Problem Solvers

Flowers for Dreams gives away 25% of its profits. In the flower business, where margins are already brutal. Co-founder Steve Dyme sketched that number on a bar napkin 15 years ago, and he’s kept it through investor pushback and on-air skepticism from Megyn Kelly. The result is more than $1.8 million donated, and a spot on Entrepreneur’s America’s Favorite Mom and Pop Shops list. But there’s a twis...

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 o...

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 S...

 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...

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 qu...

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...

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 quest...

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. Visi...

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...

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...

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 Ed...

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 t...

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 mo...

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...

Naveen Jain has built multiple billion-dollar companies all without being the smartest person in the room. His secret? He asks the questions the experts are too expert to ask. In this episode, Naveen joins Jason to make the case that your biggest weakness might actually be your biggest asset - if you're curious enough to use it. Naveen breaks down the framework behind his new book, Counterintuitiv...

Jason and Emily McCarthy built GoRuck into the leading name in rucking. But when rising costs forced them to raise prices, that community became more than a marketing asset. It became the reason the moment didn't turn into a crisis. Jason and Emily explain why with a loyal community being upfront with bad news is always the smarter play. Learn more about your ad choices. Visit megaphone.fm/adchoic...

You know what you do, but does anyone else? There's often a gap between what you offer and how you explain it. In this episode, Jason shares his framework for closing that gap, so your audience knows exactly what you're offering, and why you're the right choice. Learn more about your ad choices. Visit megaphone.fm/adchoices

A viral ad from Columbia Sportswear caught Jason's eye. After he wrote about it on LinkedIn, the company reached out. So Jason sat down with Tim Boyle, CEO and third-generation owner of Columbia Sportswear, to find out where the idea came from and what it reveals about how to reposition a legacy brand. The outdoor apparel industry had gotten serious and self-important. Columbia decided it was time...

Having one of the most recognizable and beloved celebrities in the world attached to your brand seems like it should be an easy win. But getting someone to buy once is one thing. Getting them to buy again is the real test. Cordell Broadus (Snoop Dogg's son) and his business partner Sam Rockwell explain what it actually takes to build an ice cream brand like Dr. Bombay, one that delivers value beyo...

The kids' juice aisle looks completely covered. So does the protein market. Most people would conclude there's no room for anything new. Ciara didn't. The Grammy-winning musician and mom of four was watching her daughter refuse every protein option put in front of her. So Ciara started looking for solutions and met Chris Koch, a CPG entrepreneur. Together, they founded Frosh, the first protein-enh...

Sami Inkinen is a three-time founder and world-class triathlete. A triathlete! And yet he went to the doctor and discovered he was pre-diabetic. The news triggered a series of changes including a pivot away from his real estate startup Trulia toward his healthcare company Virta Health, where he's now on a mission to reverse metabolic disease in one billion people. And along the way, he developed s...

David Rusenko built Weebly from a dorm room start-up with friends to a business with 300 employees and over $200 million in revenue. But somewhere around employee 25, he hit a wall and realized the problem wasn't his team. It was him. A chance dinner with Richard Branson changed everything. Learn more about your ad choices. Visit megaphone.fm/adchoices

The President of Burger King, Tom Curtis, knew the brand had gotten stale and that customers had drifted away. So he did something almost no executive does. He gave out a phone number and told people to call him directly. Over 41,000 calls came in.  What followed was a viral moment but more importantly, it became a real-time feedback engine. Tom sits down with Jason to talk about why he opened the...

Unsure what to charge for your services? You're not alone. Ilana Golan struggled with that too, until she developed a framework she now teaches to others through her Leap Academy. On this episode, Ilana helps you set your rates and get what you deserve. Learn more about your ad choices. Visit megaphone.fm/adchoices