
The Rise of the Creator Entrepreneur
The Podcast Advertising Playbook with Heather Osgood

October 7, 2026 · 50 min
What happens when a podcast becomes bigger than the podcast itself? Heather Osgood sits down with Christiana Brenton, Chief Business Officer at Steven.com, to explore the rise of the “creator entrepreneur” and what it means for the future of podcast advertising. Christiana breaks down the FlightStor…
Episode guest
Christiana Brenton
Chief Business Officer at Steven
What happens when a podcast becomes bigger than the podcast itself?
Heather Osgood sits down with Christiana Brenton, Chief Business Officer at Steven.com, to explore the rise of the “creator entrepreneur” and what it means for the future of podcast advertising. Christiana breaks down the FlightStory ecosystem, why ownership and control of monetization matter, and how her team approaches selling creators across audio, video, social and beyond.
They also dig into what traditional podcast monetization models may be getting wrong, how advertisers should think about creator-led media, and whether, three to five years from now, we’ll still be buying “podcast ads” at all.
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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