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Grit · 3 min · Sep 21, 2026

A prior startup taught Jesse preferences, not a playbook

His first company clarified his preference for B2B and a cofounder, but taught little about running a team. He says a solo founder also lacks an equal-context partner to test ideas with.

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

His first company clarified his preference for B2B and a cofounder, but taught little about running a team. He says a solo founder also lacks an equal-context partner to test ideas with.

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

“but in terms of like tactically like how to lead a team how to like you know run a company almost zero learning”
Jesse Zhangat 15:07 · Grit15:07

Takeaways

  1. His previous startup helped him understand what kind of company he wanted.
  2. He says tactical company-running lessons did not transfer much.
  3. A cofounder can speed up decisions by sharing context and commitment.

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 bar3:36
  4. 25:17Six customers and $1 million made PMF feel real3:23
  5. 40:57Product marketing fits an early, amorphous company2:41
  6. 30:49A downturn may make recruiting easier3:15

  7. 14:18A prior startup taught Jesse preferences, not a playbook3:04

  8. 54:00Culture values work better as actionable behaviors3:04Up next

Transcript

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

  1. 14:30

    right oh zero relevance zero um the only i think the only relevance is like it just teaches you learnings as you mature right so um that company i was solo founder which i didn't like so that was learning um and so with osha it's like 10x easier and you kind of you kind of have to get lucky finding a co-founder but um we're also remote because it was during covid i was also learning i didn't like that so now we're in person and uh it was also a consumer app so very different and i also i think learning there is consumer is very different from you know b2b and i just gravitate towards b2b a bit more just like mentally so those are the types of learnings that you get and you kind of also learn like intuition of how to evaluate if like an idea is a waste of time or not there's like stuff like that but in terms of like tactically like how to

  2. 15:20

    lead a team how to like you know run a company almost zero learning so most of those things you just pick up along the way or you try to learn from like people that are doing it a year ahead you know yeah i guess like let's just imagine that was like a b2b sas company i'm still not convinced that you would have learned that much i agree does that make sense because everything's faster now in fact you might have learned some bad bad habits yeah exactly so um so anyway maybe if you hit your head hits the pillow tonight and you're like oh my god what's happening you're like well most people feel that way yeah yeah that's true why don't you like why didn't you like besides the obvious like it's lonely why didn't you like doing the solo founder thing Um, I think it's two things. Like one is the psychological piece, right? It's, you know, you feel like you're like a single point of failure for a lot of things. Um, regardless of how big your team is, it's like, uh, uh, like you're the only one that has like the founder responsibility and context. And so, I mean, yeah, tons of respect for a solo founders, but it's just very difficult. And the second one is that you don't really have someone with the same level of like context and commitment to bounce ideas off of.

  3. 16:28

    and so a lot of ideation just takes a lot longer like i think if i have just anyone on our team if we're just like talking out loud and speaking you you arrive at decisions and like probably correct decisions way faster because you're just kind of like just kind of like another brain or another like processing unit now you can actually do some of this with uh clod which is kind of interesting you can use as it's about ideas but it just gives you like a talking like a a way to vocalize ideas and like kind of hear feedback and you kind of eliminate bad ideas really quickly whereas when you're alone and you're seeing your own thoughts it just takes way longer to arrive at ideas that's the other learning i had so i was listening to i read or listened to something