Your Best Customers Are Costing You Too Much. Now What? Anthony Pompliano

Anthony Pompliano built an AI financial assistant people loved. Then his most engaged users started costing him too much money. That’s a good problem to have. But it’s still a problem. His solution came from an unlikely place. Olive Garden’s breadsticks. Here’s how Silvia cut costs without cutting what users love, and got 25% of monthly active users to pay. Find Anthony's book here! This episode of Problem Solvers is presented by AT&T Business. To learn more about how the right connectivity can help support your business as it grows, visit att.com/smallbusiness. Jason wants to help solve your impossible problem! Click the link below to sign up: https://entm.ag/levelup2026 Timestamps: 0:00 Intro 0:38 The idea of a “better problem” 2:05 Anthony’s book, How to Live an Extraordinary Life Volume Two 5:00 Silvia’s power-user problem 6:50 The Olive Garden breadstick lesson 9:15 Weighing every possible fix 11:07 Building a model router 12:55 Bracketing: a military trick for making decisions 16:50 Experiments vs. archaeology 18:15 Training their own model (97% cheaper) 19:10 Rolling out the paywall 20:40 Why people pay 21:45 How to spot this problem in your own business 24:16 Where to find Anthony and Silvia Learn more about your ad choices. Visit megaphone.fm/adchoices

GoFundMe had a strange problem. About a quarter of people created fundraisers and then never shared them. Better share buttons didn't fix it. That's because the problem wasn't the product. It was human. Asking for help is really, really hard. CEO Tim Cadogan explains how GoFundMe rebuilt around that truth, and why the fix generated more than double the help they expected. This episode of Problem Solvers is presented by AT&T Business. To learn more about how the right connectivity can help support your business as it grows, visit att.com/smallbusiness. Jason wants to help solve your impossible problem! Click the link below to sign up: https://entm.ag/levelup2026 Chapters: 00:00 – Intro 00:35 – GoFundMe's strange problem 02:10 – A quarter of fundraisers never get shared 03:10 – How GoFundMe spotted the gap 04:30 – Why better share buttons didn't work 05:15 – The four reasons people weren't sharing 07:00 – When the product isn't enough 08:30 – Fixing the sticking points, starting with titles 10:55 – Building the AI coach 12:45 – How the coach works day to day 14:00 – Is this just AI for AI's sake? 16:45 – A father's story 18:15 – Jason's book launch lesson: Asking is generous 19:50 – The paradox of help 20:15 – The best way to ask for help 21:30 – The results: More than double what they expected 22:15 – What's next for the coach Learn more about your ad choices. Visit megaphone.fm/adchoices

 SimpliSafe was built for renters. Renters didn't buy it. Homeowners did. Jason has told that story for years, because it's a perfect lesson in how founders get their customer wrong. But he never asked the obvious follow-up: once you finally find the right customer, then what? Now, 20 years in, SimpliSafe founder Chad Laurans and CEO Hilary Schneider reveal what comes after product-market fit, and why customers asking for "more cameras" didn't actually want more cameras. This episode of Problem Solvers is presented by AT&T Business. To learn more about how the right connectivity can help support your business as it grows, visit att.com/smallbusiness. Jason wants to help solve your impossible problem! Click the link below to sign up: https://entm.ag/levelup2026 0:00 The "faster horses" myth 0:29 Welcome to Problem Solvers 0:46 The SimpliSafe origin story: renters vs. homeowners 2:21 What happens after product-market fit? 2:55 Meet the guests 3:47 What product-market fit actually feels like 5:11 Should you build everything customers ask for? 6:11 Why you have to keep asking "why" 7:14 From "more cameras" to crime prevention 8:17 Fact check: Henry Ford never said it 9:22 What customers really want: peace of mind 10:02 Making a costly service profitable with AI 11:44 Launching a product that doesn't scale yet 13:48 Why big companies forget to prototype 16:51 Build things you're willing to throw away 18:26 What's next for SimpliSafe 19:48 The innovator's dilemma of a cheaper product 20:31 Mining customer support calls for insight 21:52 Go back to what made you great 23:22 The mission: every home secure 23:57 Long-term value comes from creating value 26:33 Wrap-up Learn more about your ad choices. Visit megaphone.fm/adchoices

Jon Taffer, host of the hit TV show "Bar Rescue", has sat on both sides of the franchising table. He's been a franchisee, including one franchise you'd never guess. Now, as founder of Taffer's Tavern, he runs his own franchise system. And even with 40-plus years in business, he's shopping for his next franchise right now. That perspective means he knows exactly what to ask before buying in. The question he says matters most is one most would-be franchisees never think to ask. Timestamps: 00:00 Jon Taffer's surprising next business move 00:30 Why franchising made Jason nervous 03:10 Jon's franchise résumé: from Hooters franchisee to Taffer's Tavern 04:22 Turnkey vs. brand: what you're really buying 07:02 Why so many corporate pros are jumping into franchising 08:08 The biggest perk: you can sit in it before you buy it 09:53 Beyond burgers: franchises in every industry 11:12 Jon's doggy daycare hunt and Jason's franchise near-miss 14:39 The FDD: the document you can't skim 16:58 The #1 red flag Jon won't touch with a 10-foot pole 20:49 The questions that reveal a franchisor's sales muscle 22:57 Jon's six-step vetting process 25:18 What the franchisor does vs. what's on you 28:13 Who Jon wants running a Taffer's Tavern 30:31 Cutting through the noise: Doritos Locos Tacos and the five-word mission 35:52 Local store marketing: own four or five blocks 39:05 What's new in franchising: smaller footprints, fewer days 40:37 The marketing opportunity hiding in every box 43:42 What World Cup fans revealed about franchise brands 44:49 How to take your first step Learn more about your ad choices. Visit megaphone.fm/adchoices

Raj Mehra had it all: a personal reason to build, a hot new technology, a sector ripe for disruption. Then he put his product in front of real users and watched them fail to use it. So he did the hard thing. He listened. What he learned wasn't just a fix. It was a completely different company. This is the story of Sage Healthcare, and it's also the story of what it takes to break up with your own idea. 0:00 – Intro: the "forbidden love" of founders and their original ideas 1:36 – Meet Raj Mehra, CEO & co-founder of Sage 2:33 – What Sage does today (senior care tech platform) 3:14 – The origin story: his grandmother's fall 3:57 – The original hypothesis — building a voice app (Alexa/Google Home era) 5:24 – Building the "expensive paperweight" before validating with users 7:56 – The co-founders join, and the decision to finally talk to users 8:56 – What they learned: hardware was outdated, but voice wasn't the answer 11:44 – Feeling relief, not defeat, when the original idea didn't hold up 12:46 – Finding the middle ground: off-the-shelf hardware + exceptional software 16:39 – Taking the product to market — first customer deployments 17:00 – Solving the hard technical and life-safety challenges 19:27 – Using design sprints to navigate every major crossroads 20:36 – Filtering ideas through the "North Star": does it improve care? 22:15 – Advice for early-stage founders navigating a new market 23:57 – Advice #2: knowing when the technology is actually ready 26:15 – Where to find Sage, and closing thoughts Learn more about your ad choices. Visit megaphone.fm/adchoices

Jason sits down with Sebastian Wernicke, data scientist and author of Data Inspired: Building an Organizational Culture of Inquiry for Lasting Transformation, to talk about why "data-driven" companies so often end up trapped inside what they already know instead of discovering what their customers actually need. They get into the sports car company that ignored its own sales numbers, the one question that reveals whether your company can actually handle being wrong, and how Jason's own newsletter taught him he'd built himself a very comfortable cage. Timestamps 0:00 The Hit Song Formula That Failed  0:27 Welcome to Problem Solvers  0:38 Why a Song About Pop Music Matters to Your Business  2:45 Meet Sebastian Wernicke, Author of Data Inspired  3:06 Why Data Feels Like Comfort (And Why That's a Trap)  4:52 Two Ways to Use Data: Optimization vs. Innovation  5:06 Google's "50 Shades of Blue" Experiment  6:38 Data-Driven vs. Data-Inspired, Defined  7:46 The Sports Car Company's Weird Stereo  10:25 How Do You Know Which Outlier to Trust?  13:19 Use Data to Support a Bold Guiding Policy, Not a Safe One  14:20 The Medical Device Company's Real Diagnosis  16:29 Jason's Own Data Trap: A/B Testing His Newsletter  20:59 Error Reduction vs. Loss Aversion  22:24 Can a Junior Analyst Challenge the Boss in Your Company?  26:03 The Book: Data Inspired Learn more about your ad choices. Visit megaphone.fm/adchoices

Before he was Deep Pocket Monster, Pat Flynn was the face behind Smart Passive Income. Eighteen years later, he's ready to pour everything into Pokémon, but he's not willing to abandon the community that built him. So he made a call most founders never make. Liz Wilcox, an email marketing expert with her own exit story, joins him to explain what happens next. Learn more about your ad choices. Visit megaphone.fm/adchoices

A few years ago, Jason rediscovered his love of Pop-A-Shot, the arcade basketball game. What he didn't know was the whole story behind Pop-A-Shot's sudden renaissance. Tony Stucker, the CEO of Pop-A-Shot, joined the show to unpack the brand strategy behind the turnaround and what it takes to extract new growth from a legacy asset. Learn more about your ad choices. Visit megaphone.fm/adchoices

Jason once got an edit back covered in red, all caps, like he'd been screamed at on paper. He swore he'd never do that to anyone, but it turns out most of us are still getting feedback wrong. Caroline Webb, author of Leadership Intelligence, breaks down the one shift that makes people actually hear you. It's simpler than you think, and it starts with what you say before the criticism.. Learn more about your ad choices. Visit megaphone.fm/adchoices

Will AI make entrepreneurship easier—or make entrepreneurs irrelevant?In this episode of Problem Solvers, Jason Feifer sits down with LinkedIn Chief Economic Opportunity Officer Aneesh Raman, co-author of Open to Work: How to Get Ahead in the Age of AI, to rethink the biggest fear around AI and business: that technology is coming for your job, your company, and your edge.Jason shares his “AI is a microwave” theory: it’s a powerful new tool, but we’re still learning what belongs in it—and what absolutely doesn’t. Aneesh explains why AI is lowering the cost of starting a business, making it easier to research markets, build prototypes, and test ideas fast. But as access goes up, so does the premium on something AI cannot replicate: your unique perspective, taste, curiosity, courage, communication, and lived experience.They break down why the future of work is not about humans becoming better AI prompters. It’s about becoming more entrepreneurial, more creative, and more distinctly human. In a world flooded with AI-generated sameness and “AI slop,” the people who win will be the ones who use AI to amplify—not replace—their judgment, originality, and connection. Learn more about your ad choices. Visit megaphone.fm/adchoices