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

23:19Well it's any to the person that said that to me had flown down here on a private jet so I was kind of not concerned that their deal was going to make it so their kids didn't eat. Absolutely amazing. I love that. Can I ask what did it really ramp then? So then you raised money from Basma and you know your then what future CFO. Yeah. And you were at 9 .6 million, I think he said. Yes. What was it like? You know, I really started within about a year where we would double and then double again and double again and double again. I mean, around 2017, we were rolling. What's really interesting to me, Harry, is in hindsight, we never stopped to kind of think about what the heck was happening.

23:57You know, I used to, when I was a kid, as a skateboarder, right? And so, if you're, when I was skateboarding down the hill and you get too fast and you get speed wobbles, You have to leap off your skateboard. You're hoping that your feet can run as fast as the speed of the skateboard So you don't fall on your face Those years were us running as fast as we possibly could try not to crash So we had no time to kind of think about like what the heck's going on here I'll never forget when we got a billion dollar evaluation on ProCore. We were raising some private capital We were all standing in a hotel room somewhere where we're at a conference the leadership team and I was talking to our investors about the pricing around and it came up to be a billion dollars and I'll never forget that was a moment where I'm like I had missed like a hundred million evaluation to a billion and that we were all like wow we've significantly grown this business and it kind of happened without us thinking about it.

24:47Do you think naivety is a good thing? You mentioned that about kind of fooling on your face. People say it only sometimes they say it's not. How do you think about that one? I actually do believe it ignorance sometimes is bliss, but all the time. I also think that you can be too smart for your own good. So us having this singular focus on what we were doing, and really not trying to just build a business, but actually solve a real problem and satisfy the needs of the customers, just kept us really, really focused. And so you can call it naivety or whatever, but like, that's all we were really thinking about, you know.

25:17So it's really interesting. You said that about focus. I had chatted and sorry, this wasn't in the schedule because I just had it from well and brine, so recent additions, but I had about kind of the dozen products that we now have a pro core, and I wanted to ask, and they asked, actually, to be fair, I'm such a VC, take credit for others' work, you can tell it's the natural proclivity of mine. What were your biggest lessons in terms of scaling product line without losing focus? There's a lot of lessons in there, right? So up until 2017, we only had one product. It was our project management tool, it's still our flagship product.

25:52But what we had heard was our customers were, they were sick of having point solutions. And so they really wanted to have our platform be the platform of choice for all of their kind of core business needs. And so we very deliberately forced rank those. We prioritized which of the biggest needs and kind of worked our way down from there. So one big lesson we learned was, you know, in the early days you're kind of faking it to you, make it and you don't really realize that scale might happen. And so some of of our financial product line was a great example was, we had built that very quickly, got it to market.

26:25Our yearly wasn't 100 % enterprise grade. 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 get this thing to the point where it was enterprise grade, we weren't going to be able to scale it. What year was that realization? 2019? 19 wow yeah, we had to tell our customers like look though all we've been we've been talking to about a lot of features That we're gonna be building we're gonna actually pause on this for now and you know you're trust us You're gonna you're gonna love it.

26:58You know what's so cool is that till this day customers still come up to me And they're like though that was really hard for us to hear it was the smartest thing you guys ever did on that product line Because now it is completely changed the way we do business and it's completely scalable and it's enterprise grade So yeah, but that was that was a hard decision to make the use scale to what were your revenues in 2019? They must have been 50 to 100 yeah Probably without having an enterprise -grade product Well, so our project management tool which is our flagship was definitely enterprise grade This was a newer product we had just brought into market and it was kind of becoming wildly successful And to the point where we've really had to go back and shore it up to make sure that that we could actually deliver on our promises Any other big lessons in terms of product expansion when to do it mistakes that were made?

27:47Yeah, one thing that we did learn was so when we were selling into the Australian 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 the construction company would go to prison for manslaughter. All of a sudden when we were talking to our customers in Australia and New Zealand, they're like, look, love your project management tool. We need quality and safety because I don't want to go to prison, right? So we're like, okay, so we started building this product for them, and we got really good product market fit.

28:21And then what we realized is that we took it, you know, globally to our global customers, everybody valued that new product. And so we were able to kind of hyperscale that product because one market demanded it, but the rest of the market needed it. So we learn that we had the opportunity to kind of capitalize on those finite needs and then take them globally and it worked And so please you said about taking them globally because Will said you know obviously about the recent and the very successful kind of global expansion He said I'd love to hear to his take on what's been the biggest lessons from international expansion?

28:53What what what didn't what you wish you'd known? Yeah, yeah his thoughts there I like to tell people this which is it's just a reminder at every day in ProCourse history I had never been the CEO of a company of that scale before, right? So like because it was growing, right? And so everything was I had to learn a lot as we went So there were a lot of lessons learned you know going internationally It's really tempting to say what worked in the US market is gonna work in another market I would say some of the biggest lessons learned was you have to build a brand and you have to build loyal customers and in referenceable customers in those markets before you really can expect any sort of scale and growth in those markets.

29:33Does that mean you should then limit budgets, do it from where you are, build that base, and then move people there? Is that how you'd recommend? 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 brand, get the ground swell going with the referenceable customers, then put your go -to -market team in afterwards to capitalize on that. And all kind of candor, we went all in into our early markets thinking like they're gonna love us, it's all gonna go well. We have learned that there is a playbook here and that you have to really build that brand first.

30:11But what we find is the longer that we've been into any particular market, the more success we have. So the way you enter markets matter and you have to be patient, nothing's gonna happen overnight. It took us years to build the brand in the US and so we have to be patient building brands and numerous. One thing that you did quite differently compared to SAS is most of SAS is predicates on a per -seat model. When I was a little bit of a whirler and Brian they told me about the decision to be volume based. I'd love to hear your lessons on pricing from maybe contrarian decision to be volume based.

30:42And that question of could you have been as successful if you were seat based? No, so our mission is to connect everyone in construction on a global platform. I knew from day one that if we went with a seat based licensing model, which by the I remember I'd run a technology company before this. So like, that was the only really prevalent model at the time was C -Base. I knew that what would happen was our customers were gonna make value decisions based on who was gonna get a seat. But the way that construction done is as a team sport. And so you need everyone to have access to the system because everyone needs to contribute.

31:11So I realized that I couldn't go with a per -seat model because that was gonna make it so we were never gonna be successful. And so I had to come up with another yardstick. And honestly, the only thing I could come up with was construction volume. One of our customers one day said to me, Harry, I said, how do you buy other things? And he said, well, I buy our insurance based off of our construction volume. So if I'm going to do $10 million with the construction volume next year, I will buy $10 million worth of insurance. And so I thought to myself, well, here's a way that they're used to buying.

31:39And it's actually a yardstick that actually scales nicely with customer size. So let's adopt this. It was so wildly unpopular with our customers. Even till this day, some of our customers don't love it. but it is the ultimate yardstick and we really believe in it. Why did you keep it when it was so unpopular? Like how did you get over that? Like do you just educate them on why you chose it? Yeah, so we did and you know as one customer would adopt it, they would actually realize that it gives them the flexibility to buy more or less a pro -court in any given time, yet they're able to get all of their team members and their collaborators.

32:14You know a construction if we sell the you know hairy construction right? You're gonna invite all your subcontractors onto the platform. Those folks are working on the platform for free. They get all the benefits of ProCore, but you're paying the bill, unless they want to become their own customer. So these folks would go and tell other general contractors, hey, I'm using this amazing product. So ultimately, our success kind of was the driver of adoption of this new pricing model. But like I said, even so this day, I was on a call last week with a customer who's still wishes that we had a different pricing model.

32:43Do you think that CEOs will always need to get on calls? ProCore's day is a close to $9 billion public company. Do you think CEOs will always need to close the biggest customers? So I actually have a very strict line at ProCore. I do not do deal negotiations anymore. I haven't for the last five or six years. I build relationships with the customers that I do not want to be transactional. I make it very clear with all of our prospects and all the people that I'm talking to or customers at Renewal. That I'm not going to be doing the commercial terms. But what I am going to do is I'm going to be a long -term partner of theirs to put together a joint strategy of success.

33:20And so I create a very big delineation. I talk to a customer, I think every single day, I think there's nothing more important that a CEO can do than to talk to a customer. And I actually get kind of blamed for it sometimes. Like people who are like, are you spending too much time? And I just don't believe you can spend too much time with the people that you're serving. Are there any other hard lessons that you think are really important to discuss? As I said, it's such a journey. I don't wanna leave out an epic. So I had the privilege of mentoring some CEOs of tech companies that are growing their businesses and one of the things that I In part on them which I wish somebody had imparted on me was in the early days of a tech company You do everything your job is to do like literally yeah, I was writing code I was taking out the trash.

34:01I was I was doing everything it a certain point in your leadership scale You have to learn how to stop doing and start leading and it's a really unnatural emotional motion for people that are just used to getting the job done themselves. And I see it till this day here with leaders of ProCore, not senior leaders, but people that are moved into manager roles, and the difficulty that people have of letting go of doing the actual work and empowering their people. And I think that that's probably one of the biggest challenges with anybody. I have this problem and then you actually finally delegate it to someone and then they don't do it as well as you.

34:36And you go see the A -need -me. And so you go back in and do it and then they never learn and they never do it So help me literally how does one do this efficiently? You have to let them fail now you want to you want to minimize the blast radius, right? You can't let them fail with an existential threat But you you have to let the fail I look at this very much like I look at parenting right a lot of parents big mistakes are They watch their kid start to stumble and fall and they try to catch them and save them from it, right? My parenting style was always like, if Henry was gonna stumble and fall, look, I didn't want him to hurt himself, but if he's skinned as knee, for instance, and kids get like freaked out, and he would look up at me, I would be like, you know, hey, that was a quite a tumble you just did, as opposed to being like most parents, which are like, oh my goodness, like that is the scariest thing I've ever seen.

35:23Let me help fix you, because you want people to learn from their mistakes, and you want to teach them without doing their job for them, how to overcome those obstacles. So it's, it takes a lot of like trust in order to do that, but you have to do that. Do you still struggle to navigate today? No. It's actually, I did for a long time. I realized that my kind of superpowers are not in the operational activities of the low level detail. One of my motto's has always been, know your strengths and know your weaknesses and hire to your weaknesses. So I know what I'm not good at. So I hire these amazing people to supplement my challenging areas and where I'm just not empowered and I'm not passionate.

36:05I'm gladly giving it away. I'm so pleased you said that because you said to me before knowing my weaknesses has been the key to my success. What are your weaknesses and do you always agree with hiring them away or should we actually get good at all weaknesses? Some people say so some others not. 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 ProQ was 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?

36:41So 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 So I surround myself with great finance people and great HR people, great legal people to do in all the work that I just am not great at and I don't intend to be great at. You said there about kind of doing the work that you're not great at and you'll never actually become better than satisfactory at it unless you really, really try.

37:17Totally agree. I think there's a lot of perception and reality or kind of Instagram and reality. How do you think about the Instagram versus reality of being CEO? 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 is seems to be they're curious about like kind of like what my day -to -day job is like so that at the Instagram side of things like you must have it so easy like you're a $9 billion dollar company and things are 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.

37:54I've been doing it. I'm like at 8 ,900 days of ProCore, right? Never having a day or a moment off and it's a hard job. I think you had easier over time. No, I disagree. Okay. This is a different. It gets different, right? I agree, but like two e -like that's just I your success is phenomenally unparalleled different to mine But like I now I'm in a beautiful house and I have Fiji water. Yeah, it's really high pressure It's quite nice having like not shit I'm gonna be on the street. Trust me, having security and stability is priceless. All I'm saying is the baseline level of stress involved has not diminished at all.

38:36As a matter of fact, we have 4 ,000 employees globally and we have 16 ,000 plus customers. Like the blast radius of screw ups is so big that you can't take that lightly. And you said 4 ,000 there. Brian said about the amazing culture you have. He said ask him what if you specifically done to have such a good culture across now 4 ,000? You have to be intentional about culture. Were you always intentional about culture? Actually, I know a few CEOs who really think people are a commodity. I wouldn't say most of them all do, but I do think it's important. And so what we have done is very intentionally we hire to our values.

39:15So if you go through the interview process approach, 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 they get over is, do you live our values and do you value our values? I love a good discussion. Whenever people like me hire to our values, I'm always like, who's values are really contrarian, respectfully too. So everyone wants someone who's like hard working and ambitious and kind. I'm not a team player. I'm largely in it for the money and I am egotistical.

39:49I'm not saying I'm any of that. But like, I could be really fucking great for business. 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 or you responsible to be the keeper of culture.

40:24The business itself keeps culture. I always say it's like angular momentum, which is once the culture is set, if somebody sneaks into it through the filters and gets into the cultural fit, the teams eject them. You just can't survive a pro -core if you are not hungry, humble, and smart. And if you don't of our value. It's just that simple. Was there ever a time where it slightly got away from me? Where I was like, this isn't how I wanted it to be. And do you take me to that time? 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.

40:59I'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 some point, you know, you really have to get real and say know to people that might have a big impact on the business, but you just know we're not going to be a cultural fit. And in our scale, Harry, there's no longer a superhero approach, 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.

41:33And you can't do that if you are kind of selfish in your individual contributor who all you you want to do is roof your own success. It just doesn't work. The thing that I've done many times, and I see a lot of founders do, is they hide the brand. They must be great. And then you get them there and it's just terrible. We have definitely learned which large tech companies to not hire from. Because honestly, you can just go right back to the culture that is existing in those tech companies. And you're like, you're basically hiring in that culture. And if it's toxic, do you think there are towels beforehand?

42:03I know that sounds weird, but so I have some towels. Like if you're a bouncer, you're one year here, one year here, two years here, one year there. Negotiation on title. I need to be chief of staff, not just chief of staff. You know the inverse, which is really interesting, is that ProQ war, 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 like granted to you.

42:36You don't get this because you ask for it You get it because you actually do the work and earn it. Will you not then ignore the response But as he's a being a director do you see what I mean? You don't want to encourage people to do your boss's job 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 I'm always like, are you a plate adder or a plate remover? Just be a fucking plate remover. Find your boss and say, what can I do to remove place?

43:09Yeah. By the way, we have a saying to Procours, 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. So what are you doing in the difficult situation when someone internally wants the promotion, but actually you feel it's an external hire that should get it instead. How do you manage that difficult process? It's such a broad subject because, you know, for 21 years, I've had to make very difficult personnel decisions.

43:39One of my very old mentor mine, Toby Lutke, as you know from shop. Yeah, I had him on the shows. He's awesome. He's awesome. Someone wants to describe him. If humans could be IP addresses, Toby would go away. 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, 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 a 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.

44:21So 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. My question to you is like, when people are loyal and they put in the hard work, all the inputs are there, but the output isn't there. What do you do then? 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 is not scaling, right? You get all of the tails going up to it.

44:54You 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 it can go. It's so funny, you said there about Toby's advice to you on kind of scaling and a faster rate in the company. That's really hard to do.

45:21Do you ever feel that imposter syndrome itself doubt of, oh shit, I don't know if I can do that or keep doing that? 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 pro -core we started hitting scale like around 2017 and 18 and things started really flying along I started being asked to go to these investor conferences in the Bay Area And you know, and it was like the time like Jeff Lawson was there 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 best and they'd all gone to Stanford and they all were out of central casting and here Here I am, like a college dropout carpenter sitting on this panel and going like, what the hell do I know?

46:13That was kind of an existential crisis personally for me. I wasn't Frank Sluven and I wasn't these other leaders that I looked up to just in terms of pedigree. Well, did you tell yourself then? Because that's... Well, 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 to 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.

46:44And 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, I, you know, whatever, right? 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, right?

47:17But I was willing to kind of throw my badge down 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, it wasn't as scary as I thought it was going to be. I think the biggest challenge is kind of knowing who you are. And I think that's a lot of people don't know who they are. Do you think you're always new who you are? No. I'm kind of going through a phase in my life right now where I'm really doing a lot of introspection on what's it all mean and who am I and all of that.

47:51So I don't think you ever truly know. But I think what you do know, again, is you know your strength, synah weaknesses, and you know kind of at the core who you are as a person. And if you just stay true to those things, I think you can deliver your authentic self every day and it's fine. I, again, rate different scales, but I had a terrible look for me was humongous and I was very upset. And my dear friend who's about 70, one of the best in the world said, what makes you happiest in the world? And I said, walking around the part with my mum and getting an espresso. And he's like, that's who you are.

48:23Just remember that. And I now just think of like, when one wonders who they are, what single case makes you happiest, too? Well, it's funny. I do this all the time here, which is on my most challenging days when things are kind of stacking up and No good news is landing on my desk Happens like I'm just more shit Here comes more stuff I call a customer. I honestly do I and there's nothing that gets me more excited and grounded and the level what I do than when I talk to a customer so I literally do I'll be like I'm gonna stop everything today I'm going to call a customer and it absolutely changes my attitude.

49:03Tooie, I teed you up. Okay, I teed you up. I gave you the example of my mother. I gave you the chance to say I cool Hillary. None. You cool of customer, brilliant. I didn't trouble with my wife, Harry. Thank you very much. No, listen, you got the first, like, credit in at the beginning. So we're kind of working our way back to neutral now. I do want to just find a one on like CEO ship. The common statement is that the best CEO is the best capital allocators. Is that true, do you think? Yes, I'm 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.

49:44One 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 on the responsible party here, so I have to get it right. Was it been the biggest capital and misallocation decision you've made? It's a great question. It is, you're right. I haven't asked it before, but I like that one. Which, it kind of gets to the regret thing, and I tend not to spend a lot of time thinking about regrets, but I would say, do you know what the you learn from the things that didn't go well? Yeah, but that's why I don't really consider them regrets, right?

50:18Like 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 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 And 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, you know, can take the business.

50:51The end decision is the decision. I think we should have had your wife on the show. I'm not with that option. I'm sure she's available. I think she's around. I don't know. I think she's just like, before we move into marriage, which I do want to discuss, we touched on kind of who we are. I think people lose themselves often, blinding when they make a little bit of money. And there's something that I think more people should think about is their relationship to money. How do you reflect on your own relationship to money and wealth today? 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.

51:27And I'm like, that's not a thing. You don't become an entrepreneur. Like, you follow a passion and you deliver, 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. Do you find it seeps into other relationships?

51:59And I, I don't mean those two personally, but I find now that like people are quiet when you talk and people won't argue back as much with you. And that's actually quite sad. I had a very recent experience with a group of leaders at ProKor 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 walked 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 -floot 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.

52:54There's three people that I call my cabinet, right? What is my wife Hilary? What is Suzanne who I think you buy to talk to? And the other one is Paul, my XCFO. And those three people will call me an idiot all the time and they'll remind me that by you know, crazy ideas or crazy ideas and they basically keep me completely grounded because otherwise if you live in a world where everyone tells you that every idea that you have is genius right eventually your 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 people who remind me how human I am and that really helps me a lot I love the way you said the governor that I love David Goggins I don't know if you He says, everyone is mediocre, and everyone has a governor on their minds, and they stop at 40%.

53:47And so I just immediately thought of that when I heard governor, so you can tell clearly I listened to him far too much. Can I ask, that's one thing, but that's new. When you have kids, you then have to imbue those values on them, and it's very difficult when, subliminally, they're brought up in a nice house and a nice car, imbue. And I've spoken to $50 billion founders, And 48 said this was the hardest thing. But how do you impede values, hunger, ambition in children, when money's not a problem, don't they? 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.

54:25So we have friends that though they will fly around on a private jet, they wanna drive a minivan because they wanna show their kids that they're not that or something. We never played those games. We always believe 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 gonna 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 any responsible person, right?

55:05And 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 you know runs a very successful business at age 25 and I couldn't be more proud of him. 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 Hilary said to him like look either you stop acting like your friend and you become Henry or you can leave my house. So he's like, no, I'm not going to do it. So she got him all dressed up.

55:39She packed a suit case. She put the push of outside the front gate of the house and shut the door behind it. And he learned his lesson very, very quickly. And then, you know, obviously let him back into a certain point. But just being categorical and how you instill doing right and wrong and not having any and be way and how you apply it, just it worked. Henry is 25, Pro Core is 21. I'm always very nervous on this D2 about having children, because I'm worried that I will be less performant, mediocre at what I do, because if you wanna do parenting well, you gotta be committed. Yep. How do you do see your Pro Core well and be there for Henry for soccer games, for pickup, for whatever that is?

56:23I 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 pro core fortunately for me We have an amazing relationship and he's yet I are like best friends and do you think that's just what you have to do though If you want to be CEO of a public company I'm not saying you can do while but if you want to be the fucking best you go to give it everything. 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, going up north in L .A.

56:55And he goes, hey, dad, 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 gotten 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 I are 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. I don't, there's not enough time in the day to be able to do both amazingly well. Did you have to do it? Could you see F .O. and not have done stuff like that?

57:25I'm just like, there's, you have many earnings cool site, what, four -year? Things like that charges game in the Henry. Probably something you might remember. Whatever might happen. Yeah, I never can remember this earnings cool. 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, what do you do when you feel super overwhelmed?

58:01If 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 and people ask me like, 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.

58:37And I always think of it as like business, which is like every step matters. And so you have to be very intentionally, 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 and like 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 to answer the next problem question, but that's not like me. Is the only thing public market analyst should be asking?

59:08How's the LEGO? If it's like, you're very busy. It's like, oh, short. I haven't seen it in years, it's like a strong buy. Related to Henry obviously, marriage, I'm not married. How do you make marriage work and be a public market CEO? Are there any tips that you have for me, genuinely, for people who listen, that help make it work? You know, Hillary and I've 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 compliment each other really well.

59:41She's a yoga instructor, right? And I'm a CEO of a public -stated company. And we have very vastly different worlds outside of each other. And so we basically allow each other to have that space. You'd lighten if she's known in your world. I love it. 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 about Proquor. We talk about the family, we talk about our relationship, we talk about our mutual interest.

1:00:16It's not not a hard, I have this, but Proquor is you. 20 years in the Inventionism, I can't separate it. She forces me to. I've got a very, very strong willed wife. I don't have a lot of choice. But it works, you know? I would not be able to survive if I didn't have her. I wouldn't be a good CEO Proquor if I wasn't able to have, you know, her supporting me through this process, which essentially means giving me time and giving me my space that I need to regroup and get kind of Performance 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 gonna be done and everything's gonna be a state of neurotic, right?

1:00:58Founders 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 gonna 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 I had a guest on the show the other day and they said, how are you doing understand the thing that people get wrong about marriage is they can Flate marriage and happiness. Yes, don't about happiness.

1:01:30It's about persistence boy Yeah, and you know you asked me before does it get any easier with ProCore? It's the same thing as with marriage, right? It doesn't get any easier. Things become different, but you know, you still deal with challenges. Everybody does and that's life. You know, 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 dealing with adversity, Ultimately, the happier you are.

1:02:07So I think we have to dispel with the myth that we are all deserving of stability and safety and happiness in our lives because that's just not a natural state. Listen, I want to move into a quick far -owns. I say a short statement, you give me your immediate thoughts. Does that sound okay? Sure, go for it. So what do others not know that you know to be true? 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 if you would allocate percent versus skill to the success of Pro Cool What would you say it is out of a hundred?

1:02:55Well, I would give skill probably the lowest ranking I would give persistence the highest percentage score I would say that's the skill list Okay, well, if you can, you keep calling out the skill then yes, I would say the skills, yes. I guess you did the luck 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 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.

1:03:26What's the most memorable starting broke or was one? When I had decided was I was going to wind down my other business and I was going to wind up pro -core 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 We're literally a family friend knocked on my front door. I 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.

1:04:02If I had not said yes that day standing in my front door in my house in Sosolito, California, I wouldn't be here today. Well, it's the biggest thing you and Steve have disagreed on. 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 -spin -spin -spin. 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 on the floor.

1:04:33And 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 Pro Quarhats and I bought them back to the booth and it cost $100. Steve lit me up like I had just like taint the business. He's like, we don't have $100. Like what are you spending a hundred dollars on ProCore bread and hats to give away at our booth for and we literally have like this like a huge kind of Knockdown dragout over the hundred dollars. So yeah, that was that was a tough conversation and by the way I still have one of those hats. Well someone's the grandpa on the lawn on the Steve We wouldn't be here without the grandpa on the lawn.

1:05:11He kicked us a float So you need a grandpa on the lawn You can be CEO of any other company for a day. What company would you be CEO? I would think it would be Microsoft because I have the fortunate privilege of having Sock to 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 11 products and 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.

1:05:46What's the right way to view competition? 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 in ProCorp, which was a racecar 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 up the heart, which is like, listen to your customers, do what's right, and you'll win.

1:06:18And 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. You can have dinner with anyone that are alive and often anything. Who do you have in a way, them? What do you ask them? 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 a funny, I'm a good little choked up. And 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 employees, 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 for me?

1:07:08It would be the biggest privilege in the world did he see you success? No, I'm sorry. I think boys always want to impress fathers and groundfathers. That's something good news is my father is still around doing very very well and he is surprised Like literally I was the kid in the family they'd written off like I you know 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 got you got all these privileges. Well, I didn't do that. So like later literally had written me off I was working as a construction worker making $15 an hour living in a tiny little apartment.

1:07:44I 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. I mean, that is just amazing. I'm a uni -drop out to, so sadly, never quite go. That's difficult. What's the best piece of advice you've been given? This is 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 out of his 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.

1:08:20And I swear Prokhor 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 the 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 to me. Did you always know you'd be successful? 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.

1:08:52As 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 an honest day's wages and I would be fine. What's the most lavish spend that you've had? 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. Come on! I had Cuban on and he's like the Gulf Stream is pretty nice. I don't know the plane. Well, wait, I drive a five -year -old Toyota Tundra pickup truck that's all beat up and has a bit frame like and by the way I don't do that because I'm trying to prove anything to anybody.

1:09:29I just do it because it kind of falls back into that authentic self like I'm a construction worker like I There's just I don't need all of that good for the brand totally with each No, I honestly I think that's great and I'm so with you. I never get watches never bought watches I may have just bought myself a decent watch for the very first time in my life actually my son Henry who's 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 so they normally had worn we won't tell Hillary it will be our secret Her way, her motto is, you buy yourself something, I'm gonna buy myself something.

1:10:04So that's the way it works. So we're very open and transparent. Final one for you. Why do you want to be in 10 years? You said about kind of this interesting intersection of your life. Why do you think two years in 10 years time? So I'm still only 56 years old. This is assumed they haven't put me out to pasture yet here at Procorp, 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 a some out buildings. I'm building a western town up there with like a saloon and a jail and a Bakery and all this other stuff.

1:10:37So I'm gonna have my tool bags on. I'm gonna be at my ranch and I'm gonna be building something That my absolutely love it to you. I've so enjoyed this discussion. Thank you so much for putting up with my British humor My wayward question. Keep in fantastic. No, thank you very much. By the way, I feel like I've been having dinner with a great friend and you know, for half an hour and sharing a bottle of wine. So I appreciate it and thank you for putting up with me as well. I just love doing that. You can tell in my tone how much fun I had there. If you want to see the full video of that discussion, you can check it out on YouTube by searching for 2 .0 VC.

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