Ben Gilbert and David Rosenthal from Acquired on what makes companies last
A conversation with the hosts of Acquired podcast.
Ben Gilbert and David Rosenthal have been making the Acquired podcast for years, doubling their audience every single year. This year they stopped by the WorkOS booth at re:Invent before interviewing the CEOs of AWS, JP Morgan Payments, Netflix, and Perplexity in a 2,000-person auditorium. When asked what's different about 2025, their answer was simple: it's felt exponential every year. That's the funny thing about compounding growth—it always feels like this year was the crazy one.
The evolution of Acquired
Acquired started by covering acquisitions, hence the name. Then they realized the best companies don't get acquired; they're the acquirers. They added IPOs. Then they realized covering "the Shopify IPO" was silly when they should just do Shopify.
Now their filter has evolved again: who cares? They can cover great companies with interesting journeys, but if you get to the end and ask "who cares?" then it doesn't belong on Acquired. Nvidia, Costco, Google—these are companies where the question is unthinkable.
What great companies have in common
When asked about the common thread among durable, category-defining companies, Ben and David gave an answer that sounds like a paradox: they're all N of one. They don't follow playbooks. They define their markets rather than competing in them.
Nvidia putting CUDA in every graphics card starting in 2010 wasn't following a playbook. Costco insisting on 4,000 SKUs and warehouse shopping wasn't copying anyone. These are founders with wild creativity whose starting conditions become the durable pillars of the business.
Luck, skill, and full bars
How much of success is luck? An astronomical amount—survivorship bias to the extreme. But here's the framework: to be a three or four standard deviation outlier, you need to max out every bar. Skill, luck, execution, timing. If you're a video game character, you entered the cheat code.
Different founders will tell you different things. Jensen Huang says it's not luck—Nvidia always positioned themselves close enough to the tree that when the apple fell, they could dive and catch it. But that framing still acknowledges they didn't control where the apple would fall.
The AI moment and what it means for startups
Ben and David see the AI era as genuinely different. Enterprises are willing to adopt tools from eight-month-old companies because AI reaches so deep into their systems. The window for startups to land enterprise customers has blown wide open.
They pointed to WorkOS as an example: a pre-AI company that's perfectly positioned because AI companies need to be enterprise-ready much earlier than previous generations of startups. The demand acceleration isn't about the product changing, it's about the market changing around it.
The leadership paradox at foundation model companies
The strangest thing about Anthropic and OpenAI is how important they've become without the battle-hardened leadership teams that typically characterize great companies. Apple's leadership worked together for decades. Google's exec team grew up with the company. The foundation model companies have employees who've been there for six weeks.
Ben and David wonder if these companies can institutionalize founder DNA the way Apple institutionalized Steve Jobs or Microsoft institutionalized Bill Gates. Satya Nadella is a rare example of a "refounding CEO" who captured the founder spirit without being a founder. Can Anthropic and OpenAI do the same?
This interview was conducted at AWS re:Invent 2025.