Every job Silka Hsu has held comes down to the same skill: get the right people in a room, then make something happen once they're there.

At seventeen, that meant producing a 500-person fashion show that raised more than $10,000 for charity. At Toronto Metropolitan University (then Ryerson), it meant running the university's TEDx program. After graduating, she joined Clearco, the Toronto fintech unicorn co-founded by Andrew D'Souza, where she worked alongside early-stage founders at the peak of the e-commerce boom. That job taught her something specific: capital and product matter, but one well-placed introduction can decide whether a company lives or dies.

Then came a chapter most people in tech would bury: wellness. Yoga teacher training. Retreats. Private events. She helped open the second Toronto location of Othership, the social-wellness brand, and it confirmed what Clearco had hinted at. Partnerships and events aren't marketing window dressing. They're how a business actually grows.

After Clearco, Andrew D'Souza started building something unusual. Boardy is a single AI character, one voice, one memory, one identity, that talks to an entire network and remembers every conversation. You can't customize him. His name, his accent, his personality are all fixed. That's the point.

While the rest of the market races to let users spin up private, disposable agents, Boardy goes the other direction. A single unchanging identity means trust earned with one person carries to the next. The whole network builds on one reputation. There is one Boardy. He remembers everything. And what he earns, he carries everywhere.

But the hardest problem with Boardy was never engineering. It was voice, judgment, and warmth. How do you teach one AI to talk to thousands of strangers and leave each one feeling genuinely known?

And that's where Silka came in.

She joined pre-seed, on a team of about ten, just before Boardy announced his $8M seed round led by Creandum. Her title was customer success, but Boardy was already talking to thousands of people, so the work quickly became something else entirely. She was shaping the entity: reporting bugs, refining prompts, tuning how Boardy held a conversation, deciding when he sounded right and when he didn't.

She's the first to say she joined without a technical background and figured it out on the job. That turned out to be exactly what the role needed. The person teaching Boardy how to connect with people had to actually be good at connecting with people.

From the outside, what came next looked like a string of pivots. The investor network, the deal partners, Boardy Ventures, the Boardy’s Talent Network. From the inside, it was all one plan, released piece by piece as the readiness and capital lined up.

Two weeks ago that growth became official. Boardy Pro launched, and it changes what Boardy is. He's no longer just a matchmaker. He's a deal partner.

The focus moves past the introduction to everything after it: deal flow, follow-ups, the outcomes that actually close. He joins meetings as a deal partner who remembers every prior call, so context never resets. After a meeting, you can text him, "write a proposal based on what AJ and I discussed," and he does. Morning briefs, recalled action items, continuity across every conversation. What started as a connector is now an ambient presence in the work.

Boardy serves the whole network at once. He's not one user's private assistant. He’s a single intelligence working on everyone's behalf, and that's what lets the memory and the goodwill compound instead of staying locked inside one person's account.

Ask Silka how Boardy approaches partnerships and the answer sounds almost countercultural for a venture-backed startup. The model is nearly all in-kind. No logo sponsorships, no pay-to-play. Find where two companies' goals genuinely overlap, then help both sides win, even when no money changes hands. Boardy has been free for most users for over two years. That's deliberate. His presence at Cannes Lions, HumanX, and HF0 is about expanding the network, not buying a stage.

The core skill, the one Silka honed across every stop on that non-linear path, is deceptively simple: find where two organizations' interests actually overlap, then help them win together. It is also the lesson she takes away from Boardy, the one Andrew D'Souza built into both the company and the entity. 

The more surface area of people you help, the more you gain, not less. Around here, we call that goodwill maxing.  It is the positive-sum principle The AI Collective is built on, and it is why this story belongs in our Hall of Fame.

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