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

    The Second-in-Command Advantage: How a Great COO Lets Founders Scale Without Burning Out | Derek Fredrickson
    2026/10/20
    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/...
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    38 分
  • From J.P. Morgan to Cannabis Fintech: Leading Without Carrying It All | Aubrey Amatelli

    From J.P. Morgan to Cannabis Fintech: Leading Without Carrying It All | Aubrey Amatelli
    2026/10/16
    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: ...
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    36 分
  • Rocketman to Movie Set Medic — How high-risk flying led to building National Set Medics Dan Schlund

    Rocketman to Movie Set Medic — How high-risk flying led to building National Set Medics Dan Schlund
    2026/10/13
    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.
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    34 分
  • You’re More Ready Than You Think: Why You Don’t Need It All Figured Out to Start | Liz Mbwambo

    You’re More Ready Than You Think: Why You Don’t Need It All Figured Out to Start | Liz Mbwambo
    2026/10/09
    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 ...
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    39 分
  • Why You Don't Have to Tear It Down to Modernize a Legacy Business | Chad Bauer

    Why You Don't Have to Tear It Down to Modernize a Legacy Business | Chad Bauer
    2026/10/06
    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 ...
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    46 分
  • Stop Shrinking Yourself: On Owning Who You Are Later in Your Career | Victoria Woods

    Stop Shrinking Yourself: On Owning Who You Are Later in Your Career | Victoria Woods
    2026/10/02
    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.
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    43 分
  • Work Smart, Not Hard: The 80/20 Reframe That Changed How She Runs Her Business | Cherry Lao

    Work Smart, Not Hard: The 80/20 Reframe That Changed How She Runs Her Business | Cherry Lao
    2026/09/29
    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 ...
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    41 分