Dec 4, 2023 · 1h 25m · news
Tooey Courtemanche: From Construction Worker to Billionaire CEO | E1090 · 20VC with Harry Stebbings
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
This interview explores the extraordinary 21-year journey of Tooey Courtemanche, from a college-dropout carpenter to the billionaire CEO of Procore, detailing the lessons of extreme market timing, values-based culture, and authentic leadership.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 22.2% of the talking time here. How this is scored →
Harry as informed peer 2.0 Guest teaching 2.3 Guest disagreement 1.0 Harry pushing back 1.9
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 33:27 Rejection of per-seat SaaS pricing model
Tooey forcefully rejects the standard SaaS per-seat pricing premise, arguing that seat-based licensing directly undermines collaboration on construction sites.
Hardest push from Harry ▶ 1:06:17 Refusal of earnings call priority over fatherhoodHarry directly challenges Tooey's work-life priorities, questioning why a seasoned CEO could not delegate earnings prep to attend a rare NFL game with his son.
Biggest teaching moment ▶ 11:54 Deconstruction of vertical SaaS market timing risksTooey systematically educates the VC host on why early construction SaaS adoption required five distinct technological and operational shifts to occur simultaneously.
Harry holds his own ▶ 44:37 Rejection of brilliant assholes in favor of humilityWhen Harry advocates for tolerating arrogant high-performers for financial gains, Tooey hits back with his 'hungry, humble, smart' framework and explains how non-humble stars ruin company culture.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Moving to Santa Barbara & The Origin of Procore | 0 | 0 | 0 | 0 | Warm opening conversation about Procore's origins. Harry asks friendly narrative questions about how Tooey's wife Hillary prompted the move to Santa Barbara and the founding of the company. | |
| Surviving the Great Financial Crisis & The Dark Years | 2 | 1 | 1 | 1 | Harry cites board members Will Griffith and Brian Feinstein regarding Procore almost going bust during the Great Financial Crisis. Tooey explains transitioning from custom home builders to commercial construction while missing paychecks. | |
| Tooey's Background: From Carpenter to Passionate Autodidact | 1 | 2 | 0 | 0 | Harry plays armchair psychologist asking what Tooey is running from and to. Tooey candidly shares his background as a carpenter who flunked out of school before discovering his passion. | |
| Market Timing: The 13-Year Wait & Surviving Competitors | 3 | 4 | 2 | 3 | Harry presses on why Procore took 13 years to reach significant revenue and expresses VC skepticism toward market timing risk. Tooey reframes the risk by detailing the five macro dependencies required for construction software adoption. | |
| The 2015 Inflection Point & The Mailbox Story | 2 | 1 | 0 | 1 | Harry asks what shifted at the 2015 inflection point. Tooey shares the mailbox story where his co-founder stopped needing to check daily mail for customer checks to make payroll. | |
| Sand Hill Road: Rejection, Idiots, and Finding the Right Partners | 1 | 2 | 1 | 0 | Tooey recounts being turned down on Sand Hill Road in 2008 when a VC suggested being more like Facebook and called them idiots, contrasted with VCs calling them geniuses years later. | |
| The Series A, VC Guilt Trips, and Hyper-Growth "Speed Wobbles" | 3 | 3 | 1 | 2 | Harry references venture dynamics and valuation models like Bessemer's early conservative caps. Tooey exposes emotional manipulation tactics used by VC partners during fundraising. | |
| Product Strategy: Scaling Multiple Product Lines Without Losing Focus | 2 | 3 | 0 | 1 | Harry asks how Procore expanded from one product to a suite of twelve without losing focus. Tooey explains prioritizing customer pain points and refactoring their financial product for enterprise scale. | |
| Playbook for International Expansion | 1 | 3 | 0 | 1 | Harry inquires about international expansion lessons based on board member prompts. Tooey explains why brand building and referenceable customer seeding must precede go-to-market scaling. | |
| The Contrarian Pricing Model: Volume-Based vs. Per-Seat | 3 | 4 | 2 | 2 | Harry asks about choosing volume-based pricing over standard SaaS per-seat pricing. Tooey firmly explains that construction is a team sport and seat licenses would restrict collaboration. | |
| The Evolution of Leadership: From Doing to Delegating | 2 | 3 | 1 | 2 | Tooey discusses transitioning from individual execution to delegation as CEO. Harry challenges with the classic founder dilemma of delegates not performing tasks as well as the founder. | |
| The Instagram vs. Reality of Being a CEO | 3 | 4 | 3 | 5 | Harry directly disagrees with Tooey's claim that being CEO does not get easier with scale, citing his own comforts like Fiji water and massages. Tooey counters by emphasizing the immense responsibility and blast radius of managing thousands of employees. | |
| Humility and Avoiding Superhero Hires in Scale | 3 | 3 | 2 | 4 | Harry challenges standard value-based hiring, arguing that egotistical high performers can be great for a business. Tooey counters with his 'hungry, humble, smart' rule and why culture destroyers are rejected. | |
| Scaling Leadership, Managing Incompetence, and Toby Lutke's Advice | 2 | 3 | 1 | 2 | Harry asks how to handle loyal employees who fail to scale with rapid growth. Tooey shares advice from Tobi Lütke about skill sets needing to scale faster than company growth rates. | |
| Imposter Syndrome, Stanford Vests, and Finding Authenticity | 1 | 2 | 0 | 1 | Tooey describes suffering imposter syndrome around Stanford-educated tech founders in fleece vests, until his wife urged him to embrace his authentic self as a former carpenter. | |
| Grounding Through the Slog: Walks in the Park vs. Calling Customers | 3 | 2 | 1 | 3 | Harry shares a personal grounding story and playfully teases Tooey for saying he calls customers when stressed instead of his wife. Tooey discusses capital allocation principles from 'The Outsiders'. | |
| The Isolation of Success and Tooey's Grounding 'Cabinet' | 2 | 2 | 1 | 2 | Harry notes how success isolates founders because people stop pushing back. Tooey details his trusted three-person 'cabinet' who tell him when his ideas are stupid. | |
| Frugality, Empathetic Parenting, and the Suitcase Story | 2 | 2 | 1 | 1 | Harry asks how to instill grit in children when raised in wealth. Tooey tells a story about his wife putting their son outside the front gate with a packed suitcase when he acted spoiled. | |
| Fatherhood Regrets, Earnings Calls, and Self-Wellness | 3 | 2 | 2 | 6 | Harry directly challenges Tooey on his work-life sacrifices, specifically pressing him on choosing earnings call prep over going to an NFL game with his son. | |
| Coping with Stress: Space, Introversion, and Complex Lego Sets | 2 | 2 | 1 | 2 | Tooey explains using complex Lego sets as an introverted coping mechanism to clear his mind. Harry offers a perspective that marriage is defined by persistence rather than happiness. | |
| Adversity, Generation Gaps, and the Decline of Workplace Resilience | 3 | 3 | 3 | 4 | Harry throws a provocative statement claiming younger workers are delicate 'petals'. Tooey offers a nuanced reframing around long economic expansion cycles and generational adversity. | |
| Disagreements with Steve and the Famous $100 Hat Fight | 1 | 1 | 1 | 1 | In a quickfire question, Tooey shares a story about a heated argument with his co-founder Steve Zom over spending $100 on branded hats at an early trade show. | |
| Emulating His Grandfather and Being the Family Underdog | 1 | 2 | 0 | 0 | Tooey gets emotional reflecting on his grandfather who ran a public bank, contrasting it with being the family underdog who was written off after dropping out of college. | |
| Bulldozers and Apple Watches: Tooey's Authentic Lavish Spends | 1 | 1 | 1 | 2 | Harry asks about Tooey's most lavish purchase. Tooey admits to buying a Caterpillar bulldozer for his ranch while continuing to drive an old beat-up Toyota Tundra. |
Statements from this episode (37)
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.”
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…”
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…”
Procore did not raise institutional venture capital until its 15th year
“We didn't really raise institutional money until like our 15th year.”
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?”
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”
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”
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?”
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.”
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…”
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…”
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…”
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.”
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.”
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 …”
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…”
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…”
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.”
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.”
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.”
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.”
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…”
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.”
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…”
Stebbings originally created 20VC for personal learning, not public release
“That's actually why I started it, by the way. I didn't actually intend to release them. People don't know that. Yeah, I just wanted to learn from great people and realize that it was the best way to people to give me time.”
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.”
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.…”
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…”
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.”
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…”
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…”
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…”
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.”
Microsoft CEO Satya Nadella mentors Procore CEO Tooey Courtemanche
“I have the fortunate privilege of having Satya be a mentor of mine, and I am absolutely fascinated by the complexity of that business, and how he makes sense out of it all.”
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.”
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.”
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.”
Shorts cut from this episode
▶ What makes a good founder? 🧠 · 20VC with Harry Stebbings (@6:57)
▶ "Don't Be an Entrepreneur, Do This . . ." 👇 Thoughts? · 20V (@59:23)
▶ How we use NASCAR tactics to win in business · 20VC with Har (@1:19:09)
▶ Leadership Advice I Got From Shopify CEO Tobi Lütke · 20VC w (@49:40)
▶ #1 Productivity Tip CEOs Need to Hear · 20VC with Harry Steb (@1:21:32)