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Ashwin Sreenivas spent his childhood in India waking up at 5am and studying until 8:30 at night. History, geography, physics, chemistry, math. Every day, from 4th grade through 12th grade, through the Olympiads and the National Talent Search Exam. He says now, three years into building one of the more successful post-ChatGPT companies in the world, that all of that is precisely why what he does today feels almost easy. "I get to come in here and there's a lot of people and I'm having fun."
That mode is what Decagon runs on. The company Ashwin co-founded with Jesse Zhang in 2023 is now valued at $4.5 billion, has crossed 450 employees in three years, and works with some of the largest enterprises on the planet. The path there has in some ways been simple: don't theorize about where AI is going, talk to customers until the pain is unmistakable, build for that, ship, repeat. Decagon went from zero to $1 million in ARR with two co-founders and no employees.
In this conversation, Ashwin walks through what that means in practice. How Decagon operationalizes a single cultural priority: speed, even when it costs coordination. How they hire 450 people without breaking the bar. How AI has reshaped the IC engineer, the AE, and the VP of EPD. And why, after a year of running 6+ days a week, the thing he and Jesse would tell their earlier selves is: go faster.
Ashwin Sreenivas is the co-founder and CTO of Decagon, the AI customer concierge platform founded in 2023 that serves enterprise customers including Substack, Eventbrite, Duolingo, and Notion and is valued at $4.5 billion. Decagon Labs, the company's in-house model development effort, now powers around 90% of Decagon's model traffic. Before Decagon, Sreenivas co-founded Helia in 2019, an AI startup acquired by Scale AI a year later. He started his career as a strategist at Palantir Technologies in New York. Sreenivas holds a Bachelor's degree (2017) and Master's degree (2019) in Computer Science from Stanford University. Decagon raised $35M in 2024 and has scaled to over 450 employees.
Where to find Ashwin Sreenivas:
• Decagon
• X
• LinkedIn
Where to find Nakul:
• Audacious Ventures
• X
• LinkedIn
Where to find Audacious Ventures:
• Website
• LinkedIn
In this conversation with Ashwin Sreenivas:
00:00 Who is Ashwin Sreenivas?
02:10 How did Jesse and Ashwin decide what to work on at Decagon?
04:19 Why did they reject the top-down market-sizing approach?
13:16 What does Decagon give up to keep moving fast?
17:54 Does Decagon expect their team to be 6-days in-office?
23:33 Why didn't they hire a single employee until $1M in ARR?
27:12 How do you hire 450 people in three years without breaking the bar?
31:20 Are Decagon engineers even writing code anymore?
35:08 How does the IC engineer role change with Claude Code and Cursor?
36:32 Shipping in two days: how does EPD leadership change?
40:15 What are the two types of FDE, and which one do most AI companies actually need?
49:21 How will the human role at Decagon evolve over three years?
57:15 Why did Decagon build its own models in Decagon Labs?
1:00:50 What worries Ashwin most about Decagon today?
1:03:52 How does Ashwin manage his psyche while running this fast?
1:08:00 What hiccups has Decagon had that no one sees from the outside?
1:09:50 Quickfire: overrated advice, AI products, books, red flags
1:12:43 What would Ashwin tell his younger self about Decagon's journey?
Ashwin's sharpest lines from this conversation...
On what actually matters:
"If you build a company doing something that your customers care about, you can mess up everything else in a way and it doesn't really matter."
On founder market fit:
"If you pick the right market, the market will pull the problem and product out of the founding team."
On what Decagon traded for speed:
"The pace of building has changed so quickly. With AI, there isn't that much time for coordination. You have to give somewhere, and we gave for speed."
On packing desks tight:
"I specifically asked our head of workplace to get smaller desks so that people are packed even closer together, so that you can lean over and talk to an exponentially larger number of people."
On responsibility for AI-generated code:
"Use all the tools you have available so that you can move faster, but at the end of the day, you are responsible for the code you push and you should be prepared to defend it rather than say, 'oh, the AI agent wrote it.'"
On hiring red flags:
"It's not a specific flag, but rather that gut feeling of something's a little off and I'm not sure I want to pull the trigger on this."
On the normality of “fires”:
"I guarantee you every fast-growing company, probably without a single exception, they've had a thousand fires internally. Just normal. That's just how it is."
On the advice he’d give his younger self:
"Go faster, hire faster, build faster, get out to the biggest customers faster because the need is real, the market pull is real. You just need to go capture as much of it as quickly as you can."
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