested in your dream) is the one thing no algorithm can replace. 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=PodcastGuest Details: Guest: Adam Goldman, franchise coach, consultant, and author of The Franchise LifestyleFocus: Helping people find the right franchise opportunity; founder of Franchise Visa, helping foreign investors pursue US E-2 visas through franchise investmentWebsite: https://www.franchisecoach.net/houston/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

    Why People Leave Corporate to Buy a Franchise — and What Makes or Breaks the Deal | Adam Goldman

  6. Sep 22

    The PodMatch Founder on Focus, Saying No, and Building for Someone Other Than Yourself | Alex Sanfilippo

    In this episode of Unconventional Wisdom About Conventional Wisdom, Kim Miller-Hershon sits down with Alex Sanfilippo, podcaster and founder of PodMatch, a platform that automatically matches podcast hosts and guests for interviews, like a dating app for podcast interviews instead of dates. Through PodMatch and his podcast Podcasting Made Simple, Alex helps independent podcasters grow their influence and revenue so they can better serve their listeners. (Full disclosure that Kim shares up front: she's a premium PodMatch member and has been matched with many of her guests through it.) An entrepreneur since age 10, when he organized a neighborhood operation fishing golf balls out of the water hazards and selling them back to golfers, Alex ran a 15-year aerospace career before going all in on PodMatch. In this conversation, Alex challenges a piece of conventional wisdom his corporate years drilled in: diversify, build a portfolio, keep side hustles, don't put your eggs in one basket. It's not bad advice, he says, but it isn't his. He performs better, happier, and faster when he does the opposite, and he turned the word FOCUS into his motto: Follow One Course Until Successful. Six years into PodMatch it's the only thing he does, and while friends call him the most boring guy ever for it, that singular focus is exactly what keeps his head clear and accelerates the business. Kim frames the deeper lesson as "know thyself," the same theme as her book coming out in January, and notes how it defies the shiny-object stereotype of the entrepreneur. One of the episode's most memorable stories is how PodMatch came to pay podcasters, a genuinely unconventional move for a software company. Early on, hosts were leaving and Alex didn't know why, so instead of assuming, he asked every off-boarding member for five to ten minutes on a call. The surprise: most weren't quitting PodMatch, they were quitting podcasting entirely because their family couldn't justify the hobby's cost. So the team built a 50/50 revenue split, half to keep the lights on and grow, half back into podcasters' hands, enough to at least offset production costs so no one has to quit over money. As the company has grown, they take less and give more. It came, Alex says, from believing in the power of podcasting itself. Alex is refreshingly candid about what he still wrestles with: he overcomplicates things and sometimes sends his team in the wrong direction. Being so focused, he can turn something small into six months of work when an hour would do, and he can misread what people are actually saying (the very reason he almost missed the "why are you quitting?" follow-up that led to paying podcasters). His guardrails are his co-founders, his wife Alicia in operations and support and developer Jesse, who help him slow down and right-size the idea. Kim connects it to her own planner's superpower and shares how she avoided the wrong-direction trap with her podcast: a 50-person survey of ideal clients revealed that none of them Google for leadership advice, they get it from podcasts and books, so she built the show around a clear value for the listener before she ever hit record. On imposter syndrome, Alex is honest that it hits every time he launches something new. When he posted about paying podcasters, the very first of nearly a thousand comments called it the stupidest idea he'd ever heard, and instantly the "why am I even doing this?" flooded in. Six years in, it still happens, and he's built a real process for it: let the rumination play all the way through rather than letting it loop for free, then reframe by asking why he did it, because if the answer were "to make money" he'd have every right to feel anxious, but it's always been for someone else, so if it wasn't for that person, it's for another. Then he prays to quiet his mind, gives up all hope for a better past, and takes a walk away from the devices. Kim's addition lands the whole hour: reframe the discomfort as progress, remember there's an equal and opposite true story you get to hang onto, and hold onto the value you bring, because it's bigger than you. This episode explores: FOCUS: Follow One Course Until Successful, and why diversifying wasn't his path"Know thyself" as the real foundation for how you run a businessAsking off-boarding users why they leave instead of assumingPaying podcasters: an unconventional 50/50 revenue splitOvercomplicating and wrong-direction as honest leadership strugglesCo-founders as guardrails, and right-sizing the ideaSurveying ideal clients to build around real listener valueProtecting the core product against feature bloatWhy subscription bloat drives customers away"Do things that don't scale" and staying a working founderWalking away from successful rooms whose values don't align with yoursBeating launch-day imposter syndrome by letting the thought play throughReframing the "why": doing it for someone else, not for youReframing a "no" as progress and remembering the value you bringIf you're a founder, podcaster, or anyone tempted to chase every shiny object, this conversation offers practical insight, honest talk about imposter syndrome, and a refreshing case that following one course until successful, and serving the people in front of you, is its own kind of strategy. 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=PodcastGuest Details: Guest: Alex Sanfilippo, Founder, PodMatch; host of Podcasting Made SimpleFocus: PodMatch, a platform that automatically matches podcast hosts and guests for interviews; helping independent podcasters grow their influence and revenueWebsite: https://www.podmatch.com Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

    The PodMatch Founder on Focus, Saying No, and Building for Someone Other Than Yourself | Alex Sanfilippo

  7. Sep 18

    Built to Finish: What 18 Ironmans Taught Him About Scaling and Selling a Company | Steven Pivnik

    In this episode of Unconventional Wisdom About Conventional Wisdom, Kim Miller-Hershon sits down with Steve Pivnik, a successful entrepreneur who scaled his last company to 200-plus employees across 12 countries and executed a strategic exit to a $4 billion competitor using a disciplined, repeatable framework. That discipline was forged not only in the boardroom but through elite endurance challenges, including 18 Ironman triathlons and high-altitude mountaineering expeditions, including Everest. Steve is the best-selling author of Built to Finish, a keynote and TEDx speaker, and host of the Built to Finish podcast. Today he advises founders and CEOs on building companies intentionally designed not just to grow, but to finish strong through a strategic acquisition or investor recapitalization. His Ironman journey is its own story: a "midlife crisis" he started at 40 with no athletic background, chasing a 13-year goal of crossing the finish line at the Kona World Championship. In this conversation, Steve challenges the founder's most seductive belief: that because it's your company, you have to do the heavy lifting, be in every big sales call, own every big decision, the Superman complex. He learned, over many years, that the best way to scale is to remove yourself from those decisions, because that's when you unleash the business's true potential. He puts hard numbers on it: a founder who stays the hub of every spoke caps the company's valuation, while one who builds systems, delegation, and a real management team can double or triple it. The aha moment for his clients is that stepping back doesn't just free them from an 80-hour week with a laptop on every vacation, it makes the company worth more. That reframe sits right at the inflection point where Kim is often brought in, the moment a founder knows they need to stop being the bottleneck but can't actually execute the letting go. She and Steve are a natural complement, his data and strategy alongside her work on the psychology of releasing control and on leveling up the executives who were never allowed to make decisions independently. Steve's rule, from a mentor, is to delegate when someone is 70% ready rather than waiting for a 100% that never comes, and Kim adds the gut-check she can't resist: when you insist no one can do it as well as you, is that true, or is it your ego, and are you making someone else wrong to avoid letting go of something it's time to release? They agree servant leadership works only with the right cadence, because somebody still has to draw the line and say "that's not my job, it's yours." Steve is refreshingly candid about what people assume he had that he didn't. His LinkedIn shows a Harvard credential (an online course he took after the exit), but he's a proud college dropout from the school of hard knocks, and his company was bootstrapped from day one with not a dollar of outside funding. He left school not out of rebellion but because his family hit hard times and his mother, unimpressed by a four-year business degree, pointed her "computer nerd" toward a downtown Manhattan mainframe programming course, a get-out-of-jail-free card he happily took. It leads into a shared riff with Kim on how traditional education rewards one narrow kind of intelligence, illustrated by her son who could see the answer instantly but got failed for not documenting a "process" he didn't consciously have. His biggest leadership challenge is one he calls endemic and hates discussing because it's personal to others: founder loyalty to the people who built the company with them. The best friend, cousin, or uncle who ran sales or finance from day one deserves enormous credit, but often can't run the organization at the level it's grown to. For the key roles, he argues, you need someone who has already run an org at double your current size, because it'll be a cakewalk for them versus a struggle for your loyal early hires. Kim adds the humane counterpoint from her coaching: those people are usually miserable being in over their heads, and giving them permission to make a better decision for themselves lets them leave with dignity, choosing the exit rather than waiting for the other shoe to drop. His unconventional growth habit is the realization that he doesn't have all the answers, becoming coachable after years of "my way or the highway." Kim's favorite reframe lands the point: being open to coaching isn't a sign you're failing, it's what LeBron James, Serena Williams, and Patrick Mahomes do, top performers surround themselves with many coaches. Both of them have coaches, both practice what they preach, and both agree that if you're fantastic at one thing you're almost certainly lacking in another. On imposter syndrome, Steve is honest that it hits every time he's about to walk on stage, the "why me?" backstage, until he reminds himself he earned the spot and gives himself a pep talk. Kim's addition ties the whole hour together: the nerves mean you care, and the cure is remembering the message was never about you, you're just the vessel, so make the audience the hero. His closing charge is pure Steve: if a self-described couch-potato college dropout can build and sell a company and finish the Ironman World Championship, nothing should stop anyone from setting a big, hairy, audacious goal and going after it. This episode explores: Why the founder's Superman complex caps growthHub-and-spoke architecture and what it does to your valuationHow stepping back can double or triple what your company is worthDelegating at 70% ready instead of waiting for a 100% that never comesThe ego question: is it really true no one can do it as well as you?Servant leadership with the right cadence, and knowing when to draw the lineBootstrapping to a $4 billion exit as a college dropoutWhy traditional education rewards only one kind of intelligenceThe hardest call: outgrowing the loyal early team in key rolesWhy the person who's outgrown their role is usually miserableLetting people leave with dignity by choosing the exit themselvesBecoming coachable, and why top performers have many coachesBeating stage-fright imposter syndrome by making the audience the heroSetting big, hairy, audacious goals and starting before you're readyIf you're a founder, endurance athlete, or anyone sitting on a goal that feels too big, this conversation offers practical insight, honest talk about letting go and imposter syndrome, and a refreshing case that you were built to finish. 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=PodcastGuest Details: Guest: Steve PivnikBook: Built to FinishFocus: Advises founders and CEOs on building companies intentionally designed to finish strong through a strategic acquisition or investor recapitalization; scaled and sold his last company (200+ employees, 12 countries) to a $4 billion competitor; keynote and TEDx speaker, host of the Built to Finish podcast, 18-time Ironman and Everest mountaineer Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

    Built to Finish: What 18 Ironmans Taught Him About Scaling and Selling a Company | Steven Pivnik

  8. Sep 15

    The Quiet Advantage: How Introverts Lead and Sell on Their Own Terms | Jennifer Kelly

    In this episode of Unconventional Wisdom About Conventional Wisdom, Kim Miller-Hershon sits down with Jennifer Kelly, founder of New Initiatives Marketing, a B2B marketing firm that works with mid-market, mostly technical companies to build strategies, systems, and sales enablement programs that turn marketing into a revenue engine. With deep corporate experience at the Financial Times, Siemens, and Motorola, Jen brings real expertise in technical, industrial, and consulting engineering firms. She's based in Toronto and, given a hypothetical year off with no money concerns, would spend it getting better at polo, the first polo player Kim has ever interviewed. In this conversation, Jen challenges two pieces of conventional wisdom loudly at once. The first, and the thread that anchors the whole episode, is that you have to be an extrovert to lead a business. Growing up with an entrepreneur father who was a huge personality, she absorbed the message that to be good at business you had to be like him, and since she wasn't, she quietly counted herself out for years, until a layoff pushed her into running her own company. It's flatly untrue, she says: introverts often do sales better, because observing and listening more than you talk is exactly what wins the right partners, deals, and hires. The second is the worship of revenue. The business press celebrates ever-bigger top-line numbers, but running a company taught her the number that actually matters is profit. Jen is candid that the thing people assume she has nailed, client service, is exactly what has no formula, because every client is different and the right approach can shift mid-contract as their business or their sponsor changes. Some want weekly reports, some want quarterly check-ins, some only want to hear from you when something's wrong. Kim offers her go-to tool: ask up front what success looks like six months out, because most unmet expectations are ones the client never articulated, and you only discover them when you've already missed. They range from there into defining vague standards like a "no a*****e policy" (is a blunt high-D driver an a*****e, or the passive-aggressive one?) and the hard truth that in client service you have to read between the lines, because sometimes you get fired over something no one ever told you. On imposter syndrome, Jen is clear about when it strikes, going after a bigger client than she's served before, and the voice of "who do we think we are?" Her fix is simply naming it, because once she can call it imposter syndrome she can talk herself off the ledge and go for it anyway. Kim adds the neutralizing thought she loves: you already don't have that business, so a no leaves you exactly where you started, which makes the only real question how many rooms you've talked yourself out of walking into. This episode explores: Why profit, not revenue, is the number that mattersGiving introverts guardrails instead of telling them to changeBuilding on strengths rather than reinforcing weaknessesWhy client service has no formula and stays bespokeDefining vague standards like a "no a*****e policy"Reading between the lines in client relationshipsThe core AI question: wrap the old machine or rebuild it entirelyWhy a leader's vision caps how far the company can goWhy junior-plus-AI can't replace hard-won judgmentDesigning services for profitability from the startFlat subscription billing that kills timesheet stressIf you're a founder, marketer, or self-identified introvert who's ever counted themselves out, this conversation offers practical insight, honest talk about AI and imposter syndrome, and a refreshing case that you get to lead exactly as who you are. 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=PodcastGuest Details: Guest: Jen Kelly, Founder, New Initiatives MarketingFocus: B2B marketing strategy, systems, and sales enablement for mid-market technical, industrial, and consulting engineering firms; based in TorontoWebsite: https://www.newinitiativesmarketing.comLinkedIn (Jen): https://www.linkedin.com/in/jenniferkelly/LinkedIn (New Initiatives Marketing): https://www.linkedin.com/company/new-initiatives-marketing/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

    The Quiet Advantage: How Introverts Lead and Sell on Their Own Terms | Jennifer Kelly
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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.

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