A practical tour of sports media, platform strategy, and the business behind personality-led shows.
Making Media uses Mike Strickhoff's career to show how personality-driven sports media gets built, then rebuilt, as platforms shift around it.

Colossus | Investing & Business Podcasts
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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.
Based on 6 episodes we listened to · September 2026
Making Media turns conversations with media operators into concrete lessons about audience ownership, distribution, monetization, and disciplined growth.
Making Media follows the money and operating choices behind media companies, with Matt Reustle and Dom Cooke pressing guests on how audiences become durable businesses.
Hulk's rights problem is fair game here, if your media curiosity follows the money.
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Short reviews from the PlayNext desk, based on the episodes we processed.
A practical tour of sports media, platform strategy, and the business behind personality-led shows.
Making Media uses Mike Strickhoff's career to show how personality-driven sports media gets built, then rebuilt, as platforms shift around it.
A sharp look at how a niche sports writer keeps a durable voice.
Kyle Porter’s path through golf media reads less like a tidy career arc and more like a voice finding a place to live. The best part of the conversation is how it ties his CBS work, newsletter, and books to a simple problem: how to stay close to the work you care about without…
A grounded look at how a focused aviation publisher turns specialization into a subscription business.
John Ostrower lays out a tight case for The Air Current: a subscription business built on narrow aviation coverage, with a reader-first model and a small team of four to five people.
A clear look at paid growth as capital allocation, not just ad spend.
Jonathan Becker frames paid growth as a question of capital allocation, and that angle suits the discussion. He and the hosts lean on Thrive Digital's scale, including more than $3.5 billion in deployed paid acquisition budgets, to keep the focus on investment, measurement, and…
A roundup that turns curation into the main point.
Making Media treats a roundup as an argument for curation itself. Webb Barr joins the hosts as they revisit High Bar Media picks and resurfaced interviews, and the conversation keeps returning to what makes a work last: a sharp interview, a memorable scene, a recommendation that…
A clear look at how Every keeps evolving as a media business.
This episode uses Dan Shipper and Every to show how a media company can keep changing without losing its core. It follows Every's move from a pandemic-era bundle of business newsletters by different authors to a daily essay newsletter on technology, productivity, and AI, with…
A clear look at how AD balances heritage, format, and audience reach.
The piece treats Architectural Digest as a century old brand that has to keep its history intact while still moving with design culture. Amy Astley makes that tension feel concrete, especially when the conversation moves from the magazine to video, social platforms, and then…
A Stripe Press conversation about mission, editorial taste, and how carefully made books get produced.
Tammy Winter, Stripe Press's commissioning editor, anchors a conversation about why a payments company would back a publishing house built around physical books and big ideas.

Rob Walling on bootstrapped SaaS growth, plateaus, and exits — with founders who lived them.

Abbey Ashley's playbook for turning your job skills into a virtual assistant business.

Naval Ravikant on epistemology, startups, and crypto, from David Deutsch to Vitalik Buterin.

Alex Theuma interviews SaaS founders and investors on scaling to $10M-plus ARR.

Guy Raz traces founders' origin stories and fields live advice-line calls from entrepreneurs.

Alex Blumberg interviews guests like Megan Phelps-Roper and Shane McAnally about failure and reinvention.
Jonathan Becker, founder of Thrive Digital, says his team has deployed more than $3.5 billion in paid acquisition budgets and uses the same logic as value investing when buying media.
Jack Davenport says Goalhanger Podcasts now reaches about 30 million downloads a month across The Rest Is History, The Rest Is Politics, The Rest Is Football, The Rest Is Money, and The Rest Is Entertainment.
Mike Strickhoff maps sports media from the inside.
Spike Eskin, head of programming at New York's WFAN and host of The Rights to Ricky Sanchez, assigns 60% of an ideal sports host to fearless opinions and the ability to withstand being wrong.
Emily Sundberg joins Making Media and is asked how she describes herself.
Ben Springwater, founder of Matter, says he and co-founder Rob were Pocket users at Nextdoor who started from frustration with stitching together reading tools.
Making Media's 2023 recap opens with a macro read on podcasting: December downloads for the top 20 publishers were down 24% year over year, ad rates fell from $25 CPM to about $22, and new RSS feeds hit a five-year low at just over 200,000.
Kyle Porter, a CBS sports writer who has covered golf since 2012, says he has grown tired of professional golf because of the PGA Tour-LIV conflict while feeling more connected than ever to playing the game himself.
Jon Ostrower describes building The Air Current as a subscription publication for aviation and aerospace, with a strict paywall, glossy PDF products, and direct email and push-notification distribution.
Craig Fuller discusses how FreightWaves evolved from a commodity futures market concept into a media and data business.
Matthew Sherry, CEO of Platform Media, discusses how he built a unique podcast business by solving distribution and monetization challenges.
Peter Kafka discusses how media business models continuously reinvent themselves.
Dan Shipper, CEO of Every (pandemic-era business newsletter bundle), discusses the evolution of his company and personal identity as both founder and writer.
Dom Cooke shares seven key lessons from a year of running a media business, emphasizing listener-centricity, the slow-growth nature of media, simplicity in production, the critical role of newsletters, challenges with subscriptions, team communication, and long-term consistency.
Amy Astley describes how she took Architectural Digest from a mostly print magazine into a multimedia brand while still treating the magazine as the center of the business.
Tammy Winter, Stripe Press’s commissioning editor, explains why a payments company built a publishing arm with fewer than 10 full-time staff.
Joanna Robinson discusses her definitive book on Marvel's history, tracing the MCU from pre-Disney days to its recent perceived decline.
Kaki Orr from The North Face discusses how major brands approach authentic storytelling, media production, and the challenges of maintaining creative integrity within commercial constraints.
Webb Barr recommends Patrick Radden Keefe’s New Yorker profile on Larry Gagosian, describing it as a long-form biography that moves from William Morris poster sales in Los Angeles to an art-world empire.
Making Media marks Tim Ferriss's 10th podcast anniversary and billion-download milestone with a conversation about how he approaches interviewing.
Adam Hansmann says The Athletic launched in 2016, when paid content was still a contrarian idea and local sports coverage was shrinking in places like Chicago.