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 co founder and CEO of Tiger Eye, which we're going learn about. So maybe just to start off, I'd love to hear a little bit of your background. Like, where'd you grow up? What environment was that in? And just and what was your I know you got involved 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 homelessness and just poverty, they were just right above 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 class and so as a kid, I watched how hard they worked. They worked seven days a week, in some years they were working two jobs. And I always knew I I needed to make them proud.
I loved drawing. I loved painting. I loved building as a kid. And a big part of me wanted to go to art school, but I just didn't have it in my heart to look my immigrant parents in the eyes and it'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 you're worried that they were like, okay, this house 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 would mark it up and then they would sell the goods to restaurants. And their client base was all of the other immigrants in the community. Was that in the Bay Area? In the Bay Area. Okay. So like you think about pho restaurants and like 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. And the career path is you come out of school and 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, closed toe shoes, muddy boots. Except that I'm a five foot three Asian woman Mhmm. And so I stuck out like a sore thumb on the job site.
But I had a great time. I I think I was very lucky to work in the Bay Area because you imagine that being one of the few women on a construction site with like a thousand men, that that would be hard. But I I worked with really really great construction leaders who didn't care how I looked like, they only cared about my output. And I got to learn from what I still consider today 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, and you have to understand that these superintendents probably didn't finish high school, but they went into the trades. Mhmm. So they they didn't finish high school, went to become a carpenter's apprentice, started making money, and then these would be the best of the cohorts. Right?
They would work their way up from foreman to superintendent to senior superintendent and they were like the kings of the job site. They knew everyone, everyone reported to them. They could look at a set of blueprints and have in the back of their heads exactly how they would build an entire hospital. When the medical equipment would come in, when the crane would come in, and they would have a whole full schedule in their heads. And they were master builders.
And obviously great leaders, imagine, as well. And I think just before the exit, PlanGrid was like 500 Mhmm. Ish people? Like, were there any a new scale to become a leader? Were there any sort of techniques or skills that they had that you adopted?
I think what was most impressive about the superintendents that I worked for is they were just at a place where it's very high pressure and high tension because schedule's always behind, the building owners breathing breathing down everyone's like things are always messed up. You've built something wrong and you've got to go fix it, order new materials, get the crew back in. And so it's a pretty high pressure place, but they were always steady and calm.
Mhmm. They also on top of that really cared about every builder there. Right? They knew their names. They knew their children's names and I really appreciate that human part of their leadership. Mhmm. And I think that's what I really tried to emulate. That in the day, yes, we're building this beautiful building and hopefully every subcontractor on the job site is making money while 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 the job site where we really are friends. That's great. Yeah. I think that was probably my most important learning, my time there. And so you're in this sort of great environment, 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 site into startups? I was always into projects. I always had Building stuff. Yeah. Building stuff.
And the idea for PlanGrid came when my really good friend who I'd gone to university with, Brian, he'd all He had been We've known each other since we were kids. I mean I was 17 when I met him at the university and he'd always pitched me business ideas. Like he was entrepreneurial. He knew he was going be a business leader. And, you know, 50 bad business ideas later, he finally pitched me a good one, which was let's take all of our construction record set and put it in the iPad.
Let's put it in the cloud, make it available on the iPad because that is what we would both like to use as field construction workers, construction engineers, except that it didn't exist. So why why not we be the ones to build it? And this was previously just on paper, these big 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 himself and the thing he did was he tried to load a blueprint on there. And then this box comes up and it says out of memory. And he says, we should build this. And we go through what Ryan calls a saddest story in Silicon Valley, which is two domain experts with like a decently good idea and no technical co founders to build it. And then we recruited our technical co founders. There were initially three of you? There's five of us actually.
Okay. So you hired two domain experts and you hired three engineers? Yeah. Two construction engineers, three software engineers. And then you went to you decided to apply for YC? We did. My co founder Antoine was reading hacker news every day and he really wanted to apply to Y Combinator. And he was also he had also he was also a survivor 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're gonna apply to YC.
And then we got in. And you were still at your former jobs at that point? Or you No, we had left. We got into Y Combinator, we had all quit our jobs. That was the deal. Antoine, I understand, when he was at that point 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.
You know, was like 25, 26. I'd never seen one of my friends die before. And so it was incredibly traumatic because we we were all living out of a hacker house together in Sunnyvale. And I think we just didn't know how to deal with grief. So we poured everything. Every calorie we had, we poured it into our startup. Because our friend died, and the next day, we were back supporting our customers. Was that in some ways part to to kind of deal with the grief? I think so.
And then part in his honor, potentially, in terms of just saying, okay, what would he want us to do? Yeah. I think it was it felt like at that point that if we could make this company successful, that he is a co founder of this company. I mean, his code is probably still alive and odd at us somewhere today. And we really wanted to keep his memory alive. We also just didn't know how to deal with grief.
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 time off. Yeah, yeah. Just take care of yourself. And that was exactly the conversation none of us were having. We would just work some crazy hours, and we'd sit at dinner, have a glass of wine or whiskey, and then we would just cry together, and then go to sleep, and then go back to work the next day. And we did this for months.
Were you doing your paying customers at YC? What was some of the early kind of product market fit experience? Because, you know, while the iPad is sort of a fun shiny object, construction industry has not typically been early adopters of like a software. Mhmm. What what how did you get initial traction within within the product? I think in Y Combinator, we got accepted just based off of a prototype.
And then we went back to all of our college mates and all of the people we had worked our butts off on the job site and we said, hey, we try out our product. We're building this thing called PlanGrid and we're gonna digitize a construction record set for you so you have it at your finger tips. And we'll solve the version control problem, we'll give you tools to track your your progress.
And I remember that everyone thought, of course, it was a good idea, except that no one at this point had iPads. Apple had limits on how much they could produce, and so you could only buy like three or four at a time. And so we And I wouldn't recommend startups doing this, but this is what we did to remove our own friction, which is that we maxed out my co founder's credit cards and we procured something close to like 20 iPads, which was all the money we all had at that point.
This was very precious to us. We went back to our friends and we said, what if we just loaned you an iPad? 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 the superintendents, that's also a good friend of mine, he had put in by this point, know, around the 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 it had like a PlanGrid sticker on it in a shadow 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 and connections. Yeah. How did we so they were using it for free. You know, at some point, they just said the words like, I love this. I love PlanGrid. I'm not sure, like, how we were building without this thing.
And just the modern design touch interface to kinda 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 has something that looks like PlanGrid. But at the time, we were the thing that rendered blueprints the fastest and that was 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 subs and GCs, people were interested in this new shiny object. And they're interested in how people are doing it. So was it fairly viral? Or did you have to kind of do quite a lot of enterprise sales into this customer segment?
You know, we had something called the iPad mini deal, which was you would buy a certain number of years of PlanGrid upfront. And then we would throw in an iPad Mini. And we shipped something like 10,000 iPads alone for actually the Apple Store in San Francisco, which was the partner we worked with. But was that sort of a top down sales motion or was 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 of funnel for us. If we ranked highly on the word construction, something as simple as that. You can imagine you're working in the construction industry, get your mobile device, and then you search construction because that is your profession on the App Store and PlanGrid is the thing that comes up. That was really, really important to our go to market motion. It was a bottoms up sale. Someone would download a trial version of PlanGrid.
They would upload their stuff and then they would get a phone call that afternoon from someone at our company saying, hey, who are you? 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 big project. Are you sure you don't want me to send a salesperson to your job site for a lunch and learn? We'll bring you burritos or bring you sandwiches. We'll bring you whatever you want. Just give us thirty minutes of time.
And then that was, you know That was a sales motion. So in some ways, being early, having a great product that people loved and then just being sort of being commercially minded and getting people to sign up helped you get early adoption. So you went I think you scaled to like 5,000,000 ARR and then raised Series A, is that? I guess how did you learn lot from the job. PlanGrid was growing the whole time, so every single day it was the biggest job I had done before.
I think it was really important for me to bring on a leadership team. I probably learned the most from our CFO about business and unit economics and why we would have to think about a business this certain way, right, profitability. And then just, like, just having really good managers. And that's probably the biggest learning after ten years in startups is getting to see the best managers in action and then really trying to understand what the pattern is is here.
And they just had all been doing it for a long time. Mhmm. So they had the experience of dealing with managing people and all of the personalities. They had just seen some flavor of that if when you when you've been doing it for twenty years. Mhmm. And then getting to see how they took care of each random situation and scenario very gracefully. And when did you, you know, when did you start to hire kind of more senior people and then the CFO? What stage were you?
Probably our series a because we were pretty flat prior to that. Everyone reported to the founders. Then we raised a series A and we needed to scale. I remember we tripled our team that year. The investors wanted us to spend money and grow faster. And then by that point, at a 100 people we just needed, you know, with a few founders, you just needed another level of leadership. And so probably our frontline managers came on at that point. Some of them didn't work. We hired the wrong people.
Some of them, you know, ended up taking leadership positions at the company. Did you hire people with domain experience or you or miss, try to avoid that? Domain experience specifically within construction. Our six salespeople at PlanGrid, we decided to test out the profile. I was a construction engineer by training, and so I was selling PlanGrid. I mean, I sold most of PlanGrid up to 5,000,000, so I was like, I'll just hire someone that's like me with my background.
And tested out hiring three construction engineers and three SaaS salespeople. Yeah. And these SaaS salespeople just outperformed the construction engineers. The three construction engineers ended up taking like customer success support roles. It is very hard for construction engineers to hear no day in and day out. And that's just part of the job of being in sales. You brush it off and you go into your next demo, you get another chance to get a yes.
And that was just something they were not programmed to do. These are people who had always succeeded on their building project. And the sales folks from Salesforce, they were just so used to getting no's. Was like, whatever. I actually sold some deals today, so this is a good 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 sure you made some mistakes along the way and did some things right what advice would you give founders from your own experience in fundraising? The advice I give founders on fundraising is you really have to be in fundraising mode or not in fundraising mode. You can't be somewhere in between because it just doesn't benefit you. Fundraising, as you know, is a very emotional process.
You are going out to investors and you are trying to sell a piece of this thing that you love, that you worked really hard on. And they might not agree with how much you think your shares are worth or if your business is even viable. And so I think there are some founders that will say, like, you want to build relationships and you want to make sure the partner gets to know you ahead of when you fundraise so that the process can go faster.
But I've just found that you you never want to be 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 most important when it comes to fundraising. Time kills all deals, and you do not want to be the 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 feedback you've got and get bigger, more interesting 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 as a kind of time founder to being a scale CEO, what were some of the lessons that you learned in terms of bringing on executive leadership?
I think the biggest mistakes I've made with executive leadership is I knew they weren't the right fit. Like, something in my gut told me this is just not the right fit, but I am so stressed out right now and I don't want to run marketing or sales anymore and I'm just going to hire this person because, you know, whatever. 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 really work out. And that there's actually a lot of intelligence in 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 fancy resumes and backgrounds. 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 three people 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 degrees away. Then you ask those people, hey, who else should I talk to? And almost always you get three degrees away and you get much more honest conversations. And also, you're now piecing together a much more full picture of who this person is and how they are to work with and their contributions at their last company. Dimensionalize that. How many if you if you were to hire a VP or C level person 20 people at least.
20 people. Yeah. And Because because if you you won't know for a full year if they are good or not. You're gonna at least give them that. And then if they're not working out in that year, you've just wasted time and their blast radius is kind of big because if they're at the VP exec level, you've probably given them budget to hire a team. And so now there's other people you've got to figure out if they're good or not and manage them out or promote them or, you know, hope they 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 a whole department just take care of themselves and get things done and you don't have to worry about it again. You also know how that feels and it just feels really good. And was that as you as you got to kind of north of 100 and a 150 people, was that Where did you spend your time? I imagine you had people focus on sales and marketing and product and HR.
What were the areas of focus that you spent on time? It really depended on where we were hurting the most. I personally like spending my time testing out the product and then on sales calls, talking to users, and then figuring out how to prioritize our product roadmap for this quarter. That's how I like to spend my time. But there were years where, you know, there was no engineering leader and I had to step in as interim VPE as we were doing that search for a full year.
Same thing with marketing, you know? So it just really depends on where there's a lack of leadership and where we need to airdrop in the founders. The outside in view of startups is that it's like you found it, you go through or get early funding, and then it's seven years later, it's kind of you go public or you're quiet. Imagine along the way, there were some existential moments, some moments where really felt that this is okay.
If we don't figure this out, we're gonna go bankrupt or have to shut down. Yeah. And the worst moments? The worst moments are always thinking about payroll and not being able to make it. That always feels super bad. 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 is you get to fix all this, especially at the executive level.
And the signs of an exec not working out, I think, is when you or anyone that reports to you not working out is when you start dreading having one on ones with them. That is the biggest red flag. Because with your team, you should feel so excited 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's a it's a partnership.
When you're dreading having one on ones with an executive, 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 in retrospect you sort of realized that those one on one you avoided those one on ones. Was that specifically a situation where you ended up terminating the executive? Or they self selected out. They just left.
And is that just as you think about learning experience when things are not working, is there anything you would do differently a founder or executive? You can never fire fast enough. And the reason for this is because at the founder CEO level, when someone isn't working out, the people to know are the people that report to them. And then it's their peers, and then it's you. So the whole company's known that this person isn't working out.
You just haven't made the decision yet because it took a while for you to figure it out. So by that point, it's like it's very clear within the organization that it's not going to work. And so it's just the organization just requires you 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 to 100,000,000? 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 passed the 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. Because once we hit that mark, we really pushed for integration into the mothership, into Auditars, our acquirers. So we're still we were still like a standalone startup. Okay. But by that point, you're sufficient scale. Let's leverage the mothership.
But going back a little bit, how did that what was the thought process around M and A? You know, imagine you could have been profitable if you wanted to be profitable at that point. You had scale. You could have raised more money. What was the decision process around combining forces with Autodesk? It was a hard decision. So I think our jobs as founders and leaders of a company is to maximize all options available to us.
While we were having conversations with Autodesk, I was also fundraising a Series C. And part of it was just to have leverage and options, 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 Autodesk. And they had given us a multiple, it was like 10 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.
You know, with the Series C, we are all going to take a round of dilution, and then maybe a Series D and then maybe we can take the company public 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 next three years for us to have really the same 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's meaningful. Like, they can take care of people in their lives. And that really helped out on the decision. Right? Like, seeing where we were in the market and knowing that there were serious obstacles ahead 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 we didn't know how to do it. And so there was risk to us being able to execute flawlessly over the next three years. And here, Autodesk was going to de risk it all for us. And that's a very analytical approach. I imagine, know, this is in some ways up until this point, this is your life's work, and you're building this.
So I guess, you know, how emotionally, that must be very hard to kind of you know, Autodesk is a big corporate. You're the pirate, the small startup. Like, was was this something that you you're very rational the way you describe it, but were you under a lot of pressure from investors to go down this route or employees? Or was something else personally was driving that path? I think at that point, I didn't see how we were gonna be able to compete with Procore.
And I could see a world where we combined with number three, which was PIM three sixty, a product owned by Autodesk. And by the way, Autodesk was like the front end of everything we were doing. Were the leaders in design and we were just somehow it was somehow getting exported into PDF and we were ingesting those PDFs.
So there was a very obvious product synergy here where you just direct forget about printing into PDF, you just direct send it over to 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 because we had only raised a series b up until that point. They were happy with being acquired. And they I remember they really wanted us to shop the deal. Actually, all coming back to me now.
They really wanted me to go to SAP and Oracle and then try to get a higher valuation, or just a bigger term sheet. And I was really against it. It's like, what the heck is SAP or Oracle going to do with us? Like, they have no interest in construction. And they're like, it can be just twenty four hours. We have, like, the right phone calls, and we'll make a phone call and just give the presentation, and, you can just go and pitch them. It's like, it was so remember it being so emotional.
It was like, you don't understand. Like, I can't do that. I'm just not going to do that. And Autodesk is the only company that actually makes 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 renamed as I don't know what Autodesk Build. Okay. And when did Autodesk acquired BIM three sixty?
Gosh. I want to say ten years prior to our acquisition. Okay. I mean, they were working on tablet PCs, so it must 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 were both public companies and so we had some pressure on expenses, but the same question like, how do you become number one if you're number two?
And the premium there's a real premium to be number one. And whether you're in marketplaces with strong network effects or whether you're kind of enterprise SaaS where you're you become the sort of, you know, the default choice, that sort of customer choice, it's We face this very similar question, like how do you get to number one? And I think that and that kind of spurred a little bit of the decision to to combine forces with Zillow.
You start to go on this on this journey and you're both growing, and then at some point it's like to get into the sort of higher air requires a different strategy, a different approach, or enormous capital or something different, perhaps similar dynamic. There was a range of M and A going on in the category. So Rupert Murdoch, within residential real estate, Rupert Murdoch were declared a decision to buy one of the companies. And I think everyone was teaming up for a dance partner.
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 of dislocation happening in the industry because everyone was figuring out that this is a huge prize. And if people were not going to if you stayed alone and independent, you would struggle. And you probably sensed that as a founder, that you'd like, Okay, this is status quo is probably not an option. Because you see these big forces moving quickly.
Yeah, you see the trends. You see which segments of your business is growing and not growing. And everything you're trying is just not accelerating 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 and you're not a shitty founder. And then I was like, okay.
Well, how about we start talking about succession, we start talking about doing a CEO search? Because I don't know how to get us from a 100 to 500. And they were really against it. Good for them. Yeah. They just didn't believe that that would make the company successful. So you So I was I was really out of choices here. Right? Yeah. Yeah. Because I think PlanGrid could have kept going had we had just a CEO who knew what they were doing.
And, know, that's not to, like, talk myself down because I obviously, you know, not bad for not having any CEO experience at the time, had taken the company that far. But it was very obvious to me there needed to be some big step changes. I don't even I couldn't even fathom what they would be Mhmm. To accelerate growth and to cut costs at the company.
What did you and that's a very you know, to sort of think that you are not the right person to necessarily scale it to become a 500,000,000 revenue? Like, what like, that's most most founders have this 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. 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 company because our talks with Autodesk was almost a year. But to to turn that into 300 or 400% growth, I didn't know how to do it. And do you think the market couldn't absorb? Because sometimes the best executives just cannot change their dynamics. Do you think there's a belief do you think you can do it? Or do you think PlanGrid couldn't do it?
I think that it would have required a brand new executive team. New product leader, new engineering leader, new sales leader, new marketing leader, new CEO, and I thought that it would be possible in that case. Because that there would be enough turbulence there where you can really make some serious changes and it would be okay. The other option would be to join forces with AuditUS. Mhmm. And to compete that way. And those are really at that point the only two options I saw.
I mean, of course, we could have raised a series c and signed that term sheet. Again, it kept on going. But I didn't like a world where we were number two and number one was four times or five times bigger than us. Yeah. And if things started to if things continue the way 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 your ability to kind of reaccelerate growth with the board?
Yeah. I told them I thought we should hire, we should think 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 was imagine from their perspective, they're like, Okay, the risk of changing leadership Yes. That's exactly what happened. Is just like a level of risk that we're just not 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 the board over two years. But the Autodesk deal happened during that time. And or at least Autodesk calling me happened during that time. And so, you know, the board's immediate reaction was like, let's just put that on hold. Let's see where this goes. And the and how long was the dating process with Autodesk? It was almost a year.
We're talking about like 11 I think they just couldn't make up their mind of who they were going to buy if they could buy Procore or PlanGrid. That was really why it took so long. As you look back on the experience, I'm sure founders approach you for advice about how to navigate M and A. Is that like, in retrospect, what are the things that you would do differently? And perhaps in also in retrospect, like, are the things you said, okay, that was a smart move?
So probably wouldn't do anything differently just because it was a good outcome for us. And Autodesk took care of our team. You know, I'm very happy and grateful for the outcome. A lot of my old teammates are leaders at Autodesk today in the construction division.
In terms of what I tell founders when they get approached by an Autodesk or some other potential acquirer is I tell them that it is very, very far away from a real deal to not get too excited, but their again, their jobs is to maximize options. And so it's really important to know who's on the other side. Like, if unless there's a c suite on the other side, 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 their number one priority is to keep all of these conversations confidential because it's too distracting for the team. And this is what we did right. Thanks to our CFO who had been a part of several m and a deals is the only people who knew was my co founder and our CFO during that year long conversation. And was it like dinners with the CEO at Waterdesk and a lot of like 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 wine and drinks, so I don't remember. Yeah. Okay. And so the transaction closed, and you were a 100,000,000 revenue. What was the I listened to a few of your podcasts. 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 until this point.
And it really did feel like I wasn't allowed to sneeze without checking with five heads of divisions. And then it was really hard to find time on their calendars. And then we would meet for an hour. You can imagine this is a very expensive meeting. And then it was like, okay, we'll schedule another meeting to talk more. And that would be three months later. And what felt like should have been just a thirty minute conversation and a decision after that.
So it was really hard for me to work at that velocity. In hindsight, it makes sense because they have they have to take the earnings calls every three months and they can't make they have to really think through each decision because Mhmm. Any major decision is going to probably affect their stock price. And they have a fiduciary duty to all of their shareholders to not mess up the stock price. Right? Yeah. And that was just a perspective I did not have.
And from my perspective, it's like, why can't you guys make the obvious decisions? Why do we have to keep talking about this very obvious thing we should do? What's wrong with you guys? Right? But I'm really grateful for my time there because I got to see how a public company 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. 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 so long that it's so hard to know. And now you're running a new startup?
Tiger Eye. Tiger Eye. What was, you know, ten year journey, a great outcome, what was and you were kind of in YC. What was the kind of restart moment for you like to start another company? What was the sort of catalyst for that? So we're a husband and wife team. Ralph is also the co founder of PlanGrid. You know, we just kept talking about things that 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 conversations there. And I think it came to a point where we were at the decision point of whether we were gonna found a new startup or not. And for us, we really didn't want to regret not doing it. I didn't want to be in my seventies or eighties, hopefully even get to live that long, and then just regret, like, oh, I wish I started another company to see what would happen. And so we just did it.
Was some of the idea just the observation within Autodesk and seeing, okay, this is, you know, this big company should be run a lot more efficiently. We had a really unique perspective, which was Autodesk had acquired, I think, three other small startups at the time. And so we were all coming together to form their new construction division. And you can imagine three startups selling into the construction industries, and I was in charge of integrating the back office systems as well as people.
But back office systems was really gnarly, and I remember that being really painful and knee deep in it. And we had all spent millions of dollars of setting up our Salesforce environments, and now we were trying to merge them into one. And I remember thinking, wow, this is look how wasteful this is. 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 and gross margin and EBITDA. And it's like the same financial metrics that are important to any business. And it's like, now we've got to consolidate this and reconcile it. And it just seemed highly ineffective and wasteful and so many conversations with everyone's data teams. And so we wanted to build the thing out of the box. And as you were starting this company, I imagine there are probably some reflections.
Okay. These are things we did right at PlanGrid, and then if we start a new company, we're gonna definitely do it a different way. What were the things or elements you brought with you to the new company? And then what are the things like, Okay, we messed up here. Let's do something different. Yeah. We came up with a business idea.
And actually, we decided to start a startup during 2020, which gave us a lot of time during shelter in place to just sort of talk through what we would do differently. The thing we did was we whiteboarded all the names that we wanted to work with again. All the people that we thought were excellent and 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 never work with again. And what you see is a very black and white world of core values. Like, this is why this is what makes these people amazing. They are humble. We trust them. They're hardworking. You know, they're good teammates. And you really get to have a really clear picture of the people that you want to work 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 was more about what is it about these people that makes them special employers and special team members? Mhmm. And then codifying that into a set of values. Set of values.
We also added in something I call wholeheartedness, 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 doing this. And so the only way we're gonna be able to do this is, one, of course, we have a highly regimented schedule. There's highly protected kids time and then highly protected work time. Mhmm. And we promised ourselves that we would be fully 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 multiple directions trying to balance life. Right? Someone else is responsible for my kids. I'm not thinking about them. I'm only thinking about tiger eye during these hours. Mhmm. I heard something in my research around like you 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're like, you can't use that word. I was like, oh, I can't use that word. Okay, no jerks. Okay. Whatever. But you felt that it wasn't necessarily applied throughout the organization. Yeah. The problem with not following even one of your core values is the signal to the rest of the team, is the other four core values is complete horseshit.
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 them in the building. And Tracy kept them there. And so what that also signaled to the team is you just have to perform for Tracy and you can get away with murder. And, you know, I should have just either had a really strong talk with them or just fired them. We did this thing at True Lessons.
Similar thing, you know, like, you start a company, you figure out as a founder the environment you want to work in, and then you write down your half a dozen values and you stick them on the wall. And some companies just forget about them and say, these are values here. We check. We've done their values. We ended up doing a company survey every quarter. We'd ask the whole team, like, on a scale of one to five, how are we actually living these values or not?
Exactly as you say, because there were a bunch of one of them was customer obsessed. And there was a period of time in 2008 where we were running out of cash. It was like customer obsession just came down because we just need to pay the bills. We weren't really improving the product. We were just trying to sell as much as we could. But it really kept us honest about how we were. And we shared all the results with the whole company.
You're running a company, you sort of the same way you track NPS, the same way you track funnel conversion rate, you're the same retention, you would track these numbers longitudinally. It was fascinating to see that. And so I'm sure that's you'll either do that sort of implicitly from the way that you run the company or maybe track it through some sort of survey across the organization. There's a ton of tools out there that do that sort of thing now.
We are so serious about our core values the time around. I actually have another document called Our Commitments to Each Other and people sign it when they join. Okay. And it is written in a way where there is no ambiguity on how you are to work here. So it says things like, will walk it like I talk it. Mhmm. If I have a problem with a teammate, I will never speak destructively behind their back.
And if I find one of my teammates speaking destructively behind someone else's back, I'm gonna correct them on the spot and have them bring it up with my coworker and just deal with it. Because we are all adults. Mean, it's written in a much better way, but I'm giving you the summary here. And the and the mere fact of them signing it is just 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, this person is not living up to the values and we 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, like traditional industries who have historically had very low tech adoption. I'm very excited to talk to them because the reality is AI is like the poor man's technology. It's very fast and cheap to stand up and you can see return on investments almost instantaneously.
And you started Tigra in 2020, at least conceptually, like at which point, AI, you probably were aware of AI, but it wasn't as mainstream or as powerful as it is today. How has your view on the opportunities with AI changed over the last four, five years? Our team's always been machine learning experts. You know, we've been doing old school AI. It was November 2022 was when conversational AI was introduced to the world. And so there was always a lot of AI built into the core technology.
We use simulation theory to predict the future. I mean, we get a lot of prediction questions as well. And I think conversational AI really just help us 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 do everything. So that part changed Mhmm. But in a much better way because it obviously is the future.
And then just going back a little bit about is your evolution as a founder and a leader? Like, what just is you achieving the success? Like, what are the things that you perhaps would do differently or the things that you say, well, that really helped me through this challenging period as founder and CEO? I remember when I was younger, the revenue milestones were really important to me. I mean, of course, are like hitting our targets are important, of course. But I was never happy.
Like, I remember telling myself, like, if we just get to I'm so stressed out right now. If I could just get to 10,000,000 in ARR and then 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, it was 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 my journey as a founder, the best memories are always with people.
I was building cool stuff with people. Those are undeniably the best memories and the ones I will take to my grave. And so that's really what's different about Tracy today than Tracy fifteen years ago. The shared moments, the collaboration. It's really important that we enjoy the ride with 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's the financial success of Tiger Eye or startups in general, but what does success mean to you now? Yeah. So the revenue targets are still there, hitting them. Success has to include the financial part. But now, I think it also includes the human part that we created good jobs that people were proud of.
I mean, I just talked to you about a teammate that is that tiger that used to work for you and he's very proud of what he did with the whole team at Trulia, right? 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, that is what people remember. That was a happy place.
Well, that, Tracy, thank you so much for joining us today. Amazing journey, amazing opportunities, amazing future ahead for TigerEye. So thanks for joining us. Thanks for having me, Pete.