John Ruffolo "The Decider" article in Sept/Oct 2018 edition of PIVOT

In many minds, John Ruffolo is already the most important person in the Canadian technology scene. Now he’s coming for the rest of the world. (Photographs by Daniel Ehrenworth)

Features | From Pivot Magazine

The decider

John Ruffolo, a CPA with an entrepreneurial itch, is bringing Canada’s once-dormant tech scene into the global limelight—one start-up at a time

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Every day, John Ruffolo walks past a graveyard of gadgets. Just beyond the entrance to his downtown Toronto investment firm, OMERS Ventures**, three glass panels shield a mini-museum of amusingly retro machines: a Super Pong IV console circa 1975, a Macintosh Classic computer from 1990, a dusty Palm Pilot. Next to a bulky Motorola DynaTAC, the first commercial cellphone, a placard reads, “Everyone wanted to be the first to get their hands on these awesomely unwieldy portable analogue brain-fryers.”

The geeky shrine is a reliable conversation piece for visitors and a welcome distraction for anxious entrepreneurs, many of whom have gazed at it moments before trying to convince Ruffolo, a 52-year-old CPA-turned-venture capitalist, to fund their supposedly world-changing start-up. But the gallery’s most important function is perhaps to serve as a daily reminder to Ruffolo and his two-dozen staff: today’s revolutionary technologies are tomorrow’s quaint junk. Any clever gizmo or app can get a company going; it takes a lot more—constant tinkering, organizational savvy, limitless passion—to build a successful business. As the CEO of OMERS Ventures, Ruffolo’s job is to find the most promising dreamers and give them what they need to end up less like Palm and more like Apple, a company that parlayed that clunky old Mac into a global dynasty.

As it happens, an ancient machine played a part in one of Ruffolo’s biggest deals. OMERS Ventures, which launched in 2011, narrowly missed the first two chances to invest in Shopify, the Ottawa-based online-retail giant. “Shopify was the one that got away,” he says. “We weren’t ready for them yet.” But Ruffolo hardly accepted his fate. He assigned a Ventures staffer to keep tabs on the company, stay in touch and make sure that when Shopify was looking for more funding, their firm was at the top of the list. “OMERS sent us this antique cash register, which we put in the lobby of our office,” says Russ Jones, who was Shopify’s CFO at the time. “Through all of our interactions with them, they became almost the de facto choice.” In 2013, Ruffolo met with Shopify CEO Tobias Lütke for what was supposed to be a 30-minute coffee; they ended up speaking for more than two hours, during which they agreed OMERS Ventures would lead the company’s next round of financing. Within a month, Ruffolo’s team had persuaded a handful of other venture capital firms to join them in investing a total of $100 million, then one of the largest rounds in Canadian tech history. Shopify, which now has a market cap of nearly $23 billion, has since become shorthand for national success. When discussing what Canada needs to do to rival Silicon Valley, entrepreneurs have a habit of saying, “We need more Shopifys.”

Earlier this year, OMERS Ventures announced it would open offices in Silicon Valley, London and Singapore, making it the first global venture capital firm based in Canada.

Most businesses court Ruffolo, not the other way around. He invests in fewer than one per cent of the companies that pitch him, but, for those lucky few, he provides a Midas touch. Yes, he chooses companies that are poised to succeed, but it’s equally true that they succeed because he chooses them. Through OMERS Ventures, he has invested $400 million in nearly 40 of Canada’s most promising companies, including the social media management platform Hootsuite, the online storytelling sensation Wattpad and the restaurant software company TouchBistro. Plenty more, including the fintech powerhouse Wealthsimple, have gone through OneEleven, an OMERS Ventures-backed accelerator that houses and scales mid-sized start-ups.

In Canada, there is a sense that everyone in the tech community plays for the same team. When one company wins, the whole country thrives: bright minds move here, massive companies set up shop here, foreign investors park their cash here. Ruffolo is the closest thing that team has to a coach. He may not get the glory of its most celebrated players (Shopify et al.), but his behind-the-scenes efforts are what prepare them for the big leagues. That goes far beyond cutting cheques. Ruffolo has the ear of government, which he’s used to lobby to secure funding for start-ups, help skilled tech workers migrate to Canada, and influence how entrepreneurs’ stock options are taxed. He sits on an almost comical number of corporate boards and advocacy councils. Most importantly, he believed in Canadian tech even after the dot-com crash and the 2008 financial crisis, when virtually every other bank, pension fund and venture capital firm stopped funding start-ups. And his success at OMERS Ventures has since persuaded them to start investing again. “He’s been a consummate champion for Canadian tech, and a courageous one at that,” says Ruffolo’s friend Jim Balsillie, the former co-CEO of Research In Motion (now Blackberry) and another CPA. “He just soldiers on.”

Earlier this year, OMERS Ventures announced it would open offices in Silicon Valley, London and Singapore, making it the first global venture capital firm based in Canada. The firm plans to invest $2 billion over the next decade in domestic and foreign companies. In many minds, Ruffolo is already the most important person in the Canadian technology scene. Now he’s coming for the rest of the world.

John Ruffolo as a teenagerA teenage John Ruffolo at the BMO branch (Courtesy of John Ruffolo)

Past the tech cemetery, the rest of the OMERS Ventures office straddles the line between buttoned-down Bay Street institution and start-up stereotype. Though the walls are austere and white, they house wellness rooms and a games nook with a Pac-Man arcade terminal, bubble hockey and foosball table. On a July afternoon, a TV in the lounge plays a World Cup game, but Ruffolo isn’t particularly interested—his team, Italy, didn’t qualify. Still, a miniature Azzurri jersey hangs on the glass wall of his office, where, on the off chance he’s not on the road or in a meeting, he spends his time at a standing desk. Behind him, a wall is lined with Raptors and Leafs paraphernalia, books and pictures. There’s one of John and his wife, Carryn, with whom he has two young children: a son, Caymus, named after their favourite California cabernet sauvignon, and a daughter, Rome, after John’s favourite city, which the family visits every year or two. Other photos show Ruffolo in far-flung locales with fellow members of Les Domestiques, a philanthropic cycling club that counts among its ranks TD Ameritrade head Tim Hockey, Purpose Investments CEO Som Seif, Mattamy Homes founder Peter Gilgan and Queen’s business school namesake Stephen Smith. Ruffolo’s affinity for the sport comes up often among those who know him, as does his penchant for blue jeans. Surrounded by friends-in-high-places portraits and shelves of awards, only the unfussy denim—described by a friend as Ruffolo’s badge of honour—hints at his working-class origins.

Ruffolo’s father arrived in Canada in 1955, a 17-year-old Italian with little money and a single suit. When he got off the boat, he was herded into a cattle train that took him to Toronto. He married another Italian and settled near Jane and Sheppard, an immigrant neighbourhood with a rough reputation but a strong Italian community, where neighbours walked between fenceless backyards to borrow tomatoes and zucchinis. “No one had any money,” says Ruffolo. “We all relied on each other.”

John, born Gianni, excelled at Catholic school, skipping an early grade and later becoming his high school’s valedictorian. During summers, when he begged to go to camp, his father, a house painter, put a brush in his hand and brought him to work. The province didn’t fund Catholic secondary schools at the time, so Ruffolo got a job at the local BMO branch to pay for his final three years. When he was 17, the bank extended its hours and promoted him to part-time manager, the youngest in company history. (Ruffolo’s mother, 73, is currently BMO’s oldest manager, at the same branch.) “When customers had a complaint, they’d say, ‘I want to speak to the manager,’ ” he says. “They’d call me and the customer would say, ‘No, I said the manager.’ ”

Ruffolo won a full-ride scholarship to York University’s Schulich School of Business, and intended to transition into investment banking at BMO. But at a career fair, his friends encouraged him to apply to Arthur Andersen, an accounting firm that sent its new recruits to Chicago for an orientation that doubled as an all-expenses-paid party. Ruffolo hand-wrote and submitted his resumé on the spot. In his interviews with BMO and Arthur Andersen, he asked his interviewers the same question: “How long until I’m in your position?” BMO told him 20 years; Arthur Andersen said nine. So Ruffolo chose accounting.

“When you have nothing left to lose, you take greater chances.”

Ruffolo earned his professional accounting designation in 1990, two years after joining Arthur Andersen. “I was surprised how much I liked the accounting firm,” he says. But he longed to go beyond taxes and balance sheets; he wanted to work with CEOs and understand, in minute detail, every aspect of their businesses. At 25, his only way in was to run Arthur Andersen’s high-tech practice, a nascent and unglamorous file where CEOs weren’t much older than Ruffolo. His first two clients were Microsoft and Oracle. “I got so much exposure to so many different industries and entrepreneurs,” he says. “I didn’t run a technology business and I wasn’t a venture capitalist, yet I felt I knew the space so well.” 

Several of Ruffolo’s colleagues say he developed a deep understanding of Canada’s technology sector thanks to his curiosity: “That’s interesting” is practically his catchphrase, and he’s unafraid to ask others to explain things to him. Gilgan, a friend and another professional accountant, credits part of Ruffolo’s business savvy to his early training and experience. “The beautiful thing about doing public accounting and auditing was witnessing someone else’s mistakes,” he says. “You get a million-dollar education that doesn’t cost a dime.” (At OMERS Ventures, Ruffolo currently employs a number of CPAs, who he says are passionate, flexible and inquisitive. “If you don’t have those underlying characteristics, you will fail, at least in our organization.”)

In 2001, when he was in his 30s, Ruffolo was one of the select few to make global partner at Arthur Andersen. “It was the biggest cheque I’ve ever cut in my life,” says Ruffolo of buying into the role. “Way bigger than the house I had just bought.” As it turned out, the timing was disastrous. Less than a month later, Enron, one of Arthur Andersen’s largest clients, was booked for keeping huge debts off its balance sheets, a scandal that led to the company’s eventual bankruptcy. Though Ruffolo wasn’t involved with the account, his position as a global partner made him potentially liable if Enron took Arthur Andersen down with it. That massive cheque, his accountant designation and his clients were all on the line, and he and other partners took a two-thirds salary cut to help pay the wages of the dissolving firm’s service staff. Cash-strapped, he was living in an apartment with no furniture and bracing for the worst. “You could see it,” he says. “The brand was done. We’d hit the iceberg.” Meanwhile, he had just begun dating Carryn, a marketing manager at Arthur Andersen (she left the firm and worked as an artist when the two became serious). “I remember telling him I was fine if we only ever ate food-court food,” she says. “That’s when I knew she was the right person for me,” says Ruffolo.

Then, as quickly as things collapsed, Ruffolo’s Job-like trial ended. After Enron declared bankruptcy, Arthur Andersen Canada merged with Deloitte, and, on a Monday morning in June 2002, he walked into his office to find everything changed: logos, business cards and desktop backgrounds had all been switched over the weekend. His phone rang, and an old client began talking to him about a deal as if nothing had happened. “It was like The Twilight Zone,” says Ruffolo. His designation, his partnership, his salary—they were all safe. “I think that was the moment in his career that he started taking bigger risks,” says Carryn. “When you have nothing left to lose, you take greater chances. And when you’re not driven by money, you make sound decisions.”

John Ruffolo and his wife, CarrynRuffolo cycling with his wife, Carryn (Courtesy of John Ruffolo)

Ruffolo escaped the Enron scandal intact, but the mid-2000s was a lousy time for Canadian tech. The dot-com bubble had burst, and unless you happened to run a company called Research In Motion, things looked bleak. Investors, whose tech returns had tanked over the past few years, had no appetite for risk. Venture capital invested in Canada dipped from its $6-billion peak in 2000 to $1.7 billion in 2005, and fell only further, to about $1 billion, after the 2008 financial crisis. “That was the bottom of the pit for venture capital, and there were zero signs of it resurrecting,” says Ruffolo. “Virtually all of the traditional players, particularly the pension funds and banks, said, ‘You know what? We’re tapping out.’”

Ruffolo had a first-row seat to the drought. At the time, he was leading Deloitte’s technology, media and telecommunications practice; running the firm’s Fast 50, a ranking of growing Canadian companies; and advising the CEOs of Rogers, OpenText and RIM. (It was conceivable they didn’t know Ruffolo was an accountant; to the chagrin of his employer, he didn’t mention it on his business card to avoid being pigeonholed.) He used the position to prod institutions—government, banks, pension funds—that he thought had a duty to re-stimulate the innovation sector, publicly criticizing them and proposing taxes on those that didn’t pitch in.

At least one pension fund was listening. Like most others, OMERS—the Ontario Municipal Employees Retirement System, which pays the pensions of the province’s local government employees—had ditched venture capital in 2008. But within a year or two, then-CEO Michael Nobrega, who had been Ruffolo’s boss at Arthur Andersen, was itching to get back to it. A CPA with an affinity for high tech, he frequently drove from Toronto to Waterloo on weeknights to meet with young start-up founders. When pension funds want to invest in entrepreneurs, they typically entrust the job to venture capital firms, reasoning that the sector’s deals are too small to merit their own staff and resources within the organization. (OMERS has $95 billion in assets, compared to Ventures’ $800 million, for example.) But Nobrega resolved to skip the middleman and create a wing of OMERS that would invest in start-ups directly.

Nobrega enlisted Ruffolo as an advisor on the project, but, within a few meetings, it was clear Nobrega wanted him to lead it. “Michael said to me, ‘You’ve been poking at this,’ ” says Ruffolo. “ ‘You think you’re so smart? Why don’t you do it?’ ” Ruffolo was torn. Would he really leave Deloitte, where he was building a promising career, to start a venture-capital firm at a time when tech investment was virtually nonexistent? He decided it would be hypocritical not to. “I’d been trying for five years to fix this, and I finally felt I had the opportunity to solve the problem from the inside once and for all.”

OMERS Ventures launched in 2011 to a chorus of confusion. “People said, ‘You’re an accountant. Who the hell do you think you are running a venture capital firm?’ ” recalls Ruffolo. Rival firms wanted him to fail, so that they could soak up OMERS’ tech money themselves. A number of OMERS executives wanted Ventures to die quickly, too; they saw it as Nobrega’s frivolous yet risky pet project. Others doubted there was anything worth investing in. “John took a lot of cheap shots,” says Balsillie. “A lot of people said he was overpaying, or that he was focusing too much on Canada.” Almost everyone seemed to be against the idea. “But the entrepreneurs?” says Ruffolo. “They all went, ‘This is awesome.’ ”

Within a decade, OMERS Ventures plans to triple its assets and open three new offices abroad, something no Canadian venture capital firm has ever done.

Here’s how to get a meeting with John Ruffolo: ask. He follows two rules: always agree to meet someone at least once (“It drives my assistant crazy”), and respond to all emails within 24 hours. I heard countless stories about Ruffolo’s preternatural emailing abilities—waking up to messages from John, receiving record-time responses from different time zones. “No email goes unanswered,” says Jim Orlando, Managing Partner at OMERS Ventures. “It’s as simple as that.”

Getting a hold of Ruffolo is easy. Impressing him is not. Out of 100 pitches, he might grant 10 a formal audience at the OMERS Ventures office. From there, just one—if any at all—will turn into an investment, and that’s only after a further series of meetings, not an impulsive Dragons’ Den-style handshake. To determine which one in 100 makes the cut, Ruffolo runs through a mental checklist. Is it a tech company that could one day exit or have an initial public offering? (He likes to tell the story of a misguided pitcher who asked him to invest in what he claimed were Toronto’s best rice balls.) Beyond that, is the idea realistic and doable? Does it address a significant issue for a sizable market? If the company is already generating revenue, can it scale? And most crucially, do the founders have the right stuff: curiosity, adaptability and tenacity?

The only way to find that out is by getting to know them. “There’s no shortcut,” says Ruffolo. “You have to spend a lot of time with them, understand their personalities and watch their interactions.” He considers their experience, gauges their reputation in the tech community (“Almost every time I get pitched, I already know of the person directly or indirectly”), and tries to pinpoint their motivation: do they have an insatiable desire to solve a problem—the kind of thing that will sustain them through all-nighters and turbulent patches—or just a get-rich-quick fantasy? Pitchers’ most common mistake, Ruffolo says, is revealing it’s the latter, by, for instance, dictating how long it will take for their company to exit and how much of a return Ventures will receive. “That’s an immediate X,” says Ruffolo. “First, thank you very much, but we’ll tell you what our internal rate of return is. Number two, that already tells me you’re in it for the money.”

When a start-up signs with Ventures, it exchanges company equity for a slice—anywhere from a few million to tens of millions—of the $800 million that Ventures manages on behalf of OMERS, the Big Banks, insurance companies and others. (These institutions pay the firm a small management fee but stand to hit the jackpot if a company in the Ventures portfolio gets acquired or successfully IPOs.) As one of Canada’s largest tech venture capital firms—alongside Toronto’s Georgian Partners and Montreal’s Novacap—Ventures also has significant institutional sway; it can persuade other venture capitalists, including larger American investors, to fund the companies it anoints, as it did during the Shopify deal. “U.S. venture capital firms put their nose up at some Canadian firms, like, ‘Why would you pick these guys?’ ” says Jones, the former Shopify CFO. “But I’ve found a lot of the U.S. firms have a lot of respect for both John and OMERs.”

Jones says Ventures was more supportive than other venture capital firms, too. “Some firms get cold feet,” he says. “They say, ‘We’ll give you the money, but it’s up to you to be successful.’ A lot of them talk about doing the heavy lifting, but in the case of OMERS we actually got the support we’d hoped for.” Ventures helped Shopify find office space and connect with advisors and experts. “When we invest in a business, we work for them,” says Orlando. “They tend to be young, tech-oriented entrepreneurs, so the work we do is roll-up-your-sleeves.”

A less obvious perk of winning over Ruffolo is access to his colossal Rolodex. It’s about to get a flurry of new pages thanks to OMERS Ventures’ expansion. Within a decade, the firm plans to triple its assets and open three new offices abroad, each with its own local team, something no Canadian venture capital firm has ever done. The first, in Silicon Valley, will give the firm a foothold in the mecca of high tech and allow it to invest in more American companies, many of which are exponentially larger than Canadian businesses. The second, in London, will be fully operational in 2019, with a third slated for Singapore. They will serve as bases of operations for expansion into Europe and Asia, which are experiencing tech booms to rival North America’s. At the same time, OneEleven, Ventures’ accelerator, is opening locations in cities including Boston and Berlin, both home to a heavy concentration of start-ups.

John Ruffolo in his officeRuffolo in his office (Courtesy of John Ruffolo)

Ruffolo made his name taking risks, but expansion may be his biggest gamble yet. OMERS Ventures is a giant in Canada, but abroad it will be a small fish in a giant pond. Ruffolo will need to compete with colossal American venture capital firms like Benchmark, Accel and Sequoia Capital—a California investor currently raising a record-setting US$8-billion fund—for the attention of both worthy start-ups and first-rate staff, who will be responsible for hand-picking foreign companies with the same rigour Ruffolo uses at home.

But if Ventures succeeds, the profits from these projects will flow back to Ontario, reversing a long-standing tradition of brilliant minds and ideas—and the money that stems from them—leaving Canada. Just as importantly, these international outposts will provide a valuable pathway for Canadian companies to reach the rest of the world, just as the country’s sector is blossoming. To Ruffolo, the global play is a natural next step. “How can I tell a company to scale up when I don’t do it myself?” 

Within a few years of its inception, OMERS Ventures had made believers out of doubtful OMERS execs and helped reignite the Canadian venture capital engine. “John was proven right,” says Balsillie. “Now, people are copying him.” Firms old and new began raising and investing amounts unseen since Y2K. (That trend has continued: Canadian venture capital surpassed $1.3 billion, a record high, in the first quarter of 2018.) Start-ups and accelerators sprouted across the country, and American tech Goliaths opened Canadian offices, creating thousands of jobs.

Still, there was a malaise in the tech community. In September 2015, Ruffolo invited the CEOs of the companies in the OMERS Ventures portfolio to the Drake, a trendy boutique hotel in west Toronto, to speak with Balsillie. They were concerned foreign multinationals would sideline the success of homegrown companies—how could a 20-person start-up in Vancouver, for example, compete with Microsoft for talent and attention? “When Amazon and Google are talking to the Canadian government three times a week,” says Balsillie, “do you think they’re asking, ‘How can I help Canadian tech companies do better?’ ” 

That month, Ruffolo and Balsillie founded the Council of Canadian Innovators, an advocacy group that would act as a single voice for Canadian start-ups. The group began formally lobbying ministers and MPs on causes raised by member CEOs, including government funding, stock-option taxation, fast-track visas for tech workers, and national intellectual-property and data strategies. (In 2017, the NDP asked the conflict of interest and ethics commissioner to investigate the Council for promising start-ups access to Liberal politicians in exchange for a $10,000 annual membership fee, but the commissioner found no examination was warranted.)* “For a year and a half, it was us knocking on government’s door,” says Ben Bergen, the Council’s executive director and a former campaign worker for Minister of Foreign Affairs Chrystia Freeland. “Now it’s reversed. In a number of areas, the government really wants to consult with us.” Ruffolo himself advised Navdeep Bains, the minister of Innovation, Science and Economic Development, on certain files, but he says his main role is to provide a forum where CEOs can lead the conversation. “True success will be when Jim and I fade off-screen and disappear.”

When I asked Ruffolo’s friends and colleagues to gauge his influence, they emphasized his knack for seeing both the forest and the trees. He can sic the Council on a nationwide project in the morning, then troubleshoot a 20-something entrepreneur’s software problems in the afternoon. “He’s capable of weed-crawling but also gliding at 30,000 feet,” says Gilgan. Mark McQueen, the president of CIBC Innovation Banking, says this puts Ruffolo in a unique position. “He can both fund companies and help government design programs that are relevant to the ecosystem as a whole.”

David Suzuki, a longtime friend, focused instead on Ruffolo’s steadfast commitment to the environment. Suzuki is accustomed to meeting with business leaders who give sustainability polite lip service, but after he spoke at a Deloitte clean-tech conference in 2005, he says Ruffolo was genuinely motivated to act. The two struck up an unlikely alliance: a free-market capitalist and left-leaning environmentalist, dining, fishing and debating with one another. Suzuki informed Ruffolo’s thinking on issues like carbon taxes and Indigenous involvement in fighting climate change, and Ruffolo became vice-chair of the David Suzuki Foundation, roping high-profile guests into charitable events and galas, which he attends in his trademark blue jeans. “He’s an enlightened entrepreneur,” says Suzuki. “If all the business community was like John, we’d be so far ahead on environmental issues.” 

“I don’t think John wants to be the top guy. There's too much bureaucracy and politics.”

On a brisk Tuesday morning this past April, Ruffolo took a seat onstage in a basement event space at MaRS, a labyrinthine complex of research labs and start-up offices in downtown Toronto. He was the odd man out on a panel of crypto currency geeks and blockchain boosters, gathered to launch Ether Capital on the NEO Exchange. (Relax, the majority of OMERS staff doesn’t fully understand that sentence either.) When the moderator addressed Ruffolo, he didn’t waste words: why would a risk-averse pension fund dive into the notoriously volatile world of crypto? “That’s a question a lot of people have asked me,” Ruffolo conceded. On the surface, it was an odd pairing. But, he continued, he thinks 10 to 15 years ahead—“self-driving cars, not flying cars,” as he put it. He was certain that the blockchain technologies undergirding crypto would soon transform modern life, and he wanted in. “I bet for tomorrow.” 

What does tomorrow hold for Ruffolo? Over the years, he has rebuffed lucrative offers to join companies preparing to IPO. “I don’t think he’d ever want to be the top guy, because there’s too much bureaucracy and politics,” says Carryn. “It would be frustrating for him not to be the one to stir things up… John is the renegade in a lot of the stuff he touches.” He’s routinely one step ahead of convention: Ventures invested in a handful of blockchain companies before most people had even heard the word, and Ruffolo sounded the alarm about data privacy long before the Cambridge Analytica scandal and Sidewalk Labs made it the topic du jour.

OMERS recently began asking Ruffolo to look into his crystal ball on investments beyond the Ventures file, too: agriculture, real estate, infrastructure, clean technology. “Every business is becoming a tech business. If tech can hijack taxis, it can hijack everything,” says Balsillie. “Once everybody wakes up to that, they’ll ask, who really understands it best?” At which point, he says, “John will become more of a visionary than a rebel.” 

Not that Ruffolo seems keen to abandon his rebellious streak. He says, if the opportunity arose, he wouldn’t be much interested in running OMERS, or in the politicking and administrating it would entail. “There are better people who really love that stuff,” he says. “That doesn’t turn my crank.” Ruffolo would much rather keep working with entrepreneurs. Keep building businesses. Keep chasing revolutionary ideas that might one day earn a hallowed place collecting dust behind a pane of glass.

(*This article has been updated to correct information about a complaint against the Council of Canadian Innovators.)

(**Update: On September 28, 2018, it was announced that John Ruffolo was leaving OMERS Ventures.)