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An angel investor in 350 startups, including Airtable and Rippling, says founders shouldn't copy Silicon Valley playbooks
An angel investor in 350 startups, including Airtable and Rippling, says founders shouldn't copy Silicon Valley playbooks

Business Insider

time07-08-2025

  • Business
  • Business Insider

An angel investor in 350 startups, including Airtable and Rippling, says founders shouldn't copy Silicon Valley playbooks

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.

A founder who bet on 350 startups says passing on a hot AI company taught him a hard lesson
A founder who bet on 350 startups says passing on a hot AI company taught him a hard lesson

Yahoo

time14-05-2025

  • Business
  • Yahoo

A founder who bet on 350 startups says passing on a hot AI company taught him a hard lesson

Immad Akhund passed on Scale AI, now worth $14 billion, because the founders were "so young," he said. The miss taught him to rethink his bias against young founders. The CEO and founder of Mercury has backed more than 350 startups at their earliest stages. Immad Akhund, an active angel investor since 2016, passed on an early bet in Scale AI — worth nearly $14 billion in last year's funding round — and it taught him an important lesson. "I saw Scale AI. And I was like, 'good idea, but these people are so young,'" he said on an episode of the "Twenty Minute VC" podcast published Monday. "I think they were like 19 and 20 at the time or something. I think I could run this company better if I was doing it and I didn't see how they were going to figure it out," he added. Looking back, the serial entrepreneur said he was "just so wrong." "There's some power to that youth that's hard to judge, to be honest. You kind of have to suspend belief and say, okay, this person's going to figure out how to run a huge company," he said. The misstep was a formative one for Akhund, who 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. Akhund is also the founder and CEO of Mercury, a banking startup that recently raised a $300 million Series C round at a $3.5 billion valuation led by Sequoia. Akhund said one of the biggest lessons in his investing journey was learning to check his ego. As an entrepreneur, he was used to suggesting his ideas when speaking with startups, he said. The founders, especially if they were young, would often concur. But "that's not their idea, and it's not even fair to push an idea on other people," he said. He learned that it was important to back founders for their ideas, not for his. "You really have to actually remove your ego and your ideas and really listen," he said. "You're much more along for their journey rather than a major part of it," he added. Akhund said that he prefers serial founders to first-timers, especially those with "a chip on their shoulder." "I have such a bias toward them," he said. "A serial entrepreneur knows how hard it's going to be, but they're willing to do it again." That's "so unusual" and signals that "they must really want to do this," he added. For investors, Akhund advises making diversified bets. "Do at least 20 or 30 investments — that's when you start entering the game," he said. "You learn a lot by doing subsequent ones," he said, adding that investors "need a diversified portfolio to have any return in this space." A representative for Akhund declined further comment. Read the original article on Business Insider

A founder who bet on 350 startups says passing on a hot AI company taught him a hard lesson
A founder who bet on 350 startups says passing on a hot AI company taught him a hard lesson

Business Mayor

time14-05-2025

  • Business
  • Business Mayor

A founder who bet on 350 startups says passing on a hot AI company taught him a hard lesson

Immad Akhund, an active angel investor since 2016, passed on an early bet in Scale AI — worth nearly $14 billion in last year's funding round — and it taught him an important lesson. 'I saw Scale AI. And I was like, 'good idea, but these people are so young,'' he said on an episode of the 'Twenty Minute VC' podcast published Monday. 'I think they were like 19 and 20 at the time or something. I think I could run this company better if I was doing it and I didn't see how they were going to figure it out,' he added. Looking back, the serial entrepreneur said he was 'just so wrong.' 'There's some power to that youth that's hard to judge, to be honest. You kind of have to suspend belief and say, okay, this person's going to figure out how to run a huge company,' he said. The misstep was a formative one for Akhund, who 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. Akhund is also the founder and CEO of Mercury, a banking startup that recently raised a $300 million Series C round at a $3.5 billion valuation led by Sequoia. Leaving his ego at the door Akhund said one of the biggest lessons in his investing journey was learning to check his ego. As an entrepreneur, he was used to suggesting his ideas when speaking with startups, he said. The founders, especially if they were young, would often concur. But 'that's not their idea, and it's not even fair to push an idea on other people,' he said. He learned that it was important to back founders for their ideas, not for his. 'You really have to actually remove your ego and your ideas and really listen,' he said. 'You're much more along for their journey rather than a major part of it,' he added. Akhund said that he prefers serial founders to first-timers, especially those with 'a chip on their shoulder.' 'I have such a bias toward them,' he said. 'A serial entrepreneur knows how hard it's going to be, but they're willing to do it again.' That's 'so unusual' and signals that 'they must really want to do this,' he added. For investors, Akhund advises making diversified bets. 'Do at least 20 or 30 investments — that's when you start entering the game,' he said. 'You learn a lot by doing subsequent ones,' he said, adding that investors 'need a diversified portfolio to have any return in this space.' A representative for Akhund declined further comment.

A founder who bet on 350 startups says passing on a hot AI company taught him a hard lesson
A founder who bet on 350 startups says passing on a hot AI company taught him a hard lesson

Business Insider

time14-05-2025

  • Business
  • Business Insider

A founder who bet on 350 startups says passing on a hot AI company taught him a hard lesson

Immad Akhund, an active angel investor since 2016, passed on an early bet in Scale AI — worth nearly $14 billion in last year's funding round — and it taught him an important lesson. "I saw Scale AI. And I was like, 'good idea, but these people are so young,'" he said on an episode of the "Twenty Minute VC" podcast published Monday. "I think they were like 19 and 20 at the time or something. I think I could run this company better if I was doing it and I didn't see how they were going to figure it out," he added. Looking back, the serial entrepreneur said he was "just so wrong." "There's some power to that youth that's hard to judge, to be honest. You kind of have to suspend belief and say, okay, this person's going to figure out how to run a huge company," he said. The misstep was a formative one for Akhund, who 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. Akhund is also the founder and CEO of Mercury, a banking startup that recently raised a $300 million Series C round at a $3.5 billion valuation led by Sequoia. Leaving his ego at the door Akhund said one of the biggest lessons in his investing journey was learning to check his ego. As an entrepreneur, he was used to suggesting his ideas when speaking with startups, he said. The founders, especially if they were young, would often concur. But "that's not their idea, and it's not even fair to push an idea on other people," he said. He learned that it was important to back founders for their ideas, not for his. "You really have to actually remove your ego and your ideas and really listen," he said. "You're much more along for their journey rather than a major part of it," he added. Akhund said that he prefers serial founders to first-timers, especially those with "a chip on their shoulder." "I have such a bias toward them," he said. "A serial entrepreneur knows how hard it's going to be, but they're willing to do it again." That's "so unusual" and signals that "they must really want to do this," he added. For investors, Akhund advises making diversified bets. "Do at least 20 or 30 investments — that's when you start entering the game," he said. "You learn a lot by doing subsequent ones," he said, adding that investors "need a diversified portfolio to have any return in this space."

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