Andrew D'Souza and the business of opening doors

Andrew D'Souza's team once gave him a gumball machine. The present was a comment on his working style: out came another idea, then another. For a founder, that can be a useful habit. For a company managing credit agreements across countries, it can also make for a rather lively Tuesday.

By the time he was describing the gift, D'Souza had already co-founded Clearco, served as its chief executive, moved to executive chair and started another company. His new venture, Boardy, makes professional introductions with AI. It has an Australian voice and a name that began with the idea of a helpful board member. The machine on his desk had acquired a conversational relative.

There is a connection between those two businesses, despite the change in scenery. Clearco offered entrepreneurs access to money without surrendering shares. Boardy offers access to people who might become investors, customers or colleagues. D'Souza keeps returning to the awkward interval between having something worth building and finding someone willing to help. His career has been spent trying to shorten it.

Before the term sheets, a paper route

He began earning money long before there was an investor presentation to rehearse. Born in India and raised in Mississauga, he grew up in a family that had immigrated to Canada. In his account of those years, buying CDs or going to the movies meant finding a way to pay for them. He persuaded the Mississauga News to let him start a paper route in a neighbourhood it was not serving.

There were other small jobs: lawns, dogs, deliveries. He later worked part time to save for university. At Waterloo, he studied Systems Design Engineering, graduating in 2008. He initially imagined designing cars. Co-op placements helped him discover that the automotive career he had pictured held less appeal when viewed close up. Consulting brought another discovery: he enjoyed strategy and wanted responsibility for the thing being built.

McKinsey was followed by startup work. At Top Prospect in Silicon Valley, he encountered the founders behind businesses that would become familiar names. What caught his attention was the surrounding infrastructure: investors, introductions and people prepared to tell a company's story. Geography came with privileges. A promising entrepreneur elsewhere could have the idea and still lack the invitation.

D'Souza's next jobs put him near the practical machinery of company building. At Top Hat, the classroom technology business, he worked on sales, marketing and raising capital, including opening its San Francisco office. He later became president of Nymi, which worked on wearable identity and security technology. Recruitment, partnerships and fundraising were part of his remit. He was learning how much of a company's progress happens through conversations.

The shopkeeper keeps the shares

Clearco began in 2015 as Clearbanc. Michele Romanow and D'Souza were the first people in the room; Romanow later described how Ivan Gritsiniak, Tanay Delima and Charlie Feng earned co-founder status through their contributions. The early search included tax software, faster payments for Uber drivers and financing for Airbnb hosts. The eventual e-commerce business emerged from experiments, rather than arriving fully dressed for its company photograph.

The proposition was easy to understand. An online shop might need money for advertising or inventory before the resulting sales arrived. Selling a permanent share of the business to cover that expense could be an expensive arrangement. Clearbanc examined operating data from platforms such as Stripe and Facebook, advanced capital and collected an agreed share of revenue until repayment reached its cap.

The attraction was ownership. In its 2018 offering, the company described funding without equity, personal guarantees or credit checks. The merchant could pay for growth while retaining the shares. There was still a cost, and the business still had to repay. But the arrangement gave entrepreneurs another choice beside a conventional loan or an equity cheque. A financing decision could begin with the shop's transactions, rather than the founder's performance across a conference table.

By November 2018, Clearbanc said it had funded more than $100 million in marketing capital for over 500 e-commerce brands that year. D'Souza was named to Canada's Top 40 Under 40 in 2020. The company became Clearco in 2021, the year its valuation reached $2 billion. SoftBank Vision Fund 2 put $215 million into a financing extension that July. By June 2022, its reported deployment exceeded $3.2 billion across roughly 7,000 firms.

The figures describe the scale of the experiment. They also explain why the founder's job changed. Supplying money means securing money, pricing it and keeping track of what happens when customers repay more slowly than expected. A clever offer brings people through the door. Running the institution behind it brings a different set of obligations.

An idea machine meets a credit agreement

In February 2022, Romanow became chief executive and D'Souza moved to executive chair. He said the decision was not imposed by the board. His planned work included strategy, fundraising, partnerships and executive recruitment. He had concluded that the operating role had changed with the company's size. The announcement was a recognition that the work required by a business can move away from the work that attracted its founder.

Another interest had been pulling at him. During his Clearco years, the company experimented with an AI coaching product called Clear Angel, using early access to GPT-3. D'Souza became absorbed in it. The project was shut down at the end of 2021 as the company concentrated on financing. Looking back, he described his enthusiasm for building with AI alongside his diminishing enthusiasm for the scaled lender's daily work.

“My team called it the gumball machine.”

Andrew D’Souza, recalling the gift that accompanied his stream of ideas

Clearco then faced a difficult period. Rising rates, slower e-commerce growth and tighter financing exposed the demands of its model. The company cut staff, withdrew from overseas markets and narrowed its product focus. Andrew Curtis succeeded Romanow as CEO in January 2023. Later that year, a $60 million Series D and a new asset-backed facility formed part of a recapitalization. The cheerful growth charts had acquired footnotes.

D'Souza left the executive-chair position at the end of 2023. His connection to the company continued: Clearco's current board page lists him as a co-founder and director. That distinction matters to his story. He had stopped running the business while remaining connected to what he helped create. The next question was what to build with the curiosity that had proved so useful, and sometimes so inconvenient, at Clearco.

An introduction with an Australian accent

Boardy was founded in 2024. Its founding group includes D'Souza, Matt Stein, Shen Sivananthan and brothers Ankur and Abhinav Boyed. In October, it announced a US$3 million pre-seed round. The early service invited people to speak to an AI about their work and the connections they needed. Boardy could then introduce them to other people it had spoken with. An address book had become a conversation.

That changed the starting point of networking. A profile can tell you someone's title. A conversation can reveal what they are trying to do this month, which problem is holding them up and why a meeting would be useful now. Boardy's wager is that listening to both sides produces a better introduction. The difficult part comes after the pleasant voice: each person needs a reason to take the call.

The investors encountered that proposition through the product itself. Creandum's Hanel Baveja brought Boardy to colleague Simon Schmincke's attention. He spoke with it, and the firm's partners tried it too. Schmincke described deciding they wanted to invest before seeing a deck or speaking to a human. In January 2025, Creandum led Boardy's US$8 million seed round. Other investors included Bonobos co-founder Andy Dunn and TaskRabbit founder Leah Solivan.

D'Souza described a Friday-to-Monday investment decision. The anecdote makes a memorable fundraising story, though its useful detail is more modest than a robot replacing a founder. The product gave prospective investors a direct experience of the service they were considering backing. Boardy demonstrated the route from conversation to relationship while the team raised money to develop it.

The meeting still belongs to the humans

The public product has since expanded beyond that first phone call. As of October 2026, Boardy's website describes matching requests, checking that an introduction suits both people, coordinating calendars and following up. It displays a company-reported count of more than 250,000 introductions. The count measures introductions; the more revealing question is what people do with the meetings that follow.

D'Souza has kept discussing those practical questions in public. In April 2026, he appeared with Golden Ventures talent partner Alison Kaizer at Uniting the Prairies in Saskatoon. Their conversation concerned hiring and how founders assess people as AI tools become part of everyday work. On his LinkedIn profile, he describes his purpose as “Creating things to make us happier and more connected.” It is a small sentence for a fairly large undertaking.

There is a pleasing tension in his choice of work. An entrepreneur who benefited from relationships is building a system intended to make useful relationships easier to find. He can automate the introduction and help arrange the appointment. The two people still have to arrive with something to say, listen carefully and decide whether to work together. Even an obliging AI cannot manufacture mutual interest by putting Tuesday at eleven in a calendar.

For D'Souza, the experiments keep changing while the preoccupation holds. A paper route found customers who were not being served. Clearco found merchants who needed a different financing offer. Boardy is looking for people whose next useful acquaintance is still outside their field of view. Somewhere between the gumball machine and the credit agreement, he has found another problem worth working on. The next conversation is already waiting.