Pat Flynn asks "How Do You Sell A Personal Brand"

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users 7:56 – The co-founders join, and the decision to finally talk to users 8:56 – What they learned: hardware was outdated, but voice wasn't the answer 11:44 – Feeling relief, not defeat, when the original idea didn't hold up 12:46 – Finding the middle ground: off-the-shelf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

Executive Coach Neal Schore says that fear-driven habits are quietly stealing at least an hour from your day, every day. Drawing from decades of coaching founders, operators, and unicorn CEOs, Neal explains how anxiety about being fired, judged by boards, or seen as “not enough” leads to endless Slack chains, diluted meetings, and mental “swirls” that crush focus and time. Neal and Entrepreneur Editor in Chief Jason Feifer unpack why good things often start with worst-case scenarios (like getting fired), how to stop overcompensating out of fear, and why managing you—not everyone else—is the only way to reclaim your calendar. He shares practical tools from his new book, The 25th Hour, like the “clarifying question” that can turn a 7-hour crisis into a 7-minute conversation, the devil/angel metaphor for fear versus real performance issues, and a simple five-minute “swirl limit” to stop catastrophic thinking from hijacking your nights and weekends. If you’re a founder or senior leader stuck in loss-aversion, overcommitting to boards, or living in constant “what if I get fired?” mode, this conversation shows you how to get out of your own way, protect your time, and even see job loss or client churn as the start of better fits—not the end of your career. Learn more about your ad choices. Visit megaphone.fm/adchoices

Tom Szaky built TerraCycle into a recycling giant, then decided recycling wasn't good enough. His new venture, Loop, aimed to replace disposable packaging with reusable containers for brands like Tide and Häagen-Dazs. Consumers loved it. Retailers loved it. So why did it nearly die in four out of five test markets? Szaky breaks down the hidden flaw that almost killed Loop, and the simple insight that finally made it scale. Learn more about your ad choices. Visit megaphone.fm/adchoices

Here's a number that should stop you: 11,000 pairs of jeans, sold in 36 hours, from one video posted by a customer with just 5,000 followers. That's the end result of years of work by Brieane Olson, CEO of Pacsun, who decided her brand needed to stop talking at its customers and start building with them. In this episode, Olson shares strategies from her new book, Co-Created, and what she thinks most companies get wrong about "community" in the first place. Learn more about your ad choices. Visit megaphone.fm/adchoices

Leadership expert Ryan Hawk tackles one of the biggest traps for ambitious entrepreneurs: dabbling in everything and committing to nothing. Ryan unpacks the idea of “beefing up your obituary” by becoming the kind of person people remember for deep work and sustained excellence—not half-finished projects.If you’ve been spreading yourself thin across side hustles, content platforms, and random opportunities, this conversation will help you identify your “one main thing,” build an ecosystem around it, and know when you’re still just coasting versus when it’s time to dive. Check out Ryan's new book, The Price of Becoming. Learn more about your ad choices. Visit megaphone.fm/adchoices