Marco Pimentel Is Building a Bigger Surface Area for Luck

The useful part of Marco Pimentel’s first technology company was the part that failed. Around 2011, he had planned and funded a digital coupon startup in Victoria. The economics were not cooperating. While watching the runway shorten, he found a competitor that seemed to be doing better and sent its founder, Tobyn Sowden, an email. Pimentel proposed buying the company.

There was one flaw in the proposal: he could not afford it. The email still accomplished something. It led to coffee, then to Sowden acquiring Pimentel’s business, and finally to Pimentel joining him at Redbrick. What looked like an unsuccessful acquisition attempt became the opening move in a partnership that has lasted more than a decade.

Pimentel has a phrase for the logic behind that move: the “surface area of luck.” He makes room for small, unusual attempts because each one gives chance another place to land. It is an operator’s version of optimism. The experiment can disappoint and still leave behind a relationship, an insight or an unlocked door.

“Remember the surface area of luck.”Marco Pimentel

Learning the technology business from the business side

Pimentel says entrepreneurship showed up early. At ten or twelve, he was already running tiny businesses and enjoying the process. He studied business at the University of Victoria from 2001 to 2006, worked for several years with the Student Works management program, then moved through his coupon venture and a business-development role at North Studio.

He did not enter technology as an engineer. Around 2008, as new companies multiplied, he noticed that technically sophisticated founders still needed people who could explain a product, find customers and build partnerships. Business, communication and marketing were not supporting roles at a software company. They were part of the machinery that allowed the software to travel.

That observation became his route into Redbrick. Today, Pimentel is the Victoria company’s CMO and partner, connecting marketing and business objectives across a portfolio that includes products such as Shift, Leadpages, Animoto, Delivra and Paved. The title says marketing. The work described in Redbrick’s own evolution is broader: allocating attention, building shared systems and helping distinct companies operate without flattening their identities.

The accidental publisher

In 2015, Pimentel and Sowden had an idea for technology that could improve digital publishing. They co-founded Assembly, building systems that used reader behavior and large data sets to improve content discovery and advertising. The original ambition was a useful technology product. Then the product pulled its creators into publishing itself.

Pimentel later described the team as “accidental publishers.” In his account, Assembly grew 67,000 percent over five years and reached more than 25 million visitors a month. Its reach turned the experiment into one of the faster-growing digital publishing groups in North America. The lesson was not that the founders had predicted every step. It was that they recognized what the market had placed in front of them.

Assembly won a Digiday Media Award in 2020 for its use of audience insights. In April 2022, St. Joseph Communications announced that it would acquire the company and bring its 25-person team into a media network that includes Maclean’s, Chatelaine and Toronto Life. A tool designed to anticipate readers’ needs had found a home inside a large Canadian publisher.

When speed stops being the whole score

Redbrick’s own numbers once rewarded velocity. In 2016, it ranked fifth on the PROFIT 500 after reporting 8,214 percent revenue growth over five years. The portfolio kept changing. Redbrick bought established software businesses, and its central team had to support companies with their own leaders, products and working cultures.

The operating question changed with the scale. Pimentel has recalled asking whether Redbrick could build a durable company that would last. Durability requires profit, but also a design that keeps working when the original operators are no longer present in every decision. Leaders who had once touched everything had to give up familiar tasks and give newer leaders room to act.

“People think scale is just growth. But it’s really systems.”Marco Pimentel

This distinction is easy to miss from outside a growing company. Revenue can rise while the same small group repeatedly rescues the work. Headcount can multiply while decisions continue to queue at a founder’s desk. Systems show up when a good result becomes repeatable, responsibilities become clear and a portfolio company can retain its character while drawing on shared finance, people and marketing expertise.

Redbrick’s pursuit of B Corp certification gave the group another operating framework. Pimentel has said the process helped align the culture and ethics the company wanted to build around. By 2026, Redbrick had been named one of Canada’s Top Small and Medium Employers for seven consecutive years. The recognition matters less here as a trophy than as evidence of a longer shift: from asking how fast a business can move to asking what makes it worth keeping.

A second thesis, tested in public

Fly fishing runs quietly through Pimentel’s public life. He fishes the coastal waters of Western Canada, describes his skill level as amateur and shares the outdoors with his three children. Asked whom he would like to meet, he skipped the meal and chose a river with Patagonia founder Yvon Chouinard. The attraction was partly technique and partly Chouinard’s example of joining business, environmentalism and philanthropy.

Pimentel has been trying to make a similar connection with the tools he already knows. He founded Unless Ventures to invest in climate solutions and brands making fewer, more sustainable goods. He joined the board of The Narwhal, applying experience in digital publishing while supporting independent environmental journalism. At Redbrick, he has explored the digital carbon footprint of media and backed initiatives that connect students, technology and environmental research.

His most visible laboratory is The Capitalist Hippie. Launched in 2022 as Someone Like You, the podcast now has more than 90 episodes and a companion newsletter. Its title stages the tension instead of hiding it. Guests discuss wildfire drones, home electrification, food waste, alternative proteins, reused electric-vehicle batteries and climate finance. Pimentel keeps returning to the commercial mechanics: what the customer wants, how distribution works and where a technically sound solution can stall.

The through line reaches back to his entry into technology. A climate company also needs people who can translate an unfamiliar product, build demand, recruit a team and make a market. Pimentel’s message is practical: a person does not need to become a climate scientist or found a climate startup to lead on climate. Existing skills can be redirected from an existing seat.

That belief has moved into funding. Redbrick and portfolio company Shift offered a second $25,000 USD Impact Grant in 2026 for environmental innovations requiring technical solutions. The money was unrestricted. The structure placed a bet on the people closest to the problem, giving them room to change the plan when field conditions made the original budget obsolete.

The next useful opening

Pimentel’s current collection of roles can look eclectic: CMO, investor, host, news-board member, TEDx organizer and fly fisherman. The connection is the habit of building openings. A company gives products a launch pad. A podcast gives founders a microphone. A grant gives a small team discretion. A newsroom gives environmental facts public reach. A local stage gives an idea somewhere to begin.

There is restraint in his newer language about business. After the velocity of Redbrick’s early years and Assembly’s sudden rise, the words that recur are durable, systems, trust and leadership. They describe growth with a longer clock. They also leave space for the person doing the work to change. Pimentel’s advice is to stay open to that change because the priorities of twenty, thirty and later life will not remain fixed.

The failed coupon company is still the cleanest example. Its financial outcome did not become prettier with time. Its consequences became larger. One unreasonable note crossed a tiny gap between competitors, produced a coffee and rearranged a career. Pimentel still tries to create those gaps on purpose. The luck remains uncontrolled. Making more places for it to arrive is the work.