TORONTO & MONTREAL — The aisle of a Via Rail car stretches two and a half feet across and several dozen more in length, and on Tuesday this one was filled with sneakers. Above all those casually clad feet, founders and financiers drowned out the thrum of tech’s tough year with the sound of ideas. 

The Startup Train runs from Toronto’s Union Station to Montreal’s Gare Centrale in a scheduled five and a half hours, one chartered carriage in an otherwise ordinary train on an ordinary route. The 50-some passengers were headed to Startupfest, the three-day conference for early-stage firms starting Wednesday at the destination city’s Old Port. This year’s travelling troupe from Toronto is a post-pandemic revival, after lockdown cancellations. 

“I’m on the train to meet people,” said Azrah Manji-Savin, CEO of Toronto-based Syzl, who networked her way down the carriage, skipping on her first pass rows eight to 13, where travellers were at closest quarters. The Calgary-residing founder is on an eastern Canadian circuit to build up the business, a marketplace for cooks to rent professional kitchens short term. “We’re in a post-COVID world, and we want to get back to festivals.”

Tomisin Salam had started the day earlier than most, waking with the sun to get a lift in from near Vaughan, Ont., before traffic consumed the route to Union Station. FiatMatch, the remittance platform he founded in March 2021, also hosts how-to content for newcomers to Canada. His trip was about meeting potential partners who could contribute to the library of guides. “It puts their company out there in the hands of immigrants,” he said.

Many of the assembled founders were also there to scout potential funders, within the carriage or at the conference. Moien Giashi was on board to prospect the other way. The senior investment associate at Toronto’s GreenSky Ventures had already lined up Montreal meetings with Quebec-based startups as well as with incubators and accelerators. 

The tech downturn has flipped the dynamic of those investor-entrepreneur interactions. “Two years ago, we might even be trying to get a founder to talk to us—there were more funding opportunities for them,” he said. But dealmaking is down of late. “Companies are more distressed … so they want to make sure that they talk to as many investors as possible to see if they can find the required funding.” 

Some venture firms are using this year’s conference circuit simply to check in on their existing portfolios, but GreenSky is looking to put capital into new companies, following the $17-million first close of its fifth fund in February.

Distress was not on display in the carriage Tuesday, with the mood professionally upbeat even before the Via Rail workers brought out the first round of white wine at departure. “The early-stage market still has opportunities to raise funding, from my understanding and from people I’ve talked to,” said Ebenezer Seun Oyajumo, founder of BloomFi, which provides immigrant tenants with rent guarantees for landlords. The firm will shortly start shopping a $500,000 pre-seed round. 

Oyajumo is hoping to gain some gloss from the Startupfest stage, where he’ll compete for the $100,000 Black Entrepreneurship Investment Prize and Front Row Ventures’s $50,000 student award. The Startup Train’s riders included at least one recent pitch-competition winner: Manji-Savin, who took the trophy at Collision two weeks ago. (There were no outsized cheques at the Toronto conference—on stage, at least). 

At Startupfest, Manji-Savin will talk to potential investors as Syzl prepares to raise a round starting in September. The state of the market isn’t getting her down. As government pandemic loans come due, restaurants need the extra income that Syzl’s Airbnb-for-kitchens platform can provide. “What we’re doing, is very much—unfortunately or fortunately—aligned with what’s happening in the market today,” she said. 

Other passengers are finding their notions don’t fit the macro moment quite so well. Timothy Burgess is trying to raise the money to launch a consumer-facing crypto app. In 2023. “It’s brutal, to be frank,” he said. WealthAgile is a robo-advisor for tokens; Burgess calls it a “Robinhood for crypto.” (A Canadian platform of similar name and utility comes closer to mind.) 

WealthAgile began raising in December, just as the crypto titan FTX was coming off the rails. The startup quickly secured $200,000 in commitments for the half-million round, but this year has proved less successful. “So far, I haven’t got anybody to write a cheque,” said Burgess, a former hedge-fund guy. 

AI is to this year what crypto was to last. WealthAgile has proprietary automation, and it’s trying to ride the trend shift. “We recently rebalanced and changed our deck and we’ve revamped our website [to] show more AI,” Burgess said. And he left the coach with a lead, courtesy of a conversation with another founder: “Nigeria is a bigger crypto market than Canada, which I didn’t know before I got on this train,” Burgess said.

Six hours after climbing aboard, the passengers of the Startup Train disembarked in Montreal, joining a sea of ordinary people exiting other carriages into the summer heat. (They included, strikingly, a couple in linen safari suits and straw hats headed for Montreal’s tony Fairmont The Queen Elizabeth, as if to balance out all the casual startup energy). 

Amid clutches of travellers reuniting with waiting loved ones at Gare Centrale, groups of founders and funders huddled to enlist rideshares to local accelerator FounderFuel’s already-underway demo day. Just three days left to make that moment of startup serendipity.