He wrote the Dos Equis "Most Interesting Man in the World" campaign. Now he's one of the most interesting people writing verticals.

Thom Woodley has spent twenty years showing up early — to scripted web series, to interactive mobile, to branded content, and now to micro drama. In 2006, he created The Berg, one of the first scripted online sitcoms. He wrote hundreds of episodes for Episode Interactive. He ran branded content at CollegeHumor/Dropout. He was the first writer signed to the WGA's New Media Caucus.

In this episode, Thom and Pauline get into the consultancy he co-founded, Hudson Vertical (https://hudsonvertical.com/), which now sits at the intersection of apps, brands, streamers, and investors trying to figure out where this space is going. They talk about why an advertising background may be better training for vertical writing than traditional Hollywood. They unpack burnout as spiritual misalignment, not overwork. They reframe disappointment as just an appointment that didn't happen.

And then comes the sea change: Thom shares why he was wrong about AI in verticals — and what shifted in the last few months that's made him a hesitant futurist.
In this conversation:

Why being early to every new medium has been Thom's accidental specialty
What the Dos Equis campaign taught him about writing for a three-second scroll
How Hudson Vertical works with apps, brands, and investors entering the space
The honest reversal on AI: why he no longer thinks audiences won't watch (or pay) for AI-generated shows
Burnout, stoicism, and the Buddhist case against expectation
His clearest advice for anyone hesitating to take a vertical leap

Connect with Thom Woodley:
Hudson Vertical: https://hudsonvertical.com/
Whether you're considering the jump yourself or trying to understand where this industry is actually going, this is a conversation worth your full attention.