He’s a Grammy-winning musician, an Academy Award-winning filmmaker, a DJ, a teacher, author of multiple books, a podcaster, host of the web series “Quest for Craft” and oh yeah, the co-frontman for a little band you may have seen on “The Tonight Show” called The Roots.

In this conversation, the very busy Questlove talks about being crazy productive without going crazy, re-capturing your creative juices and the surprising song that is guaranteed to get a party going.

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Joe De Sena (CEO of Spartan Race), Ben Askren (Co-Founder of AWA) and clinical psychologist David Sacks discuss their new book, “Extreme Balance: Paradoxical Principles That Make You a Champion.” In the world of elite sports, the authors say that victory is often attributed to physical and athletic prowess, but argue that the real key to unlocking our full potential lies in our mindset. During this conversation, the performance and motivation experts dive into all kinds of unexplored territories of the mind, challenging you to reconsider your entire approach to success. Get ready to get pumped up to take on the world!

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David Cross is a self-described "professional talker," but let's go ahead and expand on that bio just a bit. Cross is one of the funniest human beings on this planet we call Earth, touting a resume that is absolutely littered with iconic comedy creations — Mr. Show, Arrested Development and his latest special, Worst Daddy in the World, to name a few. He's very funny — and very busy. He currently hosts the podcast Senses Working Overtime with David Cross and put together a show, David Cross and His Super Pals, which will feature the likes of Bob Odenkirk, Sarah Silverman and Fred Armisen New York City's SummerStage in Central Park on August 8. Also on August 8, he'll star in the fourth and final season of The Umbrella Academy, and after that? He's hitting the road with his new comedy tour, David Cross: The End of the Beginning of the End.

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Four-time Pro Bowl wide receiver Stefon Diggs is not only one of the most talented players in the NFL, he's also one of the most stylish. The Houston Texans star launched his own fashion line LIEMhomme, which has been celebrated in the pages of Vogue and other high-fashion magazines, and sat down to discuss its launch, his vision and the brand's future.

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Jacob Hadjigeorgis, owner of Jacob's Pickles in the Upper West Side, shares his journey from growing up in a family of restaurateurs to becoming a successful entrepreneur. Guided by his father, his mentor, Jacob honed the qualities that set him apart: a deep passion for hospitality, a strong work ethic, and a creative vision. In this episode, he discusses how these traits, along with his innovative use of pickles to elevate comfort food, helped turn Jacob's Pickles into a beloved culinary destination and a staple in the Upper West Side community

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Vishal Dhawan, Chief Product and Technology Officer at Curb Mobility, a ride hailing marketplace that connects you to professional drivers in cities nation wide. In this episode Vishal shares his journey of building, leading, and inspiring teams to launch scalable products that delight users. With a knack for solving complex problems and opening new markets, Vishal has grown products from early stages to over $200 million in revenue. He excels in translating vision into execution, balancing design with algorithmic impact, and fostering a culture of leadership and action. Join us as Vishal discusses his strategic approach to innovation, product growth, and team building in the competitive ride-hailing marketplace.

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Kevin Hart, the multi-talented comedian, actor, and entrepreneur, joins us in this episode to discuss his latest venture: Gran Coramino Tequila. Known for his relentless work ethic and unparalleled success in the entertainment industry, Kevin brings the same level of dedication and passion to his tequila brand. Realizing that his culture and community had not been properly introduced to Cristalino, a unique type of tequila, and its accessible price point, Kevin saw a perfect opportunity for a business venture. Join us as Kevin shares the story behind Gran Coramino, emphasizing the importance of hard work and the unique qualities that set his tequila apart

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Jill W. Fox is the Founder of Fox Social Media. Jill initially learned social media to keep an eye on her then-teenagers. In 2010, Jill founded the company after working with her children’s sports teams to run their social media pages and falling in love with the process. Now, Jill runs a six-figure company planning and managing social media for her clients. Her advice? Make sure you love what you do.

Listen to the Side Hustle to Small Business podcast on Apple Podcasts or Spotify, or visit: entm.ag/hiscox

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Stephen Lease, CEO and Co-Founder of Goodr, shares his journey from early challenges to leading a thriving company known for its stylish and affordable sunglasses. Passionate about running, Stephen saw a problem that needed fixing: affordable, quality glasses for runners. Embracing failure as a stepping stone, he turned setbacks into opportunities, driving Goodr to success. Join us as Stephen discusses the importance of resilience, innovation, and learning from failures in building a successful brand and business.

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