• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia
NewslettersTerm Sheet

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

Allie Garfinkle
By
Allie Garfinkle
Allie Garfinkle
Senior Finance Reporter and author of Term Sheet
Down Arrow Button Icon
Allie Garfinkle
By
Allie Garfinkle
Allie Garfinkle
Senior Finance Reporter and author of Term Sheet
Down Arrow Button Icon
October 10, 2025, 5:29 AM ET
OpenAI COO Brad Lightcap.
OpenAI COO Brad Lightcap.OpenAI

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. 

Recommended Video

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
Submit a deal for the Term Sheet newsletter here.

Joey Abrams curated the deals section of today’s newsletter. Subscribe here.

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.

Private Equity

- Systems Planning & Analysis, a portfolio company of Arlington Capital Partners, acquired Group W, a Vienna and Dumfries, Va.-based data science and defense analytics company. Financial terms were not disclosed.

Funds + Funds of Funds

- Ecosystem Investment Partners, a Baltimore, M.D. and San Francisco-based private equity firm, raised $400 million for its fifth fund focused on large-scale wetland, stream, water quality, biodiversity and habitat mitigation and restoration projects.

People

- Halifax Group, a Washington, D.C.-based private equity firm, promoted Jamie Cavanaugh to managing director.

This is the web version of Term Sheet, a daily newsletter on the biggest deals and dealmakers in venture capital and private equity. Sign up for free.
About the Author
Allie Garfinkle
By Allie GarfinkleSenior Finance Reporter and author of Term Sheet
LinkedIn iconTwitter icon

Allie Garfinkle is a senior finance reporter for Fortune, covering venture capital and startups. She authors Term Sheet, Fortune’s weekday dealmaking newsletter.

See full bioRight Arrow Button Icon

Latest in Newsletters

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

Most Popular

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • Future 50
  • World’s Most Admired Companies
  • See All Rankings
Sections
  • Finance
  • Leadership
  • Success
  • Tech
  • Asia
  • Europe
  • Environment
  • Fortune Crypto
  • Health
  • Retail
  • Lifestyle
  • Politics
  • Newsletters
  • Magazine
  • Features
  • Commentary
  • Mpw
  • CEO Initiative
  • Conferences
  • Personal Finance
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
About Us
  • About Us
  • Editorial Calendar
  • Press Center
  • Work At Fortune
  • Diversity And Inclusion
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • Pinterest icon

Latest in Newsletters

NewslettersMPW Daily
Trump Accounts, Epstein files and GLP-1s: 3 Super Bowl ads that reflect today’s biggest conversations
By Emma HinchliffeFebruary 9, 2026
16 minutes ago
A hybrid meeting between both virtual and in person employees.
NewslettersFortune CHRO
AI notetakers are creating HR nightmares
By Kristin StollerFebruary 9, 2026
3 hours ago
NewslettersFortune Crypto
Crypto is facing an identity crisis—but it’s hardly the first time
By Jeff John RobertsFebruary 9, 2026
4 hours ago
NewslettersCFO Daily
The Knot has a new CFO who is doubling down on AI
By Sheryl EstradaFebruary 9, 2026
4 hours ago
C-SuiteNext to Lead
Disney’s $27 million retention deal pays its No. 2 a higher base salary than her boss
By Ruth UmohFebruary 9, 2026
5 hours ago
NewslettersTerm Sheet
Meta expands its already massive Louisiana data center project
By Allie GarfinkleFebruary 9, 2026
5 hours ago

Most Popular

placeholder alt text
Economy
Elon Musk warns the U.S. is '1,000% going to go bankrupt' unless AI and robotics save the economy from crushing debt
By Jason MaFebruary 7, 2026
2 days ago
placeholder alt text
Economy
Russian officials are warning Putin that a financial crisis could arrive this summer, report says, while his war on Ukraine becomes too big to fail
By Jason MaFebruary 8, 2026
19 hours ago
placeholder alt text
Commentary
America marks its 250th birthday with a fading dream—the first time that younger generations will make less than their parents
By Mark Robert Rank and The ConversationFebruary 8, 2026
1 day ago
placeholder alt text
Success
Gen Z Patriots quarterback Drake Maye still drives a 2015 pickup truck even after it broke down on the highway—despite his $37 million contract
By Sasha RogelbergFebruary 7, 2026
2 days ago
placeholder alt text
Commentary
We studied 70 countries' economic data for the last 60 years and something big about market crashes changed 25 years ago
By Josh Ederington, Jenny Minier and The ConversationFebruary 8, 2026
1 day ago
placeholder alt text
Personal Finance
Tom Brady is making 15 times more as a commentator than he did playing in the big game thanks to $375 million contract 
By Eva RoytburgFebruary 8, 2026
1 day ago

© 2026 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.