Problem Solvers

Today, Jason is sharing something different and special. His wife, Jennifer Miller, has a new podcast — a true-crime story about mistaken identity, impossible choices, and one man who goes to prison for his twin brother's crime. It's called Blood Will Tell. Here, you'll find the first episode. You can find the rest by subscribing to Blood Will Tell wherever you listen to Problem Solvers. Learn more about your ad choices. Visit megaphone.fm/adchoices

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

Brand historian Jason Liebig explains how nostalgia works as a strategic tool, not just a retro look. He breaks down why familiar emotions build trust faster and how brands use nostalgia without copying the past. Plus, practical ways founders can apply it through design, storytelling, and customer experience. Learn more about your ad choices. Visit megaphone.fm/adchoices

Listener Melissa calls the Help Line today because she's experiencing some analysis paralysis (haven't we all). Jason gives her a formula to help her determine which parts of her work she should change; plus, he shares how to failure-proof her pivot by making it into an experiment. Learn more about your ad choices. Visit megaphone.fm/adchoices

Yes, you can start a million-dollar business in a weekend. Noah Kagan, founder of AppSumo and author of the book "Million Dollar Weekend", shares how the foundations of a great business come together quickly, and why it's worth moving fast. Learn more about your ad choices. Visit megaphone.fm/adchoices

Building brand awareness doesn’t have to cost big bucks. It can be as simple as leveraging your relationships in the community. The founders of Cold Blooded and Bizarre share how they built a beloved local brand by showing up everywhere their community already gathers, and turning simple touchpoints into constant reminders. Plus a two headed snake! This episode is brought to you by CLA. With you on every step of your financial journey. To learn more, visit CLAConnect.com. Learn more about your ad choices. Visit megaphone.fm/adchoices

You’ve seen Robert Herjavec make deals on Shark Tank, but do you actually know how he thinks? In this candid conversation, Robert breaks down the real questions investors should ask, and the common mistakes founders keep making. He also warns about the wrong lesson some people take from Shark Tank. And yes, if he still thinks about passing on Scrub Daddy. Learn more about your ad choices. Visit megaphone.fm/adchoices

When Lew Frankfort joined Coach in 1979, he knew nothing about fashion but he understood people. That skill became the foundation of his leadership and the reason he transformed Coach from a small, overlooked accessories brand into a global powerhouse. In this episode, Lew shares the interview strategy he’s refined over decades and written up in his new book Bag Man. He breaks down the questions he asks, the tests he uses, and the surprising single trait he believes matters more than experience or résumé. Learn more about your ad choices. Visit megaphone.fm/adchoices

Feeling stuck? Uninspired? Unsure how to find the right answer to the problem you're trying to solve? Scott Anthony can get you unstuck. He teaches strategy at the Tuck School of Business at Dartmout, and is the author of the book Epic Disruptions. He walks us through simple, science-backed strategies to reboot your creativity, the psychology behind peak performance, and why the worst way to solve a problem is to force it. Learn more about your ad choices. Visit megaphone.fm/adchoices

What makes an idea truly worthy of your time? Nir Zicherman, co-founder of Anchor and former Head of Audiobooks at Spotify, thought he’d left the startup world behind. But he kept wondering if he could help people learn in a better way. And oboe.com was born. In this conversation, Nir and Jason explore how to know when you’ve found something that’s more than a project. It’s your next calling. Learn more about your ad choices. Visit megaphone.fm/adchoices

When Jared Foster of Times Ticking bought a small watch shop, he realized one question was killing sales. So he replaced it with a simple, repeatable strategy that made customers feel welcome and ready to buy. That shift helped Times Ticking land on Entrepreneur’s list of America’s Favorite Mom & Pop Shops and turn quick repairs into big sales. This episode is brought to you by CLA. With you on every step of your financial journey. To learn more, visit CLAConnect.com. Learn more about your ad choices. Visit megaphone.fm/adchoices