Seventeen interviews from the WorkOS booth at AWS re:Invent 2025 in Las Vegas, produced by Free Agent Media for WorkOS. The flagship: Ben Gilbert and David Rosenthal of Acquired on what makes companies last.
AWS re:Invent 2025 ran December 1 to 5 in Las Vegas, and WorkOS spent the week at its expo booth interviewing the founders and builders who stopped by. Free Agent Media shot and cut all of it: seventeen interviews with eighteen guests from seventeen companies, four hours and eighteen minutes of finished video, published on the WorkOS YouTube channel between December 19 and January 27. The guests run from open-source framework creators like Laravel's Taylor Otwell to infrastructure CEOs like PlanetScale's Sam Lambert, security practitioners, and the engineers building AI agents for on-call, browsers, builds, and healthcare claims.
The flagship is the day-three visit from Ben Gilbert and David Rosenthal of Acquired, cans of Coca-Cola in hand to match their latest episode, who sat down with WorkOS founder Michael Grinich for twenty minutes. The show has grown entirely by word of mouth and doubled every year, and a Wall Street Journal profile alone brought a quarter-million new listeners. Ben and David explain why they stopped covering acquisitions and IPOs and started studying only the companies that stayed on top for decades: the outliers are the interesting ones, and most businesses are not durable.
From there it becomes a working theory of durable companies. The ones that last are N of one. They define a market rather than compete in one, the way Nvidia did by putting CUDA in every chip years before anyone cared, or Costco did by carrying 4,000 items on pallets. Luck is an enormous part of it, but to be a three-or-four-standard-deviation outlier a company also needs the skill, the execution, and the timing. Jensen Huang's version: stand close enough to the tree that when the apple falls you can dive and catch it.
Michael brings it back to the moment. AI has opened a window where enterprises will adopt tools from companies that are months old, which is why startups now need to be enterprise ready far earlier than they used to. That same theme runs through the other sixteen conversations below: Ciroos landed enterprise production deployments nine months after founding, Cleric and Incident.io are putting agents on call, Depot is watching AI-written code overwhelm CI pipelines, and Forrest Brazeal puts the whole week in one line. You can vibe code. You cannot vibe trust.
“It's not just the LLMs. It's changing the way people build applications. The whole software stack is kind of getting turned over, and it feels like a very unique moment for startups to leap ahead.”
“There's no playbook. Every great company does not follow a playbook. They're N of one in their own way.”
“To be that big of an outlier, you need to be the most skilled and you need the most luck and you need the best execution. If they're a video game character, they maxed out everything.”
“Our products haven't really changed that much in the last few years. What's changed around us is the market and the demand for it, and that acceleration is what's led to us growing.”
“A company is a shadow of a person. It's the founder's shadow. It's almost like a company is just leverage on the founder.”
“It's a 2,000-person auditorium and a two-hour show where we're interviewing the CEOs of AWS, JPMorgan Payments, Netflix, and Perplexity all back to back.”
Conference & event coverage · Podcast production
Free Agent Media produced 17 videos for WorkOS at AWS re:Invent 2025, December 1 to 5, 2025. Formats: Conference interview.
Everything cut from the project, each published by WorkOS as its own video. Click through to watch on their channel.
20:40Twenty minutes at the WorkOS booth on what separates companies that last for decades from everyone else, and why the AI wave has opened a window for startups.
“There's no playbook. Every great company does not follow a playbook. They're N of one in their own way.” 07:09 ↗
11:40Why Incident.io treats incidents as urgent reactive work rather than rare outages, running dozens a day, and how its multi-agent investigator went from convincing demo to grounded product.
“It's so easy to produce a convincing demo. It's really hard to discern what is snake oil from what is really good product.” 10:18 ↗
18:54Laravel's path from a 2011 side project to a 90-person company with Laravel Cloud, and how a local MCP server feeds coding agents version-specific docs so they write better PHP.
“I spent years crafting this great DX and now no one actually cares about the code because the agent just writes all the code.” 12:03 ↗
17:45A fifth-time founder on why mean time to repair has barely moved in twenty years, and how Ciroos puts domain agents where the telemetry already lives so root cause arrives before anyone joins the call.
“The capability of some of our agents is at a level where even my distinguished engineers can't match up. We're not even talking about speed. The quality of the investigations is so much better.” 12:35 ↗
11:45Why a database built for agents has to boot and fork instantly, expose MCP tools as affordances, and lean on retrieval, because agents don't remember, they retrieve.
“Agents don't click, they call. They don't click UI, they call APIs.” 03:23 ↗
09:43Why Cleric hands findings back to the engineer at the five-minute mark instead of running autonomously for twenty, and where models still fall for red herrings.
“Agents can't do long horizon tasks without grounding. Unlike with coding, there's no test cases in production. So you need the engineer.” 03:29 ↗
22:06How Vitess scaled MySQL to billions of queries a second at YouTube and Facebook, why Postgres won on vibes more than merit, and the thinking behind PlanetScale's five-dollar tier.
“No one wants that stuff. They just want a really good database and they're going to build good companies on top of it.” 21:00 ↗
14:58Baseten's three-line pitch, the shift to blended open-source model strategies as open models cross capability thresholds, and treating GPUs across every cloud as one pool.
“We do three things. We get the GPU, we put the model on the GPU, and we make it run really fast.” 00:28 ↗
13:19Why running browsers in the cloud is hard, how Stagehand turns natural-language instructions into self-healing automations, and the 50-year-old dairy company that automated gas-price lookups for its truckers.
“We've done hundreds of years of browsing this year at Browserbase. We've deleted hundreds of years of people going to websites and clicking buttons from the universe.” 03:48 ↗
18:02Why a startup's first security hire is secretly ten jobs, why the best security intervention is sometimes an IT help desk, and how LLMs opened Latacora's internal tools to non-programmers.
“If they're honest in the job description, they're asking for a unicorn. They're asking for like ten people.” 00:27 ↗
14:31AI is producing exponentially more code than delivery pipelines were built for, so the build step has to be treated as a production system, with egress controls on CI runners and correctness before speed.
“The CI build pipeline, the delivery pipeline, that is a production system and needs to be treated as a production system.” 10:45 ↗
17:03The Slack data-scientist agent that has answered over 200 analytics questions at Vercel and saved its VP of data thousands of minutes, plus Sign in with Vercel and when MCP is unnecessary overhead.
“Two hundred queries times twenty minutes. We've saved the VP of data 4,000 minutes of his time.” 04:12 ↗
10:13Why shipping software got easier but earning enterprise trust didn't, and why vibe-coding the authentication stack is the one shortcut that can end a business.
“You can vibe code. You cannot vibe trust.” 00:51 ↗
11:52How HIPAA's X12 EDI schemas make Stedi a compiler for healthcare claims, and how the team launched its clearinghouse in five days after the largest one in the country went down.
“You can think about what Stedi has built as a compiler for healthcare, and that is a tailor-made, perfect use case for AI.” 03:42 ↗
20:44Intercom decided to go all in on AI the weekend ChatGPT launched, spun Fin out as its own brand, and now points 70 to 80 percent of R&D at it while pushing engineering toward twice the throughput.
“GPT-3.5 came out and very quickly we realized that this stuff's going to eat our lunch. Do we disrupt ourselves, or do we wait around to get disrupted?” 05:03 ↗
11:34Modal rewrote the infrastructure stack for spiky GPU inference, scaling to a thousand GPUs in minutes, and sees most AI revenue coming from startups rather than enterprises so far.
“VCs are always like, you've got to go to enterprise, that's where the revenue is. The revenue today in AI is actually, ironically, mostly in startups.” 07:05 ↗
13:05Tailscale's AI Gateway proxies LLM calls through an identity-aware network so only the gateway holds an API key, with per-user and per-agent quotas, plus ephemeral tailnets as the new sandbox.
“You don't have to distribute API keys to your organization. You don't have to distribute them to your agents.” 02:35 ↗
Free Agent Media, a video production company for technology companies based in San Francisco, Seattle, and New York, produced all seventeen for WorkOS at the WorkOS booth during AWS re:Invent 2025. WorkOS published them on its YouTube channel between December 19, 2025 and January 27, 2026.
Seventeen conference interviews totaling four hours and eighteen minutes, with eighteen guests from seventeen companies: Ben Gilbert and David Rosenthal of Acquired, Taylor Otwell of Laravel, Sam Lambert of PlanetScale, Paul Klein IV of Browserbase, Chris Evans of Incident.io, Andrew Qu of Vercel, Brian Scanlan of Intercom, Erik Bernhardsson of Modal, Kyle Galbraith of Depot, Philip Kiely of Baseten, Zack Kanter of Stedi, Ronak Desai of Ciroos, William Pienaar of Cleric, Ajay Kulkarni of Tiger Data, Laurens Van Houtven of Latacora, Forrest Brazeal of Freeman & Forrest, and Remy Guercio of Tailscale.
AWS re:Invent 2025, Amazon Web Services' annual conference, held in Las Vegas from December 1 to 5, 2025. The Acquired interview was recorded on day three.
Michael Grinich, founder and CEO of WorkOS, interviews Ben Gilbert and David Rosenthal, co-founders and co-hosts of the Acquired podcast. Michael hosts most of the series; Conner Simmons of WorkOS hosts the Forrest Brazeal conversation.
Acquired's word-of-mouth growth, why the show now studies only durable, category-defining companies, what Nvidia, Google, and Costco have in common, the role of luck versus execution, how AI is accelerating enterprise adoption of tools from young startups, and founder DNA in companies like Microsoft, Google, Anthropic, and OpenAI.
Two-camera booth interviews on the re:Invent expo floor, each recorded and cut as a standalone piece for the WorkOS YouTube channel, running from ten to twenty-two minutes. WorkOS later published a written version of the Acquired interview and a takeaways post drawn from the whole series.
