June 11, 2025 • 55 mins
Tracy Young, co-founder of PlanGrid, shares how her background in construction led to building one of the most successful startups in the space—culminating in an $875M acquisition by Autodesk. She dives into lessons learned on product-market fit, go-to-market strategy, and navigating founder relationships as the company scaled.
Tracy also reflects on her time at Y Combinator, the fundraising process, and the emotional challenges of selling a company. Post-acquisition, she transitioned into coaching before founding her new startup, TigerEye. She discusses how AI, core values, and leadership growth are shaping this next chapter—and what she wishes more founders knew about resilience and reinvention.
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Episode Transcript
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(00:01):
So
I'm so delighted today to have Tracy Young,who's the cofounder and CEO of PlanGrid before
it was acquired back in 2019, and now the cofounder and CEO of Tiger Eye, which we're going
learn about.
So maybe just to start off, I'd love to hear alittle bit of your background.
(00:23):
Like, where'd you grow up?
What environment was that in?
And just and what was your I know you gotinvolved in construction early on.
What was that job like?
So how far back do we want to go?
Let's go early.
Let's go Okay.
So I'm generation American.
My parents were refugees of the Vietnam War.
Wherever the line was between like homelessnessand just poverty, they were just right above
(00:48):
that line.
So it was very hard for them to be in America,you know, really with nothing.
But they built their way up to the middle classand so as a kid, I watched how hard they
worked.
They worked seven days a week, in some yearsthey were working two jobs.
And I always knew I I needed to make themproud.
(01:11):
I loved drawing.
I loved painting.
I loved building as a kid.
And a big part of me wanted to go to artschool, but I just didn't have it in my heart
to look my immigrant parents in the eyes andit's like, you you guys have been working so
hard and I'm just gonna be a starving artist.
You're worried Because I wasn't that good.
I loved But
(01:31):
you're worried that they were like, okay, thishouse is gonna pay the bills.
Yeah.
Yeah.
Like, sustain a reasonable lifestyle.
And were they in construction or were they in
No.
They were distributors, so they purchased.
Their business was very simple.
It was an honest business.
They would purchase goods in bulk, they wouldmark it up and then they would sell the goods
to restaurants.
(01:52):
And their client base was all of the otherimmigrants in the community.
Was that in the Bay Area?
In the Bay Area.
Okay.
So like you think about pho restaurants andlike taquerias and local Chinese Mhmm.
Food industry.
And what did you study?
Where did you go to university?
I went to Sacramento State.
I studied construction engineering management.
(02:13):
And the career path is you come out of schooland you become a project engineer on
construction projects.
So that's what you did?
That is what I did.
Did that for a few years.
Hard hat, safety vest, safety glasses, closedtoe shoes, muddy boots.
Except that I'm a five foot three Asian womanMhmm.
(02:36):
And so I stuck out like a sore thumb on the jobsite.
But I had a great time.
I I think I was very lucky to work in the BayArea because you imagine that being one of the
few women on a construction site with like athousand men, that that would be hard.
But I I worked with really really greatconstruction leaders who didn't care how I
(02:56):
looked like, they only cared about my output.
And I got to learn from what I still considertoday some of the best leaders.
And I learned a ton from them.
And what and just I'm curious.
Any nuggets from that?
What what were they any any specific learnings
from that?
Be the superintendents on the job sites, andyou have to understand that these
superintendents probably didn't finish highschool, but they went into the trades.
(03:19):
Mhmm.
So they they didn't finish high school, went tobecome a carpenter's apprentice, started making
money, and then these would be the best of thecohorts.
Right?
They would work their way up from foreman tosuperintendent to senior superintendent and
they were like the kings of the job site.
They knew everyone, everyone reported to them.
(03:40):
They could look at a set of blueprints and havein the back of their heads exactly how they
would build an entire hospital.
When the medical equipment would come in, whenthe crane would come in, and they would have a
whole full schedule in their heads.
And they were master builders.
(04:01):
And obviously great leaders, imagine, as well.
And I think just before the exit, PlanGrid waslike 500 Mhmm.
Ish people?
Like, were there any a new scale to become aleader?
Were there any sort of techniques or skillsthat they had that you adopted?
I think what was most impressive about thesuperintendents that I worked for is they were
(04:28):
just at a place where it's very high pressureand high tension because schedule's always
behind, the building owners breathing breathingdown everyone's like things are always messed
up.
You've built something wrong and you've got togo fix it, order new materials, get the crew
back in.
And so it's a pretty high pressure place, butthey were always steady and
(04:48):
calm.
Mhmm.
They also on top of that really cared aboutevery builder there.
Right?
They knew their names.
They knew their children's names and I reallyappreciate that human part of their leadership.
Mhmm.
And I think that's what I really tried toemulate.
(05:09):
That in the day, yes, we're building thisbeautiful building and hopefully every
subcontractor on the job site is making moneywhile we're doing it and we're sending people
home safely to their families every single day,every single night.
But we can also have these relationships on thejob site where we really are friends.
That's great.
Yeah.
(05:29):
I think that was probably my most importantlearning, my time there.
And so you're in this sort of greatenvironment, chaotic, high pressure kind of
construction environment.
And then you got into startups.
Was were you always entrepreneurial?
Or what was the transition from the job siteinto startups?
(05:52):
I was always into projects.
I always had
Building stuff.
Yeah.
Building stuff.
And the idea for PlanGrid came when my reallygood friend who I'd gone to university with,
Brian, he'd all He had been We've known eachother since we were kids.
I mean I was 17 when I met him at theuniversity and he'd always pitched me business
(06:17):
ideas.
Like he was entrepreneurial.
He knew he was going be a business leader.
And, you know, 50 bad business ideas later, hefinally pitched me a good one, which was let's
take all of our construction record set and putit in the iPad.
Let's put it in the cloud, make it available onthe iPad because that is what we would both
like to use as field construction workers,construction engineers, except that it didn't
(06:43):
exist.
So why why not we be the ones to build it?
And this was previously just on paper, thesebig rolls of paper that would be Yes.
Around in the foreman's office and
Yes.
Steve Jobs announced it's the generation iPad.
Ryan had stood in line to buy it for himselfand the thing he did was he tried to load a
(07:04):
blueprint on there.
And then this box comes up and it says out ofmemory.
And he says, we should build this.
And we go through what Ryan calls a saddeststory in Silicon Valley, which is two domain
experts with like a decently good idea and notechnical co founders to build it.
And then we recruited our technical cofounders.
(07:26):
There were initially three of you?
There's five of us actually.
Okay.
So you hired two domain experts and you hiredthree engineers?
Yeah.
Two construction engineers, three
software engineers.
And then you went to you decided to apply forYC?
We did.
My co founder Antoine was reading hacker newsevery day and he really wanted to apply to Y
(07:49):
Combinator.
And he was also he had also he was also asurvivor at that point of cancer, and so we
were ready to do anything with our friend.
You know, like, he wants to apply to YC, we'regonna apply to YC.
And then we got in.
And you were still at your former jobs at thatpoint?
Or you
No, we had left.
(08:10):
We got into Y Combinator, we had all quit ourjobs.
That was the deal.
Antoine, I understand, when he was at thatpoint of
He had a rare form of sarcoma.
Uh-huh.
And he was very young.
He was only 29 when he passed.
And we were in the middle of Wicommere at the
time.
Mhmm.
And, you know, when I think back at that time,we were all just so young.
(08:35):
You know, was like 25, 26.
I'd never seen one of my friends die before.
And so it was incredibly traumatic because wewe were all living out of a hacker house
together in Sunnyvale.
And I think we just didn't know how to dealwith grief.
So we poured everything.
Every calorie we had, we poured it into ourstartup.
(08:59):
Because our friend died, and the next day, wewere back supporting our customers.
Was that in some ways part to to kind of dealwith the grief?
I think so.
And then part in his honor, potentially, interms of just saying, okay, what would he want
us to do?
Yeah.
I think it was it felt like at that point thatif we could make this company successful, that
(09:25):
he is a co founder of this company.
I mean, his code is probably still alive andodd at us somewhere today.
And we really wanted to keep his memory alive.
We also just didn't know how to deal withgrief.
I mean, you know, if if one of your co workers,family member, really good friend died, co
founder died, you'd probably say take some timeoff.
(09:46):
Yeah, yeah.
Just take care of yourself.
And that was exactly the conversation none ofus were having.
We would just work some crazy hours, and we'dsit at dinner, have a glass of wine or whiskey,
and then we would just cry together, and thengo to sleep, and then go back to work the next
day.
And we did this for months.
(10:06):
Were you doing your paying customers at YC?
What was some of the early kind of productmarket fit experience?
Because, you know, while the iPad is sort of afun shiny object, construction industry has not
typically been early adopters of like asoftware.
Mhmm.
What what how did you get initial tractionwithin within the product?
(10:29):
I think in Y Combinator, we got accepted justbased off of a prototype.
And then we went back to all of our collegemates and all of the people we had worked our
butts off on the job site and we said, hey, wetry out our product.
We're building this thing called PlanGrid andwe're gonna digitize a construction record set
for you so you have it at your finger tips.
(10:50):
And we'll solve the version control problem,we'll give you tools to track your your
progress.
And I remember that everyone thought, ofcourse, it was a good idea, except that no one
at this point had iPads.
Apple had limits on how much they couldproduce, and so you could only buy like three
or four at a time.
(11:11):
And so we And I wouldn't recommend startupsdoing this, but this is what we did to remove
our own friction, which is that we maxed out myco founder's credit cards and we procured
something close to like 20 iPads, which was allthe money we all had at that point.
This was very precious to us.
We went back to our friends and we said, whatif we just loaned you an iPad?
(11:34):
Will you use our product and give us feedback?
And that's how we got our 20 users.
When we sold the company, one of thesuperintendents, that's also a good friend of
mine, he had put in by this point, know, aroundthe generation iPad, which is a lot cooler than
the one.
The one's actually quite heavy compared to it.
And he had put that generation iPad on a and ithad like a PlanGrid sticker on it in a shadow
(12:01):
box and and gave that to me as a gift.
Oh, that's great.
Yeah.
What a
great souvenir.
Mhmm.
Was the sales motion within that?
Obviously, you gave 20 to your friends and andconnections.
Yeah.
How did we so they were using it for free.
You know, at some point, they just said thewords like, I love this.
I love PlanGrid.
I'm not sure, like, how we were buildingwithout this thing.
(12:22):
And just the modern design touch interface tokinda to to to be put and not rolling pieces of
paper and kind of looking different
Yeah.
And I mean, now today it's not so impressive.
I mean, every construction tech product hassomething that looks like PlanGrid.
But at the time, we were the thing thatrendered blueprints the fastest and that was
(12:44):
kind of our secret sauce.
And so once we started hearing the words love
Mhmm.
We let them know beta was over and, you know,you can pay for this or we're gonna take
everything back.
We need it back.
And they
said, oh, no, no, no.
Okay, we'll pay.
Yeah.
We told them we could keep the iPads.
In these construction sites, things with subsand GCs, people were interested in this new
(13:08):
shiny object.
And they're interested in how people are doingit.
So was it fairly viral?
Or did you have to kind of do quite a lot ofenterprise sales into this customer segment?
You know, we had something called the iPad minideal, which was you would buy a certain number
of years of PlanGrid upfront.
And then we would throw in an iPad Mini.
(13:30):
And we shipped something like 10,000 iPadsalone for actually the Apple Store in San
Francisco, which was the partner we workedwith.
But was that sort of a top down sales motion orwas that word-of-mouth or partners?
That's a good question.
How did you get the early adoption?
App Store SEO was really important to top offunnel for us.
(13:52):
If we ranked highly on the word construction,something as simple as that.
You can imagine you're working in theconstruction industry, get your mobile device,
and then you search construction because thatis your profession on the App Store and
PlanGrid is the thing that comes up.
That was really, really important to our go tomarket motion.
It was a bottoms up sale.
Someone would download a trial version ofPlanGrid.
(14:15):
They would upload their stuff and then theywould get a phone call that afternoon from
someone at our company saying, hey, who areyou?
What are you up to?
Do you need any help?
Can I help you finish uploading your stuff?
Oh, and by the way, you're on a really bigproject.
Are you sure you don't want me to send asalesperson to your job site for a lunch and
learn?
We'll bring you burritos or bring yousandwiches.
(14:36):
We'll bring you whatever you want.
Just give us thirty minutes of time.
And then that was, you know That was a salesmotion.
So in some ways, being early, having a greatproduct that people loved and then just being
sort of being commercially minded and gettingpeople to sign up helped you get early
adoption.
So you went I think you scaled to like5,000,000 ARR and then raised Series A, is
(14:57):
that?
I guess how did you learn
lot from the job.
PlanGrid was growing the whole time, so everysingle day it was the biggest job I had done
before.
I think it was really important for me to bringon a leadership team.
I probably learned the most from our CFO aboutbusiness and unit economics and why we would
(15:19):
have to think about a business this certainway, right, profitability.
And then just, like, just having really goodmanagers.
And that's probably the biggest learning afterten years in startups is getting to see the
best managers in action and then really tryingto understand what the pattern is is here.
(15:43):
And they just had all been doing it for a longtime.
Mhmm.
So they had the experience of dealing withmanaging people and all of the personalities.
They had just seen some flavor of that if whenyou when you've been doing it for twenty years.
Mhmm.
And then getting to see how they took care ofeach random situation and scenario very
(16:06):
gracefully.
And when did you, you know, when did you startto hire kind of more senior people and then the
CFO?
What stage were you?
Probably our series a because we were prettyflat prior to that.
Everyone reported to the founders.
Then we raised a series A and we needed toscale.
I remember we tripled our team that year.
(16:28):
The investors wanted us to spend money and growfaster.
And then by that point, at a 100 people we justneeded, you know, with a few founders, you just
needed another level of leadership.
And so probably our frontline managers came onat that point.
Some of them didn't work.
We hired the wrong people.
Some of them, you know, ended up takingleadership positions at the company.
Did you hire people with domain experience oryou or miss, try to avoid that?
(16:54):
Domain experience specifically withinconstruction.
Our six salespeople at PlanGrid, we decided totest out the profile.
I was a construction engineer by training, andso I was selling PlanGrid.
I mean, I sold most of PlanGrid up to5,000,000, so I was like, I'll just hire
someone that's like me with my background.
(17:16):
And tested out hiring three constructionengineers and three SaaS salespeople.
Yeah.
And these SaaS salespeople just outperformedthe construction engineers.
The three construction engineers ended uptaking like customer success support roles.
It is very hard for construction engineers tohear no day in and day out.
(17:42):
And that's just part of the job of being insales.
You brush it off and you go into your nextdemo, you get another chance to get a yes.
And that was just something they were notprogrammed to do.
These are people who had always succeeded ontheir building project.
And the sales folks from Salesforce, they werejust so used to getting no's.
Was like, whatever.
(18:02):
I actually sold some deals today, so this is agood day.
Share with me the fundraising timelines.
You raise a series A and then a series B.
And you've very successful raising money.
I guess if you were to look back and I'm sureyou made some mistakes along the way and did
some things right what advice would you givefounders from your own experience in
(18:22):
fundraising?
The advice I give founders on fundraising isyou really have to be in fundraising mode or
not in fundraising mode.
You can't be somewhere in between because itjust doesn't benefit you.
Fundraising, as you know, is a very emotionalprocess.
You are going out to investors and you aretrying to sell a piece of this thing that you
(18:43):
love, that you worked really hard on.
And they might not agree with how much youthink your shares are worth or if your business
is even viable.
And so I think there are some founders thatwill say, like, you want to build relationships
and you want to make sure the partner gets toknow you ahead of when you fundraise so that
(19:05):
the process can go faster.
But I've just found that you you never want tobe the founder on the market trying to sell a
piece of the company for six months.
Mhmm.
Because people are gonna know.
And you don't want like, time kills all deals.
That's probably the takeaway that's mostimportant when it comes to fundraising.
(19:25):
Time kills all deals, and you do not want to bethe founder trying to fundraise for six months
and being unsuccessful at it.
So run an accelerated process.
Keep it tight.
If it works, great.
If it doesn't?
Go back
to work.
Fine.
Get back to work.
Build whatever fee or improve on the feedbackyou've got and get bigger, more interesting
(19:47):
business.
Yeah.
So you raised a series A and then a series B.
Mhmm.
And just what kind of scale people were you at?
And and in terms of just that your evolution asa kind of time founder to being a scale CEO,
what were some of the lessons that you learnedin terms of bringing on executive leadership?
(20:12):
I think the biggest mistakes I've made withexecutive leadership is I knew they weren't the
right fit.
Like, something in my gut told me this is justnot the right fit, but I am so stressed out
right now and I don't want to run marketing orsales anymore and I'm just going to hire this
person because, you know, whatever.
(20:34):
They're going to do at least 75% of the job So,you know, that's that's a whole chunk off my
plate and that's the pressure off me.
And in those instances, it just doesn't reallywork out.
And that there's actually a lot of intelligencein my gut that was telling me this isn't this
isn't this is not quite right.
And then I was like lured by their fancyresumes and backgrounds.
(20:57):
If I could do it all over again in those years,I would have just done a lot more reference
checking.
And of course, you know, you call the threepeople that they give you, it's going to be
positive.
But you ask them, who else should I talk to?
Who else knows this person well?
And you call those people that's two degreesaway.
Then you ask those people, hey, who else shouldI talk to?
(21:17):
And almost always you get three degrees awayand you get much more honest conversations.
And also, you're now piecing together a muchmore full picture of who this person is and how
they are to work with and their contributionsat their last company.
Dimensionalize that.
How many if you if you were to hire a VP or Clevel person
20 people at least.
(21:38):
20 people.
Yeah.
And Because because if you you won't know for afull year if they are good or not.
You're gonna at least give them that.
And then if they're not working out in thatyear, you've just wasted time and their blast
radius is kind of big because if they're at theVP exec level, you've probably given them
budget to hire a team.
(21:58):
And so now there's other people you've got tofigure out if they're good or not and manage
them out or promote them or, you know, hopethey stay.
Yeah.
Know from experience, it's really hard.
If you make a bad decision, then it's
very the right executive and then seeing awhole department just take care of themselves
and get things done and you don't have to worryabout it again.
(22:20):
You also know how that feels and it just feelsreally good.
And was that as you as you got to kind of northof 100 and a 150 people, was that Where did you
spend your time?
I imagine you had people focus on sales andmarketing and product and HR.
What were the areas of focus that you spent ontime?
(22:42):
It really depended on where we were hurting themost.
I personally like spending my time testing outthe product and then on sales calls, talking to
users, and then figuring out how to prioritizeour product roadmap for this quarter.
That's how I like to spend my time.
But there were years where, you know, there wasno engineering leader and I had to step in as
(23:05):
interim VPE as we were doing that search for afull year.
Same thing with marketing, you know?
So it just really depends on where there's alack of leadership and where we need to airdrop
in the founders.
The outside in view of startups is that it'slike you found it, you go through or get early
funding, and then it's seven years later, it'skind of you go public or you're quiet.
(23:30):
Imagine along the way, there were someexistential moments, some moments where really
felt that this is okay.
If we don't figure this out, we're gonna gobankrupt or have to shut down.
Yeah.
And the worst moments?
The worst moments are always thinking aboutpayroll and not being able to make it.
That always feels super bad.
(23:52):
The other worst moments are just you know,there's like infighting at the company or
you're not getting along with one of the execs.
And the nice thing about being founder CEO isyou get to fix all this, especially at the
executive level.
And the signs of an exec not working out, Ithink, is when you or anyone that reports to
(24:13):
you not working out is when you start dreadinghaving one on ones with them.
That is the biggest red flag.
Because with your team, you should feel soexcited to finally get thirty minutes or an
hour to figure out what they've been up to,where the challenges are, and then also you
might need things from them and, you know, it'sa it's a partnership.
(24:33):
When you're dreading having one on ones with anexecutive, like, that is so so bad because
that's how messed up things are.
That's how messed up the relationship is.
Probably because something's not working.
And how did you obviously, perhaps inretrospect you sort of realized that those one
on one you avoided those one on ones.
(24:54):
Was that specifically a situation where youended up terminating the executive?
Or they self selected out.
They just left.
And is that just as you think about learningexperience when things are not working, is
there anything you would do differently afounder or executive?
You can never fire fast enough.
(25:15):
And the reason for this is because at thefounder CEO level, when someone isn't working
out, the people to know are the people thatreport to them.
And then it's their peers, and then it's you.
So the whole company's known that this personisn't working out.
(25:35):
You just haven't made the decision yet becauseit took a while for you to figure it out.
So by that point, it's like it's very clearwithin the organization that it's not going to
work.
And so it's just the organization just requiresyou to make the decision.
But it takes courage and sometimes, you know,it just isn't there with everything going on.
So PlanGrid scaled from zero to close to100,000,000?
(26:00):
The day we hit a 100,000,000 in ARR.
I don't know why this was so important to me.
It's a nice number.
It was the day I stepped down as CEO and passedthe baton over to the team.
And I knew we knew when it was gonna happen.
We're pretty good at forecasting.
And that gave me six months to integrate.
(26:21):
Because once we hit that mark, we really pushedfor integration into the mothership, into
Auditars, our acquirers.
So we're still we were still like a standalonestartup.
Okay.
But by that point, you're sufficient scale.
Let's leverage the mothership.
But going back a little bit, how did that whatwas the thought process around M and A?
You know, imagine you could have beenprofitable if you wanted to be profitable at
(26:45):
that point.
You had scale.
You could have raised more money.
What was the decision process around combiningforces with Autodesk?
It was a hard decision.
So I think our jobs as founders and leaders ofa company is to maximize all options available
(27:08):
to us.
While we were having conversations withAutodesk, I was also fundraising a Series C.
And part of it was just to have leverage andoptions, right, as we were negotiating.
But when we so we had a Series C term sheet,maybe two, and we had a term sheet from
(27:28):
Autodesk.
And they had given us a multiple, it was like10 something x our current revenue, our next
twelve months revenue.
This is Autodesk.
This is Autodesk.
And so it was a good offer.
And I really went and did the math.
(27:48):
You know, with the Series C, we are all goingto take a round of dilution, and then maybe a
Series D and then maybe we can take the companypublic at that point at like 200,000,000 in
ARR.
And when we did the math, it was like, wow,Autodesk's offering, like, we would have to
execute perfectly and flawlessly for the nextthree years for us to have really the same
(28:13):
financial outcome.
When we looked at the team and what, you know,you start doing the math, it's like, oh, well,
for these, like, 50 people, it's like, it'smeaningful.
Like, they can take care of people in theirlives.
And that really helped out on the decision.
Right?
Like, seeing where we were in the market andknowing that there were serious obstacles ahead
(28:38):
of us, that there was a company called Procore.
They were three times larger than us.
They were number one.
We were considered number two.
Mhmm.
And we were still growing 75% year over year,which is like not too shabby.
Yeah.
Yeah.
But I didn't know how to accelerate growth.
We really looked at every which way and wedidn't know how to do it.
(28:59):
And so there was risk to us being able toexecute flawlessly over the next three years.
And here, Autodesk was going to de risk it allfor us.
And that's a very analytical approach.
I imagine, know, this is in some ways up untilthis point, this is your life's work, and
you're building this.
So I guess, you know, how emotionally, thatmust be very hard to kind of you know, Autodesk
(29:26):
is a big corporate.
You're the pirate, the small startup.
Like, was was this something that you you'revery rational the way you describe it, but were
you under a lot of pressure from investors togo down this route or employees?
Or was something else personally was drivingthat path?
(29:48):
I think at that point, I didn't see how we weregonna be able to compete with Procore.
And I could see a world where we combined withnumber three, which was PIM three sixty, a
product owned by Autodesk.
And by the way, Autodesk was like the front endof everything we were doing.
Were the leaders in design and we were justsomehow it was somehow getting exported into
PDF and we were ingesting those PDFs.
(30:09):
So there was a very obvious product synergyhere where you just direct forget about
printing into PDF, you just direct send it overto PlanGrid, and then there goes the field
workers.
They can use PlanGrid to build.
So the product synergies was there too.
And I think the board was happy about becausewe had only raised a series b up until that
(30:30):
point.
They were happy with being acquired.
And they I remember they really wanted us toshop the deal.
Actually, all coming back to me now.
They really wanted me to go to SAP and Oracleand then try to get a higher valuation, or just
a bigger term sheet.
(30:51):
And I was really against it.
It's like, what the heck is SAP or Oracle goingto do with us?
Like, they have no interest in construction.
And they're like, it can be just twenty fourhours.
We have, like, the right phone calls, and we'llmake a phone call and just give the
presentation, and, you can just go and pitchthem.
It's like, it was so remember it being soemotional.
It was like, you don't understand.
Like, I can't do that.
(31:12):
I'm just not going to do that.
And Autodesk is the only company that actuallymakes sense for us to be acquired by.
And BIM three sixty was a separate startup?
It was another startup acquired by Autodesk.
Okay.
So you could?
We would combine it.
And that is the product today.
It's a BIM three sixty PlanGrid product renamedas I don't know what Autodesk Build.
(31:35):
Okay.
And when did Autodesk acquired BIM three sixty?
Gosh.
I want to say ten years prior to ouracquisition.
Okay.
I mean, they were working on tablet PCs, so itmust have been really old.
I know from my own experience, go, you know,truly emerging.
But Zillow was actually we were number two.
Zillow was number one.
And we spent a lot of time like okay, we wereboth public companies and so we had some
(31:57):
pressure on expenses, but the same questionlike, how do you become number one if you're
number two?
And the premium there's a real premium to benumber one.
And whether you're in marketplaces with strongnetwork effects or whether you're kind of
enterprise SaaS where you're you become thesort of, you know, the default choice, that
sort of customer choice, it's We face this verysimilar question, like how do you get to number
(32:22):
one?
And I think that and that kind of spurred alittle bit of the decision to to combine forces
with Zillow.
You start to go on this on this journey andyou're both growing, and then at some point
it's like to get into the sort of higher airrequires a different strategy, a different
approach, or enormous capital or somethingdifferent, perhaps similar dynamic.
There was a range of M and A going on in thecategory.
(32:46):
So Rupert Murdoch, within residential realestate, Rupert Murdoch were declared a decision
to buy one of the companies.
And I think everyone was teaming up for a dancepartner.
So there was like Trulia and zillowrealtor.com,which Rupert ended up buying in the end.
But you could see that there was this sort ofdislocation happening in the industry because
(33:12):
everyone was figuring out that this is a hugeprize.
And if people were not going to if you stayedalone and independent, you would struggle.
And you probably sensed that as a founder, thatyou'd like, Okay, this is status quo is
probably not an option.
(33:32):
Because you see these big forces movingquickly.
Yeah, you see the trends.
You see which segments of your business isgrowing and not growing.
And everything you're trying is just notaccelerating the growth that you want to see.
Yeah.
And I remember talking to the board, it's like,I don't know how to do this.
Can we hire a CEO?
I remember Doug Leone with Sequoia was like,CEOs are only for like founders who are shitty
(33:57):
and you're not a shitty founder.
And then I was like, okay.
Well, how about we start talking aboutsuccession, we start talking about doing a CEO
search?
Because I don't know how to get us from a 100to 500.
And
they were really against it.
Good for them.
(34:18):
Yeah.
They just didn't believe that that would makethe company successful.
So you So I was I was really out of choiceshere.
Right?
Yeah.
Yeah.
Because I think PlanGrid could have kept goinghad we had just a CEO who knew what they were
doing.
And, know, that's not to, like, talk myselfdown because I obviously, you know, not bad for
(34:40):
not having any CEO experience at the time, hadtaken the company that far.
But it was very obvious to me there needed tobe some big step changes.
I don't even I couldn't even fathom what theywould be Mhmm.
To accelerate growth and to cut costs at thecompany.
What did you and that's a very you know, tosort of think that you are not the right person
(35:03):
to necessarily scale it to become a 500,000,000revenue?
Like, what like, that's most most founders havethis unwavering belief that they can do
anything.
What how did that realization come to you?
I feel like I was just keeping it real, Pete.
(35:25):
Mhmm.
I
was just being honest with myself.
I didn't know how to do it.
I could see us steadily growing.
Right?
But you see you see us going from, like, 85%year over year growth to 75% year over year
growth, which is when we sold the companybecause our talks with Autodesk was almost a
year.
(35:47):
But to to turn that into 300 or 400% growth, Ididn't know how to do it.
And do you think the market couldn't absorb?
Because sometimes the best executives justcannot change their dynamics.
Do you think there's a belief do you think youcan do it?
(36:08):
Or do you think PlanGrid couldn't do it?
I think that it would have required a brand newexecutive team.
New product leader, new engineering leader, newsales leader, new marketing leader, new CEO,
and I thought that it would be possible in thatcase.
Because that there would be enough turbulencethere where you can really make some serious
(36:30):
changes and it would be okay.
The other option would be to join forces withAuditUS.
Mhmm.
And to compete that way.
And those are really at that point the only twooptions I saw.
I mean, of course, we could have raised aseries c and signed that term sheet.
Again, it kept on going.
But I didn't like a world where we were numbertwo and number one was four times or five times
(36:57):
bigger than us.
Yeah.
And if things started to if things continue theway that they were, then your attractiveness as
a company may go down.
Or Autodesk would make another acquisition,another space.
Did you share just your concerns about yourability to kind of reaccelerate growth with the
(37:19):
board?
Yeah.
I told them I thought we should hire, we shouldthink about hiring another CEO.
I don't know how to do it.
Was a very simple conversation.
So when the Autodesk deal came about, it wasimagine from their perspective, they're like,
Okay, the risk of changing leadership
(37:40):
Yes.
That's exactly what happened.
Is just like a level of risk that we're justnot able to because there is a ton of risk with
that Mhmm.
Versus taking the offer that's on
the table.
Right.
Right.
And I wasn't going to quit on the spot.
Was like something I wanted to plan with theboard over two years.
But the Autodesk deal happened during thattime.
And or at least Autodesk calling me happenedduring that time.
(38:04):
And so, you know, the board's immediatereaction was like, let's just put that on hold.
Let's see where this goes.
And the and how long was the dating processwith Autodesk?
It was almost a year.
We're talking about like 11 I think they justcouldn't make up their mind of who they were
going to buy if they could buy Procore orPlanGrid.
That was really why it took so long.
(38:26):
As you look back on the experience, I'm surefounders approach you for advice about how to
navigate M and A.
Is that like, in retrospect, what are thethings that you would do differently?
And perhaps in also in retrospect, like, arethe things you said, okay, that was a smart
move?
So probably wouldn't do anything differentlyjust because it was a good outcome for us.
(38:50):
And Autodesk took care of our team.
You know, I'm very happy and grateful for theoutcome.
A lot of my old teammates are leaders atAutodesk today in the construction division.
In terms of what I tell founders when they getapproached by an Autodesk or some other
potential acquirer is I tell them that it isvery, very far away from a real deal to not get
(39:18):
too excited, but their again, their jobs is tomaximize options.
And so it's really important to know who's onthe other side.
Like, if unless there's a c suite on the otherside, it's probably not a real deal.
If there's corp dev only on the other side,they're just kicking the tires.
And then I'll also remind them that theirnumber one priority is to keep all of these
(39:46):
conversations confidential because it's toodistracting for the team.
And this is what we did right.
Thanks to our CFO who had been a part ofseveral m and a deals is the only people who
knew was my co founder and our CFO during thatyear long conversation.
And was it like dinners with the CEO atWaterdesk and a lot of like
(40:07):
We had a code name for the talks.
You remember this?
What was the code name?
Do you remember?
It was some wine.
And there, I don't know, someone was into wineand
drinks, so I don't remember.
Yeah.
Okay.
And so the transaction closed, and you were a100,000,000 revenue.
What was the I listened to a few of yourpodcasts.
(40:28):
So it sounded like there was a culture clash.
You were the startup.
They were the big corporate.
How did that make you feel?
I'd never worked for a public company up untilthis point.
And it really did feel like I wasn't allowed tosneeze without checking with five heads of
divisions.
(40:48):
And then it was really hard to find time ontheir calendars.
And then we would meet for an hour.
You can imagine this is a very expensivemeeting.
And then it was like, okay, we'll scheduleanother meeting to talk more.
And that would be three months later.
And what felt like should have been just athirty minute conversation and a decision after
that.
So it was really hard for me to work at thatvelocity.
(41:14):
In hindsight, it makes sense because they havethey have to take the earnings calls every
three months and they can't make they have toreally think through each decision because
Mhmm.
Any major decision is going to probably affecttheir stock price.
And they have a fiduciary duty to all of theirshareholders to not mess up the stock price.
(41:36):
Right?
Yeah.
And that was just a perspective I did not have.
And from my perspective, it's like, why can'tyou guys make the obvious decisions?
Why do we have to keep talking about this veryobvious thing we should do?
What's wrong with you guys?
Right?
But I'm really grateful for my time therebecause I got to see how a public company
(41:57):
works.
A 50 year old company and they're, you know,they were doing a lot of good things and then
there's also a lot of room for improvement.
And so you stayed about a year?
One year.
And then you then you moved on and
I think I worked for Y Combinator after that.
Okay.
So that was a transition for you.
(42:18):
So you left and then spent some time at YC?
Investing, coaching.
I really liked the coaching part.
The investing part was much harder
for me.
Why was that?
I just never knew if I was doing a good job.
That was the hard part.
Yeah.
The feedback cycles in this industry are solong that it's so hard to know.
(42:40):
And now you're running a new startup?
Tiger Eye.
Tiger Eye.
What was, you know, ten year journey, a greatoutcome, what was and you were kind of in YC.
What was the kind of restart moment for youlike to start another company?
What was the sort of catalyst for that?
(43:02):
So we're a husband and wife team.
Ralph is also the co founder of PlanGrid.
You know, we just kept talking about thingsthat would be great for businesses.
Like, oh, this would be a really good product.
This would be cool.
This technology allows for this to happen.
What about this?
And we we just had a lot of conversationsthere.
And I think it came to a point where we were atthe decision point of whether we were gonna
(43:25):
found a new startup or not.
And for us, we really didn't want to regret notdoing it.
I didn't want to be in my seventies oreighties, hopefully even get to live that long,
and then just regret, like, oh, I wish Istarted another company to see what would
happen.
And so we just did it.
Was some of the idea just the observationwithin Autodesk and seeing, okay, this is, you
(43:51):
know, this big company should be run a lot moreefficiently.
We had a really unique perspective, which wasAutodesk had acquired, I think, three other
small startups at the time.
And so we were all coming together to formtheir new construction division.
And you can imagine three startups selling intothe construction industries, and I was in
(44:13):
charge of integrating the back office systemsas well as people.
But back office systems was really gnarly, andI remember that being really painful and knee
deep in it.
And we had all spent millions of dollars ofsetting up our Salesforce environments, and now
we were trying to merge them into one.
And I remember thinking, wow, this is look howwasteful this is.
(44:34):
Like, we had all bought the same lead list.
We had all jammed it into Salesforce, force.
And now we just like need one environment.
And so that was one problem.
Same thing existed on the ERP side.
Wow.
Look at all our reporting.
We're all trying to calculate ARR and churn andgross margin and EBITDA.
And it's like the same financial metrics thatare important to any business.
(44:58):
And it's like, now we've got to consolidatethis and reconcile it.
And it just seemed highly ineffective andwasteful and so many conversations with
everyone's data teams.
And so we wanted to build the thing out of thebox.
And as you were starting this company, Iimagine there are probably some reflections.
Okay.
These are things we did right at PlanGrid, andthen if we start a new company, we're gonna
(45:22):
definitely do it a different way.
What were the things or elements you broughtwith you to the new company?
And then what are the things like, Okay, wemessed up here.
Let's do something different.
Yeah.
We came up with a business idea.
And actually, we decided to start a startupduring 2020, which gave us a lot of time during
shelter in place to just sort of talk throughwhat we would do differently.
(45:43):
The thing we did was we whiteboarded all thenames that we wanted to work with again.
All the people that we thought were excellentand talented and hardworking and just amazing
individuals.
We put their names down.
We then wrote down and this wasn't that many,it was a much smaller population just like a
handful of names of just people we would neverwork with again.
(46:04):
And what you see is a very black and whiteworld of core values.
Like, this is why this is what makes thesepeople amazing.
They are humble.
We trust them.
They're hardworking.
You know, they're good teammates.
And you really get to have a really clearpicture of the people that you want to work
(46:25):
with again and the people that you do not.
And that was how we formed our core values.
I mean, I think we had them written down in,like, within an hour.
So it was less about the higher list, it wasmore about what is it about these people that
makes them special employers and special teammembers?
Mhmm.
And then codifying that into a set of values.
(46:45):
Set of values.
We also added in something I callwholeheartedness, which is that this time
around as parents and being startup founders,knowing how all consuming it can be, that we
also want to be good parents while we're doingthis.
And so the only way we're gonna be able to dothis is, one, of course, we have a highly
(47:05):
regimented schedule.
There's highly protected kids time and thenhighly protected work time.
Mhmm.
And we promised ourselves that we would befully in as parents and fully in as founders.
Mhmm.
And that's the concept of being wholehearted.
That your your whole heart is there.
You're not splitting it up into multipledirections trying to balance life.
(47:28):
Right?
Someone else is responsible for my kids.
I'm not thinking about them.
I'm only thinking about tiger eye during thesehours.
Mhmm.
I heard something in my research around likeyou you had like some blank grid, you had a no
jerks policy that you Oh
yeah, it was actually no assholes.
No assholes.
At some point, we had HR come in and they'relike, you can't use that word.
(47:50):
I was like, oh, I can't use that word.
Okay, no jerks.
Okay.
Whatever.
But you felt that it wasn't necessarily appliedthroughout the organization.
Yeah.
The problem with not following even one of yourcore values is the signal to the rest of the
(48:12):
team, is the other four core values is completehorseshit.
So we had this core value called neuro jerks,except you looked at the building and it was
like, wow, there's probably like three of themin the building.
And Tracy kept them there.
And so what that also signaled to the team isyou just have to perform for Tracy and you can
(48:32):
get away with murder.
And, you know, I should have just either had areally strong talk with them or just fired
them.
We did this thing at True Lessons.
Similar thing, you know, like, you start acompany, you figure out as a founder the
environment you want to work in, and then youwrite down your half a dozen values and you
(48:53):
stick them on the wall.
And some companies just forget about them andsay, these are values here.
We check.
We've done their values.
We ended up doing a company survey everyquarter.
We'd ask the whole team, like, on a scale ofone to five, how are we actually living these
values or not?
(49:15):
Exactly as you say, because there were a bunchof one of them was customer obsessed.
And there was a period of time in 2008 where wewere running out of cash.
It was like customer obsession just came downbecause we just need to pay the bills.
We weren't really improving the product.
We were just trying to sell as much as wecould.
(49:37):
But it really kept us honest about how we were.
And we shared all the results with the wholecompany.
You're running a company, you sort of the sameway you track NPS, the same way you track
funnel conversion rate, you're the sameretention, you would track these numbers
longitudinally.
It was fascinating to see that.
(49:59):
And so I'm sure that's you'll either do thatsort of implicitly from the way that you run
the company or maybe track it through some sortof survey across the organization.
There's a ton of tools out there that do thatsort of thing now.
We are so serious about our core values thetime around.
I actually have another document called OurCommitments to Each Other and people sign it
(50:21):
when they join.
Okay.
And it is written in a way where there is noambiguity on how you are to work here.
So it says things like, will walk it like Italk it.
Mhmm.
If I have a problem with a teammate, I willnever speak destructively behind their back.
And if I find one of my teammates speakingdestructively behind someone else's back, I'm
(50:42):
gonna correct them on the spot and have thembring it up with my coworker and just deal with
it.
Because we are all adults.
Mean, it's written in a much better way, butI'm giving you the summary here.
And the and the mere fact of them signing it isjust their testament to like, okay, we can live
by these values?
And they've read them and Yes.
We've had our employees bring up, like, thisperson is not living up to the values and we
(51:08):
need to get rid of them.
We by
the core values.
And what's next for TigerEye then?
I'm really interested in other industries, liketraditional industries who have historically
had very low tech adoption.
I'm very excited to talk to them because thereality is AI is like the poor man's
technology.
(51:28):
It's very fast and cheap to stand up and youcan see return on investments almost
instantaneously.
And you started Tigra in 2020, at leastconceptually, like at which point, AI, you
probably were aware of AI, but it wasn't asmainstream or as powerful as it is today.
How has your view on the opportunities with AIchanged over the last four, five years?
(51:56):
Our team's always been machine learningexperts.
You know, we've been doing old school AI.
It was November 2022 was when conversational AIwas introduced to the world.
And so there was always a lot of AI built intothe core technology.
We use simulation theory to predict the future.
(52:18):
I mean, we get a lot of prediction questions aswell.
And I think conversational AI really just helpus think differently about the user interface
of TigerEye.
The core is still there.
It's just it's very easy, right?
You now have this conversational chat box to doeverything.
(52:39):
So that part changed
Mhmm.
But in a much better way because it obviouslyis the future.
And then just going back a little bit about isyour evolution as a founder and a leader?
Like, what just is you achieving the success?
Like, what are the things that you perhapswould do differently or the things that you
(53:02):
say, well, that really helped me through thischallenging period as founder and CEO?
I remember when I was younger, the revenuemilestones were really important to me.
I mean, of course, are like hitting our targetsare important, of course.
But I was never happy.
Like, I remember telling myself, like, if wejust get to I'm so stressed out right now.
(53:24):
If I could just get to 10,000,000 in ARR andthen you get there.
And it's like, if we could just get to, like,30,000,000 in ARR, if we could just get to 50,
get to a 100, like, every time we got there, itwas just kind of it's just me, like, you know
Just a number.
It's just a number.
Exactly.
And when I think back and reflect back at myjourney as a founder, the best memories are
(53:47):
always with people.
I was building cool stuff with people.
Those are undeniably the best memories and theones I will take to my grave.
And so that's really what's different aboutTracy today than Tracy fifteen years ago.
The shared moments, the collaboration.
(54:09):
It's really important that we enjoy the ridewith the people we're building with and the
people we're building for.
And just the definition of success for you,what is that?
If you would think, okay, obviously, there'sthe financial success of Tiger Eye or startups
in general, but what does success mean to younow?
(54:30):
Yeah.
So the revenue targets are still there, hittingthem.
Success has to include the financial part.
But now, I think it also includes the humanpart that we created good jobs that people were
proud of.
I mean, I just talked to you about a teammatethat is that tiger that used to work for you
and he's very proud of what he did with thewhole team at Trulia, right?
(54:54):
Like to me, that is what success looks like.
Yeah.
You kind of have that fond experience.
Yeah, we did.
Yeah, sure.
We delighted customers.
We paid good salaries.
Stock options did well.
But then it's like the memories.
A decade later, more than a decade later, thatis what people remember.
That was a happy place.
Well, that, Tracy, thank you so much forjoining us today.
(55:17):
Amazing journey, amazing opportunities, amazingfuture ahead for TigerEye.
So thanks for joining us.
Thanks for having me, Pete.
So
I'm so delighted today to have Tracy Young,who's the cofounder and CEO of PlanGrid before
it was acquired back in 2019, and now the cofounder and CEO of Tiger Eye, which we're going
learn about.
So maybe just to start off, I'd love to hear alittle bit of your background.
(00:23):
Like, where'd you grow up?
What environment was that in?
And just and what was your I know you gotinvolved in construction early on.
What was that job like?
So how far back do we want to go?
Let's go early.
Let's go Okay.
So I'm generation American.
My parents were refugees of the Vietnam War.
Wherever the line was between like homelessnessand just poverty, they were just right above
(00:48):
that line.
So it was very hard for them to be in America,you know, really with nothing.
But they built their way up to the middle classand so as a kid, I watched how hard they
worked.
They worked seven days a week, in some yearsthey were working two jobs.
And I always knew I I needed to make themproud.
(01:11):
I loved drawing.
I loved painting.
I loved building as a kid.
And a big part of me wanted to go to artschool, but I just didn't have it in my heart
to look my immigrant parents in the eyes andit's like, you you guys have been working so
hard and I'm just gonna be a starving artist.
You're worried Because I wasn't that good.
I loved But
(01:31):
you're worried that they were like, okay, thishouse is gonna pay the bills.
Yeah.
Yeah.
Like, sustain a reasonable lifestyle.
And were they in construction or were they in
No.
They were distributors, so they purchased.
Their business was very simple.
It was an honest business.
They would purchase goods in bulk, they wouldmark it up and then they would sell the goods
to restaurants.
(01:52):
And their client base was all of the otherimmigrants in the community.
Was that in the Bay Area?
In the Bay Area.
Okay.
So like you think about pho restaurants andlike taquerias and local Chinese Mhmm.
Food industry.
And what did you study?
Where did you go to university?
I went to Sacramento State.
I studied construction engineering management.
(02:13):
And the career path is you come out of schooland you become a project engineer on
construction projects.
So that's what you did?
That is what I did.
Did that for a few years.
Hard hat, safety vest, safety glasses, closedtoe shoes, muddy boots.
Except that I'm a five foot three Asian womanMhmm.
(02:36):
And so I stuck out like a sore thumb on the jobsite.
But I had a great time.
I I think I was very lucky to work in the BayArea because you imagine that being one of the
few women on a construction site with like athousand men, that that would be hard.
But I I worked with really really greatconstruction leaders who didn't care how I
(02:56):
looked like, they only cared about my output.
And I got to learn from what I still considertoday some of the best leaders.
And I learned a ton from them.
And what and just I'm curious.
Any nuggets from that?
What what were they any any specific learnings
from that?
Be the superintendents on the job sites, andyou have to understand that these
superintendents probably didn't finish highschool, but they went into the trades.
(03:19):
Mhmm.
So they they didn't finish high school, went tobecome a carpenter's apprentice, started making
money, and then these would be the best of thecohorts.
Right?
They would work their way up from foreman tosuperintendent to senior superintendent and
they were like the kings of the job site.
They knew everyone, everyone reported to them.
(03:40):
They could look at a set of blueprints and havein the back of their heads exactly how they
would build an entire hospital.
When the medical equipment would come in, whenthe crane would come in, and they would have a
whole full schedule in their heads.
And they were master builders.
(04:01):
And obviously great leaders, imagine, as well.
And I think just before the exit, PlanGrid waslike 500 Mhmm.
Ish people?
Like, were there any a new scale to become aleader?
Were there any sort of techniques or skillsthat they had that you adopted?
I think what was most impressive about thesuperintendents that I worked for is they were
(04:28):
just at a place where it's very high pressureand high tension because schedule's always
behind, the building owners breathing breathingdown everyone's like things are always messed
up.
You've built something wrong and you've got togo fix it, order new materials, get the crew
back in.
And so it's a pretty high pressure place, butthey were always steady and
(04:48):
calm.
Mhmm.
They also on top of that really cared aboutevery builder there.
Right?
They knew their names.
They knew their children's names and I reallyappreciate that human part of their leadership.
Mhmm.
And I think that's what I really tried toemulate.
(05:09):
That in the day, yes, we're building thisbeautiful building and hopefully every
subcontractor on the job site is making moneywhile we're doing it and we're sending people
home safely to their families every single day,every single night.
But we can also have these relationships on thejob site where we really are friends.
That's great.
Yeah.
(05:29):
I think that was probably my most importantlearning, my time there.
And so you're in this sort of greatenvironment, chaotic, high pressure kind of
construction environment.
And then you got into startups.
Was were you always entrepreneurial?
Or what was the transition from the job siteinto startups?
(05:52):
I was always into projects.
I always had
Building stuff.
Yeah.
Building stuff.
And the idea for PlanGrid came when my reallygood friend who I'd gone to university with,
Brian, he'd all He had been We've known eachother since we were kids.
I mean I was 17 when I met him at theuniversity and he'd always pitched me business
(06:17):
ideas.
Like he was entrepreneurial.
He knew he was going be a business leader.
And, you know, 50 bad business ideas later, hefinally pitched me a good one, which was let's
take all of our construction record set and putit in the iPad.
Let's put it in the cloud, make it available onthe iPad because that is what we would both
like to use as field construction workers,construction engineers, except that it didn't
(06:43):
exist.
So why why not we be the ones to build it?
And this was previously just on paper, thesebig rolls of paper that would be Yes.
Around in the foreman's office and
Yes.
Steve Jobs announced it's the generation iPad.
Ryan had stood in line to buy it for himselfand the thing he did was he tried to load a
(07:04):
blueprint on there.
And then this box comes up and it says out ofmemory.
And he says, we should build this.
And we go through what Ryan calls a saddeststory in Silicon Valley, which is two domain
experts with like a decently good idea and notechnical co founders to build it.
And then we recruited our technical cofounders.
(07:26):
There were initially three of you?
There's five of us actually.
Okay.
So you hired two domain experts and you hiredthree engineers?
Yeah.
Two construction engineers, three
software engineers.
And then you went to you decided to apply forYC?
We did.
My co founder Antoine was reading hacker newsevery day and he really wanted to apply to Y
(07:49):
Combinator.
And he was also he had also he was also asurvivor at that point of cancer, and so we
were ready to do anything with our friend.
You know, like, he wants to apply to YC, we'regonna apply to YC.
And then we got in.
And you were still at your former jobs at thatpoint?
Or you
No, we had left.
(08:10):
We got into Y Combinator, we had all quit ourjobs.
That was the deal.
Antoine, I understand, when he was at thatpoint of
He had a rare form of sarcoma.
Uh-huh.
And he was very young.
He was only 29 when he passed.
And we were in the middle of Wicommere at the
time.
Mhmm.
And, you know, when I think back at that time,we were all just so young.
(08:35):
You know, was like 25, 26.
I'd never seen one of my friends die before.
And so it was incredibly traumatic because wewe were all living out of a hacker house
together in Sunnyvale.
And I think we just didn't know how to dealwith grief.
So we poured everything.
Every calorie we had, we poured it into ourstartup.
(08:59):
Because our friend died, and the next day, wewere back supporting our customers.
Was that in some ways part to to kind of dealwith the grief?
I think so.
And then part in his honor, potentially, interms of just saying, okay, what would he want
us to do?
Yeah.
I think it was it felt like at that point thatif we could make this company successful, that
(09:25):
he is a co founder of this company.
I mean, his code is probably still alive andodd at us somewhere today.
And we really wanted to keep his memory alive.
We also just didn't know how to deal withgrief.
I mean, you know, if if one of your co workers,family member, really good friend died, co
founder died, you'd probably say take some timeoff.
(09:46):
Yeah, yeah.
Just take care of yourself.
And that was exactly the conversation none ofus were having.
We would just work some crazy hours, and we'dsit at dinner, have a glass of wine or whiskey,
and then we would just cry together, and thengo to sleep, and then go back to work the next
day.
And we did this for months.
(10:06):
Were you doing your paying customers at YC?
What was some of the early kind of productmarket fit experience?
Because, you know, while the iPad is sort of afun shiny object, construction industry has not
typically been early adopters of like asoftware.
Mhmm.
What what how did you get initial tractionwithin within the product?
(10:29):
I think in Y Combinator, we got accepted justbased off of a prototype.
And then we went back to all of our collegemates and all of the people we had worked our
butts off on the job site and we said, hey, wetry out our product.
We're building this thing called PlanGrid andwe're gonna digitize a construction record set
for you so you have it at your finger tips.
(10:50):
And we'll solve the version control problem,we'll give you tools to track your your
progress.
And I remember that everyone thought, ofcourse, it was a good idea, except that no one
at this point had iPads.
Apple had limits on how much they couldproduce, and so you could only buy like three
or four at a time.
(11:11):
And so we And I wouldn't recommend startupsdoing this, but this is what we did to remove
our own friction, which is that we maxed out myco founder's credit cards and we procured
something close to like 20 iPads, which was allthe money we all had at that point.
This was very precious to us.
We went back to our friends and we said, whatif we just loaned you an iPad?
(11:34):
Will you use our product and give us feedback?
And that's how we got our 20 users.
When we sold the company, one of thesuperintendents, that's also a good friend of
mine, he had put in by this point, know, aroundthe generation iPad, which is a lot cooler than
the one.
The one's actually quite heavy compared to it.
And he had put that generation iPad on a and ithad like a PlanGrid sticker on it in a shadow
(12:01):
box and and gave that to me as a gift.
Oh, that's great.
Yeah.
What a
great souvenir.
Mhmm.
Was the sales motion within that?
Obviously, you gave 20 to your friends and andconnections.
Yeah.
How did we so they were using it for free.
You know, at some point, they just said thewords like, I love this.
I love PlanGrid.
I'm not sure, like, how we were buildingwithout this thing.
(12:22):
And just the modern design touch interface tokinda to to to be put and not rolling pieces of
paper and kind of looking different
Yeah.
And I mean, now today it's not so impressive.
I mean, every construction tech product hassomething that looks like PlanGrid.
But at the time, we were the thing thatrendered blueprints the fastest and that was
(12:44):
kind of our secret sauce.
And so once we started hearing the words love
Mhmm.
We let them know beta was over and, you know,you can pay for this or we're gonna take
everything back.
We need it back.
And they
said, oh, no, no, no.
Okay, we'll pay.
Yeah.
We told them we could keep the iPads.
In these construction sites, things with subsand GCs, people were interested in this new
(13:08):
shiny object.
And they're interested in how people are doingit.
So was it fairly viral?
Or did you have to kind of do quite a lot ofenterprise sales into this customer segment?
You know, we had something called the iPad minideal, which was you would buy a certain number
of years of PlanGrid upfront.
And then we would throw in an iPad Mini.
(13:30):
And we shipped something like 10,000 iPadsalone for actually the Apple Store in San
Francisco, which was the partner we workedwith.
But was that sort of a top down sales motion orwas that word-of-mouth or partners?
That's a good question.
How did you get the early adoption?
App Store SEO was really important to top offunnel for us.
(13:52):
If we ranked highly on the word construction,something as simple as that.
You can imagine you're working in theconstruction industry, get your mobile device,
and then you search construction because thatis your profession on the App Store and
PlanGrid is the thing that comes up.
That was really, really important to our go tomarket motion.
It was a bottoms up sale.
Someone would download a trial version ofPlanGrid.
(14:15):
They would upload their stuff and then theywould get a phone call that afternoon from
someone at our company saying, hey, who areyou?
What are you up to?
Do you need any help?
Can I help you finish uploading your stuff?
Oh, and by the way, you're on a really bigproject.
Are you sure you don't want me to send asalesperson to your job site for a lunch and
learn?
We'll bring you burritos or bring yousandwiches.
(14:36):
We'll bring you whatever you want.
Just give us thirty minutes of time.
And then that was, you know That was a salesmotion.
So in some ways, being early, having a greatproduct that people loved and then just being
sort of being commercially minded and gettingpeople to sign up helped you get early
adoption.
So you went I think you scaled to like5,000,000 ARR and then raised Series A, is
(14:57):
that?
I guess how did you learn
lot from the job.
PlanGrid was growing the whole time, so everysingle day it was the biggest job I had done
before.
I think it was really important for me to bringon a leadership team.
I probably learned the most from our CFO aboutbusiness and unit economics and why we would
(15:19):
have to think about a business this certainway, right, profitability.
And then just, like, just having really goodmanagers.
And that's probably the biggest learning afterten years in startups is getting to see the
best managers in action and then really tryingto understand what the pattern is is here.
(15:43):
And they just had all been doing it for a longtime.
Mhmm.
So they had the experience of dealing withmanaging people and all of the personalities.
They had just seen some flavor of that if whenyou when you've been doing it for twenty years.
Mhmm.
And then getting to see how they took care ofeach random situation and scenario very
(16:06):
gracefully.
And when did you, you know, when did you startto hire kind of more senior people and then the
CFO?
What stage were you?
Probably our series a because we were prettyflat prior to that.
Everyone reported to the founders.
Then we raised a series A and we needed toscale.
I remember we tripled our team that year.
(16:28):
The investors wanted us to spend money and growfaster.
And then by that point, at a 100 people we justneeded, you know, with a few founders, you just
needed another level of leadership.
And so probably our frontline managers came onat that point.
Some of them didn't work.
We hired the wrong people.
Some of them, you know, ended up takingleadership positions at the company.
Did you hire people with domain experience oryou or miss, try to avoid that?
(16:54):
Domain experience specifically withinconstruction.
Our six salespeople at PlanGrid, we decided totest out the profile.
I was a construction engineer by training, andso I was selling PlanGrid.
I mean, I sold most of PlanGrid up to5,000,000, so I was like, I'll just hire
someone that's like me with my background.
(17:16):
And tested out hiring three constructionengineers and three SaaS salespeople.
Yeah.
And these SaaS salespeople just outperformedthe construction engineers.
The three construction engineers ended uptaking like customer success support roles.
It is very hard for construction engineers tohear no day in and day out.
(17:42):
And that's just part of the job of being insales.
You brush it off and you go into your nextdemo, you get another chance to get a yes.
And that was just something they were notprogrammed to do.
These are people who had always succeeded ontheir building project.
And the sales folks from Salesforce, they werejust so used to getting no's.
Was like, whatever.
(18:02):
I actually sold some deals today, so this is agood day.
Share with me the fundraising timelines.
You raise a series A and then a series B.
And you've very successful raising money.
I guess if you were to look back and I'm sureyou made some mistakes along the way and did
some things right what advice would you givefounders from your own experience in
(18:22):
fundraising?
The advice I give founders on fundraising isyou really have to be in fundraising mode or
not in fundraising mode.
You can't be somewhere in between because itjust doesn't benefit you.
Fundraising, as you know, is a very emotionalprocess.
You are going out to investors and you aretrying to sell a piece of this thing that you
(18:43):
love, that you worked really hard on.
And they might not agree with how much youthink your shares are worth or if your business
is even viable.
And so I think there are some founders thatwill say, like, you want to build relationships
and you want to make sure the partner gets toknow you ahead of when you fundraise so that
(19:05):
the process can go faster.
But I've just found that you you never want tobe the founder on the market trying to sell a
piece of the company for six months.
Mhmm.
Because people are gonna know.
And you don't want like, time kills all deals.
That's probably the takeaway that's mostimportant when it comes to fundraising.
(19:25):
Time kills all deals, and you do not want to bethe founder trying to fundraise for six months
and being unsuccessful at it.
So run an accelerated process.
Keep it tight.
If it works, great.
If it doesn't?
Go back
to work.
Fine.
Get back to work.
Build whatever fee or improve on the feedbackyou've got and get bigger, more interesting
(19:47):
business.
Yeah.
So you raised a series A and then a series B.
Mhmm.
And just what kind of scale people were you at?
And and in terms of just that your evolution asa kind of time founder to being a scale CEO,
what were some of the lessons that you learnedin terms of bringing on executive leadership?
(20:12):
I think the biggest mistakes I've made withexecutive leadership is I knew they weren't the
right fit.
Like, something in my gut told me this is justnot the right fit, but I am so stressed out
right now and I don't want to run marketing orsales anymore and I'm just going to hire this
person because, you know, whatever.
(20:34):
They're going to do at least 75% of the job So,you know, that's that's a whole chunk off my
plate and that's the pressure off me.
And in those instances, it just doesn't reallywork out.
And that there's actually a lot of intelligencein my gut that was telling me this isn't this
isn't this is not quite right.
And then I was like lured by their fancyresumes and backgrounds.
(20:57):
If I could do it all over again in those years,I would have just done a lot more reference
checking.
And of course, you know, you call the threepeople that they give you, it's going to be
positive.
But you ask them, who else should I talk to?
Who else knows this person well?
And you call those people that's two degreesaway.
Then you ask those people, hey, who else shouldI talk to?
(21:17):
And almost always you get three degrees awayand you get much more honest conversations.
And also, you're now piecing together a muchmore full picture of who this person is and how
they are to work with and their contributionsat their last company.
Dimensionalize that.
How many if you if you were to hire a VP or Clevel person
20 people at least.
(21:38):
20 people.
Yeah.
And Because because if you you won't know for afull year if they are good or not.
You're gonna at least give them that.
And then if they're not working out in thatyear, you've just wasted time and their blast
radius is kind of big because if they're at theVP exec level, you've probably given them
budget to hire a team.
(21:58):
And so now there's other people you've got tofigure out if they're good or not and manage
them out or promote them or, you know, hopethey stay.
Yeah.
Know from experience, it's really hard.
If you make a bad decision, then it's
very the right executive and then seeing awhole department just take care of themselves
and get things done and you don't have to worryabout it again.
(22:20):
You also know how that feels and it just feelsreally good.
And was that as you as you got to kind of northof 100 and a 150 people, was that Where did you
spend your time?
I imagine you had people focus on sales andmarketing and product and HR.
What were the areas of focus that you spent ontime?
(22:42):
It really depended on where we were hurting themost.
I personally like spending my time testing outthe product and then on sales calls, talking to
users, and then figuring out how to prioritizeour product roadmap for this quarter.
That's how I like to spend my time.
But there were years where, you know, there wasno engineering leader and I had to step in as
(23:05):
interim VPE as we were doing that search for afull year.
Same thing with marketing, you know?
So it just really depends on where there's alack of leadership and where we need to airdrop
in the founders.
The outside in view of startups is that it'slike you found it, you go through or get early
funding, and then it's seven years later, it'skind of you go public or you're quiet.
(23:30):
Imagine along the way, there were someexistential moments, some moments where really
felt that this is okay.
If we don't figure this out, we're gonna gobankrupt or have to shut down.
Yeah.
And the worst moments?
The worst moments are always thinking aboutpayroll and not being able to make it.
That always feels super bad.
(23:52):
The other worst moments are just you know,there's like infighting at the company or
you're not getting along with one of the execs.
And the nice thing about being founder CEO isyou get to fix all this, especially at the
executive level.
And the signs of an exec not working out, Ithink, is when you or anyone that reports to
(24:13):
you not working out is when you start dreadinghaving one on ones with them.
That is the biggest red flag.
Because with your team, you should feel soexcited to finally get thirty minutes or an
hour to figure out what they've been up to,where the challenges are, and then also you
might need things from them and, you know, it'sa it's a partnership.
(24:33):
When you're dreading having one on ones with anexecutive, like, that is so so bad because
that's how messed up things are.
That's how messed up the relationship is.
Probably because something's not working.
And how did you obviously, perhaps inretrospect you sort of realized that those one
on one you avoided those one on ones.
(24:54):
Was that specifically a situation where youended up terminating the executive?
Or they self selected out.
They just left.
And is that just as you think about learningexperience when things are not working, is
there anything you would do differently afounder or executive?
You can never fire fast enough.
(25:15):
And the reason for this is because at thefounder CEO level, when someone isn't working
out, the people to know are the people thatreport to them.
And then it's their peers, and then it's you.
So the whole company's known that this personisn't working out.
(25:35):
You just haven't made the decision yet becauseit took a while for you to figure it out.
So by that point, it's like it's very clearwithin the organization that it's not going to
work.
And so it's just the organization just requiresyou to make the decision.
But it takes courage and sometimes, you know,it just isn't there with everything going on.
So PlanGrid scaled from zero to close to100,000,000?
(26:00):
The day we hit a 100,000,000 in ARR.
I don't know why this was so important to me.
It's a nice number.
It was the day I stepped down as CEO and passedthe baton over to the team.
And I knew we knew when it was gonna happen.
We're pretty good at forecasting.
And that gave me six months to integrate.
(26:21):
Because once we hit that mark, we really pushedfor integration into the mothership, into
Auditars, our acquirers.
So we're still we were still like a standalonestartup.
Okay.
But by that point, you're sufficient scale.
Let's leverage the mothership.
But going back a little bit, how did that whatwas the thought process around M and A?
You know, imagine you could have beenprofitable if you wanted to be profitable at
(26:45):
that point.
You had scale.
You could have raised more money.
What was the decision process around combiningforces with Autodesk?
It was a hard decision.
So I think our jobs as founders and leaders ofa company is to maximize all options available
(27:08):
to us.
While we were having conversations withAutodesk, I was also fundraising a Series C.
And part of it was just to have leverage andoptions, right, as we were negotiating.
But when we so we had a Series C term sheet,maybe two, and we had a term sheet from
(27:28):
Autodesk.
And they had given us a multiple, it was like10 something x our current revenue, our next
twelve months revenue.
This is Autodesk.
This is Autodesk.
And so it was a good offer.
And I really went and did the math.
(27:48):
You know, with the Series C, we are all goingto take a round of dilution, and then maybe a
Series D and then maybe we can take the companypublic at that point at like 200,000,000 in
ARR.
And when we did the math, it was like, wow,Autodesk's offering, like, we would have to
execute perfectly and flawlessly for the nextthree years for us to have really the same
(28:13):
financial outcome.
When we looked at the team and what, you know,you start doing the math, it's like, oh, well,
for these, like, 50 people, it's like, it'smeaningful.
Like, they can take care of people in theirlives.
And that really helped out on the decision.
Right?
Like, seeing where we were in the market andknowing that there were serious obstacles ahead
(28:38):
of us, that there was a company called Procore.
They were three times larger than us.
They were number one.
We were considered number two.
Mhmm.
And we were still growing 75% year over year,which is like not too shabby.
Yeah.
Yeah.
But I didn't know how to accelerate growth.
We really looked at every which way and wedidn't know how to do it.
(28:59):
And so there was risk to us being able toexecute flawlessly over the next three years.
And here, Autodesk was going to de risk it allfor us.
And that's a very analytical approach.
I imagine, know, this is in some ways up untilthis point, this is your life's work, and
you're building this.
So I guess, you know, how emotionally, thatmust be very hard to kind of you know, Autodesk
(29:26):
is a big corporate.
You're the pirate, the small startup.
Like, was was this something that you you'revery rational the way you describe it, but were
you under a lot of pressure from investors togo down this route or employees?
Or was something else personally was drivingthat path?
(29:48):
I think at that point, I didn't see how we weregonna be able to compete with Procore.
And I could see a world where we combined withnumber three, which was PIM three sixty, a
product owned by Autodesk.
And by the way, Autodesk was like the front endof everything we were doing.
Were the leaders in design and we were justsomehow it was somehow getting exported into
PDF and we were ingesting those PDFs.
(30:09):
So there was a very obvious product synergyhere where you just direct forget about
printing into PDF, you just direct send it overto PlanGrid, and then there goes the field
workers.
They can use PlanGrid to build.
So the product synergies was there too.
And I think the board was happy about becausewe had only raised a series b up until that
(30:30):
point.
They were happy with being acquired.
And they I remember they really wanted us toshop the deal.
Actually, all coming back to me now.
They really wanted me to go to SAP and Oracleand then try to get a higher valuation, or just
a bigger term sheet.
(30:51):
And I was really against it.
It's like, what the heck is SAP or Oracle goingto do with us?
Like, they have no interest in construction.
And they're like, it can be just twenty fourhours.
We have, like, the right phone calls, and we'llmake a phone call and just give the
presentation, and, you can just go and pitchthem.
It's like, it was so remember it being soemotional.
It was like, you don't understand.
Like, I can't do that.
(31:12):
I'm just not going to do that.
And Autodesk is the only company that actuallymakes sense for us to be acquired by.
And BIM three sixty was a separate startup?
It was another startup acquired by Autodesk.
Okay.
So you could?
We would combine it.
And that is the product today.
It's a BIM three sixty PlanGrid product renamedas I don't know what Autodesk Build.
(31:35):
Okay.
And when did Autodesk acquired BIM three sixty?
Gosh.
I want to say ten years prior to ouracquisition.
Okay.
I mean, they were working on tablet PCs, so itmust have been really old.
I know from my own experience, go, you know,truly emerging.
But Zillow was actually we were number two.
Zillow was number one.
And we spent a lot of time like okay, we wereboth public companies and so we had some
(31:57):
pressure on expenses, but the same questionlike, how do you become number one if you're
number two?
And the premium there's a real premium to benumber one.
And whether you're in marketplaces with strongnetwork effects or whether you're kind of
enterprise SaaS where you're you become thesort of, you know, the default choice, that
sort of customer choice, it's We face this verysimilar question, like how do you get to number
(32:22):
one?
And I think that and that kind of spurred alittle bit of the decision to to combine forces
with Zillow.
You start to go on this on this journey andyou're both growing, and then at some point
it's like to get into the sort of higher airrequires a different strategy, a different
approach, or enormous capital or somethingdifferent, perhaps similar dynamic.
There was a range of M and A going on in thecategory.
(32:46):
So Rupert Murdoch, within residential realestate, Rupert Murdoch were declared a decision
to buy one of the companies.
And I think everyone was teaming up for a dancepartner.
So there was like Trulia and zillowrealtor.com,which Rupert ended up buying in the end.
But you could see that there was this sort ofdislocation happening in the industry because
(33:12):
everyone was figuring out that this is a hugeprize.
And if people were not going to if you stayedalone and independent, you would struggle.
And you probably sensed that as a founder, thatyou'd like, Okay, this is status quo is
probably not an option.
(33:32):
Because you see these big forces movingquickly.
Yeah, you see the trends.
You see which segments of your business isgrowing and not growing.
And everything you're trying is just notaccelerating the growth that you want to see.
Yeah.
And I remember talking to the board, it's like,I don't know how to do this.
Can we hire a CEO?
I remember Doug Leone with Sequoia was like,CEOs are only for like founders who are shitty
(33:57):
and you're not a shitty founder.
And then I was like, okay.
Well, how about we start talking aboutsuccession, we start talking about doing a CEO
search?
Because I don't know how to get us from a 100to 500.
And
they were really against it.
Good for them.
(34:18):
Yeah.
They just didn't believe that that would makethe company successful.
So you So I was I was really out of choiceshere.
Right?
Yeah.
Yeah.
Because I think PlanGrid could have kept goinghad we had just a CEO who knew what they were
doing.
And, know, that's not to, like, talk myselfdown because I obviously, you know, not bad for
(34:40):
not having any CEO experience at the time, hadtaken the company that far.
But it was very obvious to me there needed tobe some big step changes.
I don't even I couldn't even fathom what theywould be Mhmm.
To accelerate growth and to cut costs at thecompany.
What did you and that's a very you know, tosort of think that you are not the right person
(35:03):
to necessarily scale it to become a 500,000,000revenue?
Like, what like, that's most most founders havethis unwavering belief that they can do
anything.
What how did that realization come to you?
I feel like I was just keeping it real, Pete.
(35:25):
Mhmm.
I
was just being honest with myself.
I didn't know how to do it.
I could see us steadily growing.
Right?
But you see you see us going from, like, 85%year over year growth to 75% year over year
growth, which is when we sold the companybecause our talks with Autodesk was almost a
year.
(35:47):
But to to turn that into 300 or 400% growth, Ididn't know how to do it.
And do you think the market couldn't absorb?
Because sometimes the best executives justcannot change their dynamics.
Do you think there's a belief do you think youcan do it?
(36:08):
Or do you think PlanGrid couldn't do it?
I think that it would have required a brand newexecutive team.
New product leader, new engineering leader, newsales leader, new marketing leader, new CEO,
and I thought that it would be possible in thatcase.
Because that there would be enough turbulencethere where you can really make some serious
(36:30):
changes and it would be okay.
The other option would be to join forces withAuditUS.
Mhmm.
And to compete that way.
And those are really at that point the only twooptions I saw.
I mean, of course, we could have raised aseries c and signed that term sheet.
Again, it kept on going.
But I didn't like a world where we were numbertwo and number one was four times or five times
(36:57):
bigger than us.
Yeah.
And if things started to if things continue theway that they were, then your attractiveness as
a company may go down.
Or Autodesk would make another acquisition,another space.
Did you share just your concerns about yourability to kind of reaccelerate growth with the
(37:19):
board?
Yeah.
I told them I thought we should hire, we shouldthink about hiring another CEO.
I don't know how to do it.
Was a very simple conversation.
So when the Autodesk deal came about, it wasimagine from their perspective, they're like,
Okay, the risk of changing leadership
(37:40):
Yes.
That's exactly what happened.
Is just like a level of risk that we're justnot able to because there is a ton of risk with
that Mhmm.
Versus taking the offer that's on
the table.
Right.
Right.
And I wasn't going to quit on the spot.
Was like something I wanted to plan with theboard over two years.
But the Autodesk deal happened during thattime.
And or at least Autodesk calling me happenedduring that time.
(38:04):
And so, you know, the board's immediatereaction was like, let's just put that on hold.
Let's see where this goes.
And the and how long was the dating processwith Autodesk?
It was almost a year.
We're talking about like 11 I think they justcouldn't make up their mind of who they were
going to buy if they could buy Procore orPlanGrid.
That was really why it took so long.
(38:26):
As you look back on the experience, I'm surefounders approach you for advice about how to
navigate M and A.
Is that like, in retrospect, what are thethings that you would do differently?
And perhaps in also in retrospect, like, arethe things you said, okay, that was a smart
move?
So probably wouldn't do anything differentlyjust because it was a good outcome for us.
(38:50):
And Autodesk took care of our team.
You know, I'm very happy and grateful for theoutcome.
A lot of my old teammates are leaders atAutodesk today in the construction division.
In terms of what I tell founders when they getapproached by an Autodesk or some other
potential acquirer is I tell them that it isvery, very far away from a real deal to not get
(39:18):
too excited, but their again, their jobs is tomaximize options.
And so it's really important to know who's onthe other side.
Like, if unless there's a c suite on the otherside, it's probably not a real deal.
If there's corp dev only on the other side,they're just kicking the tires.
And then I'll also remind them that theirnumber one priority is to keep all of these
(39:46):
conversations confidential because it's toodistracting for the team.
And this is what we did right.
Thanks to our CFO who had been a part ofseveral m and a deals is the only people who
knew was my co founder and our CFO during thatyear long conversation.
And was it like dinners with the CEO atWaterdesk and a lot of like
(40:07):
We had a code name for the talks.
You remember this?
What was the code name?
Do you remember?
It was some wine.
And there, I don't know, someone was into wineand
drinks, so I don't remember.
Yeah.
Okay.
And so the transaction closed, and you were a100,000,000 revenue.
What was the I listened to a few of yourpodcasts.
(40:28):
So it sounded like there was a culture clash.
You were the startup.
They were the big corporate.
How did that make you feel?
I'd never worked for a public company up untilthis point.
And it really did feel like I wasn't allowed tosneeze without checking with five heads of
divisions.
(40:48):
And then it was really hard to find time ontheir calendars.
And then we would meet for an hour.
You can imagine this is a very expensivemeeting.
And then it was like, okay, we'll scheduleanother meeting to talk more.
And that would be three months later.
And what felt like should have been just athirty minute conversation and a decision after
that.
So it was really hard for me to work at thatvelocity.
(41:14):
In hindsight, it makes sense because they havethey have to take the earnings calls every
three months and they can't make they have toreally think through each decision because
Mhmm.
Any major decision is going to probably affecttheir stock price.
And they have a fiduciary duty to all of theirshareholders to not mess up the stock price.
(41:36):
Right?
Yeah.
And that was just a perspective I did not have.
And from my perspective, it's like, why can'tyou guys make the obvious decisions?
Why do we have to keep talking about this veryobvious thing we should do?
What's wrong with you guys?
Right?
But I'm really grateful for my time therebecause I got to see how a public company
(41:57):
works.
A 50 year old company and they're, you know,they were doing a lot of good things and then
there's also a lot of room for improvement.
And so you stayed about a year?
One year.
And then you then you moved on and
I think I worked for Y Combinator after that.
Okay.
So that was a transition for you.
(42:18):
So you left and then spent some time at YC?
Investing, coaching.
I really liked the coaching part.
The investing part was much harder
for me.
Why was that?
I just never knew if I was doing a good job.
That was the hard part.
Yeah.
The feedback cycles in this industry are solong that it's so hard to know.
(42:40):
And now you're running a new startup?
Tiger Eye.
Tiger Eye.
What was, you know, ten year journey, a greatoutcome, what was and you were kind of in YC.
What was the kind of restart moment for youlike to start another company?
What was the sort of catalyst for that?
(43:02):
So we're a husband and wife team.
Ralph is also the co founder of PlanGrid.
You know, we just kept talking about thingsthat would be great for businesses.
Like, oh, this would be a really good product.
This would be cool.
This technology allows for this to happen.
What about this?
And we we just had a lot of conversationsthere.
And I think it came to a point where we were atthe decision point of whether we were gonna
(43:25):
found a new startup or not.
And for us, we really didn't want to regret notdoing it.
I didn't want to be in my seventies oreighties, hopefully even get to live that long,
and then just regret, like, oh, I wish Istarted another company to see what would
happen.
And so we just did it.
Was some of the idea just the observationwithin Autodesk and seeing, okay, this is, you
(43:51):
know, this big company should be run a lot moreefficiently.
We had a really unique perspective, which wasAutodesk had acquired, I think, three other
small startups at the time.
And so we were all coming together to formtheir new construction division.
And you can imagine three startups selling intothe construction industries, and I was in
(44:13):
charge of integrating the back office systemsas well as people.
But back office systems was really gnarly, andI remember that being really painful and knee
deep in it.
And we had all spent millions of dollars ofsetting up our Salesforce environments, and now
we were trying to merge them into one.
And I remember thinking, wow, this is look howwasteful this is.
(44:34):
Like, we had all bought the same lead list.
We had all jammed it into Salesforce, force.
And now we just like need one environment.
And so that was one problem.
Same thing existed on the ERP side.
Wow.
Look at all our reporting.
We're all trying to calculate ARR and churn andgross margin and EBITDA.
And it's like the same financial metrics thatare important to any business.
(44:58):
And it's like, now we've got to consolidatethis and reconcile it.
And it just seemed highly ineffective andwasteful and so many conversations with
everyone's data teams.
And so we wanted to build the thing out of thebox.
And as you were starting this company, Iimagine there are probably some reflections.
Okay.
These are things we did right at PlanGrid, andthen if we start a new company, we're gonna
(45:22):
definitely do it a different way.
What were the things or elements you broughtwith you to the new company?
And then what are the things like, Okay, wemessed up here.
Let's do something different.
Yeah.
We came up with a business idea.
And actually, we decided to start a startupduring 2020, which gave us a lot of time during
shelter in place to just sort of talk throughwhat we would do differently.
(45:43):
The thing we did was we whiteboarded all thenames that we wanted to work with again.
All the people that we thought were excellentand talented and hardworking and just amazing
individuals.
We put their names down.
We then wrote down and this wasn't that many,it was a much smaller population just like a
handful of names of just people we would neverwork with again.
(46:04):
And what you see is a very black and whiteworld of core values.
Like, this is why this is what makes thesepeople amazing.
They are humble.
We trust them.
They're hardworking.
You know, they're good teammates.
And you really get to have a really clearpicture of the people that you want to work
(46:25):
with again and the people that you do not.
And that was how we formed our core values.
I mean, I think we had them written down in,like, within an hour.
So it was less about the higher list, it wasmore about what is it about these people that
makes them special employers and special teammembers?
Mhmm.
And then codifying that into a set of values.
(46:45):
Set of values.
We also added in something I callwholeheartedness, which is that this time
around as parents and being startup founders,knowing how all consuming it can be, that we
also want to be good parents while we're doingthis.
And so the only way we're gonna be able to dothis is, one, of course, we have a highly
(47:05):
regimented schedule.
There's highly protected kids time and thenhighly protected work time.
Mhmm.
And we promised ourselves that we would befully in as parents and fully in as founders.
Mhmm.
And that's the concept of being wholehearted.
That your your whole heart is there.
You're not splitting it up into multipledirections trying to balance life.
(47:28):
Right?
Someone else is responsible for my kids.
I'm not thinking about them.
I'm only thinking about tiger eye during thesehours.
Mhmm.
I heard something in my research around likeyou you had like some blank grid, you had a no
jerks policy that you Oh
yeah, it was actually no assholes.
No assholes.
At some point, we had HR come in and they'relike, you can't use that word.
(47:50):
I was like, oh, I can't use that word.
Okay, no jerks.
Okay.
Whatever.
But you felt that it wasn't necessarily appliedthroughout the organization.
Yeah.
The problem with not following even one of yourcore values is the signal to the rest of the
(48:12):
team, is the other four core values is completehorseshit.
So we had this core value called neuro jerks,except you looked at the building and it was
like, wow, there's probably like three of themin the building.
And Tracy kept them there.
And so what that also signaled to the team isyou just have to perform for Tracy and you can
(48:32):
get away with murder.
And, you know, I should have just either had areally strong talk with them or just fired
them.
We did this thing at True Lessons.
Similar thing, you know, like, you start acompany, you figure out as a founder the
environment you want to work in, and then youwrite down your half a dozen values and you
(48:53):
stick them on the wall.
And some companies just forget about them andsay, these are values here.
We check.
We've done their values.
We ended up doing a company survey everyquarter.
We'd ask the whole team, like, on a scale ofone to five, how are we actually living these
values or not?
(49:15):
Exactly as you say, because there were a bunchof one of them was customer obsessed.
And there was a period of time in 2008 where wewere running out of cash.
It was like customer obsession just came downbecause we just need to pay the bills.
We weren't really improving the product.
We were just trying to sell as much as wecould.
(49:37):
But it really kept us honest about how we were.
And we shared all the results with the wholecompany.
You're running a company, you sort of the sameway you track NPS, the same way you track
funnel conversion rate, you're the sameretention, you would track these numbers
longitudinally.
It was fascinating to see that.
(49:59):
And so I'm sure that's you'll either do thatsort of implicitly from the way that you run
the company or maybe track it through some sortof survey across the organization.
There's a ton of tools out there that do thatsort of thing now.
We are so serious about our core values thetime around.
I actually have another document called OurCommitments to Each Other and people sign it
(50:21):
when they join.
Okay.
And it is written in a way where there is noambiguity on how you are to work here.
So it says things like, will walk it like Italk it.
Mhmm.
If I have a problem with a teammate, I willnever speak destructively behind their back.
And if I find one of my teammates speakingdestructively behind someone else's back, I'm
(50:42):
gonna correct them on the spot and have thembring it up with my coworker and just deal with
it.
Because we are all adults.
Mean, it's written in a much better way, butI'm giving you the summary here.
And the and the mere fact of them signing it isjust their testament to like, okay, we can live
by these values?
And they've read them and Yes.
We've had our employees bring up, like, thisperson is not living up to the values and we
(51:08):
need to get rid of them.
We by
the core values.
And what's next for TigerEye then?
I'm really interested in other industries, liketraditional industries who have historically
had very low tech adoption.
I'm very excited to talk to them because thereality is AI is like the poor man's
technology.
(51:28):
It's very fast and cheap to stand up and youcan see return on investments almost
instantaneously.
And you started Tigra in 2020, at leastconceptually, like at which point, AI, you
probably were aware of AI, but it wasn't asmainstream or as powerful as it is today.
How has your view on the opportunities with AIchanged over the last four, five years?
(51:56):
Our team's always been machine learningexperts.
You know, we've been doing old school AI.
It was November 2022 was when conversational AIwas introduced to the world.
And so there was always a lot of AI built intothe core technology.
We use simulation theory to predict the future.
(52:18):
I mean, we get a lot of prediction questions aswell.
And I think conversational AI really just helpus think differently about the user interface
of TigerEye.
The core is still there.
It's just it's very easy, right?
You now have this conversational chat box to doeverything.
(52:39):
So that part changed
Mhmm.
But in a much better way because it obviouslyis the future.
And then just going back a little bit about isyour evolution as a founder and a leader?
Like, what just is you achieving the success?
Like, what are the things that you perhapswould do differently or the things that you
(53:02):
say, well, that really helped me through thischallenging period as founder and CEO?
I remember when I was younger, the revenuemilestones were really important to me.
I mean, of course, are like hitting our targetsare important, of course.
But I was never happy.
Like, I remember telling myself, like, if wejust get to I'm so stressed out right now.
(53:24):
If I could just get to 10,000,000 in ARR andthen you get there.
And it's like, if we could just get to, like,30,000,000 in ARR, if we could just get to 50,
get to a 100, like, every time we got there, itwas just kind of it's just me, like, you know
Just a number.
It's just a number.
Exactly.
And when I think back and reflect back at myjourney as a founder, the best memories are
(53:47):
always with people.
I was building cool stuff with people.
Those are undeniably the best memories and theones I will take to my grave.
And so that's really what's different aboutTracy today than Tracy fifteen years ago.
The shared moments, the collaboration.
(54:09):
It's really important that we enjoy the ridewith the people we're building with and the
people we're building for.
And just the definition of success for you,what is that?
If you would think, okay, obviously, there'sthe financial success of Tiger Eye or startups
in general, but what does success mean to younow?
(54:30):
Yeah.
So the revenue targets are still there, hittingthem.
Success has to include the financial part.
But now, I think it also includes the humanpart that we created good jobs that people were
proud of.
I mean, I just talked to you about a teammatethat is that tiger that used to work for you
and he's very proud of what he did with thewhole team at Trulia, right?
(54:54):
Like to me, that is what success looks like.
Yeah.
You kind of have that fond experience.
Yeah, we did.
Yeah, sure.
We delighted customers.
We paid good salaries.
Stock options did well.
But then it's like the memories.
A decade later, more than a decade later, thatis what people remember.
That was a happy place.
Well, that, Tracy, thank you so much forjoining us today.
(55:17):
Amazing journey, amazing opportunities, amazingfuture ahead for TigerEye.
So thanks for joining us.
Thanks for having me, Pete.
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