Insight certainty 4/5 debate potential 2/5

Baseline CEO stress does not diminish as a company grows

Tooey Courtemanche · Tooey Courtemanche: From Construction Worker to Billionaire CEO | E1090 · 20VC with Harry Stebbings · Dec 4, 2023 · at 43:26

Tooey Courtemanche, founder and CEO of Procore, discusses the reality of running a $9B public company versus public perceptions.

0:00 / 0:07exact quote · 7.6s
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“All I'm saying is the baseline level of stress involved has not diminished at all.”

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More from Tooey Courtemanche

Assertion Not checkable as stated
Bessemer capped Procore's upside potential at $300M in its Series A thesis
“So Bessemer, I don't know if Brian told you this, but Bessemer had an investment thesis on Procore that they, of course, they don't tell the company about. They thought that Procore the best outside scenario they could come up with was that Procore was going t…”
Tooey Courtemanche Dec 4, 2023 ▶ 22:07 Tooey Courtemanche: From Construction Worker to Billionaire CEO | E1090 · 20VC with Harry Stebbings
What-if
Courtemanche: Procore would never have succeeded with per-seat pricing
“I realized that I couldn't go with a per seat model because that was going to actually make it so we were never going to be successful.”
Tooey Courtemanche Dec 4, 2023 ▶ 34:16 Tooey Courtemanche: From Construction Worker to Billionaire CEO | E1090 · 20VC with Harry Stebbings
Opinion
Courtemanche: Modern workers lack resilience compared to World War II generation
“I honestly think that the reason that it was the greatest generation is they dealt with so much adversity And so much was on the line that they couldn't, they didn't have time to complain about there not being enough oat milk in the refrigerator in one of your…”
Tooey Courtemanche Dec 4, 2023 ▶ 1:14:14 Tooey Courtemanche: From Construction Worker to Billionaire CEO | E1090 · 20VC with Harry Stebbings
What-if
Procore survived 2008 because one investor kept injecting capital
“Honestly, if we didn't have the wherewithal to survive the great financial crisis thanks primarily to one of our investors who kept pumping money into Procore we wouldn't have survived”
Tooey Courtemanche Dec 4, 2023 ▶ 14:16 Tooey Courtemanche: From Construction Worker to Billionaire CEO | E1090 · 20VC with Harry Stebbings
Disclosure
Procore kept the exact same product for 13 years before market adoption
“We had not changed anything. We had been building the same product For 13 years but the market finally, you know, adopted it.”
Tooey Courtemanche Dec 4, 2023 ▶ 16:43 Tooey Courtemanche: From Construction Worker to Billionaire CEO | E1090 · 20VC with Harry Stebbings
Disclosure
Procore built unrelated $30k custom software projects to cover early payroll
“Customers would ask us to do custom development on a new application and, you know, if they're gonna pay us 30,000 dollars for a month's worth of work, we would literally Put two engineers on it and just ship a piece of software that had nothing to do with Pro…”
Tooey Courtemanche Dec 4, 2023 ▶ 17:18 Tooey Courtemanche: From Construction Worker to Billionaire CEO | E1090 · 20VC with Harry Stebbings
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