A bicycle is an unusually honest machine. If the chain slips, you notice. If the brakes stick, your legs receive the complaint. Long before Yves-Gabriel Leboeuf was building infrastructure for artificial intelligence, he was selling bicycles and parts. The machinery has become less visible since then. His interest in what prevents things from moving has survived.
Today, Leboeuf, often called YG, is the CEO and co-founder of Deck, a Montreal-founded company working on software that can operate other software. That description sounds abstract until you picture a perfectly ordinary afternoon spent signing into several websites to download several perfectly ordinary documents. Progress has furnished the office with remarkable computers. It has also furnished it with a remarkable number of passwords.
Leboeuf has built a career around the space between those two achievements. With Flinks, he helped applications connect to financial accounts. With Deck, he is pursuing work scattered across portals and applications that expect someone to sit down and click. His subject is the part of the digital economy that still needs a person to ferry things from one window to another.
The bicycle came before the bank
The early résumé is pleasingly tangible. Cycle Discount came first, followed by Moose Bicycle. There was also Walter Interactive, where Leboeuf was a founder and chief operating officer. Before the financial technology conferences, there were products a customer could ride home.
His educational record has its own detour: a general studies BA from the University of Saskatchewan in 2013, alongside computer science studies at Université du Québec en Outaouais that he did not complete. These are separate strands of a working life, rather than a tidy procession toward an inevitable company.
When he has described those beginnings, cycling supplies the straightforward explanation. He knew the activity, knew distributors, and started making deals. Entrepreneurship followed an interest he could do something with. The grand business identity could catch up later; there were bicycle parts to sell.
That is a useful detail about Leboeuf. His career can look, in retrospect, like a sequence of infrastructure theses. At the beginning, it included the much smaller act of recognizing something familiar enough to try. A bicycle shop and an API business have different inventories. Both require someone on the other side who wants what is being offered.
A company built around the connection
Before Flinks, Leboeuf worked as a technology consultant for lending companies, including on automating loan origination. It was a vantage point close to an unglamorous problem: a service could have a useful idea and still struggle to obtain the information needed to carry it out.
Flinks was incorporated in December 2016. Leboeuf, Frédérick Lavoie and Julien Cousineau built around connecting financial applications to consumers' banking information with their consent. The company went live in April 2017 and began generating revenue the following month. The elapsed time mattered to a founder who was trying to learn from an operating product.
In a 2018 conversation, Leboeuf described a business that had grown from three founders to 27 people. The work already included a question that tends to arrive once a product has customers: how a company should behave as more people join it. Culture had become something to build deliberately, alongside the technology.
There was little room for stately experimentation at the start. Recalling 2017, Leboeuf described having only three weeks of cash left. The team began posting its remaining cash and daily spending in Slack each morning. A spreadsheet may lack the romance of a founder's vision. It does have the courtesy of saying precisely how much time remains.
“Having competitors is fine. It's actually good”
Yves-Gabriel Leboeuf, Behind the Brand, 2024
Before incorporating Flinks, the founders sought letters of intent from potential customers. Leboeuf described asking whether they would use a reliable version of the proposed service, and what volume they might bring. Those conversations gave a proposed connection a prospective customer. It was an early test of demand before the company had much to show.
Flinks found backing. Luge Capital made the company its first investment, joining a 2018 seed financing alongside National Bank and other investors. The relationship between a startup building access to banking information and a bank supplying capital would become central to the next part of Leboeuf's career.
Flinks incorporated
National Bank's majority investment
Deck's public launch
The bank becomes a backer
In August 2021, National Bank announced a C$103 million investment in Flinks. The package included C$30 million in growth capital. The distinction is useful: some money bought existing shares, while some went into the business to support its expansion. The headline number alone cannot tell you what any individual founder took home.
For Leboeuf, the announced objective was broader reach across North America. Flinks had launched in the United States and wanted to expand its data connectivity and analytics offerings. A bank's involvement brought capital, expertise and relationships to a company whose product depended on moving information through a complicated financial landscape.
The arrangement also showed how many different jobs sit inside a connectivity company. Building the link is one. Persuading another organization to rely on it is another. Funding expansion adds a third set of conversations. The founder moves between these tasks, even when the product itself is supposed to become an unobtrusive part of somebody else's service.
His work also reached beyond customers and investors. Canadian lobbying records document Flinks advocating for an open banking legislative framework while he was its responsible officer. Conference appearances took him to audiences including the Paris Fintech Forum and Payments Canada Summit. These were different rooms for the same underlying conversation about access to financial information.
Eventually he returned to starting something. Lavoie returned with him. Their next venture would carry forward experience in connections and permissions, while looking beyond the bank account.
The electricity bill has entered the chat
Deck's 2024 introduction concentrated on utility data. Think of a business trying to collect water, energy or waste information across its operations. The records exist. Getting them together can mean visiting account after account and downloading them separately. It is a surprisingly clerical obstacle for a supposedly connected world.
Leboeuf and his colleagues saw room for a shared infrastructure layer. The October seed announcement brought US$4.5 million from investors including Golden Ventures, Better Tomorrow Ventures and Luge Capital. Familiar relationships helped a new company get moving. The founders initially planned to put the money into product development rather than immediately expand their 14-person team.
The scope widened. In April 2025, Deck announced a US$12 million Series A led by Infinity Ventures. Its own current company description reports US$25 million raised in total and names backers including Intact Ventures, along with angel investors Larry Fitzgerald and Rahul Mehta. The former football player makes an unexpected appearance in a story otherwise populated by account credentials.
One example makes the work legible. Evive needed retail sales information from nine retailer portals, each with its own access requirements. Deck describes bringing those feeds into its analytics pipeline automatically. The business value lies in information arriving when needed, without a fresh tour of the websites every time.
Repeat entrepreneurship has also produced a dispute. National Bank and Flinks sued Leboeuf and Lavoie in December 2025, alleging that Deck breached a non-compete agreement. In their January 2026 defence, the founders denied that Deck competed with Flinks and sought dismissal. The claims were untested in court when that exchange was reported. The disagreement puts a difficult question beside their familiar expertise: how far does one company's market extend into the next?
A clever answer still has to get through the door
By 2026, Leboeuf was describing Deck in terms of AI execution. His job includes company strategy and conversations with customers about putting agents to work. He points to a gap between what an AI system can demonstrate and what an organization can depend on repeatedly. A successful demonstration can end with applause. A working process has to run again tomorrow.
In one recollection, an agent encountered a problem it had not explicitly been programmed to handle, changed its approach and continued. Leboeuf found that recovery significant. The interesting moment was software dealing with an unexpected obstacle. It also raised the next question immediately: could such behavior become dependable?
He identifies pattern recognition, systems thinking and conviction as traits behind his work. His advice to other entrepreneurs is compact: “focus on friction rather than hype.” It is a fitting preference for someone whose companies spend so much time concerned with the part of a task that precedes the interesting part.
Deck's stated ambition is to let agents work within the applications businesses already use. That makes permissions and oversight part of the product, alongside navigation and retrieval. The current platform describes isolated sessions, action histories and human approval for sensitive operations. For software acting on someone else's behalf, getting in is only the beginning of the responsibility.
There is a useful modesty in judging the ambition at the level of a completed task. Did the document arrive? Can the next system read it? Was the action authorized? These small questions give an expansive technology story a scale that someone doing the work can recognize. The answer has to survive contact with the next account.
Leboeuf's path offers a practical way to look at that ambition. A bike business needed access to distributors and customers. Flinks needed connections between accounts and applications. Deck needs to make an authorized task travel across software that was built for human hands. The setting keeps changing. Somewhere in the middle, a chain still has to engage.