The new venture has no outdoor golf course. It has a putting lab, eight planned simulator suites and, if Dave Rogenmoser gets his way, people who come by even when their swing is hopeless. The Mackenzie Club, taking shape in the Austin area, looks at first like a peculiar next act for the co-founder of an AI writing company. But the idea begins somewhere older than a language model: on $25 municipal courses, where his father and grandfather taught him to play. In his telling, the score mattered less than the hours beside them. The club is an attempt to give those hours an address.
Rogenmoser made his name with Jasper, the marketing AI company he started in 2021 with Chris Hull and John Phillip Morgan. Its ascent was startling enough to compress the backstory. Jasper reached a unicorn valuation in roughly 18 months, and a $125 million financing round followed in October 2022. The usual telling begins there, with the growth curve. His own account begins with a wedding, a small revenue target, a portable-toilet rental company and a software product that stopped growing.
The wedding, the wager and the $300 client
Rogenmoser grew up in Topeka, Kansas. He has recalled that the biggest business figure he knew there owned a few Wendy's franchises. Later, while working for a campus ministry at the University of Missouri, he wanted to learn how to start a business. At a wedding he sat next to Hull, then a loose acquaintance, and asked what he was doing. Hull was taking a course about starting a software company without an idea, money or coding skills. Rogenmoser wanted in.
The group that eventually included Morgan set a modest sounding target: build a company that brought in $6,000 a month and supported their families. The more unusual condition was that their friendship would outrank the business. They tried software ideas, then marketing services. Their first agency client paid $300 monthly for search work for a portable-toilet rental company. Glamour had apparently taken the week off. The client gave them something more useful: a reason to learn what paying customers actually needed.
Courses came next. They taught marketers techniques they had used themselves, and built an audience that would matter years later. That audience was no overnight miracle. It was accumulated trust, one lesson and one customer at a time. They still wanted a scalable software company. A conversion widget developed around their course business became Proof, a product that displayed recent customer activity on websites to encourage others to buy.
Proof was rejected on its first Y Combinator application. The team kept building, reapplied and entered the accelerator in its winter 2018 batch. After Demo Day, the company raised $2.2 million. These are the facts of a promising startup, though they are also the prelude to the part founders often edit out. Proof's growth stalled. Its technology had become hard to change. Rogenmoser later described a product built into a corner, with changes increasingly demanding a larger rewrite.
A feature grows up, then runs out of room
He has been blunt about the second failure: the team delayed facing the market. Funding bought time, and time made it easier to postpone the awkward question of whether users wanted the next version. Some of the people they consulted were friends inclined to be kind. When the product reached launch, the gap between polite feedback and real demand became plain. The founders laid off much of the Proof team and wound down the venture in 2020.
“Next time, we will launch and get a user on it within a month.”Dave Rogenmoser, recalling the lesson after Proof
The rule was less romantic than a grand vision. Get the thing in front of someone. Ask for payment. Let the answer alter the plan. Morgan also made Jasper's product architecture more modular, Rogenmoser has said, so a component could be replaced without rebuilding the whole application. Proof's limitations became design requirements for the next attempt.
At the time, Rogenmoser had returned to marketing coaching. One course taught business software marketers how to run Facebook ads. He had a formula for writing the copy, but students' assignments were poor enough to worry him. Writing every ad himself would be exhausting. He had seen talk of OpenAI's GPT-3 and wondered whether it could do the first pass. It could. The team knew the buyer, had an audience to reach and recognized a task that people were already trying to complete.
The first version was tightly framed: a way to write Facebook and Google ads. It launched under the name Conversion.ai in early 2021. Users asked for more than ad copy, so the product widened to longer content and eventually carried the Jasper name. Rogenmoser has described the early growth strategy without secret sauce: the team knew marketers, hired carefully and built a community where users could teach one another. That community also gave the company feedback about what to build.
An overnight story with an eight-year fuse
There is a temptation to describe Jasper as a company born in the right week. GPT-3 had become accessible; marketers were hungry for content; AI copy was suddenly good enough to be useful. The timing mattered. So did the years spent selling services, teaching advertisers, building a software product and learning why that product failed. By the time Jasper launched, the three co-founders already knew one another's working habits and had a circle of potential users. Speed at launch had been purchased with a long apprenticeship.
It also produced a problem no earlier venture had offered: what to do when the business outgrew the job its founding CEO was best placed to do. In September 2023 Jasper announced that Timothy Young, formerly president of Dropbox, would become CEO. Rogenmoser remained chairman of the board. He said Young's experience scaling large technology companies made him the right person for Jasper's next phase, which increasingly centered on enterprise marketing teams. Handing over the role put a human face on a familiar founder transition. The person who can find the first customer may decide someone else should run the much larger operation.
His public posts since then are full of golf. There are jokes about lost putts, the tiny indignities of practice and the satisfactions of a round with friends. He has written about missing a three-footer on the seventeenth hole in a friends' Ryder Cup-style event. The memory appears to have found its way into his enthusiasm for a high-tech putting lab. A data-loving software founder, he jokes, can now collect increasingly sophisticated evidence that the problem is himself.
A clubhouse as a product
The Mackenzie Club is planned as a private indoor golf and social club in West Lake Hills, near Austin. The official plan describes a roughly 33,000-square-foot clubhouse over three levels, with eight private TrackMan suites, a PuttView putting lab, coaching, dining and places to work or gather. Its name honors golf course architect Alister MacKenzie. The club's site currently projects an early 2027 opening. A building has a very different release cycle from an app, a fact Rogenmoser has acknowledged in posts from the construction site.
He has brought in hospitality executive Casey Paulson as president and COO of Mackenzie Holdings. Rogenmoser described himself as a tech founder stepping into hospitality with much to learn. That admission fits the arc better than any claim that a successful founder can simply carry an old playbook into a new industry. Software offers quick revisions and near limitless distribution. A club needs construction, service, membership and a room people want to inhabit. The feedback arrives in how often they come back, whom they bring, and whether Tuesday afternoon feels worth the trip.
“Golf is the thread. Community is the point.”Dave Rogenmoser, on The Mackenzie Club
There is an economic irony here. Rogenmoser helped build a tool meant to help marketers produce more words, more quickly. His latest project asks people to spend an unhurried evening together. Yet both businesses began with a close observation of behavior. The ad-copy course revealed people struggling to complete an ordinary task. The golf club begins with another familiar problem: wanting more time to play, practice and see friends, without needing a full day and an outdoor course. The question is whether a physical place can turn that wish into a habit.
One of his recent construction updates described bringing prospective members into an unfinished floor for dinner. There were exposed ceilings and concrete, but he wrote that the room already felt like a club. He also reported passing 100 founding members. Those are his own early signals, not proof of what the finished venture will become. The building still has to open, the staff has to serve, and the members have to return. For a founder who once learned the cost of friendly but misleading feedback, that distinction is likely familiar.
What ties the chapters together is neither AI nor golf. It is the group that kept working together when the first plan failed, the users who showed a copywriting tool where to go, and the hope that a clubhouse can give people a reason to stay. The original founders' target of $6,000 a month was paired with a promise about friendship. Years later, the numbers became much larger and the business changed shape twice. The promise has proved rather more portable.