Elaine Dai is a Partner at Alt Capital, a new venture firm founded by Jack Altman that backs ambitious founders in AI and enterprise software. In this episode, we dive into Elaine’s journey from Harvard to Microsoft, Norwest, and now Alt, where she helps lead a $275M second fund focused on AI-native companies and category-defining startups.

Elaine shares what it takes to recognize outlier founders, how she evaluates “slope over snapshot,” and why the best VCs act as invited guests rather than helicopter investors. She also reflects on risk-taking, the immigrant mindset, and why being in San Francisco compounds serendipity.

We also cover:

• Why “AI-native” beats “AI-wrapper” startups

• How to find (and stress-test) the right co-founder

• Practical advice for breaking into VC without a traditional background

• The hardest parts of conviction, patience, and playing the long game