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AI's Quiet Earthquake on VC Strategy | Anne Dwane
If you’re trying to predict the next unicorn by pattern-matching the last one, you’re probably already behind. In this episode, Anne Dwane of Village Global explains why predicting startup outliers has never been more difficult, how AI is quietly reshaping venture capital strategy, and why diversified 100-company seed portfolios may outperform concentrated conviction bets.
Drawing on her journey from founding Military.com through the dot-com crash to serving as Chief Business Officer at Chegg and now General Partner at Village Global, Anne breaks down the logic behind broad portfolio construction, scout-driven deal flow, disciplined entry valuations, and why capital efficiency often beats mega rounds.
Inside the episode:
* Why every startup journey is “like driving a Humvee across the desert” and what the dot-com crash taught about durable business models
* Why the next trillion-dollar company probably won’t look like the last one
* How Village Global builds a diversified seed portfolio of ~100 companies using 30+ operator scouts
* What “narrative engineering” means and why storytelling now differentiates founders
* Why private markets can “hide sins” but public markets expose weak fundamentals
* How agentic tools, usage-based APIs, and collapsing transaction costs are reshaping the theory of the firm
* Why leadership now matters more than management in an AI-driven world
Watch full episode on YouTube:
About Anne Dwane:
Anne Dwane is a venture capitalist and former tech founder, venture-backed CEO, and public company executive with over 20 years of experience scaling companies from startup through IPO. She has managed full P&Ls, built high-performance teams, and developed products and services used by tens of millions of customers. Anne led two companies to successful acquisitions by Monster and Chegg, identified and integrated more than six acquisitions, and held P&L responsibility before and after Chegg’s IPO, when the company reached a valuation exceeding $1B.
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit postmoneypodcast.substack.com
View all episodes
By In-depth conversations with top founders and VCs on building, scaling, and raising capital across industries.If you’re trying to predict the next unicorn by pattern-matching the last one, you’re probably already behind. In this episode, Anne Dwane of Village Global explains why predicting startup outliers has never been more difficult, how AI is quietly reshaping venture capital strategy, and why diversified 100-company seed portfolios may outperform concentrated conviction bets.
Drawing on her journey from founding Military.com through the dot-com crash to serving as Chief Business Officer at Chegg and now General Partner at Village Global, Anne breaks down the logic behind broad portfolio construction, scout-driven deal flow, disciplined entry valuations, and why capital efficiency often beats mega rounds.
Inside the episode:
* Why every startup journey is “like driving a Humvee across the desert” and what the dot-com crash taught about durable business models
* Why the next trillion-dollar company probably won’t look like the last one
* How Village Global builds a diversified seed portfolio of ~100 companies using 30+ operator scouts
* What “narrative engineering” means and why storytelling now differentiates founders
* Why private markets can “hide sins” but public markets expose weak fundamentals
* How agentic tools, usage-based APIs, and collapsing transaction costs are reshaping the theory of the firm
* Why leadership now matters more than management in an AI-driven world
Watch full episode on YouTube:
About Anne Dwane:
Anne Dwane is a venture capitalist and former tech founder, venture-backed CEO, and public company executive with over 20 years of experience scaling companies from startup through IPO. She has managed full P&Ls, built high-performance teams, and developed products and services used by tens of millions of customers. Anne led two companies to successful acquisitions by Monster and Chegg, identified and integrated more than six acquisitions, and held P&L responsibility before and after Chegg’s IPO, when the company reached a valuation exceeding $1B.
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit postmoneypodcast.substack.com