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.

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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

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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