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Grit · 3 min · Sep 21, 2026

Hard customer discovery helped Decagon escape the idea maze

Jesse Zhang says zero-to-one was the hardest phase, so he and his co-founder pushed through customer discovery quickly. Asking about budgets, ROI and decision-makers helped them test whether an idea was real.

Jesse Zhang

Jesse Zhang is co-founder and CEO of Decagon.

Co-founded Decagon, a conversational AI platform for customer support, and previously founded Lowkey, acquired by Niantic.

  • Joubin Mirzadegan, Host · Partner, Kleiner Perkins

    Took Palo Alto Networks' cloud business from $2M to $50M+ ARR in a year.

About this segment

Jesse Zhang says zero-to-one was the hardest phase, so he and his co-founder pushed through customer discovery quickly. Asking about budgets, ROI and decision-makers helped them test whether an idea was real.

From “Inside Decagon: Finding PMF, Hiring Fast, and Scaling 10x”, Sep 21, 2026. Watch the full episode

“we were like very aggressive about doing this like almost like sales discovery”
Jesse Zhangat 21:20 · Grit21:20

Takeaways

  1. Zero-to-one felt harder than scaling.
  2. Ask about budget, ROI and who makes the decision.
  3. Tough discovery questions can shorten the search for an idea.

In this episode

Full episode
  1. 36:16Decagon differentiates by giving customers control of AI5:04
  2. 19:24Hard customer discovery helped Decagon escape the idea maze3:28

  3. 9:49Decagon uses culture interviews to protect its hiring bar3:36Up next
  4. 5 more moments in the full episode

Transcript

Transcribed by machine (Whisper) from the episode’s audio, so a word may be off here and there.

  1. 19:37

    from the early days now it hasn't the feeling hasn't really changed that much i would say the only time it does change is like like when you're in the idea maze to like maybe post pmf and you're scaling like that is a pretty different feeling and i think no matter what anyone says the the early like zero to one phase is like way more way harder it's awful yeah so yeah every stage has it's challenges about the zero to one phase is like by far the hardest once you're past that phase at least in my experience the general feeling is the same like the stuff you're doing is different but like you know it's enjoyable you know it's like kind of a privilege to be in a fast-growing company or have like this is even though like every day is not easy it's like you know this is what we wanted to do and so you have to be a bit thankful that you know this is um you know

  2. 20:26

    things are going well and you know i had my last company as well where like i was in that zero that first phase for like forever how long uh like three years maybe come on um well i was yeah i was a new grad i was like 20 at the time and i like so when you're a new grad you're like super fresh you you probably think you're like i mean we thought we were like quite smart and very technically strong whatever but you just like don't really know how to do stuff yeah so we like spent a bunch of time like working super hard on stuff that was like okay we just thought about this for a few for a little bit more it's like you could tell this is a bad idea uh and now yeah so that phase is just much tougher and so now because i have that perspective it's like it's easy to have appreciation for when you're not doing that you know how long were you in the

  3. 21:11

    idea maze for dacagon like three weeks come on yeah so we um we arrived uh maybe a bit longer than that but it's like rough rough order of magnitude it was very fast because we our main goal when starting the company was like let's not be in the idea base you know that sucks so instead of picking idea we just um we were like very aggressive about doing this like almost like sales discovery i talked about this before but like i think most founders shy away from being as aggressive as you need to be in that phase because it feels like you're being too pushy or too salesy but no one really cares about that like your your founder starting a new company like they'll appreciate if you're asking like more tough questions like you know how much how much we pay for this you know where's the budget coming from like how do you justify ROI internally like

  4. 22:03

    who are the people involved like those are people those are questions that like a salesperson should ask in like a sales cycle but early on founders tend to not do that and they're just doing things like would you use this like you know yeah how useful that would this be for you and like if you're not asking the hard questions it's hard to tell so i think through that process we decided like hey this is like the obvious thing to build and that was in hindsight helpful i mean you have to be a bit lucky obviously but i think that process helped us avoid a super drawn out initial phase how long before you raised your first round well technically we raised our seed round like