Elad Gil started betting on AI before most of the world took notice. By the time investors began grasping the implications of ChatGPT, Gil had already written seed checks to startups like Perplexity, Character.AI, and Harvey. Now, as the early winners of the AI wave become clearer, the renowned “solo” VC is increasingly focused on a fresh opportunity: using AI to reinvent traditional businesses and scale them through roll-ups.
The idea is to identify opportunities to buy mature, people-intensive businesses like law firms and other professional services firms, help them scale through AI, then use the improved margins to acquire other such businesses and repeat the process. He has been at it for three years.
“It just seems so obvious,” said Gil over a Zoom call earlier this week. “This type of generative AI is very good at understanding language, manipulating language, manipulating text, producing text. And that’s audio, that’s video, that includes coding, sales outreach, and different back-office processes.”
If you can “effectively transform some of those repetitive tasks into software,” he said, “you can increase the margins dramatically and create very different types of businesses.” The math is particularly compelling if one owns the business outright, he added.
“If you own the asset, you can [transform it] much more rapidly than if you’re just selling software as a vendor,” Gil said. “And because you take the gross margin of a company from, say, 10% to 40%, that’s a huge lift. Suddenly you can buy other companies at a higher price than anyone else because you have that increased cash flow per business; you have enormous leverage on the business on a relative basis, so you can do roll-ups in ways that others can’t.”
So far, Gil has backed two companies pursuing this strategy. According to The Information, one is a one-year-old company called Enam Co., focused on worker productivity, which has been valued at more than $300 million by its backers, including Andreessen Horowitz and OpenAI’s Startup Fund.
Though Gil says he can’t discuss specifics of the private deals, he suggests the approach represents something new. “There used to be these technology-enabled roll-ups 10 years ago, and most of them kind of ended up being not really that much of a user of technology,” he says. “It was kind of like a thin veneer painted on to increase the valuation of the company. I think in the case of AI, you can actually radically change the cost structure of these things.”
Whether the approach proves as lucrative as some of his other bets remains to be seen. Gil has famously backed a host of big brands that have produced riches for their backers, including Airbnb and Coinbase, both of which are now publicly traded, and privately held Stripe, whose valuation has bounced around but reportedly settled in the range of $91.5 billion earlier this year, when its earlier backers bought up more of its shares.
Part of the challenge with roll-ups is finding the right team composition — ideally including a strong technologist along with someone who is “very strong in PE” — and “those things don’t go hand-in-hand,” Gil noted. He said he’s met “maybe two dozen of these teams” so far and mostly looked past them, not because they “weren’t amazing” but because “they still need to sort some things out.”
Gil, who has deep relationships with firms across Silicon Valley, may also find himself competing with them more aggressively on roll-ups as more outfits like Khosla Ventures weigh whether or not they should also be pursuing such deals.
One senses that, either way, Gil is not in it for the money at this point if he ever was. He says his ability to spot trends earlier than most comes instead from the heart. “I love technology, and I love progress, and I love just engaging — both with people who are working on important, interesting things, but also the technology itself.”
When GPT-3 launched, for example, Gil was already experimenting with its predecessor, he said. “When GPT-3 came out, it was such a big leap from GPT-2 that you could just extrapolate out the technology curve. You’re like, ‘Oh my gosh, if this keeps going and scaling’ — all the scaling laws were kind of evident — ‘then this is going to be transformative.’”
That hands-on approach continues today with the small team Gil has assembled, including “people with very deep engineering backgrounds” who “periodically play around with all the AI front-end companies. One person on my team just writes a bunch of scripts and we run them, and we look at performance, and we look at tooling, and it’s super hands-on.”
It’s because of that constant tinkering that, after years of uncertainty in the AI market, Gil sees clear winners emerging. “I used to say, even six months ago, that the more I know about AI, the less I know, because the markets were so dynamic; the technologies were so dynamic,” he said. “And I feel like in the last couple months — maybe the last two quarters — a subset of markets have really crystallized.”
In legal, “we kind of know who the one or two main winners are probably going to be. That’s true in health care. That’s true in customer success and support,” said Gil, who clearly thinks these include his own portfolio companies, which he cited in our conversation.
Among these bets is Harvey, which develops large language models for law firms and in-house legal teams and is reportedly in talks to raise new funding at a $5 billion valuation; Abridge, a healthcare AI company that aims to improve doctors’ clinical documentation workflows (and whose $250 million Series D round was co-led by Gil back in February); and Sierra AI, co-founded by famed operator Bret Taylor, which helps companies implement AI agents for customer service. (The company was valued in the billions of dollars right out of the gate.)
Still, Gil is careful not to declare the game over. “I don’t mean to paint the picture that the game is over or that things are done. I think it’s more that there were two dozen companies that all seemed kind of interesting, and maybe now there’s three or four of them [per vertical]. The map of the likely winners is solidified.”
In the meantime, it’s clear in conversation that this moment represents more than just another investment cycle to him. “I just think it’s a really fun period of time, because so much change is happening, and so there’s just a ton to do,” he said.
Being at the intersection of two transformations — not just betting on the future of AI but on the future of how AI will reshape everything else — is “very exciting,” he added.
We’ll have more from our conversation with Gil — which also touched on guardrails, gatekeeping, and how companies can most adeptly integrate the technologies that will make or break their business — in the newest episode of the StrictlyVC Download podcast, which comes out on Tuesday.
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TechCrunch Sessions: AI hits UC Berkeley’s Zellerbach Hall on June 5 — and today’s your shot at AI trivia glory and two tickets for the price of one.
Answer a few brain-busting questions on artificial intelligence, and if you ace it, you might just find a special promo code waiting in your inbox.
Every day brings new questions — so don’t get discouraged if you don’t know today’s answers. But don’t wait too long. The last day of Countdown AI Trivia is June 4. Don’t miss your chance to win big and be part of the AI action this Thursday.
Whether you know which AI model kicked off the large language model revolution or what year OpenAI launched ChatGPT, this is your time to shine.
Step 1: Answer the AI trivia questions on this form
Step 2: Watch your inbox for the special code if you win
Step 3: Use the code to claim your 2-for-1 ticket deal
Show off your AI knowledge in this quick trivia round.
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Artificial intelligence has no shortage of visionaries—but the ones who matter are executing. In 4 days, TechCrunch Sessions: AI brings those builders, researchers, funders, and enthusiasts under one roof at UC Berkeley’s Zellerbach Hall.
This isn’t a parade of AI hype or a string of over-edited keynotes. It’s a single day designed for clarity, candor, and real connection.
It’s also your last chance to save. Ticket prices rise soon — but right now, you can save over $300 on your pass and get 50% off a second, so your partner, co-founder, or friend can dive in with you.
Maybe it’s a fireside chat with Jared Kaplan of Anthropic on frontier models. Maybe it’s a breakout session on enterprise deployment with leaders from SAP. Or maybe it’s a deep-dive conversation sparked through the Braindate app — our smarter tool for face-to-face matching based on shared interests. You never know where the game-changing idea will come from. You just need to be in the room.
So You Think You Can Pitch puts AI startups in front of investors for live, unscripted feedback. It’s fast-paced, transparent, and sharp—exactly what early founders need to understand how real funding decisions happen.
We’ve kept the pricing generous, but the clock is ticking. Save over $300 on your TC Sessions: AI pass and get a second one at 50% off. Group discounts apply too. On June 5, prices go full fare—and with them, your shot at big savings disappears. Lock in your low rate tickets here.
Interested in a deeper discount? Participate in our AI trivia for a chance to purchase a ticket at $200 and receive a second ticket for free.
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TechCrunch Sessions: AI hits UC Berkeley’s Zellerbach Hall on June 5, and we’re kicking Day 3 of AI trivia into high gear. This is your chance to prove you know your stuff — and score a major ticket deal while you’re at it.
Answer a few AI-focused trivia questions, and you could win two tickets for just $200 total. That’s one flat rate and one freebie.
The last day of trivia is June 4 — don’t miss this chance to win big and join the AI epicenter.
Whether you know which company built the first transformer model or how many startups globally integrate generative AI, this is your moment to shine.
Quick AI quiz. Big savings.
Step 1: Fill out the trivia form
Step 2: Watch your inbox for the code if you win
Step 3: Use the code to claim your 2-for-1 ticket deal
The questions are fast. The reward? Even faster. Test your AI IQ and win big before June 4.
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In just 5 days, the sharpest minds in artificial intelligence will gather at UC Berkeley’s Zellerbach Hall for TechCrunch Sessions: AI—a one-day summit built for real insight, not recycled soundbites. Whether you’re training your first model or managing a multi-billion-dollar portfolio, this is where the future of AI feels tangible.
Let’s be honest: AI has officially entered cocktail-party territory. Everyone’s talking, but not everyone knows what they’re talking about. On June 5, TC Sessions: AI cuts through the noise. You’ll hear directly from the people building foundational models, shaping safety protocols, and deciding what gets funded next.
Register now to save $300 on your ticket—and get a second one for 50% off.
Yes, you’ll hear from leaders at OpenAI, Google DeepMind, Amazon, and Anthropic—on the main stage and in breakouts—but also from early-stage founders rewriting the rules in real time. Investors from Khosla Ventures, Accel, Felicis, and Initiate Ventures will take the stage to share what they’re backing, why they’re betting big, and what it takes to stand out in today’s AI landscape.
Take a look at the full TC Sessions: AI agenda and speaker lineup.
And it’s not all big-stage bravado. Our breakout sessions are designed for depth—smaller rooms, bigger conversations. Bring your questions. Bring your prototype. Bring a notebook.
Want to ask burning questions to AI’s biggest names from the front row? Or maybe you’re after the high-impact conversations happening in small group deep dives? TC Sessions: AI has both—and if you miss it, you’re missing the connections and insights that could fuel your next breakthrough.
Tickets are still discounted, but not for long. Grab $300+ off your pass today—and if you’re bringing a colleague, your second ticket is 50% off.
Interested in a deeper discount? Participate in our AI trivia for a chance to purchase a ticket at $200 and receive a second ticket for free.
Doors open June 5. That’s when the prices go up and the real conversation begins.
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We’re thrilled by the overwhelming response to our call for speakers at TechCrunch Disrupt 2025, taking place October 27–29 at Moscone West in San Francisco.
After a careful selection process, we’ve narrowed it down to 20 impressive finalists—10 breakout sessions and 10 roundtables.
Now it’s your turn to help shape the agenda. Audience Choice voting is open until 11:59 p.m. PT tonight. This is your final opportunity to weigh in—vote for your favorite sessions and help decide which will take the stage. You can vote for as many sessions as you’d like—just one vote per session.
The top 5 in each category will join the official Disrupt 2025 lineup.
Breakout Sessions
How to Get Acquired in Tech (Without Selling Out): M&A Tips for Founders and Builders
Aklil Ibssa, Head of Corporate Development and M&A, Coinbase
Agentic AI for Startups: Automate, Adapt, and Accelerate Growth
Anmol Rastogi, Head of Product, Amazon Business – AI & ML, Amazon
Automation with Agents: From Work Enablement to Work Completion
Chet Kapoor, Chairman and CEO, DataStax
AI at the Brink: Strategic Playbook for National Security
Dan Hendrycks, Executive and Research Director, Center for AI Safety (CAIS)
Leading a Series A Round in 2025 and Sustaining Momentum
Gabriel Kra, Managing Director, Prelude Ventures
The Agentic Apocalypse: Securing the Enterprise in the Age of 1 Billion AI Agents
Jack Hidary, CEO, SandboxAQ
Jim Breyer, Founder and CEO, Breyer Capital
Embracing AI for a Better Digital Future
Matt Madrigal, Chief Technology Officer, Pinterest
Mining for Millions with GenAI’s 4 Ds: Striking Trust, Delight, and Dividends
Michael Stewart, Managing Partner, M12
From Data to Agents: Building the AI-Native Enterprise
Sridhar Ramaswamy, Chief Executive Officer, Snowflake
From Vibes to Velocity: How AI Tools Can Help You Achieve Your Development Goals
Tim Rogers, Staff Product Manager, GitHub Copilot, GitHub
Roundtable Sessions
Future of Space Economy in the Low Earth Orbit
Abhijeet Kumar, Invited Lecturer – New Space Economy, UC Berkeley | Tech and Strategy Lead, Archer
From Startup to Scale-Up: A GTM Blueprint
Anjai Lal, Head of Strategy and Enablement, Google Cloud
From Code to Capital: How VCs Spot the Next AI Powerhouses
Avi Bharadwaj, Investment Director, Intel Capital
The Winning Formula: Turning Your Business Into a Trusted, Scalable Community To Drive Growth
Justine Palefsky and Tasneem Amina, Co-founders, Kindred
Vlad Loktev, Partner, Index Ventures
How to Train Your Model: Taming AI Agents Without Breaking Them
Kyla Guru, Head of Model Cyber Policy, Anthropic
Alex Moix, Investigations Lead, Safeguards, Anthropic
Going a Layer Deeper: Why the future of AI investments lies with infrastructure and applications
Paul Drews, Managing Partner, Salesforce Ventures
Scaling Search and AI for Millions: Lessons from Reddit Search
Rachel Miller, Product Manager, Reddit
AI Evaluation 101: Addressing Challenges to Real-World AI Applications
Rohit Patel, Director, Generative AI, Meta
From Workarounds to Breakthroughs: How UpLink Lets Users Connect Any App—No Integration Needed
Scott Weinert, CTO and Co-founder, Atomic
Whose Company Is It, Anyway?: What You Lose When You Accept Outside Capital
Sridhar Vembu, Chief Scientist, Zoho
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