Problem Solvers

 Ania Smith, CEO of TaskRabbit, has spent her career building marketplace businesses. She shares the operational challenges of matching people who need tasks done with people who can do them and how TaskRabbit solves for the millions of unpredictable human variables that come with it. Balancing supply and demand at scale means identifying the patterns and solving the problems. Learn more about you...

Eynat Guez, co-founder and CEO of Papaya Global, shares how a single contract clause nearly bankrupted her first company and why confronting that worst-case scenario changed everything. Instead of panicking, she mapped out the fallout, turned it into leverage, and negotiated a way out. That mindset became a repeatable leadership strategy, helping her build a $3 billion global payroll platform whil...

How does an old video game get reborn as a modern entertainment behemoth? Just ask the producers behind Sonic the Hedgehog, Tomb Raider, and more. Their names are Dmitri M. Johnson and Mike Goldberg, co-founders of Story Kitchen, a media company that specializes in adapting classic video games and other unconventional IP for TV and film. Upcoming projects include adaptations for Toys R' Us, Teddy...

Remember the Sonic “Two Guys” commercials? That simple marketing campaign transformed the brand — but creating it wasn’t simple at all. In this episode, Cliff Hudson (former Sonic CEO) and Craig Miller (former Sonic CIO) share how the “Two Guys” campaign emerged through testing, refinement, and real-time feedback. This  low-budget idea turned into a powerful brand asset. Hungry for more? Check out...

Do you want to learn to predict what your competitors will do next and prepare for it? Arjan Singh, author of Competitive Success: Building Winning Strategies with Corporate War Games, joins the show to explain how companies of any size can use war game simulations to uncover blind spots, anticipate moves, and build stronger contingency plans. Singh has worked with 68 of the top 100 companies on t...

In a space evolving as fast as AI, how do you build something that stays relevant? According to Misbah and Farah Uraizee, co-founders of Nectar Social, the answer starts with founder-market fit. Solve the problem that you are uniquely suited to solve. In this episode, they share how that clarity helped them land early clients, raise a full seed round without even using a pitch deck, and introduce...

In a high-tech world, old-school relationships still win. So take a cue from Hollywood: Film producer and financier Matthew Helderman, cofounder and CEO of BondIt Media Capital and Buffalo8, shares how his team turned the classic business lunch into a repeatable growth strategy - one so effective, it’s written into the employee handbook. These social outings have even led to seven-figure deals. In...

Everyone says to “build your personal brand,” but how do you actually do that on LinkedIn? In this episode, Jason talks with Laura Lorenzetti, Senior Director and Executive Editor at LinkedIn News, about what really works and what doesn’t. They walk through how to create content that sparks conversation and build a strategy for growing your personal brand. Along the way, they bust some common Link...

What holds us back from doing new things? The answer is often learning — there's too much information to absorb, and we get stuck trying to consume it all. Pat Flynn has a different model. He's the creator of Smart Passive Income and the YouTube channel Deep Pocket Monster, and has developed a framework he calls Lean Learning. (It's also the name of his new book.) It's a way to learn information f...

Need cash to grow? Small businesses often have trouble accessing traditional financing, which is why global marketplace eBay is stepping in to help. On this episode, eBay's VP and GM of Financial Services and Payments, Avritti Khandurie Mittal, explains the financing challenges that many small businesses face, how eBay Seller Capital is making financing accessible to them on transparent terms, and...

Lauryn Bosstick turned The Skinny Confidential into more than just a brand. She built a deeply invested community. That connection has fueled product launches, new ventures like Dear Media, and cultivated long-term brand loyalty. In this episode, she breaks down how she tells a brand story, gets her audience excited to buy in, and sets healthy boundaries without losing trust. If you're trying to g...

Ever feel unmotivated? Or, ever notice that your team is slumping? You (or they) may be missing a something very specific. According to a revolutionary psychological theory, all humans have the same three basic psychological needs — and if you don't find them in your work, your motivation will drag. In this episode, Jason breaks this theory down, and shows you how to apply it in leadership, parent...

Jason bought a really old rock—and it sparked a fascination with the Neolithic era. In this episode, he’s joined by Dr. John Shea, archaeologist and stone tool expert, for a conversation about the original problem-solvers. They explore how communication became humanity’s superpower, why the stone ax was the first handheld all-purpose tool (and how it’s surprisingly similar to a smartphone), and th...

Every business needs to find product-market fit — and AI can help. How? In this episode, Harvard Business School professor and entrepreneur Jeff Bussgang (author of The Experimental Machine: Finding Product-Market Fit in the Age of AI) walks us through the process. It’s a free consulting session with everything included: step-by-step directions, real examples, and the names of the LLMs you need to...

This is episode 400 of Problem Solvers, and I've learned a few important things about how to evolve a product! In this episode, I share why you might be WRONG about what makes your product special — and how to keep refining with your audience in mind. Learn more about your ad choices. Visit megaphone.fm/adchoices

It's a simple philosophy. But what does it take to actually achieve? We talk to Jesse Cole, owner of the baseball team Savannah Bananas, about the idea that transformed his business—and how it can work in any industry. Learn more about your ad choices. Visit megaphone.fm/adchoices

Here's a strategy for talking people down, and even turning people's anger to your advantage. And I have the emails to prove it! Learn more about your ad choices. Visit megaphone.fm/adchoices

Donald Miller literally wrote the book on brand storytelling: It's called Building A StoryBrand, and it sold 1 million copies. He's just released an updated version. On this podcast, Don explains how to communicate your brand's value in a simple story. After that, I invite a few entrepreneurs to tell him about their brands — and he comes up with stories for them! It'll change the way you think abo...

Want to pitch yourself with confidence? Want to become better at sales, or just selling yourself? You must learn to be shameless. That's the advice from Jenny Wood, former Google executive and author of the new book Wild Courage: Go After What You Want and Get It. In this episode, she teaches you how and why to embrace shamelessness. Learn more about your ad choices. Visit megaphone.fm/adchoices

Angie Hicks has been the face of Angie’s List (now called Angi) for decades. It’s not a role she wanted, but she knows how important it is — and how to play it perfectly. Learn more about your ad choices. Visit megaphone.fm/adchoices

Want to get your product onto store shelves? Listen to this. Matt Adelmann used to be a buyer at Target, where he was responsible for placing products on shelves. Here are the three mistakes that founders always get wrong about retail — and how you can set yourself up for success. Learn more about your ad choices. Visit megaphone.fm/adchoices

In 2006, a debate raged inside of Nintendo: Do they bundle their new Wii console with the game Wii Sports, or sell the game separately? Reggie Fils- Aimé was president of North America at the time, and he argued yes — because even though it meant giving up revenue upfront, it would lead to more Wii sales later. Here, he explains the battle and how he won it. Learn more about your ad choices. Visit...

Entrepreneurs love telling stories of perseverance. But that can be misleading. "In order to succeed, you're going to have to quit the things that aren't worth pursuing," says Annie Duke, author of the book "Quit: The Power of Knowing When to Walk Away". On this episode, she explains why we should see quitting as a virtue — and how to know when it's time to walk away. Learn more about your ad choi...

One night, Holden Forrest drew a wild idea on the back of his daughter's math homework: What if he could lower a house into the ground, as a way to escape oncoming wildfires? He couldn't shake this idea, so he started researching whether it's possible — and now, years later, he has a company called HiberTec, multiple patents, groundbreaking technology, and is raising money to build his first proto...

There are three types of skills, Jen Kem says: The ability to visualize, strategize, or mobilize. Everyone has these skills in different combinations — and when you can assemble a team with the right mix of combinations, you've built something unstoppable. On this episode, Kem (author of the new book "Unicorn Team") explains how it works, how to identify which combination of types you are, and how...