Problem Solvers

Michael Bosstick, founder and CEO of Dear Media, breaks down the mechanics of audience growth and what smart creators do after they’ve built one. He shares his proven blueprint for turning attention into impact. This conversation will change how you think about the audience as an asset, not just a metric. Learn more about your ad choices. Visit megaphone.fm/adchoices

Most people think taking a month off work is impossible, but what if it’s actually a smart career move? Jillian Johnsrud, author of Retire Often, argues that planning a “mini-retirement” isn’t just good for your sanity. It forces you (and your company) to build better systems, and delegate more effectively. In this episode, Jason digs into her framework for making extended time off possible in any...

Jon Levy, behavioral scientist and author of Team Intelligence, is here to blow up what you thought you knew about leading teams. He reveals why most leadership advice is outdated, how the entire industry is built on a con man’s research from the 1900s, and what actually drives people to follow great leaders. He also shares one scientifically proven tip to build a smarter team. Learn more about yo...

Entrepreneurs face two kinds of problems: One has clear answers, the other does not. But is it possible to take unclear paths... and make them clearer? Alibaba.com president Kuo Zhang joins the show to talk about Accio, the company’s new AI tool that helps entrepreneurs create products, and the larger business lesson it represents. Learn more about your ad choices. Visit megaphone.fm/adchoices

Most businesses that resist change die. But Jake Shivery refused to give up analog photography and turned his Portland shop, Blue Moon Camera and Machine, into a thriving 26-person business.  But to keep his mission alive, Jake had to embrace changes he never wanted, from digitizing film to building a social media presence. In this episode, he shares how to balance stubborn focus with strategic fl...

Branding expert Laura Ries joins Jason to talk about her new book, The Strategic Enemy , and the power of positioning. Together, they break down how companies can define what they stand against, win customers, and become the go-to name in their category. This is a packed conversation about how to create campaigns that resonate and understand the strategy behind the marketing that shapes our world....

What do you do when your company is running out of money, your industry has collapsed, and even you think your idea is dumb? That’s the situation Siqi Chen, now founder and CEO of the finance platform Runway, faced in 2016 when he became CEO of Sandbox, a VR startup. Yet through a bold move, Chen managed to get the right people to believe, securing funding for a product that was a stupid good time...

Search is changing. Instead of typing a few words into Google, clients are now asking AI tools for hyper-specific recommendations. So how do you make sure they still find you? In this episode, Max DesMarais of Vital Design shares how to position your business so large language models present you as the solution to your client's problem. Learn more about your ad choices. Visit megaphone.fm/adchoice...

Marcus Lemonis built his reputation as the guy who could fix anything. It’s even in the name of his TV show The Fixer on FOX his new show following the success of The Profit on CNBC. But now, as he enters a new phase of leadership, he’s rethinking what it really means to lead. Lemonis has evolved. He’s leading from behind, pushing people harder than they’d push themselves, and even playing the vil...

 Michael Jacobson joined his uncle’s flower shop to help close it down.  Instead, he uncovered industry-wide problems like outdated tech, inefficient supply chains, and reliance on costly middlemen. By solving them one by one, he grew the French Florist into a thriving franchise that’s redefining the floral business. Learn more about your ad choices. Visit megaphone.fm/adchoices

The myth of the genius jerk founder has shaped startup culture for decades, but it’s wrong. Dr. Richard Hagberg and Tien Tzuo, co-authors of Founders Keepers, have the data to prove it. In this episode, they unpack the real traits that define high-performing founders, why bad behavior gets glorified, and how emotional intelligence and adaptability, not arrogance, drive lasting success. Learn more...

Julia Hartz is the co-founder and CEO of Eventbrite, the platform built to help anyone host and sell tickets to an event. But after years in the business, Julia and her team realized something surprising. Their biggest growth opportunity wasn’t with the people creating events, it was with the people searching for them. On this episode, Julia shares how Eventbrite rethought its product, reimagined...

 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...