Unconventional Wisdom About Conventional Wisdom

Kim Miller - Hershon
  • 0.0 (0)
  • 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. 2 days ago

    You Don’t Have to Follow the Standard Playbook to Build Something That Works | Michelle Griffin

    In this episode of Unconventional Wisdom About Conventional Wisdom, Kim Miller-Hershon sits down with Michelle Griffin, PhD, founder and CEO of Griffin Resources, where she helps organizations navigate the complex, often uncomfortable HR challenges that do not come with a standard playbook. With more than a decade of experience, Michelle has guided businesses through process changes, mergers and dissolutions, HR analytics, and leadership development. She also happens to have once petted a wild moose while feeding it a Pixy Stick, a childhood Alaska story that sets exactly the right tone for a conversation about doing things the unconventional way. Michelle was born and raised in Alaska before a culture-shock move to Florida in high school, trading snow on the ground in July for triple-digit heat. That early adaptability turned out to be a theme. Her entire business model was born from refusing to accept a convention that did not serve her or her clients. The conventional wisdom Michelle followed early on, and then threw out, was the consultant's retainer. She researched what everyone else charged, set up a monthly retainer with a set number of hours, and quickly found it fit no one. It was hard to track, hard to keep profitable once drive time entered the picture, and clients disliked it as much as she did, never quite trusting they were getting their money's worth. Around the two-and-a-half-year mark, with 10 to 12 employees already on the books, she made a bold switch to a clocked-hourly model billed at the end of each month. It meant floating nearly three payrolls before the money ever came in, and it still takes real effort to explain to clients, but it solved the fairness problem completely. Clients pay for exactly the work done, nothing more. For small businesses on tight budgets, the model can even go dormant for months and pick back up at the same rates, no contract to cancel. As Michelle put it, she did not have an MBA telling her the "right" way, so she simply had an idea and tried it. That instinct for flexibility runs through how she has built the company, now roughly 40 team members serving about 75 clients. Michelle's firm operates like an outsourced internal department: HR, payroll, and recruiting support that functions as if the client had its own in-house team. Asked what people assume she has figured out but still wrestles with, Michelle is honest about work-life balance. She started as a contractor while finishing her doctorate, meaning only to cover some bills, and grew the business to seven figures in three years while managing a team and writing a dissertation. Her motto was "this too shall pass," but when the doctorate was done, she poured the same hours right back into the business. She admits she has essentially never taken a real day off, though this year she has started protecting her weekends. The reframe that stuck with her is that less is not laziness, and that not doing something does not make her unproductive when the business is still thriving. She is actively working on giving her executive team real authority so she stops being, in her words, a roadblock and a speed bump, which is also the beginning of a genuine succession plan. On her biggest leadership challenge, Michelle names the hardest problem in a people-based service business: knowing when and how to hire. She watched a fractional-CFO firm go under by paying full salaries for work that had not yet materialized, and she deliberately built the opposite. Her team is largely part-time, ramping to full-time as real work is assigned, with training and knowledge transfer paid internally so clients never foot that bill. Because she is no longer in the trenches, she relies on her managers to read not just the numbers but how people are actually feeling, whether the team is stretched too thin, where the skill gaps are, and when to start pipelining. She is candid that this cart-and-horse dance may never be fully solved, and that at some point the real question becomes how big is big enough, a conversation she and her husband, who runs a larger IT business, return to often. This episode explores: Building an entire business model by rejecting the standard retainerWhy a clocked-hourly, bill-at-month-end model felt fairer to clients and to herStaying nimble enough to go dormant and restart without canceling a contractThe real cost of growing to seven figures while finishing a doctorateWhy "less is not laziness," and unlearning the grind-harder reflexGiving an executive team authority so the founder stops being the roadblockKnowing when and how to hire in a people-based service businessHow overpaying for salaries before the work exists can sink a firmLearning to sell someone else's skill set, not just your ownRefusing to push a founder's work ethic onto the teamProtecting boundaries and training clients to respect themReframing imposter syndrome as a thought process you can controlWhy the real conversation lives underneath the situation, not in itIf you are a founder or business owner who has become the bottleneck in your own company, this conversation offers a candid, practical look at delegating authority, setting boundaries, and building something that can thrive without you in every decision. 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=PodcastFree Resource: The Delegation Reset: 12 moves to delegate better and live better, [Download Here]Guest Details: Name: Michelle Griffin, PhDCompany: Griffin ResourcesFocus: Outsourced HR, payroll, and recruiting support for organizations nationwide (all 50 states), plus leadership development and complex HR challenges Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

    You Don’t Have to Follow the Standard Playbook to Build Something That Works | Michelle Griffin

  2. 6 days ago

    Why Focus Beats Owning a Little of Everything | Zander Kempf

    In this episode of Unconventional Wisdom About Conventional Wisdom, Kim Miller-Hershon sits down with Zander Kempf, founder and CEO of Clear Summit Investments, where he helps investors pursue financial freedom through unconventional real estate. After nearly a decade working with high income earners, Zander moved beyond traditional real estate into glamping resorts and hot springs near national parks, focusing on value-add properties that let investors grow their wealth while creating experiences they can actually enjoy. He is also a former Army paratrooper who now lives in Hawaii and spends his days paragliding, kiteboarding, free diving, rock climbing, and surfing. His whole company, fittingly, is built around the outdoors. The conventional wisdom Zander followed early on, and later rejected, was the idea that rich people own a little bit of everything: five businesses, 18 ventures, multiple income streams for their own sake. He came to see that the real path was the opposite. Hyper-focus on one thing, do it better than anyone else, and keep cutting. He and his team still ask daily what the most effective 20% is and how to strip away the other 80%. He is candid that focus is hard, naming what he calls the entrepreneur's curse: once you learn to spot opportunity, you see it everywhere, and resisting every shiny object takes real discipline. Asked what people assume he has figured out but still wrestles with, Zander goes straight at a myth about wealth. People assume business is easy and that a lot of property means a lot of cash, when in real estate it is common to be equity rich and cash poor. You can own tens of millions in property without holding anything like that in cash. That reality drove a major strategic shift at Clear Summit, from a near-total focus on equity at the start to an almost complete focus on cash flow now. As Kim put it, recalling her stepmother during a recession, you cannot take the deed to the house and buy groceries with it. On his biggest leadership challenge, Zander counts himself fortunate rather than stuck. The 25-person company has been strict about bringing in only A players who are also genuine culture fits, people who live the outdoor, freedom-and-wellness lifestyle the resorts are built around. His model is a development group: buy undervalued, mismanaged resorts, improve operations, expand them through an in-house construction arm, and operate them long term. Because they stay in one asset class, the first resort becomes a template they can largely copy and paste onto the next, which is exactly why focus matters so much at scale. As the visionary, Zander spends his time on strategy, partnerships, larger investors, lenders, and deal negotiation, while his team runs marketing, finance, and operations. Zander's take on imposter syndrome is refreshingly contrarian. He does not really experience it. He holds a vivid vision of the success he is going to have, treats it as the only possible future, and reads any deviation as something to fix or adapt to rather than evidence of doubt. He extends that same clarity to the investors he works with. He does not tolerate status games or negative energy, and he is comfortable saying no to anyone who does not fit the culture, a boundary he admits he did not have at the beginning, when growth made him more flexible. The lesson that cemented it, as Kim knows from her own "gift that keeps on giving" client, is that some relationships simply are not worth the heartache. Zander closes on leadership, drawing a line from the military to the civilian world. The structures differ, but the principle holds: you cannot command people, you have to motivate them. That means giving purpose and direction, building a culture where people are bought into the same mission and values, and then empowering them to own outcomes end to end rather than just ticking off the next task on a list. When something becomes a person's responsibility to make happen, they bring a different level of pride to it. This episode explores: Building a real estate business around a lifelong love of the outdoorsWhy the "multiple income streams" myth is the wrong goal for most peopleHyper-focus as a competitive advantage, and the discipline of cutting the 80%The entrepreneur's curse of seeing opportunity everywhereWhy equity rich and cash poor is real, and the shift from equity to cash flowHiring only A players who are also true culture fitsThe development-group model: buy, improve, expand, operate, repeatHow staying in one asset class makes scaling a copy-and-paste exerciseDoing what makes sense rather than what is normalCarrying military composure and leadership into running a companyChoosing your battles and focusing only on what you can controlReplacing imposter syndrome with a fixed vision of the futureSetting boundaries with investors and saying no to bad-fit moneyLeading by motivation and ownership, not commandThere is a quiet throughline in how Zander moves through the world. The same person who jumps out of planes and dives into underwater caves is also the one preaching focus, constraint, and calm. He has learned that adventure and discipline are not opposites but partners, and that the real freedom he sells to investors is the one he has built for himself: a life where the work, the wealth, and the way he wants to live all point in the same direction. If you are an investor, founder, or leader who feels pulled in too many directions at once, this conversation offers a grounded case for focus, boundaries, and building a business that fits the life you actually want to live. 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: Name: Zander KempfCompany: Clear Summit InvestmentsFocus: Value-add glamping resorts and hot springs near national parks, helping investors pursue financial freedom through unconventional real estateWebsite: https://clearsummitinvestments.com/current-offeringLinkedIn: https://www.linkedin.com/in/alexanderkempf/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

    Why Focus Beats Owning a Little of Everything | Zander Kempf

  3. 20 Oct

    The Second-in-Command Advantage: How a Great COO Lets Founders Scale Without Burning Out | Derek Fredrickson

    In this episode of Unconventional Wisdom About Conventional Wisdom, Kim Miller-Hershon sits down with Derek Fredrickson, founder and CEO of The COO Solution. With over 16 years as a second in command and COO, Derek helps seven and eight figure business owners streamline operations, build high-performing teams, and scale sustainably without burning out. He leads a team of 15 fractional COOs serving companies across many industries. He also happens to be a New England boy who has called Paris home for the past 10 years, a move that he admits makes no sense on paper yet turned out to be exactly right. That Paris story is more than a personal footnote. Derek went virtual with his team back in 2015, a full year before the move and years before "pivot to online" became a pandemic cliché. Living six hours ahead of his US clients forced him to build operations, systems, and communication habits that most businesses only scrambled toward much later. He was, in his own words, ahead of the curve, and the discipline it demanded shaped how he runs everything today. The conventional wisdom Derek followed early on was that his lane was set. He studied business, worked on Wall Street for big investment banks, and believed the corporate ladder was simply what you were supposed to climb. Watching his wife, a business coach, come home lit up by the impact she was having, he realized the corporate track was feeding his bank account but not his sense of mission or purpose. So he took the leap into entrepreneurship, not overnight but after a year of reflection, even with a new house and a third child on the way. He is careful to frame it as his journey rather than a prescription, but for him the pull toward something more meaningful was undeniable. Derek's core leadership insight is that growth requires separating your ego from the engagement. In his early days running The COO Solution, he felt he needed to be in every room, in every client meeting, personally part of every solution. He came to see that instinct as his own old mindset left over from his days as an individual fractional COO. Clients now hire the results, the methodology, and the roster of brilliant COOs he has assembled, not Derek personally. The more he inserted himself, the less room his COOs had to do their best work. Learning to feed his own need for significance without being in the room was, he says, night and day from where he started. That led him to a contrarian belief: business owners are not meant to run their own businesses. Most founders, he argues, build something where the tail wags the dog, slowly becoming the operator of a company they started out of passion. The identity shift from operator to owner frees them to be the rainmaker, the visionary, the relationship builder, which is how companies grow exponentially. You cannot scale, he says, when the founder is still stuck in all the day-to-day. Asked where he still wrestles behind the scenes, Derek is refreshingly candid. His biggest current challenge is a scaling problem he has not solved. His 15 COOs are exceptional, and many of them also serve clients outside his firm, which he genuinely applauds. The rub is consistency. If every COO does the work their own way, the model is not uniform and not scalable, because you cannot scale complexity, only simplicity. Yet clamp down with rigid guardrails and the best COOs feel reduced to project managers. He is still searching for the balance between a shared methodology and enough room for talented people to flex, and he is honest that it remains a work in progress. This episode explores: Why going virtual in 2015 put Derek years ahead of the remote-work curveMoving a New England family to Paris for one year that became tenWhy the contrarian truth is that business owners are not meant to run their own businessesThe identity shift from operator to owner, and why it is the key to exponential growthThe real, unsolved challenge of scaling a team of brilliant, independent COOsWhy you can scale simplicity but never complexityOvercoming the belief that you are "not a salesperson"Reframing selling as providing an opportunity, not applying pressureWhy people love to buy even when they resist being soldQuieting the imposter voice by selling the collective, not yourselfHow better questions often matter more than direct experienceWhy the fundamentals of leadership stay the same no matter the revenueThere is something quietly instructive in how Derek holds success and uncertainty at the same time. He has built a scalable firm, moved his life across an ocean, and conquered a fear of selling, yet he speaks openly about the problem he has not cracked and the voice that still whispers doubt. That honesty is the point. Growth, for him, is less about arriving and more about continually separating what is truly yours to own from what is not, in business and in life. 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: Name: Derek FredricksonCompany: The COO SolutionFocus: Fractional COO services helping seven and eight figure business owners streamline operations, build high-performing teams, and scale sustainablyWebsite: https://thecoosolution.com/LinkedIn: https://www.linkedin.com/in/derekfredrickson/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

    The Second-in-Command Advantage: How a Great COO Lets Founders Scale Without Burning Out | Derek Fredrickson

  4. 16 Oct

    From J.P. Morgan to Cannabis Fintech: Leading Without Carrying It All | Aubrey Amatelli

    In this episode of Unconventional Wisdom About Conventional Wisdom, Kim Miller-Hershon sits down with Aubrey Amatelli, founder and CEO of Payrio, a fintech company providing payment solutions for cannabis, alternative medicine, and other highly regulated industries. Before founding Payrio, Aubrey spent more than a decade at J.P. Morgan Merchant Services, rising to executive director of commercial banking, specializing in technology and disruptive commerce in Silicon Valley. She also serves as chair of the National Cannabis Industry Association's Banking and Finance Services Committee for the 2025-26 term. A devoted Burner, she opens the episode sharing how Burning Man (which she treats as her new year, a time to reset and pour self-love back into herself) grounds someone who works in finance in a place where, for two weeks, no money changes hands at all. In this conversation, Aubrey challenges a piece of conventional wisdom she carried straight out of J.P. Morgan, the Harvard of payments: that being a founder means being the hardest worker in the room, carrying everything yourself, and wearing the most-hours badge. She's a relentless worker, but she's learned that badge doesn't mean anything anymore. Real leadership is leading with efficiency and the right team, and real success has shifted from "I started this working 20 hours a day" to freedom, time with her three kids and room for others in her organization to step up and feel like leaders themselves. A rich thread is the limits of the founder-as-expert myth. Aubrey knows what she knows (payments, compliance, how funds flow) cold, but she didn't grow up at J.P. Morgan learning marketing, HR, SEO, operations, and reporting, and she doesn't know anyone who's an expert in all of it ("maybe Claude"). Kim reinforces the balance she coaches constantly: you don't need to become a CFO to be a good CEO, but you don't get a free pass on your finances either, you have to know enough to be sure things are kosher. They land together on the strengths-over-weaknesses reframe, if you pour all your energy into your weaknesses you just get stronger weaknesses, so build on your strengths and hire for the rest. Her biggest current challenge is managing rapid growth, especially in the fast-expanding peptide world, as a solo founder with no one above her to run decisions by. She wants to hire efficiently without over-hiring and eroding the margins that keep Payrio profitable, and much of it comes down to trusting her intuition, moving, and course-correcting rather than falling into analysis paralysis. She and Kim dig into mistakes as the source of the biggest learnings (you didn't know it was a mistake at the time, but you tie your shoelaces tighter next time), and into the practice of challenging the story you tell yourself with curiosity rather than just correcting the behavior. Aubrey's version is the muscle she keeps exercising: intuition, that quiet "pause" that she's learned to honor, because nobody knows you better than yourself, right down to the voice that told Kim to finally put on an apron before cooking. This episode explores: Why the most-hours badge of founder honor means nothingRedefining success as freedom, not hustleSlowing down a fast launch, and hiring to make yourself do itWhy no founder is an expert at everythingKnowing enough about finance without becoming the CFOBuilding on strengths and hiring for weaknessesManaging rapid growth without over-hiring or analysis paralysisTurning mistakes into the biggest learningsChallenging the story you tell yourself with curiosityTrusting intuition as a muscle you strengthen over timeLeading with heart and relationships over the bottom lineSurrounding yourself with people who share your valuesReframing imposter syndrome as a complimentJust saying "thank you," and letting a compliment landAubrey's perspective is a powerful reminder that you don't have to be the hardest worker, the expert in everything, or the founder who chases margins to build something that lasts, you have to trust your intuition, lead with your heart, and surround yourself with the right people. Her journey from executive director at J.P. Morgan to the founder of a profitable, award-nominated fintech serving the businesses no one else will shows that doing genuine good for your customers can be the smartest growth strategy of all. If you're a founder, leader, or anyone building something in an industry everyone else overlooks, this conversation offers practical insight, honest talk about intuition and imposter syndrome, and a refreshing case that leading with heart and simply saying thank you will take you further than you think. 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: Aubrey Amatelli, Founder & CEO, PayrioFocus: Fintech payment solutions for cannabis, alternative medicine, peptides, and other highly regulated industries; former executive director at J.P. Morgan Merchant Services; chair of the NCIA Banking and Finance Services Committee (2025-26)Website: https://www.payrio.co Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

    From J.P. Morgan to Cannabis Fintech: Leading Without Carrying It All | Aubrey Amatelli

  5. 13 Oct

    Rocketman to Movie Set Medic — How high-risk flying led to building National Set Medics Dan Schlund

    In this episode of Unconventional Wisdom About Conventional Wisdom, Kim Miller-Hershon sits down with Dan Schlund, the Rocket Man himself, a world-renowned jet pack pilot, stunt man, and award-winning author, and the subject of the forthcoming documentary The Last Rocket Man, based on his memoir of the same name. Dan spent a decade flying rocket belts across 25 countries and six continents, over 100 feet in the air and up to 85 miles an hour, while surviving devastating skin graft surgeries and a broken neck. When he had to pivot, he founded National Set Medics, a company that provides medics to TV shows, films, and events nationwide, and grew it into a multi-million-dollar business over ten years. His memoir recently won Best Memoir at the 2026 New York City Big Book Awards. In this conversation, Dan challenges a piece of conventional wisdom that weighs on anyone cast as the expert: that you always have to have the answer and the plan. He used to burn enormous mental energy war-gaming every possible direction a problem could go. What freed him was learning to simply say "I don't know, but I'll figure it out," which focuses your attention on the actual issue instead of performing certainty. As he puts it, most of the time he doesn't know exactly what to do, he's just very good at figuring it out. Kim connects it to a current trap: people now think they can fake the answer because they can ask an AI, and she's candid from building her own custom agent workforce that AI can send you down wildly wrong paths if you abdicate your own thinking. Dan's version is clean: AI has a lot of information but it's not intelligent and it can't read your mind, so you still have to put your own brand on it. Dan's whole origin story is a case study in scrappiness. He started as a live-action stunt performer (getting shot off roofs and set on fire thousands of times as Batman, Indiana Jones, and cowboys at theme parks), met rocket-belt creator Kenny Gibson, and was selected to become one of the few Rocket Man pilots. After his 2013 crash and broken neck, he asked himself what his passion was, became a paramedic, and spotted a niche no one was serving well: film and TV sets legally require medics, and he knew both the entertainment side and the medical side. There was never a business plan. He threw his name out to producers, got double-booked, started splitting jobs with other medics, and realized he could earn a percentage on every medic he placed. National Set Medics now has 13,300 registered medics nationwide, and Dan describes his real job as balancing two customers, the medics and the producers, so that at the end of every day, everyone goes home alive. This episode explores: Why "I don't know, but I'll figure it out" beats faking the answerWhy AI can point a direction but can't replace your own thinkingSpotting an underserved niche by combining two kinds of expertiseBuilding a business with no plan, one working chunk at a timeTesting a category, then pivoting when it doesn't get tractionWhy shotgunning the whole market drains your resourcesSticking to your bread and butter before adding a second thingBalancing two sets of customers so everyone goes home aliveTiming a launch: packaging news instead of doubling the workContaining your own excitement as the real disciplineTreating every decision (and hire) as asset vs. liabilityEmbracing imposter syndrome by building a team and not micromanagingLetting managers lead in their own style, not yoursBeating anxiety by focusing on successes, not failuresIf you're a founder, creative, or anyone who's ever been told you need a plan before you can start, this conversation offers practical insight, honest talk about anxiety and imposter syndrome, and a refreshing case that figuring it out as you go is its own kind of genius. 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: Dan Schlund, "The Last Rocket Man"Book: The Last Rocket Man (memoir, Best Memoir, 2026 New York City Big Book Awards), available on AmazonDocumentary: The Last Rocket Man (coming 2027)Company: National Set MedicsWebsite: https://rocketman.tv Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

    Rocketman to Movie Set Medic — How high-risk flying led to building National Set Medics Dan Schlund

  6. 9 Oct

    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

  7. 6 Oct

    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

  8. 2 Oct

    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
See All (118)

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