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Most personality tests tell you how someone behaves. Very few tell you why. In this episode of the Business Legacy Podcast, Paul Dio sits down with Karl Hebenstreit of Perform and Function, a leadership development consultant and executive coach who uses the Enneagram to help leaders understand the motivation driving their own behavior and the behavior of the people around them. Paul opens with a personal story. Early in his career, personality assessments told him he was too patient, too introverted, and not aggressive enough to succeed as a financial advisor. Instead of walking away, he built a business around his personality one relationship at a time. Karl explains why that matters: an assessment cannot tell you what you know to be true about yourself, and passion paired with self awareness will often outperform natural talent without it. Karl shares how he discovered the Enneagram while pursuing a PhD in organizational psychology, when his professor invited Helen Palmer to teach a single class. He then walks Paul through all nine types live on the show, organized into thinking, feeling, and action styles, and together they land on Paul's core motivation. Karl's Swiss Army knife analogy reframes the whole system: we each favor a few tools, but all nine are available to us, and growth comes from learning when to open the ones we rarely use. The conversation turns to leadership and succession. Karl explains why the person ranked first on a succession plan is often not the one who gets the role, why real one on one conversations about aspiration matter more than development programs, and how similar to me bias leads leaders to choose successors who think exactly like them. His point is simple and uncomfortable: the team you need is the one that covers your blind spots, not the one that mirrors you. Timestamps 00:00 Welcome and introduction to Karl Hebenstreit 00:30 Paul's personality test story and building a business around his style 02:30 Why passion and self awareness outweigh an assessment 04:00 From Myers Briggs and DISC to the Enneagram 05:00 Behavior versus the motivation behind it 06:00 Meeting Helen Palmer in a single graduate class 07:00 The nine motivations and the three centers 08:00 Thinking styles, types five, six, and seven 10:30 Feeling styles, types two, three, and four 13:00 Action styles, types eight, nine, and one 15:30 Paul's styles and the Swiss Army knife analogy 17:00 Identifying Paul's core motivation 18:30 Small talk, authenticity, and recharging 20:00 Handing leadership to someone wired differently 21:00 Why the top succession candidate is often skipped 22:30 Real versus fake succession plans 23:30 Similar to me bias and diversity of perspective 25:00 How underused types show up in our mistakes 26:30 Karl's favorite part of the work 27:30 Where to connect with Karl Episode Resources Learn how Carl helps leaders and teams uncover the motivation behind their behavior, strengthen relationships, and make smarter decisions about who leads next: https://www.performandfunction.com Leave a Review: If you enjoyed the episode, leave a review and rating on your preferred podcast platform. For more information: Visit https://businesslegacypodcast.com to access the show notes and additional resources on the episode.

The fashion industry has a trust problem. Consumers are no longer sure what their clothes are made of, whether sustainability claims are real, or whether the brands they buy from are telling the truth. In this episode of the Business Legacy Podcast, Paul Dio sits down with Rachel Erickson, CEO and founder of Unmarked Street and The Business of Apparel, to talk about what it takes to bring kindness, transparency, and accurate information back into an industry that has been questioned for years. Rachel and her team spent more than a decade each inside major corporate fashion brands before building their own company. Unmarked Street is their done for you product development agency, handling fit, factory documentation, and contracts for smaller apparel brands. The Business of Apparel is their mentorship and coaching arm, created because so much of the information available to new founders online is simply wrong. The conversation covers where the mistrust began, from the rush toward sustainability without regulation to the greenwashing lawsuits that followed. Rachel then lays out the order of operations every new apparel founder should follow: target customer first, budget second, product creation third. She makes the case that creativity only survives when the margins are healthy, and she challenges consumers and brands alike to measure value by cost per wear rather than cost per garment. Rachel's deepest passion is fit, and she explains why it is the fastest path to a loyal customer base. She shares how her team solved a running short fit issue in two rounds after a brand had struggled through five or six prototypes, and how one client built her size charts by personally measuring her ideal customers. On legacy, Rachel wants to be remembered as the person who opened the door for apparel founders, and on a personal level, she is close to her goal of retiring her husband. Timestamps 00:00 Welcome and introduction to Rachel Erickson 00:45 Bringing trust back into the fashion industry 02:00 Unmarked Street and The Business of Apparel 03:00 Where the mistrust in fashion started 05:00 Greenwashing, plastic, and what our clothes are made of 06:00 Where new apparel founders should begin 07:00 Target customer first 08:00 Why budget comes before design 09:30 Balancing creativity, originality, and profitability 11:00 Cost per wear versus cost per garment 12:30 Selling to the parent, not the kid 13:30 Paul's progress over perfection hat 15:30 Rachel's passion for fit and pattern engineering 17:00 Solving a running short fit in two rounds 18:30 Why great fit builds loyal customers 20:00 The new Wild Rye collaboration 21:00 Inventory waste and bad fit 22:00 Why there is no standard sizing 23:30 Building size charts by measuring real customers 25:00 Gratitude for her husband and team 27:00 Professional and personal legacy 28:30 Where to connect with Rachel Episode Resources Explore how Rachel helps apparel founders build profitable, trustworthy brands with the right information, the right fit, and the right foundation from day one: https://thebusinessofapparel.com Leave a Review: If you enjoyed the episode, leave a review and rating on your preferred podcast platform. For more information: Visit https://businesslegacypodcast.com to access the show notes and additional resources on the episode.

Discover the transformative journey from corporate finance to entrepreneurial success with Shanli Liu, founder of Freedom Folio. What if leaving a steady career could lead to a more fulfilling life and business? Shanley's story is a testament to resilience and the power of personal connections, tracing her path from a childhood fundraising event in China to establishing her own CPA practice in Boston. The episode offers a candid look at the pivotal moments that fueled her transition, including learning from a seasoned CPA and leveraging her corporate experience to launch her own firm after motherhood inspired a new direction. Learn how tax planning can elevate your practice management strategies with insights from Shanley's collaboration with POSBOT and her mentor, Tyler Thompson. The episode explores her evolved mindset from merely fulfilling tasks to embracing the entrepreneurial spirit, emphasizing the importance of strategic client selection and holistic tax planning. Shanley's experiences underscore the necessity of educating clients about tax complexities and the pitfalls of fragmented approaches. Discover practical solutions for scalable client education that combat industry-wide misinformation, ensuring both practitioners and clients are aligned in achieving financial success. Explore the balancing act of entrepreneurship and personal life, as Shanli addresses the challenges of setting boundaries. Through personal anecdotes, including the extreme of taking a client call during labor, the conversation sheds light on the pressures faced by professionals, particularly women, in juggling work and family. Drawing inspiration from Tim Urban, the discussion highlights the need to prioritize family time amidst professional commitments. This episode is a heartfelt reminder of the importance of boundaries to prevent burnout and ensure you remain present for those who matter most. Timestamps 00:00:00 - Introduction and Welcome to the Podcast: Shanli Liu's Journey 00:00:12 - Shanley's Early Life and Inspiration from China 00:02:05 - Transition from Corporate Finance to Entrepreneurship 00:03:30 - Founding Freedom Folio and Building a CPA Practice 00:06:45 - Balancing Motherhood and Entrepreneurship 00:09:15 - Importance of Learning to Say No in Business 00:11:37 - Embracing Entrepreneurial Mindset through Tax Planning 00:12:45 - Lessons from POSBOT and Training with Tyler Thompson 00:14:30 - Strategic Client Selection for Scalable Tax Planning 00:16:10 - Addressing Fragmented Tax Planning and Client Education 00:18:27 - Holistic Financial Planning for Small Business Owners 00:19:30 - Collaborating with Financial Advisors for Diversification 00:21:00 - Setting Boundaries to Maintain Work-Life Balance 00:22:36 - Challenges of Overworking and People-Pleasing 00:24:00 - Societal Pressures on Women Entrepreneurs 00:25:30 - Reflection on Family Prioritization and Tim Urban's Work 00:27:00 - Conclusion: Aligning Professional Success with Personal Well-being Episode Resources: Connect with Shanli here: https://www.linkedin.com/in/shanli-liu-234b16b/ Legacy Podcast: For more information about the Legacy Podcast and its co-hosts, visit businesslegacypodcast.com. Leave a Review: If you enjoyed the episode, leave a review and rating on your preferred podcast platform.

In this episode of Business Legacy Podcast, Paul Dio sits down with Seth Kamens, founder of Kamens CPA, for a conversation that is as refreshingly honest as any the show has produced. Seth didn't set out to build a twenty-five-person accounting firm. He set out to keep the lights on. What he built instead — starting with fifteen clients from his father, a solo practice, and a profile on Thumbtack — has exceeded every expectation he ever had for himself. And when Paul asks him about legacy, Seth laughs and says he doesn't care. His legacy is being a good dad. The rest, in his words, is b******t. Seth traces the unusual path that brought him to accounting — Capitol Hill ambitions, investment banking, asset management, financial planning — and explains why he hated working at the big firms. The clients who weren't top tier were treated as second class. The work was compliance and regurgitation. Nobody was asking the five or six questions that actually move a business forward. Seth decided he could do it differently, and in 2012, with his father's referrals and a depleted bank account, he started. The heart of the conversation is what it means to be a proactive accountant rather than a reactive one. Seth explains why he turns down clients he can't actually help, why he thinks of himself as a business owner who happens to do accounting rather than the other way around, and why his firm's success — built entirely on networking and word of mouth, never a dollar of SEO — comes down to one thing: showing clients that someone gives a damn. The episode closes with the kind of honesty that's rare on business podcasts. Seth on the $200,000 error he caught that the bigger firm missed for three straight years. On why the accounting industry is commoditized and what that means for how you prove value. On building a leadership culture that's the opposite of Deloitte, JH Cohen, and Merrill — encouraging, accountable, and never humiliating anyone in front of their peers. And on the legacy question that made him laugh — because in ten or twelve years when he sells, not ten percent of his clients will remember his name, and he is completely fine with that. Timestamps 00:00 — Welcome and introduction 00:45 — The generalist's unusual path to accounting 02:30 — Why he hated the big firms and what a proactive CPA actually looks like 04:30 — Fifteen clients, a depleted bank account, and Thumbtack 06:00 — The entrepreneur who happens to be a CPA 07:30 — How the clientele has evolved over fifteen years 09:30 — Accountants as cost centers and repositioning the conversation 12:00 — The aha moment that keeps him going 14:00 — The psychology of gains, tax bills, and client blame 16:00 — Commoditization and how to prove your value anyway 18:00 — Navigating the ever-changing tax code 20:00 — The $200,000 error the big firm missed three straight years 22:30 — We've never spent a dollar on SEO 24:00 — Leadership as the opposite of Deloitte and Merrill 27:00 — Making mistakes, not personalizing them, and building culture 29:00 — Goals, ambition, and already exceeding every expectation 31:00 — How a stuck CPA redesigns their practice 34:00 — My legacy is being a good dad 36:00 — Where to find Seth and Kamens CPA Episode Resources Discover how Seth and his team at Kamens CPA help business owners, entrepreneurs, and individuals get proactive answers to the questions most accountants never think to ask — and how they've built a twenty-five-person firm entirely on referrals and the idea that someone should actually give a damn: www.kamenscpa.com Leave a Review: If you enjoyed the episode, leave a review and rating on your preferred podcast platform. For more information: Visit https://businesslegacypodcast.com to access the show notes and additional resources on the episode.

In this episode of Business Legacy Podcast, Paul Dio sits down with Heather Beverly an entertainment attorney, author, and founder of both the Law Offices of Heather Beverly and Soul Reciprocity — for a conversation that starts in a closet in California and ends somewhere much deeper. Heather has spent twenty-five years protecting and preserving the creative legacies of artists, producers, songwriters, and entrepreneurs. The book she eventually wrote, though, was about the legacy she almost lost sight of — her own. The episode opens on a moment that sounds small and isn't. Heather was about to take a before photo in her workout clothes when she zoomed in on her face and didn't recognize the person looking back. Not because of weight or appearance — but because the woman she believed herself to be wasn't there. What followed was a five-year journey back to self that involved therapy, retreats, journaling, honest conversations with friends, the end of a marriage, a cross-country move, and the slow, uncomfortable work of auditing every relationship in her life against a phrase she thought she'd heard somewhere but had actually coined herself — soul reciprocity. Heather walks Paul through what that phrase actually means. Not things, not grand gestures — the quality of being seen, truly seen, by the people closest to you. The feeling of sowing into the world and having the world give something back. She explains why she'd lost it, how she found it again, and what she changed to protect it — including the inner circle audit that shifted people in and out of her closest orbit, the Moroccan room she created to sit and see trees instead of just her desk, and the permission she now gives herself to sleep in without apologizing. The conversation closes on where Heather is now — engaged to someone she's known for thirty years and dated twice before, surrounded by a soul tribe that shows up before she even knows she needs them, and building something that carries the same philosophy as her law practice into a broader conversation about how all of us choose the people we let into the rooms that matter. Timestamps 00:00 — Welcome and introduction 00:45 — Twenty-five years protecting other people's creative legacies 02:30 — Direction as a North Star instead of a definitive path 04:00 — Waking up not knowing who you are 06:00 — The Instagram life that felt empty 07:30 — The before photo in the California closet 10:00 — The five-year journey back to self 12:30 — The phrase she thought she'd heard somewhere 14:00 — What soul reciprocity actually means 16:30 — Sowing into the world and feeling depleted 18:00 — The questions you have to be honest enough to answer 21:00 — What freedom really feels like 22:30 — Changing everything — marriage, city, inner circle 25:00 — The inner circle audit 27:00 — Which version of you shows up in a relationship 29:00 — Staying present through change 31:00 — The soul tribe that shows up before you need them 32:30 — Three point forever — getting married in January 2027 34:00 — Where to find Heather, the book, and Soul Reciprocity   Episode Resources Discover Heather's work at the intersection of entertainment law and personal legacy — protecting creative works and preserving the lives that matter most — and explore the world of soul reciprocity, her book, and the philosophy that the people in your circle should reflect who you are and where you're going: www.soulreciprocity.com Leave a Review: If you enjoyed the episode, leave a review and rating on your preferred podcast platform. For more information: Visit https://businesslegacypodcast.com to access the show notes and additional resources on the episode.

In this episode of Business Legacy Podcast, Paul Dio sits down with Daniel Boettcher, founder of The Intrepid Wendell, for one of the most quietly extraordinary conversations the show has produced. Daniel is an attorney, a gemologist, a polyglot, and a jeweler — not because he planned to be, but because an illness redirected a career pointed at the U.S. State Department, and a bitterly cold February day in Antwerp introduced him to the diamond trade through a private club above a cigar lounge. Daniel explains what he actually does, and it takes a minute to fully land. He doesn't just make jewelry. He listens to someone's history — their loves, their losses, their origin stories, the things they want to reach across time to say — and then he represents that history in an object. The pilot who wanted to divide his ring into four pieces, one for each child, so that the thing that touched his skin every day could touch theirs after he was gone. The couple who met in a sunflower field in Kansas and knew immediately — her engagement ring is a sunflower, because sunflowers always point toward the light even on an overcast day. The conversation moves through Daniel's remarkable range. Growing up a polyglot and the way different languages carry different flavors — Spanish for emotion and poetry, English for calendars and formulas, and the Spanglish of Puerto Rico squishing both together into something new. The challenge of getting clients to trust him with their histories, because the histories are where the real work begins. The ocean crossing from Tokyo to Anchorage he took in May that gave him the vertical perspective he needs to stay functional in a scatterplot life. The episode closes on legacy — both the one Daniel builds for others and the one he's quietly building for himself. A mentorship philosophy. A preservation organization he's starting in Old San Juan to privately fund the repair of bronze sculptures and 1892 tablets that the politics of historic preservation keep leaving unattended. He doesn't need his name on it. He just wants the statues to still be there. Timestamps 00:00 — Welcome and introduction 00:45 — The plan that was interrupted by illness 02:30 — Antwerp, a cigar lounge, and the diamond bourse 04:00 — Jewelry as representation of personal history 06:00 — Paul's wife's ring turned into a daughter's necklace 07:00 — The pilot's ring that comes apart in four pieces 10:00 — The challenge of earning client trust and opening the well 12:30 — What it means to make a piece that could only belong to one person 14:00 — The sunflower ring and the Kansas City couple 17:00 — Being a polyglot and the flavors of different languages 20:00 — Spanglish in Puerto Rico 22:00 — Languages as keys to legacy 23:00 — Motivation and the scatterplot life 24:30 — The Pacific Ocean crossing as a vertical reset 26:00 — Only control what's yours 27:00 — Legacy as professing love and treating people well 28:00 — Mentorship and the cost of short job tenures 29:30 — San Juan Preserva and the 1892 tablets 31:00 — Where to find Daniel and The Intrepid Wendell Episode Resources Discover how Daniel helps clients turn personal histories, origin stories, and the people they love into one-of-a-kind pieces of jewelry that could only belong to one person — and carry on long after they do: www.theintrepidwendell.com Legacy Podcast: For more information about the Legacy Podcast and its co-hosts, visit https://businesslegacypodcast.com Leave a Review: If you enjoyed the episode, leave a review and rating on your preferred podcast platform. For more information: Visit https://businesslegacypodcast.com to access the show notes and additional resources on the episode.

In Episode 274 of the Business Legacy Podcast, Paul Dio sits down with Daniel Scola Jr., managing partner of Hoffmann & Baron, for a wide-ranging conversation about intellectual property, the widening trust gap in modern communication, and the human judgment that no AI system will replace anytime soon. Daniel has spent his career at the intersection of law, science, and inventors, and the perspective he brings to the current AI moment is one every founder building something original should hear. Daniel opens by naming a problem most professionals feel and few articulate — the human connection has quietly drained out of business communication over the last fifteen years, and along with it, the ability to build the trust real client relationships depend on. Emails, texts, and voicemails are missing the subtlety of in-person work, and Zoom, while useful, still can't fully replace being in the same room reading a face. The heart of the episode is intellectual property — and specifically, the moments an entrepreneur most needs to think about it. Daniel walks Paul through the most common mistake founders make (talking about their idea without an NDA and losing patent rights the moment it becomes public), the story of his own father — an inventor whose formulas were stolen, which is the reason Daniel became a patent attorney in the first place — and the current live question of how patent, trademark, and copyright law apply to AI-generated work. AI cannot be an inventor. AI outputs sit in an unsettled corner of copyright law. And the hundreds of pending training-data cases across the New York-New Jersey and Northern California corridors are quietly writing the rules everyone will live under next. Daniel closes with something more personal — three kids under three when he was starting the firm, ten years of a punishing schedule, and the moment he chose not to correct his son's baseball swing and instead pointed him at Albert Pujols. It's a fatherhood story that also happens to be a client-work philosophy — help people focus on what's working, not what's broken, and let self-correction do the rest. Timestamps 00:00 — Welcome and introduction 00:45 — The trust deficit in modern communication 02:30 — Why human contact still builds client relationships 04:00 — The client who wouldn't listen and the professor who came back 07:30 — The most common IP mistake early founders make 09:00 — Why the off-the-internet NDA usually isn't enough 10:30 — The father-inventor story that made him a patent attorney 13:00 — When copyright rights actually begin 14:00 — George Harrison and "My Sweet Lord" 15:30 — Why trademarks are about the public, not the owner 17:00 — AI cannot be an inventor 18:30 — AI in trademark naming vs. copyright output 20:00 — The pending fair-use cases across the U.S. corridors 22:00 — Never put confidential work into open ChatGPT 23:30 — Accountability as the line between AI and human counsel 24:30 — The AI musician question 26:00 — Reading a judge, and what Zoom can't show 28:00 — Fatherhood, three kids under three, and a ten-year grind 31:00 — Coaching baseball and choosing time with family 32:30 — Client and kid personalities — one negative comment sticks 34:00 — The Albert Pujols swing story 35:30 — Where to find Daniel and Hoffmann & Baron Episode Resources Discover how Daniel and his team at Hoffmann & Baron help inventors, founders, and companies protect what they've built through patents, trademarks, copyrights, and the operational counsel that keeps ideas in the right hands from day one: www.hbiplaw.com Legacy Podcast: For more information about the Legacy Podcast and its co-hosts, visit https://businesslegacypodcast.com Leave a Review: If you enjoyed the episode, leave a review and rating on your preferred podcast platform. For more information: Visit https://businesslegacypodcast.com to access the show notes and additional resources on the episode.

Paul sits down with Dr. Jim Taylor — performance psychologist, former U.S. Ski Team competitor, and founder of Prime Mind for a conversation that traces a career built on a single insight. The mind is the final frontier, and almost none of us know how to work it. Jim's origin story is disarmingly honest. He was a good ski racer with a bad head, the kind coaches used to call a head case. One summer psychology course in high school changed the trajectory of his athletic career, and eventually his entire life. He walks Paul through what actually changed that season (not the strength, not the technique, the internal architecture) and why he decided somewhere around age nineteen that psychology hadn't been a choice so much as a calling. The heart of the conversation is the mental work Jim now teaches. Confidence isn't a skill, it's a muscle. Visualization isn't a nice-to-have — the primitive mind can't tell the difference between an imagined rep and a real one, and Jim used that mechanism to rewire his own belief system on the way to an international-level career. Resilience is fundamentally a perception problem. And the "good road / bad road" fork, he says, is often not a conscious choice at all — which is why most people stay on the bad road even when they know exactly where it ends. The episode's emotional center is the weight vest metaphor. Jim describes what happens when an athlete steps into competition carrying twenty pounds of expectation, identity, and self-worth on their shoulders. He walks through Alyssa Liu's Olympic story as an example of what the release actually looks like, opens up about his recent decision to walk away from a startup he'd invested two years into, and unveils the app-based extension of his practice Prime Mind that he built in the two-and-a-half months since he left. It closes on a legacy answer that quietly matches Paul's own help people see themselves before they know how to see themselves.   Timestamps 00:00 — Welcome and introduction 00:30 — The head case origin story 02:00 — The summer course that changed everything 03:30 — The breakthrough season on the U.S. Ski Team 05:00 — Middlebury, Psych 101, and the calling 06:30 — Purpose and passion as a fill-in-the-blank question 08:00 — Why startup building feels riskier than skiing 09:30 — Network, credibility, and the ski racing runway 11:00 — Performance psychology beyond sport 12:30 — Confidence, self-talk, and mental imagery 14:00 — The primitive mind and positive reps 15:30 — Rewiring belief through visualization 17:00 — Resilience as a mental muscle 18:30 — The good road and the bad road 20:00 — Post-medal letdown and identity loss 21:30 — Athlete to performer identity shift 23:00 — Alyssa Liu and the weight vest release 25:00 — Toxic sports cultures 26:00 — Walking away from a two-year startup 28:00 — Building Prime Mind solo in ten weeks 30:00 — The B2C and B2B model 31:30 — Favorite client stories and the mind as final frontier 33:00 — Legacy as long game 34:00 — Where to find Dr. Jim and Prime Mind Episode Resources Discover how Dr. Jim Taylor helps athletes, executives, performers, and high-achievers of every kind take the weight vest off and access the mental muscles that make peak performance sustainable — through one-on-one work, keynote and workshop content, and his new app Prime Mind: www.drjimtaylor.com Legacy Podcast: For more information about the Legacy Podcast and its co-hosts, visit https://businesslegacypodcast.com Leave a Review: If you enjoyed the episode, leave a review and rating on your preferred podcast platform. For more information: Visit https://businesslegacypodcast.com to access the show notes and additional resources on the episode.

In this episode, Paul Dio sits down with Jason Bagley, founder of Growth Experts, joining all the way from Cape Town, South Africa. Jason's story is a study in what happens when a marketer stops selling deliverables and starts selling outcomes. He started as a software developer, moved into web design at the exact moment Squarespace and Wix turned it into a race to the bottom, pivoted to a newsletter-only business, sold that during COVID, and eventually landed on the model he's running today — an all-you-can-eat growth marketing agency where the team doesn't just write the thing, they get the thing live. The heart of the conversation is a single insight Jason had with his very first Copy Check client. He'd written a newsletter and expected feedback on the copy. What he got back was a question about MailChimp. That's when the penny dropped. Clients don't want the newsletter written. They want the newsletter sent. They want the landing page built and live. They want the LinkedIn post published. Jason built Growth Experts around that reframe and it's changed how his agency shows up for every client since. Jason and Paul dig into what actually makes a newsletter worth reading in 2026 (spoiler — content, not cadence), how AI is changing what a small team can ship, and why he keeps telling his team to stop asking for sign-off on the work that isn't mission critical. He also gets honest about the mid-growth phase of his own business — the part nobody puts on LinkedIn — where the challenges get harder even as the numbers get better. The episode closes on attention and legacy. Jason's read on where audience attention is moving is simple. It's moving toward honest people doing real things and showing the mistakes. And his legacy is smaller and more personal than most guests give — his wife first, his kids second because of that, and the entrepreneurs he mentors through EO, planting seeds that go on to change worlds he'll never see. Timestamps 00:00 — Welcome from Cape Town 00:45 — Software developer to web design agency 02:00 — The race to the bottom in websites 02:45 — Pivoting to newsletters only 03:30 — Building and selling Firing Squad 04:30 — Launching Copy Check with zero clients 05:30 — The MailChimp question that changed everything 06:30 — Building Growth Experts around outcomes not deliverables 07:45 — Early clients and the cold email skill 09:00 — What actually makes a newsletter worth reading 10:30 — The anchor client from the IT retailer 12:00 — What separates one agency from another in a crowded market 13:00 — High-agency teams and the sign-off tax 14:45 — Latency between idea and execution 16:00 — Building things again thanks to AI 17:00 — Why leaders have to show AI steps first 18:00 — Where attention is moving in a crowded market 19:30 — Video, honesty, and being over the weekly hype cycle 21:00 — The mid-growth phase nobody puts on LinkedIn 22:30 — Leading a team without micromanaging 23:30 — Legacy starts with his wife 24:30 — Mentoring through EO and planting seeds 25:30 — Where to find Jason Episode Resources Discover how Jason and his team at Growth Experts run an all-you-can-eat growth marketing agency built on a simple idea — clients don't want the newsletter written, they want it sent, live, published, and tracked: www.growthexperts.co Legacy Podcast: For more information about the Legacy Podcast and its co-hosts, visit https://businesslegacypodcast.com Leave a Review: If you enjoyed the episode, leave a review and rating on your preferred podcast platform. For more information: Visit https://businesslegacypodcast.com to access the show notes and additional resources on the episode.

In this episode, Paul Dio sits down with Jennifer Lehman, founder of Forward Thinking, for a conversation that starts on a golf course and ends up somewhere much deeper. A conference champion at Campbell University with a communications degree and a Class A professional status with the PGA of Canada, Jennifer built a consulting career after being told, over and over, that she was overqualified for the marketing jobs she was applying for. Twenty years in, she says she's grateful every one of them turned her down. The parallels between golf and business run all the way through the episode. Jennifer makes the case that both worlds are full of people selling quick fixes — the eight-hundred-dollar driver, the make-you-a-million-in-thirty-days marketing program — and neither of them work without a foundation. Her job, whether she's coaching a swing on the range or coaching a business through a growth cycle, is to build something the client can actually sustain. She takes Paul through some of the pivotal chapters of her career. Her very first client was a regional science fair. Her second was an inspiring insurance brokerage owner who let Jennifer push back on her marketing plan in their first working meeting — and then hired her, kept her for years, and eventually sold the business for every dollar and every employee protection she'd asked for. Jennifer also opens up about the ten-year moment when a powerful opponent decided to come after her personally, and the counselor who asked the question that reframed her career — what if you're good enough the way that you are? The conversation lands on legacy. Jennifer wrote two books, has been building a speaking practice, and wants to reach the entrepreneurs who are quietly listening to a little voice telling them something bigger is possible. Her definition of legacy is simple. Leave the world better for having been there. Get good information into the hands of people who can use it. Be in the trenches. Tell them, honestly, that they're closer than they think. Timestamps 00:00 — Welcome and introduction 00:45 — Campbell University, golf, and a communications degree 02:00 — Being told she was overqualified 03:30 — Coaching golf, the mental game, and the crossover into business 05:00 — Why there's no quick fix in marketing 06:30 — The regional science fair as her first client 07:45 — Meeting the insurance brokerage owner and pushing back on the plan 09:30 — A decade-long client relationship through to a sale 11:00 — Balancing owner priorities, culture, and staff at exit 12:30 — What "gratifying" actually means for Jennifer in a project 14:00 — Evolving as a consultant and staying a student of AI 15:30 — Niche marketing in a noisy world 17:00 — What business owners are worried about right now 18:30 — Financial breathing room as her first personal milestone 19:30 — The ten-year moment and "what if you're good enough" 21:00 — Being choosy with clients and the value of goal-oriented owners 22:00 — Two books, a speaking practice, and what's next 23:00 — Legacy as good information in the right hands 24:00 — Where to find Jennifer   Episode Resources   Discover how Jennifer helps entrepreneurs and established business owners build sustainable marketing foundations, sharpen their positioning, and play the long game with a consultant who's been in the trenches with them for two decades: www.fwdthink.ca Legacy Podcast: For more information about the Legacy Podcast and its co-hosts, visit https://businesslegacypodcast.com Leave a Review: If you enjoyed the episode, leave a review and rating on your preferred podcast platform. For more information: Visit https://businesslegacypodcast.com to access the show notes and additional resources on the episode.

In this episode, Paul Dio sits down with Jonathan Feldman, founder of NextCoreFlow, an automation and AI integration consultancy for small and medium-sized businesses. Jonathan is not a theorist. He's built and exited two businesses of his own — a college advertising magazine he ran across twenty markets and a planner business he grew past thirty million dollars a year on Amazon — before launching NextCoreFlow in the summer of 2025 to sit at the front edge of what he believes will be the most seismic decade of business change since the late nineties. Jonathan walks Paul through the "cold start" problem he sees over and over with founders — the ones who know AI matters, use it themselves, and still can't figure out where it belongs in their business. His answer is counterintuitive. The starting point isn't an AI tool. It's the operation itself. Where does work move? Where is it duplicated? Where are the workarounds nobody documented? Only after those workflows are visible does layering in automation and AI actually pay off. The conversation gets specific. Jonathan describes the acquisition scenario every founder-led services company should think about — the file cabinets, the extra ops headcount, the fragmented systems that quietly haircut the valuation on the way out the door. He walks through what a discovery call actually looks like, why the tokenized survey to every employee is the most valuable step in his process, and why the frontline view of the business is almost always different from the owner's. The episode closes on the humanity of the work. Jonathan is clear that he doesn't take engagements aimed at reducing headcount. He's after the two hours a day a producer spends creating invoices instead of writing new business, the menial layer that AI can strip out so the humans can go do what humans are best at. And he's built his engagement model around that idea — quick fixes, under ninety days, under fifteen thousand dollars, with ROI that has to justify itself.

In Episode, Paul Dio sits down with Dr. Nicole Aliotto, founder and CEO of Alla Breve Consulting, for a conversation about what good education actually looks like — and why the easiest metrics to measure are rarely the ones that matter most. With nearly three decades of experience spanning higher education, K-12, and the private sector at IBM, Nicole has spent her career helping schools turn data into direction. Nicole walks Paul through her journey from internal practitioner to founder, the early uncertainty of stepping off on her own in 2017 with no clients lined up, and the leap of faith that turned into a thriving consulting practice. She also shares how the pandemic forced her to diversify her clientele almost overnight, and how she's now rebuilt the K-12 work that first lit her up. The heart of the conversation is what she calls the "in-between" measures — trust, morale, belonging, staff voice, educator well-being — the indicators that schools often ignore in favor of the easier outputs. Nicole explains how she designs survey work that actually surfaces those nuances, why most school measurement efforts go awry, and what changes when an entire district finally starts talking about success in the same language. The episode closes on legacy. Nicole reflects on the clients who've taken her frameworks and used them to secure millions of dollars in grant funding, the second book she has releasing at the end of May 2026, and why, after thirty years, she still gets choked up when a team tells her they're finally all moving in the same direction.

Erica Goode spent her early career on the traditional accounting track — Big Four, Fortune 50 finance, the late nights and missed dinners that come standard with the path. Then she looked up at the senior leaders above her and realized she didn't want to be any of them when she grew up. That single honest moment set off a decade-long pivot that took her out of corporate, into full-time motherhood, and eventually into building the kind of accounting firm she'd never seen modeled for her. In this conversation with Paul Dio, Erica unpacks what it looks like to bring corporate-level skill — forecasting, cash-flow modeling, strategic finance — to the small businesses sitting right down the street. She talks about her first client, a Taekwondo studio, and how the work she'd built her career on suddenly became the thing standing between that small business and bankruptcy during the early months of COVID. The story is a quiet argument for why human accountants still matter, especially now. The episode also takes a hard look at the million-dollar revenue obsession that's everywhere in the consulting and accounting worlds. Erica makes the case that a business owner pulling $300K can take home almost as much as one chasing seven figures — minus the headcount, the overhead, and the burnout. Million-dollar revenue, in her words, is a vanity metric. What actually matters is what lands in your personal bank account at the end of the month, and how much of your life you got to keep along the way. There's also a fascinating detour into AI. Erica fed her own redacted tax return into Claude this past tax season just to see what would happen — and walked away with a 50/50 hit rate that captures exactly why human advisors still matter. The conversation lands on an optimistic note for the profession: when AI handles the rote work, accountants finally have room to be the human their clients actually need. Timestamps 00:00 – Introduction and welcome 01:00 – From Big Four to Fortune 50 to walking away 03:30 – "I don't see anybody I want to be when I grow up" 04:45 – Choosing to be home and not knowing there was a third path 06:00 – Missing accounting and the first client down the street 09:00 – The freedom of choosing your clients 11:00 – Books worth keeping on the shelf 13:00 – Why the Life First Accounting Firm podcast exists 17:00 – The vanity metric of seven-figure revenue 18:30 – Where AI can't replace the human 20:30 – Feeding her tax return into Claude 23:00 – Where accounting goes from here 25:30 – The Taekwondo studio and a cash-flow story that saved a business 30:00 – Where to find Erica Episode Resources Discover how Erica helps small business owners and entrepreneurs build profitable, life-first accounting practices through intentional forecasting, strategic finance, and client-by-client growth: www.ericagoodie.com Legacy Podcast: For more information about the Legacy Podcast and its co-hosts, visit https://businesslegacypodcast.com Leave a Review: If you enjoyed the episode, leave a review and rating on your preferred podcast platform. For more information: Visit https://businesslegacypodcast.com to access the show notes and additional resources on the episode.

Most business owners hear "AI" and immediately think: we need that. Myles Harrison thinks the opposite — and he built a company around it. Myles is the founder of  Praktikai, a boutique data and AI consulting firm whose name literally means practicality. A veteran of Big Five firms like Accenture and PwC, he now helps business owners cut through the noise and ask the real question: is technology actually your problem? In this episode, Myles shares why a bajillion-dollar tech investment can still fail if your people and processes aren't aligned, what it actually looks like to be a "sober, pragmatic" voice in an industry obsessed with hype, and how the best consultants don't make themselves the hero — they make their clients look good. We also dig into: The three-part operating model that most AI projects get wrong Why Myles is still waiting on the paperless office before worrying about the Terminator The farming metaphor that reframes how we think about automation and knowledge work What burnout on the Big Five consulting track actually taught him about limits The airport moment that surprised him most about working with clients in person If you've ever wondered whether AI is actually the solution — or just the most expensive way to avoid fixing the real problem — this episode is for you. Timestamps 00:30 Welcome and introductions 01:15 What is Praktikai — and why "practicality" is the whole point 02:45 From Big Five consulting to accidental entrepreneur 04:30 How to know if you need a consultant: "what part of your job sucks the most?" 06:15 The operating model problem: people, process, and technology 08:10 Why complexity is not the same as excellence 09:45 What makes consulting gratifying — and why the goal is to make clients look good 11:30 Myles' bearish take on AI: signal vs. noise and the paperless office problem 14:00 The farming metaphor: automation, knowledge work, and what actually disappears 16:20 The next five years: under-promise, over-deliver, and do good work 18:00 Finding your limits: burnout, sleep, and what fast-paced consulting actually costs 20:30 The airport moment — what surprised Myles most about working with clients in person 22:30 Where to find Myles and PRAKTIKAI   Learn more about PRAKTIKAI and how Myles helps businesses cut through AI hype and focus on what actually moves the needle: prktk.ai Legacy Podcast: For more information about the Legacy Podcast and its co-hosts, visit https://businesslegacypodcast.com Leave a Review: If you enjoyed the episode, leave a review and rating on your preferred podcast platform. For more information: Visit https://businesslegacypodcast.com to access the show notes and additional resources on the episode.

When Carol Kaemmerer's 20-year consulting career was abruptly ended by a corporate restructuring, she didn't see it as an ending — she saw it as a kaleidoscope being shaken. The pieces of her experience, expertise, and skills were still all there; they just needed to form a new pattern. In this episode, Carol shares how she rebuilt her career by helping other senior leaders do the same. Her work sits at the intersection of strategy and story: clarifying what executives want to be known for, positioning their leadership, and building visibility that reflects who they are today — not who they were three jobs ago. We dig into: Why "doing great work" isn't enough at the senior level Her "Seen, Trusted, Chosen" framework for executive visibility How a minimalist LinkedIn profile can quietly cost you the next opportunity The story of a burned-out sales director who became an administrative pastor at a megachurch — and what it teaches us about transferable skills Her concept of "Kaleidoscope Thinking" for career reinvention Why AI agents and search engines are now part of how decision-makers find leaders Whether you're a C-suite executive, a director eyeing the next rung, or someone navigating an unexpected career inflection point, Carol's perspective will change how you think about your professional narrative. Timestamps 03:00 — Welcome and introductions 03:42 — The inspiration behind starting the Kaemmerer Group (hint: termination) 05:30 — Discovering LinkedIn as a platform for personal positioning 07:02 — "I write business stories" — finding a coherent personal brand 09:09 — Why senior leaders lose opportunities they thought they had 11:08 — What decision-makers are really looking for (and where they look first) 12:20 — The "Seen, Trusted, Chosen" framework explained 14:37 — The hidden disadvantage of a minimalist C-suite profile 16:28 — Featured story: The burned-out sales director who became a pastor 20:27 — The intimate work of rebuilding people at career low points 21:01 — Kaleidoscope Thinking: career reinvention as pattern-shift 22:41 — Where to find Carol and her book Episode Resources Discover how Carol helps senior executives take control of their personal narrative, build visibility that matches their level, and position themselves for what's next: www.carolkaemmerer.com Legacy Podcast: For more information about the Legacy Podcast and its co-hosts, visit https://businesslegacypodcast.com Leave a Review: If you enjoyed the episode, leave a review and rating on your preferred podcast platform. For more information: Visit https://businesslegacypodcast.com to access the show notes and additional resources on the episode.