The Science of Knowing When to Walk Away

Melissa Bernstein co-founded Melissa & Doug and built it into a billion-dollar children's toy company. Along the way, she learned a lot about entrepreneurship, which she shares in her new book The Heart of Entrepreneurship. Today, for the first time publicly, she shares the three-part strategy she used to fight back and what happened the moment new ownership stopped following it. Learn more about your ad choices. Visit megaphone.fm/adchoices

Every entrepreneur has been told to push through, stay the course, and that grit is everything. But advice like that leaves out that some of the smartest, most successful people in business got there by quitting at exactly the right moment. So how do you know when that moment is? Dr. Anthony Klotz, organizational psychologist and author of Jolted, has spent years studying exactly this question. He joins the show to share his framework for figuring out whether you should stay and fight harder, or finally walk away Learn more about your ad choices. Visit megaphone.fm/adchoices

Kevin Smith went from making art to being the art and learned the hard way that when you become the product, there's no off switch. In this episode, Smith breaks down how he's stayed relevant for 30 years by treating fans like the bosses they actually are. Plus: Jason shares how he once convinced his college to spend their full year's speaker budget just to get Kevin Smith on campus and what happened when they talked afterward. Learn more about your ad choices. Visit megaphone.fm/adchoices

Joey Zwillinger, the founder of Allbirds and Biologica, sat down with Jason to talk about the challenges of finding your ideal customer. Joey's done it both ways. Starting with a product and searching for the right people to buy it, and starting with a problem and building the solution. In this conversation, he breaks down what actually works when you're hunting for product-market fit, and what to do when your customers surprise you (because they will). Learn more about your ad choices. Visit megaphone.fm/adchoices

Nobody likes meetings. But there’s a good reason for that. Organizational behavior expert Dr. Rebecca Hinds, author of the new book Your Best Meeting Ever, explains why most meetings are a massive waste of time and what to do about it. She shares a simple test to determine if a meeting actually deserves to be on your calendar. Plus, Jason also discovers something uncomfortable about his own approach to meetings. Learn more about your ad choices. Visit megaphone.fm/adchoices

For sole proprietors and self-employed professionals, taxes can feel confusing, time-consuming, and easy to get wrong. What counts as a deduction? How do you save money on your taxes? And how do you stay organized when you’re doing everything yourself? In this episode, CPA and tax expert with TurboTax, Lisa Greene-Lewis breaks down how solo business owners can make taxes simpler, smarter, and less stressful. We talk about common mistakes new business owners make, overlooked opportunities to save money, what they need to know for the upcoming season, and how the right tools and systems can help you stay focused on growing your business—not wrestling with paperwork. With the business tax filing deadlines are approaching quickly, with many returns due March 16, 2026, understanding what has changed and acting on it with the right guidance may be one of the most practical decisions a solopreneur makes this year. Learn more about filing your taxes with Intuit TurboTax, visit http://turbotax.com/business Learn more about your ad choices. Visit megaphone.fm/adchoices

Gary Vaynerchuk joins Jason to share why he believes traditional social media is fading and where smart businesses should focus next. He explains how to find the audience you’re overlooking, and offers a practical framework for getting your content in front of the right people in 2026. Plus, why one of his agencies is rebranding and what it signals about where marketing is headed. Learn more about your ad choices. Visit megaphone.fm/adchoices

Moments Lab co-founders and identical twins, Frederic & Philippe Petitpont, realized they were in the wrong role. The CEO became CTO. The CTO became CEO. As a result, the business got stronger. In this episode, they break down how to spot role misalignment and how putting the company first can unlock real scale. Learn more about your ad choices. Visit megaphone.fm/adchoices

We’re taught that good leaders decide fast. But that belief may be holding you back. Harvard instructor and author of Manage Yourself to Lead Others, Margaret Andrews, explains why effective decisions often take longer and how rushing creates more work later.Together, she and Jason explore the mystic around leadership and decisions. Plus, one easy way to know if your meetings are effective. Learn more about your ad choices. Visit megaphone.fm/adchoices

Jersey Mike’s just hit No. 1 on Entrepreneur’s Franchise 500,  as it enters a new era of ownership and leadership. New CEO Charlie Morrison explains how the brand plans to grow without breaking what already works. Plus, he reveals whether Danny DeVito is really going to lose his job to Eli Manning. Learn more about your ad choices. Visit megaphone.fm/adchoices