The Ledger

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why aren't all 33 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 0 checkable ones are still open, waiting for their date. predictions held up or didn't; assertions are supported or contradicted. on every card: ▮▮▮▮▮ certainty · ▮▮▮▮▮ debate potential. speakers are clickable

Disclosure
Mitchell Green: Lead Edge Capital is buying public software stocks like Procore, Workday, Appian
“We are buyers. We're buying software stocks right now. You know, a portion of our funds can be invested in public equities, so we're buying companies like Procore, Workday, Appian.”
Mitchell Green Mar 7, 2026 ▶ 1:45 Mitchell Green: Why 50% of VCs Should Not Exist · 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
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
Insight
O'Driscoll: Initial startup growth rate only modestly correlates with long-term success
“There is a correlation, but it's modest between initial growth rate and overall outcomes and companies that have grown slowly at the start have been huge at the end. Procore was a slow grower and then became a huge outcome.”
Rory O'Driscoll Jul 2, 2026 ▶ 1:09:24 Coinbase Cuts AI Spend by 50% | Kalshi's $40B Valuation & Impending IPO | The Year for SaaS Roll-Ups · 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
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
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
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
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
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
Disclosure
Deeter: Bessemer owned 28% of Shopify and Twilio at IPO
“We own 28% of Shopify and Twilio at IPO and we owned, you know, well less than that of Procore and Service Titan just because we, you know, included a lot of other investors downstream.”
Byron Deeter Aug 25, 2025 ▶ 51:22 BVP Partner, Byron Deeter: The Future of Venture - Why Chanel vs Walmart is BS · 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
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
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 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
Willingness to return to carpentry saved Procore during hard times
“I think that's one of the reasons why we survived the hard times, is I just always believed that worst came to worst, I could go pick up a hammer, and I could go to work, and I could make, you know, an honest day's wages, and I would be fine.”
Tooey Courtemanche Dec 4, 2023 ▶ 1:22:19 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
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
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 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
What-if
Courtemanche attributes Procore's success to a five-minute task productivity habit
“And I swear Procore would not be where we are today if I didn't think about that every moment of my life.”
Tooey Courtemanche Dec 4, 2023 ▶ 1:21:47 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
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
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
Insight
CEOs need a trusted council of critics to ground them
“You live in a world where everyone tells you that every idea that you have is genius, right? Eventually your crazy, craziest ideas get acted upon. And they're not genius, right? So like, I love having this governor on me, which is, you know, this council of pe…”
Tooey Courtemanche Dec 4, 2023 ▶ 1:01:34 Tooey Courtemanche: From Construction Worker to Billionaire CEO | E1090 · 20VC with Harry Stebbings
Assertion Supported
Procore offered only one product until 2017
“Up until 2017 we only had one product. It was our project management tool, and it's still our flagship product.”
Tooey Courtemanche Dec 4, 2023 ▶ 27:26 Tooey Courtemanche: From Construction Worker to Billionaire CEO | E1090 · 20VC with Harry Stebbings
Insight
Courtemanche calls customers to reset his attitude on stressful days
“I call a customer. I honestly do. And there's nothing that gets me more excited and kind of, Grounded in the love of what I do than when I talk to a customer. So I literally do, I'll be like, I'm going to stop everything today and I'm going to call a customer.…”
Tooey Courtemanche Dec 4, 2023 ▶ 56:03 Tooey Courtemanche: From Construction Worker to Billionaire CEO | E1090 · 20VC with Harry Stebbings
Assertion Partly supported
Procore took 13 years to reach $9.6 million in revenue
“Between 2002 and 2015, we'd grown revenue from zero dollars to 9.6 million dollars, right?”
Tooey Courtemanche Dec 4, 2023 ▶ 14:58 Tooey Courtemanche: From Construction Worker to Billionaire CEO | E1090 · 20VC with Harry Stebbings
Assertion Partly supported
Tooey Courtemanche: Construction sites lacked internet and mobile tech in 2002
“If you were to invest in Procore in two, the internet was not at the job site. There was no such thing as mobile technology at all.”
Tooey Courtemanche Dec 4, 2023 ▶ 0:04 Tooey Courtemanche: From Construction Worker to Billionaire CEO | E1090 · 20VC with Harry Stebbings
Assertion Supported
Procore lost its primary customer base during the 2008 financial crisis
“We were selling our software to mostly custom home builders prior to the great financial crisis. And of course, the very first part of the construction industry that fell apart was the custom home business market. So we basically, our customers all went out of…”
Tooey Courtemanche Dec 4, 2023 ▶ 3:28 Tooey Courtemanche: From Construction Worker to Billionaire CEO | E1090 · 20VC with Harry Stebbings
Disclosure
Courtemanche spent two years miserable trying to fit Silicon Valley stereotypes
“I was miserable for probably two years where I would, like, I tried. I even went out and bought the Patagonia vest and, you know, Whatever. I just, like, I desperately want to figure this out.”
Tooey Courtemanche Dec 4, 2023 ▶ 53:24 Tooey Courtemanche: From Construction Worker to Billionaire CEO | E1090 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Courtemanche worked as a $15-per-hour construction worker before founding Procore
“I was working as a construction worker making 15 dollars an hour, you know, living in a tiny little apartment, and I, you know, I was not the one that was supposed to be the success in the family.”
Tooey Courtemanche Dec 4, 2023 ▶ 1:21:03 Tooey Courtemanche: From Construction Worker to Billionaire CEO | E1090 · 20VC with Harry Stebbings
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