Tooey Courtemanche

Founder & Chairman of the Board, Procore · 1 appearance on the record.

computed by AI from the episodes · how this works → · full disclaimer →

founderexecutive@tooeyprocore ↗LinkedIn ↗tooey.com ↗

Courtemanche founded Procore in 2002 after encountering communication and management challenges while building his own home in Santa Barbara. Over more than two decades, he scaled the cloud-based construction management software company into a publicly traded industry leader surpassing $1 billion in annual revenue.

36statements → 15claims → 10claims resolved → 50%fully supported → 4.25/5average certainty → 1.86/5average debate potential → 4.5/5argument clarity · the sources →

5 supported 4 partly supported 1 contradicted 5 not checkable as stated how the 15 claims stand · each chip opens the sources

15 assertions · 1 opinion · 11 insights · 5 disclosures · 4 what ifs · every statement was checked. The predictions and assertions are the 15 claims: statements the public record can support or contradict. 10 are resolved, and 5 name no date, number or outcome precise enough to check. Everything else (opinions, insights, what ifs, disclosures) can never be settled by the record, so it carries no assessment.

The record, in short

What the tape says about how Tooey argues and how the claims held up. Everything they said, and everything said about them, is in the tabs below.

Their most notable supported claim

Assertion Supported
Procore paused financial product development for a year to re-architect
“So we had actually had to stop developing that product at a certain point and go back and re architect it. So it was enterprise grade. And we literally stopped new future development for a year, but we realized that if we weren't going to, if we weren't going …”
Tooey Courtemanche Dec 4, 2023 ▶ 28:20 Tooey Courtemanche: From Construction Worker to Billionaire CEO | E1090 · 20VC with Harry Stebbings

Their most notable contradicted claim

Assertion Contradicted
Procore co-founder Steve Zahn took a previous company public in 13 months
“Steve Zahn, my co-founder, he had a company who took public before Procore. I think from founding to IPO, it was like 13 months, right?”
Tooey Courtemanche Dec 4, 2023 ▶ 8:39 Tooey Courtemanche: From Construction Worker to Billionaire CEO | E1090 · 20VC with Harry Stebbings

Expressed certainty vs assessment result

none yet certainty 1
none yet certainty 2
0% certainty 3
75% certainty 4
80% certainty 5

weighted support: a fully supported claim counts one, a partly supported claim counts half. Each filled bar is clickable and opens exactly those claims; "none yet" means nothing said at that certainty level has resolved yet

Argument clarity: do they answer the question? how? →

4.5 / 5 directness 4.8 · coherence 4.8 · precision 4.3 · compression 3.8

answered every one of 46 assessed questions directly

This is a score against a rubric. It is not a rank. Every host question → answer exchange is scored with names hidden on directness, coherence, precision and compression, 1–5 each, on meaning alone: disfluencies are ignored, and only raw unedited episodes count. This is the score that measures thought. Every scored exchange, scores shown → · The rubric and its checks →

How they sound: speaking style how? →

263 words/min while actually speaking · 25.1 um and uh per 1k words · 21.2 false starts per 1k · 32.4% of pauses land inside a clause

Measured by listening to the audio itself: 14,071 words across 1 episode of raw-level tape, transcribed verbatim with every um and uh kept, each one attributed only where the alignment onto our timed stream is unambiguous. These are measurements of speaking style. We do not rank them: across this corpus, fluency and argument quality are nearly uncorrelated (ρ≈0.2), and smooth talking does not signal clear thinking. How it's measured →

Everything Tooey Courtemanche said on 20VC that made the record, most notable first. Filter by type, assessment or year in the ledger →

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
Assertion Supported
Procore paused financial product development for a year to re-architect
“So we had actually had to stop developing that product at a certain point and go back and re architect it. So it was enterprise grade. And we literally stopped new future development for a year, but we realized that if we weren't going to, if we weren't going …”
Tooey Courtemanche Dec 4, 2023 ▶ 28:20 Tooey Courtemanche: From Construction Worker to Billionaire CEO | E1090 · 20VC with Harry Stebbings
Insight
Deploy customer success before sales teams when expanding internationally
“So what I suggest you do is that you actually deploy your customer success and your field and product marketing folks There first build that Brown, get the groundswell going with the referenceable customers, then put your go-to-market team in afterwards to cap…”
Tooey Courtemanche Dec 4, 2023 ▶ 32:08 Tooey Courtemanche: From Construction Worker to Billionaire CEO | E1090 · 20VC with Harry Stebbings
Insight
Hiring hungry, smart, unhumble people tanks company culture
“And trust me, I have hired a lot of hungry and smart people in this world. They tend to be assholes and they tend to not be good team players and they tend to tank culture.”
Tooey Courtemanche Dec 4, 2023 ▶ 45:16 Tooey Courtemanche: From Construction Worker to Billionaire CEO | E1090 · 20VC with Harry Stebbings
Disclosure
Procore avoids hiring from specific large tech companies due to culture
“We have definitely learned which large tech companies to not hire from. Cuz, cuz, you know, honestly, you can just go right back to the culture that is existent in those tech companies. And you're like, that's, you're basically hiring in that culture.”
Tooey Courtemanche Dec 4, 2023 ▶ 47:21 Tooey Courtemanche: From Construction Worker to Billionaire CEO | E1090 · 20VC with Harry Stebbings
Insight
Executives cannot excel as both a public CEO and a present parent
“I don't, there's not enough time in the day to be able to do both amazingly well.”
Tooey Courtemanche Dec 4, 2023 ▶ 1:06:12 Tooey Courtemanche: From Construction Worker to Billionaire CEO | E1090 · 20VC with Harry Stebbings
Assertion Supported
Courtemanche took out two mortgages and sold assets to fund payroll
“Myself and Steve's on my co-founder. We had to go without a paycheck, and I'll never forget, Harry, having to go home and tell my wife who by the way, at this point, we had sold everything that we had acquired in life. Like, I had, like, two mortgages on the h…”
Tooey Courtemanche Dec 4, 2023 ▶ 3:52 Tooey Courtemanche: From Construction Worker to Billionaire CEO | E1090 · 20VC with Harry Stebbings
Assertion Partly supported
Procore did not raise institutional venture capital until its 15th year
“We didn't really raise institutional money until like our 15th year.”
Tooey Courtemanche Dec 4, 2023 ▶ 6:00 Tooey Courtemanche: From Construction Worker to Billionaire CEO | E1090 · 20VC with Harry Stebbings
Insight
Founders survive by believing in an eventual nirvana state
“I think a lot of founders lie to themselves too, that there will be a nirvana state in the future where everything is, is going to be where you expect it to be. And I think that's just the survival instinct that we all have”
Tooey Courtemanche Dec 4, 2023 ▶ 9:40 Tooey Courtemanche: From Construction Worker to Billionaire CEO | E1090 · 20VC with Harry Stebbings
What-if
Courtemanche wishes Procore used closed-envelope fundraising to avoid VC manipulation
“I would have run probably a much more, you know, I listened to your discussion with Scott from Atlassian and how they did the closed envelope fundraising. And I'm like, I was thinking to myself, I wish we had done that because it would have taken a lot of this…”
Tooey Courtemanche Dec 4, 2023 ▶ 23:52 Tooey Courtemanche: From Construction Worker to Billionaire CEO | E1090 · 20VC with Harry Stebbings
Assertion Supported
Procore doubled its revenue four consecutive times leading up to 2017
“You know, it really started within about a year where we would double, and then double again, and double again. And so it really did, I mean, around 2017, we were rolling.”
Tooey Courtemanche Dec 4, 2023 ▶ 25:03 Tooey Courtemanche: From Construction Worker to Billionaire CEO | E1090 · 20VC with Harry Stebbings
Assertion Partly supported
Australian law penalizes construction CEOs with prison for undocumented site violations
“When we were selling in the Australia, New Zealand market they had these new laws in place in Australia around if a job site accident led to a death at a construction site and a safety violation had been seen prior to that that wasn't Document it. The CEO of t…”
Tooey Courtemanche Dec 4, 2023 ▶ 29:50 Tooey Courtemanche: From Construction Worker to Billionaire CEO | E1090 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Procore's volume-based pricing remains unpopular with some customers
“It was so wildly unpopular with our customers. Even till this day, some of our customers don't love it. But it is a, it's the ultimate yardstick, and we really believe in it.”
Tooey Courtemanche Dec 4, 2023 ▶ 34:54 Tooey Courtemanche: From Construction Worker to Billionaire CEO | E1090 · 20VC with Harry Stebbings
Insight
Baseline CEO stress does not diminish as a company grows
“All I'm saying is the baseline level of stress involved has not diminished at all.”
Tooey Courtemanche Dec 4, 2023 ▶ 43:26 Tooey Courtemanche: From Construction Worker to Billionaire CEO | E1090 · 20VC with Harry Stebbings
Disclosure
Courtemanche regrets hiring industry luminaries who lacked humility
“Yeah I've hired people again because I was, they were luminaries in our industry, and I said to myself, look, they may not be humble but they're gonna move the needle and I regretted I've regretted every single one of those decisions that I've made, and fortun…”
Tooey Courtemanche Dec 4, 2023 ▶ 46:09 Tooey Courtemanche: From Construction Worker to Billionaire CEO | E1090 · 20VC with Harry Stebbings
Insight
Procore employees must perform at target promotion levels before promotion
“Our message to them has always been, look, do the job as a senior director in the director role. And you will naturally get promoted into being a senior director. It's not something that's like granted to you. You don't get this because you asked for it. You g…”
Tooey Courtemanche Dec 4, 2023 ▶ 48:10 Tooey Courtemanche: From Construction Worker to Billionaire CEO | E1090 · 20VC with Harry Stebbings
Insight
Business resembles complex Legos where early errors mandate costly rollbacks
“If you get one piece wrong, and then you go 400 steps past it, you have to reverse all the way back to that step, get it right, and then go forward again. And I always think of it, it's like business, which is like, every step matters. And so, you have to be v…”
Tooey Courtemanche Dec 4, 2023 ▶ 1:07:42 Tooey Courtemanche: From Construction Worker to Billionaire CEO | E1090 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Courtemanche's wife attended under 10 company events in 21 years
“You would be surprised to know that I think Hillary has probably attended less than 10 Procore events in 21 years. She desperately tries to keep a firewall between our family and Procore, and that's her contribution to it, is when I get home, we don't talk abo…”
Tooey Courtemanche Dec 4, 2023 ▶ 1:09:48 Tooey Courtemanche: From Construction Worker to Billionaire CEO | E1090 · 20VC with Harry Stebbings
Insight
Courtemanche: Persistence mattered far more than skill for Procore's success
“Well, I would give skill probably the lowest ranking, the lowest because I would give persistence the highest percentage.”
Tooey Courtemanche Dec 4, 2023 ▶ 1:15:33 Tooey Courtemanche: From Construction Worker to Billionaire CEO | E1090 · 20VC with Harry Stebbings

Show 12statements(12 left)

Appearances (1)

EpisodeDateSpeaking time
Tooey Courtemanche: From Construction Worker to Billionaire CEO | E1090 · 20VC with Harry Dec 4, 2023 1h 1m
Made with StarZero

Turn any episode into a week of clips.

This entire site, over 1,200 episodes transcribed, diarized, checked and made playable, runs on the StarZero media pipeline. Drop in your own episode and the podcast clipper finds the moments worth sharing, cuts them, captions them, and reframes them for every feed.