There is no machine somewhere that cranks out successful entrepreneurs. While they all share some traits — energy, tenacity, and passion come to mind — they are all equally original, as unique as the products and ideas they bring to market. 

Those who receive the Venky Narayanamurti Entrepreneurial Leadership Award from the UC Santa Barbara College of Engineering demonstrate this singular nature. The award is conferred annually on an individual who has demonstrated success and leadership in the high-technology entrepreneurial community of the Central Coast. The word “individual” is key, and this year’s engagingly idiosyncratic winner, Craig “Tooey” Courtemanche, founder and CEO of Procore, a construction management software company headquartered in Carpinteria, California, is certainly no exception. For him, the first step to success is not to build a spread sheet or go on a number-crunching bender; it is, rather, to take a trip to the beach.

“If you have an idea, the first thing to do is to literally go sit on the beach for a few days and think about your strengths and weaknesses,” he says by way of advice to would-be entrepreneurs. “Examine who you are as a person, and don’t fool yourself.”

“On behalf of the UCSB College of Engineering, I offer sincere congratulations to Tooey Courtemanche for being named the recipient of the 2020 Venky Award,” said Dean Rod Alferness. “It takes immense courage, originality, and energy to accept the challenge of steering one’s startup into largely uncharted entrepreneurial waters. Dean Venky understood that, and Tooey Courtemanche embodies it.”

Courtemanche — his first name is the same as his father’s, so he became “Craig too,” which got turned into Tooey — first worked in construction and later became a software engineer. He founded Procore in 2002 and has since grown it to over two thousand employees operating out of fourteen offices around the world. More than 1 million construction projects have run on the Procore platform, which is used daily by more than 1.3 million people in over 125 countries. Courtemanche has been credited by Forbes with building the Cloud’s hottest technology “unicorn” by bringing software to low-tech construction sites.

“We were born in the cloud in 2002, something I’m really proud of,” he says. “The whole concept of Procore has always been to connect everybody in construction on a platform. There was no way we were going to do that if every client had to have a server.

“But I knew how to deploy a cloud server — an ASP server, as it was known back in the day — and I knew how to create multi-tenancy [so that multiple users could work off one server simultaneously] — and it was something I was kind of passionate about,” he continues. “It was a very new idea in the late nineties. I had seen it deployed in a company called Edify, and I thought, What a novel way to work. It was also way less expensive to buy one computer than to buy multiple servers and databases and everything else.”  

When the company began, Courtemanche and Procore president, Steve Zahm, employee number two, who has now been with him for fifteen years, would go to job sites to install internet Wi-Fi access points and routers so that the builders could use their software for $95 a month. Once, Courtemanche recalls, “After flying all the way to North Carolina to install a Wi-Fi router at a job site, Steve, who’s a Stanford graduate and got his MBA at Haas (business school at UC Berkeley), said to me, ‘Tooey, this business model is not going to scale.’

“I was summarily known at the time as being an idiot,” Courtemanche laughs. “Who builds collaboration software for an industry that doesn’t even have the internet? How is that even going to work?”

But then the iPhone and the iPad came out in 2007, and internet servers became common on job sites. “I went from being the idiot to being the genius,” he says. “The advantages of being connected on the network were suddenly apparent. The iPhone got the construction worker out of the job-site trailers, where they were plugging stuff into a laptop or a PC, and got them into the field, where they could use the platform to accelerate their job. Instead of logging data, they were actually collaborating with the data and using their device to get the job done. When we had twenty-three customers, we thought Procore would be this small business that we would use to do a cloud experiment. Looking back, we describe it as a business that went horribly right.”

Now, twenty years later, Courtemanche has received the prestigious Venky Entrepreneurship Award. “I am tremendously honored,” he said. “I’ve lived in Santa Barbara for twenty years and have watched this award go to people I admire and look up to. For a guy who is a college dropout to receive this award is kind of mind-blowing to me. It is really a special honor.” 

“All of us at Technology Management congratulate Tooey Courtemanche on his well-deserved recognition,” said Dave Adornetto, entrepreneurship program executive director for the UCSB TM program. “Tooey is the ultimate entrepreneur, whose vision and leadership enabled Procore to successfully navigate the uncertainties of disruptive technology and emerge as one of the fastest-growing and largest employers on the Central Coast. Under Tooey’s guidance, Procore has contributed significantly to the local entrepreneurial ecosystem and has become a major draw for our certificate and Master of Technology Management graduates.”

Courtemanche says that UCSB software engineers have been a key to Procore’s success. “People choose UCSB out of all the UC systems because of the quality of life they get there,” he explains. “You’re not in a city. You’re on the beach. You’re choosing that. We find that the people who come out of UCSB tend to be obviously highly educated and highly motivated, because they can’t get into the UC systems unless they’re highly motivated, but they also have some sort of interesting characteristics about them. They’re not just going for the diploma; they’re going for a well-rounded life, so we tend to get very well-rounded people from the program. I’ve seen it time and time again: some of the most interesting engineers we have working at Procore have come out of UCSB.”

Courtemanche sees passion as the most important element for anyone considering a startup. “I believe deeply in the fact that, as an entrepreneur, you have to be passionate, because you’re going to have more bad days than good ones, and if you don’t have that passion to get you out of bed and get going, you won’t make it.”

A near relative to passion for one’s idea is remaining true to one’s self. Courtemanche has been around the block on that one. “Five or six years ago, I found myself trying to emulate what a corporate CEO was like,” he says. “I thought, What are the characteristics of the archetypical tech CEO? I had met a lot of them in the Bay Area. They’re the professionals who are brought in when the company gets to a certain scale and the founder leaves. They are, by definition, usually white males who went to Stanford. They’re buttoned up. They’re in good shape. They tend to be taller than six-three. Their hair is perfectly coiffed and combed.

“I thought, If I’m not like this, no one’s going to take me seriously. So, I started dressing like them, with the Patagonia jacket, and I had the really short hair and all the other elements in place. And I had to show up and say the same stuff they say.” 

It didn’t last long. “The amount of effort it was taking to be somebody I wasn’t was literally destroying me, and I one day decided, I’m just going to be authentic, raw me, and people can take me or leave me. I’m not going to try to be somebody I’m not.  And the minute I stopped having all that cognitive dissonance, I was able to be free to spend all my time doing what I’m good at, which is to lead Procore. And people tell me all the time how they value my authenticity — the good, the bad, and the ugly. I’m never the smartest guy in the room, or the handsomest. I’m never the guy with the quickest comeback, but I am the guy who’s true to who he is, and people value that.”

Now that Procore is a global success, Courtemanche is often asked for advice. He tells would-be entrepreneurs that if their goal is to “be an entrepreneur,” they should reconsider. because being an entrepreneur is not the goal, but rather, what you do to accomplish the goal of bringing an idea to market. Other suggestions include, “Don’t assume you know all the answers or know what you’re doing; you don’t. Don’t be afraid of self-doubt; not everyone you see as a successful entrepreneur on TV was sure of themselves the whole way. Ask a lot of questions of many different people; I believe strongly in inquiry over advocacy. Raise enough money; no one ever raises enough money. Assume that it’s going to be harder and take longer than you would ever imagine.”

All of that, of course, follows that initial trip to the beach, where, he says, one should, “Examine who you are as a person. If your strengths are product, be the product CEO, and hire someone who’s going to be your operations partner. If you’re an operations person with a product idea, hire a product technical partner. If you look at all the great tech companies, there is always a partner, a foil. If you try to be everything to everybody, you’d won’t succeed. At the successful companies I know, the CEOs hire for their weaknesses.”

The Venky Narayanamurti Entrepreneurial Leadership Award is made possible through an endowment to the UCSB College of Engineering that honors former dean and professor Venkatesh ‘Venky’ Narayanamurti, whose tenure as dean was marked by his visionary leadership and enthusiastic support for the then-nascent local entrepreneurial economy. He worked diligently to infuse an entrepreneurial spirit into all aspects of the College of Engineering.