Tracy Young is a cofounder and the CEO of PlanGrid. PlanGrid makes mobile construction productivity software. They were acquired by Autodesk in 2018 and were part of YC’s Winter 2012 batch.

Kat Manalac is a Partner at YC.

You can find Tracy on Twitter @Tracy_Young and Kat is @KatManalac.


Topics

00:15 – How Tracy got into the construction industry

2:20 – What convinced Tracy and her cofounders to build PlanGrid?

3:00 – Finding a technical cofounder

5:55 – Tracy still sees herself as an engineer

6:45 – PlanGrid’s MVP and their first customers

11:25 – Their sales process

13:15 – Product breakthroughs

16:50 – Not firing fast enough

20:00 – What does she look for when hiring someone?

25:30 – Tim Cook’s closing statement at WWDC

28:15 – Fredi Fernández asks – Does Tracy track wellness levels of the team?

28:55 – At what point did Tracy hire an office manager?

29:50 – How does Tracy take care of herself?

31:15 – Founding a company with a partner

33:00 – Managing a company as a new parent

35:15 – Seyed Rasoul Jabari asks – What’s your big plan to go from 1.5 to 10 million projects?

36:15 – Holly asks – What has been your single largest influence in helping you scale?

37:35 – Why do some executives not work out?

38:25 – What skills did Tracy have to work on when scaling?

42:10 – What do a lot of startups get wrong?

45:50 – Tracy’s recommended books

47:30 – What Tracy wishes she knew when she started out



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Transcript

Craig Cannon [00:00] – Hey, how’s it going? This is Craig Cannon and you’re listening to Y Combinator’s podcast. Today’s episode is with Tracy Young and Kat Manalac. Tracy is a co-founder and the CEO of PlanGrid. PlanGrid makes mobile construction productivity software. They were acquired by AutoDesk in 2018 and were part of YC’s winter 2012 batch. Kat is a partner at YC. You can find Tracy on Twitter @Tracy_Young, and Kat is @KatManalac. All right, here we go. All right, Tracy Young, welcome to the podcast.

Tracy Young [00:33] – Thank you for having me.

Craig Cannon [00:34] – How you doing?

Tracy Young [00:34] – I’m doing good, thank you.

Craig Cannon [00:36] – Your company’s PlanGrid and you were in the winter 2012 batch. For those who don’t know, PlanGrid is in the construction industry. But how did you get into the construction industry?

Tracy Young [00:48] – I wanted to be an architect and I wasn’t accepted into any architectural programs, which ended up being a really good thing for me. I love buildings. Spaces have a way of just making us feel so much, the spaces that we love, and I wanted to be a part of that building process.

Craig Cannon [01:09] – So your first job out of school was a construction engineer–

Tracy Young [01:13] – Yeah, I was a construction engineer

Craig Cannon [01:14] – or how did you start before?

Tracy Young [01:14] – I had muddy boots, hard hats, safety vests and one of the first things you’re tasked with as a rookie construction engineer on a project is QA/QC of the job site, very much like…

Craig Cannon [01:26] – Quality control.

Tracy Young [01:26] – Quality control. You basically take the specifications and the blueprints and you go out on site and then you check it. That’s where PlanGrid’s idea came from. Two of us were construction engineers, the founders of PlanGrid, and three of us were incredibly talented software developers.

Craig Cannon [01:43] – How did you actually end up picking this idea? Because I’ve heard several interviews with you and you talked about batting around ideas with your co-founder for years before.

Tracy Young [01:51] – Yeah, so, my co-founder, Ryan Sutton-Gee, he just has so many ideas. He knows so much about the world, and he’s he’s just entrepreneur mindset.

Kat Mañalac [02:02] – Can you share any of the other ideas that had come up?

Tracy Young [02:04] – It’s so funny. We were trying to think of all the weird ideas he had come up with. Certainly he had pitched wanting to start a construction company for several years as we were going through construction engineering program. The one that comes to mind is cat roulette. We would adopt all these cats, put cameras on it, and then you would, if you wanted to just see a live webcam of cats, you would just tip them and you could feed them and you could play with them.

Kat Mañalac [02:31] – Sign me up.

Tracy Young [02:32] – Ee didn’t end up building that.

Craig Cannon [02:35] – You know tons of these people right? They’re always pitching start up ideas to their friends. Obviously, this one has more product-founder fit, but what was… I know the iPad was coming out right around the time you guys were starting. What convinced you, this is the thing I’m going to commit to building?

Tracy Young [02:55] – We just started off as a fun project. PlanGrid, at least for me, I had no idea that we could build a business out of it and certainly not one that would have a $900 million outcome. It was just a fun project when we started building it. When we realized it would become, it could be a business was when we sold our first million dollars. It was like, whoa, we did this without a sales team.

Kat Mañalac [03:22] – How long did it take to do that?

Tracy Young [03:23] – I would say two years.

Kat Mañalac [03:26] – Can you talk a little bit about how did you know that the co founding team was the right team that you wanted to build something with longterm?

Tracy Young [03:34] – We were all friends. We liked hanging out with each other. Some of us worked together. Two of us were dating, now married with a kid. Three of us had gone to college together. We had done projects together. We had just known each other for a while.

Craig Cannon [03:48] – But the story of adding your boyfriend at the time is kind of funny, right? Because my understanding is that you were kind of shopping around for a technical co-founder.

Tracy Young [03:57] – Oh, we went through, the idea of the digitizing workflows for the construction industry, it’s a super simple concept, right? Take the blueprints, take the specifications, throw them in the cloud and make them available on mobile devices, which was impossible in 2011. Ryan had pitched me this idea and we actually just opened up some blueprints on the first generation iPad, like whatever it was, Acrobat Air at the time. And this box comes up and it says, out of memory because blueprints are incredibly, they’re high resolutions. They’re 10,000 pixels by 10,000 pixels and the first generation iPad couldn’t handle it. There’s this moment where Ryan’s just like, gasping, he’s like, we should build this. It was like, this is actually a really good idea. It would be super helpful. And we would go through this period of what Ryan calls a saddest story in Silicon Valley which is we have an idea and we have no technical….

Craig Cannon [04:49] – Yup.

Tracy Young [04:52] – co-founders to build it and I was seeing this problem as well. The saddest story of Silicon Valley. And so we would, we would go to our friends who were computer scientists, programmers, and we would pitch this idea and they would all say, this is a good idea. Our cofounder Antoine who is a high frequency training engineer in Chicago at the time, he said this is a fantastic idea. You guys should learn how to program. And we didn’t. I ended up telling Ralph, one afternoon, actually we were having dinner and he, you know, it’s at this point of our relationship where it’s going steady and we’re sharing little calendars.

Craig Cannon [05:34] – Silicon Valley Going Stead.

Tracy Young [05:35] – He sees this event, this recurring event on Thursday night with Ryan that says peanuts. He’s like, “Why are you meeting with Ryan every Thursday night for a few hours, subject peanuts?” It’s like, it’s funny you should ask. There’s this idea that we have and he is so offended, “Do you even know what I do? I’m a full-stack engineer.” Ralph is very confident and he’s actually quite talented. He’s like, “I’m the best engineer I know, I write iOS and Android apps on the side. I’m a rendering engineer at Pixar Animation.” And he’s like, “Why have you not told me about this before?”

Craig Cannon [06:15] – It’s really funny.

Kat Mañalac [06:16] – So he sold himself to you.

Tracy Young [06:19] – He did.

Craig Cannon [06:20] – Was your mentality to just go around and make projects and see what happens or had you been set on being an entrepreneur or did you just fall into it? How did that happen?

Tracy Young [06:29] – No, I actually see whatever it is, seven eight years, at PlanGrid and as PlanGrid’s CEO, I still see myself as an engineer, as a builder. It’s just something I like doing.

Craig Cannon [06:39] – Yeah, because you mentioned it earlier, but the product started selling itself, right?

Tracy Young [06:44] – Yes, I mean, we worked at it, right? We actually had to tell the story, had to show it off. But yes, we had early organic adoption. We’re very thankful for that.

Craig Cannon [06:55] – Okay. Because there are a bunch of questions that we saw on Twitter about that exactly. How did you get into. In the construction industry, especially in 2010, not necessarily digitally native people. Probably don’t have iPad’s right? On a construction site? How did you make your first money?

Tracy Young [07:14] – Well our first 20 users were people we had worked on construction projects with and then people who had gone to university with. We would just ask them to try out our software and give us feedback. And then at some point they would start using the word, like love. We’d call them every week and say, “Hey it’s Tracy, just checking in. How’s the new update going? Did you load it?” Of course I could tell if they did or not. “Hey, go load, go download the new update, try out this new feature.” They would give us feedback over the months, and this was during YC. At some point people would start using the word, like no, “This is great, I love it.” And it’s like, okay, great. That’s like, note to solve, it’s like, all right, someone’s going to pay for this very soon. That beta tag is coming off.

Craig Cannon [08:00] – What did the product actually look like at that point? We have so many people that come on the podcast, and oftentimes they’re like you. They have maybe a successful outcome or at least a product that you know. What was it?

Tracy Young [08:11] – Gosh, it was so simple. For us, what worked out is, you have to understand people. We so fully understood our users. Superintendents, foremens, electricians, carpenters. They have real work to do. Every minute on the job site is money and every minute counts. Every minute they’re trying to find information means they’re not doing their real work which is building. On top of that, this is a class of users who have just never used software to do their jobs before. How do you design and build software for people who don’t even know how to use a computer? Simplicity was revolutionary for us. We kept it super simple. We made sure that if we could build this feature in two buttons, let’s make sure we don’t do it in five. If we see people are tapping into our app, and it’s confusing to them, that was a moment we would change things because it was all about how fast can they access their information. For an industry that doesn’t, historically use software, there is a certain amount of education we would have to do. It’s not like, the head of HR at some Fortune 500 company switching out their HR payroll system where they know what they want and it’s just take this thing and then replace it. For us we had to even convince them, “Hey, these are mobile devices. You should invest in this. Not just for our software, but for everything else to run your project and run your business.” So not only do we have to educate them on the devices, especially in 2012, 2013,

Tracy Young [09:51] – we had to educate them on everything else that goes with it. I think YC has this motto of, do unscalable things for your customers, and we certainly, probably still do that today.

Craig Cannon [10:03] – Let’s walk through it, actually step by step. Give me ane example of an early customer that you didn’t know that you basically had to cold call or maybe you got an intro, but you had to start from zero.

Tracy Young [10:17] – We would meet them. Anyone who saw PlanGrid and was building off of paper, understood the problem that we were trying to solve. And it was like, “Yeah, that’s nice but I don’t know have mobile devices.” Really trying to find the friction point of why are they not adopting the software. Especially when you’ve built something that they actually want. And so for us, we had to remove the friction and the barrier of them not having the hardware to support the software. We, in 2012, we were giving out iPad’s away for free. Well no, actually, that’s not true. We were loaning it out to them. And then eventually we would just basically charge them enough money to cover the hardware costs.

Kat Mañalac [11:01] – And then did you have to sort of sit down with each one of them and walk them through?

Tracy Young [11:05] – Yeah, go in the app store. You know. Typing in the passwords.

Craig Cannon [11:09] – Download it, set up their account. All that stuff.

Tracy Young [11:10] – Exactly. Because we knew it wasn’t going to happen. Because there’s so many non literal fires to put out on a job site every single day that we knew that we just had to sit there with them and do that work with them until they got their project into PlanGrid and start collaborating on it.

Craig Cannon [11:30] – It’s interesting because many of these other software products, like GitHub, go if this bottoms up method. Did you ever entertain that idea? Or was it always, “We need to get this foreman.” I don’t know the hierarchy, but a certain level of person and then go down from there.

Tracy Young [11:44] – If I understand your question correctly, I think we did go bottoms up. We went directly into the field, which is normally not where software is sold. Because construction software has existed for 30 some years.

Craig Cannon [11:55] – Okay, I thought you were going up to people who were managing.

Tracy Young [11:58] – Construction software has existed for decades but the hardware didn’t exist to bring it out into the field where 98% of construction happens. If you’re writing software for the construction industry in the 1980’s, you were writing it for people in the office, the enterprise buyers, CIO’s, VP of operations, et cetera. Then they would deploy it and maybe there’s low adoption in the field, especially if mobile devices didn’t exist. Because you’d have to go back to your office trailer and then log into the computer and use the software. We purposely, consciously designed PlanGrid in a way where it would be valuable to everyone in the construction industry. One, because we wanted to maximize the potential TAM. We wanted to make sure that it would be valuable for a project executive and a project engineer as well as an electrician, and a carpenter. But it wouldn’t be customized versions, for these different profiles. It would be one product that would satisfy all the profiles as well as one product that would be valuable for any type of construction projects whether it’s residential or commercial or a road or a bridge.

Craig Cannon [13:19] – Well what you’re describing is now a giant, enterprise product. How do you go about product development in the early days?

Tracy Young [13:25] – It was the simplicity. We asked ourselves, what is the one thing everyone needs to do? Which is access the construction information. The first thing we did, we just provide access on a mobile device. Put it in the cloud and make it available on an iPad. Then we would later release it on an Android, and Windows, and et cetera.

Craig Cannon [13:45] – In terms of product development, were there any, so that’s obviously a huge breakthrough. Like early days you load this file on the iPad, it crashes. So, that’s amazing. You get people with that. Were there any other product breakthroughs that led a lot of growth or a lot of sales for you guys later down the line?

Tracy Young [14:00] – I’ll talk about some of my favorite features inside PlanGrid. Sometimes you want to look at your equipment drawings, just different equipments in the room, and then you also want to look at the electrical drawings, just to make sure you have an outlet to plug the equipment into. Or maybe it’s medical equipment, at which point it needs med gases and plumbing, et cetera. What you’re trying to do, is look at the same room, but look at different slices of it, of information. And sometimes you just want to overlay it. And so we, ages ago, released a feature where you’re able to just overlay sheets on top of each other and then see the diffs. Or it could be an old version and a new version if you guys are following.

Craig Cannon [14:41] – Yup.

Tracy Young [14:42] – And you could see what change from this version to the next and then just highlight in red. That’s one of my favorite features. Another feature we released is a full sheet search. Believe it or not, we are the only system out there for construction that allows you to search for any word on the sheets.

Kat Mañalac [15:00] – Oh, wow.

Tracy Young [15:00] – And bring up.

Craig Cannon [15:01] – I wouldn’t think of that.

Tracy Young [15:02] – You can imagine it’s like, and there’s always a certain thing, magnetic door hold opener. Sometimes you open up a door and then it slowly, it like, closes, it’s holding. They only occur on maybe, five sheets out of 5,000. Either you have it memorized or you’re searching through sheets all the time. With PlanGrid you can search for the word magnetic and then it’ll pull the five sheets you’re looking for which was not possible before. Certainly not when I was in the construction industry.

Craig Cannon [15:32] – Right. So this would be useful for someone doing inventory and ordering?

Tracy Young [15:38] – Just looking up information.

Craig Cannon [15:38] – Finding stuff.

Tracy Young [15:40] – Yeah, figuring out how to build it. Planning, ordering, yeah, exactly. Doing estimates. It’s super useful. One of the early features we released was version control. That felt revolutionary.

Craig Cannon [15:52] – That’s like, my understanding, Ralph was working on that a little bit, is that right? As someone personally, who does…

Tracy Young [15:58] – I actually don’t remember which of my amazing founders built it, but yes, it’s our technical team that built it. For PlanGrid engineering, it wasn’t just about providing access. I think I sold it short. It wasn’t just about providing access of the information. It was, how do we take technology that exists in the world, and apply it to the construction industry, and specifically, on the construction records set. Machine learning is a thing. We were doing it before it was cool. We can search for unique words like the first floor floor plan. Which could change 50 times over the course of two years. And we could version control them because we could read them. It’s like, A101, first floor floor plan. The next time someone uploads A101, first floor floor plan, we know that and we would say, “Hey, this already exists. Are you uploading a new version? We’re going to version control it for you so you’re not searching through…” It was a sheet based system. It wasn’t a file based system.

Craig Cannon [16:54] – Right. Which becomes super important when you’re printing out these layouts for people and then they take them into a building and then they’re operating off of an old plan.

Tracy Young [17:02] – Exactly. Which is actually, probably the cause of a lot of, I mean, there’s been studies on this. It costs the US construction industry $20 billion in waste every year.

Craig Cannon [17:11] – Because they have to tear it down and rebuild? Wow.

Kat Mañalac [17:17] – That’s wild. Thinking back to your time at YC, is there any specific advice from any of the partners or anything you learned during that time that’s stuck with you today?

Tracy Young [17:29] – I feel like all of the speakers including that came through dinner, one of their advices or their lessons was not fire people fast enough. Not only did you have the wrong person in that role but it would completely, their blast radius is too big so it would, it’s always someone of leadership, it would affect everyone around them. Because when someone’s not working out, everyone else knows and then the CEO knows.

Kat Mañalac [17:59] – It’s tough advice to process at the time because you didn’t have any employees.

Tracy Young [18:03] – No.

Kat Mañalac [18:04] – But yet,

Tracy Young [18:04] – But it’s certainly, we heard that so many times. And I think like, almost every single speaker talked about this. I’m assuming today as well. And so it would take us years before we were able to give the right feedback because when someone isn’t working out as a leader, as a manager, you’re also responsible for this.

Craig Cannon [18:24] – Right.

Tracy Young [18:24] – You put the wrong person in the role. And I say you as in, like, me. Then they remain in the wrong role because you’re unable to help them grow or get better or give them feedback so that they even know they’re doing the job wrong or not performing well enough for the company and then they’re also there because you’re keeping them there. It’s just bad on all levels. My advice would be, right people on the bus, wrong people off the bus as soon possible. How do you do that? I think, one, it shouldn’t be a surprise. I’ve certainly made this mistake many times, and I still to this day feel this like, it still hurts me at a deep level that I fired someone and it was a complete surprise to them. It’s awful. I would say the moment that we figure out someone isn’t working out, time box it. It’s like, oh, but there’s always an excuse right? But I just don’t have time. They’re pretty good. They’re performing. It’s like, net is a positive or a negative. It’s negative, they need to be out of there. And time box it. We’re going to let them know this isn’t working out and say some words like, “This is the expectations for this role, you’re not meeting the expectations. I think this is what you need to do to fix it. If you don’t do this, I will have to ask you to leave in three months from now.” That is what you owe your team member.

Kat Mañalac [19:58] – Right.

Craig Cannon [19:59] – How many people is PlanGrid right now?

Tracy Young [20:02] – PlanGrid is 450 people. And growing. We are now a part of AutoDesk’s Construction Solutions Team.

Craig Cannon [20:10] – Congrats.

Tracy Young [20:11] – And we are 12 hundred people altogether so that includes PlanGrid.

Craig Cannon [20:13] – Oh, okay. And then the other products of AutoDesk within construction

Tracy Young [20:15] – And then, you know, 10,000 other people in

Craig Cannon [20:16] – Yeah, which is crazy.

Tracy Young [20:18] – deep design manufacturing side.

Craig Cannon [20:19] – Related to firing people is hiring people. Now that you’ve hired 400 plus, not personally, but PlanGrid in general. What are the most important things you look for so you don’t have to fire someone?

Tracy Young [20:33] – Early on, early on when, let’s say, we were sub 50 people. What we were looking for were people who had high pain tolerances and people who could be generalists. Because we had to, there’s just too much work to do. How do you do all the work as five people, well, those five people have to wear multiple hats. They had to not complain about it. There’s work like, taking out the garbage because you probably don’t have an office manager facilities team and then also code. And so those would be the two traits that I would look for.

Craig Cannon [21:07] – Sub 50 or at any size?

Tracy Young [21:11] – Just when you’re small like that and everyone has to wear multiple hats. At some point, let’s say, past 50 people and certainly past 100 people just have to start specializing. One person has to be in charge of that one thing or else it gets too chaotic and complicated and you don’t really know what people are working on. You want to just delineate work and segment it out that way. The other thing I look for as a later stage and later stage startup, I’m counting as, I’m drawing the line at 50 people. And especially looking for leaders, I would look for people who are just authentic. If there’s ever a moment where you’re in an interview and it feels like someone’s bullshitting you, they’re probably bullshitting you. And do you really want to work with someone who bullshits? Probably not.

Craig Cannon [22:03] – My impression is that executives get very good at interviewing, right?

Tracy Young [22:07] – They do but you can also just sense it. Why is this person trying to show off to me? What is the motivation here? And if you can understand that and it’s acceptable to you then, fine. Or are they making themselves sound better than they actually are? This is where reference checking helps. Doing lots of reference checks. Looking for someone who’s authentic and then the other good indicator for success for that role is have then done it before and have they done it successfully?

Craig Cannon [22:37] – That’s a clear metric. That’s a great one. Authentic pain tolerance, I mean.

Tracy Young [22:41] – Much harder to judge.

Craig Cannon [22:43] – Well it’s harder to judge and it’s more easy for bias to slip in right? Someone’s like, I interviewed with Kat and Kat’s like, “Eh, Craig seems authentic,” but then someone else is like, “Craig’s totally bullshitting me.” How do you make that concrete in an interview process?

Tracy Young [22:58] – I think it’s much easier later on because you just have more team members and more eyes and more bullshit meters going off and not going off. Early on, I mean early on, “Who wants to join our little shit start up?” What is PlanGrid? What do you mean you’re writing software for construction industry? It’s just basically the first 10 people were people we had worked with before who are our friends or fresh out of college and it was the only job they could get. I don’t think you have to, we certainly didn’t have that luxury early on to try to filter people that way. Ryan, my co founders test was, if we did have the luxury of having an option to grade candidates, I think his test was who would I rather be stuck on a cross country train with?

Kat Mañalac [23:51] – All right.

Craig Cannon [23:51] – Trains specifically.

Tracy Young [23:53] – I think it was a train or like, car. Like, a long car ride. Who would I rather be stuck with? And that’s how we made decisions.

Craig Cannon [24:01] – I think people have different ratios. How much you get along with versus how competent they are.

Tracy Young [24:07] – Everything given equal and you have to choose.

Craig Cannon [24:09] – Yeah, yeah, yeah. Pain tolerance, too. Because so many people listening are looking for concrete things…

Tracy Young [24:14] – We would put ourselves in their shoes. Two people come to mind. Taylor, who was canvasing. Going door to door canvassing and getting no’s and cursed at and door shuts. Probably high pain tolerance. And spoke of it passionately. Saman was a literally, a door-to-door pencil salesman.

Kat Mañalac [24:45] – Wow.

Craig Cannon [24:46] – What?

Tracy Young [24:47] – For like Staples or something.

Craig Cannon [24:49] – In America?

Tracy Young [24:50] – He now leads our BD team.

Craig Cannon [24:50] – In, like modern times. Okay.

Tracy Young [24:52] – Yeah, yeah. In modern times. I don’t know when we met him. 2014, 2015 maybe.

Craig Cannon [24:57] – Whoa.

Tracy Young [24:58] – He was selling pencils. I was like, you know what, I think you are going to do great making phone calls to the construction industry. High pain tolerance, that’s what I mean. You can tell by their background. Then someone who went through all of that that still speaks very positively. Looking for, we can teach a lot of things but teaching someone to have a positive

Kat Mañalac [25:17] – Attitude.

Tracy Young [25:17] – Attitude. You can’t teach that. You either have it or you don’t. When we spend so many hours in a day at work, and especially when there’s always problems and it doesn’t always feel good, having those positive people is really nice, actually. Especially when they’re doing just as much work as everyone. Who wants to be around negative people? Let’s face it. No one. But the negative people exist.

Craig Cannon [25:42] – Sure.

Tracy Young [25:46] – I don’t know. Make them drink some sugar. That’s not good advice. I guess I’m just saying if you have the option, weigh a positive person a bit higher.

Craig Cannon [25:56] – Especially in the early days when they’re foundational and can influence other people even higher. To side track a little bit and talk about current events which I almost never do. Did you see all the backlash Tim Cook got at the end of the WWDC?

Tracy Young [26:11] – No, I didn’t follow this.

Craig Cannon [26:12] – He was thanking everyone for working really hard and working nights and weekends to roll out everything before WWDC this week. People pushed back because they’re like, what, this is not fair. This massive company promoting a work-life balance that might not be actually stable or may be good for the world. I have my own opinions there. But how do you feel about creating work-life balance at a high paced start up rolling out important products?

Tracy Young [26:41] – I feel like it’s just what gets elevated. I’m sure people at Apple, his teammates, actually appreciated that he took the time out to thank them. Because they probably did work really hard. I don’t think we get to see that side of this conversation either. But I do understand your question here. How do I think about work-life balance. It’s all about the outcomes that we create. It’s all about the output in terms of what we are able to create together. It’s less about the hours although, I will say, as a startup it sure seems like it’s correlated. If everyone is heads down, working, and you look up and it’s like, “Wow, we made a lot of progress.” And sometimes, a lot of the problems is just brute force, manhandling, woman handling these problems and this work to get it done. And so, I guess that’s my thoughts there. Certainly, like, especially now, I mean we have so many. It’s funny because when we were, in our mid 20’s early PlanGrid that seemed like the only people who wanted to work for us were people around our age. As the years gone by, myself included, there’s just more gray hairs in the building. What that also means is there are people with children and grandchildren that work for our company now. They are probably way more important than me.

Craig Cannon [28:10] – Yeah, than your job, sure. Well, ’cause I’m on Tim Cook’s side. I’m like, listen, the reason why they’re so important and the reason why all this matters is people do put in that work and they care a lot about it and I think that’s great.

Tracy Young [28:23] – It’s important to acknowledge that.

Craig Cannon [28:24] – Yeah, absolutely.

Tracy Young [28:25] – I like being thanked for when I work hard, you know? Right.

Kat Mañalac [28:28] – Totally.

Tracy Young [28:30] – I want somebody to acknowledge that.

Craig Cannon [28:32] – What you’ve done now, is he’s never going to say it again but people are still going to work. It’s just not realistic. Someone did send a question unrelated to this. Freddy Fernandez asked, “How do you track the wellness levels of your team or do you?”

Tracy Young [28:47] – I don’t think we do. Our office managers, our facilities manager, they, and our HR team, they do a really good job of taking care of the team. I remember, I do remember a funny story. From early days. I’ve been vegan for a long time now. And I’m also a little bit hippy. Like I want to eat only all organic foods and low sugar diet. Coke’s would show up or donuts would show up. And early on, I’m like, “What is this? You guys can’t eat this shit it’s bad for you.” And now I’m less crazy about it. Just because there’s so many people, it’s like, I don’t even know who brought in the donuts this day but it came from a good place. I’m a mature, Tracy.

Kat Mañalac [29:27] – At one point did it become, you have a team now, whose job it is to take care of the team versus at one point did it transition away from your direct responsibility?

Tracy Young [29:38] – I don’t know. It’s such a blur and a daze. Seven, eight years at PlanGrid going from five co founders to 450 people. And now a lot of revenue. I want to say 150 was when everything broke. Something about Dunbar’s number and everything. That’s complete chaos. I’m going to say if I were to best guess, probably about 150 people was when we had an office manager taking care of all of this stuff. Maybe before that. I don’t remember.

Kat Mañalac [30:12] – I’ve had the pleasure of seeing you since, I think I met you initially in 2013. I’ve kind of gotten to see you as a person, as your companies been scaling. One question I have is, what of the things that you’ve done to take care of yourself and your own, your family as PlanGrid’s gotten bigger and bigger? Other than eating very healthily.

Tracy Young [30:39] – What were the things I started doing? I started doing yoga weekly. That was really helpful. As part of that I also meditate. That was really important. It was life changing for me, actually. Just being able to quiet my mind down. Then just have a reset. Be able to look at things in a different perspective. Of course I am still very terrible at meditation and it’s really hard to, just to quiet our very busy human minds. I’m vegetarian, vegan throughout PlanGrid. I was vegetarian when I was pregnant. I was also taking a lot of vitamins at that point and that seemed to help. I drink a ton of water. I drink a ton of teas. I think between yoga and meditation, eating well, and that’s a plant based diet for me, taking vitamins, and then probably not drinking so much. Are the things.

Craig Cannon [31:42] – What about in terms of, we can talk about this much or as little as you want, maintaining a relationship with a cofounder.

Kat Mañalac [31:51] – We get this question a lot, actually, surprisingly. Maybe not surprisingly.

Tracy Young [31:55] – I’m very, very lucky to have a partner like Ralph. This company would not be what it is today, and I certainly wouldn’t be the human I am today without Ralph in my life. I’m sure he would say the same, but it is complicated. I would say, if you have the choice, you just wouldn’t risk your relationship in that way. For us, it works, right? It’s been eight years. We are still married. We have a child together. We will likely have more children together. A clear delineation of responsibilities is important here. I’m CEO, he was CTO forever. He would take on various interim VP roles for our team, which I’m thankful for. When it came to technical decisions, it was like I trusted him completely. When it came to business decisions, and just leading the team he gave me, I was CEO of course. I’m sure at some point he didn’t want me to have the authority, but they wanted me to be CEO and I was going to lead the team. That’s helpful. When it’s like, a co-leading situation, I think that’s where it gets complicated.

Craig Cannon [33:04] – And then what about at home. Does it all flow into one thing?

Tracy Young [33:09] – We also have rules. After 8 o’clock let’s not talk about work but we broke that rule all that time. We still continue to break that rule.

Craig Cannon [33:16] – Okay. And so, you mentioned this but you’re also a mom now. What was that process like when you’re managing this giant company?

Tracy Young [33:24] – Giving birth? I can talk about that.

Craig Cannon [33:26] – That process is fascinating but we don’t have to talk about that. Will you talk about fundraising? All this stuff, taking time off.

Tracy Young [33:32] – Oh, gosh, last year so my baby is going to be a year old next week. Last year was nuts. It’s a blur, for sure. Mostly because I was sleep deprived like all new parents. God, what is your question? Just tell you about it? It’s a blur, I don’t remember.

Craig Cannon [33:49] – How did it work? You’re managing this big thing but you’re also going through this huge life experience. I don’t know.

Kat Mañalac [33:56] – There was a woman once who asked me. She was like, “Hey, can you,” she was pregnant and she was thinking about raising her Series A. She was like, “Do you know anyone, who’s ever been pregnant and raised a Series A?” I really struggled. I was like, “I don’t know.” I can introduce you to some… I can figure it out. Is there any advice to women who are founders of companies or thinking about starting a company and balancing that? Having a kid and also taking care of this other kid which is the company.

Tracy Young [34:26] – First off, it’s totally possible. I was leading our team. I don’t know, however much revenue we signed us up for that year, and hitting our targets. Leading a team of over 400 people. Parallel padding conversations with, are now employers audited us as well as a Series C. And also the getting pregnant, and growing a kid, and giving birth and then nursing.

Craig Cannon [34:58] – All of that stuff.

Tracy Young [34:59] – You can do all of that. I’m living proof that you can do all of it. And what do I want to share here? I’m just a little bit crazy so I don’t know if this is good advice. I do want people to know it’s possible, you just find a way to do it. I remember at some point last year, during all of this, Ralph, he’s like, “Hey, I found your theme song.” We’re driving home. Had a pretty hard day. Pregnant, of course with my hard day. He turn’s on Drake’s “Nonstop.” I don’t know if you know that song.

Craig Cannon [35:32] – I don’t know it.

Tracy Young [35:35] – That was my theme song. It’s a lot like that.

Craig Cannon [35:41] – Let’s check it out. Cool, all right. Let’s talk about some other stuff. In terms of scaling the company, someone asked a question about, Sayid Jabari asks, “What’s your big plan to scale from one and a half million to 10 million projects?” Is that an accurate metric? Is that a public metric? How many projects?

Tracy Young [35:58] – I think so. How do we get to every single job site in the world? International is going to be key here. We’re certainly putting a lot of our energy and efforts and resources on our international strategy and investing in our international team. And countrifying our product so it’s ready for those markets. That’s it. Got to figure out where the TAM is, and it’s the rest of the world.

Craig Cannon [36:24] – Okay, and is that going to mean. Well, is AutoDesk international? Are they

Tracy Young [36:28] – Yes, yes

Craig Cannon [36:29] – all over the place? Okay.

Tracy Young [36:30] – This is also one of the reasons why I made this decision is that they have an incredible user customer base in international markets. They’ve figured it out. Now we’re bringing PlanGrid to them.

Craig Cannon [36:41] – Okay, cool. Another scaling question. Holly asked, “What has been your single largest influence in helping you scale? How did you make it happen?”

Tracy Young [36:51] – I’m obviously a first time CEO, although now I have some experience, seven years of it. Figuring out where I’m weak on, which was all over the place. Finding leaders who had done it before and surrounding myself with experience and people who had scaled to where we wanted to be three years from now. Incredibly thankful to have the leadership team that we have in place. All of them are still here at AutoDesk for now.

Craig Cannon [37:16] – How’d you close them?

Tracy Young [37:18] – How did I close them? Selling my ass off. Selling the vision. Selling the idea that their stock would be worth so much. Selling myself as an amazing leader that they definitely wanted to work with.

Craig Cannon [37:35] – Sure.

Tracy Young [37:37] – Putting and shining on my selling shoes. I think also just being authentic. Helping them understand why I was doing what I was doing. Why I was passionate about it and why I would be a good human being for them to work with and call their colleague. I think that helps.

Craig Cannon [37:55] – How often did you meet an executive that, sorry, we just had a hiring conference last week, and I’m just thinking about it.

Tracy Young [38:01] – Yeah, yeah. No worries.

Craig Cannon [38:03] – How often do you meet an executive that on paper you thought would be really good and then didn’t end up being good?

Tracy Young [38:08] – Oh, it always looks good. Especially marketing executives. This is their job.

Craig Cannon [38:12] – Oh, polish.

Tracy Young [38:14] – It’s hard to know. We certainly had misses. These are people who had done it before. And I think where we got it wrong was when they did do it before was scale. Like, they were either at a company that was way bigger and they just had never seen a startup of this size. ‘Cause it’s painful at this size. You don’t have 50 recruiters helping you recruit. We have a much smaller recruiting team, et cetera et cetera. And that’s when we got it wrong was when we got the wrong match in terms of scale.

Craig Cannon [38:50] – Okay. And then personally, in terms of you when you’re scaling, what skills did you really have to work on the most to make it work?

Tracy Young [38:59] – This entire journey is hard. It’s hard in a way where it’s hard to explain. I think you guys work with enough founders and you guys are previous founders yourselves. It’s lonely, also. There’s this constant, you’re constantly operating in the unknown with not enough resources. There’s all this pressure and there’s more pressure to be of any success at all. Yhen on top of that, life goes on. Our co founder died during this journey. But that wasn’t unique to us. Our team members have seen deaths in their families as well over the years. It’s hard on so many levels and I think our ability to manage our own emotions is actually a big key to just surviving the next day. Can we just keep our shit together? However you make that happen.

Craig Cannon [39:56] – Did you have a different personality type before you started meditating? Because you’re a pretty chill person, it seems like.

Tracy Young [40:04] – Thanks for thinking I’m a pretty chill person.

Kat Mañalac [40:06] – I was like, “Wow, chill.”

Tracy Young [40:08] – Please spread that rumor

Craig Cannon [40:08] – Oh, really. What’s your reputation? High strung?

Kat Mañalac [40:12] – Like, no, like even intensity. Certainly. Intense. But yeah. It’s like, maybe it’s like a duck though. You’re doing this under the water but you do have an external calm.

Tracy Young [40:30] – An external calm. Thank you for that.

Craig Cannon [40:32] – How did you cultivate that? Because we’re all emotional maybe to different degrees, but what do you do?

Tracy Young [40:41] – I don’t know if that’s, I think it’s just my personality. But certainly, when I’m really stressful, and maybe this would be helpful. When I’m super stressful and things are going bad. How do I make it seem like I’m still confident about the direction of the company? It certainly doesn’t come naturally. I’m not saying that I’m faking it or by any means of that. I think being confident and knowing that PlanGrid was the right product for our customers. I believe that. I believed that in 2011. I believe in that today even more so. I think, and then also believing that our team was the team to bring this product to our customers. That we just love builders. We come from building backgrounds. A lot of our team members have family members in construction. We care so much about this industry and the people in it, that’s what helped us I guess, be calm in those instances when things are going really bad.

Craig Cannon [41:46] – Yeah, it’s challenging. When something’s all consuming but you have the larger mission. And you have to stay positive.

Tracy Young [41:53] – What does that boil down to? Maybe passion and love for what?

Craig Cannon [41:56] – Picking the right thing?

Tracy Young [41:58] – Because things are going to go bad all the time. And it’s going to feel bad all the time. And when it’s not feeling bad, it’s feeling pretty good, it’s probably because something really bad is happening right now and you’re about to feel like shit.

Kat Mañalac [42:13] – That makes sense to me. We see a lot of people start companies and then realize that the customer that they’re working with. They don’t really want to work with that customer or solve problems for that customer. But that seemed to be the north star for you. You really understood that your customer, you were passionate about helping them solve their problems. I think that has really helped.

Tracy Young [42:33] – Yes. I think it boils down to passion.

Craig Cannon [42:35] – Now that you’ve bene doing PlanGrid for quite awhile now, when you think back to the early days, and maybe your friends starting companies. Just general advice, do you think there’s a category of stuff that a lot of startups get wrong when you look around?

Tracy Young [42:52] – Oh, wow. That’s a really good question. We talked about firing. We talked about managing people so that when you do fire them, they know it. What are other things that startups get wrong? For founders, certainly for me, at some point I wanted to just, things aren’t going right. I so desperately wanted them to fix itself. But I was working on the wrong things. Like, my life was filled with all these meetings and all these conversations and all this work that wasn’t actually moving the startup in a better direction. I was just doing this work. I think prioritization is what all people get wrong. But that can be corrected, right? By really taking an honest look at what we are working on

Tracy Young [43:49] – and is this the right thing or are we thinking bigger for the company and the people who work in it? Are we thinking bigger for our customers? And also to not lie to ourselves. I think that’s something we got wrong as well. When things weren’t going right, or when things were going right. And can we push ourselves harder? No. Whatever the reasons is, I think this is true for just our own personal lives as well just to make sure we’re looking at things honestly and you’re nodding. Like yes, yes, don’t lie to yourself.

Craig Cannon [44:19] – So many people have different methods of achieving that mirror. Did you have a coach, is it meditation, is it having a partner that you can also talk to about work?

Tracy Young [44:33] – We had a coach named Stratt. He was important in my growth as well. One of the most important things he taught me was to, it’s funny. He told me that I didn’t have, for someone who doesn’t have a lot of ego, you have a lot of negative ego. I said, “What the hell does that mean?” And I was constantly, I don’t know if it’s just my personality or if it’s just a thing that women do especially. Just put ourselves down. I felt so guilty about the mistakes that we were making instead of focusing on making it better. Acknowledging the mistake and then changing it. I would just beat myself down and it’s completely crazy. I remember I would, before every board meeting, I would just have this thought that goes through my mind. And I told you this, Kat. Where I thought I was going to get fired from my board. I remember accidentally letting that slip to my board member Carole before a board. I was like, “Yeah, are you guys going to fire me?” And she laughs. This loud cackle almost, like, “Are you fucking out of your mind?”

Craig Cannon [45:41] – Yeah. Wow. Okay.

Tracy Young [45:45] – The business was doing well. We’re growing.

Craig Cannon [45:47] – I understand. It seems like it’s going pretty well.

Tracy Young [45:49] – The team, I think loved me almost the entire time and we weren’t making that many mistakes. But that was a thought that went through, I think, right before every board meeting and leading up to it, that thought would cross my head.

Craig Cannon [46:03] – But it’s so hard, because you just get trapped in this stuff in your mind and you don’t even realize. You think everyone thinks the same way as you but it’s not true.

Tracy Young [46:08] – And that’s meditation helps is to just clean out a little bit of that clutter and burn it.

Craig Cannon [46:14] – That’s a good one. I know Kat, you had a bunch of other questions you wanted to ask.

Kat Mañalac [46:18] – They were sprinkled throughout and I think we’ve hit most of them.

Craig Cannon [46:20] – We have that last one.

Kat Mañalac [46:22] – This last one is, this is actually from Holly. She wants to know, “Are there any books that you’d recommend that have really helped you along the way or even what’s the most recent book you’ve read that has been illuminating?”

Tracy Young [46:36] – The most recent book I’ve read is Melinda Gates Moment of Lift. I highly recommend it. I loved it. I was crying the entire book. If you’re into books like that of stories that will break your heart and then also just give you hope for the world. I highly recommend that. I read, throughout the years, I read a lot of self help books, actually. What is it, Chicken Soup for the Soul, but not actually that brand. Just like, zen,

Craig Cannon [47:03] – Stuff like that.

Tracy Young [47:05] – Buddhist, that types of books. I don’t know. I’m just into them but I think that’s a preference.

Craig Cannon [47:10] – Okay. Does that like, get you pumped up so you can maintain

Tracy Young [47:12] – no, no, it doesn’t get me pumped up.

Craig Cannon [47:13] – your tense anxiety fill?

Tracy Young [47:15] – I read a lot of poetry as well. Yeah. I don’t know if that’s helpful.

Kat Mañalac [47:21] – No that is.

Tracy Young [47:22] – It something that’s just a matter of preference.

Craig Cannon [47:24] – What kind of meditation? You have a mantra and stuff or what do you, what’s your deal?

Tracy Young [47:29] – What do I do? I sit for 10 minutes only each day, and much harder with the baby now.

Kat Mañalac [47:38] – That makes me feel better.

Tracy Young [47:38] – I try.

Kat Mañalac [47:39] – Because I feel like everyone tells you you’re supposed to get way past the 10 minutes. And I have never

Tracy Young [47:43] – Not that advanced,

Kat Mañalac [47:44] – been able to do that.

Tracy Young [47:44] – not that advanced.

Craig Cannon [47:46] – It just becomes this competitive thing which seems to totally defeat the purpose.

Kat Mañalac [47:50] – Last question, but is there anything, if you could go back in time, to what, 2012, Tracy, what would you tell yourself? What do you wish you’d known when you were first starting out?

Tracy Young [48:07] – To learn to be more authentic earlier. I think for a long time I wanted to, I mean, I worked in construction, and I so desperately wanted to be like every other construction person. I would even smoke cigarettes just so I could be in the construction smoker circle and be like the group. It was so not me. I even went as far as chewing tobacco once and it’s completely disgusting. Smoking’s disgusting too. But that’s what everyone was doing and this is why I sometimes have a potty mouth because I learned that in construction. I learned that language and it’s been incredibly hard to get rid of it. We’re almost going to go through, I think, a whole podcast without me cursing.

Kat Mañalac [48:51] – Wow.

Craig Cannon [48:52] – Uh, that’s incorrect. You’ve definitely cursed already. But it’s cool.

Tracy Young [48:55] – Okay, nevermind.

Craig Cannon [48:57] – I do it all the time, too.

Tracy Young [48:58] – Then for a long time I waned to be, I so wanted to be a good CEO and good founder and I thought it looked a certain way. I would try to be that and it made me really unhappy. At some point, I don’t even know when it happened, but it happened slowly and we change without knowing that we change. I just became more and more and more of myself. And the last few years have been the happiest for me. They’ve been hard. It’s like, have any success at all, it ain’t going to get easier. I’ve just been a happier person because I am who I am mostly on the outside as I am in the inside.

Kat Mañalac [49:33] – Is there a moment that you finally realized, I feel like I’m now myself. Like this is, I’m doing things my own way now.

Tracy Young [49:43] – Yeah. I’m still working on that. I don’t remember when. But maybe I saw it modeled for me. That there are people I respect and love. I like them because there’s no bullshit here, there’s no mask here. They’re not being anyone else other than themselves.

Craig Cannon [50:08] – That’s very wise advice. All right, thanks for coming in.

Kat Mañalac [50:10] – Thank you.

Craig Cannon [50:11] – Thank you for having me.

Kat Mañalac [50:12] – That’s great advice.

Craig Cannon [50:13] – All right. Thanks for listening. As always, you can find the transcript and video at blog.ycombinator.com. Iif you have a second it would we awesome to give us a rating and review wherever you find your podcasts. See you next time.