The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

20VC: From Construction Worker to Billionaire CEO; The 21-Year Epic Journey of Procore to an $8.6BN Company, Advice from Tobi at Shopify on Being a Great CEO & Why The Idea of "Becoming an Entrepreneur" is BS with Tooey Courtemanche

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Dec 4, 2023

Tooey Courtemanche, founder and CEO of Procore, shares his transformative journey from construction worker to leading a billion-dollar company. He discusses the initial struggles, including the 13 years it took to reach $9.6M in revenue and why many investors laughed at him in 2008. Tooey emphasizes the balance between vision and adaptability in entrepreneurship. He also delves into the art of leadership, the importance of cultural fit in hiring, and the complexities of managing both a thriving business and being a present parent.

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ANECDOTE

Procore's Origin Story

Tooey's wife, Hilary, prompted the idea for Procore after growing tired of his complaints about their house-building project in Santa Barbara.
Tooey was initially resistant to moving from Silicon Valley but eventually relented.

ANECDOTE

Near Bankruptcy During GFC

During the 2008 financial crisis, Procore almost went bankrupt, forcing Tooey and his co-founder to forgo salaries.
They sold personal assets and borrowed from family and friends to keep the company afloat.

INSIGHT

Founder's Conviction

A founder's unwavering belief in their mission is crucial, especially during challenging times.
Tooey's conviction that the construction industry would digitize kept him going despite early struggles.

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Tooey Courtemanche, Jr. is the Founder, CEO, President, and Chairman of the Board of Procore. He founded Procore in 2002 with a mission to connect everyone in construction on a global platform. After 13 years of business, the company had just $9.6M in revenue, 8 years after that they have over $890M in revenue. Under his leadership, Procore has grown to become a leading global provider of construction management software, connecting over 2 million users across 150+ countries. Today Procore trades on the New York Stock Exchange under the ticker PCOR. Huge thanks to Brian @ Bessemer and Will @ Iconiq for some amazing question suggestions today.

In Today's Episode with Tooey Courtemanche:

1. The Founding of a $8.5BN Company:

How did Tooey's wife, Hilary and their house-building lead to the idea for Procore?
What does Tooey know now that he wishes he had known when he started?
Did Tooey always know he would be a success? What was the moment of most doubt?

2. The 13-Year Journey to $9.6M in Revenue:

Why did it take so long to hit the $10M revenue mark? What changed in 2015?
What is Tooey's biggest advice to founders and investors who face market timing risk?
Why was Tooey laughed out of VC offices in 2008? What are his biggest pieces of advice to founders raising from VCs today?
How does Tooey advise founders on the balance between vision and sticking to a mission vs realising when it is not working and giving up?

3. The Art of Great CEOship:

What advice did Tobi @ Shopify give Tooey on being a great CEO? How did it impact his approach?
What are the biggest differences between the reality of being a CEO and the Instagram version?
What have been Tooey's biggest lessons on hiring? Why does hiring smart, ambitious but not humble people never work?
Why does Tooey believe the idea of "becoming an entrepreneur" to be BS?

4. Parenting, Money and Marriage:

Why does Tooey believe great parenting is like great CEOship?
How does one bring up children to be ambitious and humble in a very privileged upbringing?
What are the secrets to being there as a husband while also being a rockstar CEO?
How does Tooey reflect on his own relationship to money and wealth today?