Logan: I shouldn't have signed a term sheet so fast. Three days is crazy. I signed the one with the heart on it because I thought it signaled that they cared more.
Logan: Welcome to the Logan Bartlett show. On this episode, what you're going to hear is a conversation I have with Tracy Young. Now, Tracy is the co founder and CEO of TigerEye, a business that recently launched from stealth.
Before that, she was the co founder and CEO of. PlanGrid, a company that sold for 875 million to Autodesk in 2019. Tracy and I talk about a number of different core operating principles, including her belief that you shouldn't innovate around creative org structures, when and how to sell your business and the process that PlanGrid went through in selling to Autodesk.
We go back to the early days of PlanGrid. It was four co founders and Tracy living in a hacker house together when one of her co founders was diagnosed with cancer, ultimately receiving hospice care while they were going through Y Combinator before he ultimately passed. We talk about the advice that he gave Tracy and how that impacted PlanGrid's journey.
to the business that it ultimately became. He says, life is short, take care of Ralphie. I've since revised it to take care of the ones you love. Don't be afraid to try new things and never do anything that makes you unhappy. And it was his gift to me before he left. Really powerful conversation with Tracy that goes into what she learned from her first go round at PlanGrid that she's changing now that she has TigerEye.
We ran our startup as if it was Star Trek and you were in operations. or engineering. No one had job titles. We were so proud of this. We thought this was like a selling point to candidates. We were trying to recruit
Logan: Tracy, thanks for doing this.
Logan: there was a point in the journey of founding plan grid that, uh, you said you actually lost product market fit. You were north of 50 million in revenue growing quickly, and it sounds like you maybe realized that you didn't have the same fit in the market that you once did.
Can you go back to that moment and tell me what led to that realization?
Tracy: So if you have any success at all, especially in enterprise software, you're going to wake up one day and there's going to be just a dozen rip offs of what you've built. Um, we were really good at building software for the end user, people who take showers at night, people who work a hard days in hard hat, muddy boots, safety vests, safety glasses.
Logan: actual construction workers. The actual construction workers.
Tracy: And, um, we just completely ignored the buyer in the office. They take showers in the morning like that's not who we build software for and we woke up one day in about 2015 and VCs had dumped so much money into construction technology That everyone had just a copycat of our product and then something else some other flavor to it didn't work as well, of course and We had one competitor in particular Procore who was an incumbent They had been around over a decade longer than us You With a very broad platform and an enterprise ready product, we had a product that was very much loved by the end user.
If you were using plan grid in 2015, it's because you loved the product and you wanted to use it for your job. If you were using our competitors product in 2015. It was because someone else at headquarters told you you had to use it. Well, that's nice, except that that person in the office became the buyer of construction software.
And, um, our product was not ready for, for that buyer. I mean, we didn't, we, wasn't that we didn't care about security, or like admin consoles and enterprise features. It was just that we always pushed it off on our roadmap. We always prioritized. Functionality for the user in the field.
Logan: did the market shift or, uh, or did you find a different customer type? Did you go up market and that considerations changed?
Tracy: Oh, that's a good question. And, um, you point out something that's important. We were, at this point, we were at about 50 million in ARR. And as we're trying to continue growth in the next few years, Yeah, it was very clear to us we needed to go upmarket to the enterprise. We didn't realize that the entire industry would shift so quickly from moving buying decision that was happening in the field for so many years up to the CIOs and VP of Operations in the office.
That was surprising to us. It was almost as if overnight everyone started reading the funding announcements at headquarters of construction companies. And realizing that, oh, that's my job actually, I should be choosing software. And so we would get calls from CIOs saying, Are you seriously selling a thousand licenses to us one at a time in the field?
And it's like, yeah, that's what we've done. Would you like to negotiate a better deal with us? But these were not friendly conversations.
Logan: So the, uh, the incumbents pro core, they had the, the security and the role based access and the permissioning and all that stuff that resonated with the buyer. Sure. in the office, the person that showered in the morning versus showered at night. And you were beloved out in the field, but didn't have that.
And so it shifted from underneath you. What did you do at that point in time? How did you actually realize that this had happened?
Tracy: Well, we we did exactly what you pointed out was we ran the enterprise playbook. We got SOC 2 type 2 certification. We got ISO 27002 certification. You know, we suddenly cared about GDPR, especially going towards the international markets and certainly Building out permissions controls and role based access control was suddenly important to us as part of our strategy and roadmap.
Logan: something you could have done sooner to catch that in retrospect or was it? I
Tracy: Um, I think, for sure, the answer is yes. I think we had to have gone where it hurt. We had all these feature requests to make the product better. And we were so laser focused on that, that we just ignored the signals in the market because it was painful. We had to build out an enterprise team. Our team wanted, we had so sold them on this opportunity to make this entire industry more productive.
No one on our team wanted to build out enterprise features. That's like boring stuff, right? And so we needed to recruit an enterprise team and invest in an enterprise team to focus on these, Products that not really anyone cared about. I mean, not, not our, our internal team, of course, and it was really painful.
And I think for. For me, it was like, let's just ignore that. Let's build all this other cool stuff for our end user. And it was the wrong decision. We should have been investing in both.
Logan: The advice, uh, that you often hear, and it's kind of a platitude, but it's like, delight your, your customer, delight your end user.
And it's counterintuitive in some ways that if, if you had just focused on your end user, that's what you did. And it actually led to the market shifting out from underneath you.
Logan: I'm not sure if there's any, takeaways that are broadly applicable to other companies or now as you're, you're starting a new business.
Like, is there any lesson or was that a one off like unique moment in time? Cloud construction, it just sort of
Tracy: Yeah. I think the Kaizen and the, the, um, edit to delight your end user is delight your end user and delight the sales order form signer, the money person, and delight the person who's going to deploy and train your software.
Logan: So three different constituents and all that Kaizen continuous improvement, a Japanese phrase. Now it's one of your cultural tenants at tiger eye, right? So, um, yeah, it's interesting because those are three discreet people. Sometimes they're the same ones. I think security oftentimes can be You know, they can have the same buyer, be the decision maker, be the end user in some cases, but in, in a bunch of different markets, the, the CROs that maybe the person writing the check, uh, but the VP of ops is the person implementing it or something along the way.
Tracy: Yeah. What we have to understand is, um, there's multiple buyers. In enterprise software, there's the end user, there's the person who trains, there's the person who actually physically finds where the budget is and pays for it.
Logan: I heard you say that you found yourself in a feature by feature battle with incumbents in your space and it wasn't something you ever wanted to do again.
Is that, is that playing on their terms to some extent and you need to, you wanted to shift the conversation more than you did.
Tracy: battle because for us, another company had 15 years head start of us. It was going to be very hard for us to catch up. Um, it did 50 things. We did five things really well and the other 45 things we frankly didn't care about, nor did we think was valuable.
But you can imagine on a paper checklist, doing a bake off between the software solutions for someone in the office who's not the end user, it's like, well, look at the value here. They do 50 things. And so that was a battle I would like to not be a part of again.
Tracy: But knowing that I am going into a highly penetrated.
Space, um, in sort of, and I haven't talked about what TigerEye does, but, um, going into any enterprise software, like horizontal solution, there's going to be a lot of incumbents, especially if you're adjacent to CRM and ERP. Um, and so it's one of the reasons why we spent two years heads down building out our platform because I didn't want to go into the market with a point solution again. That's not interesting.
Logan: And so how do you think about shifting that discussion now? And maybe this is a good opportunity to, we'll, we'll dive into it and more, uh, in earnest, but, um, what TigerEye is doing and shifting that conversation.
So you're no longer batter battling an incumbent on a feature by feature, but instead helping
Tracy: It's an architectural battle. And our solution is a time series database that understands and accounts for time. And we can use it using machine learning and advanced statistics to do very interesting things that are actually valuable for the end user.
Logan: And that's a, uh, kind of a nerdy in the details, uh, thing here. But, um, a lot of the existing systems time is not a component of the underlying data structure. And so when you're trying to do things within Salesforce, for example, it requires a lot of rights and timestamps to capture what did this look like once upon a time.
It's why you can't go back and do a pipeline visibility at a point in the past if you didn't do it. Already. Right. And so there's, there's these database underlying considerations that exist within salesforce. And it sounds like you guys are now solving some of these
Tracy: It was very annoying to me as I was running my last startup for nearly 10 years to have incredibly brilliant, Data scientists and finance and rev ops analysts who would hand me spreadsheets with the title, whatever it was, it would have a date, it would have like version five and just basically telling me, I don't know if this is current or not, this data is from a week ago.
And it's because again, these are databases and when you snapshot, it's just a moment in time. Well, time passes, you close more business, hopefully every day, every minute. And suddenly what they've been working on is incredibly outdated.
Logan: they've been working on is incredibly outdated.
Logan: More than once is the idealistic approach of org structures and, uh, mid level management and no salespeople and all of that. It sounds like you're a converted, uh, you've converted from that, from that past ways of, of thinking.
But in the early days, you guys were pretty dogmatic about no mid level management, flat org structure, no salespeople.
Tracy: So my biggest lesson here is be creative about the problem we're solving for our end users. Be creative about the technology solution that we are building. Don't be creative about org structures. There's a reason why MBA programs exist. Um, and in the early days, I mean, we were all engineers, all the founders of PlanGrid.
We would say crazy things like We're never going to hire MBAs. I don't even know why we said that. I mean, you know, at TigerEye, I think our number two, number three employee had an MBA, and this is someone who is incredibly responsible, incredibly hardworking, and I get to learn from him every single day.
Um, we wanted to be so creative about how we organized our team, and we were less than 30 people. Um, we would tell, we would brag about this. We like, we, we spoke of this in pride. We ran our startup as if it was Star Trek and you were in operations or engineering. No one had job titles. We were so proud of this.
We thought this was like a selling point to candidates. We were trying to recruit, right? You're going to come in, forget about your senior engineer title. There's no titles here. You're on team engineering. And that's really cute and all until. You get to 30 people and the first person who comes up to me and says like, What's my career path here?
And I remember feeling so insulted at that time. This must have been like 2012, 2013. It's like, there's so much work to do. Why do you care about your job title? But in reality, the most ambitious people and some of the best people will care about that stuff. And if you want to retain them, you have to care about it too.
Logan: care about that stuff. And if you want to retain them, you have to care about it too. Very expensive because they can introduce a ton of complexity potentially and so you should be very deliberate with when you give them out don't treat them as cheap.
Did this lesson lead you to thinking that titles were more expensive and that you should be if you're going to call someone a VP. Make sure that you really think it's clearing the bar because everyone's gonna look at the lowest person with the VP title and say, well, I'm better than that person. So I should be a VP as well.
Tracy: Yeah, it's like, it's really popular to have the title head of something, right? So we can get away from the VP, the C suite conversation. What is my take on this? Um, I think if, if we're customer facing and I don't know, titles somehow help the conversation in a positive way, then like, who cares? Just have the title that the customer wants to see.
And so they're cheap in that side of the business. I think levels are really important for many reasons. Um, but yeah, um, I think it's important to be thoughtful about it. And as you hinted, it's because there's gonna be emotional challenges that come up. And, you know, it's gonna rub someone's ego the wrong way when they look at their title compared to someone else's.
And so it's important that we're thoughtful about it.
Logan: Was there a point in time on the sales journey that you converted to saying we need sales people or was it an evolution? Like, was there a specific moment that you're like, Oh, gosh, we can't deal with all these inbound. Requests coming in. Interesting
Tracy: We're really interesting in that we, in our last company, PlanGrid, we founded the company in 2011.
We went through YC's Winter 2012 program, um, we fundraised our seed round shortly after and we were making real revenue at that point. And then our first quota caring salesperson came in the building January 1st, 2015.
Logan: Wow.
Tracy: So that's a long time to go without salespeople. We got to 5 million in ARR before we raised a Series A and That round was led by Sequoia Capital and they're just like, you're, you need to hire a sales team.
You need to hire a sales leader. Like let's grow a sales team cause you've got product market fit. I think I thought that we could run a lifestyle business. We were having a bunch of fun. Building software for the construction industry with a relatively small team for how much money we were making, we were cashflow positive for all those years.
And, um, in reality, um, in the enterprise software business, there is one big gorilla of a winner, and then a second and third place, and there's room for a second and third place, luckily. And then just a lot of smaller companies just waiting to die a slow death. And that wasn't obvious to me until, I think, ten years into the company.
Logan: Still, I mean, remarkable just to say those numbers out loud that you were got to 5, 000, 000 in recurring revenue, cashflow positive with, uh, with no salespeople in place.
I see why
Tracy: We, we had, so to be clear, there was no quota carrying salespeople, we didn't pay out commissions. But there were many of us doing the sales role, right? We were all trained on the operations side, if you remember, that side of the house. Everyone knew how to do customer support. Everyone basically did every marketing and sales effort.
We would demo the software. We would show people how to use it. We would train customers. Um, we had people doing sales. We just didn't have a formalized sales team.
Logan: Got it. Got it. Um, so.
Logan: Plain grid ultimately had a very successful outcome sold for 875 million to Autodesk, only 66 million raised. So great outcome for Sequoia and your, all your investors, I'm sure for the, for the co founders as well.
Um, that said, I realized it was an incredibly difficult decision to sell. I think, um, around that time I was actually at battery ventures and I think we had a term sheet in, or maybe we're talking about a term sheet. to lead the round before you guys ultimately sold. Uh, and so there were alternative paths, I think, to keep going as well.
But you made the decision to sell the Autodesk. What, what, what did you see at that moment in time that sort of led to this? Conclusion for you.
Tracy: um, so it's important to understand that that deal and that conversation with Autodesk lasted about 10 months. So for 10 months, it was this. Cording and evaluating and several term sheets in place that weren't right for us. I think by the time we got the term sheet that I signed, we ran the math and we would have had to execute flawlessly for the next three years for us to be at the same place.
And in the end, I didn't have confidence and maybe courage in my ability to lead the company to, to execute flawlessly for the next three years. And it's also why we went out to fundraise a series C at that time, which we, we didn't end up taking. Um, it's so strange to go through a fundraising cycle, trying to lead the team and grow the company and trying to entertain an MNA.
Because we're taking our hearts and our minds and we're splitting it into three very different directions. And yet we have to maintain that these are totally good possibilities for us and you're just trying to figure out which one is the best outcome. And, um, the sell to Autodesk was the best outcome at that point in time for us.
Logan: Do you look back now? Uh, Procore is a 10 billion ish business. Um, do you look back and wish you were still in construction in the plane grid? You had made a different decision. Are you very happy with the outcome and how it landed?
Tracy: The outcome was very meaningful for everyone involved in PlanGrid, our investors, the founders, our employees, and everyone's families. Um, but yeah, a part of me wishes that I was still running PlanGrid today. It was a beautiful place, a beautiful company, and a beautiful product. And it's probably one of the reasons why I decided to start another company.
You have to understand that I retired from Autodesk after being there for a year. Um, you know, after the exhibition, you join the choirs and you help with whatever you, they need help with. And for me, it was integrating Plangren into Autodesk construction. I retired March 2020. I thought I was going to take a long trip with my family.
Our first vacation as a family and we went into a worldwide shelter in place and lockdown and what that gave us was a lot of time and I'm married to my co founder. It gave Ralph and I a lot of time to dissect every mistake we had ever made. What could we have done right, better? What could, what did we do right?
What would we do better next time? And we also just talked through a lot of the problems that annoyed us in the world. And TigerEye is the product that we really feel strongly would have been the difference between us having to sell. To audit us and us still leading the company today.
Logan: Not just any vacation. By the way, you were actually going to go on a cruise. Has
Tracy: yeah, yeah. And thank God we didn't get on that.
Logan: that cruise ever happened since then?
Tracy: no, it hasn't. I'm actually a little bit scared because if you recall in 2020. People were stuck on their cruise ship, dying of COVID.
Logan: Out in the bay, like out,
Tracy: Just right there.
Logan: away. Yeah. You touched on this, but integrating the startup into another company. I had heard you say that it was, uh, like jumping into freezing cold water. There's an initial shock to all of the system. I guess, um, any advice to founders as we sort of zoom out both in going down the acquisition path, as well as reflecting on the plan grid journey.
Yeah. If someone's thinking about selling, is there anything that you would pass along to them that you've learned over the course of the last four, five years?
Tracy: Yeah. So for, for, um, companies that are thinking about selling, it's really important to understand that companies are bought, they're not sold. If you want the deal more than your acquirers, it's not going to happen. There's a certain amount of, you know, you're the cool kid. Like. You can come to me to buy my company, right?
And what, what makes the deal attractive is a growing business with good technology, a good team and real revenue. That is, those are the, the, the downs that matter. Those are the, the substance that matters. I think for startups who are just burnt out and wanting to, you know, leave all their responsibility to someone else.
It's just not an attractive deal for an acquirer. But it's certainly possible. I think, you know, some people work with bankers. That's not a route we went down. Um, it's not a route that I would recommend. Um, some people go through a lot of corp dev and BD conversations and that just seems like a big waste of time to me.
Um, but it happens. It's just not the route we took.
Logan: You guys ultimately, the board wanted you to talk to other people and ultimately you decided, uh, that wasn't the right course for, for you all. What, uh, and you mentioned no bankers. I'm sure bankers would have wanted you to talk to people to maximize. Yeah. The price that you could get potentially, what, why did you elect to do not involve a banker and not talk to other people?
Tracy: I think I put myself in Oracle and SAP's leadership's head and it just, the deal just didn't make sense. And so if I couldn't see it from their point of view, why would I go through a whole emotional roadshow and create more work for myself? It didn't make sense. And that's what, you know, that's what I explained to the board.
They didn't agree with it, but they were also okay with it. Because at the end of the day, I'm the one who has to have these conversations. And if a founder is so unwilling, I mean, these aren't going to be good conversations,
Logan: Yeah. Yeah.
Logan: So I guess this is a nice transition to uh, tiger. I can you describe now that we're recording this before, but we've, we've alluded to it. Uh, what does Tiger? I actually do.
Tracy: Tigray is a business simulation engine that helps companies predict their future so that they can make strategic decisions faster and better.
Logan: So what does that mean in practice? Can you give me an example?
Tracy: So we sit between CRM and ERP. We understand every change in the business over time. We understand. Rep behavior, account behavior, customer behavior, and we use AI and advanced statistics on top of that to help a company predict its future.
What that translates to is the ability to create sales scenario plans. In minutes, not weeks or months. We also use a lot of math and advanced statistics and AI to show users how changes in their territory plans, their capacity models, their hiring schedules and plans. Their quota, quota plans will impact growth.
Logan: And so are you selling into a sales buyer? For the most part. Got it. And the existing players in this space, you touched on like it's uh, we alluded to it earlier,
Tracy: Yeah, we, we touch, we touch a lot of folks, um, because if you think about CRM and ERP, there's like thousands of companies here,
Logan: There's a lot of forecasting and planning
Tracy: yeah, yeah, yeah. So I think the closest product that overlaps with our platform and our suite is Anaplan. Um, we understand historicals.
Logan: historicals,
Tracy: We understand present day business, and we have a strong opinion about the future
Logan: a strong opinion about the future of this. For Laser Foot Ops team, we sometimes
Tracy: We're laser focused on the RevOps team. We, we sometimes pitch ourselves as co pilot for RevOps so that they can free up their time instead of manually munging numbers on a spreadsheet.
They can actually think strategically for the business and advise. The sales leaders and sweet, sweet on initiatives they can take on
Logan: Mid market enterprise or where, what's the, the
Tracy: upper mid market
Logan: upper mid market enterprise and what you said that this would have led to a different outcome for you, uh, at plan grid. Potentially you wanted to solve the problem that you had lived. What, what, what did you see in the problem set that you wanted to solve?
Tracy: So this time of year, it's, it's March and I mean, we would be barely done with our planning cycle because it was such a beast of the process. It would, would probably start around. Q4, maybe October, November, and maybe it wasn't like five people's full time job, but it would require a lot of mind space for half a dozen people on the, in the company and starting the whole leadership team.
And that process would sort of trickle through Q1 and we would barely get comp plans out because that's how much work it was to plan on a spreadsheet. Now there's a whole, so many products out there that are essentially spreadsheets on steroids. We evaluated many of them. Um, but as my VP of finance at Plangrid said, it's like, Tracy, I just don't think we should spend money on this because I'm an expert in Microsoft Excel.
Why would I spend time and waste my time on learning another spreadsheet product? And it was shocking to me by the time I left Plangrid, we were, we were spending over 100 million a year to achieve our growth. And we were planning all of that on a spreadsheet. And by the way, if we had an analyst leave, forget about it.
It's like, no one knew how to work that spreadsheet. And for Ralph and I, it's so obvious that. AI can help here in that a simulator that's used in other industries can actually be used by businesses to help predict the future. And it can help with certainly forecasting, but that's short term. It's the planning process that we want to help out with because it was so costly for us to create.
And you, you sit on boards, a high, low, medium plan. And we'd sort of look at the board. It's like, can you sign off on this medium plan that took us like three months to put together. With TigerEye, it's a few clicks of a button. In a minute, you can generate an entire plan. So the idea is you can test drive.
In construction, there's this term called measure twice, cut once. And there's no equivalent to that in business. Um, you have QAQC in software. You have QAQC in manufacturing. You test it out before you give it to the end user. Why are we spending three months generating this plan That we know has human errors on it that only one person can run on their Windows machine because we're, you know, a Mac house.
And then we're asking the entire team to execute on this. And as time passes. You know the plan is outdated, but we don't ever update the plan unless we really seriously don't think we're going to hit it and we're going to ask the board for a replan to lower the revenue target.
Logan: It's super interesting. It's a problem that all companies, uh,
Tracy: it's, we believe it's one of the most important decisions of the leadership team and there just isn't any tools to have helped us think deeply about the plan we were putting in front of the board to sign off on and the plan that we were asking our team to execute on every year. And it was so costly to us.
Um, I remember George who it's like He was one of our board directors and he's like, well,
Logan: who was the CEO of Twilio for a long time. Salesforce exists exact before
Tracy: as well. Yep. And he said, well, at Salesforce, we would plan every, every quarter. You guys need to plan every quarter. And I remember looking at it. I was like, you have no idea that is like impossible at our, our small company.
And it's because we didn't have the tools to do it.
TLBS 96 Tracy Young TigerEye (Final Edit YT): Hey guys, this is Rashad. I work with Logan on the show and I wanted to take a quick break to tell you about Red Point's other podcast, Unsupervised Learning. Unsupervised Learning is our AI podcast where we interview guests from companies like Perplexity, OpenAI, Adobe, and many others about the topical things that are happening in the very, very rapidly developing landscape of AI.
So if you're interested in going deeper, uh, check out the link in this description. For our YouTube channel, but also wherever you get your podcasts. So back to the show.
Logan: So one of the things I heard that you wanted to be purposeful about from Tiger eye, and it sounds like it was a reflection of your experience at playing. It was culture and it sounds like maybe you deviated a little bit from the Expressed values that you had at plan grid versus what was actually actionable eyes along the way.
Can you talk about that and how you're
Tracy: so just like all companies at Plangard, we had the five core values and maybe I could recite it to you again. And I think they were pretty good. You know, of course, all core values are like decent enough. Um, except we didn't live by it. So one of our core values was no assholes. And I think HR, I think HR was the one that complained about it.
So we ended up editing it to no jerks. And that's one of Plangrid's core values, except that there were a handful of jerks in the building. And since they were performing, I didn't fire them. And what that signaled to the team is like, Hey, if you just perform for the company, you perform for Tracy, you can get away with murder.
And oh yeah, by the way, the other four core values, those are all bullshit too. And so we were very intentional as we were drafting our core values for Tiger Eye. We actually had our core values in place before we picked the problem we would work on and build for. Um, that's how important it was to Ralph and I.
And really what we were optimizing for was a, just a healthy, productive culture where everyone can speak. courageously and know their teammates are gonna be backing them up. We have this other document that's called our commitments to each other and everyone signs it in blood, without blood, everyone signs it.
Logan: Proverbial
Tracy: And um, it clarifies our core values. So it's, there's no room for interpretation. It literally says I will walk it like I talk it. I will never speak destructively behind my teammates back. If I have a problem, I will walk up to them. And talk about it, because we're all professionals and adults, and we'll get through this problem together.
Logan: did no assholes, no jerks thing at at the plan grid when you start drifting from that. How? How does that manifest itself in the business? Once people start undermining or realizing that the values don't? Hold true consistently across the board. Did they manifest themselves in some
Tracy: Yeah, what you end up getting is these different camps, and at 500 people, there's probably like five different camps of different values, and you know, nothing's better than the other, they're just different. And there's certainly, you know, there was some combination of our five core values just split into five directions.
I feel like there's a Game of Thrones analogy here, but you know, like the different, the different houses, like I, yeah. Yeah. What that ends up creating is a us. Versus them mentality about our own internal team, you know, which is totally destructive. Um, because we are one team, except that not really. We're five different teams.
And now when things go bad, the first thing we do is point our fingers at each other.
Logan: I get the sense in listening to some of the, uh, earlier podcasts that you've done and some of your reflections on plan grid. That you, you maybe feel that you presented a version of yourself as CEO, um, and like maybe what you thought you should be as a CEO to the company, which wasn't always the most authentic version that you were feeling at all times.
And I think there is a, uh, there's an all hands that I had heard you talk about that you went on stage and finally just. Set all the problems that you had, uh, or all the problems that existed within the company and just sort of called it true in a very authentic way to, uh, to, to the employees there. Is that, is that fair?
Am I, am I reading too much into some of the past reflections or
Tracy: Yeah. I'm a construction engineer by training. Um, I didn't know anything about business yet. I was leading this company that was literally growing every single day. And what that meant was that I was in the biggest job I had done before every single day. And I suffered from serious imposter syndrome. I felt like I had tricked everyone into believing that I was a startup founder and CEO.
And I think part of the problem was representation. I didn't meet anyone who looked like me. I didn't know any CEOs who looked like me. I think now, hopefully times are changing, right? And, um, and, you know, it was so crazy. We were, I mean, we were growing. Our business was growing. There were problems, yes, but objectively, Plangard was doing well.
Any point in time of the 10 years I was leading it. And I remember confiding in Carol Bartz, who was one of our board directors,
Logan: CEO of Autodesk Yahoo before
Tracy: yeah, and she's like, what are you so worried about? This is before a board meeting. I was like, well, I'm, scared of being fired and she cackled. I'll, I'll never forget that laugh.
It's still in my head right now. She must have thrown her head back laughing at me and then saying, what is wrong with you, girl? You're not going to get fired. What are you talking about? But that, that felt real to me. Every board meeting. I couldn't tell you why. And So it was suffering from imposter syndrome.
I felt like I had tricked everyone into believing I could do this job. I felt like I was way over my skis. I didn't know what to do. And there was a version of a spounder and CEO in my head that didn't look like me. It looked like everyone else I saw. And I wanted to be that competent, confident CEO. And that's how I presented myself.
Well, the challenge is, I didn't have all the answers, I didn't know what I was doing, and so it came off inauthentic. It was probably coming off like I was a try hard or something. I actually don't know, I haven't talked to anyone. My, my, my team about that. But I remember there was one day where I was like, so overwhelmed with work.
I hadn't prepared for an all hands and it was time to go do the all hands with the team. So I went up and I just started talking about the problems I was working on and the risks I saw for the company. And, I mean, I remember the team completely responded to that. It was the best all hands I had ever given.
And it was like, whoa, I don't actually have to prepare for an all hands. This is great. In fact, at Tiger Eye, we have all hands every Monday and there's really no preparation. I just go in and I share with the team what's on my mind from the weekend. I share with them where I think the risks are, where I think we suck at, where I think we are doing great at.
And then, and then it's a full conversation. It's not just me monologuing at them. I want to hear from them. I want to hear the questions. In fact, if there's an All Hands where there's no questions, I really feel like something is wrong. Like seriously, does everyone know exactly what we're doing? Like it's, is it really going that well where we have no questions?
And, um, that really changed, I think, the way I lead and how I see myself as a leader. It
Logan: Was there a moment in time, I guess, that, that allowed you to shift to that? Perspective, or is it now that you've been successful? You realize you're no longer an imposter. You've sold a company for nearly a billion dollars. And so you can be more authentic to the organization. Or was it that all hands that you realized?
Hey, this is, you know, people
Tracy: was halfway through Planurin. So for another five years, I got to really feel more comfortable in my own skin. And certainly, second time around, just having experience now, like, I'm, I actually have experience as a CEO. That's really
Logan: Yes.
Tracy: And, um, certainly that, that gives me a little more confidence on certain things, right?
Like I know I can hire better people. I know how to interview now. I know how to look for the qualities that I, I, I think good team members possess. Um, I know how to take competition much more seriously than I did last time.
Logan: One of the things you outlined, uh, and you just alluded to this was recruiting people.
Logan: And I, I had heard you say there's three things that you do in the recruiting process. And I want to make sure I have them clear and understand how you think about this. But explaining what you want the company to do clearly, uh, what you are doing today and why it's a big problem.
And then understanding the market size and why it's going to be important. A big important opportunity for their career. Uh, I don't know if I have that exactly right. That's at least what I took down. But, uh, when recruiting people, how do you pitch, uh, and, and view these things as important?
Tracy: I think we all have a deep desire to work on something that is important, even if it's in our small little corner of the world. And to work on something that creates value for the world. And so whatever it is we're working on, we have to be able to communicate that to people that might or might not join us, especially for really ambitious people who wants to work on a project that doesn't matter.
Right. So that's number one. And then number two, I think when it comes to. Recruiting folks that will work nicely with the existing team and really, you know, who, who see our core values and, and raise their hand. It's like, actually, that's me too. That like, that's totally my vibe. Um, it's really communicating how it is to work.
How is it really to work? Like, let me paint a picture of how it is to work at our company. These are the projects that you will be working on. This is what we're trying to do together as a team. How does that sound to you? Does it sound exciting? Does it sound boring? And people will self select them out.
Logan: I had heard, uh, reference calls you view as super important and that you've said you've done up to 20 or something back channel and, and, uh, on sheet and all that, why do you view reference calls as so
Tracy: Oh, reference calls, especially for executives and especially for folks in sales and marketing. I feel like those profiles and it's, you know, the people who go into sales and marketing, they're pretty good at selling things and marketing themselves. And it's really hard to tell what their actual accomplishments are, especially when you look at the resume and they're like, Big company names.
It's like, it's hard to tell how much they actually contributed to the success of those companies. Did they just get lucky? And I find that the more people you talk to from their past starts painting a better picture of how it will be like to work with them. So I try to talk to people, of course, people that they reported to their bosses.
It's also nice if it's a manager to talk to people that reported to them and then certainly their peers as well. What you find in Silicon Valley is most people hate speaking poorly of, you know, their former colleagues and so you also have to get through all the extra, you know, conversations and Really digging in deep on the areas that you you think might be weaknesses or are imperfections of these person and sometimes it's okay It's like this type of personality might work with our team, but certainly being able to talk to 20 people It's gonna give you a really good picture because we're talking about 30 minute to hour long conversations with these people About a specific individual.
Logan: do you have tactics to get them to be honest about things that are? Weaknesses are shortcoming because people, to your point, don't want to bad mouth colleagues or former colleagues and reference calls.
Tracy: I think, I think either the person is, is, has that personality to be confrontational, or they, or they're, or speak honestly, or, or not. Um, I usually, if, if I feel like I'm having an inauthentic conversation with someone who's just going to give me a, bunch of fluff. I'll just ask them like, Hey, who else should I talk to?
Sometimes I'll find that they're actually giving me a name of someone who's more courageous than them. And
Logan: is, um, force ranking and throw out there. Like, is this a top? 50% person you've ever worked with, and when you put the puck on the ice a little bit, uh, and force them to think about, well, is in the better half of anyone that I've ever spoken to, if they're in a top 10%, they'll immediately give you a more perc no, no, no.
Top 10% easily. Right. If they, yeah, I mean definitely top 50%, then that probably means like, you know, they're, they're passing some platitudes off and you can't. really lie about that. Once you put it out there,
Tracy: hesitation will tell you a
Logan: it tells you a lot, right? And it, the implicit sign of all that is really interesting. Managing people is obviously like a difficult thing to do.
And, uh, Plangrid got to 500 people. Is that right? Uh, a hundred billion in recurring revenue. What, what did you learn about Um, managing people over that time that you would impart to someone that's early on the journey of, of leading and managing a team.
Tracy: Because I was a new manager, a new CEO. Well, by the time I left the company, I was like 10 years into it. So maybe not that new. Um, you start to notice patterns of the best managers and leaders that I, I got the privilege of working with. And usually the best managers have just been doing it longer than everyone.
That they've just been managing people and they've seen all the different flavors of personalities and ego and they just know what to do to deal and manage with that. Um, I just don't think it's something that's taught in school or that maybe it comes naturally for this small percentage of the world, but the best managers I had worked with.
that worked for PlanGrid had just been doing it longer than everyone else in the building.
Logan: And it's sheer, uh, said something, uh, I think in that exact seat that I think about that leadership. Can be innate, but management has to be learned. Uh, it's like, it's something you don't, you don't learn all these different social construct problems of, of all different personality types and feelings and all that stuff.
That's not like a, a natural thing that people have. I
Tracy: I'm a, I'm a terror. I'm a terrible manager. I mean, I'm either like, don't care about it. And I just like, can you just get it done? And then there's all a lot of trust if I have the right person in place, or I'm just micromanaging the hell out of it, which no one wants that for me.
Logan: I had heard you talk about the, uh, two by two matrix for product development where on the Y axis, I think it's level of effort and the X axis is impact to the, to the business. Um, and obviously,
Tracy: can flip it, of course.
Logan: Yeah. Yeah, it works both ways. Uh, but I think there's an important quadrant, no matter which way you go, which is high effort, high impact to the business.
Uh, the, I guess the best quadrant would be low effort, high impact to the business that you can just pick up easy wins. Um, how do you, how do you think about that matrix and making decisions and any tangible examples you can point to
Tracy: Yeah. And, um, it's low effort. And high impact for our customers is obviously the quadrant you want to focus on, but nothing's really sometimes you'll have the in between where it's like in between all four quadrants, which is hard to choose from. But obviously it's veered towards the high impact. Um, the way we think about product prioritization, which is I think is more art than science.
We try to look at it from several perspectives. So one, what is sales asking for? Two, what is the customer asking for? Three, what is the product team think we should be building? And then, um, now that I'm doing it the second time around, I make sure that the founders lens is also part of that decision making.
What do the founders want? Because the founders will always be keeping the vision in mind. Whereas everyone, like, sales might have a much shorter, short term horizon when they're looking out in the future, right? They're thinking about this quarter, they're thinking about maybe this year and their, their target.
Um, And when you overlay that on the same four quadrants, what you'll see is there's going to be a density of certain products and features that will make a lot of people happy. It's going to make sales happy, it's going to make the customers happy, and the founders also think it's like a cool feature.
Like, you want to build the stuff that everyone wants.
Logan: You had done a post on LinkedIn, uh, with sales advice for founders. And, uh, one of the things, uh, you, you touched on was that mid market was a no man's land. Um, and I think there were, uh, you got a lot of nice responses from people challenging that assumption. Why do you think that's a hard part to start a, uh, company around as a, as a startup?
Tracy: Because it's such a toss up of companies, it's a huge range. We define it as a hundred employees to a thousand employees. I mean, maybe people draw their lines a little differently, but let's say give or take another two hundred, right? Yeah. It's such a big range that a company with 100 people is completely different than a company with 1000 people.
So the mid market is full of small companies that recently graduated in, and it's full of companies that have been preparing themselves to become their enterprise counterpart for years, and they're gonna have a ton of red tape. And so it's it's important that we focus either in the enterprise Or SMB and know which lane you're serving.
And of course, we're going to sign up as many people in mid market as we can along the way, but there's just vastly different product priorities and decisions that you would make if you're serving SMB. Versus the enterprise suddenly enterprise features that don't matter for the end user really matters obviously at top of the market and then your ability to self serve a customer and help train them without ever having talking to them matters.
When you're serving lower market, because there's so many of them.
Logan: Yeah, the slope of the lines important in the middle. You can get caught with a very divergent slope of the lines. You can have companies that are 100 years old or 500 years old or whatever it is. You can also have companies that are four years old, five years old, that are well on their path of growing past.
You, it might be looking to the next solution. So
Tracy: Yeah, that's a good point. Logan. It's all about focus
Logan: One of the other things you said in that post was that, uh, in the early days, uh, of, of starting a company, you found it important to track, um, your customers in a spreadsheet, uh, and do it as long until your life sucks, I think was the, uh, the phrase you used.
Um, why do, why do you give that advice? Why do you think that's advantageous?
Tracy: because it's not just about turning our on a CRM system. It's about turning on a CRM system and then hiring administrators to administer that software solution. And unless you have the extra dollars and are ready to do that, it's just much easier to type it all into a spreadsheet, but it obviously doesn't scale.
And so. Yeah, I actually really believe in that advice. I don't know where you read that. Thank you. I'm so flattered you read so much of the content I've written. Um, yeah, don't, don't turn on CRM until your life sucks so bad. Same with ERP. Don't, don't turn any of that on until your life sucks so bad that you don't mind it sucking a little more.
Logan: And the point is that the process around. It should be thoughtful as well. And so it's I originally read it as the customer intimacy of knowing it inside and out, but it sounds like it's there's other considerations with it. And so you should make sure
Tracy: of deploying those software solutions is so high, both from a cost perspective and a time perspective. And more likely than not, you're going to set it up in a way that just doesn't, Work for your business because your business is evolving. Hopefully it's growing, it's evolving, it's changing. And what you've set up is probably not going to work for the next two years.
So now you've got to rejigger it. And that requires a lot of administrators to make it happen, to build in custom fields. I mean, this is the power of. The CRM systems and ERP systems is you can customize it, but you also have to be deeply confident in your sales process for you to customize it in a way that's going to help scale with your company.
And for most startups. They just have no idea, they're just, they're still trying to find product market fit. Or they're just trying not to drown with the amount of business that's coming their way and trying to iterate on their product that all of this is just extra noise. I don't think founders have the um, just the space to take on with everything going on.
Logan: it seems like no leader has ever regretted managing someone out too early. It seems like a universal truth. Uh, and I, I think, um, you, you, you agree with that, uh, sentiment. It sounds like something that was part of the reflections of, of playing grid as well. Um, how would you. How have you found a way of putting this in practice when, when something feels like it's not working out?
Do you, do you act on it right away when you're starting to get that sense or how has that evolved in your understanding of operating and leading?
Tracy: It's really painful to fire people. It's very emotional. There's probably a ton of guilt involved because you weren't the right leader to help this person grow, or you've hired the wrong person, and they've been at the company to make things a little worse. Um, If it's black and white, this person just can't do their job.
That's easy, right? It's always like between the spectrum that that is hard that they're contributing, but it's not enough or they're contributing, but it's the wrong cultural fit. Um, or they've been doing a great job. And this is one of the most heartbreaking parts about being a founder and a leader is the people who you've been to war with for the last two years might not be the right people to take.
With you for the next two years, right? And you have to make the hard decision. And I think it's just really important to remember that this hard decision is happening for the best of everyone. It's the right decision for the rest of the team, for your customers. It's also the right person, a decision for the person that's getting fired.
And the best we can do is to. Be as compassionate and generous as we can when we separate teammates and I think in life as well.
Logan: What have you learned about that, that conversation? I'm sure you've had to let a lot of people go and it's, it's, I'm sure varying range of emotional, but probably not easy no matter
Tracy: What have I learned? I think what I've learned is that it feels a little less bad when it's not a surprise to that person That everyone deserves a chance, um, but if it's not working, it's not working, and it's actually your job to fix this mistake. And it's better for the employees so that they can be at a place where they are contributing.
Um, and so when it comes to not surprising them, the conversation needs to go as such. It's, these are the expectations of the job, you are not meeting the expectations. And if this doesn't resolve itself, or if this doesn't change in some certain time period, we have to talk about parting ways.
Logan: Surprised
Tracy: you'll find is that some folks will immediately check out, because they're probably interviewing at other places, and it could be a combination of They have lost trust in you. They don't believe in your leadership. They don't believe in the company, and they just want to go somewhere else. Great. Or they don't believe in themselves.
That they don't actually think they can meet the expectations that you've set in place. And so they're self selecting out. And you'll sometimes find, I'd say only 10 percent of the case, but it does happen, you'll just see a person wake up one day and just completely turn it around. That actually, I don't know, something was going on in their lives and This is a job that they actually want to do, and they're going to do what they can to show you that they're going to meet your expectations and they deserve to be here.
Logan: you outlined, uh, a few things that the worst executives do in the list you gave was use the term I frequently. So I did something that we did something. Uh, you, you hate having one on ones with these people. It's generally a sign that, that the leadership's not working or the relationship isn't. They blame their peers and they also complain, I guess.
I assume that's from lived experience in all these cases, but do you immediately, if someone's using I instead of Uh, do you immediately call it out and tell him like, Hey, we don't do that here. Or does it, I guess some of these things feel like they could be very important. Uh, you're not giving credit to the other people on your team or maybe just a stylistic thing.
And so how do you think about that? That
Tracy: I usually just file it away. I mean, it's so subtle if someone's using the word I versus we, of course I'm not going to yell at them. I
Logan: I pick up on it all the time.
Tracy: it's more something I just file away. It's like, oh, that's interesting. Let's see how this works. How much this happens and maybe it's just an yeah, maybe this just isn't passing and they just use the wrong pronoun what's hard is because we've been so strategic and intentional about everyone we've been recruiting into the company that I just And we're young, right?
We're a young company, so we just haven't had these problems. As you're, as you're, as you're telling me these things, I guess in an interview, I, I, or I've written it, um, I'm actually getting, like, PTSD. It's just like, oh
Logan: remembering all this
Tracy: yeah, yeah, yeah, and it's just, I just haven't had that experience in a long time.
Logan: Well, I guess if you're self
Tracy: selective. But let's, let's say, okay, so if I hired the wrong executive, and they're showing all the signals that you just, um, reminded me of, yeah, it would be a conversation that it's not working out. I think the best thing to do is just to part ways.
Logan: I want to back up a little bit to the flangrid journey. So, so you were, uh, You were first in your family born in the U. S., right? Parents were immigrants from the Vietnam War and, uh, and came over here. And then ultimately you ended up majoring in construction engineering in college. And so that you went and, uh, I had heard you say at one point you were smoking cigarettes and chewing tobacco on the, on the front lines of, uh, construction jobs actually out in the fields.
What was the path from there to? Starting a company,
Tracy: Man, this is like over a decade ago. Let me, let me jog my memory here.
Tracy: Um, my co founder, PlanGrid's co founder, Ryan, my good friend, um, he stood in line for hours and he purchased first generation iPad and he was so excited to show me. So he showed it to me and we looked at it and we're like, we should, we're both construction engineers, we've gone through the same program.
And we looked at it, and it was this beautiful device. And we thought, hey, we should use this for work. We should put our blueprints on
Logan: and you guys were working together at the time?
Tracy: working at different companies. I was working for Rudolph and Slenton, general contractors, and he was working for, um, Gilbane.
And we tried to load one sheet of blueprint, which is nothing, because on the project I was on, there was like 5, 000 sheets just for the initial set.
Logan: Uh,
Tracy: Uh, anyways, we tried to load this one blueprint onto the iPad, and this box comes up, and it says, out of memory. And Ryan's like
Logan: aha moment, it's
Tracy: this, this aha moment. He's like, I, we should build it.
And I was like, yeah, it's a good idea, but we're not software engineers. And he's like, we'll just convince our friends to build it with us. And that's exactly what we
Logan: it with us, and that's exactly what we did. Well,
Tracy: Oh, Ryan, Ryan's such an entrepreneur, so we went to university together, and I met him when I was 18. I feel like he's been pitching me startup ideas since I was 18, and we finally started a company when I was, uh, 25.
Logan: I was 25.
Tracy: Cat roulette, I think, was, uh, gosh, there's so many crazy good ideas that Ryan had. Cat roulette was, we were going to have cameras on cats that we would save from the pound.
And you would play roulette and it would give you, you'd pay us, you'd play roulette, you'd get a cute cam on a cat and then you could pay us more and you could feed the cat treats.
Logan: So, so you didn't decide to go down that that path, but at the time you were, you were dating a, uh, a, uh, who now your,
Tracy: Ralph was, yeah, Ralph was an engineer.
Logan: he was an engineer. And so you guys are brainstorming these ideas. You and Ryan are, and you're sharing calendars maybe. And he saw, he's like, what, what is this you're doing with Ryan, uh,
Tracy: Ralph and I were at this point of our relationship where we're going steady. We share our Google calendars with each other.
So we know where we are at any given time. And he says, Hey, I've noticed that you meet with Ryan every Thursday and the subject of the calendar invites called peanuts. Why are you meeting with Ryan? I was like, that's really funny you should point this out because, um, we are working on a startup and we're looking for a technical co founder.
He was a rendering engineer at Pixar animations at the time. So he had like the perfect background to build this company with
Logan: how to cross your mind before he.
Tracy: Yeah, it did, but I really liked this guy. So I didn't want to complicate it with a relationship and a startup, which we ended up doing, but it does work because we have two companies and three kids.
Anyways, I tell Ralph this, the project that we were working on. He's like, do you even know what I do for a living? I can build this. And I was like, that's great. Do you want to join us? And he says, yes, can I be CTO? That was the, he cared about his title and that was
Logan: So there's, there's, there's five of you living in a hacker house together, uh, in the South Bay, right? When you're applying to
Tracy: And Sunnyvale,
Logan: Sunnyvale and, uh, I guess if anyone's thinking about starting a business with a, uh, a significant other, any, any advice for them, it seems like you guys have done it pretty successfully
Tracy: my advice would be, don't do
Logan: Don't do it.
Tracy: Don't do it. It is, if you really have to, you know, it does work, but it takes, it takes a lot of work. We are now pros at working with each other and it's still hard. I think relationships are hard, marriage is hard, kids are hard, startup is hard, so you're just really like a combinatorial explosion of problems that
Logan: too. It's not a linear, uh, company. Yeah. Um, so can you talk about those early days of finding product market fit? So you guys have this idea. Uh, and like, how did you actually go about validating that?
It worked. Presumably you had relationships
Tracy: So it's 2011. We've written an iPad app that basically digitizes the construction record set. We go to a bunch of people we worked with in the field, our friends on the, on the job sites that we were a part of, and we ask them to use it, and they're like, great, I'll, I'll try it out. I don't have an iPad. No one had an iPad at that point, not for work.
So we, we did something that I actually also wouldn't advise, which is we maxed out our credit cards. We went to Apple stores, and at this time, Apple had limits. On the number of iPads you could purchase. So we went to like four different stores and we bought as many iPads as we can, which is just like four.
And, um, we just gave it to our users for like, here, you can borrow our iPad and here's plan grid. And we, we helped them learn the software, which was very easy to use. And at some point, our friends and our customers would say, I don't know what I was doing using paper. I don't know what I was doing before Plangrid.
And we just looked at them and was like, great, beta's over, will you pay us? And we converted much of them and actually started making real revenue.
Logan: and did the, that. That flywheel of, um, juicing the market in the early days, I guess, or like kind of laying the groundwork doing the things that aren't scalable. Uh, did that allow you to get to the point in time and build the product that met the market when ultimately iPads were more democratized out in the field?
Or
Tracy: It took a few years to get that, get there, but we, I mean, we basically had a program. We had something called the iPad mini deal that was only supposed to go on for one month, but it ended up being years that we had the iPad mini deal. And later on, it'd be like the Android tablet deal and the Windows tablet deal as well.
We actually helped ship over 10, 000 iPads into the field. It was friction, it was a barrier to, to construction workers using PlanGrid. They didn't have a tablet. And so that meant they couldn't use our thing. And so we decided to solve that problem for them by buying it for them. I mean, you know, the economics worked out for us.
It's basically like, hey, purchase two years of PlanGrid. It was like 2, 000 bucks. And we'll throw in an iPad mini that will run our software beautifully. And that was a very popular skew. PlanGrid. com People didn't have to think about it, and it just shipped out of San Francisco's, um, Apple store.
Logan: you guys applied to go to, uh, to YC in the early? How'd you find your way to YC?
Tracy: Oh, my co founders are a bunch of nerds, and they were big readers of Hacker News. They tried to get me to read it, and it's like, this is just not my, just none of this calls to me.
Logan: Yeah, but you guys got in
Tracy: Um, they, there was a, a request for startups that the YC Partners had written, and one of them was, The iPad and mobile tablets are coming on the market and we think it's going to be valuable for specific industries that we're not even thinking about.
And I remember reading it and it was like, Oh, that's us. Because before that I refused to fill out the application. My co founders, a couple of my co founders wanted to, to go through YC, but I didn't think, I didn't think it was for us. And so until we saw the request for startups. And a request for startups that was clearly that our solution satisfied and I was like, all right, I'm going to fill out the application.
Logan: you guys got in.
Tracy: And then we got it.
Logan: Now you're living in Sunnyvale. There's five, five of you at this point and you guys have a prototype. You're going through YC. Is that, is that the, the, um, did you have customers in the early days of going into YC?
Tracy: Yes, we did.
Logan: Some friends and yeah. In the industry.
Logan: Um, and then, I mean, this is something that I, Can't even imagine, but one of your co founders got diagnosed with cancer at that point in time.
And so he ultimately went through a bunch of chemotherapy one round and then decided he didn't want to go through it again. Is that right?
Tracy: point. Yeah. He chose not to. It was, um, just, he just didn't want to put his body through that. He wanted to be happy in his last days. So it was crazy. We were trying to launch our startup. We did, you know, it's early, early stages of plan grid. And we had hospice care coming to our hacker house. I mean, I think back at it, it's like, I can't believe that happened, but it did.
And then he passes. And I think, you know, we were, we were just dealing with the death of our really good friend and co founder and chief mad scientist. And we didn't know what to do. So we just poured everything into the company. For me, it was because it was my way of feeling closer to him. And I think for the hackers on the team.
They must have been looking at Antoine's code every day and it was their way of feeling closer to him and I wanted to make the company successful in memory of my co founder.
Logan: Did you think about not going forward or was it
Tracy: You know, that wasn't an option in my mind. It was the, I really wanted to do it and I, and I think in hindsight I wanted to do it for Antoine because it was the last thing he worked on.
Logan: he was coding all the way up until the very end. And he gave you some really, uh, touching advice as well. Um, if you'd be comfortable
Tracy: Yeah, yeah, yeah. Let's see.
Um, something I think about every day. He says life is short. Take care of Ralphie. I've since revised it to take care of the ones you love. Don't be afraid to try new things and never do anything that makes you unhappy. And it was his gift to me before he left.
Logan: profound, profound advice,
Tracy: Yeah, someone, someone on his deathbed who wanted more time and wanted to make sure that he got his last thoughts to a friend.
Logan: Yeah, it's pretty, pretty powerful. And obviously I can't even imagine going through that, um, that experience.
Tracy: It's not, it wasn't unique to us though. I mean, I think we're all, we're all either dealing with it or will deal with it. Sickness, aging. Death. You learn this when the team grows to a size where it feels like bad stuff is happening on a weekly basis. There's just enough people and then their relationships with their family and friends, like all kinds of crazy things were happening all the time and we just have to be as generous as we can to our teammates when they have a partner who is dying of cancer or a child in the hospital because they're really, really sick.
Or they themselves have been in a car accident and they need to recover. Like life continues, even though we were trying to do something really hard, like starting a startup.
Logan: Can you draw me the through line from that hacker house to 5 million in ARR and raising a series a from Sequoia? What was, was it? Did the market just catch up to where, where you were and things were coming inbound?
Tracy: We moved out of the hacker house. Um, we had a small office in Hayes Valley, just a thousand square feet. We crammed like 15 people in there. Um, we were working around the clock, but we were happy and we just kept selling PlanGrid. There's a natural virality in construction. Where construction folks want to show off their new shiny tool to their peers in the field, like, hey, look at my new tool.
And Plangard was such a nice thing that they could show off to their friends who weren't using it. Like, let me, why are you using those blueprints? Let me show you what you can do with an iPad. And so we would get phone calls, there was so much inbound for our product, inbound demand. We would just get, it's like, hey, um, I just saw this on the job site, can you come and demo it to us also?
And we were just doing these demos and it was so easy to demo Plangard because it was so simple of a product. It would take us 10 minutes to do a demo remotely and go to meeting in those years. And we were just, and we were probably underpriced. I think the street price for Plangar at that time was like 200 bucks.
So no one would blink an eye at a foreman swiping 200 bucks on their credit card or 500 bucks for the higher tier. And, um, and then time just passes. And I think that's true. And enterprise software is just like. You just survive long enough and you just keep iterating and you keep talking to users, the company is going to get bigger.
You're going to sell more if you're just not completely messing up.
Logan: How do you think about that of, um, waiting for the, the market to come to you? And I guess this maybe dovetails into tiger eye as well, but there's, it feels like plan grid maybe was on a path of inevitability that this was going to happen in construction. And if it wasn't playing grid, it might be pro core, it might be someone else versus some other spaces.
It might not be inevitable. We haven't had a new ERP in a while. I think we can go back to that suite and whatever 99 or maybe intact
Tracy: think AI will change that.
Logan: Maybe so. But how do you think about like the inevitability of a market versus, you know, trying to will yourself into a market?
Tracy: having worked for a public company, I just think even the best companies and the winners, time passes and leadership changes and then a bunch of mediocre people stay there and they just slow down to a halt. No decisions are made because everyone's trying to protect 1 of revenue and trying to, you know, it's, I think it's very limiting to see a company have to talk to Wall Street and analysts every three months.
And that, you know, there's the CEO has to do a public earnings call. And what that means is there are decisions that need to happen because the world changes, the market changes, competition changes. Um, and as a company, we need to adapt with the world. Well, it's really, really hard when. The leader of a company is only interested in how they appear to analysts on an early earnings call every three months.
It limits decision making because you don't want drastic changes because you don't want to tell Wall Street about it. Um, and I think that just leaves a lot of room for startups to come and compete with them because they can make decisions, they can run faster, they can build faster. It's easier for them to adopt new technology.
They get what I think Peter Thiel calls last mover advantage and time passes. And I think the best companies, they just end up being mediocre.
Logan: In Raising Your Series A, Doug Leoni showed up at PlanGrid's office three straight days. Uh, what was that process like? Did you guys realize you had captured lightning in a bottle to some extent? Um, and, uh,
Tracy: I was so scared cause I'd heard all these, um, horror stories about deals falling through, um, from my founder friends. And so I really didn't want to mess up our Series A, so we had this incredibly profitable business with no sales folks, um, clear product market fit, which I think is interesting to any Series A investor, disrupting an entire industry for the first time.
I, I shouldn't have signed a term sheet so fast. Three days is crazy, like going on the road, showing up on Sand Hill Road, and then three days later getting several term sheets. It's crazy. And I signed the one with the heart on it because I thought it signaled that they cared more. But I think I should have done more about just evaluating the partners that we worked with.
Yeah,
Logan: now other than don't sign based on the, uh, The emojis that are put on a, on a piece of paper. Although for Doug, I mean, yeah, I don't think he's a very emotive guy. So that's a,
Tracy: yeah, yeah. He was surprised. I told him a few years later that he did that. He was like, really? I did? And I was like,
Logan: doesn't sound like
Tracy: I have a picture of
Logan: Yeah. Yeah. Yeah. Other than take your time and be deliberate, was there any lessons
Tracy: spend time with the partner.
Logan: get to know them?
Tracy: Is this someone you want to work with? Cause it's going to be a, if you're, if you're lucky, it's gonna be a 10 year journey. If you're really, really lucky, it's going to be a 20 year journey or longer.
Logan: you were at Autodesk for a year. Was it your obligatory? You signed on for a year to kind of manage the integration.
Tracy: We were actually out shorter than our required 18 months. Um, uh, it was just good for everyone. And so, um, we had finished integration. We really pushed integration into Autodesk construction. New leadership bench was in place. Everyone's handcuffs were in place. They didn't need us there anymore.
Logan: Um, you tried being a VC for a bit,
Tracy: We did. It's a hard job.
Logan: both of you?
Tracy: We both worked for Y Combinator.
Logan: Oh, wow. Uh, what did you, uh, dislike about that job or what pulled you back into being a founder? I guess two separate
Tracy: I think not knowing if I was doing a good job or not was really unfulfilling to me. And I didn't think I was actually good at it. I think I, I looked at the YC partners and everyone just had such broad knowledge and such deep care for just new technology. And I just didn't care about, you know, other people's stuff.
Like, I don't care about fintech. I mean, I know, I understand it's important. I don't really care about crypto. Um, I only care about the problems that I've experienced and understand. It's why I built PlanGrid. It's why I decided to build TigerEye. And I think not being able to see tangible results because, you know, I'm sure you've made investments and you're on boards and it's like, you actually don't know if these are good investments for another 10 years probably.
And I'm just impatient. I think, um, I like building and, like, I know when I do a bad job, right, like in construction, in software, in tech, you can see it every single day, the progress, and that's really important to me as a builder.
Logan: The feedback loops are very long in venture and you can justify doing even having a podcast for whatever reason, uh, because it can be opaque. The inputs into Success can be opaque over a long time horizon. So
Tracy: Yeah, and I saw, I saw what I thought were successful VCs and I, it was clear to me I didn't have that.
Logan: you referenced this earlier, but both companies you've started, uh, were pain points that you uniquely felt. Do you think that's a key ingredient to being a founder? Is that something you
Tracy: I do. I think that there needs to be a domain expert on the team, and I really think someone on the founding team, and it's nice when the CEO is, is the domain expert in the problem that we're trying to solve. Everything falls into place. We know who to hire to help solve these problems. We know how to talk to users.
We know how to talk to investors. Because it's like, I feel this deep in my bones that this sucks. This sucks so bad, I've decided to spend My short life working on this problem.
Logan: I had heard you say that tiger eye was about active activism in some way for you in showing representation of female founders and CEOs in the in the B to B enterprise world as well. Um, can you speak specifically
Tracy: Yeah, I had the privilege to work for YC for a year.
Tracy: I got to meet crazy ambitious and talented founders every single day and I certainly met women Founders who were building really cool things in consumer and health tech But I did sit there wondering why one there were so few women and two why there was no women in enterprise Software when there's so much low hang fruit and so much problems businesses have that just aren't served.
Right. And I think as a mom, it's really, really important to me. To show my children that you can dream and you can work at being part of the change. And for me, it's just, you know, I can complain about not enough women starting companies, not enough women in leadership, not enough women getting funded, or I can just do it and just be one improvement to the stats.
Logan: You all have been focused on building remote from day one, which was probably an outgrowth to some extent of, uh, the circumstances around COVID when you, when you got going, but also it seems like a, uh, a purposeful thing that you guys believe in. Can you talk about how you, uh, landed there and what some of the things you do to make sure you can maintain the culture?
Sure. And the process and the documentation and all that stuff.
Tracy: Yeah, so there's tradeoffs to everything for sure. I got to have 40, 000 square foot of office space in Mission District, San Francisco for almost 10 years, less than that because we moved into that big office. So let's say like seven years. Um, I got to see the power of having everyone in the office and the culture that that can, um, bring.
And now we've been running TigerEye for two years remotely as a much smaller team, and everyone's experience, you know, the average age of PlanGrid when we started it must have been in the mid twenties, I'd say the average age of TigerEye's team is probably mid forties. So we're just more experienced, and many of us have worked together before.
Um, there's trade offs to everything, but net net, for us, the positives outweigh the negatives. Um, I'll give you a few examples. One, there are, we are a diverse team, we are all over the world, um, we are huge spectrum of like age and like, you know, our demographics are very different and there's just, there's a lot of moms and dads on the team who have childcare duties and our work schedule allows us to take care of the stuff we need to in our families and also take care of the stuff we need to build for the business.
So in practicality, how that works, we have flexible work hours. There's six hours each day where, because we're all in different time zones, there's six hours each day where we are working together. And then the last two or three hours, I don't care when they work. For me, my kids are up by 5. 30, one of them at least.
And so I might be answering emails from like 6 o'clock to 7 o'clock. And then for my team member, they might be programming at 1 a. m. when half the team's sleeping, right? As long as work gets done and we're all contributing to the progress of the company, I don't care when those flexible work hours happen.
Everyone knows when you have, when you're most awake and when you're most energetic to actually work on problems. And so go, go figure that out. But those six hours is like, those are our core hours. So that's one. Um, Two, everyone's really good at communicating, um, written communication because so much about business building is making sure that we're all pushing in the same direction and trying to build in the, in the most impactful and efficient way possible.
And so you can imagine if we are lost in translation and not understanding each other in different states and that's going to be a huge problem in actually making progress. And so everyone is excellent at communication in the company, and that's something we, we really look out for. See, this is the only way it works.
Well,
Logan: the, uh, it's allowed you to hire a more diverse, uh, workforce and have these flexible hours as well. There's some trade offs on documentation and all of that stuff as well. I assume it gives a broader aperture of people you can hire, uh, talent wise too. I assume if you're not beholden to like a local office as well.
What, what about on the, uh, The negative trade off or the things that I guess process documentation is one that you guys have been purposeful about. But have there been things other than that that you've tried to that you've had to correct having experienced a office
Tracy: no substitution for being able to see someone and look them in the eyes and like break bread and eat together. And so it's, it's powerful when you have an office and you're literally eating lunch together every day, but as a remote team, we don't get that. So what we do instead is.
We actually have off sites quite frequently. We meet each other at least once a month, maybe several times a month, and certainly there's certain hubs around the world, and we're a small team. We're less than 30 people, but there's a density in San Francisco Bay Area, so many of us are meeting often at WeWorks and just places just to get that experience because it is nice.
It's especially evident when we have our all team off sites where everyone comes back together like we did last month, and there's just It's just really nice. And it's just faster to solve problems together when we're all right there and just pull people and it's like, can you look at this? And so we have the remote version of that, of like a five minute phone call or pulling someone into zoom room
Logan: Do you think you could have done a remote startup, uh, if not for the experience? Like if you're a first time founder, do you think you could have done a
Tracy: 10 years ago, I didn't think it would be possible. It wasn't until COVID happened where it was like, whoa, actually this is a lot better.
Logan: And if you hadn't lived the experience of plan grid though, do you think if you were a first time founder today at 26 years old or whatever,
Tracy: it's possible. I don't think it would have been possible for me. It'd been, it'd been too hard. You know, it's, I'm, I'm a mom of three young children, as you know, and I can say that I wouldn't be able to found another company if our company wasn't remote. If I had to drive to an office and sit there for eight to ten hours a day. It'd be really, really hard to, to want to do that and live that life.
Logan: What pulled you out of, you tried the VC thing and then you got all the reflections that you had not going on a cruise ship and, um, and all of that, like going after the problem that you're going after now, what, what was it? That led you to this as like, Hey, I want this to be my next chapter. I assume you want to do this for a long, long time.
Right. Uh, and there's not going to be a third company in your, in your future. So what was it that appealed to you about the problem set and actually starting this problem, starting
Tracy: you say that because, um, a couple of folks we really wanted to recruit is on the team. I did look them in the eye. It's like, this is the last company. I'm not starting another company. So if you've ever thought about working with us again, this is it. This is the time to join Tiger Eye. Um, you know, it's, we are, we are busy bodies.
We like to work. We like to build things. And I didn't want to regret not building for this problem. It's so obvious to us that spreadsheets sucks. In the same way it was so obvious to us that paper sucked. And that we need to digitize the construction set. It's so obvious to us that spreadsheets and spreadsheets and steroids for that matter just doesn't work.
And that there's actually technology. To simulate that's much more accurate at predicting the future than someone can do trying to program into macros into cells. And so one, it's we really deeply believe the solution should exist. Why hasn't someone built it? So we want to do it. Two, we need a job. We like building things.
And then three, why not? It's really fun. It's really fun and hard to build companies. And we get to work with insanely talented people going after a vision that we set. And I think for most founders, you have to be a little bit like on the spectrum and a little bit crazy. And it's just a really nice way to be able to outlet that energy.
Like my children, my parents live with me, my, my children and my parents don't need my intensity of a CEO at our home life. Um, but it's welcomed in a startup life. It's like Tracy care about these things. All right, I'm going to care about it. Same thing with Ralph. And it's just a really nice place to be able to let all that out.
Logan: What's the advantage of keeping tiger eye in stealth for the first two years? Or how long?
Tracy: It's been two
Logan: Two years.
Tracy: mean, it was just the founders, the two of us, um, and, and I have a two year old. So we went on maternity and paternity leave during that time. What is the advantage of being in stealth for two years? Well, we can build a lot more product. We can test it out with a lot more beta customers and really feel confident about our, our launch.
Logan: Was there something about the copycat experience with playing grid that led you down this, uh, this path?
Tracy: Yeah, I'm still shell shocked for my experience at Plangrid because it was, it was an incredible outcome, obviously, but in the end, there is no Plangrid today. There is, I mean, the product still kind of exists integrated to other solutions, but PlanGrid doesn't exist today, not even as a product name. It's, it's Build, it's Autodesk Build.
And, um, you can imagine as someone who's dedicated almost 10 years of her life to that product and it not existing, even though it's a great product, is kind of getting like sucker punched in the stomach, right? And so what is it about it? Um, we wanted to come out into the market strong
Logan: have customers live. And
Tracy: again, we were so seen as a point solution in the market and construction software.
I didn't want to do that again. I didn't want us to be pigeonholed by bleeding out features over the next 10 years. And I wanted to. Build what we feel is the complete product and go out to the market and it does connect a lot of problems together the past present day and future
Logan: one of the things I heard you say to founders is that they should keep their personal burn rate low in the early days. Um, why is that the case?
Tracy: Because you might not pay yourselves for a really long time in a startup That was true for Plangrid. That is true for TigerEye. Although circumstances are different, of course And so if you keep your burn rate low, then you can just last longer. At Plangarid, I remember we were all engineers, we're incredibly frugal.
And so we had 18 months of runway. We're like, all right, even if we don't make money, let's just build this for 18 months and then we'll see what happens. But you can imagine if we had more money in the bank and more savings, it could have been three years. And we could have built a lot more before we had to think about taking, selling part of our company, um, during a seed round or a series A.
Logan: There's a quote I heard you reference, uh, face reality as it is, not as it was or how you want it to be by Jack Welch from
Tracy: Jack Welch. Yeah.
Logan: Why do you like that quote?
Tracy: Oh, I love it. It's like my motto. Um, I think it's incredibly practical advice for any problems where, whether it's personal or in business. Thanks. that sometimes problems can feel so overwhelming and just such a big mountain and big obstacle that you might, you know, there's like the, the body reaction of like flight or fright or freezing and not doing anything.
Um, well, if you can just forget about the expectations and just look the problem in the eye and let, let yourself go where it hurts, then you can actually start solving the instead of spinning your wheels about. What should have happened or what should not have happened because what's in the past is like totally doesn't matter.
It's, you can still change the future if you action now. And I think in business and in product building, and I guess in life, it favors those who move. That movement is life. And it's certainly true in business as well.
Logan: I heard you say that you should raise or not and there is no in between. Uh,
Tracy: Oh yeah.
Logan: venture capitalists can be pretty compelling to sit down with and talk to about. Businesses at
Tracy: Either be in fundraising mode or not be in fundraising mode because it's too disruptive, it's too emotional. And you're also, again, living two different realities. And it's really hard to keep both realities in your mind. It's just takes energy and calories to make that happen. But if you're just in fundraising mode, then you can just park the business aside for a little bit, let the team run it and just focus on talking to as many people who might want to buy a piece of your business.
It's easier. It's like a little factory.
Logan: How do you tie that back with the three day process in the early days and getting to know someone? How did those two things put
Tracy: I mean, if I could do that round over again, I might've run a one month process and talked to as many people as I can. And. See who's the best partner for
Logan: Got it. So when you're in fundraising mode, focus on it, but spend the time. Don't don't. You don't need to get to know someone over months or years. You can, you You can keep it short in terms of process,
Tracy: Yeah, condense it, condense it. I think even a month is a quick round. Fundraising, it's just, it's just really emotional. You're taking all your hard work and your passion for the thing you've been building and you're putting it on a silver platter and you're almost begging people to please see the attraction and please buy a piece of it, right?
And you're getting diluted as part of it.
Logan: You have very specific opinions about how to structure board meetings. Uh, first, what do you view as the purpose of a, of a board meeting?
Tracy: The purpose of the board is to advise the company to its best possible outcome. And I've spent so many hours in board meetings, both as a CEO and as an independent board director of just hearing founders and executives brag about what their accomplishments are. And it's, it should never be used as like a showboating event.
And I've sat in so many hours where it was. And no one wants to see that. No one wants to sit in three hour board meetings where everyone's bragging about their work and not talking about real problems. And so, um, getting to do this a second time around, um, and it, we're, we're a young company where we can keep our board meetings short because not much is changing, not many decisions are needed to be made.
Um, our board meetings are one hour. I probably spend, Two hours thinking about the memo, I'll write them. And I don't spend like days creating a 90 page board deck like I used to. And then it's about running the company in a way where the team knows what we are doing. And then we're updating the board.
Whereas at PlanGrid, it was like, all right, let's spend a week putting this board deck together and our strategy together, present it to the board, get their feedback, and then announce it to the team. I don't know. It just ended up being, um, This kind of a lot of waste of time trying to update the board where now it's let's run the business.
Let's show them Let's just take screenshots of like the work we've been doing dumping in this letter. I write to the board. There's no preparation I'm really doing other than like piecing everything together until letter and then copy editing it and then handing it to the board and it's Like the expectation is just read the letter.
It's three to four pages And then the hour we're going to spend talking about the hard stuff. Like, these are the decisions we need to make. This is what I think is the right decision. Speak now or forever hold your peace because this is the next three months of our lives.
Logan: And so the hour is structured as you knock out all the legal stuff, right? You know, the approvals, the grants, all that. Then basically what's happened since the last board meeting, kind of a
Tracy: Mm hmm. An update.
Logan: update, and then zooming out on what's going on in the market and
Tracy: is, this is, this is what we think we should be doing given the market landscape. These are the updates to the market. We talk about the competitive landscape often at our board meetings. This is where we think we sit in the market. This is where we would like to be.
Logan: How do you, uh, think about work life balance now that
Tracy: Yeah. One of our core values at TigerEye is wholeheartedness. Um. It means that I expect the team to be wholehearted in whatever it is they are doing in their personal lives, if they're with their kids. I don't want to see them on Slack. I don't want to see emails from them. I don't want them thinking about work.
They are with their family. When they are at TigerEye, I don't want them thinking about their personal lives. These are the hours dedicated to TigerEye. I'm here with you too, and we're going to have our hearts completely here for this period of time. Thank you. And then after work, it's their own time.
Like, again, I don't want them answering messages from me or anyone. So that's how I think about work life balance. It's really, really hard to find balance. So then it's about making sure we're not splitting our hearts in multiple directions at any given time, whether personal or professionally. It's, it's about being present.
I'm here with you right now, Logan. I'm not thinking about my kids. I'm actually not thinking about work, even though we're talking about it. My team's got the work stuff. Um, in about 10 minutes, hopefully, whenever this interview
Logan: I, I, that was my last one. So I, uh, yeah. So now actually, uh, yeah, that was my, uh, my last question. So, uh, thank you for doing this. This is great.
Tracy: Yeah, thanks for the conversation.
Logan: Thank you for listening to this episode of The Logan Bartlett Show. If you enjoyed this conversation or other episodes like it, we really appreciate you sharing with other people you think might find this interesting. We're trying to grow the show.
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