Jesse Zhang is the co-founder and CEO of Decagon, which builds AI customer service agents. The items below are things Zhang said in podcasts, talks and interviews. — Startup Grind: How I Did It, From Stealth to $100M, Jesse Zhang (Decagon) and Ivan Zhou (Accel) (YouTube), auto-generated captions.

Infographic for "Lessons from Jesse Zhang of Decagon".

On Building a Company and Entrepreneurship

Quotes:

  1. On Training a Neural Network: On the No Priors podcast, Zhang said that if "you're a founder you're like training your own like neural network right and you need like positive examples and negative examples". — No Priors Ep. 132: With Decagon CEO and Co-Founder Jesse Zhang (YouTube, Sept 2025), auto-generated captions.
  2. On Negative Examples: On the No Priors podcast, Zhang said of the first company that "basically the first two years was just like negative examples. You're just like failing". — No Priors Ep. 132: With Decagon CEO and Co-Founder Jesse Zhang (YouTube, Sept 2025), auto-generated captions.
  3. On Not Overthinking the Initial Phase: At a Startup Grind fireside chat with Accel, Zhang said that the biggest learning is that "you can't overthink the initial phase". — Startup Grind: How I Did It, From Stealth to $100M, Jesse Zhang (Decagon) and Ivan Zhou (Accel) (YouTube), auto-generated captions.
  4. On Aggressively Talking to Customers: At a Startup Grind fireside chat with Accel, Zhang said: "we're just going to aggressively talk to as many customers as possible". — Startup Grind: How I Did It, From Stealth to $100M, Jesse Zhang (Decagon) and Ivan Zhou (Accel) (YouTube), auto-generated captions.
  5. On Convincing Yourself: At a Startup Grind fireside chat with Accel, Zhang said that "it's like very easy to kind of convince yourself that this is super competitive space". — Startup Grind: How I Did It, From Stealth to $100M, Jesse Zhang (Decagon) and Ivan Zhou (Accel) (YouTube), auto-generated captions.
  6. On the Market Mattering: At a Startup Grind fireside chat with Accel, Zhang said that "for product market fit the market matters way more and you have to be in the right market at the right time". — Startup Grind: How I Did It, From Stealth to $100M, Jesse Zhang (Decagon) and Ivan Zhou (Accel) (YouTube), auto-generated captions.
  7. On Making Sure You Are in the Right Market: At a Startup Grind fireside chat with Accel, Zhang said: "my biggest learning from these two companies so far is like you really just have to make sure you're in the right market". — Startup Grind: How I Did It, From Stealth to $100M, Jesse Zhang (Decagon) and Ivan Zhou (Accel) (YouTube), auto-generated captions.

Learnings:

  1. On the First Few People: At a Startup Grind fireside chat with Accel, Zhang said: "I think the first couple people matter a lot because they set the tone for the rest of the company". — Startup Grind: How I Did It, From Stealth to $100M, Jesse Zhang (Decagon) and Ivan Zhou (Accel) (YouTube), auto-generated captions.
  2. On Finding the Market: At a Startup Grind fireside chat with Accel, Zhang said: "I think the best way to find the market is to have these conversations and just be very like disciplined about it". — Startup Grind: How I Did It, From Stealth to $100M, Jesse Zhang (Decagon) and Ivan Zhou (Accel) (YouTube), auto-generated captions.
  3. On the Existential Worry: At a Startup Grind fireside chat with Accel, Zhang said of the earliest stage that "you're not sure if it works or not that's like it's kind of like the existential worry that you have". — Startup Grind: How I Did It, From Stealth to $100M, Jesse Zhang (Decagon) and Ivan Zhou (Accel) (YouTube), auto-generated captions.
  4. On Communication as the Team Grows: At a Startup Grind fireside chat with Accel, Zhang said that "communication becomes a lot trickier as the team grows". — Startup Grind: How I Did It, From Stealth to $100M, Jesse Zhang (Decagon) and Ivan Zhou (Accel) (YouTube), auto-generated captions.
  5. On Five Days in the Office: In a Forbes interview, Zhang said: "we're in the office 5 days a week". — Forbes: How This Entrepreneur Built A $1.5 Billion AI Unicorn In One Year (YouTube), auto-generated captions.
  6. On Indexing on Intensity: At the Primary NYC Summit, Zhang said: "we've generally just kind of indexed a lot around the intensity of the team like our initial group and the culture we've built". — Primary Venture Partners: PRIMARY NYC SUMMIT 2025, Jesse Zhang and Belle Lin (YouTube), auto-generated captions.
  7. On Doing Whatever It Takes to Win: On the Upstarts Media podcast, Zhang said of the early team that "that team has really set a culture of just like doing whatever it takes to win". — Upstarts Media: Decagon's Jesse Zhang, Closing Customer Service Doom Loops With AI Concierges (YouTube), auto-generated captions.
  8. On a Competitive Team: On the Invest Like the Best podcast, Zhang said: "we have a very competitive team. Everyone wants to win". — Invest Like the Best: The Future of AI Agents, Jesse Zhang interview (YouTube, Oct 2025), auto-generated captions.
  9. On Selecting for the Office: On the Invest Like the Best podcast, Zhang said that "we've, you know, just selected for people that like being in the office with other people". — Invest Like the Best: The Future of AI Agents, Jesse Zhang interview (YouTube, Oct 2025), auto-generated captions.
  10. On Going Back In Person: On the Kleiner Perkins podcast, Zhang said of the first company: "we were also remote because it was during COVID. That was also learning. I didn't like that. So, now we're in person". — Kleiner Perkins: Inside Decagon, Finding PMF, Hiring Fast, and Scaling 10x (YouTube), auto-generated captions.
  11. On Avoiding the Idea Maze: On the Kleiner Perkins podcast, Zhang said: "our main goal when starting the company was like let's not be in the idea maze. You know that sucks". — Kleiner Perkins: Inside Decagon, Finding PMF, Hiring Fast, and Scaling 10x (YouTube), auto-generated captions.

On AI and the Future of Technology

Quotes:

  1. On Cost per Conversation: On the No Priors podcast, Zhang said that customers think about it as "we have a cost per contact or a cost per conversation. And so when you kind of deploy an AI agent, it makes sense to use the same pricing model". — No Priors Ep. 132: With Decagon CEO and Co-Founder Jesse Zhang (YouTube, Sept 2025), auto-generated captions.
  2. On Having No Seats: On the No Priors podcast, Zhang said of AI agents that "there's not really like a seats concept here". — No Priors Ep. 132: With Decagon CEO and Co-Founder Jesse Zhang (YouTube, Sept 2025), auto-generated captions.
  3. On Per-Seat Software: On the a16z podcast, Zhang said that "in the past, software is based per seat because it's roughly scaled based on the number of people that can take advantage of the software". — a16z: Can AI Agents Finally Fix Customer Support? (Dec 2024), transcript.
  4. On an Orchestration Layer: On the a16z podcast, Zhang said: "it’s kind of like an orchestration layer, I guess, that makes the agent real". — a16z: Can AI Agents Finally Fix Customer Support? (Dec 2024), transcript.
  5. On Agents Not Being a Black Box: On the a16z podcast, Zhang said that "your agents shouldn’t be a black box". — a16z: Can AI Agents Finally Fix Customer Support? (Dec 2024), transcript.
  6. On a Measurable ROI: On the a16z podcast, Zhang said that "if the ROI is very measurable, then it’s very clear what level of work output you’re seeing". — a16z: Can AI Agents Finally Fix Customer Support? (Dec 2024), transcript.

Learnings:

  1. On Being Three Times Better: On the a16z podcast, Zhang said that "you have to make sure that you’re like 3x as good as the incumbent offerings". — a16z: Can AI Agents Finally Fix Customer Support? (Dec 2024), transcript.
  2. On the AI Supervisor Role: On the a16z podcast, Zhang said that "the amount of time people spend going forward in the workplace on building and managing agents, kind of like the AI supervisor type role, is going to shoot through the roof". — a16z: Can AI Agents Finally Fix Customer Support? (Dec 2024), transcript.
  3. On Models Not Being Deterministic: On the a16z podcast, Zhang said that "what people are scared about around LLMs is that they’re not deterministic". — a16z: Can AI Agents Finally Fix Customer Support? (Dec 2024), transcript.
  4. On Instruction Following: On the a16z podcast, Zhang said that "we want the models to get better and better at instruction following". — a16z: Can AI Agents Finally Fix Customer Support? (Dec 2024), transcript.
  5. On Changes That Might Break Things: On the a16z podcast, Zhang said that "if you feel like every change you’re going to make has a big chance of ruining something, then you’re just not going to make changes that quickly". — a16z: Can AI Agents Finally Fix Customer Support? (Dec 2024), transcript.
  6. On Starting with Text: On the a16z podcast, Zhang said that "starting with text makes a lot of sense because that’s what people are more aggressively adopting, and it’s just lower risk for them". — a16z: Can AI Agents Finally Fix Customer Support? (Dec 2024), transcript.
  7. On Voice Latency: On the Upstarts Media podcast, Zhang said that "the voice agent latency matters so much". — Upstarts Media: Decagon's Jesse Zhang, Closing Customer Service Doom Loops With AI Concierges (YouTube), auto-generated captions.
  8. On Rolling Out Incrementally: At the Primary NYC Summit, Zhang said that "you can roll it out incrementally and at any point the agent the AI agent can sort of transfer it to a human agent if you need to". — Primary Venture Partners: PRIMARY NYC SUMMIT 2025, Jesse Zhang and Belle Lin (YouTube), auto-generated captions.
  9. On Offloading the Logic: On the No Priors podcast, Zhang said that "we allow them to offload sort of the logic building to the business users". — No Priors Ep. 132: With Decagon CEO and Co-Founder Jesse Zhang (YouTube, Sept 2025), auto-generated captions.

On Product and Customers

Quotes:

  1. On Agents Non-Technical People Can Build: On the No Priors podcast, Zhang said: "You should have an AI agent that's really easy for non-technical people to work with and for them to build the agent, iterate on it, analyze it". — No Priors Ep. 132: With Decagon CEO and Co-Founder Jesse Zhang (YouTube, Sept 2025), auto-generated captions.
  2. On Making It Better and Better: On the a16z podcast, Zhang said that, when evaluating tools like this, "as time goes on, you have the ability to make it better and better". — a16z: Can AI Agents Finally Fix Customer Support? (Dec 2024), transcript.
  3. On a Web of LLM Calls: On the a16z podcast, Zhang said: "agent for us, you can kind of think of it almost like it’s a web of LLM calls or API calls or like other logic that all works together to produce a better experience". — a16z: Can AI Agents Finally Fix Customer Support? (Dec 2024), transcript.
  4. On Software That Is Thick Enough: On the a16z podcast, Zhang said that "if we really run into trouble is where the software that you’re building on top of the LLM is just not thick enough or not complex enough for someone to feel like, okay, there’s actually differentiation here". — a16z: Can AI Agents Finally Fix Customer Support? (Dec 2024), transcript.

Learnings:

  1. On Hours Spent Working with Agents: On the a16z podcast, Zhang said that "the amount of people’s work hours that go towards working with agents is going to go straight up". — a16z: Can AI Agents Finally Fix Customer Support? (Dec 2024), transcript.
  2. On Evolving Past the Demo: On the a16z podcast, Zhang said: "There’s two properties I would say are very important for something to evolve past the demo". — a16z: Can AI Agents Finally Fix Customer Support? (Dec 2024), transcript.
  3. On a Behavior Shift in Customers: On the a16z podcast, Zhang said: "I think now what’s really cool is that you’re starting to see a behavior shift in the customers". — a16z: Can AI Agents Finally Fix Customer Support? (Dec 2024), transcript.
  4. On Cleverness and Latency: On the a16z podcast, Zhang said: "Because latency is lower, you have to be more clever about the way you’re doing computation". — a16z: Can AI Agents Finally Fix Customer Support? (Dec 2024), transcript.

On Personal Growth and the Founder's Mindset

Learnings:

  1. On Rationalizing: In an EO interview, Zhang said that "as a Founder you can always overthink things and you can always rationalize different things but at the end of the day it doesn't really matter you just have to get to a point where you have customers that really appreciate and value what you're doing". — EO: From Zero to $1.5B Unicorn in 2 Years, Decagon, Jesse Zhang (YouTube), auto-generated captions.
  2. On the First Stage: On the Invest Like the Best podcast, Zhang said that "the first stage is like by far the hardest cuz you you're kind of just like finding direction". — Invest Like the Best: The Future of AI Agents, Jesse Zhang interview (YouTube, Oct 2025), auto-generated captions.
  3. On Having Your Legs Under You: On the No Priors podcast, Zhang said that "once you have your legs under you, you both can think more long term". — No Priors Ep. 132: With Decagon CEO and Co-Founder Jesse Zhang (YouTube, Sept 2025), auto-generated captions.
  4. On Strengths and Weaknesses: In a Forbes interview, Zhang said that the most relevant advice is to "understand what your own strengths and weaknesses are". — Forbes: How This Entrepreneur Built A $1.5 Billion AI Unicorn In One Year (YouTube), auto-generated captions.
  5. On Learning from Others: On the Upstarts Media podcast, Zhang said: "we're always trying to learn from like what do people do well". — Upstarts Media: Decagon's Jesse Zhang, Closing Customer Service Doom Loops With AI Concierges (YouTube), auto-generated captions.
  6. On Being the Main Character: On the Kleiner Perkins podcast, Zhang said that "we're the main character on our journey". — Kleiner Perkins: Inside Decagon, Finding PMF, Hiring Fast, and Scaling 10x (YouTube), auto-generated captions.
  7. On a Market That Is Not Growing: At a Startup Grind fireside chat with Accel, Zhang said that "it's just way harder if you're in a market that is not growing or it's not a great market or it's small or people don't have money to buy stuff". — Startup Grind: How I Did It, From Stealth to $100M, Jesse Zhang (Decagon) and Ivan Zhou (Accel) (YouTube), auto-generated captions.
  8. On the Market You Are In: At a Startup Grind fireside chat with Accel, Zhang said: "the market you're in matters a lot". — Startup Grind: How I Did It, From Stealth to $100M, Jesse Zhang (Decagon) and Ivan Zhou (Accel) (YouTube), auto-generated captions.
  9. On Asking What They Will Pay: At a Startup Grind fireside chat with Accel, Zhang said: "ask people how much they're going to pay for certain things, and then, you know, get them to actually pay for it". — Startup Grind: How I Did It, From Stealth to $100M, Jesse Zhang (Decagon) and Ivan Zhou (Accel) (YouTube), auto-generated captions.
  10. On Asking How Much They Would Pay: On the Invest Like the Best podcast, Zhang said of asking customers how much they would pay that "it kind of is a forcing function for finding some order of magnitude, some level of scale". — Invest Like the Best: The Future of AI Agents, Jesse Zhang interview (YouTube, Oct 2025), auto-generated captions
  11. On Being a Single Point of Failure: On the Kleiner Perkins podcast, Zhang said of being a solo founder that "you feel like you're like a single point of failure for a lot of things". — Kleiner Perkins: Inside Decagon, Finding PMF, Hiring Fast, and Scaling 10x (YouTube), auto-generated captions
  12. On Not Being Good at Talking to Customers: In Notion's First Block interview, Zhang said of the first company: "it's not that we didn't talk to customers. I think we're just not very good at talking to customers. And so that was the biggest learning". — Notion: First Block, Interview with Jesse Zhang, Co-Founder and CEO of Decagon (YouTube, Nov 2025), auto-generated captions
  13. On Deciding to Pivot: At a Startup Grind fireside chat with Accel, Zhang said that "I don't think anyone else can tell you when that is". — Startup Grind: How I Did It, From Stealth to $100M, Jesse Zhang (Decagon) and Ivan Zhou (Accel) (YouTube), auto-generated captions

Sources