Small Business Stories

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...