Financial services are overdue for an overhaul. With a16z's newest general partner, Alex Rampell (who just officially started), this segment of the podcast explores the world of fintech... How software backed up by data is being brought to bear on lending, insurance, and the science (oftentimes art) of underwriting risk. We also get a taste of what life was like for Rampell running a successful internet business out of his bedroom -- an experience that would lead him toward the world of monetization/ payments and eventually co-founding numerous startups.
In this hallway-style conversation (originally recorded as a video), a16z general partner Alex Rampell and Terry Angelos, SVP of Commerce Solutions at Visa, discuss the trials and tribulations of their time as co-founders of TrialPay, an e-commerce payment and promotions platform. The story begins with their serendipitous initial meeting twelve years ago; tracks the obstacles overcome, rise, and eventual acquisition of TrialPay (by Visa in 2015); and ends with reflections on the future landscape and potential of payments. How can a third party increase profits for all parties involved? And how can a payments startup make a splash in an industry dominated by a few well-known incumbents?
Software has fundamentally changed the way we record, store, and share information. Its next act is to fundamentally change the nature of our economy, capturing trillions of dollars of value in the process. In this talk from the 2025 a16z LP Summit, a16z General Partner Alex Rampell discusses the history of filing cabinets and databases, how SaaS pricing moved from seats to outcomes, and how AI agents will accelerate the trend of the last 70 years of software progress. Timecodes: 0:00 Introduction 0:27 Historical Context: Automation and Labor 3:25 The Filing Cabinet Era: Digitizing Records 4:12 Case Studies: Software Transforming Industries 8:39 The SaaS Business Model and Its Limits 11:41 Labor Market Scale vs. Software Market 12:19 The Shift: Software Doing the Job 15:44 Case Study: Job Opening 18:11 Real-World Examples: AI in Action 21:01 The Human Element: Demoralizing Jobs & Language 22:52 Market Expansion: New Opportunities with AI 26:02 Conclusion: The Future of Software and Labor Resources: Follow Alex on X: https://x.com/arampell Stay Updated: If you enjoyed this episode, be sure to like, subscribe, and share with your friends! Find a16z on X: https://x.com/a16z Find a16z on LinkedIn: https://www.linkedin.com/company/a16z Listen to the a16z Podcast on Spotify: https://open.spotify.com/show/5bC65RDvs3oxnLyqqvkUYX Listen to the a16z Podcast on Apple Podcasts: https://podcasts.apple.com/us/podcast/a16z-podcast/id842818711 Follow our host: https://x.com/eriktorenberg Please note that the content here is for informational purposes only and should not be taken as legal, business, tax, or investment advice, nor used to evaluate any is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details, please see a16z.com/disclosures.
The a16z AI Apps team outlines how they are thinking about the AI application cycle and why they believe it represents the largest and fastest product shift in software to date. The conversation places AI in the context of prior platform waves, from PCs to cloud to mobile, and examines where adoption is already translating into real enterprise usage and revenue. They walk through three core investment themes: existing software categories becoming AI-native, new categories where software directly replaces labor, and applications built around proprietary data and closed-loop workflows. Using portfolio examples, the discussion shows how these models play out in practice and why defensibility, workflow ownership, and data moats matter more than novelty as AI applications scale. Timestamps: 00:00 - The AI Opportunity: Apps, Distribution, and Platform Shifts 02:17 - AI's Role in Enterprise and Consumer Applications 05:03 - Emerging AI Trends and Investment Strategies 08:43 - Traditional Software Going AI Native 14:40 - Software Eating Labor 17:04 - Case Study: Eve 21:33 - Building Defensible Moats 24:45 - Case Study: Salient 31:53 - The Walled Garden 40:23 - Incumbents vs. Startups 49:39 - AI Roll-ups 53:32 - Consumer AI Applications 56:03 - Model Aggregation Strategy 57:06 - Investment Process & Team 1:06:46 - Q&A: Customer Retention & Enterprise Sales Resources: Follow Alex Rampell on X: https://twitter.com/arampell Follow Jen Kha on X: https://twitter.com/jkhamehl Follow David Haber on X: https://twitter.com/dhaber Follow Anish Acharya on X: https://twitter.com/illscience Stay Updated: If you enjoyed this episode, be sure to like, subscribe, and share with your friends! Find a16z on X: https://twitter.com/a16z Find a16z on LinkedIn: https://www.linkedin.com/company/a16z Listen to the a16z Podcast on Spotify: https://open.spotify.com/show/5bC65RDvs3oxnLyqqvkUYX Listen to the a16z Podcast on Apple Podcasts: https://podcasts.apple.com/us/podcast/a16z-podcast/id842818711 Not an offer or solicitation. None of the information herein should be taken as investment advice; Some of the companies mentioned are portfolio companies of a16z. Please see https://a16z.com/disclosures/ for more information. A list of investments made by a16z is available at https://a16z.com/portfolio.
The web is unhealthy, and AI agents are about to rewrite how we shop. In this episode, a16z General Partner Alex Rampell and Partner Justine Moore explore how AI agents will change commerce and the implications for Google’s business model, affiliate marketing, online shopping, and more. Timecodes: 0:00 Introduction 0:36 Affiliate Marketing and the Evolution of Online Purchases 1:59 Impulse Buys vs. Considered Purchases 2:51 Observing Consumer Behavior and Viral Trends 6:09 Dynamic Pricing and Consumer Surplus 7:14 E-commerce vs. In-Person Shopping 10:20 The Challenge of Attribution in Online Sales 12:28 Aggregators, Brands, and the Commodity Trap 15:36 Trends, Trust, and the Power of Aggregators 17:46 Google’s Freemium Model and the Future of Search 21:17 The Problem of Hallucination in AI Product Recommendations 22:52 The Commercialization and Pollution of the Internet 29:30 The Costco Model: Trust and Value 33:20 The Spectrum of Purchases and AI’s Role 37:57 UPCs, SKUs, and Automation in Commerce 39:52 Opportunities for New Winners in AI-Driven Commerce Resources: Read the article: http://a16z.com/ai-x-commerce/ Find Alex on X: https://x.com/arampell Find Justine on X: https://x.com/venturetwins Stay Updated: If you enjoyed this episode, be sure to like, subscribe, and share with your friends! Find a16z on X: https://x.com/a16z Find a16z on LinkedIn: https://www.linkedin.com/company/a16z Listen to the a16z Podcast on Spotify: https://open.spotify.com/show/5bC65RDvs3oxnLyqqvkUYX Listen to the a16z Podcast on Apple Podcasts: https://podcasts.apple.com/us/podcast/a16z-podcast/id842818711 Follow our host: https://x.com/eriktorenberg Please note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details please see a16z.com/disclosures.