Put yourself in James Lochrie’s shoes for a moment.

It’s 2015, and you’ve spent the past four years living in Toronto and growing the software venture you co-founded, Wave Financial, into a successful company. Now you’re taking a step back from daily operations at Wave and considering your next move. You could head anywhere in the world. Where do you go?

As the price of oil crashed, layoffs amassed and downtown offices emptied, Lochrie made the unlikely move of choosing Calgary. Where others saw gloom, he saw something different. “I looked at that situation and I said, ‘Those are the ingredients for mass success of the technology ecosystem right there,’” Lochrie remembers. “There was this massive opportunity.” And so he made a bet on Canada’s next tech boom happening in Calgary.

That go-against-the-grain mentality is characteristic of Lochrie, 53, co-founder and managing partner of Thin Air Labs, a venture capital and professional services firm that is all about helping early stage and globally scaling startups. He started and built Wave — which would go on to be acquired by H&R Block for $537 million — in the aftermath of the global financial crisis of 2008. When he visited Calgary in 2015, meeting and talking with local entrepreneurs, he saw parallels between his experiences and what Calgarians were building amid the energy crisis.

It helped, too, that he knew Calgary and what makes this place tick — having previously lived here from 2000 to 2011. “All doors are open here. It is a community that builds together,” he says.

Nearly a decade since Lochrie’s decision, the city’s tech and innovation sector is thriving — and Lochrie and Thin Air Labs are a key part of its success. According to the Canadian Venture Capital & Private Equity Association, in 2022 Alberta achieved a record high in venture capital activity for the fifth consecutive year, with $729 million across 85 deals, defying an industry-wide decline in investments. Though not quite at the heights achieved in 2022, activity remained strong in 2023, with $707 million invested across 86 deals.

And, as Lochrie sees it, the best is yet to come. “When I think about what’s coming over the next five years, we’re going to see incredibly explosive growth in the technology sector in Alberta,” he says. “And we want Thin Air Labs to be the leading firm that is going to be at the front and centre of the biggest and most important companies that the city is bringing to market.”

Lochrie’s path to entrepreneurship started when he was well into a successful career, though it was also ingrained in him from childhood. He grew up in Toronto, alongside an older sister and younger brother, with entrepreneurial parents who had emigrated from Scotland. Lochrie’s dad was a software engineer and his mom worked at a nursery school, and at one time they owned and ran a nursery school. “Having the background of that immigrant mentality, having to fight for it and work for it and not accept just what’s given to you … that was embedded in me at a young age,” he says.

As a kid, Lochrie loved games and competition — particularly winning. He learned to play card games, board games, chess and poker from his father. He played professional poker in his 20s and 30s and became a top-ranked poker player in Canada. He’s still a big gamer to this day, and says poker and chess have greatly shaped how he views building companies.

Lochrie’s parents expected him to go to university and get a degree, but he hated it and dropped out three times. He had an interest in and proficiency for accounting, however, and, at age 24, parlayed that into an entry-level job at the national firm FBC.

He climbed the company’s ranks, eventually moving to Calgary in 2000 to oversee the FBC technology team. As Lochrie came to understand accounting, small-business owners, technology and data, he saw an opportunity coming with the advent of cloud-based systems. Plus, by this time, he was feeling bored at his job. “I’m somebody that really likes to challenge myself,” he says. “I was just in this uncomfortable position of not having that challenge, and so I created it.”

In 2010, Lochrie partnered with his close friend, Kirk Simpson, to found Wave Accounting, a software firm offering services to small businesses. Lochrie was initially based in Calgary and travelled regularly to Toronto, where Simpson was located, but he soon moved his family to Toronto to grow Wave.

Lochrie and Simpson initially wanted to build a lifestyle business that would give them enough cash flow to do their jobs on a beach and go surfing. (“I’m not kidding,” he says.) But, when it became apparent that Wave’s potential was bigger, the company’s growth took a more aggressive path.

Lochrie served as Wave’s chief technology officer and later chief product officer, stepping aside from daily operations in 2015 — though remaining a strategic advisor and board member — when the business had transitioned to the execution stage (and Lochrie had again become bored and started seeking a new challenge). When Wave was acquired by H&R Block for $537 million in 2019, it marked one of the largest-ever Canadian tech exits at the time.

By then, Lochrie had returned to Calgary and was spending most of his time with other entrepreneurs. The atmosphere was so different than Toronto, he remembers, where he felt like he didn’t go to the right university and get the right degrees, or have a cottage in the right place. “When I was in Calgary, you could go and be talking to anybody at any time,” he says. “People were open to doing business and were interested in things and curious.”

Those conversations led Lochrie to angel investing and eventually to co-founding Thin Air Labs. His angel investments in four Calgary companies helped him refine the investment strategy that now guides Thin Air Labs, prioritizing founders and relationships.

Part-venture capital firm, part-professional services firm, Thin Air Labs is all about helping early stage startups scale globally. “We don’t want to just be known as a venture capital firm; we want to be known as a place where entrepreneurs come to create great companies in partnership with us,” says Lochrie.

Thin Air Labs publicly launched in January 2020, co-founded by Lochrie, Jim Gibson and Greg Hart, all veteran entrepreneurs who met through the local organization Rainforest Alberta (Gibson and Hart have since left). The name is a reference to the idiom “out of thin air,” and its pertinence to entrepreneurship. “We come up with things out of thin air. They’re ideas and they disappear into thin air if you don’t act on them,” Lochrie says. (The name is also a reference to Calgary’s high altitude.)

On the venture side, Thin Air Labs’ focus is growing Calgary’s tech sector. Calgary-based venture funds are rare; most firms with local offices are headquartered elsewhere in North America. Thin Air Labs’ Fund 1 closed in October 2023 with nearly $20 million secured, primarily from Alberta investors keen to make money by growing the Calgary economy. At the start of 2024, the fund had invested in 21 companies.

The services side is broader: Thin Air Labs works with more than 400 companies across North America per quarter, offering funding catalyst and product traction services. Staff have helped founders secure more than $30 million in grant funding, while a separate team supports entrepreneurs on product strategy, development and growth.

Like the startups it works with, Thin Air isn’t afraid to evolve. Early on, one priority was building a video-game ecosystem in Calgary, but Lochrie says the team recognized more significant opportunities in other sectors. Another pivot happened as a growing number of founders came looking for assistance beyond capital, leading to the development of the firm’s startup services.

Yet another change is the size of Fund 1. The initial goal of $100 million narrowed to $20 million. Lochrie says there were two main factors behind that adjustment: the shifting of general market conditions and the fact that investors outside of Calgary did not understand the investment opportunity the way local investors did. He won’t mince words about the challenges of raising money for early stage startups — explaining that there’s a misalignment between the startups and the risk-averse institutional investors that dominate the sector.

In the end, Lochrie says, they found incredible investors for Fund 1, all aligned around building great companies at-scale, keeping people in Calgary and growing a diversified economy. Besides high-net-worth individuals, significant contributors include locally based Sandstone Asset Management Inc., as well as The City of Calgary’s Opportunity Calgary Investment Fund, which contributed $4 million.

“When I think about what’s coming over the next five years, we’re going to see incredibly explosive growth in the technology sector in Alberta...” ---James Lochrie

As an investment firm, Lochrie describes Thin Air Labs’ distinguisher to be its focus on understanding the entrepreneur: who the person is, why they wake up in the morning, why they do what they do. That focus is partly a natural fit for Lochrie, an infinitely curious person, and partly a strategic decision. By truly knowing the entrepreneur, Thin Air Labs can have a more supportive relationship with them.

Such an approach is contrary to the common narrative surrounding venture capital, one of bold investments and spectacular returns. While the common narrative is for investors to expect a large portion of their portfolio to fail, Thin Air Labs believes all companies can win. As such, they plan and expect all companies to be successful, putting resources toward that success. “The true heart of what we do is really boring,” Lochrie says, invoking his accounting past. “We’re assessing the financial opportunity of businesses within markets.”

While the assessment side of things might be tedious, for Lochrie, the magic is on the people side, whether that’s picking companies or helping entrepreneurs solve problems. It’s a privilege, he says, to sit with people who have big ideas and act on them.

One such person is Alex Todorovic, CEO of Calgary-based Arbor, a data platform to help companies measure their emissions. Thin Air Labs has supported Arbor extensively, including investing in three of its funding rounds, helping Arbor secure grants through the funding-catalyst services and providing office space in Thin Air Labs’ downtown headquarters. “They’re incredible for working hands-on with founders,” Todorovic says of Thin Air Labs. “They’re very unique in their approach. I haven’t seen anybody else do it the way they do it.”

Todorovic says by working with Lochrie and his team, Arbor learned what it means to be a successful global company tackling a large-scale problem. That journey comes with many challenges — Todorovic likens being a founder to riding a roller coaster — but says Lochrie’s willingness to share his experience of entrepreneurship’s ups and downs has helped him greatly.

“As an investor, he is one-of-a-kind,” Todorovic says. “It’s not often you work with investors who have done the entire startup journey, from having an idea, grinding all the way through to getting acquired.”

Lochrie is intentionally open about his journey, including the personal cost of building a successful business. Looking back, he describes his leap to entrepreneurship as a selfish decision that had a major impact on those around him. He had three young kids and says walking away from a stable, well-paying job was challenging for his family.

“Whenever you do something big, and you have to sacrifice a lot to achieve those things, those sacrifices start to add up,” he says.

His public retelling of Wave’s success includes the broken relationships and the toll it took on his health, and he says he’s even more open when talking one-on-one with entrepreneurs. Why? Lochrie describes himself as outspoken and opinionated, and says he has become more transparent as he’s gotten older, believing young entrepreneurs can learn from his experiences. “I just don’t care what people think about me or the judgments they might have,” he says.

Besides his forthrightness, Lochrie offers founders a unique and bold perspective on how to think about their businesses, one that was heavily influenced by an early and influential investor in Wave, who told Lochrie and his co-founder there was no way they should sell their business for $100 million — that number was too low.

Wave was “just a little baby company” at the time, Lochrie says, so the comment left him floored. But, in that moment, a seed was planted in his head, shifting his perspective from thinking he was building something small to building something massive. Now, he does the same for others. Giving founders an idea of what is possible enables them to create something really magical, Lochrie says. “What I love about entrepreneurs is they truly create a future that doesn’t exist unless they do it,” he says.

“We wouldn’t have grown to the size that we’ve grown to as quickly — and I would have surely slept a lot less as a founder — if I didn’t have his [Lochrie's] support.” ---Vincent Ircandia, CEO and co-founder, StellarAlgo

Entrepreneur Vincent Ircandia has felt the push from Lochrie to think bigger and bolder. Ircandia is CEO and co-founder of StellarAlgo, a tech platform that helps sports and entertainment properties understand, grow and monetize their audiences, turning fans into customers. Ircandia first met Lochrie through a mutual friend, and Lochrie introduced Ircandia to two people who became StellarAlgo’s co-founders. A few years later, when the company first raised capital, Lochrie contributed as an angel investor.

Ircandia describes Lochrie as a supportive and empathetic leader who is also a visionary. “He’s been an exceptional resource and advisor for our company, from the early going,” Ircandia says. “We wouldn’t have grown to the size that we’ve grown to as quickly — and I would have surely slept a lot less as a founder — if I didn’t have his support.”

Lochrie envisions many more success stories like StellarAlgo in Calgary’s future, and says Thin Air Labs will continue to evolve to support those businesses. And he believes the potentially massive technology companies forming and growing here will one day redefine the city’s skyline.

“I really can’t wait to see what the story of Calgary looks like in 10 years,” Lochrie says. “It’s going to be spectacular.”

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Photos by Jared Sych