Jesse Zhang

Jesse Zhang says Decagon's customer support AI is built, tested, and monitored inside the product, so the customer owns the results and the process. People from Decagon still stay on the account, because an enterprise rollout is not a handoff of software to go use alone. The build is not code an engineer has to reconfigure, and not a change Decagon has to come back and make.

Sierra gets into enterprises and has scaled its team quickly. Sierra's deployment is closer to Palantir: forward-deployed engineers who tell the customer they can solve the problem. A do-it-for-you model fits a large company that lacks the talent to move fast. The same model makes less sense as AI models get better, bec

Jesse Zhang says Decagon got out of the idea maze in roughly three weeks, maybe a bit longer. He calls the timing a rough order of magnitude, and it was very fast, because the goal at the start was not to sit there picking an idea.

The team ran something close to sales discovery instead. Most founders avoid questions that feel pushy or salesy. Nobody really cares, and the useful questions are the ones a salesperson asks later: how much do you pay for this, where does the budget come from, how do you justify the ROI internally, and who is involved. Asking whether someone would use a product does not tell you enough. The harder questions are how they decided the product was the obvious thing

Jesse Zhang says the zero-to-one phase is by far the hardest stage of a company, and he calls it awful. Every stage has challenges, and none of the later ones match the early stretch.

The work does not feel different from one day to the next, the way getting taller does not announce itself on a single morning. The feeling changes once, when a company leaves the idea maze and starts scaling. After zero to one, the tasks are different and the general feeling stays about the same. A fast-growing company is still not easy every day, and he treats the pace as the work they wanted. At his last company he stayed in the first phase for maybe three years. He was about 20 and a new graduate, and the

Jesse Zhang says Decagon went from roughly 50 or 60 people to 500 in about the last year, close to a 10x jump. A year ago the headcount was something like 50.

The growth did not come from hiring ahead. For the first year and a half, and through about the first 100 people, Decagon hired only when the team felt the pain of a missing role. He and his co-founder did the early sales, and the first salespeople showed up when deals were already waiting for them. Companies that hired ahead and then had to fire people were the warning, so Decagon stayed lean on purpose. In hindsight the demand was real and they could have hired more, but they did not know that at the time. They hire ahead now, becau

Jesse Zhang says office politics starts as soon as there is a team. He has always been allergic to it, and at Decagon they try to stamp it out aggressively as soon as it appears. He hopes the company stays fairly apolitical, and when politics does show up they push back hard.

Someone who says they should own work another person already owns gets a direct question back: should they not worry about their own work, since there is already plenty to do? An early engineer came to him with feedback on a coworker based on something they saw and started telling the story. He stopped the engineer immediately and told him to go tell the person. The alternatives were for Zhang to deliver the message on

Jesse Zhang says a team of 200 people cannot eat dinner together anymore. Catering has one clear value: everyone eats at the same time.

He used to tell people to remember the old office. It was less nice than the current office, and he wanted them to hold onto it as the good old days, when everyone was eating dinner together. At 200 people a shared dinner is impossible. People still eat together, but they order food and it arrives at different times, so the meal is trickier. The team ran a catering experiment. People liked it because it felt like the old days, when everyone ate together. They thought the food was bad, so he plans to find better food. The dynamic of eating at the same time s

Jesse Zhang says wanting the same things out of life matters more than knowing a co-founder for five years. Y Combinator tells founders to work with someone they have known for five years. He does not agree. The most important question is whether both people want the same things, are equally committed to being a founder, and want the same thing out of the company. When goals are not aligned, and he thinks they are not aligned for most founders, the partnership is going to be tough. After that comes whether the two operate at the same level. A long friendship can make alignment more likely, but alignment matters more than years of knowing each other.

He and his co-founder already had a lot o

Jesse Zhang says very few people have left Decagon, a few have gone to start their own companies, and even in a downturn it will still be pretty easy to start a company. The only good thing about a downturn may be that recruiting gets easier.

The last few quarters have been very good. When the team recaps a quarter, everyone is told to get ready, because it is not always going to be so easy, and to build grit now. Too many companies make recruiting very difficult, and it is really easy to be a founder. A lot of people at Decagon have a strong entrepreneurial sense. They were founders before or they want to be founders. With a very low barrier to entry, people start companies even if they do

Jesse Zhang keeps Saturday as wife day because he and his co-founder are in every day except Saturday, and that one day has to stay free of work. Saturday is sacred. The point is to do whatever you want, hang out, and not do work.

Early on, people would come in on Sundays as well, but there was never an expectation that someone joining would have to come in on Sunday. They are okay with people having lives and not being on Sundays. Around 20 to 30 people, not everyone was going to be in every Sunday. Roughly that size of group still comes in on Sundays, but most people are just doing work and are not in the office. Sunday is a great time with no meetings, so people get thoughts in order and

Jesse Zhang felt Decagon's new office was too big the moment the team moved in. He had left the KP office in January for a room he expected would fit 30 or 35 people and last the year. Four months later the team was spilling on top of each other, and on Monday they moved into a place that fits like 120 people.

The feeling was a weird cognitive dissonance. One side of him thought the space was nice. The other side was freaking out, asking whether they would fill it, how quickly they would fill it, whether it was too big right now, whether it was too nice, and whether they had earned it.

Things were going well, and the overflow was a good problem, but the jump from a plan built for 30 or 35

Anthony Zhang says he loves building Vinovest in Los Angeles for the life as much as the hiring pool. He names the beach, the weather, Hollywood, fashion, and real estate, and he says the talent is not one industry deep. Founding teammates had worked at Snapchat, at ByteDance, the parent company of TikTok, and at Headspace. He thinks people in the city are generally happier. His picture of a day is twelve or thirteen hours of hard work and then a separate life with friends, which he says is available there in a way that keeps the job from becoming the whole day.