Small Business Stories

S6:E91 What happens when your marketing reports say you're succeeding, but your business tells a different story? More advertising data doesn't necessarily mean better business decisions. Scott Desgrosseilliers , founder of Wicked Reports, has spent years helping businesses understand which marketing activities actually contribute to customer acquisition and growth. In this episode of Small Busine...

S6:E90 We have more information about health than ever before. So why are we still so confused about what to eat? Jenn Trepeck has spent seven years hosting Salad with a Side of Fries , helping listeners navigate nutrition claims, wellness trends, and conflicting advice. In this episode of Small Business Stories , she joins Dr. LL for a thoughtful conversation about the information we trust, the s...

S6:E89 "Passive income" may be one of the most misunderstood phrases in entrepreneurship. It can conjure images of money arriving without work, risk, systems, expertise, or responsibility. Melissa Nash sees it differently. The founder of Passively Rich with Rentals joins Dr. LL for a grounded conversation about long-term rental real estate, what "passive" actually requires, why she invests outside...

S6:E88 After nearly 450 conversations on his  Leaders With a Heart podcast, Payman Lorenzo has heard extraordinary stories of leadership, adversity, failure, resilience, and reinvention. But one of his most important lessons is surprisingly basic: Listen. Really listen. Queue up this episode of Small Business Stories for a deeply human conversation about leadership, boundaries, assumptions, patien...

S6:E87 Overall, small business sales are growing. So why do so many owners still feeling the squeeze? The answer is hiding underneath the headline. Matan Bar, CEO of Xero U.S ., joins Dr. LL to unpack what Xero's U.S. Small Business Insights data reveals when you look beyond one encouraging number: sales may be improving, but businesses are also contending with rising costs, longer waits for payme...

S6:E86 The businesses people overlook may be the ones worth examining. Especially those ew - yucky - services! Entrepreneurship culture gives enormous attention to innovation, technology, and businesses that sound impressive. Mark Regan built something very different: a recurring-revenue company around a simple problem many people do not want to solve themselves. In this episode of Small Business...

S6:E85 People experience your leadership long before you make a formal leadership decision. It's in how you enter a room. How you react when you're stressed. Whether you acknowledge someone. The story you tell. The difficult interaction you choose not to pass along to the next person. Lisa Even calls it the ripple effect: everything we say and do creates one, whether we're consciously choosing it...

S6:E84 It has never been easier to look like an expert. That may be precisely why genuine expertise matters more. AI can help produce polished content, sophisticated branding, books, social posts, and an increasingly convincing professional presence. But none of those things automatically demonstrate depth, judgment, experience, or the ability to create results. In this episode, Katrena Friel , fo...

S6:E83 How do you know when persistence is serving the business? Or at what point does attachment to what you've built prevent you from seeing it clearly? Joseph Shalaby knows something about operating through uncertainty. As founder of eMortgage Capital, he has built within an industry shaped by economic cycles, regulation, changing consumer expectations, and a persistent trust problem. But this...

S6:E82 Better Data, Better Decisions with Andy Janaitis What if your advertising dashboard says you're succeeding but your bank account says otherwise? That's not necessarily a marketing problem. It may be an interpretation problem. Queue up this episode of Small Business Stories with Andy Janaitis, founder of PPC Pitbulls , for a grounded look at what increasingly automated advertising requires f...

S6:E81 Businesses usually think about marketing from the inside out. Here's what we do. Here's why we're good. Here are our features. Here are our credentials. John Elbing thinks we should turn the entire thing around. As founder of Standpoint and creator of the Storybuilding approach, John helps businesses see themselves through the customer's eyes. His starting point is deceptively simple: befor...

S6:E80 AI, Empathy & Why Humans Still Matter with Nathan Strum AI can answer the phone. It can schedule appointments. It can listen to sales calls, extract insights and eliminate tedious administrative work. But can it make someone who has just lost their cat genuinely feel heard? Nathan Strum doesn't think so. For more than 20 years, his company Abbey Connect has built its reputation around human...

S6:E79 Why More Traffic Doesn't Mean More Business with John Sanders Your advertising may be doing exactly what you asked it to do. That doesn't mean it's helping your business. John Coleman Sanders has spent 16 years working with Google Ads, and he says the platform has undergone some of its most significant changes in just the past year. AI is interpreting intent, old strategies are becoming obs...

S6:E78 AI doesn't arrive inside a business as a neutral cure for everything that isn't working. It encounters the decision structures, silos, leadership behaviors, customer experience and culture that are already there and then it can make them move considerably faster. That's the tension at the center of this episode of Small Business Stories with Tullio Siragusa, founder of Inventrica Advisory....

S6:E77 A funding round can transform a company. It can also change who controls it, how it's expected to grow and even whether the founder remains CEO. So perhaps the first fundraising question shouldn't be How do I get the money? It should be: Do I actually want what comes with it? Queue up this episode of Small Business Stories with Vijay Rajendran , founder of Startup System and author of The F...

S6:E76 Security is ultimately a promise of trust. So what happens when that trust gets broken? Karim Toubba has had to answer that question in circumstances few CEOs would choose. He joined LastPass as their CEO only months before the company experienced a significant and highly publicized 2022 security breach. In this candid conversation, Karim acknowledges that LastPass initially communicated to...

S6:E75 What if getting more customers actually made your business worse? That's the paradox Charles Gaudet sees repeatedly. A founder builds a business through hard work, referrals and personal relationships. Success arrives. More customers come in. Employees are hired. Yet instead of gaining freedom, the founder becomes the hub through which nearly everything still has to pass. Queue up this epis...

S6:E74 What happens to your business when you aren't there anymore? For millions of founders, where more than half of all small businesses in the USA today are owned and operated by people over 50, that question is moving from theoretical to urgent. John Abrams says many owners assume they'll eventually pass the company to their children, sell it to an outside buyer or perhaps accept an offer from...

S6:E73 "If you were just here sooner." Jim Martin has never forgotten those words. They came from an employee of a 125-year-old company with approximately 1,800 employees that ultimately had to be liquidated. Jim had been brought in during the crisis. But by then, many of the options that might once have existed were gone. Queue up this episode of Small Business Stories for a candid conversation a...

S6:E72 Dating apps give us more choices than we've ever had, so why does finding the right person feel harder? Some people have given up, saying that it is "impossible" to find a mate! Matchmaker April Davis says too many options may actually be part of the problem , encouraging people to filter potential partners by features instead of recognizing the values that sustain a relationship. Indeed, t...

S6:E71 AI has raised the floor. But has it raised the ceiling? Gee Ranasinha doesn't think so. AI has democratized content production, giving small businesses access to capabilities once reserved for larger organizations. But Gee argues that we're simultaneously creating what he calls a greater "preponderance of mediocrity" meaning more acceptable content, more quickly, from more companies, increa...

S6:E70 Stop Trying to Be Everything to Everyone with Christine Blosdale You can be extraordinarily talented and still make yourself almost impossible to hire. Christine Blosdale sees it constantly: entrepreneurs with multiple skills, multiple offers, multiple audiences and multiple platforms trying desperately not to leave any opportunity on the table. The result? People don't know what to hire th...

S6:E69 When a Better Product Isn't Enough with Lon Riley This is stronger for streaming than a generic "Lessons from a Product Launch." It captures the central contradiction of his experience and makes Lon's hard-earned lesson the authority proposition. "Everybody loves your idea until it's time to separate them from their cash." That line from Lon Riley could probably hang above the desk of every...

S6:E68 Sometimes you meet someone whose work you've known for years and then discover that the story behind the success is even better than you expected. This was one of those conversations. Dr. LL openly admits to a little fangirling (okay - a lot - I cannot even tell you what an honor and privilege it was to have her on my show!) as she welcomes Patty Aubery, longtime business partner of Jack Ca...

S6:E67 The worst time to discover you have a credit problem may be when your business desperately needs money. An unexpected expense hits. Cash flow tightens. Payroll is coming. Suddenly, the entrepreneur isn't shopping for the best financing; he or she is searching for  any financing. Queue up this episode of Small Business Stories as Dr. LL talks with Daniel McDavid, founder of Move Mountains Cr...