Why This PayPal Investor Refuses to Invest in AI | William Quigley

Today's guest is William Quigley, one of the few venture investors who has operated at the centre of multiple technological inflection points. William was one of the first institutional investors in PayPal, co-founded Tether, the world's first and largest fiat-backed stablecoin, and founded WAX, one of the most active NFT blockchains globally. He saw the consumer internet emerge, watched payments transform, helped shape crypto infrastructure, and now sits at the edge of the AI wave. This is our third conversation with William, and a lot has changed since we last spoke 18 months ago. This time we go beyond the cycles and into the structural future: who owns the rails, how capital actually flows, and where the durable infrastructure is forming beneath the hype. In the full episode, we cover: Why AI is the opposite of the early internet and early crypto, and why that should worry you Why the economics of today's AI companies are inverted, and how long they can really last Why he backed PayPal and built Tether but will not invest a dollar in AI How VCs boycotting semiconductors for 25 years accidentally created NVIDIA Why OpenAI and Anthropic may go public and still struggle as public companies The trillion-dollar currency conversion tax that tokenised money could erase Why NFTs are not dead, just rebranded, and where the real use cases are growing The one trait William looks for in every founder and CEO, and why he thinks you are born with it How young people should position themselves while it is still early If you are a fintech founder, an investor trying to read the AI cycle, or anyone working out where the durable opportunities are forming beneath the hype, this one is worth your time. Timestamp: 00:00 - Trailer 01:20 - Intro and welcome 03:25 - Is AI mid-90s internet, 2011 crypto, or something different 05:28 - Why this cycle is the opposite: record capital, VC concentration 06:49 - The broken economics: why AI's variable costs invert the model 09:49 - The infrastructure layer: riding on others' rails 13:12 - Why VCs boycotted semiconductors for 25 years and built NVIDIA 14:34 - Piling money into one winner: the Uber-era playbook 16:55 - $20B in 1995 vs hundreds of billions today, and the IPO problem 20:33 - Can incumbents acquire the AI giants 22:56 - Why OpenAI and Anthropic may struggle as public companies 24:38 - Does AI need blockchain as a settlement layer 29:24 - Trust, identity, and where NFTs actually went 32:50 - Stablecoins, tokenised fiat, and the trillion-dollar currency tax 36:16 - AI hype vs reality 41:24 - Where the real opportunities are forming now 49:37 - Founder and CEO traits: why good judgment is the rare one 57:15 - How young people should position themselves while it's early 59:36 - What William is building and investing in now Connect with William E. Quigley:   / williamedwardquigley   https://x.com/WilliamEQuigley?lang=en Matthew Cheung (Host & Founder Work in Fintech):   / matthewcheung50   Work in Fintech Socials: LinkedIn:   / work-in-fintech-global   X: https://x.com/WorkinFintech Instagram:   / work_in_fintech