AI's Survival of the Fittest

AI's Survival of the Fittest

From SHIFT by Jennifer Strong

May 20, 2026 · 20 min · Season 3 · Episode 33

About this episode

This episode discusses the evolution of AI investing and what it takes to succeed in a competitive market.

The spray-and-pray approach to AI investing is dead. Join us as we discuss what it takes to stand out in a saturated market as we move beyond the hype to identify real moats and what’s next for investors in this space. This episode was taped before a live audience at Web Summit Vancouver. We meet: Andy McLoughlin is a seed-stage investor at Uncork Capital focused on B2B software, developer tools, and applied AI — and before VC, he co-founded Huddle, an enterprise collaboration platform that was acquired in 2016. George Mathew is a self-described "deep operator turned venture capitalist" at Insight Partners, with 20+ years building companies including as CEO of Kespry and President & COO of Alteryx, which he scaled through its IPO. Emily Fontaine leads IBM's $500 million Enterprise AI fund and quantum investing strategy — she's spent 15 years at IBM, previously serving as Executive Advocate to IBM's Chairman and CEO, and as AI Federal Leader for IBM Consulting. Credits: This episode of SHIFT was produced by Jennifer Strong with help from Emma Cillekens. It was mixed by Garret Lang, with original music from him and Jacob Gorski. Art by Meg Marco.

People in this episode

Host: Jennifer Strong

Guests: Andy McLoughlin, George Mathew, Emily Fontaine

Topics covered

  • AI investing
  • venture capital
  • market saturation
  • B2B software
  • applied AI
  • investment strategies

Keywords

  • AI
  • investing
  • venture capital
  • B2B
  • software
  • market trends
  • Web Summit

Mentioned in this episode

Organizations: Uncork Capital, Insight Partners, IBM

Places: Web Summit Vancouver

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