Polymarket and Kalshi: Financial Tools or Casinos?

Prediction markets like Polymarket and Kalshi have had a big year in 2025, but what are they really? Securities? Derivatives? Sportsbooks? They may be all of the above. Listen to my breakdown on how these markets have evolved over time, and what led to their current rise today. We then dive into the opportunities, risks, and the regulatory challenges that may shape their future. CHAPTERS 02:54 The Origin of Prediction Markets 06:43 Polymarket, Kalshi, and Modern Prediction Markets 09:16 Regulation and What’s Next 09:31 Bucket A: Policy, Finance, and Economics 13:36 Bucket B: Sports, Entertainment, and Pop Culture SPONSORS Chartmetric: Listen in for our Stat of the Week Too Lost: empowering artists with tools to manage, distribute, and grow their music independently. TRAPITAL Where technology shapes culture. New episodes and memos every week. Sign up here for free.

People say they miss when MTV played music videos, but their viewing habits say otherwise! We revisited one of our most popular episodes from 2023, but trimmed it down to include the best parts. I’m joined by Zack O’Malley Greenburg to unpack MTV’s rise from a scrappy video platform to a cultural powerhouse. We break down breakthrough moments like Michael Jackson’s “Billie Jean”, the rise of reality TV, the networks influence, rise, fall, and what’s next? CHAPTERS 01:04 The Birth of MTV 04:45 MTV's Business Model 13:01 Cultural Impact of Influence 21:28 Rise of Reality TV 29:59 MTV ‘s Decline SPONSORS Chartmetric: Listen in for our Stat of the Week beatBread : A music funding platform that empowers independent artists to access advances on their streaming income while keeping 100% ownership of their music. Splice, a cloud-based music creation platform offering millions of royalty-free samples, plugins (via rent-to-own), and AI-powered tools to inspire creators everywhere GUEST Zack O’Malley Greenburg, Author, Empire State of Mind TRAPITAL Where technology shapes culture. New episodes and memos every week. Sign up here for free.

We continue our Trapital Summit series with Dan and MiDIA Research’s Tati Cirisano sharing bold predictions from Trapital Summit attendees and sharing their thoughts. We debate the long-term viability of major record labels, whether a Netflix + Spotify merger make sense (we recorded this before the podcast partnership!), we also discussed whether we’ll return to mass mainstream monoculture, future growth opportunities, and which new opportunities will be unlocked by AI-powered tools. CHAPTERS 01:47 Future of Major Labels? 03:58 Will Netflix and Spotify Ever Merge? 05:52 A Return to Monoculture? 09:06 Unprecedented Industry Growth? 10:30 Will AI-Driven Labels Be The Future? SPONSORS Splice: Splice Instrument is here. Real instruments, meticulously crafted, and authentically crafted Chartmetric: Listen in for our Stat of the Week GUEST Tatiana Cirisano, VP Music Strategy, MIDiA Research TRAPITAL Where technology shapes culture. New episodes and memos every week. Sign up here for free.

This episode is in partnership and collaboration with our friends at The Recording Academy You’ll hear our deep dive on what we can learn from this years Grammys with our usual analysis and a few select guests including: Panos Panay (President of The Recording Academy), Tati Cirisano (MIDiA Research), Zack O’Malley Greenburg, author and investor. We discuss the biggest takeaways from the 2026 nominations, the rise of international music, how the voting body has evolved, and the economic lift of a Grammy win. CHAPTERS 01:41 - Biggest takeaways 05:41 - Tati Cirisano joins us 13:02 - Panos Panay joins us 17:10 - Which past Grammys would have changed 21:52 - The Grammy Bump 33:10 - Zack Greenburg joins us SPONSORS The Recording Academy Chartmetric: Listen in for our Stat of the Week Tidal: Win $100k with the Tidal Upload Contest GUESTS Panos Panay, President, The Recording Academy Tatiana Cirisano, VP Music Strategy, MIDiA Research Zack O’Malley Greenburg, Author, Empire State of Mind TRAPITAL Where technology shapes culture. New episodes and memos every week. Sign up here for free. RESOURCES What is the Economic Value of a GRAMMY in Today’s Industry? - Chartmetric and Will Page

At our Trapital Summit, Nathan Hubbard joined me in stage to discuss Firebird Music’s investment thesis, working with Yungblud, and the business of Taylor Swift. CHAPTERS 04:06 Firebird’s Mission 06:46 Yungblud’s Case Study 14:16 Investing in Management Companies 21:03 Finding New Talent 23:34 Is Taylor Swift the Best CEO in Music? SPONSORS Chartmetric: Listen in for our Chartmetric Stat of the Week. Splice: Learn more about Splice’s brand new virtual INSTRUMENT LINKS & SOURCES ⁠Trapital newsletter⁠⁠ Trapital Summit 2025⁠ Guests: Nathan Hubbard, ⁠Firebird Music⁠⁠ Every Single Album⁠ Podcast TRAPITAL Where technology shapes culture. New episodes and memos every week.

We continue our Trapital Summit series with Jason Sklar, a partner at Shamrock Capital, to explore music rights as an asset class, as well as gaming, film, and more. We discuss Shamrock’s perspective, market trends, valuation approaches, the role of AI, and cross-industry opportunities. 02:27 State of Music Rights Investing 09:37 Shamrock’s Investment Approach 16:01 AI, Gaming, and Music 19:39 Why Investing in Film is a B2B Business 20:13 What’s Next for Catalog Deals This episode is brought to you by SoundCloud for Artists, the all-in-one platform that empowers artists to distribute music, grow their audience, and get paid directly. From uploads to insights, SoundCloud helps creators take control of their careers. Listen in for our Chartmetric Stat of the Week.

We continued our Trapital Summit series with our talk with Udio CEO Andrew Sanchez and MIDiA Research’s Tati Cirisano. AI is rapidly transforming how music is created, distributed, and experienced. You’ll hear them unpack the challenges and opportunities shaping this new era of sound. From redefining creativity to fostering trust between artists and technology, we explore how collaboration, ethics, and innovation can drive a more equitable and inspiring future for the music industry. 03:36 AI Music: Trends and Future 08:11 What Sets Udio Apart 14:06 Trust and Fair Use in AI 21:19 Future Vision and Rapid Fire This episode is brought to you by Laylo, a platform built for artists, creators, and live-event teams that helps turn shows into fandom. Laylo powers drops, tour campaigns, fan lists, SMS & DM outreach, and more to grow engagement and enable deeper connections. Listen in for our Chartmetric Stat of the Week.

At the Trapital Summit, we were joined by the CEO of VERZUZ, Steve Pamon. His career is all about turning events into big moments, from his time at McKinsey, HBO, NFL, WWE, IMAX, and more. We discussed how major shows scale into franchises, covering team execution, fan value, storytelling, and lessons from Beyoncé, Roger Goodell, and more. 03:50 Story and Execution in Live Events 09:49 Music Industry Challenges 16:23 WWE and IMAX Takeaways 24:02 What’s Next for Verzuz This episode is brought to you by Laylo, a platform built for artists, creators, and live-event teams that helps turn shows into fandom. Laylo powers drops, tour campaigns, fan lists, SMS & DM outreach, and more to grow engagement and enable deeper connections. Listen in for our Chartmetric Stat of the Week.

We’re continuing our Trapital Summit series with TuneCore CEO Andreea Gleeson. You’ll hear her and Billboard’s Taylor Mims discuss how TuneCore empowers artists worldwide, how indie artists break through the noise, successes, challenges, and more. 03:48 Wins and Milestones 09:55 Superfans Opportunities 12:57 Future Tools for TuneCore Artists 15:33 Indie Artist Trends This episode is brought to you by beatBread a music funding platform that empowers independent artists to access advances on their streaming income while keeping 100% ownership of their music. Listen in for our Chartmetric Stat of the Week.

We’re continuing our Trapital Summit series. In this episode, we’re with Kakul Srivastava, CEO of Splice, to discuss how technology is reshaping music. From Splice’s acquisition of Spitfire Audio to the rise of AI-powered tools, we explore innovation, M&A lessons learned, and more. 03:51 Acquiring Spitfire Audio 10:24 Product and Data-Driven Growth 16:47 Royalty-Free Tradeoffs 20:22 Future of AI This episode is brought to you by Splice, a cloud-based music creation platform offering millions of royalty-free samples, plugins (via rent-to-own), and AI-powered tools to inspire creators everywhere Listen in for our Chartmetric Stat of the Week.