Friday, October 10, 2025

OpenAI COO Brad Lightcap on what history teaches us about AI and the enterprise race

While OpenAI focused on the future during its DevDay event this week, I was especially curious about what OpenAI COO Brad Lightcap had to say about the past.

Lightcap—who joined OpenAI from Y Combinator in 2018—double-majored in economics and history in college. I’m a big believer that we all, deep down, remain who we were and that, to understand moments of massive change, looking back is a helpful way to look forward. When I interviewed Lightcap for the Term Sheet Podcast and asked him what history could tell us about AI today, his answer surprised me.

“There are some things that rhyme [with previous technological cycles],” he said. “But in many ways, also, AI is weird…The reason I say that is because, if you look at past technological cycles, there’s almost always been one kind of innovation, right? Sometimes people call it the J-curve.”

This is a paradigm, he said, that academic Carlota Perez talks about in her book, Technological Revolutions and Financial Capital: The Dynamics of Bubbles and Golden Ages. (He says it’s good, for anyone looking for reading material.)

“Her point, basically, is that these [transformations] have actually played out very consistently, and that you can understand these things as a repeatable phenomenon,” Lightcap said. “AI is different because the substrate is in a constant state of evolution. So, if you think about this as a road map from where we are to something akin to general intelligence, superintelligence, or whatever you want to call it—the path is exponential but it’s also ongoing.”

This rapid rate of change, he told Fortune, makes it a great time for startups.

“When the game board is getting shaken up like that, every day there’s opportunity,” said Lightcap, who also leads the OpenAI Startup Fund. “Anyone that can figure out how to really live in that disruption, live right at that frontier, and really just continue to move with the cresting wave as this continues—I think you’re in a great place.”

This ultimately aligns with Lightcap’s take on the enterprise AI race. Like any sector of tech, there’s pressure to innovate, of course. But when it comes to AI and the enterprise, Lightcap says, everything is still new and evolving in real time.

“These transformations don’t happen overnight,” Lightcap said. “Enterprises are gigantic, complex organisms. When we think about how we progress our research roadmap, we actually think along the lines of AI that’s capable of impacting a large organization. We’re not there yet. We’re still in this era where you’re just starting to have models that can use tools, take actions. They know how to intelligently solve problems and can correct their own problem-solving, in some sense. But there’s still a lot that has to get built.”

Reflecting on how early it is in the enterprise AI story (but also in a statement that perhaps applies to AI overall), Lightcap put it simply: “We’re four seconds in this entire shift.”

See you Monday,

Allie Garfinkle
X: @agarfinks
Email: alexandra.garfinkle@fortune.com
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Venture Deals

- Reflection, a Brooklyn, N.Y.-based open-source superintelligence lab, raised $2 billion in Series B funding from Nvidia, Disruptive, B Capital, Citi, and others.

- Expedition Therapeutics, a San Francisco-based developer of therapies for novel inflammatory and respiratory diseases, raised $165 million in Series A funding. Sofinnova Investments and Novo Holdings led the round and were joined by Forbion, Dawn Biopharma, and others.

- Yendo, a Dallas, Texas-based developer of a vehicle-secured credit card, raised $50 million in Series B funding from Spice Expeditions, Autotech Ventures, FPV Ventures, Pelion Venture Partners, and others.

- Sensi.AI, an Austin, Texas-based AI-powered copilot for senior care, raised $45 million in Series C funding. Qumra Capital led the round and was joined by Insight Partners, Zeev Ventures, Entrée Capital, Flint Capital, and Jibe Ventures.

- Routefusion, an Austin, Texas-based financial infrastructure provider, raised $26.5 million in Series A funding. PeakScan Capital led the round and was joined by Silverton Partners.

- Foundation Health, a San Francisco-based developer of AI technology for pharmacy operations, care coordination, and direct-to-patient delivery, raised $20 million in Series A funding. Define Ventures led the round and was joined by Vanderbilt University, Intermountain Ventures, and existing investors.

- CipherOwl, a San Francisco-based institutional cryptocurrency compliance platform, raised $15 million in seed funding. General Catalyst and Flourish Ventures led the round and were joined by Coinbase Ventures, Sancus Ventures, Enlight Capital, and others.

- HiOctave, a San Francisco-based provider of AI technology to help small and medium-sized businesses automate and personalize customer experiences, raised $15 million in funding. Vinod Khosla and Khosla Ventures led the round and were joined by Celesta Capital, Anthology Fund, and others.

- AnyTeam, a San Francisco-based AI-powered sales operating system, raised $10 million in seed funding. SignalFire and Crosslink Capital led the round and were joined by angel investors.

- Knapsack, a Portland, Ore.-based AI-powered digital product creation, raised $10 million in Series A funding. Builders VC led the round and was joined by Crosslink Capital, Epic Ventures, and others.

- Sitehop, a London, U.K.-based encryption platform designed for defense against quantum-powered cyber attacks, raised £7.5 million ($10 million) in funding. Northern Gritstone led the round and was joined by Amadeus Capital Partners, Manta Ray, and others.

- Akua, a Dover, Del. and Bogotá, Colombia-based operating system for payments in emerging markets, raised $8.5 million in seed funding. Flourish Ventures and Cathay Latam led the round and were joined by Atlantico and others.

- Smallest.ai, a San Francisco-based platform for building AI voice agents, raised $8 million in seed funding. Sierra Ventures led the round and was joined by 3one4 Capital and Better Capital.

- Onos Health, a San Francisco-based behavioral health platform, raised $6 million in seed funding. Haystack and Pathlight Ventures led the round and were joined by Bertelsmann Healthcare Investments and Nebular.

- bondu, a San Francisco-based AI-powered toy for kids, raised $5.3 million in seed funding. Makers Fund led the round and was joined by Samsung Ventures, Boost VC, and Founders Inc.

- PAVUS AI, a Santa Clara, Calif.-based platform designed to help procurement teams manage their data, raised $5.3 million in funding. Sentinel Global led the round.

- Previvor Edge, a New York City-based cancer prevention and early detection platform, raised $3.3 million in pre-seed funding. CoFound Partners and Max Ventures led the round and were joined by Humbition Capital, Red Swan Ventures, and Designer Fund.

- Oasiz, a San Francisco-based social platform for playable content, raised $2.5 million in seed funding. a16z Speedrun and The Venture Reality Fund led the round and were joined by others.

- Parallel, a Lehi, Utah-based AI-powered finance platform for startups, raised $2.3 million in seed funding. Night Capital and Tokyo Black led the round and were joined by Penny Jar Capital, Background VC, and others.