Summary:

Doug Weaver is one of the true architects of modern digital media sales. He sold web sponsorships in the earliest days of HotWired, helped shape the industry’s foundational years, and spent nearly three decades as Founder & CEO of Upstream Group advising 900+ media and technology companies (from Wired and Hulu to Spotify, Facebook, BuzzFeed, and The New York Times) while training thousands of sellers and leaders (including Ray).

In this episode, Doug breaks down what’s actually changed (and what hasn’t) in a world of consolidation, why most sellers plateau when they start making real money, and the most common mistakes he’s seen over decades, both for reps and managers. We go deep on relationship diversification, selling “left of budget,” coaching the process (not solving the problem), and why values and ethics matter more than ever as the stack evolves.

We close with Doug’s next chapter: the Weaver Collective...his curated coaching community designed to develop the next generation of sales leaders.

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Chapter Timeline:

1. 00:00 Teaser Open
2. 00:25 Doug’s intro: Wired, Upstream Group, The Drift, Weaver Collective
3. 02:03 Print-era lessons: scrappiness, creativity, “village of lost toys” accounts
4. 02:38 HotWired and the early web: what really happened in 1994
5. 05:01 Young Doug: wanting to be a teacher & the mentor who shaped him
6. 06:34 What we’ve “lost” (and haven’t): consolidation then vs. now
7. 09:01 The Upstream origin story: how training happened by accident
8. 14:21 The #1 seller mistake: relationship diversification & proactive demand creation
9. 18:01 The #1 leader mistake: solving problems vs. coaching the process
10. 40:29 The next chapter: Weaver Collective, community coaching, and what to protect in the profession

Keywords:

Doug Weaver, Upstream Group, Weaver Collective, digital advertising, media sales, ad tech, CRO, revenue leadership, sales management, sales training, account strategy, consultative selling, demand creation, agency relationships, consolidation, IAB, HotWired, Wired, leadership coaching, mentorship, ethics in advertising, sales process

Guest Bio (Doug Weaver):

Doug Weaver is one of the architects of modern digital media sales. He spent nearly three decades as Founder & CEO of Upstream Group, advising 900+ media and technology companies including Wired, Spotify, Hulu, Facebook, BuzzFeed, Vevo, and The New York Times. Doug authored The Drift for more than 20 years, helped shape the foundational years of the industry, and trained thousands of sellers and leaders across media and ad tech. Today, he coaches senior leaders through the Weaver Collective at weavercollective.net.

Host Bio (Ray Erickson):

Ray Erickson is the creator & host of The Seat and a revenue leader across media, ad tech, and streaming. He’s held leadership roles at Samsung Ads, Conversant/Epsilon, and Katz Media, and is the founder of Axis Advisory, LLC. On The Seat, Ray sits down one-on-one with revenue leaders to unpack the early days, mentors, setbacks, and moments that shape how executives lead.

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