Small Business Stories

Why AI Won't Fix a Broken Business with Tullio Siragusa

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, cu

How to Get Startup Funding with Vijay Rajendran

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

Small Business Cybersecurity: What You Don't See Can Hurt You with Last Pass CEO Karim Toubba

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

The Founder Trap: Why Your Business Isn't Growing Even When You're Working Harder with Charles Gaudet

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

How to Plan Your Business Exit When Your Kids Don't Want to Take Over with John Abrams

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

What to Do When Your Business Is in Financial Trouble with Jim Martin

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 emp

Why Dating Apps Make It Harder to Find the Right Person with April Davis

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"

Why AI Is Making Your Marketing Easier But Not Better with Gee Ranasinha

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 acces

How to Stop Trying to Be Everything to Everyone with Christine Blosdale

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. Christi

Why Good Products Fail After Launch with Lon Riley

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 contradi

How to Build Confidence When You're Afraid to Put Yourself Out There with Patty Aubery

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

How Bad Credit Can Limit Your Business Funding Options with Daniel McDavid

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

How to Scale Your Business Without Growing Too Fast with Bryan Clayton

S6:E66 The Real Story About Scaling & Selling a Business with Bryan Clayton Bryan has actually done the thing entrepreneurs dream about: built a traditional business to

Why Entrepreneurs Struggle to Get Approved for a Mortgage with David Ostrowsky

S6:E65 Buying a home as an entrepreneur often feels like playing by a different set of rules. In this episode, Dr. LL speaks with mortgage specialist David Ostrowsky

with Matt Putra

S6:E64 Every entrepreneur has numbers. Not every entrepreneur knows how to listen to them. In this episode, Dr. LL sits down with fractional CFO Matt Putra to discu

How to Use AI Agents Without Replacing Your Team with Kenneth Corrêa

S6:E63 An optional title for this episode is, "Agentic AI, Human Judgment & Cognitive Organizations with Kenneth Corrêa." AI is moving faster than most organizations

Why Working Harder Isn't Fixing Your Business with Leadership Coach Michelle Pollack

S6:E62 Success becomes surprisingly heavy when you're carrying someone else's expectations. In this conversation, Dr. LL sits down with leadership coach Michelle Poll

How to Create Multiple Income Streams Without Burning Out with Kelvin Abrams

S6:E61 Building a business is difficult. Building several businesses at the same time requires a different way of thinking. In this conversation, Dr. LL sits down w

How to Build Wealth in Your Community Through Co-ops with Vernon Oakes

S6:E60 Not every successful business measures success the same way. In this conversation, Dr. LL sits down with Vernon Oakes, founder of Everything Cooperative, to ex

How to Know If Your Product Idea Will Sell with Juliette Fasset

S6:E59 Every invention begins with an idea. However, very few ideas become sustainable businesses. In this conversation, Dr. LL sits down with inventor and entreprene