The podcast discusses seven interesting topics, including prioritizing listeners in podcasting, the importance of slow growth in media, the misalignment of funding models and business sustainability, the power of starting simple in content creation, the underestimated value of newsletters, building a unique subscription service, the role of internal communication, and the passion and dedication required for podcasting.

Bryan Curtis, Editor-at-Large at The Ringer, discusses a range of media topics including writing versus podcasting, streaming versus linear, and the future of sports media. They also talk about The Ringer's independence within Spotify and the risks of cable channels transitioning to streaming. The conversation is entertaining and insightful, covering self-consciousness, chemistry between hosts, and the importance of preparation and rehearsal in podcasting.

Lenny Rachitsky, founder of 'Lenny's Newsletter,' discusses his journey and strategy behind his successful products. Topics covered include tackling challenges through research, managing the content pipeline, building a personal brand, measuring content quality, the importance of positioning, and building a team.

The podcast discusses the successful launch of the 'Art of Investing' podcast, the importance of multitasking in a small team, transparency in podcast creation, capturing a younger demographic, launching with passion and preparation, and reflections on a successful podcast launch.

Jacob Donnelly, founder at A Media Operator and publisher from the Morning Brew, talks about events in the media industry, the future of virtual events, the importance of investment in businesses, the impact of exclusive partnerships, the trajectory of creators and influencers in the media industry, and successful media companies.

In this podcast, Matt shares 7 nuggets of media wisdom including understanding the target audience, using content creation to meet interesting people, the shift from brands to individuals, a case study in the gardening industry, and the choice between building or buying a business.

David Coggins, a writer known for his creative identity, discusses his writing process, his parents' influence, and his recent assignment in Cuba. He also talks about the importance of editor-writer relationships, the impact of reflection and perspective, and his writing rituals. The podcast explores the experience of being edited by a family member and offers a recommendation for creatives.

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 journey and business with Thomas, who started it as a side venture and now has far grander plans for it. Enjoy!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(00:02:00) - (First question) - Thomas’ experience with content creation prior to starting The Dink(00:03:49) - How the first ever newsletter looked and its contents(00:04:59) - When the Dink started creating new content as well as curating existing news(00:06:20) - The point when The Dink started breaking news stories(00:07:21) - Family connections with Fromuth and the inception of Fromuth Pickleball (00:09:49) - The reason why The Dink and Fromuth needed to separate their businesses(00:11:01) - How The Dink made its first big steps as an industry leader in Pickleball news(00:12:32) - How The Dink separated themselves from competitors(00:13:11) - Thomas’ influences from other sports when creating content for The Dink(00:14:00) - The evolution of the frequency of the newsletter(00:14:52) - A breakdown of The Dink’s audience (00:15:57) - Profiling the avid Pickleball fan(00:16:48) - The timeline from getting started as a side hustle to Thomas making the leap into working on The Dink full time(00:19:00) - Thomas’ strategy for the business moving forward(00:23:13) - The Dink’s plan for content, diversification into other sports or delving deeper into Pickleball  (00:25:59) - How Thomas plans to become more independent and less reliant on Pickleball’s economy(00:27:05) - Harnessing media to grow Major League Pickleball and The Dink’s relationship with the league(00:29:12) - What Thomas has learned about the value of each of The Dink’s media outlets(00:31:26) - Bundling for cross media advertising(00:33:08) - The influence of celebrities involvement in Pickleball(00:35:48) - The challenge of bringing supply and demand together as Pickleball grows(00:36:59) - The differences between Platform Tennis, Padel and Pickleball(00:38:26) - Where Thomas would like to strengthen his team with investment(00:40:26) - Thomas’ opinion on the biggest opportunity within the Pickleball ecosystem right now(00:43:03) - The sport that Thomas would choose were The Dink to create another newsletter(00:45:24) - Debrief

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 get into Brian's own experience launching his business and unpack his view that we're in a "more with less" era in media.Please enjoy this conversation with Brian Morrissey.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(00:03:23) - (First question) - How media is adapting to the "more with less" era amidst challenges(00:06:08) - Efficiency's impact on media brand identity and content quality(00:08:21) - The benefits of niche focus in media for building sustainable brands(00:10:25) - Media companies' failure to adapt and the impact of misaligned incentives(00:13:30) - The power law effect on media business size and advocating for lean operations(00:16:22) - Starting narrowly versus broadly in the media business(00:18:57) - Leaving Digiday to build a personal, autonomous, trust-based media brand in The Rebooting(00:22:27) - Using his year away from work to strategize personal media product creation(00:23:52) - Leveraging connections to sell ads, avoiding paywall to grow faster(00:28:12) - Understanding the essence of sales and the role belief plays in it(00:30:41) - How niche markets and personal connections can serve as media business moats(00:33:43) - Valuing passion and expertise over market trends when starting a media business(00:36:53) - Why questioning industry norms can be beneficial(00:37:52) - Creators using autonomy and audiences for better deals(00:40:57) - Pat McAfee's leverage as an entity, not just talent(00:42:56) - Analyzing the Barstool-Penn breakup and its implications for the media business(00:46:27) - Why ad agencies continue to survive despite being dysfunctional(00:50:23) - Debrief(01:01:17) - Live Event

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 at Wachtell Lipton, and then his banking career at Goldman Sachs have played a role in his success, and we cover a ton of topics in terms of what's going on in the markets today - the overall regulatory structure and some very abstract questions. Please enjoy this conversation with Matt Levine.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 (00:01:51) - (First question) - Today's regulatory efficiency versus history  (00:07:26) - The area of finance he would like to investigate the most  (00:09:39) - The access he has to both public and private finance for his articles(00:10:21) - His relationship with his readers(00:11:08) - Responses from the individuals he writes his columns about (00:12:24) - Legalization of unregulated activities making for the most interesting articles (00:14:31) - His reason for defending finance and banks(00:17:19) - His view on whether derivatives around financial securities are a net positive (00:18:22) - His view on himself and how he would categories what he does (00:19:16) - What it’s like being an opinion writer for Bloomberg(00:21:35) - His view on large companies owning individual writers IP’s (00:25:24) - Twitter's relevance in today's society and its continued impact on social culture  (00:26:39) - Replacements for Twitter and where journalists look for interesting writing topics (00:27:28) - Topics he feels trapped into writing about due to their popularity(00:30:27) - His knowledge of special purpose acquisition companies or SPACs(00:31:52) - His perspective on the fallout from SPACs  (00:35:34) - His process on researching topics he finds most interesting to write about (00:37:00) - Strategies he uses to choose topics he wants to write about  (00:37:51) - The moment he knew readers were interested in his opinions  (00:39:25) - Analytics and the importance of how his columns perform  (00:41:03) - Performance reviews he receives from Bloomberg (00:42:02) - How writing columns has detached him from his previous financial careers(00:43:24) - His future in writing and whether he plans to change or expand his endeavors (00:44:56) - Harnessing the power of his readers and expanding his reach with media (00:46:33) - The transition from traditional media career paths to creator-led career paths   (00:50:28) - Debrief