- Tracy, a legend in the female founder community, discusses the challenges faced by female founders
- She talks about the differences and societal expectations placed on women in modern society
- Tracy highlights the lack of funding for female founders, with only 2% of venture capitalist funding going to women in 2021
- She emphasizes the need for change and encourages women to step up and build something better
- Tracy shares her personal experiences as a female founder and the internalization of blame and self-criticism
- She discusses the importance of self-empathy and not being unkind to oneself
- Tracy acknowledges that women often prioritize taking care of others over themselves, and questions the origins of this behavior.

- The speaker believes that the caring nature of women is both biological and cultural.
- They discuss how social media and societal pressures contribute to the depression of young girls.
- The speaker advises allowing oneself to cry and finding a happy place to cope with negative emotions.
- They talk about their experience as a second-time founder and how they learned to catch negative emotions sooner.
- The speaker shares their experience of becoming a mother while running a company and the challenges they faced.
- They mention the importance of defining cultural values within the company and making necessary changes.
- The speaker reflects on a decision they made to give a keynote while being 9 months pregnant and how they would have approached it differently.
- They discuss the underlying fear and pressure that drives women founders to make certain decisions.

- The speaker discusses the societal bias against women leaders and the pressure to prove themselves despite biological differences.
- They regret not taking more time off and allowing their teams to take care of the company during maternity leave.
- The speaker emphasizes the importance of having a support structure in place when balancing motherhood and entrepreneurship.
- They advise not to worry too much about judgment from others and to surround oneself with supportive colleagues.
- Breastfeeding while being a founder or leader is challenging, requiring careful scheduling and strategic planning.
- The speaker shares personal experiences of pumping milk in their car and facing difficulties in finding appropriate spaces to breastfeed during business meetings.

- The speaker reflects on how she would have approached pitching to investors differently if she had the chance, emphasizing the importance of authenticity and not being judged for being a new mom.
- The speaker and the interviewer discuss the importance of core values and commitments in building a strong company culture.
- The speaker shares advice on time management when juggling kids and a startup, highlighting the benefits of having a consistent schedule.
- The speaker gives advice to women who are fundraising, encouraging them to focus on their business and not worry about their gender. They also suggest time boxing fundraising efforts and being open to hearing "no" from investors.

- The speaker advises not to waste time on potential investors who do not offer a term sheet immediately
- Founding a company with a spouse can be challenging, but it can also work with clear delineation of responsibilities
- Tips for finding a woman co-founder include putting oneself in various communities and seeking individuals who naturally engage in problem-solving conversations
- The speaker brushes off criticism from people they wouldn't take advice from
- When looking for female executives, the speaker values raw horsepower, awareness, communication skills, low ego, humility, and potential
- The speaker recommends reading poetry and epic fantasies for relaxation, but not business books
- Starting a startup is hard, but it is a journey of ups and downs that will eventually pass
- The speaker wants their children to pursue their passions, whether it is entrepreneurship or any other career path.

- Tracy, a prominent figure in the female founder community, discusses the challenges faced by female founders and societal expectations placed on women.
- She highlights the lack of funding for female founders, with only 2% of venture capitalist funding going to women in 2021.
- Tracy shares her personal experiences as a female founder, emphasizing the importance of self-empathy and not being unkind to oneself.
- She discusses the impact of social media and societal pressures on the mental health of young girls.
- Tracy reflects on her experience as a second-time founder, balancing motherhood and running a company, and the importance of defining cultural values within the company.
- She emphasizes the need for a support structure when balancing motherhood and entrepreneurship and advises not to worry about judgment from others.
- Tracy shares personal experiences of breastfeeding while being a founder and facing challenges in finding appropriate spaces to breastfeed during business meetings.
- She discusses the importance of authenticity and not being judged for being a new mom when pitching to investors.
- Tracy gives advice on time management when juggling kids and a startup and encourages women to focus on their business and not worry about their gender when fundraising.
- She recommends finding a woman co-founder by engaging in problem-solving conversations and values specific qualities in female executives.
- Tracy suggests reading poetry and epic fantasies for relaxation and reassures that starting a startup is a journey of ups and downs.
- She wants her children to pursue their passions, whether it is entrepreneurship or any other career path.

Tracy first went through YC in Winter 2012 with her company PlanGrid, a construction software company that was sold to Autodesk for $875M. She joined YC as a Visiting Partner before launching her second company TigerEye. Tracy and Surbhi will talk about some of the themes that come up in Without a Doubt – from overcoming imposter syndrome, to building a team and company culture, and how to redefine “work-life balance”.

Chapters (Powered by https://bit.ly/chapterme-yc) - 
00:00 - Intro
03:01 - What's It Feels to Be a Female Founder
06:53 - Male vs Female Leader Reaction to a Situation
10:56 - How to Stop Being a Woman
12:41 - High and Lows
15:01 - Cultural values
19:22 - Underlying emotion - Feeling fear
22:30 - Starting a Family
26:03 - Being a Founder While Breastfeeding
29:48 - Discussing Personal Matters with Investors
31:41 - What Are You Doing Different For Your Next Company?
34:44 - Q&A - Manage Time With Kids
37:07 - Fundraising Advice
40:16 - Start a Company With Partner
42:45 - What Do I Look For In Female Execs?
45:50 - Books
47:19 - Last Thoughts

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.

I will warn you, I've either had a four-week cold or I've just had a cold every single week these last 4 weeks.

So if I go on mute to cough, it's because I need to hack up something.

I'm not sure I've had a few days straight of being healthy since, I don't know.

I think especially after COVID, I've got like 2 COVID babies.

Yeah, I have 1 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?

So I was a construction engineer by trade.

I helped build 2 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 and We launched on all the mobile devices and mobile platforms first.

I got to work at YC for a little bit and decided I was too young to retire and I've now started a company called Tiger Eye.

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

So Tracy, there's 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, I don't know, operational challenges and the like, and not really focusing on the differences.

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.

It's crossed so many vectors that it would be a disservice if we didn't talk about it.

Because as we look at the stats, there's clearly problems.

And I think the first step to change is acknowledgement.

And acknowledgement means we've got to talk about these things.

So like how does it feel to be a female founder?

Well, it starts off By being a girl in today's modern society.

We are getting things like Keep your voice softer like try to be smaller like don't be so loud smaller is better 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 fricking aggressive.

I think all of that plays into the stats that we see today, which is the reality is in 2021, female founders only received 2% of all venture capitalist funding.

My heart broke when I read that, my heart broke.

And like the 22 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.

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.

And I think for me, I wanted to, I hated seeing that.

If I can just start my own company, then at least we get 1 more, you know, and that's who I can control.

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 like the product that you're using, If there is just stuff that pisses you off, step up to the plate and build something better.

I think for me, it was very clear that when I worked in construction, I looked at the pile of leaders and they didn't look like it was very clear 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 going to be that.

So it's very clear where my career trajectory is.

And then after construction, I started Plangard and I got to be CEO of Plangard for almost 10 years.

Like, you can totally step up and do it because I'm your example.

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 now we're doing the same with Tiger Eye.

And that representation matters so much, which is why it's so incredible that you're giving us your time today.

You're a mom, you're an entrepreneur, you have a million different things to do.

And like you said, creating 1 more example of success, I think it's so important.

So Tracy, 1 example you gave from an essay you wrote of how a female founder and a male founder, or 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've been different than the way that a male leader might've handled it?

Well, 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 1 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.

That like within 24 hours, I had taken a pregnancy test and I had been trying to get pregnant for a long time.

I was like, oh my God, I'm going to have a baby.

As I'm walking to work in Mission District, I'm 1 of those people who are walking with your phones on, which you never want to do, especially not in San Francisco anymore.

This email came through and it says, my laptop and my keys are in my desk.

And it's like, wait, I just saw you for an hour and everything was okay yesterday.

And by the way, have you heard of like a two-week notice?

You know, like you're just going to leave your entire team.

And so, you know, I think immediately it went very internal and I started blaming myself, which I think is actually unique to women.

The number of times my incredibly brilliant and talented and confident women friends have took this 1 thing and then just beat themselves up over and over again, over, is amazing.

And so if they're doing that and I'm doing that, can you imagine everyone else?

Do you show yourself more self-empathy than when you did your first company?

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 give myself some self-love or I go for a walk.

Don't even dare to be unkind to yourself like that.

I do think this is unique to women, that women can be very unkind to ourselves.

Everyone else, like taking care of everything and everyone, and then not taking care of themselves.

I recently did a post on self-empathy and the reaction to that post was well, you know This spoke to me.

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

Well, someone has to keep the human race alive, I guess.

that young girls are so depressed these days.

I mean, it's like, it's 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.

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.

We can't stop ourselves from being human.

But we can shorten the duration of negative emotions.

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.

In fact, I think it's massively damaging when we try to repress those feelings.

Go take a shower, Give yourself a nice coating of makeup afterwards so you feel good about it I'm gonna try to go to your happy place.

My happy place is I love taking walks in 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've bought the most, like they buy the most expensive ice cream in town, right?

This is like a $20 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.

And 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 get out into nature.

Okay, so I'm sorry, you were telling us the story.

The highest of highs, 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, because someone left me like this, right?

It was just like really bad for a few days.

It was like, all right, game time, you know?

And I was not the natural 1 on the team to do that.

I mean, like I led every area of the business except for engineering, which I'm now very thankful for.

Went in as interim VPEs, kicked off a search, really got our frontline engineering management together, and then really went in and diagnosed the problems.

We never wrote down our engineering cultural values.

And there was basically like 3 separate camps of teams and how they thought about the standard of engineering at PlanGrid.

Some people would rise to the top and 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 6 months.

We blew up the roadmap, came out with new priorities and people just like, a lot of people hated it.

The right thing we did was we did it all at once.

So it's like, all right, it's gonna be turbulent anyways.

Like, let's just like make all these changes.

And by the way, if there's like any people changes you've been like thinking about, people not working out, you don't really know how to do it.

Like this is the time to do it, just like get rid of them.

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.

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 had to do with even like the engineers, 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.

All right, Tracy, I wanna 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.

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 9 months pregnant and you're water breaking.

Today, Tracy, would you have given that keynote?

Because I shared this photo yesterday and I pulled it up.

I'm 9 months pregnant at my user conference and I'm on stage.

And I go through 14 hours of the conference and I like 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 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 for another 32 hours.

So like, you think about the amount of time I didn't sleep.

So when you reflect on that time, Tracy, what do you think?

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 big enough to a point where you can have a user conference and have a thousand of your customers show up.

And I remember our marketing team being like, yo, and then, you know, they were like, parents are 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.

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, and 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 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 32 hours later, and if I could do it all over again I think for sure I would have recorded my keynote.

I definitely remember arguing with my marketing team and they're just like, stop it.

And I think if I could do it all over, I'd probably show up 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.

Because for me, when I was pregnant, my water broke 8 weeks early and I was hospitalized and we were losing the babies, you know, heartbeat 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.

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, like society's net-net is clearly that women aren't good enough to lead or else you'd 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'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.

And I think that if we were good role models, we would have taken the time to have these life changes and these miracles in our life and let the team take care of everything else.

Because that's actually real good leadership is that you've put the company at a point where you can step out for 3 months and take care of your baby and then come back and the company had progressed and it kept moving on with your vision.

I would have done things way differently.

And I think that part of it is that when you're pregnant, you're not a mom yet, in a way.

You're still that beast of a founder that's going out there and just making progress, used to pushing yourself, right?

It's like, we would have never done that with our second pregnancies.

And you're also pregnant for so long, you know, this 9 month pregnancy.

So like, 7 months go by and maybe pregnancy's not so hard for the ones who are lucky, 7 months go by and then 8 months go by and you're like, okay, I can still do this.

And then you don't think about that last few weeks, which is really hard.

It's ready to come out, pushing up, you know, your cervix ready to pop out.

Like you don't think about that because you've been running for 9 months and it's been fine.

Yeah, there's like an actual full being in you now.

So what would you tell females founders out there who are thinking about starting a family, but they still have that feeling like they have something to prove, to themselves, to others, and they feel that unconscious bias, right?

And so they're under pressure to do these things, these type of things that you and I did, which it sounds like we both regret that we did.

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.

They couldn't have run a construction company or be a leader in a construction firm and be a mom.

And it just makes me so sad because That's exactly the genes we want to keep going on in our gene pool, right?

The first thing is, because this was something I was scared with.

I had basically 3, I'm like 38, I had 3 geriatric pregnancies.

I was like, I remember my doctor was like, I'm sorry, what did you just say?

So that for a long time, I didn't think that I could be a founder and be mom.

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 to not have support that way.

2, what would I tell people who are thinking about it?

Like you wanna work with people who are so excited about you becoming mom, that they're gonna support you and they're gonna have your back when you're on maternity leave, you don't want to work with people who are going to judge you.

More likely than not, it's probably all in our own heads anyways.

If you do have people who are judging, I definitely had an exec who called me 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.

See all Y Combinator transcripts on Youtube

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