Best Colossus | Investing Podcasts (2025)

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Asurion: Retracing the Path to 100 times 50x with Irv Grousbeck - [50X, S2 EP.3] 59:24

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5M ago59:24

59:24

Today’s episode is the finale of our season on Asurion, the world’s leading tech care company with more than 300 million customers. In an interview with legendary long-time director, Irv Grousbeck, we discuss Irv’s path to investing in Asurion, his stewardship across several cohorts of PE ownership, and compare Asurion to Irv’s previous power law e…

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Asurion: The Flywheel Era (‘01-‘07) with Kevin Taweel - [50X, Asurion S2 EP.2] 1:01:05

5M ago1:01:05

1:01:05

Today’s episode is the second in a series of three on Asurion, the world’s leading tech care company with more than 300 million customers. In an interview with Co-Founder and Chairman Kevin Taweel, we dive deep into Asurion’s divinely discontent culture, hyper-rational approach to talent management, growth over $1 billion in sales, and transformati…

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Asurion: The Early Days (‘95-‘01) with Kevin Taweel - [50X, S2 EP.1] 1:08:42

6M ago1:08:42

1:08:42

Today’s episode is the first in a series of three on Asurion, the world’s leading tech care company with more than 300 million customers. In an interview with Co-Founder and Chairman Kevin Taweel, we explore Asurion’s scrappy origins in roadside assistance, acquisitive entry into handset insurance, contentious capital allocation decisions, and much…

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Season 2: Asurion - (50X, Trailer) 2:40

6M ago2:40

2:40

50X is back for Season 2! This season centers on Asurion, the world’s leading tech care company with over 300 million customers. Hosted by Will Thorndike, author of The Outsiders and a co-founder at Compounding Labs, 50X aims to dissect the anatomy of investments that have appreciated at least 50-fold. We track the often circuitous route to excepti…

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Mastering Podcast Monetization with Matthew Sherry - [Making Media, EP.62] 59:05

1+ y ago59:05

59:05

Our guest today is Matthew Sherry, co-founder and CEO of Platform Media. Founded in 2021, the business is home to some of the UK’s biggest podcasts and was acquired earlier this year for an eight-figure sum. The business was founded to solve the two biggest problems in podcasting: distribution and monetization. Through a savvy social strategy and b…

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Every Things, Everywhere, All at Once with Dan Shipper - [Making Media, EP.61] 58:47

1+ y ago58:47

58:47

Our guest today is Dan Shipper, the co-founder and CEO of Every. Every started at the beginning of the pandemic as a bundle of business newsletters written by different authors. While writing is still at the heart of the business, the model has shifted focus to a daily newsletter that is an essay on technology, productivity, or AI. Dan and his team…

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Tim Ferriss - Curating Curiosities - [Invest Like the Best, REPLAY] 1:24:30

1+ y ago1:24:30

1:24:30

This week, we bring you two titans of the podcasting world, Tim Ferriss and our very own Colossus chairman, Patrick O’Shaughnessy. We’re biased, but I think these two are two of the best interviewers in the world, and they recorded this conversation on Invest Like the Best for the 10th anniversary of Tim’s podcast. Matt and I thought you, our preci…

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Undisputed Media Lessons with Mike Stricoff - [Making Media, EP.60] 57:01

1+ y ago57:01

57:01

Our guest today is sports media veteran Mike Stricoff. Mike spent a decade producing live sports talk on national TV, first working at MLBN before moving to Fox Sports, where he helped launch Undisputed. Mike worked on that show alongside Skip Bayless, Shannon Sharpe, and others as the main line producer. In 2017, he left national TV for tech, goin…

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Business, Culture, and Content with Emily Sundberg - [Making Media, EP.59] 1:03:39

1+ y ago1:03:39

1:03:39

Welcome back to Making Media. Our guest today is Emily Sundberg. Like many of our most creative guests, Emily has a wide-ranging background. For her day job, she writes her newsletter, Feed Me, which tracks valuable early trends in the consumer and brand space. If you want to know what's going to happen six months from now, read Emily's newsletter …

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Building a Podcast Empire with Jack Davenport - [Making Media, EP.58] 43:56

1+ y ago43:56

43:56

Our guest today is Jack Davenport. Jack is the Managing Director and Co-Founder of British-based Goalhanger Podcasts. Goalhanger is the largest independent podcast network in the U.K. and likely the world outside of the U.S. Its stable of shows do 30 million downloads a month. Goalhanger got its first big breakthrough with the excellent history pod…

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Decoding Media with Peter Kafka - [Making Media, EP.57] 46:30

1+ y ago46:30

46:30

Our guest today is Peter Kafka. If you've listened to media podcasts, you've likely listened to Peter's Recode Media. It has been a fixture in the industry for years. Peter recently announced he's going back to Business Insider, which is notable because he was the first hire way back when it was known as Silicon Valley Insider in 2007. Given Peter …

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Read What Matters with Ben Springwater - [Making Media, EP.56] 59:01

1+ y ago59:01

59:01

Our guest today is Ben Springwater. Ben is the founder of Matter, a reading app that pulls everything you want to read into one place with curation, audio, and more. There are constant frustrations with how we get served media, as there's infinite content, and it's harder and harder to separate the good from the bad. Ben is working to solve that pr…

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A 30,000 Foot View of Niche Media Businesses with Jon Ostrower - [Making Media, EP.55] 50:01

1+ y ago50:01

50:01

Our guest today is the preeminent aviation journalist, Jon Ostrower. Jon is the founder and editor-in-chief of The Air Current, which he started in 2018. It's an independent subscription media business focused on the global aerospace and aviation industries. Jon started blogging about the airline industry as a 22-year-old while working in politics,…

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Spike Eskin - What Sports Media Can Teach Us - [Making Media, REPLAY] 1:09:19

1+ y ago1:09:19

1:09:19

If you make a podcast or like sports, you will enjoy this episode. Spike Eskin runs all of the programming at New York's WFAN, the original and biggest sports talk radio station, and he's only the second person ever to have that job. Now you're probably thinking, doesn't everyone just listen to podcasts now? Well, the answer to that is no, but don'…

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Building The Athletic with Adam Hansmann - [Making Media, EP.54] 55:14

1+ y ago55:14

55:14

Our guest today is Adam Hansmann, co-founder of The Athletic. The Athletic launched in 2016 when the idea of paying for content was still considered contrarian and newspapers & local coverage of sports was dwindling. Yet Adam and his co-founder built something that they wanted, solving a problem they experienced in their own lives and riding this m…

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Walking the Fairways with CBS Sports Writer Kyle Porter - [Making Media, EP.53] 51:11

2y ago51:11

51:11

Our guest this week is CBS Sports Writer Kyle Porter. Kyle writes and podcasts about golf for CBS, and he has done so since 2012. In 2021, Kyle wrote his first book, "Normal Sport," which was born out of a running joke with his audience about the absurdities of golf. He has now written and self-published three books and writes a newsletter under th…

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2023 Recap - [Making Media, EP.52] 29:57

2y ago29:57

29:57

We reflect on Making Media's inaugural year and 2023 as a whole for the podcasting world. From shifts in the macro podcast environment to our most memorable recordings, we round up our first year and look to the next. For the full show notes, transcript, and links to the best content to learn more, check out the episode page HERE. ----- Making Medi…

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The Evolution of FreightWaves with Craig Fuller - [Making Media, EP.51] 1:03:59

2y ago1:03:59

1:03:59

Today's guest is Craig Fuller, Founder and CEO of FreightWaves and CEO of FLYING Magazine. We get into some of the early observations that Craig had when he was building out FreightWaves, which is a software data business with a media empire sitting around it. He shares the challenges associated with fundraising for a media business and why the mar…

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A Lesson in Paid Growth with Jonathan Becker - [Making Media, EP.50] 54:59

2y ago54:59

54:59

Our guest today is Jonathan Becker, Founder of Thrive Digital. Paid growth is a complex topic and it is something that we reference quite a bit on the show, but we've never really dug in. Jonathan and his team at Thrive have deployed over $3.5 billion in paid acquisition budgets on behalf of their client base. Naturally, that makes him an ideal gue…

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The North Face Presents with Kaki Orr - [Making Media, EP.49] 54:28

2y ago54:28

54:28

Today, we’re joined by Kaki Orr, the Creative Director for Branded Content at The North Face. After a career as a professional skier where she was sponsored by The North Face, Kaki joined the company and has since led the charge to create mesmerizing films of their athletes skiing, climbing, and running across many of the world’s most remote and br…

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Best Books, Movies, and Podcasts of 2023 with Web Barr - [Making Media, EP.48] 51:28

2y ago51:28

51:28

Part of our mission with Making Media is to highlight great content across the internet. Today, we're sharing our favorite pieces of media from the past year and to help us sift through the deluge of content, we have a special returning guest - media aficionado Web Barr. Web is a multiple-time Webby Award and Communication Arts-winning producer at …

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The Story of Stripe Press with Tamara Winter - [Making Media, EP.47] 58:37

2y ago58:37

58:37

Our guest today is Tammy Winter, the Commissioning Editor of Stripe Press. As the name suggests, Stripe Press is a division within Stripe. Founded in 2010 by two Irish brothers, John and Patrick Collison, Stripe is a payment processing business with a mission to "increase the GDP of the internet". From the surface, there doesn’t seem to be great sy…

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The MCU: A Marvel Deep-Dive with Joanna Robinson - [Making Media, EP.46] 1:10:02

2y ago1:10:02

1:10:02

Today we are talking Marvel. It's the cinematic universe that's made over $30 billion at the box office (and that's just the Hollywood piece). Our guest today is Joanna Robinson, Podcaster and Culture Critic for The Ringer. Joanna wrote "MCU: The Reign of Marvel Studios," a revealing behind-the-scenes history of the cultural phenomenon. We cover th…

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Inside Architectural Digest with Amy Astley - [Making Media, EP.45] 56:39

2y ago56:39

56:39

Our guest today is Amy Astley, global editorial director and editor-in-chief of the Iconic Architectural Digest. It's rare to find a brand like AD that has a hundred-year-old history and effectively balances that rich heritage while still being the pulse of the market. Amy talks about the cultural currency that exists with the AD magazine and what …

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7 More Nuggets of Media Wisdom - [Making Media, EP.44] 36:36

2y ago36:36

36:36

In early October, Matt put together seven insights that he's learned and implemented from this show. Today, it's Dom's turn to pull out his favorite lessons that guests have shared with us and how we've put them to use in our own business, Colossus. Enjoy seven more nuggets of media wisdom. For the full show notes, transcript, and links to the best…

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The Ringer’s Press Box with Bryan Curtis - [Making Media, EP.43] 58:22

2y ago58:22

58:22

We are joined today by Bryan Curtis, Editor-at-Large at The Ringer. Bryan writes excellent columns on theringer.com and hosts The Press Box, which happens to be the show with our favorite podcast episode of this past year. We gushed with Bryan over that particular podcast episode with Wright Thompson and we also hit on a wide range of media topics:…

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The Power of a Newsletter with Lenny Rachitsky - [Making Media, EP.42] 1:02:21

2y ago1:02:21

1:02:21

Today we welcome Lenny Rachitsky to Making Media. Lenny has built the biggest business publication on Substack, "Lenny’s Newsletter," with well over 500,000 readers. It started in 2019 as an advice column and since starting the newsletter, he has built a thriving podcast, community, and job board. Lenny’s world has become the destination for produc…

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Inside Colossus - Debriefing a Successful Launch - [Making Media, EP.41] 28:04

2y ago28:04

28:04

Last week, we launched a new Colossus podcast called Art of Investing. It was our biggest and most successful launch ever so we wanted to share the tactics we put in play to help that show off to a fast start. We hope you’ll find them useful and we’ll be back with our normal interview episode on Thursday. For the full show notes, transcript, and li…

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Media Playbooks: Events, New Verticals, and More with Jacob Donnelly - [Making Media, EP.40] 41:13

2y ago41:13

41:13

This is Matt Reustle and today I am joined by Jacob Donnelly. Jacob is the founder at A Media Operator and publisher from the Morning Brew. Jacob has long been involved in the media space, with a persistent interest in ideas on building a sustainable media company, leading him to launch his own. A Media Operator is a community with a high caliber o…

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7 Nuggets of Media Wisdom - [Making Media, EP.39] 26:32

2y ago26:32

26:32

Today on Making Media Matt shares his top 7 bits of media wisdom that he has thoughtfully curated during his efforts to build a media company. Each individual guest and episode offers a new takeaway, and Matt attempts to find the thread that goes between all of these lessons and create an actionable summary. Studying great founders, learning from t…

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Life as a Writer with David Coggins - [Making Media, EP.38] 47:31

2y ago47:31

47:31

Today we have a special guest on Making Media. There are few people who write and live like David Coggins. David has a way of maintaining his creative identity while still adopting many of today's tools. He writes books, and he writes on his Substack, The Contender. We talked to David about his process for writing, what he is or is not sacred about…

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The Voice of Pickleball with The Dink’s Thomas Shields - [Making Media, EP.37] 55:53

2y ago55:53

55:53

This week we cover another niche media business. Our guest, Thomas Shields, launched The Dink in late 2020 and has quickly grown it to become the media authority on the booming sport of Pickleball. Across its newsletter, podcasts, videos, blogs, and more, The Dink offers everything you could want to know about the sport. And we discuss the whole jo…

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More with Less Media with Brian Morrissey - [Making Media, EP.36] 1:01:50

2y ago1:01:50

1:01:50

Today we're sitting down with Brian Morrissey and getting back to the guts and glory days of the media industry. In 2021, Brian founded The Rebooting - a newsletter publication focused on the mechanics of building sustainable media businesses. Prior to The Rebooting, he spent a decade building Digiday and had a nice stint as editor at Adweek. We ge…

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Matt Levine - Wall Street’s Art Critic - [Making Media, EP.35] 57:18

2y ago57:18

57:18

Today we speak with the Wall Street Wonder, Matt Levine. Matt's Bloomberg column, Money Stuff, has become a must read for most of the finance community. It's that rare place where you get laughter, learning, and complex topics. During the conversation, we talk with Matt about his ability to translate those complex topics, how his early legal career…

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Flying Under the Radar with Flightradar24 and Fredrik Lindahl - [Making Media, EP.34] 52:49

2y ago52:49

52:49

Today, we’re speaking to the CEO of Flightradar24, Fredrik Lindahl. Flightradar24 might not qualify as a traditional media company but it does attract millions of people to its content every day and I, for one, am a huge fan. It is the clear leader in flight tracking globally and its stats are wildly impressive. They track around 250,000 flights ev…

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Courtside with The Tennis Podcast and David Law - [Making Media, EP.33] 1:01:25

2y ago1:01:25

1:01:25

Our guest today is David Law. David is a broadcaster and co-founder of the biggest podcast in tennis, aptly named - The Tennis Podcast. This is an exceptional conversation on what it takes to be successful as a podcaster. David and his co-presenters have recorded over 1000 episodes. They went 5 years without earning a penny from the podcast. It too…

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The Man Behind Richard Branson and Virgin’s Brand – Greg Rose – [Making Media, EP.32] 50:18

2y ago50:18

50:18

Our guest today is Greg Rose, who has worked closely with Richard Branson at Virgin for nearly 15 years. As Virgin’s Content and Communications Director, Greg is responsible for what you see from Richard or Virgin’s companies across social media, Richard’s autobiographies, and more traditional public outlets. He is the man who convinced Virgin’s fa…

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How to Start a Podcast - [Making Media, EP.31] 47:26

2y ago47:26

47:26

Today, we’re answering a question we get a lot. How do you start a podcast? We’ll tell you everything you need to know, from hardware to software to thoughts on content and format. Scroll down to our shownotes for a full list of the products and services discussed. Enjoy. For the full show notes, transcript, and links to the best content to learn m…

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Finding Your Favorite Thing with Liberty RPF - [Making Media, EP.30] 1:10:06

2y ago1:10:06

1:10:06

Our guest today is someone we've mentioned frequently on this podcast, Liberty RPF. It's difficult to define exactly what Liberty writes about - but that might explain why we find his work so fascinating. He is a curator of great content and acts a sherpa for his audience, pushing them to find new things that resonate with them. It's a role that fe…

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Is Forbes Worth $800 Million? - [Making Media, EP.29] 43:45

2y ago43:45

43:45

Today’s episode is a little different. Rather than bring a guest on, we’re going to break down how Forbes works. As former investors now operating in the media space, a few brands particularly intrigue us. Forbes is near the top of that list, not least because its current owners are trying to sell it for $800 million. It has been around for over 10…

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Making Epic Acquisitions with Kevin Espiritu - [Making Media, EP.28] 1:01:22

2+ y ago1:01:22

1:01:22

Our guest today is Kevin Espiritu. Kevin is the founder and CEO of the world’s most followed gardening brand and online garden store – Epic Gardening. Matt and I had been following Epic and Kevin’s journey for a while but when we met him in person at Capital Camp in May, we knew we had to get him on the show. Since going full time on Epic Gardening…

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Rethinking the Membership Model with Jay Clouse - [Making Media, EP.27] 57:18

2+ y ago57:18

57:18

Our guest today is Jay Clouse. Past guest Chris Hutchins told us that Jay had given him some of the best, contrarian advice on memberships. Naturally, that was enough of a hook for us so we got on the phone and asked him how to build a community around your product. Please enjoy this conversation with Jay Clouse. For the full show notes, transcript…

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Om Malik on his Conversation with Brunello Cucinelli - [Making Media, EP.26] 55:34

2+ y ago55:34

55:34

Our guest today is Om Malik. Back in 2015, Om published an interview, or what might better be described as a conversation, with Brunello Cucinelli. It's a truly special conversation, and I know many people that find it's a life changing conversation. Brunello seems to be the rare, maybe the only, billionaire that has somehow found balance in life. …

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Building the Disney of B2B with Adam Ryan - [Making Media, EP.25] 1:01:35

2+ y ago1:01:35

1:01:35

Our guest today is Adam Ryan, the founder of Workweek. At Colossus, we're big fans of Workweek. We've hosted the Wolf of Franchises for an excellent Business Breakdown on Orangetheory and I'm an avid reader of Adam's Perpetual newsletter. For this conversation, we discuss the ongoing shift towards individuals over institutions, how media companies …

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Nailing a Niche in Radio with Louis Timpany - [Making Media, EP.24] 43:14

2+ y ago43:14

43:14

Today, we speak with the founder of the UK’s fastest growing radio station, Louis Timpany. Louis started Fix Radio in 2017 after realising that the power users of radio weren’t being served at all. He was working on a construction site when he noticed that the biggest source of arguments, day-in-day-out, was about the radio. No-one listens to radio…

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Top Content of 2023 with Web Barr - [Making Media, EP.23] 57:39

2+ y ago57:39

57:39

Part of our mission with Making Media is to highlight great content across the internet. Earlier this year, we talked about influential business essays with one of our favorite writers, Packy McCormick. Today, Web Barr joins us to review the best of what we’ve seen, read, and heard so far in 2023. Web is a formidable media operator. He is a multipl…

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Inside Colossus - Reflections on Hosting a Podcast with Eric Golden - [Making Media, EP.22] 1:06:23

2+ y ago1:06:23

1:06:23

Today, we speak with one of our esteemed hosts, Eric Golden, in our first in-person Making Media episode. After a career in the bond markets at Fidelity, Eric now hosts Colossus show, Web3 Breakdowns. As is customary with our Inside Colossus episodes, we go behind the mic with Eric and discuss what hosting a podcast is really like. What’s changed, …

1
All the Media Growth Hacks with Chris Hutchins - [Making Media, EP.21] 1:00:03

2+ y ago1:00:03

1:00:03

Our guest today, Chris Hutchins, is a bit of a podcast whisperer and has some of the most unique ideas in podcasting and in media. Before Chris went full-time with his All the Hacks podcast, he co-founded two businesses. One he sold to Google, the other he sold to Wealthfront. He also spent time as a partner at Google Ventures before going full-tim…

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Morgan Housel on Writing - [Making Media, EP.20] 1:04:09

2+ y ago1:04:09

1:04:09

Today, we are going behind the scenes with a master of his craft, Morgan Housel. In the investing world that Matt and I are from, there are few – if any – who make better content than Morgan. His blog has been a personal favourite for years and his first book, The Psychology of Money, just crossed 3 million sales. So we reached out to see if he’d t…

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IP: Making, Managing, and Monetizing with Legendary Comic Book Artist Todd McFarlane - [Making Media, EP.19] 1:24:55

2+ y ago1:24:55

1:24:55

We are diving deep into the world of intellectual property with legendary comic book artist Todd McFarlane. IP sits at the heart of many media discussions and it's something we are very curious about. Todd revitalized Spider-Man, co-created Venom, and was the sole creator of Spawn. He also founded Image Comics just over two decades ago, and that ha…