How the son of the original ‘Iceman’ furthered his father’s legacy

Right after university graduation in 2011, Jake Silva put on his “investor glasses” for a Toronto ice-distribution business even though he didn’t have a financial stake in the company.

He had the fresh eyes of a younger generation that could bring new ideas and perspective to The Iceman, which his father John Silva had started 24 years earlier.

Jake saw a reputable company with steady demand, but also an operation that lacked structure and that had unrealized potential. Payroll would take days, clients still used paper invoices and filing cabinets were filled with physical records.

Jake decided to apply his degree in commerce and finance from Concordia University to the family business – involvement that would eventually fulfill expansion aspirations that John had always held but had never acted on.

However, transforming the regional ice distributor into a manufacturer with a production facility in Ontario and one in Alberta was a years-long process that required the founder to give up some power.

“I’m very hands-on,” John, 64, acknowledges. “I try to control stuff, and you can’t be like that” to grow.

The business moved away from having most decisions revolve around John, which had created bottlenecks. He is now much better at allowing departments to run their own teams, says Jake, who joined The Iceman full-time in 2012 and has been president since 2020. “I don’t think we would have grown as much as we have without him [ceding] some control.”

The founder of a business entering a new chapter must allow incoming leaders to “exercise real authority,” says Jill Renton, executive director of KPMG Canada’s family office. Succession is ideally a gradual transfer where the next generation proves their capability over time, she adds.

Transitioning The Iceman’s leadership is an example of such progression. Jake, now 37, grew up delivering bags of ice by golf cart each summer to bars, restaurants and events such as pride parades as well as running and car races. Once he joined permanently, he held a wide variety of roles throughout the enterprise.

When John’s business partner at the time wanted out in 2017, Jake, who was handling all accounting and finance matters, bought a stake. Until then, The Iceman was primarily a distributor, relying on an ice manufacturer that was also its competitor for product. “The dynamic was problematic,” Jake says, “because they could really control which kind of customers we could go after and which ones we couldn’t.”

He devised a business plan for The Iceman to build its own ice plant. His father was excited, Jake recalls, saying it’s something that John had always wanted to do, “but maybe he wasn’t able to put together all the pieces” when it came to financing and bank loans.

Jake secured the necessary funding and the company opened its first ice plant in 2018 in Vaughan, north of Toronto. The facility makes about 50 metric tonnes of ice daily but they’ve had to turn away clients in the last two years because of a lack of capacity. A second Toronto-area plant set to open early next year is expected to triple output.

Today, The Iceman supplies restaurants, events and businesses including Costco with cocktail cubes, packaged ice and dry ice, as well as heat-relief water bottles and freezers for construction sites. It also sells, rents and services ice machines. In 2024, it acquired an Edmonton company that produces and distributes ice across Alberta. The Iceman has grown to 80 employees in the summertime from around 30 when Jake first joined.

He also helped move the company toward software-based payroll, accounting, invoicing and dispatch systems. “If we had the old way of doing things, growing would have just been so painful,” Jake says.

John, who now manages The Iceman’s sales and customer relationships, appreciates his son’s leadership: “I see Jake’s done what he’s done and I’m very happy and lucky that he’s taken over.”

While Jake says he sometimes still seeks his father’s advice, “I’m already driving the bus, and he’s happy to have the role he’s in now.”

Ms. Renton notes that it’s important for a successor to understand the founder’s “unique qualities” that allowed the business to flourish in the first place. New leaders must treat their predecessors as “an important point of continuity,” she says.

John entered the industry in the mid-1970s when an ice plant in downtown Toronto closed and his parents’ nearby variety store became a local ice collection point. When restaurants asked if they could send taxis to the shop to retrieve bags of ice, John began delivering them himself in a pickup truck. He later bought a truck that doubled as both a delivery vehicle and storage for six pallets of ice and then expanded into dry ice and ice-machine rentals and repairs.

“I always learned how to hustle,” John says. However, in the early days, “I didn’t have the whole business plan together.”

The company’s profile got an unexpected boost this spring through a collaboration with the musical artist Drake, tied to the rollout of his 2026 album Iceman. After connecting through a mutual friend, the Canadian rapper and singer filmed video footage at The Iceman’s plant.

The attention sent millions of people to The Iceman’s website every day. “People pay a lot of money for a viral moment like that, so the fact that we were able to get it very coincidentally – it was great,” Jake says.

The Drake partnership sparked demand for The Iceman merchandise – previously only available to employees – such as jackets, hoodies and hats. Within two weeks of Drake’s single release, the company added an online store, selling more than 1,200 orders since, Jake says.

“It’s kind of cool to think that there’s people all over the world wearing Iceman T-shirts.”