Before Joel Ronning won a sailing world championship, he and his crew made a list of things they were bad at. Then they put the worst ones at the top. There are more flattering ways to spend a day on the water. There are probably fewer useful ones.
The boat was Catapult, a J/70. The venue was San Francisco Bay. In preparation for the 2016 world championship, Ronning and his teammates went out early to catch light wind and stayed late for the heavier afternoon breeze. They tested speed and sails, repeated maneuvers and collected feedback. The routine had a compact name: “worst first.”
By then, Ronning had already spent nearly two decades running Digital River, the Minnesota company he founded to help businesses sell online. His public biography could have settled comfortably into the familiar furniture of an internet founder’s life: early idea, public company, industry awards. Instead, another scoreboard was waiting. Wind has little interest in a curriculum vitae.
The list nobody wants to write
Catapult’s preparation began with people. Ronning and trimmer Patrick Wilson had spent a couple of years trying different crew combinations, looking for skill and compatibility. For the Worlds, John Kostecki joined as tactician and mainsail trimmer, with Chris Stocke on the bow. Getting along was part of the selection process, alongside knowing what to do.
Their eventual victory can make that process sound inevitable. It was not. Earlier in 2016, at Key West, Ronning finished 11th in a 47-boat J/70 fleet. The results bounced around. A team hoping to win a long championship needed to become more consistent, and consistency offered rather less glamour than a spectacular afternoon.
In San Francisco, the team kept every counting finish inside the top ten. Across a twelve-race series, with a black-flag result discarded, that steadiness produced a 17-point winning margin. The fleet contained 68 boats from 15 nations. Catapult did not need to win every argument with the bay. It needed to keep answering the questions well enough.
“We ended up concluding that simple is faster.”
Joel Ronning, discussing Catapult’s preparation
That conclusion involved choosing sails that worked across conditions rather than ones that were excellent in a narrow range. Once a race began, the crew could not retune the rig. A forgiving setup reduced the penalty for being slightly wrong. It also let them look outside the boat. Being absorbed in one’s equipment is a poor way to notice everyone sailing past.
Software still needed a shop
Long before Catapult, Ronning had been working on another practical problem: how to move software from its maker to its buyer. He founded Digital River in February 1994. The internet offered a distribution channel, but a channel alone did not provide a working business. Somebody still had to accept the order, process payment and deliver the purchase.
His earlier ventures supplied relevant experience. Mirror Technologies, launched in 1985, sold storage devices for Apple Macintosh computers. Tech Squared, founded in 1990, operated in desktop-publishing catalogs. Ronning knew the business of selling computer products before he began replacing parts of its physical machinery with digital processes.
Digital River’s early relationship with Fujitsu helped bring the idea into existence. Its proposition was software distribution with the surrounding transaction handled too. The company’s first online sale through a client’s web store came in August 1996, more than two years after incorporation. Even an internet business had to spend time building the plumbing before anybody could turn on the tap.
The annual-report photograph is a useful corrective to the airy language of digital commerce. Ronning stands between cabinets and cables, smiling in a place that looks unmistakably physical. Downloads needed hardware. Transactions needed systems. A purchase might feel instantaneous to the customer because someone else had spent years arranging what happened underneath it.
Digital River’s service expanded across store development, hosting, fraud screening, customer support and marketing analysis. That made Ronning’s company part of other companies’ operations. The work was frequently hidden behind a client’s storefront. For the seller, the attraction was having fewer systems to build and manage. For Digital River, it meant making the same infrastructure useful to many businesses.
A public company meets rough weather
Digital River went public in August 1998. The following years supplied a lesson in how little a stock chart resembles an operating plan. Its offering price was $8.50. Within six months, the shares had climbed above $50; in January 2001, they fell to $2.1875. Owning internet infrastructure did not exempt a company from the internet’s financial weather.
Ronning’s answer included acquisitions. While weaker competitors struggled, Digital River bought businesses and assets that could bring customers onto its platform. In 2001, those deals included Net Sales assets, Calico Commerce’s marketplace division and Orbit Commerce. Buying customers still required the less theatrical work of supporting them and fitting their operations into the service.
The economics gradually changed. Digital River’s revenue rose from $14.5 million in 1999 to $101.2 million in 2003. The latter year brought $17.1 million in net income, following a small annual loss in 2002. These are company revenues and profits, rather than the total value of purchases passing through its systems. The distinction matters when a business earns its living handling other people’s sales.
Five years of reported revenue. Rounded to one decimal place.
His recognition included the 2000 Ernst & Young Entrepreneur of the Year award in e-business-to-business services and Minnesota’s 2001 Tekne Leadership Award. They mark the reception his work received at the time. The longer achievement was building an organization capable of doing the same complicated job for clients across borders, repeatedly.
Ronning stepped down as chief executive on November 1, 2012. He remained chairman until the end of that year. At the transition, Digital River described itself as a $400 million global cloud-commerce business. Eighteen years had passed since its founding. His departure gives this chapter a definite boundary; the company’s subsequent management and history belong to the years that followed.
The pleasure of a forgiving setup
On the racecourse, Ronning could describe his preferences in unusually concrete terms. He wanted a setup that was “mostly right” most of the time. He liked having the crew’s attention available for the race around them. The interesting part is the tradeoff: accepting a little imperfection in the equipment could improve the decisions made by the people using it.
There is a temptation to turn any successful sailor into a business parable. Ronning’s record is more interesting when the details are allowed to remain details. Crew compatibility, sail selection and repeated practice explain a sailing campaign. Hosting, customer support and transaction processing explain a commerce business. Both reward preparation, but neither can be run on a motivational poster.
Catapult kept racing after its world title. In January 2018, Ronning, Kostecki, Stocke and Wilson won a winter-series regatta in Tampa against a 53-boat fleet. All six of their finishes were in the top five. The winning margin was eleven points. Once again, the scorecard’s attraction was how little it wandered.
Ronning’s sailing also extended beyond the J/70. His Santa Cruz 70, also named Catapult, won overall and in class in California Offshore Race Week in 2017. A small keelboat and a 70-footer make different demands. The recurring boat name gives the results a family resemblance; the work on board changes considerably with the scale.
Back to the lake, onward to the factory
In May 2025, the championship came closer to home. Ronning won the J/70 U.S. National Championship on Lake Minnetonka with Victor Diaz de Leon, David Onan and Jessica Haverstock. Four races in heavy air on Saturday were followed by one on Sunday. Catapult won that final race and secured the title on familiar water.
“It was shifty, challenging and a lot of fun,” Ronning said. The remark is pleasingly free of corporate vocabulary. Local friends and fleet members made the occasion special to him. After international championships and unfamiliar venues, there was still pleasure in a difficult day on his own lake.
His business life continued too. As CEO of DATAMYTE, he was working in manufacturing technology when the company announced an AI addition to its Digital Clipboard platform in April 2025. DataMyteGPT was introduced to help users consult the company’s knowledge base for guidance and instructions. Ronning described it as a first phase of a broader deployment across the platform.
That work places him inside another set of operating details: collecting information, improving processes and helping people use software while doing their jobs. The setting has moved from the online shop to the factory. The practical question remains recognizable: what has to happen behind the scenes for the visible part to work?
In March 2026, Catapult won the Mixed-Plus division at the J/70 Midwinter Championship and finished fifth overall. Ronning sailed with Jeremy Wilmot, Giulia Conti, Stephanie Roble and Beccy Anderson. The competition involved 45 boats from ten countries. A world title from a decade earlier had become part of his record, while the next regatta still required a crew and a fresh set of decisions.
Perhaps that is the most revealing part of his story. Ronning has kept choosing activities in which experience helps without settling the outcome. Another customer has to be served. Another start has to be timed. And somewhere, before the pleasant business of doing what already works, there is a list with the worst thing written first.