Tracy Young on Scaling PlanGrid to 400+ People with YC Partner Kat Manalac

All right, Tracy, welcome to the podcast.

Thank you for having me!

How you doing?

I'm doing good, thank you.

Cool, so 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?

Oh, you know, 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. I wanted to be a part of that building process, and so your first job out of school was construction engineering.

Yeah, it was a construction engineer. 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 the 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.

Okay, and how did you actually end up picking this idea? Because I've heard several interviews with you, and you talked about like batting around ideas with your co-founder for years before.

Yeah, so my co-founder Ryan Sutton—gee, I mean he just has so many ideas. He knows so much about the world, and he's just an entrepreneur mindset.

Can you share any of the other ideas that did come up?

No, it’s so funny. We were trying to think of all the weird ideas he had come up with. I mean, certainly, he had pitched wanting to start a construction company for several years as we were going through the construction engineering program. The one that comes to mind is cat roulette. We would adopt all these cats, put cameras on them, and then if you wanted to just see a live webcam of cats, you would just like tip them and you could feed them and you could play with them.

Sign me up!

Yeah, so we didn't end up building that.

Okay, and so what was it like? Because, you know, tons of these people, right, they're always pitching startup ideas with their friends. Obviously, this one has more product-founder fit, but what was the reason? I know the iPad was coming out right around the time you guys were starting, but what convinced you, like, okay, this is the thing that I’m going to commit to building?

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 nine hundred million dollar outcome. It was just a fun project, and we started building it. I think when we realized it would become, it was actually, it could be a business was when we sold our first million dollars. It was like, whoa, we did this without a sales team.

How long did it take to do that?

I want to say two years.

So how did you know the co-founding team was the right team that you wanted to build something with long term?

We were all friends. We liked hanging out with each other. Some of us had worked together; two of us were dating, now married with a kid. Three of us had gone to college together, and so we had done projects together. We'd just known each other for a while.

But the story of adding your boyfriend at the time is kind of funny, right? Because like, to my understanding, you were kind of shopping around for a technical co-founder.

Oh, we went through that. You know, the idea of digitizing workflows for the construction industry is a super simple concept, right? Take the blueprints, take the specifications, throw them in the cloud, and make them available on mobile devices, which wasn't possible in 2011. So Ryan had pitched me this idea, and we actually just opened up some blueprints on the first generation iPad on whatever it was—Acrobat Air at the time. This box comes up, and it says "out of memory" because blueprints are incredibly, you know, they're high resolution. They're ten thousand pixels by ten thousand pixels, and the first generation iPad couldn't handle it.

There's this moment where Ryan's just like gasping, and he's like, "We should build this." I was like, "This is actually a really good idea. It would be super helpful." We would go through this period of what Ryan calls the saddest story in Silicon Valley, which is we have an idea and we have no technical co-founders to build it.

I've seen this problem—well, the saddest story of Silicon Valley. So we would go to our friends who are computer scientists and programmers, and we would pitch them on this idea, and they would all say, “This is a good idea.” Our co-founder Antoine, who was a high-frequency trading engineer in Chicago at the time, said, “This is a fantastic idea. You guys should learn how to program.” And we didn’t.

So I ended up telling Ralph one afternoon, actually. We were having dinner, and he, you know, it's at this point in our relationship where our work's going steady, and we’re sharing Google calendars. 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 on the subject peanuts?"

And it's funny you should ask. There's this idea that we have, and he is so offended. He's like, “Do you even know what I do? I'm a full-stack engineer, you know?” Ralph is very confident. He's actually quite talented. It'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?”

It's really funny.

So, he sold himself to you. What was your mentality, to like 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?

You know, I actually still see my—you know, whatever it is, seven, eight years at PlanGrid—I still see myself as an engineer, as a builder, so it was something I liked doing.

Yeah, because that you mentioned earlier, but like the product started selling itself, right?

Yes, I mean, we worked at it, right? We actually had to tell the story, how to show it off, but yes, we had early organic adoption, and we’re very thankful for that.

Okay, because there are a bunch of questions that we saw on Twitter about that exactly. Like, how did you get into— I mean, in the construction industry, especially in 2010, not necessarily like digital native people; they probably don’t have iPads sprayed on the construction site. How did you make your first money?

The first, like, twenty users were people we had worked on construction projects with and then people we had gone to university with, and we would just, you know, ask them to try out our software and give us feedback.

Okay, and then at some point, they would start using the word "love." We’d call them every week. I’d say, “Hey, it’s Tracy, you know, just checking in. How’s the new update going? Did you load it?” And of course, I could tell if they did or not. “Hey, go load, you know, go download the new update. Try out this new feature.” And they would give us feedback over the months, and this is during YC. At some point, people would start using the words like, “No, this is great. I love it.” It’s like, okay, great, that's like note to self. It’s like, alright, someone's going to pay for this very soon; that beta tag is coming off.

And what does the product actually look like at that point because we have so many people that come on the podcast, and oftentimes they’ve, like, they have maybe a successful outcome or at least a product that— you know, like gosh, it was so simple.

For us, what worked out is you have to understand people. We fully understood our users: superintendents, foremen, electricians, carpenters—they have real work to do, and every minute on the job site is money, and every minute counts. So if every minute they’re trying to find information, that 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. So 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. Or if we see people tapping into our app, and it's confusing to them, that was a moment we would change things, right? Because it was all about how fast can they access their information.

And for an industry that has historically used software, there's a certain amount of education that we have to do. It’s not like, you know, I don’t know, the head of HR at some Fortune 500 company, you know, just switching out their HR payroll system where they know what they want and it's just, you know, take this thing and then replace it. For us, we had to even convince them like, "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." And so not only do we have to educate them on the devices, especially in 2012 and 2013, 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. So let’s walk through it actually step by step.

So, all right, give me an example of an early customer that you didn’t know, that you basically had a cold call or maybe you got an intro, but like you had to start from zero?

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's like, "Yeah, that’s nice, but I don’t have, you know, mobile devices.”

And so 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? So for us, we had to remove the friction, the barrier of them not having the hardware to support the software. So we, in 2012, we were giving out iPads away for free. Well, we were actually, no, that's not true—we were loaning them out to them.

Okay, mm-hmm.

And then eventually, we would just basically charge them enough money to cover the hardware costs.

Yeah, and then did you sort of have to sit down with each one of them and walk them through, you know, going to the app store, you know, typing in their password, setting up their...?

Exactly, because we knew it wasn't going to happen. 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 the work with them until they got their project into PlanGrid and started collaborating on it.

Yeah, because it’s interesting because many of these other software products, like GitHub, go with this bottoms-up method. Did you ever entertain that idea, or was it always like we need to get this foreman or whatever? I don't know if the hierarchy—but like a certain level of person, and then go down from there?

If I understand your question correctly, I think we did go bottoms-up. So we went directly into the field, which is normally not where software is sold because construction software has existed for thirty-some years.

Oh, I thought you were going up to people who are managing, yes sir.

So construction software has existed for decades, but the hardware didn't exist to bring it out into the field where 98% of construction happens. And if you're writing software for the construction industry, like in the 1980s, you were writing it for people in the office—the enterprise buyers: CIOs, VPs of Operations, etc.—and then they would deploy it. Maybe there's kind of 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 a 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 like customized versions, free, you know—we're talking about 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 project, whether it’s residential or commercial, or a road or a bridge.

But what you're describing is now like a giant enterprise product, right? So how do you go about product development in there?

It was simplicity. We asked ourselves, what is the one thing everyone needs to do, which is access the construction information? The first thing we did was 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 Android and Windows, etc.

And in terms of product development, were there any—so that’s obviously a huge breakthrough, right? Like, early days, you load this file on the iPad, it crashes.

And so that’s amazing. You get people with—were there any other product breakthroughs that let a lot of growth through a lot of sales for you guys later down the line?

Yeah, I'll talk about some of my favorite features inside PlanGrid. Sometimes you want to look at your equipment drawings, you know, just different equipment 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, right? Or maybe it’s, you know, medical equipment at which point it needs med gases and plumbing, etc. So 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.

So we, I don’t know, 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, a new version. If you guys are following, you can see what changed from this version into the next, and then just highlight in red. So 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.

Bring up...

Yeah, so you can imagine it's like—and there’s always like a certain thing like magnetic door hold openers. You know, sometimes you open up a door and then it slowly like closes, holding—they only occur on maybe five sheets out of 5,000. So either you haven't memorized or you're searching through sheets all the time.

So with PlanGrid, you can search for the word magnetic, and then it'll pull up the five sheets you’re looking for, which was not possible before, certainly not when I was in the construction industry.

And so this is super useful for someone like doing inventory and ordering, just looking up information and figuring out how to build it, planning, ordering, yeah, exactly, doing estimates.

It's super useful. I mean, one of the early features we released was version control; that felt revolutionary.

Yeah, well, that's like my understanding, Ralph was working a little bit of picture, right? Because that’s—as someone personally who, like, does...

Which of my amazing founders built it?

But yes, it’s not the team that built it for PlanGrid engineering. It wasn’t just about providing access, right? I think I sold it short. It wasn't just about providing access to the information. It was, how do we take technology that exists in the world and apply it to the construction industry, specifically on the construction recordset?

So, you know, machine learning is the thing; we were doing it before it was cool. We could 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. So it’s like a 101 first floor floor plan. The next time someone uploads a 101 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, you know, was it was a sheet-based system?

It wasn't a follow-based system, right? Which becomes super important when you're printing out these layouts for people, and then they take them on into a building, and then they're operating off of an old plan.

Exactly, which is actually probably the cause of a lot of—I mean, there’s been studies on this, it’s like it costs the U.S. construction industry 20 billion dollars a waste every year because they have to tear it down and rebuild.

Yeah, yeah.

Wow, that's—well, yeah, so thinking back to your time at YC, is there any specific advice you've got from any of the partners or anything you learned during that time that stuck with you today?

Oh, you know, I feel like all of the speakers who came through dinner, one of their advices or their lessons was it’s like not firing people fast enough.

And would it—would not only, you know, not only did you have the wrong person in that role, but it would completely—their blast radius is too big, so it would, you know, it’s always someone of leadership.

It would affect everyone around them, right? Because when someone’s not working out, everyone else knows, and then, you know, the CEO knows. It's tough advice to process at the time because you didn't have any employees.

No, but yes, but certainly we heard that so many times, and I think like almost every single speaker just talked about it.

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, right? You put the wrong person in the role.

And I say you as in like me, and then there’s—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, so it’s just bad on all levels.

And so my advice would be, yeah, right people on the bus, wrong people off the bus as soon as possible.

So how do you do that?

You know, I think one is like it shouldn’t be a surprise. I’ve certainly made this mistake many times, and I like 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.

Right, awful.

So I would say the moment that we figure out someone isn’t working out, timebox it. It’s like, “Oh, but there's always some excuse, right? You know, but I just don’t have time. They’re like pretty good. They're performing mitts like net-net, is it positive or negative?” It’s, you know, it’s negative; they need to be out of there.

And timebox it. We’re gonna, you know, let them know this isn’t working out, and you 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.”

And that is the most—that is what you owe your team member, right?

So now, how many people are PlanGrid?

PlanGrid is 450 people.

Okay, and growing. We are now part of Autodesk's construction solutions team, and there are 1,200 people altogether. So that includes PlanGrid.

Okay, and then the other products about it, and then, you know, 10,000 other people in design restructuring. So related to firing people, as hiring people now that you’ve hired 400 plus—well, not personally, but, you know, PlanGrid in general—what are the most important things you look for so you don’t have to fire someone?

So, early on, when we were sub-50 people, what we were looking for were people who had high pain tolerance and people who could be generalists because we had to—there’s just too much work to do.

And so how do you do all the work as five people? Well, those five people have to wear multiple hats, and they had to not complain about it. You know, there’s work like, you know, taking out the garbage because you probably don’t have an office manager or facilities team, and then also code.

And so those would be the two traits that I would look for 7-50 years. At any size, 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, you just have to start specializing. One person has to be charged with 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, you know, segment it out that way.

The other thing I look for is—in later-stage and later-stage startup, you know, I’m counting as I’m drawing the line of 50 people, especially looking for leaders—I would look for people who are just authentic. 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 it’s like, do you really want to work with someone who’s bullshitting? Probably not.

Well, my impression is that executives get very good at interviewing.

Do you get?

But you can also you can just sense it, like, personally. 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, you know, fine. Or are they making themselves sound better than they actually are?

And this is where reference checking helps.

Yeah, doing lots of reference checks, looking for someone who’s authentic. And then the other good indicator for success for that rule is, have they done it before? And how have they done it successfully?

Mm-hmm. That’s a clear metric; that’s a great one.

But like authentic pain tolerance, I mean generalist—well, it’s harder to judge, and it's more easily—it’s more easy for bias to slip in, right?

Swimmers like, “Oh, you know, Cat, like I interviewed with Cat and Cat's like, ‘Craig seems authentic,’ but then someone else is like, ‘Craig's totally bullshitting me.’” So like how do you make that concrete in an interview process?

I think it's much easier later on because you just have more team members and more eyes and more, you know, meters going off, not going off.

And early on, I mean, early on, like who wants to join our little startup, right? Like, "Yeah, what is PlanGrid? Yeah, what do you mean you're writing software for the construction industry?"

And it’s just basically, you know, the first ten people were people we had worked with before who were our friends or, you know, fresh out of college, and it was the only job they could get.

And so, um, I don’t think you have a lot of luck. We didn’t have—we certainly didn’t have that luxury early on.

Okay, to try to filter people that way.

Ryan, my co-founder’s test was like, I mean, if we didn’t have the luxury of having an option to like great candidates, I think his test was, who would I rather be stuck on a cross-country train with?

I think that was a trained early car, like a longer who would I rather be stuck with.

And that’s how we made decisions.

Yeah, I think people have different ratios of like how much you get along with versus how competent they are.

This is everything given equal, and yet they choose—oh yeah, but and then pain tolerance, too, just like, because so many people listening are looking for like concrete—

Yeah, yeah.

So, you know, we would put ourselves in their shoes, too. People come to mind, Taylor, who was canvassing. You're going door-to-door canvassing and getting no’s and like, you know, Kirsta in door shut, like, you know, probably high pain tolerance.

And spoke of it, you know, passionately write a psalm on—was literally a door-to-door pencil salesman.

Wow, we're like Staples or something in America?

No, no, these are modern tunes.

Yeah, in modern times; I don’t know when we met him—2014 or 2015 maybe.

Whoa!

And he was selling pencils. I was like, you know what, I think you're gonna do great making phone calls to the construction industry.

Yeah, you know, like high pain tolerance—that’s what I mean. You can tell by their backgrounds.

Okay, and then someone who went through all of that but still speaks very positively, you know, looking for—like you can teach a lot of things, but teaching someone to have a positive attitude, you can't teach that.

You either have it or you don’t.

And like when we spend so many hours in a day at work, especially when there's always problems, yeah, and it doesn’t always feel good having those positive people is like really nice actually, yeah?

Especially when they're, you know, doing just as much work as everyone.

I'd much—you know, who wants to be around negative people? Let’s face it, no one.

But the negative people exist, and, um, I don't know, feed them chicken with some sugar.

That’s not good advice.

I don't know, I guess I’m just saying if you have the option, like, yeah, no way, way a positive person a bit higher, yeah?

Well, especially in the early days, right, when they’re foundational and can influence like the other people you hire.

Yeah.

So to sidetrack 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?

No, he was thanking everyone for working really hard and like working nights and weekends to roll out everything before WWDC this week. People pushed back because they’re like, “What? This is like not fair.”

You know, this massive company promoting a work-life balance that might not be actually stable or maybe good for the world.

I have my own opinions there, but like how do you feel about like creating work-life balance at a high-paced startup, rolling out important products?

I feel like it’s just what gets elevated, right? 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.

And so 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, you know, in terms of like 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 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, especially now—I mean we have so many—it's funny because, you know, when we were like in our mid-20s, early PlanGrid, it seems like the only people that wanted to work for us were people around our age.

And so as the years gone by, you know, myself included, there's just more gray hairs in the building, and so what that also means is there are people with children and grandchildren that work for our company now.

And like, yeah, they are probably way more important than me.

Yeah, yeah, sure!

And we'll, 'cause I’m on Tim Cook's side because I'm like, listen, the reason why they're so important and the reason why the office matters is like people do put in that work—I care a lot about it, and I think that's great.

It's important to acknowledge that.

Yeah, absolutely! Like, I like being thanked for when I work hard, you know?

Right, and so like, so what you’ve done now is, he’s never gonna say it again, but people are still gonna work.

Mm-hmm.

Like, it’s not realistic. So someone did send a question related to this. So Freddy Fernandez asked, “How do you track the wellness levels of your team or do you?”

I don't think we do. You know, we are office managers, and facilities managers, they do a really good job of like taking care of the team.

I remember, I do remember a funny story. Remember early days, um, 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 like lotion diet and so cokes would show up or donuts would show up, and early on, I’m like, “What is this? You guys can’t eat this; it’s bad for you.”

Um, you know, I'm less crazy about it just because there’s so many people, it’s like, “I don’t know who brought in the donuts this day, but it came from a good place.”

Right? Mature Tracy, at what point did it become, you know, you have a team now whose job it is to take care of the team versus like, at what point did a transition away from your responsibility?

I don't know. It's such a blur in a days, you know, like seven, eight years at PlanGrid going from five co-founders to four hundred fifty people and now a lot of revenue. I want to say a hundred fifty was when everything broke, right?

Done something like Dunbar’s number, and everything is complete chaos. I’m gonna say if I were to best guess, probably about 150 people was when we had like an office manager taking care of all this stuff.

Yeah, maybe before that I don’t remember.

Hmm, so I’ve had the pleasure of kind of seeing you since I think I met you initially in 2013, so I've kind of gotten to see you as a person as your company has been scaling.

And so one question I have is, what are the things that you’ve done to take care of yourself and your own, you know, you and Ralph, your family as PlanGrid’s gotten bigger and bigger?

Other than eating very healthily, what were the things I started doing? Um, I started doing yoga weekly. That was really helpful. As part of that, I also meditate. That was really important. It was life-changing actually for me, just being able to quiet my mind down and then just have a reset and be able to look at things in a different perspective.

Of course, I still am very terrible at meditation, and it's really hard to quiet our very busy human minds.

And 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 seems to help.

Um, I drink a ton of water, a ton of teas. So I think between yoga, meditation, eating well, and that’s a plant-based diet for me, taking vitamins, and then probably not drinking so much.

Yeah.

You know, other things.

What about—in terms of, we talked about this as much or as little as you want—maintaining a relationship with a co-founder?

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, and I'm sure he would say the same.

But it is complicated, so I would say if you had the choice, like you just wouldn’t risk your relationship in that way. But 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, and 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, and when it came to business decisions and just leading the team, he gave me, you know, I was CEO of course, and I don’t know, 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 gonna lead the team.

And so that’s helpful when it’s like a co-leading situation. I think that's where it gets complicated.

Mm-hmm, and then what about at home? Just like, does it all flow into one thing?

Oh, we also have rules. You know, it’s like after 8 o'clock, let’s not talk about work, but we broke that rule all the time.

We still continue.

Okay, and so, yeah, you mentioned this, but you’re also a mom now. What was that process like when you’re managing this giant—

Giving birth?

Yeah, but you talked about like fundraising all this stuff last year. So my baby is gonna be a year old next week.

Um, last year was nuts; it’s a blur for sure, mostly because I was sleep-deprived, you know, like all parent—new parents—God!

What is your question?

How just tell you about it? It was just like, I don’t know.

Like, you know, you're managing this big thing, but you're also going through just this huge life experience. Like how do you—I don't know.

Yeah, I get, um, there was a woman once who asked me, she was okay, can you—she was pregnant and she was looking. She was thinking about raising for Series A, and she was like, do you know anyone who’s ever been pregnant and raised a Series A?

And I really struggled, right? I was like, I don’t know. I can introduce you to some, you know, I can figure it out, but I guess, yeah, is there any advice for women who are founders of companies or thinking about starting a company, and like balancing having a kid and also taking care of this other kid, which is…?

Yeah, yeah!

So I think first off, it’s totally possible, right? I was leading our team, I don’t know, you know, however much revenue we signed us up for that year and hitting our target. It’s leading a team of over 400 people, parallel pathing conversations with our now employers, Autodesk, as well as a Series C.

It’s total, and then also, you know, obviously the getting pregnant and like growing a kid and then giving birth and then nursing—although 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 mean, I’m just a little bit crazy, so it’s like I don’t know if this is good advice. What I do want people to know is that it’s possible. You just find a way to do it.

Yeah, I remember at some point last year, like during all this, Ralph was like, “Hey, I found your theme song!”

And we’re driving home, you know, I’ve had a pretty hard day, pregnant, of course, with my hard day, and he turns on Drake’s "Non-Stop." If you know that song—

I don’t know that, so let’s check it out!

Cool!

All right, let’s talk about some other stuff. So in terms of scaling the company, someone asks a question about SIA debarry asks, “What’s your big plan to scale from one and a half million to ten million projects?”

So is that an accurate metric? Is that a public metric, how many projects?

I think so.

Okay, how do we get to every single job site in the world? International is gonna be key here, and so we’re certainly putting a lot of our energy and efforts and resources on our international strategy and are investing in our international team and contra-fiying our product so it’s ready for those markets—that’s it.

I’ve got to figure out where the TAM is, and it's the rest of the world.

Okay, and is that gonna mean like—well, is Autodesk international? 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 figured it out, and now we’re bringing PlanGrid to them.

Okay, cool!

Another scaling question. Holly asks, what has been your single largest influence in helping you scale?

Yeah, how do you make it happen? So I’m obviously a first-time CEO, although now I have some experience—seven years of it—figuring out where I’m weak, which was all over the place: finding leaders who had done it before, and surrounding myself with experienced 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, and all of them are still here at Autodesk right now.

How’d you close them?

How did I close them? Yeah, 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, putting and shining on my selling shoes.

Okay, and I think also just being authentic, like 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, how often did you—did you meet an executive that, sorry, we just had a hiring conference last week and I’m just like thinking about how did you meet an executive that on paper you thought would be really good and then didn’t end up being what always looks good?

Okay, especially marketing executives. This is their job, polish. It’s hard to know, you know, I think we certainly had misses, and 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 because it’s painful at this size. You don’t have like 50 recruiters helping you recur; we have a much smaller recruiting team, etc., etc. That’s when we got it wrong was when we got the wrong notch in terms of scale.

Okay, and then personally for you, when you were scaling, what skills did you really have to work on the most to make it work?

This entire journey is hard, and it's hard in a way where it’s hard to explain, right? 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, and there’s all this pressure.

And there’s more pressure if you have any success at all. And then 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, and so 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?

Yeah, however you make that happen.

So were you—did you have a different personality type before you started meditating?

Are you like—you're a pretty chilled person, seems like.

Thanks! Thanks for thinking I’m a real person chill.

Please spread that rumor!

What’s your reputation like?

Hi, strong!

No, just like you’ve an intensity, certainly.

Oh, intense, but yeah, it’s like—maybe it’s like a duck, though, right? You’re doing this under the water, but like you do have an external calm.

Yeah, yeah.

Thank you for that!

But you know, how did you cultivate that, right? Cause like we’re all emotional, maybe to different degrees, but like you know, what do you do?

I don’t know if that’s like—I think it’s just like my personality! But certainly, like, okay, when I'm really stressed, maybe this would be helpful.

When I'm super stressed and things are going bad, how do I make it seem like I'm so confident about the direction of the company?

And gosh, I mean, it certainly doesn’t come naturally, right? And I’m not saying that I'm faking it 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, and I believe that today even more so.

I think—and then also believing that our team was a team to bring this product to our customers that—We love builders, you know? We're working to come from building backgrounds. A lot of our team members have family members in construction, and we cared—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.

Yeah, it’s challenging; something's all-consuming, but you have like a larger mission, you know you need to stay positively.

So I guess what does that boil down to? Maybe passion and love for what you're doing is picking the right thing, right? Because things are gonna go bad all the time, and it’s gonna feel bad all the time.

And when it’s not feeling bad, it’s feeling pretty good; it’s probably because something’s really bad is happening right now.

And you're about to feel like—that makes sense to me.

We see a lot of people, you know, start companies and realize that the customer they’re working with—like they don't really want to work with customers or solve problems for that customer.

But that seemed to be like the North Star for you—like you really understood that your customer, you were passionate about helping them solve your problems.

Stop! I think it boils down to passion, yeah.

So now that you’ve been doing PlanGrid for quite a while 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?

Oh wow, that's a really good question. So we talked about firing; yeah, we talked about managing people so that, you know, when you do fire them, they know it.

What are other things that startups get wrong?

I think that for founders, certainly for me, at some point, I wanted—I wanted to just, you know, if things aren't going right, and 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. And so 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, and is this the right thing? Or are we thinking bigger for the company and the people who work in it, and are we thinking bigger for our customers?

And then also—also do not lie to ourselves. I think that’s something we got wrong as well. You know when things aren’t going right, or you know when things were going right, and you know, can we push ourselves harder?

No, you know, whatever the reasons is, we just have to—I think this is true for just our own personal lives as well—just to make sure we’re looking at things honestly.

And I mean, you’re like—you’re nodding. You don’t lie to yourself.

So many people have different methods of like achieving that mirror, right? So like what did you—did you have a coach? Is it meditation? Is it having a partner that you can also talk to about work?

Like you had a coach named Straat; he was important in my growth as well. He—one of the most important things he taught me was to—it’s funny he told me that I didn’t have very—for someone who doesn’t have very much ego, you have a lot of negative ego.

And I was like, what the hell does that mean?

And I was constantly—I don't know if it’s just like my personality or if it’s just the thing that women do, especially—just like put ourselves down.

You know, we felt so guilty about the mistakes that we were making instead of focusing on like making it better, acknowledging the mistake, and then changing it.

I would just beat myself down, and like it's completely crazy.

I remember I would slik before every board meeting—I would just have this thought that goes through my mind—and I told you this, Cat, where I thought I was gonna get fired from my board.

And I remember like actually letting that slip to my board director, Carol, before a board meeting. I was like, “I—you know, he’s gonna fire me!”

And she laughs in this loud cackle, almost like, “Are you out of your mind?”

Yeah, wow!

Okay, yeah, the business was doing well, the team I think loved me almost the entire time, and we were recruiting. We weren't making that many mistakes, and yeah, that was a thought that went through—

I think right before every board meeting, leading up to it, I would have this thought cross my head.

No, but it’s so hard because you could just get trapped in the stuff in your mind, and you don’t even realize you think everyone thinks the same way, and that's not—that's where meditation helps—is still like just clean out a little bit of that clutter.

And I know, Cat, you had a bunch of other questions you want to—

I had, they were sprinkled throughout, and I think we've hit most of them. I mean, had that last one—this last one 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?"

The most recent book I’ve read is Melinda Gates’s "Moment of Lift." I highly recommend it; I loved it. I was crying the entire book, so if you’re into books like that of just, like, stories that will break your heart and then also just give you hope for the world, I highly recommend that.

I read, you know, throughout the years I read a lot of self-help books actually like, you know, what is it? "Chicken Soup for the Soul," but not actually that brand—it’s just like Zen Buddhist, that type of books.

I don’t know, I’m just into them, but I think that's a preference.

Okay, that like gets you pumped up and see—fill, I read—I read a lot of poetry as well.

Yeah?

Yeah, it’s just a matter of preference.

Okay, what kind of meditation do you do? You have like a mantra and stuff, or what are you—what's your deal?

What do I do? I sit for ten minutes only each day, and it’s much harder with a baby, you know?

And that makes me feel better because I feel like your supply—everyone tells you you’re supposed to get way past the ten minutes, and I’ve never been able to do that.

Totally defeats the purpose.

And so maybe last question, but is there anything—like if you could go back in time to like what? 2012, Tracy—what would you tell yourself? What would you wish you'd known when you were first starting out?

To learn to be more authentic earlier. I think for a long time, I wanted—I wanted to just, you know, I wanted to be a young man working in construction and I so desperately wanted to be like every other construction person, and I would even like smoke cigarettes just so I could be in the construction smokers circle and be like the group, and it was so not me.

I mean, I mean like when as far as like chewing tobacco, no, I completely—does nothing; smoking is disgusting to me.

Yeah, but that was what everyone was doing, and you know, and this is why I sometimes have a potty mouth, because I learned that in construction. I learned that language, and it's been like incredibly hard to get rid of it, and we're almost gonna go through, I think, a whole podcast without me cursing.

Wow!

And then for a long time, I wanted to be—I saw to be a good CEO and good founder, and I thought it looked a certain way, mm-hmm.

And I would try to be that, and it made me really unhappy.

And so at some point, I mean, I don’t know when it happened, but it happened slowly. We change without knowing that we changed.

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; look, it’s like, have any success at all, it ain’t gonna get easier.

I've just been a happier person because I am who I am, mostly on the outside as I am on the inside.

Is there a moment that you finally realize you're like, "I feel like I've like I'm now myself—like this is—I'm doing things my own way now?"

Yeah, I'm still, you know, I'm still working on that, right?

I don't remember when.

But maybe I saw it modeled for me that there are people that I respect and love. It's like, you know what? They’re—I like them because there’s no hair and there’s no masquerade.

They’re not being anyone else other than themselves.

That’s very wise advice!

All right, thanks for coming in!

Thank you!

Thank you for having me, that’s great advice!