Daren Trousdell and the business of the next move

Before Daren Trousdell was buying data businesses, he was losing interest in his fantasy football team. The upkeep had become a chore. Watching a game and trading predictions with friends was enjoyable; administering an imaginary roster required a different sort of devotion. In that small gap between pleasure and homework, he spotted a business.

OneUp Games began in 2011. An early experiment put Super Bowl Squares on Facebook. The team built it in fewer than five days, spent $400 on Facebook advertising and attracted thousands of users in a day. These were Trousdell’s reported results, an encouraging first test rather than a forecast. The idea was wonderfully ordinary: let people compete while the actual game was happening. Football already had enough people carrying clipboards.

Today, the Canadian entrepreneur is managing partner at KOAT Capital and executive chairman of Pelican.ai. He founded NowVertical Group and co-founded Clip Money. Those names place him in advertising, sports, banking and enterprise data, an itinerary that looks restless on a résumé. Look more closely and a recurring question emerges: where does a useful digital product become a business people will keep paying for?

Toronto, by way of a third-floor office

Trousdell grew up in Brantford, Ontario, playing and watching basketball, hockey and football. There were childhood ventures, too, including a paper route and a lemonade stand. He moved to Toronto before grade 11. Grocery and refrigerated-storage work supplied early lessons in teamwork; college studies in business and arts gave way to technology projects.

At Ecards.com, he sold brands on putting their logos into online greetings. When that business faltered, he began considering his own venture. He and a former colleague rented a third-floor office on Toronto’s John Street before settling on precisely what they would do. An advertising agency downstairs suggested a direction. Mindblossom followed in 2001. Location, in this case, contributed rather more than an address.

Aegis announced its acquisition of Mindblossom in November 2007. The agency supplied creative work, media planning, search marketing and website development. Its clients included Sirius and Home Depot. Digital advertising was becoming something large agency groups wanted to buy, and Trousdell had built a business they could absorb into an international network.

The distinction matters. A founder selling an agency also hands over client relationships, working methods and the people who make the promises deliverable. The buyer gets an organization as well as a name. Mindblossom joined Aegis Media Canada and the Isobar network. Trousdell subsequently worked in North American digital leadership, client strategy and corporate development. He had moved from building an agency to working inside a group that acquired them.

His geography changed, too. He is based in Palm Beach, Florida, while retaining his Toronto connection. As he put it when reflecting on his early years, “Toronto still feels like home to me.”

A game should not need a second job

OneUp returned him to the sports he had enjoyed as a boy, this time through the phone in a spectator’s hand. The early games were designed to let people join a live contest without having to master an entire league. A fan could play at home, in a bar or at the game. Familiar sporting events supplied the action; the software supplied another reason to care about the next play.

By 2014, OneUp Sports had partnerships with the NFL, MLB, NBA, NHL, PGA Tour and NASCAR, alongside individual teams. That breadth brought a different commercial problem into view. A sports organization could commission an app and treat it as another marketing expense. Trousdell wanted partners to consider the business that might sit behind the download.

“Mobile shouldn’t exist as a cost center.”

Daren Trousdell, discussing OneUp Sports in 2014

That was his argument to league and team partners: mobile deserved a revenue strategy and a lasting relationship with the fan. A second screen could do more than occupy the hand that was free of popcorn. It could connect an organization directly with the audience that made its rights, sponsors and merchandise valuable.

The progression from Mindblossom is easy to follow. Agency work had put him close to brands buying attention. Sports software put him close to organizations already commanding it. The commercial question shifted toward what those organizations could build around their audiences.

The platform argument, before the AI argument

In 2015, Trousdell took that thinking into publishing. Writing about the prospect of publishers placing content inside Facebook, he argued for developing their own platform capabilities. His concern was control: who held the audience relationship, the technology and the ability to assemble an advertising offer?

He described practical changes, including custom development, integration and sales teams equipped to sell more complicated products. A publisher would have to connect audience information with formats and placements. Counting impressions alone would leave too much of the opportunity unexplained.

It was an operator’s argument, with an acquisition-minded turn. Technology partnerships and audience arrangements could extend a company’s capabilities. “The best platforms are deal machines,” he wrote. The phrase gives a useful clue to his later career: he was already thinking about the business assembled around a product, and about how that assembly changed its value.

There is also a cost in that approach. More capabilities mean more work coordinating them. A platform needs people who can make its parts useful together. The elegance of the diagram is only the beginning of the assignment.

When the deal becomes the day job

NowVertical put acquisition at the center of the operating model. The company began trading on the TSX Venture Exchange on July 5, 2021, with Trousdell as chairman and CEO. Its business combined data software and services, organized around the needs of particular industries. The proposition depended on applying technology in settings where customers needed usable decisions.

By November that year, the group had acquired three software companies since listing. DocAuthority brought data-governance capabilities: cataloguing information, understanding its contents and tracking access. Affinio added audience insights and customer analytics. These purchases connected to different parts of a customer’s data problem, from knowing what information existed to understanding the relationships inside it.

Trousdell emphasized the customers, technology leaders and recurring software revenue each acquisition brought. This was familiar territory for someone whose earlier company had entered an agency network. Here, he was helping decide what to buy and how the purchases should fit together.

Acquisition creates a demanding second act. Buying a capability establishes ownership. Making it available across a group requires management attention, shared priorities and cooperation between teams. The work has a way of continuing after everyone has congratulated one another on the announcement.

Trousdell also co-founded Clip Money, a business banking network connecting a mobile application with physical deposit points. Cash handling sits some distance from social sports games, but it puts software against another everyday task. The physical part matters: a business with cash receipts still has to get that money into its banking system.

A founder becomes a shareholder

Trousdell resigned as NowVertical’s chair and CEO on May 30, 2023. Sasha Grujicic succeeded him as CEO; Sandeep Mendiratta took that role in January 2024. Trousdell remained a shareholder and publicly called for changes to the board. His relationship with the company had entered a more contentious phase.

The disagreement became legal as well as public. NowVertical obtained an injunction in January 2024, and the parties moved toward arbitration. On March 21, they announced a settlement of all outstanding disputes, including dismissal of ongoing proceedings, mutual releases, and voting and standstill provisions. The company also began a process to appoint an independent director acceptable to both sides.

The settlement restored a basis for cooperation. Trousdell welcomed the resolution and expressed support for Mendiratta’s contribution. It also marks an essential boundary in his biography. Founding a company, managing it and owning shares in it are different relationships. At NowVertical, his role had changed, even as his financial interest remained.

The next problem is on the invoice

In July 2024, KOAT Capital announced its acquisition of Pelican AI and its subsidiaries. Trousdell became executive chairman. Pelican’s business concerned payments and compliance technology for financial institutions, with an established operating history. The plans included market expansion, additions to management and generative AI in the product roadmap.

There were familiar connections. Grujicic joined the executive management team, while Pelican founder Parth Desai continued to lead its technology. The arrangement combined new ownership with people who knew the product. Trousdell’s position placed him alongside the operating business, with capital and governance responsibilities.

KOAT now describes a mandate spanning AI, infrastructure and enterprise technology across North America and Europe. Its team includes Jane Crowell and Grujicic, both names with ties to earlier parts of Trousdell’s career. Its stated approach gives portfolio businesses operating autonomy while the holding company participates in decisions about capital and leadership.

A more recent venture, Good Enough AI, brings him back to an immediate operating irritation. He has described portfolio businesses sending routine work to expensive AI models by default. The product he is promoting aims to route tasks to models suited to their requirements and cost. His stated ambition is predictable spending without paying for capabilities a particular task does not require.

Outside the product discussion, golf supplies another view of his working life. After a Hampton trip to Wisconsin, he wrote about the hours spent talking with fellow entrepreneurs on a course and watching how people handled setbacks. The appeal, in his telling, lay in uninterrupted conversation and the trust it could build.

The sports fan is still present. So is the founder looking at an activity and wondering where the unnecessary work has crept in. Fantasy football once supplied the irritation. Enterprise AI bills supply a newer one. Trousdell keeps returning to the point where an enthusiastic user encounters an awkward system - and starts considering the business that might make it less awkward.