Day: August 7, 2025

• Startups are told to follow Silicon Valley playbooks like “founder mode.”
• But an angel investor in 350 startups, including Airtable and Rippling, said “that never works.”
• The key is to understand the framework and context and “blend it” into your own company, Immad Akhund said.

Startups are told to run like Airbnb, go full “founder mode,” and follow OKRs — Objective and Key Results. But Immad Akhund, an angel investor since 2016, said copying Silicon Valley playbooks can backfire.

It’s “very easy” to try to copy and paste a Brian Chesky axiom to your situation, Akhund said on an episode of the “In Depth” podcast published Wednesday. “That never works,” he added.

“The lessons work in their particular way for that particular situation, and you have to adapt them to your situation,” he said.

Akhund said the key is to understand the framework and context that made it successful and then “try to blend it” into your own company.

For instance, Akhund, who is the founder and CEO of banking startup Mercury, said people told him to adopt an OKR framework once the company reached a “certain size.”

“When we were small, I was like, ‘OK, this is just silly,'” he said. “We don’t need a structure for objectives, like there are just five people in the room. Let’s just do this.”

He also cautioned against letting metrics dictate every decision.

“Doing like, an extra bit that creates like a magical experience for customers, that’s very hard to measure a metric against,” he said.

It’s dangerous to have everything be driven by metrics, he added.

Akhund has backed more than 350 startups at their earliest stages, including Rappi, Airtable, Rippling, Decagon, and Etched.

Akhund angel invests in “things that will seem inevitable 10 years from now and can be $10 billion companies,” he told Business Insider in a May story about the most successful seed-stage investors.

Mercury, the fintech startup he founded, announced in March that it had raised a $300 million Series C round led by Sequoia at a $3.5 billion valuation.

Akhund did not respond to a request for comment from Business Insider.

Silicon Valley playbooks

Tech leaders have debated about the right way to run their companies.

Airbnb’s Chesky said on an episode of The Verge’s “Decoder” podcast published last month that embracing “founder mode,” a term that he helped popularize, is key to acting like a nimble startup.

“In the age of AI, my argument is you need to be founder oriented/founder mode, because you’re going to need to be able to move like a startup to be able to adapt,” he said. “I think these big, professionally managed companies aren’t organized to be able to do that, so they don’t bode well for this new world.”

Chesky talked about founder mode on the same podcast last year, saying people misunderstand the term. It’s not about “swagger,” he said, but instead about being focused on the details. The whole ethos is “that great leadership is presence, not absence,” Chesky said last year.

But others see the risk in sticking to a single operating mode.

Hussein Kanji, a partner at VB firm Hoxton Ventures, said in a September story by Business Insider that it’s easy to end up down the wrong track “if you live just in one mode.”

“People love making things black and white when the world runs in a lot of different shades of truth,” he said. “People have lost their ability to engage with seemingly contradictory ideas at the same time.”

Some of the most successful tech companies right now are also overseen by leaders who weren’t their founders. Satya Nadella at Microsoft is one such leader, as is Dara Khosrowshahi at Uber.

Axel Springer, Insider Inc.’s parent company, is an investor in Airbnb.