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The nature of work and what it means to achieve your dream job is changing. In this series, we dive into some of the most aspirational jobs coveted by a new generation.

Pantonium CEO and Co-founder Remi Desa outside his Toronto office.Jessica Lee/Handout

When we think of iconic startup CEOs, names such as Zuckerberg, Gates or Musk come to mind. They are a few of the entrepreneurial legends who took visionary ideas – all in the technology sector – and turned them into transformative enterprises.

The romanticized version of that startup CEO experience is billion-dollar valuations, Bugattis and staggeringly large bank accounts. But the reality for the vast majority of early-stage business leaders, as Remi Desa would attest, is dramatically different.

Desa is the CEO and co-founder of Pantonium Inc., a Toronto-based transportation-management technology firm that helps municipalities turn route-based public transit buses into on-demand vehicles. In addition to his decade-long tenure at Pantonium, he has consulted and worked at other startups.

In Desa’s experience, the perceived glamour of building a business from the idea stage is exactly that – a perception.

“When we first got into the transportation space I was doing customer support, sales, billing,” Desa recalls. “We were just trying to survive, trying to get customers and trying to do something that was valuable to people.”

While Pantonium’s client list now boasts municipalities from across North America, the path from startup to the present was anything but linear.

The firm underwent three strategic pivots, at first focusing on patient emergency medical transportation, then offering their technology to original equipment manufacturers in the auto sector, before finding success with a focus on public transit.

The final shift generated revenue that allowed Pantonium to hire more experienced talent and make an aggressive push to acquire new customers, while attempting to attract venture capital funding.

“That’s one of the keys to the startup life,” Desa explains. “You have to be willing to accept the [market] feedback that you get.”

An appetite for being the boss

As the needs and desires of workers change, most prominently with Millennials and Generation Z, the aspirational jobs of these generations are also shifting. For example, young people are increasingly drawn to the idea of entrepreneurship. GoDaddy’s 2020 State of Entrepreneurship study found that nearly one in three U.S. millennials reported having a small business or side hustle. As well, 56 per cent of millennials in the study reported that entrepreneurship has always been a long-term goal, compared to 43 per cent of Generation X and 21 per cent of baby boomers.

Here in Canada, a 2019 BDC report found that the number of Canadians under 35 years old starting a business increased by 80 per cent between 2014 and 2018.

Remi Desa, in the Pantonium offices, says of his startup’s early days: “I was doing customer support, sales, billing. We were just trying to survive.”Jessica Lee/Handout

However, being a startup CEO is not an easy road to take. It can be lonely, exhausting and involve back-breaking responsibility. For most CEOs, days are spent bootstrapping, managing countless operational tasks and working in the business while desperately trying to work on it.

Most startup CEOs earn nothing in the early days of a business, or if they’re lucky, a relatively meagre five-figure salary that in no way reflects the 18-hour days that most of them log. Some invest their entire life savings in a venture and lose it all.

Ian Locke, the managing director of Linian Solutions – a management consulting firm that works with technology and venture-funded companies – is blunt in his assessment of the formidable barriers facing most startup CEOs.

“These people mortgage their homes, their capital and go through tough economic times. It’s a life, career and, in some cases, a family investment. You need a reality check as to what some of the obstacles can be,” Locke says.

“That said, if someone is truly passionate, as most of these folks are, and you can use your passion and your great idea, you can make it work.”

Focus, communication and thinking two steps ahead

While the age-old challenges of being your own boss remain, some aspects of the CEO experience have evolved, says Richard Blundell, an instructor at the University of Toronto’s Rotman School of Management and a consultant who has worked with several startups in the environmental technology field.

Blundell says that rapid technological development has pressed CEOs to figure out where their product, service or business model fits in today’s highly-connected, increasingly artificial intelligence-focused world. Not being tech-savvy is no longer an option.

“What’s also changed is this notion of understanding how important diversity is to a company,” Blundell notes. “The studies show the more diverse you are [as a company], the better decisions you make, the better you innovate and I think that has come into the role of CEO.”

Business leaders are also much more cognizant of their ability to make a social and environmental impact, according to Blundell. Companies can no longer just “trash the environment” without repercussions, he says, or ignore potential candidates because of bias. And investors are becoming increasingly enamoured by companies with a strong mission statement and a focus on solving societal and environmental ills.

What hasn’t changed, Blundell notes, is the need for CEOs to remain focused, to communicate their vision to everyone from their employees to clients, to excel at sales and to constantly think two steps ahead to deliver to their market’s expectations.

Ian Locke says that some new hurdles have emerged in the wake of the coronavirus pandemic. The shift to remote work has made it more challenging for CEOs to acquire talent and build effective teams, which is a key part of their role in the startup phase.

“Raising capital is also a challenge,” he says, noting that the venture capital environment in the U.S. tends to be more favourable than in Canada. “There are some great investors in the Series A and post-Series A financing area, but getting your first pre-Series A capital can be a real challenge.”

Despite these challenges, the allure of the startup fills a constant pipeline of dreamers and visionaries who are driven to build something that solves a problem or addresses one their target clientele didn’t know existed.

As Desa says, “Challenging is fun. If you look at it that way, it keeps life exciting. You’re constantly growing and improving.”