Retailgentic: Agentic Commerce meets Retail and Brands

AI Shopping Agents & the Future of Commerce | Alex Rampell, Andreessen Horowitz

Aug 26, 2025
In this engaging discussion, Alex Rampell, a General Partner at Andreessen Horowitz and co-founder of Affirm, dives into the transformative impact of AI on commerce. He explores how AI agents might take over online shopping traffic and discusses the potential downfall of Google's business model. Alex shares key insights from his journey with TrialPay and affiliate marketing, and highlights the role of optimization in AI shopping. He even speculates on whether ChatGPT could evolve into a checkout platform, reshaping the retail landscape.
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ANECDOTE

From Shareware To TrialPay Success

  • Alex Rampell built TrialPay by monetizing affiliate-style offers to make people pay for shareware and software.
  • TrialPay grew into a venture-backed company and later sold to Visa after driving millions in revenue for clients like WinZip.
ANECDOTE

TrialPay Leads To Affirm And VC Career

  • Rampell co-founded Affirm after earlier attempts to work with Max Levchin as a TrialPay prospect.
  • He then joined Andreessen Horowitz and shifted his part-time investing work into a full-time role around 2015.
INSIGHT

Infrastructure vs Application Value

  • Rampell frames markets as infrastructure versus application layers to explain where value accrues.
  • He argues startups must secure distribution quickly unless they 'split the atom' with unique technology.
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