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Colossus | Investing & Business Podcasts

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.

Making Media

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.
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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

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

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

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

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

Tim Ferriss - Curating Curiosities - [Invest Like the Best, REPLAY]

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

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

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

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

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

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

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

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

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

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

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, but he quickly became consumed by his passion and went on to work for Flight Global, The Wall Street Journal, and CNN before striking off to build his own media business. Throughout this conversation, he thoughtfully outlines the key decisions he's made in building The Air Current into the success it is today. Please enjoy this episode of Making Media with Jon Ostrower.

Listen to the Boeing Business Breakdown with Jon.

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
(02:35) First Question - Jon's Journey into Aviation Journalism
(03:44) The Miracle of Flight and the Aerospace Industry
(05:12) Jon's Early Career and the Birth of His Blog
(06:39) The Evolution of The Air Current
(10:24) The Importance of Quality Content and Audience Engagement
(16:05) The Challenges and Triumphs of Scaling a Media Business
(23:00) The Role of Passion and Expertise in Media Success
(29:25) The Importance of Owning Your Platform
(33:47) The Future of The Air Current and Closing Thoughts
(38:16) Debrief

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

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't worry. He's also got a podcast, a big one, and his podcast, The Rights to Ricky Sanchez, is frequently ranked at the top basketball podcast charts. It's only focused on a single team, the 76ers, but it's been big enough to get a full chapter in a book, and several audience gatherings have been featured on Sports Center highlights.
So he is the coach and he is the talent. During our conversation, we go through traits Spike looks for in audio hosts, the benefits and challenges of having practitioners like athletes sitting in the hosting chair, and differences in sponsorship dynamics between radio and podcasting frameworks for good content. Please enjoy this episode and conversation with Spike.

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 | @JoinColossus 

Show Notes
[00:00:00] Welcome to Making Media
[00:03:09] First question - Which traits he’d use to create the ideal audio host 
[00:06:55] Comparing podcasts to local radio and separating them into three categories
[00:08:43] Tricks to help hosts generate and create chemistry 
[00:14:48] Something that new hosts and newcomers to audio in general struggle with
[00:17:00] Effective ways to measure how the fans view your shows
[00:20:52] Whether you should place any weight on your most engaged listeners
[00:25:01] Differences in terms of a podcast covering a topic versus a local radio 
[00:30:09] The models and structure of the powerhouse that is radio advertising 
[00:33:39] Repeat advertising and his own sponsorship strategy 
[00:39:19] How much practitioner value comes into play about your show topic 
[00:44:37] The importance of non-consensus and controversial views 
[00:49:57] Whether or not official statements being made via social media is a passing trend or only the beginning 
[00:53:51] Coaching hosts when it comes to asking critical questions
[00:55:51] Debrief

Spike Eskin - What Sports Media Can Teach Us - [Making Media, REPLAY]

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 of both people and conversations for those in the digital media and online publishing world. We cover events, launching new verticals, B2B media, and who Jacob is closely watching operate in the media market. Please enjoy this conversation with Jacob Donnelly

Subscribe to Colossus's New Show: Art of Investing.
Buy a ticket to Patrick and David Senra's live show.

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 

Show Notes
(00:02:30) - (First question) What events mean to the media industry
(00:03:30) - The economic equation for business-to-business (B2B) events
(00:06:00) - What makes an event stand out from the rest
(00:07:30) - The future of virtual events in the realm of business
(00:10:45) - Making your event sustainable for the future
(00:13:30) - Integrating event businesses into broader sectors
(00:15:45) - A playbook for launching a new vertical in the event space
(00:20:30) - What the timeline for a new vertical looks like at Morning Brew
(00:26:00) - Handling sponsorship and exclusivity
(00:31:30) - Balancing the synergy between creators and brands
(00:34:45) - The best businesses to study in terms of media

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

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