Episode Details

(0:00) Intro, *Reference to the Boardroom Governance Summit (Aug 26-27, 2026) 

(2:42) About the podcast sponsor: The American College of Governance Counsel.

(3:28) Start of interview. *Reference to prior episode with Greg (E136) from 2024.

(5:14) Market Boom and AI Supercycle

(6:14) AI Is Changing Everything

(9:06) How does a VC use AI (venture business: sourcing, selection, and stewardship)

(12:13) Cloud and Startup Costs, rise of seed rounds and institutional angel investors

(15:13) JSV Launchpad, a 10-week, in-person summer program in SF from JSV for early-stage student AI founders 

(18:50) SaaSpocalypse Debate and AI Washing (reference to the Albert Saniger / Nate Inc case)

(21:33) Growth Metrics Rewritten (when Anthropic has grown 80x year over year) "the best solution for high prices is high prices"

(24:20) Sorting SaaS Risks

(27:30) Defensibility in the AI Era: 1) Network effects, 2) Systems of record, and 3) Regulated workflow.

(29:52) AI impact to companies: 1) Are the foundation models existential? 2) How much have you incorporated AI into your platform or your product? 3) How important is AI within your product? and 4) How much have you integrated AI into your operations? "In a world where building software is easy, one of the things that we're already seeing within our portfolio, and I think we'll see more of this, is... horizontal expansion (expanding to adjacent businesses)."

(32:33) AI, Jobs, and Layoffs (*reference to this FT article: What if remote working, not AI, is to blame for weak junior hiring?)

(38:28) Private Markets and IPOs. Liquidity in venture ecosystem (M&A and private equity).

(42:02) SpaceX, Anthropic and OpenAI IPOs

(45:18) Data Centers and Backlash "It's easy to demonize"

(46:16) Regulation and Global Competition "AI right now has become a great bogeyman for both sides."

(50:14) Board Strategy for AI

(52:12) On Kirkland & Ellis' $500m bet to develop its own AI technology

Greg Gretsch is a Founding Partner and Managing Director of Jackson Square Ventures, an early-stage VC firm based in San Francisco. Greg has more than two decades of experience in VC and five of his early-stage investments have gone on to exits or valuations above $1 billion.

You can follow Evan on social media at:

X: @evanepstein

LinkedIn: https://www.linkedin.com/in/epsteinevan/ 

Substack: https://evanepstein.substack.com/

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