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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Mastering Podcast Monetization with Matthew Sherry - [Making Media, EP.62]
Episode 62
Thursday, July 18, 2024 • Duration 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 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
Every Things, Everywhere, All at Once with Dan Shipper - [Making Media, EP.61]
Episode 61
Thursday, May 16, 2024 • Duration 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 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.
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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
(00:02:10) 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
Building The Athletic with Adam Hansmann - [Making Media, EP.54]
Episode 54
Thursday, January 25, 2024 • Duration 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 massive market expansion.
Adam shares a lot of the lessons that he took away from his experience building The Athletic and there is a lot to learn here. Please enjoy this conversation with Adam Hansman.
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
(00:01:45) First question - The playbook for subscription based businesses
(00:05:35) User-centric development, as opposed to advertiser-centric in media
(00:07:32) Adam’s reflections on the state of media and business development
(00:09:24) Managing feedback in the subscription model between readers and journalists
(00:12:21) The level of transparency in company meetings and how positivity affects the team
(00:15:02) Adam’s strategy when exploring alternative channels beyond Twitter to reach a broader audience
(00:17:16) Long-form journalism pieces and how it affected subscription performance
(00:18:42) The importance of bundling in The Athletic’s business
(00:22:09) Insights revealed when transitioning from local coverage to national content
(00:23:17) Adam’s key factors for fostering long-term alignment with employees
(00:25:36) How funding constraints in the early days influenced the business operations
(00:28:07) The implementation of The Athletic’s pricing model and the factors that have contributed to its consistency over time
(00:30:37) Balancing the app and website as an all-in destination versus leveraging other platforms
(00:32:43) Subsequent changes since being acquired by The Times
(00:34:03) Add-on businesses like events and merchandise and their relevance to the overall business strategy
(00:35:21) The integration of multimedia components such as podcasts and videos
(00:37:15) Navigating the transition into The Times, ensuring the preservation of existing culture and fostering alignment for the next phase
(00:39:51) Potential opportunities and initiatives that Adam is excited about
(00:42:59) Debrief
Walking the Fairways with CBS Sports Writer Kyle Porter - [Making Media, EP.53]
Episode 53
Thursday, January 18, 2024 • Duration 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 the same branding.
Even if you’re not a golf fan, there are so many interesting areas to explore about media with Kyle – from the rise of independent publishers like our friends at No Laying Up, working within a big media business, covering live sports, and the process of creating content independently. He can talk about the full spectrum.
I hope you enjoy this discussion with the great Kyle Porter.
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
(00:01:36) First question - Exploring common misconceptions in sports journalism
(00:06:36) Contrasting experiences in large corporations and smaller media outlets
(00:11:03) The highs and lows of golf storytelling
(00:14:23) Embracing the role of a golf ambassador
(00:19:11) Examining how monetization influences content creation
(00:26:56) The journey of writing a new book
(00:30:34) The process of generating original ideas
(00:32:33) Comparing live and recorded sports coverage
(00:37:47) Cultivating a unique voice in journalism
(00:39:59) Unveiling the distinct aspects of golf journalism
(00:41:23) Chronicling stories about Tiger Woods
2023 Recap - [Making Media, EP.52]
Episode 52
Thursday, January 11, 2024 • Duration 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.
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Making Media is a property of Colossus, LLC. For more episodes of Making Media, visit joincolossus.c
om/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
(00:00:48) First Question - Examining shifts in the podcast industry in 2023
(00:05:54- Evaluating Making Media's inaugural year
(00:08:44) The top 3 most popular Making Media episodes in 2023
(00:09:52) Highlighting Making Media’s most underrated episode
(00:14:00) Recalling the most unforgettable recording session
(00:16:14) Matt and Dom’s dream guest for 2024
(00:18:24) Discussing the most challenging conversation preparation
(00:22:32) Reflecting on the best Colossus moments in 2023
(00:25:52) Different ways to format episodes, successful episodes in 2023 and potential new formats in 2024
The Evolution of FreightWaves with Craig Fuller - [Making Media, EP.51]
Episode 51
Thursday, January 4, 2024 • Duration 01:03:59
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 market doesn't put a value on audiences.
In the second half of our conversation we get into Craig's playbook for buying up niche magazines around things like private aviation and boating. He explains why it is so important to capture the full audience base and some of the fun projects that he has been tying in around those audiences. This is a wide ranging conversation with someone who has taken a very interesting approach coming in as a practitioner, once a pilot himself, and how he's taken some of those lessons and applied them into building businesses. Please enjoy this conversation with Craig Fuller.
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
Show Notes
(00:02:38) - (First question) - Craig’s initial mindset when launching FreightWaves
(00:05:37) - Craig’s observations about fundraising when shifting the business into a media business
(00:13:08) - How he bridged the gap between his industry expertise and the media business' need for specialized knowledge
(00:17:35) - How his media business was initially funded
(00:20:46) - Disparity in market valuation with audiences undervalued and some SAS businesses overvalued
(00:26:14) - The motivation in pursuing the purchase of Flying magazine
(00:31:02) - Lessons learned from attaching real estate to audiences compared to finance or e-commerce
(00:34:15) - The strategy behind acquiring numerous media outlets
(00:37:54) - Economic principles for managing acquired magazines
(00:39:33) - The correlation between the aviation and freight industries
(00:40:46) - The importance of having an interest in an industry before acquiring an existing audience
(00:43:47) - The elements Craig tries to enhance when revamping older magazines
(00:47:39) - Shifting advertiser mentality into niche marketing and its ultimate success
(00:49:46) - The early challenges of switching to a specialized, niche audience
(00:51:08) - Whether this model works for all magazine or if niche marketing is only successful with expensive product content like planes
(00:54:58) - Debrief
A Lesson in Paid Growth with Jonathan Becker - [Making Media, EP.50]
Episode 50
Thursday, December 28, 2023 • Duration 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 guest to dig deeper.
In the conversation, we draw on parallels to investing, how Jon and Thrive approach campaigns & what metrics they're looking at, what the rules of thumb really are, and Jonathan's general philosophy on marketing as a whole. Please enjoy our conversation with Jonathan Becker.
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
Show Notes:
(00:01:50) - (First question) - Examining the link between advertising and investing
(00:05:14) - Identifying underserved segments in the market
(00:07:07) - Exploring unconventional routes to success
(00:10:32) - Determining the effectiveness of marketing strategies
(00:16:44) - Shifting strategies to business to business (B2B) marketing
(00:21:23) - Tailoring advertising budgets for smaller businesses
(00:22:46) - Evaluating the benefits of advertising on Spotify
(00:27:02) - Demonstrating advertising metrics to clients
(00:34:38) - Discussing the advantages of advertising in podcasts
(00:40:39) - Analyzing the fundamentals of creating effective advertisements
(00:43:26) - Investigating common failure points in marketing campaigns
(00:48:25) - Debrief
The North Face Presents with Kaki Orr - [Making Media, EP.49]
Episode 49
Thursday, December 21, 2023 • Duration 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 breath-taking mountains. We’ve talked a lot on this show about content to commerce but in many ways this conversation covers the reverse; commerce to content.
We talk to Kaki about creating authenticity while achieving The North Face’s goals, how these epic films come together, and how she thinks about risk throughout the process. Please enjoy this conversation with Kaki Orr.
Watch Kaki's work:
The North Face Presents: Lhotse ft. Hilaree Nelson and Jim Morrison
The North Face Presents: Earthside
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
Show Notes:
(00:01:50) - Kaki’s background before joining The North Face
(00:05:52) - Overview of her role today
(00:10:17) - Defining success
(00:11:45) - Which stories are picked
(00:14:15) - General project timelines
(00:16:03) - The logistics of their films
(00:18:24) - Budget allocation and coordination
(00:20:13) - Building teams around an athlete
(00:22:52) - Leaving room for the unexpected
(00:26:19) - Managing talent and project risk
(00:31:20) - Finding effective distribution channels
(00:36:38) - Other brands that inspire Kaki
(00:38:10) - Fundamentals of making a great documentary
(00:40:34) - What she’d like to achieve over the coming decade
(00:42:40) - Debrief
Best Books, Movies, and Podcasts of 2023 with Web Barr - [Making Media, EP.48]
Episode 48
Thursday, December 14, 2023 • Duration 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 National Geographic magazine, he was Head of Content at Meet Cute, and is currently building something new in the media industry called Hi Barr. He is one of the best curators of content we know. We each select one book or article, one film or TV show, and one non-Colossus podcast. Please enjoy this yearly media roundup with Web Barr and make sure to check out his newsletter and new podcast.
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:
(00:00:23) - First question
(00:00:33) - Discussion on Hi Barr Weekly Letter Up to 11
(00:02:02) - Web's Favorite Article of the Year
(00:03:53) - Discussion on the Art Market and Gagosian's Influence
(00:05:39) - Reflections on the New Yorker's Journalism
(00:09:31) - Dom's Book Pick of the Year
(00:11:26) - Learning from the Restaurant Business
(00:14:52) - The Wager: A Book Recommendation
(00:18:56) - Favorite Movie of the Year: Oppenheimer
(00:22:10) - TV Show Review: All the Light We Cannot See
(00:26:44) - Movie Review: The Killer
(00:30:13) - Favorite Comedy Movie Discussion
(00:30:49) - Webb's Favorite Podcast: Rick Rubin's Tetragrammaton
(00:33:05) - The Power of Rick Rubin's Podcast
(00:39:39) - Dom's Favorite Podcast: Hodinkee's Talking Watches
(00:41:06) - The Uniqueness of Hodinkee's Talking Watches
(00:47:51) - The Challenge of Growing Podcasts
(00:49:26) - Blank Check Podcast. Wrapping Up the Year's Recommendations
The Story of Stripe Press with Tamara Winter - [Making Media, EP.47]
Episode 47
Thursday, December 7, 2023 • Duration 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 synergies or reasons why a payments business would incubate a publishing arm – particularly one that focuses on publishing or re-publishing physical books. But, as Tammy explains, there is a lot more than meets the eye.
We recorded this conversation on Tuesday morning last week before the incredibly sad news that investing icon, Charlie Munger passed away. Stripe Press republished Poor Charlie’s Almanac earlier this week and we talk about that two-year project with Tammy in our discussion. Please enjoy this conversation with Tammy Winter.
Listen to Invest Like the Best: A Conversation with Charlie Munger & John Collison
Order your copy of Poor Charlie’s Almanack
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
Show Notes:
(01:59) - (First Question) - The origin story and purpose of Stripe Press
(08:07) - Choosing between tactical guide-like books and inspirational open-ended books
(15:56) - Tammy's personal story and educational background
(20:54) - Intersecting with prominent people using Twitter to advance professionally
(24:00) - How they measure success at Stripe Press
(30:43) - Measuring success without numbers
(35:00) - Why produce physical books
(36:48) - Design conception and the process behind creating the books
(40:19) - Where books like Poor Charlie’s Almanack originally come from
(45:17) - Tammy's reflections on the media industry and what she’s learned in her career
(51:24) - Debrief
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