A customer mentioned never having tried New York pizza. A Tennr employee arranged a visit, boarded a plane with a Joe’s Pizza pie, and delivered a fairly literal answer. Trey Holterman likes this story. An ordinary conversational preference had become someone else’s problem to solve, with the small complication of airport security.
It is a useful place to begin with Tennr’s co-founder and CEO. Funding announcements tell you how much money arrived. A pizza on an airplane tells you something about the behavior a boss rewards. In Holterman’s account of company life, initiative deserves room, and a little absurdity can earn its seat.
His own route to the office includes international rowing, computer science, and stand-up comedy. These activities supply three rather different answers to the question of whether you are doing well. A clock is precise. An audience is immediate. A customer can take some persuading to explain why your carefully built software is beside the point.
Before the office, the boat
Holterman grew up in Hillsborough, California, and graduated from Sacred Heart Prep in nearby Atherton in 2017. Before Stanford, he rowed with NorCal Crew. His junior sporting life also included basketball, and his interests already extended to improv comedy. The business résumé would come later; the appetite for several kinds of performance was there early.
In 2016, he took silver in the men’s eight at the World Rowing Junior Championships. He returned to the junior world stage in Lithuania in 2017. These were team results achieved well before anyone could have attached them to a founder narrative. He was a teenager with a place in a boat, a competition calendar, and other people depending on his contribution.
An eight leaves little room for a private interpretation of teamwork. You can have an excellent explanation of your intentions and still disturb the rhythm. That makes rowing an appealing source of business metaphors, though the metaphors can become suspiciously convenient. Put eight ambitious people in an office and the office does not automatically move faster.
Men’s eight
Trakai, Lithuania
Stanford
Seattle supplied the weather
Consider an actual race. At Seattle’s Head of the Lake in November 2017, Holterman sat in the five seat of Stanford’s varsity eight. Conditions deteriorated enough that organizers shortened the regatta to ten of its seventy scheduled events. Stanford’s two eights completed their races anyway.
The varsity boat finished second in 5:31.225, behind Washington’s 5:14.284. Oregon State followed in third. The setting was cold, the result was specific, and nobody needed to convene a meeting to decide what second meant. There was a time, another boat ahead, and work left to do.
That clarity is part of sport’s attraction. A result can be disappointing without being ambiguous. You know the course you were meant to complete. You know which direction counts as forward. The comparison becomes interesting when an athlete leaves that world for a young business, where even the choice of course remains open to argument.
The teammates became co-founders
At Stanford, Holterman combined computer science with rowing and teaching-assistant work. In 2021, he earned first-team All-America recognition from the Intercollegiate Rowing Coaches Association. Peter Chatain received the same distinction; Flynn Traeger and James Wright made the second team. All four were also named National Scholar Athletes.
Holterman occupied the seven seat at the championship regattas. Stanford’s varsity eight finished third at the Pac-12 Championships and fifth nationally at the IRA Championships. The individual honor therefore sits inside a team story, complete with other names and shared results. It was recognition for a contribution to something collective.
The relationships outlasted university. Holterman started Tennr with Diego Baugh, his former rowing teammate, and Tyler Johnson, his former roommate. He had worked as a software engineer at Strava before leaving to build the company. Tennr was founded in 2021 and joined Y Combinator’s Winter 2023 batch.
Teammate and roommate are modest words beside co-founder, but they describe a useful amount of prior acquaintance. You have already seen something of how a person spends time and handles obligations. Starting a business adds unfamiliar pressures to that familiarity. A shared past supplies context; the next decision still has to be made together.
The room was allowed not to laugh
Holterman’s comedy story begins with criticism. During an internship, a manager told him to get public-speaking lessons before addressing the company again. He went looking for a way to become quicker and more comfortable in front of people. Open mics became part of the answer.
He has described spending years with improv and stand-up, returning repeatedly to the experience of rejection. By his later account, he had stopped performing and was concentrating on Tennr. Comedy belonged to his education in discomfort, without becoming a second career he still claimed to maintain.
A microphone is an economical device for exposing the distance between intention and reception. Preparation happens privately; the verdict happens in company. The room has no obligation to reward the hours spent arranging a sentence. An elegant premise can go nowhere. An unexpected detail can carry the evening.
There is an obvious temptation to declare this perfect preparation for selling software. Holterman’s experience supports a more limited, useful observation: he chose to repeat something at which other people could reject him in real time. A person can learn from that arrangement without needing every failed joke to become a business lesson.
The keyboard could wait
Early Tennr involved long stretches of building in his parents’ basement. Holterman later described a problem with the routine: the engineers were spending too much time on their own assumptions and too little with customers. Eventually he stopped coding and filled his calendar with conversations. The change concerned what deserved his discipline.
“Be really honest with yourself,” he says. The instruction sounds simple until the answer threatens the activity that makes you feel competent. Writing software gives an engineer visible work to finish. Asking questions gives another person permission to explain that the work should have been different.
That is the awkward turn in this story. A hardworking founder can keep working harder and postpone the encounter that would alter the plan. There is comfort in knowing what to do tomorrow. There is less comfort in discovering that tomorrow’s task ought to be finding out whether yesterday’s task mattered.
“Be really honest with yourself.”
Trey Holterman, on finding the business bottleneck
An engineer reads the headlines
Holterman brings a similar suspicion of easy explanations to his writing. In August 2025, he published an essay titled “MIT Study Reveals That Custom IT Projects Are Hard.” It questioned the enthusiasm with which people treated a widely discussed report about failed enterprise AI projects as a verdict on the technology alone.
His argument looked at implementation: translating a business problem into requirements, rolling out software, changing behavior, and getting people to use what has been built. He treated those as longstanding difficulties that new tools do not politely remove. He also objected to muddled thinking disguised by automatically generated specifications.
The essay is revealing as an account of his priorities, rather than a final ruling on anyone else’s research. His attention goes to the passage from an attractive idea to an operating business. Where does an intention become a procedure? Who has to change a habit? What happens when the people using the product have a less accommodating day than its designers imagined?
These are unglamorous questions. They also have the advantage of remaining useful after a fashionable phrase has worn out. A company can change the vocabulary in its presentation overnight. The person expected to use its software still needs the thing to make sense on Tuesday.
A bigger team, a shorter distance
By June 2025, Tennr had announced a $101 million Series C led by IVP. Participants included Andreessen Horowitz, Lightspeed, GV, ICONIQ, Foundation Capital, and Frank Slootman. The announcement also said revenue had more than tripled since the preceding Series B, two quarters earlier. Those figures mark a particular stage of the company, rather than a permanent description of its finances.
Growth brings another audience into the story: employees. Holterman has described the early market experience as humbling for the founders and has spoken about gratitude toward the people they get to hire. That is an interesting counterpoint to the customary image of the founder as the person doing everyone else a favor.
His vocabulary for the workplace includes Cowboy and Confrontation. He wants people to take responsibility and to challenge what is happening, including the boss. The pizza delivery is his cheerful example of the first impulse. His willingness to admit uncertainty in a room is meant to make the second easier.
There is a connection here to the earlier settings, though it is a question of interpretation. A crew depends on contributions the individual cannot supply alone. A comic needs the response of the room. A CEO who wants useful disagreement has to leave space for an answer he did not rehearse.
Holterman’s career offers plenty of recognizable milestones. The more interesting movement happens between them, when a familiar skill stops answering the next question. He can keep the discipline, the technical training, and the willingness to stand in front of people. He still has to listen when somebody suggests a different course. Sometimes the suggestion concerns software. Occasionally, it comes with pizza.