Problem Solvers

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

Sebastian Wernicke, a data scientist, speaker, and author of Data Inspired, explores why “data-driven” companies can become trapped by the past. They discuss boring hit songs, Google’s blue-link experiments, a surprising sports car stereo trend, and the risks of over-optimized newsletters. Wernicke also examines bold experimentation, trusting outliers, and building workplaces where junior analysts can challenge senior decision-makers.

Pat Flynn, founder of Smart Passive Income and creator of Deep Pocket Monster, discusses selling SPI to pursue Pokémon. Liz Wilcox, an email marketing expert and former Survivor contestant, shares how she acquired the business. They explore making personal brands transferable, preserving relationship-first culture, using email to spark growth, and scaling community without losing connection.

Tony Stucker, CEO who revived Pop-A-Shot with marketing and product smarts. He discusses nostalgia-driven rebranding and retro product redesign. He covers licensing deals with NBA and colleges, experiential trailers and competition activations. He outlines social sharing strategies and getting competitions on TV.

Caroline Webb, economist, leadership coach, and author of Leadership Intelligence and How to Have a Good Day. She explains why feedback often fails and how a simple shift in framing makes people actually hear you. Short, practical practices for noticing positives, investing in the overlooked middle, and signaling intent before developmental comments. Science-backed, time-smart approaches to everyday management challenges.

Aneesh Raman, LinkedIn’s Chief Economic Opportunity Officer and co-author of Open to Work, discusses how AI lowers startup costs and speeds prototyping. He explains why entrepreneurial thinking and distinctly human traits like curiosity, taste, and courage matter more than ever. Short, practical talks on using AI to amplify judgment, avoid AI sameness, and make work more creative and accessible.

Neal Schore, executive coach and former CEO who helps leaders reclaim time, explains how fear-driven habits quietly steal at least an hour a day. He breaks down why anxiety fuels endless Slack chains and diluted meetings. Hear practical fixes like a clarifying question, a five-minute swirl limit, and the devil/angel metaphor to stop catastrophic thinking and protect your calendar.