Making Media

Making Media

How to build a media business by two outsiders learning the craft. Matt Reustle and Dom Cooke have decades of experience in investing but almost none in the media industry. In each episode, they talk to great media operators, document their own media building efforts, and dissect their favorite business content. Join these two content junkies in their fight to save long-form media against the attention span crisis. Join the resistance. Learn more and stay up to date at www.joincolossus.com. An entrepreneurship show, by entrepreneurs, for the entrepreneur.

  1. 18 JUL

    Mastering Podcast Monetization with Matthew Sherry

    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 bespoke partnerships, it has found unique solutions to both of those issues. We get into all the details of how they’ve managed to crack the code, where inspiration for the business came from, and what’s next after the capital injection from their recent acquisition. Please enjoy this conversation with Matthew Sherry.  For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ----- Making Media is a property of Colossus, LLC. For more episodes of Making Media, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @ReustleMatt | @domcooke | @MakingMediaPod | @JoinColossus  Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes (00:00:00) Welcome to Making Media (00:01:44) The Genesis of Platform Media (00:04:26) Innovative Podcast Strategies (00:05:22) Monetization and Marketing Tactics (00:06:06) The Good, The Bad, and The Rugby Success Story (00:07:24) Expanding Beyond Podcasts (00:10:33) Challenges and Future Plans (00:13:48) Social Amplification and Content Distribution (00:15:40) Revenue Models and Commercial Strategies (00:21:02) Adapting to Market Changes (00:30:52) Exploring Partner Deals and Opportunities (00:32:59) Benefits of Partnering with Big Companies (00:35:20) Engaging Talent for Successful Partnerships (00:37:43) Challenges and Success in Branded Content (00:41:09) The Big Announcement: Business Acquisition (00:45:16) Looking to the US Market for Inspiration (00:48:36) Debrief

    59 min
  2. 16 MAY

    Every Things, Everywhere, All at Once with Dan Shipper

    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 have also built adjacent business lines and even incubated a startup called Lex that they spun out last year. We talk through the evolution of Every, which really gets to the core of what's both great and challenging about media companies. He goes into detail about his entrepreneurial spirit that started way back in fifth grade, how he's become laser-focused on AI recently, launching a great podcast on the subject, and chatGPT specifically. Please enjoy this conversation with Dan Shipper. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ----- Making Media is a property of Colossus, LLC. For more episodes of Making Media, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @ReustleMatt | @domcooke | @MakingMediaPod | @JoinColossus  Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes  (00:00:00) Welcome to Making Media (00:02:10) Dan Shipper's Entrepreneurial Journey From Fifth Grade to CEO (00:06:06) Embracing Writing: A Founder's Shift in Identity (00:11:13) Major Pivots and Growth for Every (00:13:11) Challenges and Innovations in Building a Newsletter Business (00:18:10) Analyzing Puck's Business Model and Its Future (00:21:03) The Power of Incubation and Diversification in Media (00:27:59) Balancing Creative and Operational Roles in Leadership (00:30:51) The Deliberate Focus on Chat GPT (00:32:39) Challenges of Specialization in Content Creation (00:35:40) Impact of AI on Creativity and Work (00:41:22) The Unique Dynamics of Chatbots vs. Search Engines (00:45:43) Exploring Think Week and Creative Processes (00:48:28) Debrief

    59 min
  3. 25 APR

    Tim Ferriss - Curating Curiosities

    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 precious Making Media audience, would enjoy it too, as Tim touches on so many themes that we speak with guests about on this show. Please enjoy this great conversation with Tim Ferriss and Patrick O'Shaughnessy. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- Making Media is a property of Colossus, LLC. For more episodes of Making Media, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @ReustleMatt | @domcooke | @MakingMediaPod | @JoinColossus  Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes: (00:00:00) - Welcome to Invest Like the Best (on Making Media) (00:03:32) - The Evolution of Podcasting with Tim Ferriss (00:09:56) - Crafting Meaningful Conversations (00:13:26) - What Makes Tim Feel The Most Alive  (00:24:06) - Who Tim Considers To Be His Mentors (00:29:06) - The Ingredients Of A World Class Performance (00:31:06) - The Business Side of Podcasting (00:43:15) - Identifying Emerging Trends (00:50:12) - Lessons From Building a Small, Efficient Team (00:52:32) - The Power of Constraints in Personal and Professional Growth (00:53:10) - Innovating Against the Grain (Anti-Video Experiment) (00:54:54) - Navigating Fame, Money, and Power (01:02:00) - The Impact of Sharing Difficult Stories (01:06:18) - Meta-Learning: A Framework for Fast, Effective Learning (01:12:32) - Reflecting on a Decade of Podcasting & What’s In Store (01:24:41) - The Kindest Thing Anyone Has Ever Done For Tim

    1h 25m
  4. 11 APR

    Undisputed Media Lessons with Mike Stricoff

    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, going to work at Snap where he led their sports and gaming content. And, more recently, he has launched his own business working as an adviser to digital media companies and connecting investors & content producers. We tap into all his experience in a discussion around personality-driven media businesses and how that has evolved both at a national scale and for independent creators. Please enjoy our conversation with Mike Stricoff. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ----- Making Media is a property of Colossus, LLC. For more episodes of Making Media, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @ReustleMatt | @domcooke | @MakingMediaPod | @JoinColossus  Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes  (00:00:00) Welcome to Making Media (00:02:15) Behind the Scenes of The Launch of Undisputed (00:04:00) The Art of Personality-Driven Media (00:08:18) Catering to The Host Vs The Audience (00:13:38) Fostering Chemistry Between Co-Hosts  (00:17:51) Mike’s Experience Launching FS1 (00:21:48) Mike’s Transition to Snap & A New Frontier in Sports Content (00:31:05) The Pros and Cons of Algorithm-Driven Content (00:34:48) The Evolution of Content Creators From Traditional Media to YouTube Stars (00:39:06) Advice for Aspiring Content Creators (00:40:40) Bridging Creators with the Investment World (00:45:16) Debrief

    57 min
  5. 21 MAR

    Business, Culture, and Content with Emily Sundberg

    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 tomorrow.  She also writes for New York magazine and GQ, she's been featured in the New York Times, and she's published a documentary. We talk about how she's built up this incredibly valuable, long, diversified list of sources while not being a traditional journalist. And we hit on what's happening in culture and documentaries too. Please enjoy this conversation with Emily. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ----- Making Media is a property of Colossus, LLC. For more episodes of Making Media, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @ReustleMatt | @domcooke | @MakingMediaPod | @JoinColossus  Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes  (00:00:00) Welcome to Making Media (00:02:46) First Question - The Art of Trendspotting (00:08:57) The Evolution of Emily's Newsletter ‘Feed Me’ (00:14:00) Writing for A Magazine vs A Newsletter (00:17:19) The Art of Making Stories Stick (00:21:17) Understanding Her Audience (00:26:04) Daily Content Creation: Insights into the Writing Process (00:29:22) The Unique Voice of the Newsletter: Entertainment and Opinions (00:32:12) Diving Into Documentary Filmmaking (00:35:23) The Financial Realities and Creative Challenges of Documentary Making (00:38:27) Navigating the Documentary World and Future Projects (00:45:13) Diving Deep into Direct Investments and Business Models (00:45:55) The Solo Journey of Managing a Newsletter (00:56:31) Debrief

    1h 4m
  6. 7 MAR

    Building a Podcast Empire with Jack Davenport

    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 podcast called “The Rest Is History,” and they've since grown into other verticals like politics, finance, football, and entertainment. It was great fun to talk all things podcasting with someone who's taking the medium by storm. Please enjoy this conversation with Jack Davenport.  For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ----- Making Media is a property of Colossus, LLC. For more episodes of Making Media, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @ReustleMatt | @domcooke | @MakingMediaPod | @JoinColossus  Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes  (00:00:00) Welcome to Making Media (00:02:06) First Question - The Evolution of GoalHanger and Its Podcasts (00:04:19) The Success of 'The Rest is History'  (00:07:36) The Transition from Video to Audio (00:10:18) Revenue Streams and Business Model (00:14:45) The Importance of Hosts and Talent in Podcasting (00:18:16) Marketing Strategies and Branding (00:22:54) Partnerships with Other Media Businesses (00:25:24) The Importance of Retaining Intellectual Property (00:27:11) The Power of Cross-Promotion and Audience Growth (00:32:01) The Impact of High-Volume Podcasting (00:34:19) The Future Vision for Goalhanger (00:36:29) Debrief

    44 min
  7. 22 FEB

    Decoding Media with Peter Kafka

    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 has seen a few cycles, we tried to key in on what is actually new versus what is cyclical. It was a treat to pepper him with questions on media. Please enjoy this conversation with Peter Kafka. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ----- Making Media is a property of Colossus, LLC. For more episodes of Making Media, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @ReustleMatt | @domcooke | @MakingMediaPod | @JoinColossus  Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes  (00:00:00) Welcome to Making Media  (00:02:24) First Question - Perspective on Media Companies Today (00:04:02) Challenges in Local News Business Models (00:07:05) The Impact of Netflix on the Media Industry (00:10:20) The Influence of YouTube on Media Consumption (00:14:11) The Shift in Media Business Models (00:17:56) The Success of The New York Times' Subscription Model (00:21:54) The Impact of AI and VR on Media (00:27:20) The Disconnect Between Media Perception and Reality (00:30:31) The Evolution of Podcasting and Its Impact on Media (00:35:03) Reflections on Interviewing Techniques and Challenges (00:39:55) The Future of Podcasting and Media Consumption (00:42:30) Debrief

    47 min
  8. 15 FEB

    Read What Matters with Ben Springwater

    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 problem.  He shares what it's like to build a product like Matter and gives insight into how Matter’s team makes decisions around the technical and human challenges that come into play.  An avid reader and content consumer himself, we then asked Ben for some of his favorite recommendations, all linked below. Please enjoy this conversation with Ben Springwater. Ben’s Recommended Content:  The Road to Self-Renewal  Basic Income, Not Basic Jobs: Against Hijaking Utopia The Weirdly Enduring Appeal of Weird Al Yankovic For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ----- Making Media is a property of Colossus, LLC. For more episodes of Making Media, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @ReustleMatt | @domcooke | @MakingMediaPod | @JoinColossus  Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes  (00:00) Welcome to Making Media (01:36) The Challenges of Building a Product Like Matter (03:41) The Power of Curation in the Digital Age (08:03) The Future of Recommendation Systems (15:26) The Challenges of Building a User-Centric Product (22:14) The Intersection of Reading and Listening in the Digital Age (25:12) The Business Model of Matter (27:04) Ben’s Recommendation #1: The Road to Self-Renewal  (33:14) Ben’s Recommendation #2: Basic Income, Not Basic Jobs: Against Hijaking Utopia (42:38) Ben’s Recommendation #2: The Weirdly Enduring Appeal of Weird Al Yankovic (51:19) The Importance of Being An Enthusiast (52:06) Debrief

    59 min

About

How to build a media business by two outsiders learning the craft. Matt Reustle and Dom Cooke have decades of experience in investing but almost none in the media industry. In each episode, they talk to great media operators, document their own media building efforts, and dissect their favorite business content. Join these two content junkies in their fight to save long-form media against the attention span crisis. Join the resistance. Learn more and stay up to date at www.joincolossus.com. An entrepreneurship show, by entrepreneurs, for the entrepreneur.

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