Dana Settle of Greycroft on investing through AI cycles and the sustainability opportunity

Summary

Dana Settle, co-founder and managing partner of Greycroft, has been investing since 1998 and draws direct parallels between the current AI infrastructure build-out and the first generation of internet infrastructure she funded in networking, semiconductors, and optical equipment.

Mountain: A 14-Year Overnight Success

Greycroft's most recent IPO is Mountain, a connected television advertising platform founded by Mark Douglas. Greycroft invested at the Series B in 2011 at a valuation context where the round was just $4 million. The company began as a display advertising business, generated over $100 million in revenue from that original model, then pivoted entirely to connected TV as cookie-based targeting faced regulatory pressure. Douglas self-funded the new business from cash flow, sunset the legacy operation, and took the company public approximately two weeks before this recording.

The pivot thesis has been validated by streaming platform earnings. Netflix, Disney, and others now see the majority of new subscribers joining ad-supported tiers, a structural shift that was far from consensus when Mountain repositioned.

Ryan Reynolds and his marketing agency became strategic partners at Mountain, with Settle making the connection while Reynolds was evaluating what to do with the agency. The partnership was operationally significant rather than cosmetic. Mountain's inbound sales leads rose from roughly 2% to over 60% following the partnership, driven in part by Reynolds directly reaching out to CEOs in a B2B sales capacity.

Sustainability as an AI Adjacency

Greycroft runs a dedicated sustainability fund structured as a partnership with Coca-Cola and eight of its largest global bottlers. Settle frames sustainability as directly intersecting with AI rather than sitting apart from it. With global energy consumption projected to double by 2050, she sees opportunity not just in renewables but in the software and hardware layer that reimagines how energy is consumed across data center and enterprise infrastructure.

Geographic Positioning

Settle acknowledges AI talent density is pulling activity back toward the Bay Area, describing it plainly as a "sucking sound." Greycroft opened its first San Francisco office last year and hired a new partner there. Settle spent 10 years in Silicon Valley before relocating to Los Angeles nearly 20 years ago and remains constructive on LA, pointing to Greycroft's investment in Whatnot, which she describes as the largest live-streaming shopping platform in the United States, as evidence the market continues to produce consequential companies.

Advice on Celebrity Capital

On celebrity involvement in venture, Settle draws a clean distinction between passive and active participation. For those seeking general exposure, LP positions in funds are the appropriate vehicle. Direct or angel investing only makes sense where the individual brings genuine, differentiated value to the company. She cites Reynolds at Mountain and Gwyneth Paltrow at Goop and Goop Kitchen as examples where the involvement is authentic to the person's expertise and brand, which is what drives real business impact.