The Matt Show

Chris Classick built Classick Studios in Chicago the year after he lost his mother. He had gear, a bedroom, and nothing left to fear. Two decades later, his studio has hosted Chance the Rapper, Khelani, SZA, Tyler the Creator, Lil Wayne, Chief Keef, and dozens more.  In this episode, Chris breaks down what it means to be a creative architect, why artists only have one job (just be themselves), how...

alen Cancel and Andrew "DagZ" are two of Chicago's most plugged-in creatives. DJs, event curators, community builders. They've been shaping how the city's nightlife and music scene feels for years. This conversation went everywhere. We got into Filipino culture in Chicago, what makes someone “believable” vs. “fake”, whether chivalry is dead in 2026, what happens when friend g...

Forever Band is a Chicago recording artist and content creator who went from 7K to 340K followers in about a month after his videos reversing microaggressions on strangers racked up hundreds of millions of views. He joins Matt to talk about how it all happened, his views on race in America, why he quit drugs and alcohol, his take on love and marriage, and his come up in Chicago's music scene....

Sydny August is a Chicago-born singer who went from recording music in her college dorm room to getting signed by Lil Durk to OTF (Only The Family) - and it all started with a birthday Instagram post. In this episode of The Matt Show, Sydny shares the crazy random story of how Lil Durk discovered her music, DM'd her out of nowhere, and eventually brought her into the OTF family. We dive deep i...

From E-commerce success to the cutting edge of AI, I’m joined by serial entrepreneur Gera Baano to talk about the highs and lows of building in tech at a young age. Gera Baano has lived several business lifetimes before the age of 25. From selling a dating app to managing 6-figure e-commerce brands, Gera now focuses on Polymath AI and Ghostbuilt, where he is redefining how products are made using...

I sit down with Juliana Miller — an artist manager, A&R at Classicks Never Die, DJ, and member of The Recording Academy — to talk about what it really takes to guide artists through the highs and lows of music. From discovering talent to helping creatives find their rhythm, Juliana shares lessons on building trust, protecting your energy, and staying grounded in purpose while moving through th...

Landon Campbell is an investor the general manager at Drive Capital, Chicago. He's also the author of LandonsLoop where he writes about innovation in Chicago tech. Landon relentlessly puts-on for the city of Chicago to be a center of hyper-growth in tech and AI innovation. We talk about his background in venture capital and what he sees for the growth of Chicago as a tech ecosystem. Follow us...

{Listen to the full experience on my Substack Matt's Recap} Custom resume for VaynerX & Mike Boyd Jr https://open.substack.com/pub/mattsrecap/p/matts-entrepreneurial-journey-8-years?r=2dcz9j&utm_campaign=post&utm_medium=web&showWelcome=true

Eddie is a seasoned professional in the music industry. As an attorney, he founded 'Protect and Collect,' specializing in intellectual property. He's taught at SAE, is an adjunct professor at Columbia College Chicago, and has spoken at major events like South by Southwest. Sometimes Eddie is a DJ! Eddie is deeply ingrained in Chicago's music and cultural ecosystem. Follow Eddie on...

Emma Mckee is a legendary cross stitcher. In 2014, Emma stitched her first piece: An adaptation of Will Prince’s artwork for Chance the Rapper’s song “Hey Ma.” She followed that with a piece for street artist JC Rivera, Chicago’s “Bear Champ.” Her portfolio expanded from there, as she firmly planted herself within Chicago’s rap community, as the scene’s preeminent — and only — hip-hop cross stitch...

Sam Thousand is a musician, event curator, and director. Sam speaks on his career in the performing music space, his vision to create ChiBrations to bring more discoverability to the rising arts scene in Chicago, and how he believes art has the potential to unify us in incredible ways. #mattsmith #theintersection #theintersectionpod #theintersectionpodcast #samthousand Follow Sam on Instagram: htt...

In my interview with Zehra, we discuss how her understanding of art history informs her work in Venture Capital. We talk about the events she curates in New York, from breakfasts and panel discussions to pottery classes and workout sessions. Zehra emphasizes the value of genuine engagement, diversity, and community-building, highlighting the need for meaningful connections and respecting participa...

Chris Vergara is an up and coming Director & Creative strategist. Chris has directed videos for Chance The Rapper, G-Eazy, SuperStarKami, Dry Boy, and more… Not only music videos, but Chris has made corporate videos, travel videos, short documentaries, Chris has done it all. Chris and Matt have a unique shared history, meeting each other as budding entrepreneurs in the creatives scene and grow...

Matt interviews Jaeson, the founder of 88rising and OP3N. Jaeson shares his incredible story of growing up in the Bay Area in the 80s and 90s and how he was exposed to hip hop culture, kicked out of three high schools, became a youth pastor, paying Bruno Mars only $1,500 to record four Christian rap tracks with him before the fame, and even being mentored by MC Hammer who brought him around the ea...

Jamie Cho is a marketing lead at Wildr, working to make social media a more positive space. Her background is focused on consumer social & our conversation was focused around empowering creatives in the creator economy. Follow Jamie: LinkedIn: https://www.linkedin.com/in/yoonseojamiecho/ Twitter / X: https://twitter.com/itsjamiecho #theintersectionpodcast #nostopmatt #theintersection

Ruben Harris is the CEO of Career Karam, the number one destination for career guidance & the largest platform to help workers find job training programs and get jobs in tech. Rubin has helped tens of thousands of people get into tech and inspire people to see that you can get into tech regardless of how much experience you have, where you come from, what school you went to, or what struggles...

Georgia Dienst's background includes Google, Google's Innovation Lab Google X, Kernel innovating in the field of neuroscience and neuromedicine. Today she's a CEO coach to VC backed founders. See her website: https://www.georgiadienst.com/ #theintersection #theintersectionpodcast #mattsmith

Matt and Isiah ThoughtPoet Veney get deep into room for improvement in Chicago's creative scene and the city as a whole. ThoughtPoet is a writer, photographer, community organizer. ThoughtPoet has been featured in The Field Museum, The Chicago Tribune, Essence Mag, Southside weekly, and The Chicago Reader. He’s done work with G herbo, Taylor Bennett, Vic Mensa, Chance the Rapper, and even grew...

TroyFromChicago is a Emmy Award winning cinematic director and and photographer. His work has been featured in Billboard, TIME Magazine, the Art Institute of Chicago, Art Basel: Switzerland, and more. Troy has directed or been a part of the production of videos for Vic Mensa, Chance The Rapper, Joey Purp, Super Start Kami, Joey Badass, Lucki, Matt Ox, and more.. ____________ Follow Troy: Instagram...

Enitan is a 3x best selling author on dating and relationships in the modern world. Enitan is the co-founder and creative director of FLOURYSH, the largest platform to shop and discover Black-owned businesses. He’s produced short films, been a keynote speaker at Stanford & Harvard, partnered on projects with Usher, even majored in computer science and interned at HP in Silicon Valley! Follow E...

Sonia Nagar is a general partner venture capitalist at the Pritzker Group. With a background in mechanical engineering, self-taught programming skills, an MBA from Harvard, and experience launching an e-commerce startup herself, Sonia has an impressive track record in the business-building world. ______ Follow Sonia:  Sonia’s LinkedIn: https://www.linkedin.com/in/sonias3/ ______ Follow Matt: Insta...

Gale Wilkinson is the founding partner at VITALIZE VC where she invests in early stage startups. Gale is well known as a venture capitalist in Chicago and on Twitter. democratizing access to angel investing through Vitalize Angels, the world’s first angel group for both accredited and non-accredited investors. ______ Follow Gale: Gale’s Twitter: https://twitter.com/galeforcevc?s=21&... Gale’s...

Wally Green is a professional ping pong legend. As US ambassador for ping pong, Wally has played in North Korea for world peace and diplomacy and represented the US all around the world in Germany, Japan, South Korea, China, Croatia,  and more. He’s been featured in the New York Times and Olympics.com . He’s been on the Steve Harvey show. He was featured in an award winning documentary called “The...

Ian Brock is the founder of Dream Hustle Code, making tech and being in the tech industry cool for kids that would have otherwise seen the space as lame or felt alienated by it. At only 18 years old Ian is an accomplished entrepreneur who has rubbed shoulders with the likes of Oprah, Steve Harvey, Ben Horowitz, G Herbo, Robert F. Smith, Eric Thomas and many more. Follow Ian Dream Hustle Code Websi...

Scott Kitun is the founder of Tech Nori, one of the truly OG startup content and community brands that contributed a lot to the startup ecosystem in Chicago over the years. Scott is the founder of Song Finch, a company that makes it easier for independent music artists to make money without having to be super famous, letting you make money from selling custom songs for people. Songfinch was named...