YouSaid · the spoken record

Tooey Courtemanche

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92
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2023-12-04
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2023-12-04
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  1. “And thank you very much. By the way, I feel like I've been having dinner with a great friend from last hour and sharing a bottle of wine. So I appreciate it. And thank you for putting up with me as well.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  2. “So I'm still only 56 years old. Let's assume they haven't put me out to pasture yet here at ProCore, but I would say at that point, you know, I am probably getting ready to think about retirement. Look, I've got this ranch that I love. I'm always building things. I just built a barn. I just built a deck. I just built some outbuildings. I'm building a western town up there with like a saloon and a jail and a bakery and all this other stuff. So I'm going to have my tool bags on. I'm going to be at my ranch and I'm going to be building something.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  3. “Her motto is you buy yourself something, I'm gonna buy myself something. So that's the way it works. So we're very open and transparent.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  4. “I may have just bought myself a decent watch for the very first time in my life. Actually, my son Henry, who kind of likes watches, he's the one who turned me on to this, but it's not a fancy fancy watch, but it's more than the Apple watch that I normally had worn.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  5. “I don't own a plane. By the way, I drive a five year old Toyota Tundra pickup truck that's all beat up and has a bent frame. And by the way, I don't do that because I'm trying to prove anything to anybody. I just do it because it kind of falls back into that authentic self. Like, I'm a construction worker. Like, there's just, I don't need all of that.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  6. “So, you know, I like construction and I own a ranch. And so I bought myself a caterpillar bulldozer. And I spend the weekends building roads and bulldozing things. And I love it.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  7. “I never doubted that I would be okay. I never in my wildest dreams believe that I would be where I am today. I would have never even given myself that latitude, but I always felt like I was going to be okay. And I think that's one of the reasons why we survived the hard times is I just always believe that worst came to worse I could go pick up a hammer and I could go to work and I could make an honest day's wages and I would be fine.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  8. “This seems kind of trite, but I was sitting in the front row of a class in college before I dropped out, and I was doodling on a piece of paper, and the professor walked up to me and she said to me, she said, hey, you want a piece of advice that will change your life forever? And I'm like, sure. She's like, when you have five minutes like you do right now, do a five minute job, tackle something. And I swear Procore would not be where we are today if I didn't think about that every moment of my life. If there's ever a moment of idle time, I find a way to fill it with something productive. And so therefore, I am highly productive all the time. And I honestly think it's been one of the best pieces of advice anybody's ever given me.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  9. “Like, literally, I was the kid in the family they had written off. You know, and in my family, once you graduated from college, which I did not do, you got a free trip to Europe with the family to celebrate your future success. You get all these privileges. Well, I didn't do that. So they literally had written me off. I was working as a construction worker making $15 an hour living in a tiny little apartment. I was not the one that was supposed to be the success in the family. So he's still, I think, relatively surprised by what's happened here”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  10. “My dad's father, my grandfather, is no longer with us. I would give anything to have a meal with him now that I've, it's funny, I'm getting a little choked up, but now that I've gotten to the point where I am in my career, he had taken his company public back in the 70s and he ran a very large bank and he was the CEO of it. I watched him and he was a role model of mine. And he always carried himself with such dignity and poise, but also authenticity. Like he treated the person who opened the door for him the same way that he treated his board members. So I would love to sit down with him and just kind of compare notes. Like, how would you grade me on my performance? And what can I learn still from you would be the biggest privilege in the world.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  11. “Keep it into a healthy perspective. I definitely think about our competition, but not very often. I think about our customers always. And we used to have a NASCAR at ProCore, which was a race car in the US. And we sponsored it. And one of our drivers once said, you know, the way I think about competition is you can either stare at them in the rearview mirror and lose the race, or you can stare forward at the finish line and win the race. And so I've always kind of taken that to heart, which is like, listen to your customers, do what's right, and you'll win. And you can just bet on the fact that your competition is not going to be doing it as well as you. So I don't really spend a lot of time thinking about them.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  12. “I would think it would be Microsoft because I had 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. Like I always think Procore is complicated. We have, you know, 11 products and we're, you know, whatever, 10 different countries and 16,000 customers. I don't know how you get your head around a $3 trillion business. And it's just, to me, it's fascinating. So I guess if they would give me the reins for the day, I think I would choose Microsoft.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  13. “Generally, it was resource allocation, and he was right, and I was wrong. Remember, I'm the kind of maverick product customer-centric one. I wanted to build, build, build, deliver, deliver, deliver, spend, spend, spend. Here's a great example. In the very early days, we went to a trade show and we had no money and we barely could afford to be there. And I think we were all sleeping in one hotel room in Las Vegas together, like on the floor. And we went to the floor of the trade show that day, and there was a booth where they were making branded hats. So I went over and I bought 10 Procor hats and I bought them back to the booth and it cost $100 Steve lit me up like I had just like tanked the business. He's like, we don't have $100. Like, what are you spending $100 on Procor branded hats to give away at our booth for? And we literally had like this like huge kind of knockdown dragout over the hundred dollars. So yeah, that was a tough conversation. And by the way, I still have one of those hats.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  14. “Starting Pro Core was one. What I had decided was I was going to wind down my other business and I was going to wind up ProCore. And that was not a rational decision. You know, I was making a lot of money and I was very successful and stable in my last business. So that was not one. I had a moment when I was transitioning from construction into technology where literally a family friend knocked on my front door. I had just quit my construction job. I didn't know what I was going to do and he offered me a job in technology. And I said yes. I knew nothing about technology, but he wanted to work with me and he wanted to mentor me. If I had not said yes that day standing in my front door in my house in Sausalito, California, I wouldn't be here today.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  15. “Okay, well, if you call that a skill, then yes. I would say skills, yes. I guess the lux side is, I consider myself to be very lucky. I think about moments in my life that had to have happened, literally like single moments in my life that had to have happened that got me to where we are today. And it scares the life out of me when I think about like if I had just done one thing differently at that point, like none of this would be true.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  16. “First and foremost, that if you do what you believe in and you're lucky, you can be successful. And I do believe that wholeheartedly. And I don't think a lot of people fully understand that, that you literally, anybody can be successful if they follow their passion and they have the amount of luck that's required in order for you to get there. You can be successful.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  17. “Yeah. And you know, you asked me before it gets any easier with Procore? It's the same thing with marriage, right? It doesn't get any easier. Things become different, but you still deal with challenges. Everybody does, and that's just, that's life. That's one of the things I think a lot about these days is that I think there's a perception that life should be stable and safe and predictable. People want that, right? But life is anything but that. Life is actually the complete opposite of that. And the more resilient you are and the more agile you are at dealing with adversity, ultimately the happier you are. So I think we have to dispel what the myth that we're all deserving of stability and safety and happiness in our lives because that's just not a natural state.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  18. “She forces me to. I've got a very, very strong willed wife. I don't have a lot of choice. I would not be able to survive if I didn't have her. I wouldn't be a good CEO of ProCore if I wasn't able to have her supporting me through this process, which essentially means giving me time and giving my space that I need to regroup and get kind of performant again. So let me tell you this, because it's like business. When I set out on starting ProCore, I kind of had this vision of like someday we're going to be done and everything's going to be a state of nirvana, right? Founders like to tell themselves that. When you get married and you're, you know, your early days, you're like, hey, you know, someday this is going to be perfect, right? Well, neither one of those stories is ever true, right? It's always a struggle and it's always a slog, but it's hopefully always a net positive that you actually benefit from. And fortunately for me, with my business and my wife, I've been extremely successful.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  19. “I love it. You would be surprised to know that I think Hillary has probably attended less than ten procorps in 21 years. She desperately tries to keep a firewall between our family and Procor, and that's her contribution to it. When I get home, we don't talk about Procore. We talk about the family. We talk about our relationship. We talk about our mutual...”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  20. “Hillary and I have been together. We dated before we got married, obviously, but we've been together for like 35, 36 years, something like that. We've been married for 25 years. We know each other really, really well, and we complement each other really well. She's a yoga instructor, right? And I'm a CEO of a public trader company. And we have very vastly different worlds outside of each other. And so we basically allow each other to have that space.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  21. “People will ask me, they'll judge my stress level if I'm building a Lego set or not. Right now I'm not building a Lego set. Just answer the next probable question. But that's.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  22. “If I'm really overwhelmed, fortunately for me, Hillary understands I'm an introvert. So for me, the very first thing I need to do is I need to get some alone time, right? So she will create lots of space for me to do my thing. One of the things that I do, which I'm very, I love, is I will build extremely complicated Lego sets. So when people ask me, like, that's weird. Why do you do that? Well, first I'm a builder. I like to build. And secondly, the thing with these complicated Lego sets is 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 as like business, which is like every step matters. And so you have to be very intentional. You have to be very focused. And that focus on that particular act of building these complex Lego sets allows me to stop thinking about ProCore for a finite period of time and allows me to kind of clear my brain. And it's something that just works for me.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  23. “That's a good point. By the way, these are the things I struggle with. Yeah, I'm sure I could have. I do try to prioritize my kind of self-stability and wellness first because if I'm not, I can't show up well. So that was part of my thing was I needed to get home, get a good night's rest. We had a huge week this week. And I didn't want to start behind the eight ball. But yes.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  24. “Yeah, well, like, here's a great example. He and I were in San Diego yesterday visiting my mom, his grandmother. We dropped him off on the way coming up north in LA. And he goes, hey, Dad, do you want to stop with me and go see the Charger game tonight? Football game. And I said, I would desperately love to do it, but I've got earnings this week and I can't do it. And just because I've got so much going on. And those are the tough, like even at this age, where he and our like best friends, I still have to make those really difficult decisions. And it breaks my heart, but like it's just what you have to do, I think. There's not enough time in the day to be able to do both amazingly well.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  25. “I would say my biggest regret, Harry, in life, is that I didn't do more. I wasn't there more. There are big swaths of his life where I was completely consumed by Procor. Fortunately for me, we have an amazing relationship and he and I are like best friends.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  26. “Very successful business at age 25, and I couldn't be more proud of them. Here's a great story. Henry at one point, he came home from his friend's house. He was like probably six, and he was being, he was kind of acting like his friend and like kind of being spoiled or whatever. So Hillary said to him, like, look, either you stop acting like your friend and you become Henry, or you can leave my house. And so he's like, no, I'm not going to do it. So you've got them all dressed up. She packed a suitcase. She pushed him outside the front gate of the house and shut the door behind. And he learned his lesson very, very quickly and then, you know, obviously led him back in at a certain point. But just being categorical in how you instill doing right and wrong and not having any leeway in how you apply it just it worked.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  27. “It was something I really worried about when Henry. I have one son, he's 25 now. When Henry was young, but Hillary and I looked at this a little bit different. So we have friends that, though they will fly around on a private jet, they want to drive a minivan because they want to show their kids that they're not that or something. We never played those games. We always believed that we would try to make Henry be the most empowered and responsible person we possibly could from day one. We talked to him like he was an adult from day one. And so we basically just said, look, you know, here are the guardrails. Do whatever you can within those guardrails. If you go outside those guardrails, all hell is going to break loose. And it did on several occasions. But within that, you have the latitude to do what you want as long as you're doing the right thing and you're not being an irresponsible person, right? And we are so fortunate that today Henry is one of the most well-adjusted. He's probably the most frugal member of our family. And he runs a...”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  28. “I had a very recent experience with a group of leaders at ProCor who all got together and it was a cocktail reception and I was walking around and having conversations with people and I felt like the entire time like people were like felt like they were on a job interview with me right it was like you know talking about what they've been working on and like you know while their work is more important than other work or whatever and I walk out and I actually called my wife on the way out I'm like I honestly value so much just direct real feedback remember i'm a carpenter by trade like i'm i'm not some high flute and ceo like i value the truth and i value kind of the input and you get less and less of that as you get more and more successful and so i keep a handful of people around there's three people that i call my cabinet right what is my wife hillary one is”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  29. “I don't really think about it that much, frankly. There's a lot of young people will come to me and say, I want to be an entrepreneur. And I'm like, that's not a thing. You don't become an entrepreneur. Like, you follow a passion and you build a business and you whatever, you know, so there's this kind of a mismatch between some people are like, I want to be like you because I want to be successful. And I'm like, that's not what I am. What I am is I'm somebody who's following a passion I'm delivering on the thing that makes me happiest in life. It's not about making money. So I actually don't spend a ton of time thinking about money, frankly. And that's probably a privilege I have.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  30. “Yeah, but that's why I don't really consider them regrets, right? Like they're, to me, they're an opportunity to learn. So we haven't made mistakes at the kind of esoteric, kind of the big level where all of a sudden it's we really, really screwed up. I've always been a firm believer. Again, this is actually my wife, which my wife always says the indecision is the decision, but I believe in the speed and the quality of decisions matters. So I'm much more willing to make a decision as long as the blast radius is small enough that I can live with it not working. So you can make lots of little decisions along the way and learn as you go without having to make these big decisions that actually can tank the business.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  31. “Yes, I am a huge believer. I don't know if you've read the book The Outsiders, but to me, that was an absolutely cathartic experience for me to actually understand that that is truly what, you know, one of the top four things a CEO has to do is be an efficient capital allocator. But really being judicious about how you allocate capital, it's not easy, but it's I'm the responsible party here. So I have to get it right.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  32. “You're like, oh, here comes I call a customer. I honestly do. And there's nothing that gets me more excited and 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. And it absolutely changes my attitude.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  33. “It's funny, I do this all the time, Harry, which is on my most challenging days when things are kind of stacking up and no good news is landing on my desk.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  34. “No, I'm kind of going through a phase of my life right now where I'm really doing a lot of introspection on what it all mean and who am I and all of that. So I don't think you ever truly know. But I think what you do know, again, is you know your strengths and your weaknesses and you know kind of at the core who you are as a person. And if you just stay true to those the things, I think you can deliver your authentic self every day and it's fine.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  35. “On that, because I really wanted to be myself. The interesting thing here is people responded wildly supportive. Like people loved seeing me be authentic and not be the try to be something I'm not. So it actually wasn't as scary as I thought it was going to be.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  36. “So, it's interesting. I'm going to bring this back to my wife, but I was miserable for probably two years. I tried. I even went out and bought the Patagonia vest and, you know, whatever. I just like, I'm like, I desperately want to figure this out. My wife said to me one day, she said, too, you know, on a personal basis, you're miserable. And I'm like, look, I don't know who I am and who I'm supposed to be. And she's like, that's not true. She goes, you know exactly who you are. And you know exactly who you should be. Stop trying to be somebody else. And so it was such a liberating feeling because I'm like, you know what? I'm my best when I'm authentic and I'm vulnerable, right? So, you know, I grew up my hair a little bit longer. Whatever. And I just started being me. And with all of my warts and all of the challenges of who I am, I just decided if I couldn't be my authentic self, I wasn't going to be happy. And honestly, if they didn't like me for being my authentic self and being vulnerable, they could fire me, right? But I was willing to kind of throw my badge down.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  37. “So remember, I'm the college dropout who's a carpenter, right? I was never supposed to be a publicly traded CEO of a successful tech company, right? That was not in the card. So as we grown ProCorum, we started hitting scale like around 2017 and 2018 and things started really flying along. I started being asked to go to these investor conferences in the Bay Area. And it was like the time was there. It was like this, there was a certain graduating class that was starting to go show up because they had a line of sight to an IPO. And I would sit there on these panels and every single one of the people on the panel would have their Patagonia zip up vest and they'd all gone to Stanford and they all were out of central casting. And here I am like a college dropout carpenter sitting on this panel going like what the hell do I know? That was kind of an existential crisis personally for me. I wasn't Frank Sloopman and I wasn't these other leaders that I looked up to just in terms of pedigree.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  38. “You just make the tough choice. You make the tough call. Now, fortunately, the way business works is that you don't wake up one day and realize that somebody's not scaling, right? You get all of the tails going up to it. You know, if there's a leader underneath me who's starting to kind of not scale to where we need them to go, you work with them on scaling, but at a certain point you start having conversations around like, let's find a place in the organization where you can actually be successful. And then if that doesn't work, then you, with all empathy in the world, you walk them out the door and you help them find another job somewhere else. And that's the path that it can go.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  39. “That might be the best thing I've heard in a long time. But he said to me, this was probably 10 years ago. He said to me, Tewie, what's important about leadership is if your business is scaling at 100% a year, that means you and your team needs to be scaling their skill set at greater than 100% a year. I took that to heart, which is I look very critically across my leadership team to make sure that my team has what it takes to take us to the next level, not rewarding them for getting us to where we came from. So I spend a lot of time having those conversations with folks saying that like, look, there's probably somebody outside of this organization that might be able to do this job where you can learn from them and scale your own career. It's never easy.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  40. “It's such a broad subject because for 21 years, have had to make very difficult personnel decisions. One of my very old mentor of mine, Toby Lutke, as I'm sure you know from Shop”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  41. “Yeah. By the way, we have a saying at ProCorus Don't be a problem spotter, be a problem solver. You know, you've come to me with a problem and not a solution, and I'm going to march you right out of my office. Like, I don't want to hear about the problems until you have, you know, the solution at hand.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  42. “It's not that, but you know what? If you empower your boss by actually helping them do their job effectively, and it's not just about checking the box and doing your nine to five job, you are much more apt to be promoted than if you just check the box.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  43. “You know, the inverse, which is really interesting, is that Procore, people will come to us and say, I want to be a senior director, I'm a director. I want to be a senior director. You know, what do I need to do? Our message to them has always been 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 granted to you. You don't get this because you ask for it. You get it because you actually do the work and earn it.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  44. “We have definitely learned which large tech companies to not hire from because, you know, honestly, you can just go right back to the culture that is existent in those tech companies. And you're like, you're basically hiring in that culture. And if it's toxic.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  45. “Yeah, I've hired people again because they were luminaries in our industry. And I said to myself, look, they may not be humble, but they're going to move the needle. I've regretted every single one of those decisions that I've made, and fortunately I'm not making those decisions any longer. But yeah, those were hard lessons learned because at some point, you know, you really have to get real and say no to people that might have a big impact on the business, but you just know are not going to be a cultural fit. And at our scale, Harry, there's no longer a superhero a procure who's going to move the needle, right? The only way you move the needle at Procore is you work collaboratively across teams in ways that are inclusive and basically brings the highest level of capabilities out of people in order to deliver big results. And you can't do that if you are kind of selfish and you're an individual contributor who all you want to do is root for your own success. It just doesn't work.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  46. “So, the value hiring is one piece of it. The way we solve for that is Hungry Humble Smart. We will not hire somebody who doesn't demonstrate that they're hungry and that they're humble and they're smart. And trust me, I've 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. And you know what's interesting about culture is once you get a solid culture that's based off of your values and you hire correctly, no longer as a CEO are you responsible to be the keeper of culture. The business itself keeps culture. I always say it's like angular momentum, which is once the culture is set, if somebody sneaks into the filters and gets in that this and the cultural fit, the teams eject them. You just can't survive at Procore if you are not hungry, humble, and smart. And if you don't live our values, it just that simple.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  47. “Actually, I know a few CEOs who really think people are a commodity. I wouldn't say most at all do, but I do think it's important. And so what we have done is very intentionally we hire to our values. So if you go through the interview process of ProCore, you may think you're being interviewed for your skill set, but to get into the interview process, you've already had to demonstrate that you have the skill set to do the job. The real hurdle to get over is do you live our values and do you value our values?”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  48. “Trust me, having security and stability is priceless. All I'm saying is the baseline level of stress involved has not diminished at all. As a matter of fact, you know, we have 4,000 employees globally and we have 16,000 plus customers. The blast radius of screw-ups is so big that you can't take that lightly.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  49. “You know, this is one of the areas, Harry, where I'm absolutely most fascinated. I always find it's interesting that the way people approach me seems to be they're curious about like kind of like what my day-to-day job is like so that the Instagram side of things like you must have it so easy like you're a $9 million billion dollar company and things seem to be going up into the right they don't really understand the complexity of the job and they actually think it's they think it's easier than it is in reality the job it's a 24 hour day job I've been doing it like an eight thousand nine hundred days of Procore, right? Never having a day.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  50. “So I'm in the camp of you really cannot overcome your weaknesses to a level that is going to be satisfactory for the business. At the scale that Procor is at today, I can't be a mediocre finance guy and I can't be a mediocre HR guy and I can't be a mediocre salesperson because that's not going to help the business, right? So I know where my strengths are and I know my strengths are. I set the vision for the company. We help build the annual plan. I provide resources to our teams. I spend all this time with our customers knowing what their needs are. And that's the stuff that gives me energy and fuels me. But when it comes to like the low level operations of the business, I'm just not great at it. So I surround myself with great finance people and great HR people, great legal people doing all the work that I just am not great at and I don't intend to be great at.”

    2023-12-04 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source