YC Fireside: Surbhi Sarna and Tracy Young - Founder of TigerEye and PlanGrid

Hi Tracy, welcome and welcome to everybody in the audience as well. Tracy, you are such a legend more broadly and a legend in the female founder community. Certainly, I can't think of anyone better to kick off Women's History Month with.

Thanks for having me! I'm happy to be here. I will warn you, I've either had a four-week cold or I’ve just had a cold every single week these last four weeks. So if I go on mute to cough, it's because I need to hack up something. Not all parents with young children. I'm not sure I've had a few days straight of being healthy since, I don't know, I think it's especially, especially after COVID. I've got like two COVID babies; I have no immune system. Yeah, I have one COVID baby with no immune system.

So Tracy, thank you so much again for being here. I think a large part of the audience is part of the YC community and therefore knows your background quite well, but for those of us joining that don't know, do you mind giving us a brief introduction?

Sure thing! So I was a construction engineer by trade. I helped build two hospital projects around the Bay Area, and then I wanted to solve a problem I was experiencing in the field in that there’s a lot of paper and it's really hard to figure out which is the latest and most current blueprint to build off of. And there’s this massive version control problem. Steve Jobs announces the first generation iPad in 2010, and we launched a company called PlanGrid which digitized the construction record set. We launched on all the mobile devices and mobile platforms first, and we ran that for almost ten years. And then, in between, I had like three kids, I got to work at YC for a little bit, and I decided I was too young to retire. And I've now started a company called Tiger Eye.

And what does Tiger Eye do?

Tiger Eye is still in stealth, but we are building a modern sales software platform for companies and leaders.

Very cool, very cool. Okay, so Tracy, there are some people out there who I think that they may say that we're doing women a disservice even by talking about what it means to be a female founder. Like anytime we get together, we should just be talking about, you know, I don't know, operational challenges and the like and not really focusing on the differences. What would you say to that?

I would say that there is a difference here. I didn't always think that there is a difference between being a female founder and a male founder across so many vectors, that it would be a disservice if we didn't talk about it. Because as we look at the stats, there are clearly problems, and I think the first step to change is acknowledgment, and acknowledgment means we've got to talk about these things. So let's talk about it!

So, like, how does it feel to be a female founder? Like what's the difference?

Well, it starts off by being a girl in today’s modern society. We are getting things like “keep your voice softer,” “try to be smaller,” “don’t be so loud,” “smaller is better” or “softer is better,” “talk ladylike." And I think that that deeply ingrains something inside us both in the individual as well as what is acceptable in society. Then we get to work and we’re told we’re not killers or we try to push projects along and, this has happened to me, we’re told we are too bossy or we’re too freaking aggressive. And I think all of that plays into the stats that we see today, which is the reality is in 2021 female founders only received two percent of all venture capitalist funding. Much harder when I read that; my heart broke. And like the 2022 stats came out, and it’s the same, you know, so unless we think that women suck at founding companies or they just, like, I don’t know, can’t be leaders, something is massively wrong, right? And something needs to fundamentally change.

Right, and you and I have spent time reflecting on this. Where does that fundamental change start?

I think that it starts... I mean, part of founding Tiger Eye for me is activism. You know, even through YC, we get to see so many tens of thousands, hundreds of thousands of brilliant founders around the world throwing their resumes and their applications at us. And even for YC, the percentage of applicants coming in who are female is low, right? And I think for me I wanted to... I hated seeing that. I really did. It's like, where are all the women? And I decided to be part of the statistics, right? If I can just start my own company that at least we get one more, you know? And that’s who I can control.

So how do we change this? It’s like if you are smart, if you hate your boss, if you don’t like how the world is going, if you don’t know that you’re using... If there is just stuff that pisses you off, step up to the plate and build something better. And guess what? You can be your own boss! I think for me it was very clear that when I worked in construction, I looked at, you know, the pile of leaders, and they didn’t look like... it was very clear that they wanted their leaders to look and behave a certain way. I looked at myself in the mirror, and it’s like, I’m never gonna be that. So it’s very clear where my career trajectory is. And then after construction, I started PlanGrid, and I got to be CEO of PlanGrid for almost ten years. Now I get to be CEO of Tiger Eye. Like, you can totally step up and do it, because I’m your example. Like I didn’t go to fancy school, I didn’t get straight A’s, I’m not... never the smartest person in any room. I just didn’t like how construction projects were ran, and I thought that we could build a better solution to help with that. And then we just built it, and then we didn’t stop building it, and then it became a big company, and then now we’re doing the same with Tiger Eye.

Yeah, that’s amazing. And you know that representation matters so much, which is why it’s so incredible that you’re giving us your time today. You know, you’re a mom, you’re an entrepreneur, you have a million different things to do, and like you said, creating one more example of success I think is so important.

So Tracy, one example you gave from an essay you wrote of how a female founder and a male founder might react to something is when you had an executive who basically left their laptop on their desk and walked away. What was that like for you, and how did you internalize it and feel it? And how do you think that might have been different than the way that a male leader might have handled it?

Oh, I don’t know how a male leader would have handled it, but I’ll tell you how I handled it. So my VP of engineering, who I had like a one-hour one-on-one with the day before, and my CFO went out to lunch with for an hour the day before—his peer. Everything was fine that day. Like within 24 hours, I had taken a pregnancy test, and I had been trying to get pregnant for a long time, and I could imagine how happy I was. I was like, “Oh my God, I’m gonna have a baby! This is amazing!” As I’m walking to work in Mission District, I’m like, I’m one of those people who are walking with your phones on, which you never want to do, especially not in San Francisco anymore. I see this email come through, and it says, “My laptop and my keys are in my desk. I’m not coming back.” Like, immediately cancel! And it’s like, wait, I just saw you for an hour, and everything was okay yesterday! Like, am I taking crazy pills here? And by the way, have you heard of like a two-week notice? You know, like you’re just gonna leave your entire team?

And so, you know, I think I think immediately it went very internal, and I started blaming myself, which I think is actually unique to women. I mean, the number of times my incredibly brilliant and talented and, like, confident women friends have, like, took this one thing and then just beat themselves up over and over again over is amazing because, you know, as I said, they’re confident. And so, if they’re doing that and I’m doing that, can you imagine everyone else?

Less than you used to like—do you show yourself more self-empathy than when you did your first company?

Let me think about this. I think I still do it, but I catch myself doing it faster. And then I realize that it’s a complete waste of energy and a waste of time. And then I try to do give myself some self-love or I like go for a walk. It’s like, chill out Tracy, you’re gonna be okay. Like don’t even dare to be unkind to yourself like that. And like I do think this is unique to women that women can be very unkind to ourselves.

Yeah, I completely agree with everyone else, like taking care of everything and everyone and then not taking care of themselves. Come from because I notice it in my friends too. You know, I recently did a post on self-empathy and the reaction to that post was, “Wow, you know, this spoke to me! I do this.” Where does it come from? Is it something society's teaching us? Is it biological?

And what do I think? I'm not an expert here. I would guess if you had a gun to my head and I had to guess, I would say it is both biological, biological that we have evolved to be this way of caring for everything and everyone, and then it must be cultural.

Yeah, yeah, well someone has to keep the human race alive, I guess. And then that ends up—like, young girls are so depressed these days, and like that is definitely cultural. I mean, it's like these things—it's what social media is telling them, how they should look, how they should act, and it's like massively damaging, which I'm really sad about.

Yeah, yeah, me too, me too. So as a second-time founder, you still beat yourself up, you think, but maybe with the same frequency, but then you catch it sooner. That’s the difference, you think?

Yes.

Okay, so any tips for doing that? You talk about that a little bit in your essay too, and I love that, controlling the duration of the emotions instead of having the emotions come up, which I actually think having the emotions come up and confronting them might actually make us better leaders, but controlling the duration of it I think is key.

Yeah, what tips do you have for doing that?

I think it’s totally okay to cry! In fact, I think it’s massively damaging when we try to repress those feelings. So if you need to cry, cry it out! Go take a shower, like give yourself a nice coating of makeup afterwards so you feel good about it, and try to go to your happy place. My happy place is—I love taking walks in the woods. I live in Marin and like there's a lot of hikes here, so just going out, getting some fresh air is like really great for me. For my other friends, it’s... buying! Like I’ve heard they buy the most, like, they buy the most expensive ice cream in town, right? A $40 ice cream sundae, and then they eat all of it, and the next day they go for like a marathon run. So like, you do your thing! You do you! You know what your happy place is and what makes you feel good, go do that and give that to yourself because you deserve it!

Did you know what your happy place was the first time around, or is that something that you cultivated after realizing that you needed it?

Yeah, I’ve always loved trees and like nature, so you would always give yourself a break and yeah, get out into nature.

Okay, that’s great!

Okay, so I’m sorry, you were telling us the story left. So what did I do? Um, the highest of high is finding out I'm pregnant! I'm about to be a mommy. Lowest of lows? I thought I was the worst leader under the sun, like because someone left me like this, right? And then, God, it was—I don’t remember—it was just like really bad for a few days, and then that was it. It's like, all right, game time! You know, war mode, let's do this! And I took over engineering, and I was not the natural one on the team to do that. I mean, like I let every area of the business except for engineering, and which, I’m now very thankful for.

When it is interim, BPES kicked off a search, really got our frontline engineering management together, and then really went in and diagnosed the problems we had. A cultural problem. We never wrote down our engineering cultural values, and there were basically like three separate camps of teams and how they thought about, you know, the standard of engineering at PlanGrid. Some people would self-select out; some people would rise to the top and really, you know, really bring their love for PlanGrid and continue to fight for us and continue to help us fix problems. We took the product roadmap and we blew it up because we couldn’t have 18-month roadmaps. We needed to deliver for our customers and for the business within six months. We blew up the roadmap, came out with new priorities and people just—like a lot of people hated it. They just—like changes really hard, turbulence is really hard. The right thing we did was we did it all at once. So it’s like, all right, it's going to be turbulent anyways, like let’s just make all these changes. Um, and by the way, if there’s like any people changes you’ve been like thinking about, other people not working out, you don’t really know how to do, like this is the time to do it! Just like get rid of them. But not everyone was on board with that, and you know, it sucked. We lost a lot of good engineering managers, we lost a lot of good engineers, good product people, but after that we were a way more effective R&D team, and it had to happen.

Yeah, I love the way that you say, you know, always take advantage of turbulence. That’s such a great thing to remember, I think, as a founder.

So as you came together and discussed these cultural values, what were the cultural values? And did you see change immediately or soon after you took the time to define them?

Yes, and I’m trying to think back at... I mean this is like a few years ago. It’s a long time ago! Um, it had to do with even like the types of personalities that we wanted and how we tested and how we prioritized. So once all that was in place, it was just, um...

Yeah, all right, Tracy! I want to switch gears a little bit and talk about sort of the process of becoming a mom. You know, you took the time to read my book when it was in pre-print, without a doubt! Thank you for doing that! And we talked a lot about decisions I made around my pregnancy and soon after, and these are things that you address in your essay as well, right? You talk about going to give a keynote nine months pregnant, and your water breaking that day. Tracy, would you have given that keynote?

Can I just share my screen real quick? Because this is like just forget, because I actually shared this photo yesterday and I pulled it up. It’s still here. Share screen... can you guys—this is very meta. Select window, entire screen. Can you see this? Can you see me? Can you see me pregnant?

I can’t! I can’t see it.

Oh, failed! You don’t see anything? Bummer, bummer. I’m so pregnant! I’m nine months pregnant at my user conference, and I’m on stage, and I go through 14 hours of the conference and I work the halls like a good co-founder, good host. I go home and I think I’m gonna watch re-watch Game of Thrones and like go to sleep, and my water breaks! And I remember looking at my husband, who’s also my co-founder, and I was like, “I’m too tired to give birth!” And my oldest is not born another 32 hours! So like, you think about the amount of time I didn’t sleep; it was an awful birth. Luckily he was totally safe, etc., but he’s healthy, but that happened.

Yeah, so when you reflect on that time, Tracy, you know, what do you think?

Well, you've done it again! This was such an argument with our marketing team, I remember, because it was our first user conference. It was a very expensive investment for us. We actually got to a big enough point where you can have a user conference and have a thousand of your customers show up. So it was a big deal for us and I remember our marketing team being like, “Yo!” and then, you know, they were like parents. They’re like, “You don’t get to control when you get to have your baby, so you’re going to record your keynote and we’re just going to play it if you’re not here.” And I was like, “No, absolutely not! We’re not going to record it! I'm gonna be there!” And it was so stupidly stubborn about it. But the internal dialogue went something like this: I remember thinking, “Would male CEOs skip their own user conference and not show up at their keynote if their partners were giving birth?” And it felt like—in doing the argument—which is a really stupid argument, by the way—the argument I made to myself was, “Well, if I wasn't pregnant, then I would definitely be at this user conference, so why would I keep myself from going to this conference just because I'm pregnant?” And I was like so self-conscious about being a mom, and that’s all it comes down to. I was so scared of what people might think of me as a mother, that I wouldn’t be able to do my duties as a CEO, which is completely crazy sauce! So I went to my own conference, I gave birth, you know, 32 hours later, and if I could do it all over again, I think for sure, I would have recorded my keynote. I don’t even know if I did or not. I can’t remember anymore. I definitely remember arguing with my marketing team, and they were just like, “You’re stop it!”

Um, and I think if I could do it all over, I’d probably show up for my keynote, do the 15-20 minute talk, and then I’d peace out! I’d go home and rest up and wait for my contractions. I would not have stayed there for another 14 hours.

Yeah, what do you think it is that drives us? What's the underlying feeling, right? Because for me, when I was pregnant, my water broke eight weeks early, and I was hospitalized, and we were losing the baby’s heartbeat. It was coming and going, and I still insisted on making my executive team come to my hospital bed to complete the board meeting we had scheduled. Like, what is the underlying emotion/feeling—fear—that is driving us to make these decisions as first-time founders?

I think maybe because, I mean, you know, society's net is clearly that women aren’t good enough to lead, or else you would see a lot more women leaders across the board. And I think my fear is, I don’t want to validate that. I want to show you that I can do this, even if I’m going to be going through this massive life change. I’m going to show you that I can run my—what is it—a board meeting from your hospital! You’re crazy! Meaning like I’m gonna keep running my board meeting; I’m going to show up at my user conference because I’m not going to give you any excuse to show you that I’m a worse version of a CEO and founder because I have these biological differences than men. And I think it's like really wrong of us to have done that because both of us put our babies at risk. You are lucky your son survived, right?

Yeah, and it’s so scary! And, you know, I think that if we were good role models, we would have taken the time to have these life changes and like these miracles in our life and like let the team take care of everything else. That’s actually real good leadership, is that you’ve put the company at a point where you can step out for three months and take care of your baby and then come back, and the company had progressed and it kept moving on with your vision.

Yeah, I entirely agree! I would have done things way differently, and I think part of it is that when you’re pregnant you’re not a mom yet in a way.

You’re so right!

Yeah! You’re still that, you know, beast of a founder that’s going out there and just making progress. You’re used to pushing yourself, right? It's like we would have never done that with our second pregnancies, and we’re also pregnant for so long, you know. This nine-month pregnancy, so like seven months go by and maybe pregnancy is not so hard for the ones who are lucky. Seven months go by and then eight months go by, you’re like, "Okay, I can still do this," and then you don’t think about that last few weeks, which is really hard. Like the baby is fully baked; it's ready to come out. Um, you know, your cervix is ready to pop out, everything hurts, you’re not sleeping. Like you don’t think about that because you’ve been running for nine months and it’s been fine.

Yeah, there’s like an actual full being in you now! So what would you tell female founders out there who are thinking about starting a family, but they still have that feeling like they have something to prove? You know, to themselves, to others, and they feel that unconscious bias, right? They feel it, and so they're under pressure to do these things, these types of things that you and I did, which it sounds like we both regret that we did.

Yum! Two things. Mostly because I worked in construction and I had worked with a lot of badass construction women leaders who are older, they're maybe boomers, maybe even, and they run construction companies and they had chosen not to have children because it was impossible for them during those times. Like they couldn’t have run a construction company or be a leader in construction firm and be a mom. And it just makes me so sad because like that's exactly the genes we want to keep going on in our gene pool!

Right!

Yeah, absolutely! It’s a good point. I didn’t think about it that way. The first point is if—because this was something I was scared with—like I had basically three, three… I mean I'm like 38 at three geriatric pregnancies! I was like, I remember my doctor was like, “I’m sorry, what did you just say? Did you say geriatric? I'm 35!” And they’re like, “Well, that’s okay, it's normal in San Francisco.”

Yeah!

They're like, um, that for a long time I didn’t think that I could be a founder and be a mom, and I was really wrong about that. It is going to be really hard, but it's totally possible. You do have to have a really good support structure. I have my parents that moved in with me, and they obviously help out with a lot of the household and childcare duties. I also have a nanny that I pay for to help me out with the kids. So you do have to have a support structure to help you do both because it’s just impossible to be a great founder and just a dot have support that way, but it’s possible!

Two, what would I tell people who are thinking about it? To not worry so much! Like you want to work with people who are so excited about you becoming a mom that they're going to support you and they’re going to have your back when you’re on maternity leave. You don’t want to work with people who are going to judge you, and more likely than not, it's probably all in our own heads anyways. That's probably what I would say, and if you do have people who are judging—like I definitely had an exec who called me like the second day after I gave birth to talk about the business. And this was a very, like, low self-esteem self-conscious, like character flaws executive that I needed to fire.

Um, four kids by the way!

Yeah! And it's like, why are you calling me? I’m in the hospital right now! Why do you want to talk about it?

Anyways, um, if you do have teammates like that, like you probably just need to get rid of them.

Yeah! You have your back during like the most important stage of your life.

Yeah, yeah! I mean, if we want to keep Humanity going, that means that when moms are out taking care of their newborns, there have to be other people that step to the plate, you know? So I completely agree with that.

So another part of your essay that I found moving, which I don’t think is quite discussed openly enough, is breastfeeding. And what does it mean to be a founder or a leader while breastfeeding? What does that even—you know, I feel like that's a shock to so many women, right? You get, you know, “Okay, pregnancy is going to be hard, childbirth's gonna be hard,” and then breastfeeding comes along and you feel like, “Why didn’t anyone tell me about this?”

Yeah, it was really, really hard. I mean, like the cracked nipples, the bloody nipples, hungry kid who’s like eating way too much. I think firstly it’s okay if you choose not to breastfeed. As long as you’re feeding your kid, you’re doing a good job! I chose to breastfeed all three of my kids, and it was crazy hard for me, and then there’s like mastitis—is that what it’s called?—like you get this infection? Or most moms who are breastfeeding do for the first few months.

Um, what’s my advice on what is it? What was your question? I’m just...

Yeah, like yes, what is it? What’s the implication on the business, right? Like every three hours, we’re either running to our kid to breastfeed or running to a pump, right? And then the beginning, like two hours, and you wrote in your essay what you didn’t want to use a room at the, you know, you were on Sandhill fundraising and you didn’t want to use like the rooms at the VCs offices to pump so you did it in your car, and then people would walk by, you know?

Yeah, that would be really good with scheduling, you know? You've got meetings, you’ve got work to do, and now you have to build in breastfeeding every three hours into it.

So one, you have to get a lot better with scheduling and more strategic about like what work you can do while pumping milk or breastfeeding a baby. Like there’s certain things where you’re not interacting with people; maybe just like a lot of reading and thinking that you can do during that time. Um, but yes, I needed to fundraise and or at least wanted the option. I wanted a term sheet, so I could have the option. We didn’t end up taking the round, but I was on Sandhill with engorged breasts and I’m going to these meetings asking for $50 million of investment, and I was trying to ask to use their mother’s room. And at that point, like I’m so petite, like I wear a baggy sweater and you couldn’t tell that I had just given birth. So like no one knew I had this newborn at home, and I didn’t want to talk about it. And you know, I felt like if I asked to use their mother’s room, they’re gonna know I’m sleep-deprived as fuck right now, and I just don’t want anyone knowing anything about my personal life. I just want them to think about my business and think if it’s a good enough opportunity for them to invest, right?

So how does one pump milk on Sandhill Road when you’re too shy to ask for their nice-ass mother’s rooms?

Um, because I think, you know, the MeToo movement has really moved all the VCs, at least on Sandhill, to have like very nice mother’s rooms. I would park in front of someone’s super nice home in Palo Alto on like, you know, with like a nice willow shady tree, and then I would just like... no! And then I would forget the refrigeration kit and I would just like dump it out the window!

Oh gosh!

Oh no! Their nice home and then someone's breast milk on the street! Oh geez! I mean, I remember—I remember pumping milk while driving, and I had sort of—I have like a lower sports car, and so when a truck went by, they could see into the window!

Yeah, it’s just the worst! You know, but um, you mentioned that you didn’t want to share anything personal with the investors, and how would you have done this different? Like how would you do this differently today? Would you just communicate what was going on? What do you think?

Yeah, investors! I would have walked in today; I would have walked in and I’d ask, I’d give my pitch, I’d ask for the $50 million dollars, and then I would immediately ask for, “I need to use your mother’s room!” And then I'm sure have been like jaw-dropped just like, “Wait, you just had a baby?” And it’s like, “Yes! And I need to use your mother’s room right now!” And I would just own up to it! Because that would have been a way more authentic pitch and like reality of my life as CEO, and like if they’re gonna judge me for being a new mom, then like fuck them! They don’t get to be part of this investment! I’m gonna like—I’m about to make someone a great return, and like it’s your loss, you’re gonna judge me on that.

Yeah, yeah! I think fuck them is right! I think that’s how I would put it. That would be my advice as well; it’s just they should think that you’re a badass for being able to do both. It wasn’t that right? In my case all the anxiety was all internal, and it was these stories I had made up in my head. I actually think that I’m hoping—and a lot of my friends are VCs, including you—like I’m hoping that there wouldn’t be that judgment, that you actually see it as strength!

Yeah, I certainly do! I had an incredible female founder a couple of batches ago, you know, be pregnant during the whole thing, and she crushed it! She’s doing so well! I did advise her to take care of herself better than I did. I’m not quite sure she listened. You know, it’s just a hard thing when you’re going through it to put the company aside when you’re programmed not to do that, you know?

So Tracy, before we open up to questions, I have one more for you, which is what are you doing differently this time around? You know, it can be more broadly, but also touching upon some of the key takeaways for first-time female founders. Like what are you—what do you think are some of the most important words of advice that they need to hear?

Um, write down what’s important to you. These will be your core values. You have core values. If you don’t like them, burn it down, rewrite them, hire and fire by these core values, because anything less will send the signal that it’s all fucked. And what you want is to when there’s a situation where you don’t know if you should make a decision of X, Y, or Z, that your own team is pulling up the core values and saying, “We’re going to keep it simple because simplicity is a core value, and we’re going to keep the product simple and this is the simplest way for us to go out to market.”

Um, when there is a question about whether to fire someone, you’ll pull up the core values, and it’s like, this person was not wholehearted—that it’s actually really important for all of us to be present here when we are here and to take care of our own personal stuff. So like, you know, decision-making is just—it makes for faster and better decision-making and more aligned decision-making when you have those core values. So that’s definitely something we’re doing differently; their core values are so important to us. It’s just five, and it’s like nothing surprising or revolutionary. It’s probably core values that everyone has, but we’ve had this other doc, and this was very much inspired by a success factors doc, which is our commitments to each other.

Um, and it’s just like, “I will not be an arrogant jerk. I will be a good team. I will be helpful to my—you know, it goes down to I will I will walk it like I talk it.” And then you sign your name on the bottom and like we are committing to working together this way so that if anyone fails on all those values, like someone can say, “Hey, you know, hey dude, we committed to working like this, and now you’re breaking it. Can you please fix yourself or we’re just gonna fire them because they’re like not going to go by the rules that we had set up in the first place in our commitments to each other?”

Um, so core values are so important. Um, I wish I had rewrote them at PlanGrid. We had some! We said, for example, we said that we wouldn’t hire jerks. Um, we did! We kept them! And the signal that I sent to the company was, “Hey, if you perform for Tracy, if you just do your work, you can get away with murder because she won’t fire you!” Right? Um, and that is not the case today at our new company.

That’s fantastic! I think that’s great advice—being deliberate with culture, deliberate with time.

Um, speaking of which, we have a couple of questions in the chat for you. One is, do you have tips for managing time if you’re juggling kids and a startup?

Oh gosh, I suck at time management! I’m so sorry. I don’t have good advice here. I tell you what does kind of work for us is we eat at the same time every single day. The kids nap and go to bed at the same time every single day. Um, bath time is the same time every single day! And what that gives you is blocks of time where you can work because the kids aren’t in your face needing your attention and needing, you know, your love.

Um, so—and we’re ruthless about maintaining that schedule! And it sucks! It sucks to be so inflexible! So there’s trade-offs to it but what it allows for is time for the startup.

Yeah, I can heavily protect family time. Like the team knows when I’m gonna be out! Like lunchtime I get to—I work with remote, like 12 to 1—which is coming up like I’m feeding two kids! Like, well unless something’s on fire and you call me three times.

Yeah, yeah, I love that! Yeah, the somewhat rigid kid schedule is what keeps Rajiv and I sane—just knowing that they’re going to be in bed by eight o’clock, knowing exactly when their naps are, and when it becomes predictable for them as well. That, and it gets ingrained in your family routine. They actually really enjoy that too, so it kind of sort of works out for everybody.

It does! It does become annoying if someone like wants to go out to dinner and they’re like, “Why can’t you just bring your kids at 30 minutes past their bedtime?” Like, I don’t do that!

Yeah! Or like, religious about the schedule!

Yeah, um, and I also love this—everything like, yeah! I just like, you know, unless if I’m going out to dinner, this is like a really good friend of mine that we're gonna make time for. I don’t do—I just don’t do anything else other than my startup and my kids! So that’s the other way is, you just have to be ruthlessly protecting all your time and being so deliberate about it, right? Just because if I didn’t protect time on my calendar, I would just work all the time because I love working. I enjoy working, and there’s so much of it, right?

Um, okay, let’s see! Any advice for women who are fundraising and any resources we should look at for women who are fundraising?

I would say having fundraised and like having fundraised many, many times over the last decade. Um, I would say don’t care so much! I know what the stats are; it doesn't look good. But you can’t believe that it’s against you. You just have to assume that who you’re talking to isn’t going to judge you because they’re probably—the likelihood is they probably won’t, hopefully! But I know what the stats are and it can be really hard to walk in knowing that you might not get investment.

Um, try not to worry about that! Worry more about your business, about what you have to offer, the problem you’re solving for your customer, and literally worry about everything else other than your gender! And, um, Sabina and I are both examples of having gotten a lot of no’s, but there’s also people who believed us and allowed us to get the investment we needed to build a company.

Yeah, I completely agree! I mean, that's part of the problem with unconscious bias being so entrenched, is that if you’re used to being doubted or overlooked, you automatically expend some mental or emotional energy trying to assess out if the person in the room has that bias that exists on top of the fact that you're about to pitch for a ton of money on top of all the operational challenges you have, you know? So I completely agree with you. It’s just that you kind of have to assume that the person doesn’t so that you can be your best self, so you can present your heart out, right?

And I think other good advice—not just only for women—for those who are fundraising is like you’re either in fundraising mode or you’re not. So if you’re in fundraising mode, time box that! You can’t fundraise for a year, and that’s the only thing you do because you have to build your business! And like the better you build your business, the more likelihood you’re going to get a term sheet, so one is like time box it, figure out how to survive without funding, and then just go cast your net wide! Like pitch to everyone under the sun! You’re only going to get better! And then you only need a couple yeses, right?

And then hear the no’s! Is what YC’s really good at! Hear the no’s! Investors are pro at leading you on—um, abusive relationship or something! And it’s like they’re never gonna ask you, like they’re never going to propose to you; they’re just like leading you on because they want the opportunity to fund you later when you have more revenue or whatever it is. And so—but hear the no’s! If they're not offering you a term sheet right then, it's probably a no, and like move on! Do not waste your time on this person again! And by the way, this should be motivation for you to prove them wrong and like make them regret saying—or not saying no to you!

Yeah, I love that! Beyoncé says, “The best revenge is your paper.” I kind of like that quote!

Um, a question from YouTube: What was it like founding a company with your husband?

Oh gosh! Um, that’s a good question! So marriage is really hard, and if you have the option to not found a company with your husband or partner, don’t do it! But Ralph and I are also examples that it can work, because this is like—we ran PlanGrid almost ten years together, and then we chose—we worked at YC together, actually also—and then we chose to start a company together because we like doing it! We’re just a little bit crazy that way!

Um, what that means is we never stop talking about work. That’s really what it’s like! Every romantic conversation ends up being about the startup! So like, if you can suffer that and there of course is like tips on how to make it work, but a clear delineation of responsibility is really important because you never ever want to argue about something and then there’s no decision and you’re still pissed off at each other for it!

Yeah!

Yeah, because there’s enough things on our personal life to be pissed off at each other for, like parents, right? Like, clear domination of responsibilities—I am CEO, he is CTO. For all technical decisions, it’s him! For all business decisions and like vision and strategy, it’s me! And so we, of course, make our decisions together, but at some point it’s never black and white; it’s like somewhere in between, it’s not obvious what decision we should make, and you just look at like who’s supposed to make what decision, then you’re just making it, move on!

I love that! I love that! Yeah, parenting can be pretty bad for a marriage.

Um, another one from YouTube: Do you have tips for finding a woman co-founder?

Hmm, I like that question. I feel like this community—whoever's like watching this right now—I don't know if there’s a list! Um, certainly like just working... like some of my co-founders of PlanGrid were, like, people I had gone to college with, people I had worked with; um, and then a guy I was dating, and I eventually married and had three kids with.

But, you know, I found my co-founders, so I would just put yourself in a lot of communities, and then at some point you’ll deal with someone, and then naturally the conversation is about solving problems and building, and I think that would be your person.

Okay, great. Here’s another one! I really like—I’m going to reflect on this myself a little bit later—but did you eventually accept the labels of aggressive for pushing projects along? And what do you look for in female execs for your team now?

But just the first one, like what do you do? Do you just accept, “Okay fine, call me aggressive?”

Um, I’m a lot better about just like brushing off people’s comments now, so first of all, unless it's someone I would take advice from, I’m not going to take their criticism from. So like if anyone’s calling me aggressive, maybe if it’s someone I take advice from, it’s like I better check myself! Am I being aggressive here? If it’s someone who I’m not gonna even listen to their advice, like I’m not going to take their criticism; I’m just gonna brush it off! It’s like I don’t care what you say!

So that’s number one. What do I look for in female execs on my team? Um, that’s really good! We’re not really at a point where we need execs! Although I have a head of HR—um, I want them, I want them to have, and this is true for all my team members, I want them to have like a really good, I want them to have like raw horsepower up here. I want them to help me solve problems not just in their domain, but the entire business! I want them to have good awareness because we're all working together, and it's just really much more powerful when we’re aware of each other as teammates.

I want them to have excellent communication skills, especially as a remote team. Um, I want them—I want to see low ego, I want to see humility, um, and then I also just want to see like raw potential and talent.

So how do you differentiate between sort of ego and confidence? Like when you say low ego but you also want someone who’s confident, right? So what do you do to differentiate between those two?

I think that for confidence—you can usually tell this just by having an hour conversation with them—that it just comes off naturally, and you should be able to see humility too, because you're gonna be pushing about their experience maybe or something they've built, and the right, like the right pronouns should come out, right? It’s like we—that's the easiest sign is like they’re attributing their success to their own, their team’s success versus like, “I did this, I, you know, I whatever—I—I—I.”

Including stories they tell you. So I think just really quieting and silencing the brain, looking at someone's eyes, trying to penetrate into their soul, and then really just listening to them the entire time without trying to think of the next thing you're gonna say and just like watch their body language. You should be able to tell, um, if you pay attention in our presence where their humility is coming from or where their, you know... I don’t know. You should be able to see someone in an hour!

Yeah, no, I completely agree!

Um, so another question is—Sabina has a book launching next week!

Yes, I do! It’s called Without a Doubt.

Are there other books you recommend we read as founders?

I like reading poetry; it’s like not really helpful. I mean, it’s just like what do you like to read? Some people like to unwind to sci-fi. Um, but as far as like what’s helpful in business, I actually don’t know. I don’t like reading business books; it’s not my jam.

Yeah, I don’t think we need business books either! Sorry guys!

But, um, I’ll say... yeah, I also—I read like epic fantasies because sometimes I just want to escape the current world, you know? So I read all of the Game of Thrones books before I became a show!

Um, and then also there’s books that aren’t necessarily about entrepreneurship or business specifically that I think are really useful for founders to read like Thrive by Ariana Huffington.

Um, it talks about quieting the mind, Tracy! Like you said! And then realizing the dependencies on our phone and how to do time management and sort of the science—both the science and practical tips. So both Thrive by Ariana Huffington and 10% Happier is also sort of excellent because it talks about sort of the importance of meditation and again quieting the mind.

Um, okay! Any last thoughts, Tracy, that you want to share with founders who are just getting started?

It’s hard! It’s hard for all—it's hard! I'm doing this the second time; it’s hard! It’s just hard! So if you’re feeling it’s like it’s hard, I think startup building and maybe life is just like this vacillation of up and downs. So if you’re like at a very low point right now, maybe it's going to get a little bit worse; it's gonna trend up. Like this too shall pass! So keep going!

Great! And then, Tracy, I thought the ending on this one might be a little bit fun! Do you want your children to become entrepreneurs? And if so, how do you foster entrepreneurship?

Only if they want to become entrepreneurs! If they want to become a janitor, I like—they can totally do that! Um, that just better be the cleanest floor they’ve ever—I’ve ever seen in my life! I just want them to be passionate and happy about what they’re doing.

Yeah, exactly! Just put passion into whatever path that they choose, right? It's like the path to happiness, I hope!

Yeah!

Well, Tracy, thank you so much for being here today! This was so much fun! We really appreciate the time and such wonderful lessons for entrepreneurs! And for those of you listening, remember that we do have a fireside with the Ginkgo Bioworks founders tomorrow as well. Thank you so much!

Thanks everyone for listening! Bye-bye!

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