

The Community Exchange Podcast by OpenWeb
OpenWeb
This is The Community Exchange Podcast, brought to you by OpenWeb: an interview podcast series featuring the leaders building the media ecosystem of the future.
This season, our host is industry veteran Matthew Scott Goldstein (a.k.a. MSG). Each episode he explores our guests’ journeys through the media world, the work they are currently doing, and how they’re shaping the media and publishing industry.
Learn more about OpenWeb at http://www.openweb.com
This season, our host is industry veteran Matthew Scott Goldstein (a.k.a. MSG). Each episode he explores our guests’ journeys through the media world, the work they are currently doing, and how they’re shaping the media and publishing industry.
Learn more about OpenWeb at http://www.openweb.com
Episodes
Mentioned books

Jul 23, 2025 • 1min
Season 3 Trailer
This is The Community Exchange Podcast, brought to you by OpenWeb: an interview podcast series featuring the leaders building the media ecosystem of the future.This season, our host is industry veteran Matthew Scott Goldstein (a.k.a. MSG). Each episode, he explores our guests’ journeys through the media world, the work they are currently doing, and how they’re shaping the media and publishing industry.Learn more about OpenWeb at http://www.openweb.com

10 snips
Mar 18, 2025 • 43min
Unlocking New Revenue Streams with Condé Nast's Jennifer Salant
Jennifer Salant, VP of Global Partnerships & Business Development at Condé Nast, shares her journey through the media landscape. She discusses the evolution of digital media from blogs to influencer content and how Condé Nast has navigated YouTube and FAST channels. The conversation covers the challenges and opportunities AI presents for publishing, innovative content strategies, and the importance of audience engagement. Salant also emphasizes the need for publishers to adapt and future-proof their strategies in a rapidly changing media environment.

9 snips
Mar 11, 2025 • 58min
Detangling the Advertising Web with Adweek’s Will Lee
In this discussion, Will Lee, CEO of Adweek and former finance executive, shares insights from his journey into media leadership. He discusses the digital transformation of journalism and how AI is reshaping advertising strategies. Will highlights the importance of first-party data for audience engagement and reflects on the evolving dynamics between agencies and marketers. He also recalls nostalgic moments from the 1980s advertising scene, emphasizing the lasting impact of iconic ads and the shift towards data-driven decision-making in modern media.

Mar 4, 2025 • 45min
Ad Analytics by the Second with Yahoo’s Gabriel DeWitt
In this episode of The Community Exchange Podcast, we welcome Gabriel DeWitt, Head of Monetization at Yahoo.In our discussion, MSG and Gabriel cover: Gabriel’s journey from software engineering to ad tech leadership Digital advertising's evolution from direct sales to programmatic Header bidding's rise and its impact on the open internet Challenges of monetization, privacy regulations, and the cookie collapse The ongoing battle between the open internet and walled gardens Yahoo's role in shaping the future of digital advertising The impact of AI and automation on ad tech and monetization strategies How publishers can adapt to a post-cookie world The future of identity and targeting in a privacy-first landscapeAnd more.New episodes of The Community Exchange Podcast are released each week. Subscribe wherever you listen to podcasts to get the latest right in your feed.

Feb 25, 2025 • 53min
Dissecting Publishers' Data with Mike O’Sullivan
On this episode of The Community Exchange Podcast, we welcome Mike O'Sullivan, Co-Founder and CEO at Sincera. In our discussion MSG and Mike cover: Mike O’Sullivan’s journey from Microsoft to founding Sincera The evolution of programmatic advertising and ad tech Challenges in reporting, transparency, and data management Google’s antitrust cases and its impact on the ad tech ecosystem Unlocking hidden revenue and optimizing publisher monetization The role of first-party data in ad sales and strategy Gaining control over the publisher tech stack and supply chain The future of publishing: mixed media and investing in editorial talentAnd more.New episodes of The Community Exchange Podcast are released each week. Subscribe wherever you listen to podcasts to get the latest right in your feed.

8 snips
Feb 18, 2025 • 39min
Saving Publishing with Daily Mail's Rich Caccappolo
Rich Caccappolo, Vice Chair at Daily Mail General Trust, shares his remarkable journey from CTO at iVillage to a top leader in media. He dives into the critical shift towards curated audiences amidst post-cookie challenges and the importance of adapting to AI's influence on content creation. Caccappolo also discusses the transformation of the Daily Mail from print to a digital powerhouse, emphasizing the need for collaboration and audience engagement strategies across platforms like TikTok. This insightful conversation reveals opportunities for publishers within a rapidly evolving media landscape.

8 snips
Feb 12, 2025 • 50min
Publishing in 2030 with Dotdash Meredith’s Dr. Jonathan Roberts
Dr. Jonathan Roberts, Chief Innovation Officer at Dotdash Meredith, shares his fascinating journey from physicist to publishing innovator, even serving as the official cartographer for Game of Thrones. He discusses transforming legacy brands like About.com for the digital era and emphasizes the importance of community engagement in publishing's future. Jonathan reveals how audience data is reshaping content strategies and the evolving role of AI in personalizing experiences. He also dives into revenue strategies in a privacy-conscious ecosystem, targeting younger, digital-native audiences.

9 snips
Feb 4, 2025 • 34min
The Birth of Digital Advertising with Advertising.com OG David Jacobs
In this fascinating discussion, David Jacobs, CEO of Contxtful and a pioneer in digital advertising, shares his journey from the early days at Advertising.com to current challenges in ad tech. He analyzes the potential breakup of Google and its consequences for publishers, alongside the shift towards e-commerce ads amidst a decline in search traffic. David also weighs in on the role of AI in targeting and the future of digital revenue models. With insights on the evolving landscape, he highlights the need for innovative strategies in a cookie-less world.

9 snips
Jan 28, 2025 • 38min
An Editor’s Perspective on Adtech with Jeremy Kaplan
In this enlightening chat, Jeremy Kaplan, Content Director at Future PLC, shares his journey from tech enthusiast to editorial leader. He discusses the growing significance of niche media and the challenges AI poses to original content. Kaplan critiques content aggregation platforms and highlights the evolving publishing landscape under Google's influence. Personal anecdotes about cooking and his ambitions in writing historical fiction add a relatable touch, showcasing how to merge passions for a unique career path.

11 snips
Nov 12, 2024 • 44min
Building Publisher Alliances with David Rowley
David Rowley, VP of Revenue Technology at News Corp, shares his fascinating journey from artist to media executive. He delves into the crucial need for publisher alignment in today's ad tech landscape, addressing challenges posed by tech giants. Rowley emphasizes the interdependence of journalism and advertising, discusses the emergence of new ad servers, and highlights strategies for building strong ad ops teams. His insights are a must-listen for anyone navigating the evolving digital publishing world.