EP 96: Tracy Young (CEO, TigerEye) Emerges from Stealth and Shares Every Mistake She Made As A First-Time CEO

This week, Tracy Young launched her second startup, TigerEye, from stealth mode. After selling PlanGrid to Autodesk for $875 million and working with YC for a couple of years, Tracy and her husband/co-founder decided to build the software they wished they’d had while building PlanGrid. In our conversation, Tracy unmasks her vision for TigerEye and shares everything she learned as a first time CEO that she’s bringing into her second company. (00:00) Intro (01:39) The Shift in Market Dynamics and PlanGrid's Response (07:07) The Importance of Addressing Multiple Stakeholders in Product Development (09:08) From PlanGrid to TigerEye: Tracy Young's New Venture (11:39) The Significance of Organizational Structure and Team Dynamics (15:03) The Evolution of Sales Strategy and Team Structure (17:28) The Decision to Sell PlanGrid and Its Aftermath (24:17) The Genesis of TigerEye and Its Mission (31:09) Cultivating a Purposeful Company Culture at TigerEye (39:29) Recruitment Strategies and the Value of Reference Calls (45:42) Product Development Insights and Market Focus (49:39) The Importance of Customer Tracking for Startups (49:57) The Challenges of Scaling with CRM and ERP Systems (51:55) Navigating the Tough Decisions of Firing Employees (57:08) The Journey from Construction Engineering to Tech Entrepreneurship (57:42) The Birth and Growth of PlanGrid (01:01:24) Navigating Personal and Professional Growth (01:05:50) The Emotional Journey of Losing a Co-Founder (01:17:34) From Stealth Mode to Market Impact with Tiger Eye (01:18:31) Embracing Remote Work and Building a Diverse Team (01:30:15) Reflections on Fundraising and Board Meetings (01:34:28) Finding Work-Life Balance in Startup Culture Executive Producer: Rashad Assir Producer: Leah Clapper Mixing and editing: Justin Hrabovsky Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA 🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1 Follow on Socials 📸 Instagram - https://www.instagram.com/theloganbartlettshow 📱 X - https://twitter.com/loganbartshow 🎬 Clips on TikTok - https://www.tiktok.com/@theloganbartlettshow About the Show Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode of The Logan Bartlett Show, we sit down with the people behind today’s most important startups and extract the tactics, lessons, and frameworks they’ve learned the hard way. Conversations span hiring to GTM, product, growth, fundraising and everything in between - collectively forming the ultimate playbook to make you a better CEO, investor or board member. Tap follow and enable notifications to stay ahead of the game.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:05Logan Bartlett?

  Welcome to the Logan Bartlett Show. In 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 Tiger Eye, 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

• 0:47Logan Bartlett?

  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. A really powerful conversation with Tracy that goes into what she's learned from her first go-round at PlanGrid that she's changing now that she has Tiger Eye. Tracy, thanks for doing this. There was a point in the journey of founding PlanGrid that 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?

• 1:25Speaker 01

  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. We were really good at building software for the end user, people who take showers at night, people who work hard days in hard hat, muddy boots, safety vests, safety glasses.

• 1:45Logan Bartlett?

  The actual construction workers.

• 1:47Speaker 01

  The actual construction workers. And...

• 1:51Speaker 01

  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, with a very broad platform and an enterprise-ready product. We had a product that was very much loved by the end user.

• 2:34Speaker 01

  If you were using PlanGrid in 2015, it's because you loved the product and you wanted to use it for your job. If you were using our competitor's 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 our product was not ready for that buyer. I mean, we didn't, we, it 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.

• 3:13Logan Bartlett?

  So did the market shift? Or did you find a different customer type? Did you go up market and the considerations changed?

• 3:20Speaker 01

  Oh, that's a good question. And 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 up market 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.

• 4:05Speaker 01

  And so we would get calls from CIOs saying, are you seriously selling?

• 4:14Speaker 01

  A thousand licenses licenses to us one at a time in the field. 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.

• 4:25Logan Bartlett?

  Hmm. So the the incumbents Procore, they had the the security and the role-based access and the permissioning and all that stuff that resonated with the buyer 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?

• 4:50Speaker 01

  Um, 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. Um, 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 in Red Hat.

• 5:15Logan Bartlett?

  Is there something you could have done sooner to catch that in retrospect? Or was it?

• 5:20Speaker 01

  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.

• 6:05Speaker 01

  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.

• 6:16Logan Bartlett?

  The advice that you often hear, and it's kind of a platitude, but it's like delight your your customer or delight your end user. And it's counterintuitive in some ways that if you had just focused on your end user, that that's what you did. And it actually led to the market shifting out from underneath you. 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 moved underneath you?

• 6:47Speaker 01

  Yeah, I think the kaizen and the, the 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.

• 7:03Logan Bartlett?

  So three different constituents in all that. Kaizen, continuous improvement, a Japanese phrase. Now it's one of your cultural tenets at Tiger Eye, right? So, um, yeah, it's interesting because those are three discrete 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 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. So.

• 7:32Speaker 01

  Yeah, what we have to understand is, um, there's multiple buyers in enterprise software. There's the end user. There's a person who trains. There's a person who actually physically finds where the budget is and pays for it.

• 7:47Logan Bartlett?

  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?

• 8:01Speaker 01

  Yeah, it's an endless 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. 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, whoa, 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. But knowing that I am going into a highly penetrated space

• 8:42Speaker 01

  in sort of, and I haven't talked about what Tiger Eye does, but 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. 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.

• 9:07Logan Bartlett?

  And so how do you think about shifting that discussion now? And maybe this is a good opportunity to, we'll dive into it in more in earnest, but what Tiger Eye is doing and shifting that conversation. So you're no longer battling an incumbent on a feature by feature, but instead helping.

• 9:23Speaker 01

  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.

• 9:38Logan Bartlett?

  And that's a kind of a nerdy in the details thing here, but 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

• 10:03Logan Bartlett?

  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?

• 10:16Speaker 01

  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 flat 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.

• 10:55Logan Bartlett?

  I want to stay on the PlanGrid story for a bit and then we'll transition to Tiger Eye. But one of the things I thought was really interesting and I've, as a board member, I've had these discussions more than once is the idealistic approach of org structures and mid-level management and no salespeople and all of that. It sounds like you're a converted, you've converted from that, from that past ways of thinking. But in the early days, you guys were pretty dogmatic about no mid-level management, flat org structure, no salespeople.

• 11:28Speaker 01

  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.

• 11:46Speaker 01

  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 Tiger Eye, 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. We wanted to be so creative about how we organized our team and we were less than 30 people. We would tell, we would brag about this. We like, 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.

• 12:29Speaker 01

  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 thirty 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 twenty twelve, twenty thirteen. 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, we're, will care about that stuff. And if you want to retain them, you have to care about it, too.

• 13:06Logan Bartlett?

  There's these two different mindsets, I think, within Silicon Valley. And one is that titles are cheap and that you can, you can give them away because they don't cost anything. Uh, the other one is titles are 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 going to 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.

• 13:42Speaker 01

  Yeah, it's like, it's really popular to have the title head of something.

• 13:46Logan Bartlett?

  Yeah, exactly.

• 13:47Speaker 01

  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.

• 14:05Logan Bartlett?

  Hmm.

• 14:06Speaker 01

  And so they're cheap in, in that side of the business. I think levels are really important for many reasons. Um, but yeah, um, I, I think it's important to be thoughtful about it. And as you hinted, it's because there's going to be emotional challenges that come up and you know, it's going to 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.

• 14:31Logan Bartlett?

  Was there a point in time on the sales journey, uh, that you converted to, to saying we need salespeople 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?

• 14:45Speaker 01

  We're really interesting in that we, in our last company, PlanGrid, we founded the company in twenty eleven. 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.

• 15:02Speaker 01

  And then our first quota caring salesperson came in the building January first two thousand fifteen.

• 15:11Logan Bartlett?

  Wow.

• 15:12Speaker 01

  So that's a long time to go without salespeople. We got to five million 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 because you've got product market fit.

• 15:27Logan Bartlett?

  Hmm.

• 15:28Speaker 01

  I think

• 15:30Speaker 01

  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 cash flow 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, third place luckily. And then just a lot of smaller companies just waiting to die a slow death.

• 16:04Logan Bartlett?

  Hmm.

• 16:05Speaker 01

  And that wasn't obvious to me until I think ten years into the company.

• 16:10Logan Bartlett?

  Hmm. Still, I mean, remarkable, just to say those numbers out loud, that you were got to five million in recurring revenue, cash flow positive with uh with no salespeople in place. I see why.

• 16:22Speaker 01

  We, we had, so to be clear, there was no quota caring salespeople. We didn't pay out commissions. But there are 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.

• 16:52Logan Bartlett?

  Got it, got it. Um, so. Playing great 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. That said, I realize it was incredibly difficult decision to sell. I think 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. And so, there were alternative paths, I think, to keep going as well. But you made the decision to sell Autodesk. What, what, what did you see at that moment in time that sort of led to this conclusion for you?

• 17:38Speaker 01

  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 courting and evaluating and several term sheets in place that weren't right for us. I think by the time we got their 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

• 18:22Speaker 01

  also why we went out to fundraise a Series C at that time, which we, we didn't end up taking.

• 18:33Speaker 01

  It's so strange to go through a fundraising cycle, trying to lead the team and grow the company and trying to entertain M&A 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

• 19:04Speaker 01

  The sell to Autodesk was the best outcome at that point in time for us.

• 19:08Logan Bartlett?

  Do you look back now, Procore is a $10 billion ish business. Do you look back and wish you were still in construction and that PlanGrid you had made a different decision? Are you very happy with the outcome and how it landed?

• 19:24Speaker 01

  The outcome was very meaningful for everyone involved in PlanGrid and their investors, the founders, our employees, and everyone's families. 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. Because you have to understand that I retired from Autodesk after being there for a year.

• 19:57Speaker 01

  And after the exhibition, you joined the choirs and you help with whatever they need help with. And for me, it was integrating PlanGrid into Autodesk's 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.

• 20:41Speaker 01

  And Tiger Eye is the product that we really feel strongly would have been the difference between us having to sell to Autodesk and us still leading the company today.

• 20:51Logan Bartlett?

  Not just any vacation, by the way. You were actually going to go on a cruise, is that right?

• 20:54Speaker 01

  Yeah, yeah, yeah, yeah. And thank God we didn't get on that.

• 20:58Logan Bartlett?

  Has that cruise ever happened since then?

• 20:59Speaker 01

  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.

• 21:07Logan Bartlett?

  Out in the bay, like not too far away, yeah. You touched on this, but integrating the startup into another company. I had heard you say that it was like jumping into freezing cold water. There's an initial shock to all of the system. I guess, any advice to founders as we sort of zoom out, both in going down the acquisition path as well as reflecting on the planned grid journey? 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?

• 21:38Speaker 01

  Yeah, so for 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 makes the deal attractive is a growing business with good technology, a good team and real revenue. That is, those are the nouns that matter. Those are the substance that matters. I think for startups who are just burnt out and wanting to,

• 22:22Speaker 01

  you know, leave all the 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. It's not a route that I would recommend. Some people go through a lot of corp dev and BD conversations, and that just seems like a big waste of time to me. But it happens. It's just not the route we took.

• 22:49Logan Bartlett?

  You guys ultimately, the board wanted you to talk to other people. And ultimately, you decided that wasn't the right course for you all. What, and you mentioned no bankers. I'm sure bankers would have wanted you to talk to people to maximize the price that you could get potentially. Why did you elect to do not involve a banker and not talk to other people?

• 23:10Speaker 01

  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, right?

• 23:42Logan Bartlett?

  Yeah, yeah, yeah. So I guess this is a nice transition to Tiger Eye. Can you describe now that we're recording this before, but we've alluded to it. What does Tiger Eye actually do?

• 23:55Speaker 01

  Tiger Eye is a business simulation engine that helps companies predict their future so that they can make strategic decisions faster and better.

• 24:04Logan Bartlett?

  So what does that mean in practice? Can you give me an example?

• 24:07Speaker 01

  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

• 24:52Speaker 01

  territory plans, their capacity models, their hiring schedules and plans, their quota plans will impact growth.

• 25:01Logan Bartlett?

  And so are you selling into a sales buyer for the most part?

• 25:05Speaker 01

  Yes.

• 25:06Logan Bartlett?

  Got it. And the existing players in this space, you touched on like it's, we alluded to it earlier.

• 25:12Speaker 01

  Yeah, we touched, we touch a lot of folks. Because if you think about CRM and ERP, there's like thousands of companies here.

• 25:19Logan Bartlett?

  There's a lot of forecasting and planning.

• 25:21Speaker 01

  Yeah, yeah, yeah, yeah. So I think.

• 25:25Speaker 01

  The closest product that overlaps with our platform and our suite is Anaplan.

• 25:31Logan Bartlett?

  Yep.

• 25:32Speaker 01

  We understand historicals, we understand present day business, and we have a strong opinion about the future business.

• 25:41Logan Bartlett?

  And for people that don't know, Anaplan was a $12 billion acquisition by Toma Bravo, a public company, very successful outcome. And now there's other people popping up, selling into FPNA and sort of doing the financial planning side of this as well. But it sounds like you're more focused on the the sales side.

• 25:59Speaker 01

  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 sway seat suite on initiatives they can take on.

• 26:18Logan Bartlett?

  I I assume targeting mid-market enterprise or where what's the the

• 26:24Speaker 01

  Upper mid-market enterprise.

• 26:25Logan Bartlett?

  Upper mid-market enterprise. And what you said that this would have led to a different outcome for you at PlanGrid 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?

• 26:39Speaker 01

  So this time of year, it's it's March. And I mean, we would be barely done with our planning cycle because of 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 certainly 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 and steroids. We evaluated many of them.

• 27:21Speaker 01

  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 and that a simulator that's used in other industries can actually be used by businesses to help predict the future.

• 28:05Speaker 01

  And it can help with certainly forecasting, but that's short term. It's the planning process that we want to help out with.

• 28:12Speaker 01

  Because it was so costly for us to create, and 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 Tiger Eye. 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. You have QA QC in software. You have QA QC in manufacturing. You test it out before you give it to the end user. Why are we spending three months generating this plan?

• 28:53Speaker 01

  That we know has human errors on it, that only one person can run on their Windows machine. Cause 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.

• 29:18Logan Bartlett?

  It's super interesting. It's a problem that all companies.

• 29:21Speaker 01

  It's, 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. I remember George Hu, it's like, he was one of our board directors and he's like.

• 29:45Logan Bartlett?

  George, who was the CEO of Twilio for a long time. Salesforce exists.

• 29:49Speaker 01

  Salesforce 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 and I was like, you have no idea that is like impossible at our, our small company. Yeah. And it's because we didn't have the tools to do it.

• 30:07Logan Bartlett?

  Hey, Logan, jumping in here, just with a brief request, if you're enjoying this episode, or you have a favorite episode, would love for you to share that with anyone that you think would benefit from it. Anyone that is trying to be a better founder, a better operator, a better board member, a better investor, would love for you to share any episode that you think makes sense with them. We're trying to get the word out, continue to share with people in the ecosystem. And so that would be really, really helpful. Now, back to our conversation. 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 PlanGrid was culture. And it sounds like maybe you deviated a little bit from the expressed values that you had at

• 30:49Logan Bartlett?

  PlanGrid versus what was actually actionableized along the way. Can you talk about that and how you're planning on?

• 30:54Speaker 01

  So just like all companies at PlanGrid, 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. 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, by the way, the other four core values, those are all bullshit,

• 31:35Speaker 01

  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. 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 going to be backing them up. We have this other document that's called our commitments to each other, and everyone signs it in blood.

• 32:15Speaker 01

  Without blood, everyone signs it.

• 32:17Logan Bartlett?

  Proverbialed.

• 32:18Speaker 01

  And 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.

• 32:42Logan Bartlett?

  Did the no assholes, no jerks thing at Plan Grid, when you start drifting from that, how, how does that manifest itself in the, 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 ways?

• 33:01Speaker 01

  Yeah, what you end up getting is these different camps. And at 500 people, there is probably like five different camps of different values. And 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. I'm sure. Like the different, the different houses.

• 33:21Logan Bartlett?

  Warring factions, yeah, yeah.

• 33:22Speaker 01

  Yeah. What that ends up creating is a us versus them mentality about our own internal team, you know, which is totally destructive.

• 33:38Speaker 01

  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.

• 33:47Logan Bartlett?

  I get the sense in listening to some of the 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. 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's a, there's an all hands that I had heard you talk about, that you went on stage and finally just said all the problems that you had, or all the problems that existed within the company and just sort of called it true. In a very authentic way to to the employees there is that is that fair?

• 34:30Logan Bartlett?

  Am I am I reading too much into some of the past reflections or?

• 34:34Speaker 01

  Yeah, I'm a construction engineer by training. 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 and I mean, it was so crazy. We were, I mean, we were growing. Our business was growing.

• 35:14Speaker 01

  There were problems, yes, but objectively Plangued was doing well. Any point in time of the 10 years I was leading it. And I remember confiding in Carol Bart, who was one of our board directors.

• 35:28Logan Bartlett?

  Former CEO of Autodesk Yahoo before that.

• 35:31Speaker 01

  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 I couldn't tell you why. And so I 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.

• 36:15Speaker 01

  And there was a version of a founder 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 tryhard or something. I actually don't know. I haven't talked to 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.

• 36:57Speaker 01

  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.

• 37:40Speaker 01

  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 that really changed, I think, the way I lead and how I see myself as a leader.

• 37:54Logan Bartlett?

  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,

• 38:17Speaker 01

  It was halfway through Plan G.

• 38:19Logan Bartlett?

  Yeah, got it.

• 38:20Speaker 01

  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 nice.

• 38:33Logan Bartlett?

  Yes.

• 38:34Speaker 01

  And 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. I know how to take competition much more seriously than I did last time.

• 38:52Logan Bartlett?

  One of the things you outlined, and you just alluded to this, was recruiting people. And 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, what you're 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. I don't know if I have that exactly right. That's at least what I took down. But when recruiting people, how do you pitch and view these things as important?

• 39:27Speaker 01

  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 see our core values and raise their hand, it's like, actually, that's me too. That like, that's totally my vibe.

• 40:09Speaker 01

  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.

• 40:28Logan Bartlett?

  I had heard reference calls you view as super important and that you've said you've done up to 20 or something back channel and on sheet and all that. Why do you view reference calls as so important?

• 40:41Speaker 01

  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

• 41:26Speaker 01

  to talk to people that reported to them, and then certainly their peers as well. What you'll find in Silicon Valley is most people hate speaking poorly of, you know, their former colleagues. And so you also have to just get through all the extra, you know, conversations and really digging in deep on the areas that you you think might be weaknesses or 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 is going to give you a really good picture. Because we're talking about 30 minute to hour long conversations with these people about a specific individual.

• 42:06Logan Bartlett?

  Do you have tactics to get them to be honest about things that are weaknesses or shortcoming? Because people, to your point, don't want to bad mouth colleagues or former colleagues in reference calls.

• 42:19Speaker 01

  No, I think I think either the person is is has that personality to be confrontational or they are there or speak honestly or not. I usually, 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?

• 42:36Logan Bartlett?

  Hmm.

• 42:37Speaker 01

  Sometimes I'll find that they're actually giving me a name of someone who's more courageous than them.

• 42:43Logan Bartlett?

  I found one of the things that that I'll do is 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, 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 percent. 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.

• 43:19Speaker 01

  And that hesitation will tell you a lot.

• 43:21Logan Bartlett?

  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 PlanGrid got to 500 people, is that right?

• 43:33Logan Bartlett?

  100 billion in recurring revenue. What, what did you learn about managing? People over that time that you would impart to someone that's early on the journey of, of leading and managing a team?

• 43:46Speaker 01

  Because I was a, 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.

• 43:55Speaker 01

  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.

• 44:18Speaker 01

  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.

• 44:33Logan Bartlett?

  Emmett Shear said something, I think in that exact seat, that I, I think about that leadership can be innate, but management has to be learned. 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.

• 44:54Speaker 01

  Yeah, I'm a terrible, 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 of I have the right person in place, or I'm just micromanaging the hell out of it, which no one wants that from me.

• 45:09Logan Bartlett?

  I had heard you talk about the 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. And obviously.

• 45:21Speaker 01

  Flip it, of course.

• 45:22Logan Bartlett?

  Yeah, it works both ways, but I think there's an important quadrant, no matter which way you go, which is high effort, high impact to the business. The, I guess the best quadrant would be low effort, high impact to the business that you can just pick up easy wins. How do you, how do you think about that matrix and making decisions and any tangible examples you can point to?

• 45:42Speaker 01

  Yeah, and 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 veer towards the high impact. 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 does the product team think we should be building? And then now that I'm doing it the second time around, I make sure that the founder's

• 46:25Speaker 01

  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.

• 46:46Speaker 01

  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.

• 47:04Logan Bartlett?

  You had done a post on LinkedIn with sales advice for founders and one of the things you touched on was that mid-market was a no man's land. And I think there were, you got a lot of nice responses from people challenging that assumption. Why do you think that's a hard part to start a company around as a, as a startup?

• 47:24Speaker 01

  Because it's such a toss up of companies. It's a huge range. We define it as 100 employees to 1,000 employees.

• 47:33Speaker 01

  I mean, maybe people draw their lines a little differently, but let's say, give or take another 200, right? It's such a big range, like a company with 100 people is completely different than a company with 1,000 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 going to 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.

• 48:14Speaker 01

  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.

• 48:41Logan Bartlett?

  Yeah, the slope of the line's 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, 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 and might be looking to the next solution. So focusing just in there can be difficult.

• 49:04Speaker 01

  Yeah, that's a good point, Logan. It's all about focus.

• 49:06Logan Bartlett?

  Yeah. One of the other things you said in that post was that in the early days of starting a company, you found it important to track your customers in a spreadsheet and do it as long until your life sucks, I think was the phrase you used. Why do, why do you give that advice? Why do you think that's advantageous?

• 49:24Speaker 01

  Because it's not just about turning 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. 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.

• 50:02Logan Bartlett?

  And the point is that the process around it, 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.

• 50:17Speaker 01

  The cost 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.

• 50:59Speaker 01

  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 that I don't think founders have the

• 51:19Speaker 01

  just the space to take on with everything going on.

• 51:22Logan Bartlett?

  Seems like no leader has ever regretted managing someone out too early. It seems like a universal truth. And I, I think you, you, you agree with that sentiment. It sounds like something that was part of the reflections of PlanGrid as well. How have 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?

• 51:56Speaker 01

  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.

• 52:14Speaker 01

  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. 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.

• 52:57Speaker 01

  It's also the right 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 with teammates, and I think in life as well.

• 53:11Logan Bartlett?

  What have you learned about that that conversation? I'm sure you've had to let a lot of people go.

• 53:15Speaker 01

  Yeah.

• 53:16Logan Bartlett?

  It's I'm sure varying range of emotional, but probably not easy, no matter what.

• 53:20Speaker 01

  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.

• 53:32Speaker 01

  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. And so when it comes to not surprising them, the conversation needs to go as such. It's these are the expectations of their job. You are not meeting the expectations. And if this doesn't resolve itself, or this doesn't change in some certain time period, we have to talk about parting ways.

• 54:03Logan Bartlett?

  And so doing that upfront so that they're not surprised.

• 54:06Speaker 01

  What 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% of the case, but it does happen. You'll just see a person wake ups 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 gonna do what they can to show you that they're going to meet your expectations and they deserve to be here.

• 54:49Logan Bartlett?

  You outlined a few things that the worst executives do in the list you gave was use the the term I frequently. So I did something, now we did something. 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 we? Do you immediately call it out and tell them like, hey, we don't do that here? Or does it? I guess some of these things feel like they could be very important. 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 when?

• 55:34Speaker 01

  I usually just file it away.

• 55:35Logan Bartlett?

  Yeah.

• 55:36Speaker 01

  I mean, it's so subtle if someone's using the word I versus we. Of course, I'm not gonna

• 55:40Logan Bartlett?

  Yeah.

• 55:41Speaker 01

  yell at them.

• 55:42Logan Bartlett?

  I pick up on it all the time.

• 55:44Speaker 01

  Yeah, it's it's more something I just file away. It's like, oh, that's interesting.

• 55:48Logan Bartlett?

  Yeah.

• 55:48Speaker 01

  See how how much this happens.

• 55:50Logan Bartlett?

  How that manifests itself.

• 55:51Speaker 01

  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, we're a very 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've written it. I'm actually getting like PTSD. Just like, oh, God.

• 56:17Logan Bartlett?

  Remembering all this stuff from?

• 56:18Speaker 01

  Yeah, yeah, yeah. And it's just, I just haven't had that experience in a long time.

• 56:21Logan Bartlett?

  Yeah. Well, I guess if you're self-selecting for

• 56:23Speaker 01

  Let's say, okay, so if I hired the wrong executive and they're showing all the signals that you just 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.

• 56:34Logan Bartlett?

  I want to back up a little bit to the PlanGrid journey. So you were you were first in your family born in the US, right? Parents were immigrants from the Vietnam War. And came over here. And then ultimately, you ended up majoring in construction engineering in college. And so then you went and I had heard you say at one point, you were smoking cigarettes and chewing tobacco on the on the front lines of construction jobs, actually out in the fields. What was the path from there to starting a company?

• 57:06Speaker 01

  Man, this is like over a decade ago. Let me jog my memory here. My co-founder, PlanGrid's co-founder, Ryan, my good friend.

• 57:16Speaker 01

  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'd gone through the same program. And we looked at it and there's this beautiful device. And we thought, hey, we should use this for work. We should put our blueprints on this.

• 57:37Logan Bartlett?

  And you guys were working together at the time?

• 57:39Speaker 01

  We were working at different companies. I was working for Rudolph and Sutton General Contractors and he was working for Gilbein. And we tried to load one sheet of blueprint, which is nothing because on the project I want was on, there was like 5,000 sheets just for the initial set. 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, 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 did.

• 58:15Logan Bartlett?

  I guess you guys were iterating on ideas for a little bit. I'd heard Cat Roulette was one of the

• 58:20Speaker 01

  Oh, Ryan, Ryan is 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 25.

• 58:34Logan Bartlett?

  What was the idea behind Cat Roulette?

• 58:36Speaker 01

  Cat Roulette, I think was, 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.

• 59:02Logan Bartlett?

  So you didn't decide to go down that path?

• 59:04Speaker 01

  No.

• 59:05Logan Bartlett?

  But at the time, you were you were dating a a who now now you're you're a husband.

• 59:12Speaker 01

  Ralph was yeah Ralph was an engineer.

• 59:13Logan Bartlett?

  He was an engineer and so you guys were brainstorming these ideas you and Ryan are and

• 59:18Speaker 01

  Yeah.

• 59:18Logan Bartlett?

  You're sharing calendars, maybe?

• 59:19Speaker 01

  Yeah, yeah, yeah, yeah.

• 59:20Logan Bartlett?

  And he saw, he's like, what what is this you're doing with Ryan?

• 59:23Speaker 01

  So 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 invite is 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 rendering engineer at Pixar Animations at the time. So he had like the perfect background to build this company with us.

• 1:00:00Logan Bartlett?

  Had it cross your mind before he?

• 1:00:02Speaker 01

  Yeah, it did, but I really liked this guy.

• 1:00:04Logan Bartlett?

  Yeah.

• 1:00:04Speaker 01

  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 he he cared about his title and that was it.

• 1:00:33Logan Bartlett?

  So there's there's there's five of you living in a hacker house together in the South Bay, right? When you're applying to Y Combs?

• 1:00:40Speaker 01

  Sunnyvale.

• 1:00:41Logan Bartlett?

  In Sunnyvale. And I guess if anyone's thinking about starting a business with a significant other, any any advice for them? It seems like you guys have done it pretty successfully so far.

• 1:00:51Speaker 01

  My advice would be don't do it.

• 1:00:52Logan Bartlett?

  Don't do it.

• 1:00:53Speaker 01

  Don't do it.

• 1:00:54Logan Bartlett?

  It's a complicated, there's a lot of people out there.

• 1:00:56Speaker 01

  It is. If you really have to, you know, it does work, but it takes 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.

• 1:01:13Logan Bartlett?

  It's probably exponential too. It's not a linear.

• 1:01:17Logan Bartlett?

  So can you talk about those early days of finding product market fit? So you guys have this idea and like, how did you actually go about validating that it worked? Presumably you had relationships.

• 1:01:28Speaker 01

  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 asked 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 was just like four. And we just gave it to our users. We're like, here, you can borrow our iPad and here's PlanGrid.

• 1:02:13Speaker 01

  And we, we helped them learn the software, which is 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.

• 1:02:34Logan Bartlett?

  And, and did the, that, that flywheel of juicing the market in the early days, I guess, or like kind of laying the groundwork, doing the things that aren't scalable. Did, 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?

• 1:02:55Speaker 01

  It took a few years to get that, get there, but we, I mean, we basically had a program.

• 1:03:03Speaker 01

  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. So again, it was friction. It was a barrier 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.

• 1:03:44Speaker 01

  It was like 2,000 bucks and we'll throw in iPad mini that will run our software beautifully. And that was a very popular SKU. People didn't have to think about it and it just shipped out of San Francisco's Apple Store.

• 1:03:58Logan Bartlett?

  You guys applied to go to YC in early? How'd you find your way to YC?

• 1:04:04Speaker 01

  Oh, my co-founders are a bunch of nerds and they were big readers of Hacker News.

• 1:04:09Logan Bartlett?

  Got it.

• 1:04:10Speaker 01

  They tried to get me to read it and it's like, this is just not my, just none of this calls to me.

• 1:04:15Logan Bartlett?

  Yeah, but you guys got in.

• 1:04:17Speaker 01

  They, there was 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 I 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 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.

• 1:04:58Logan Bartlett?

  And you guys got in?

• 1:04:59Speaker 01

  And then we got in.

• 1:05:00Logan Bartlett?

  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?

• 1:05:13Speaker 01

  Yes, we did.

• 1:05:14Logan Bartlett?

  Some friends in?

• 1:05:15Speaker 01

  Yeah.

• 1:05:15Logan Bartlett?

  Yeah, in the industry. Um, and then, I mean, this is something that I can't even imagine, but, uh, 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?

• 1:05:33Speaker 01

  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

• 1:06:20Speaker 01

  it was my way of feeling closer to him. And I think for the hackers on the team, they must've 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.

• 1:06:35Logan Bartlett?

  Did you think about not going forward or was it just?

• 1:06:38Speaker 01

  No, 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.

• 1:06:48Logan Bartlett?

  He was coding all the way up until the very end?

• 1:06:50Speaker 01

  Yeah.

• 1:06:51Logan Bartlett?

  And he gave you some really, uh, touching advice as well. Um, if you'd be comfortable sharing?

• 1:06:56Speaker 01

  Yeah, yeah, yeah. Let's see. Um, it's 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.

• 1:07:15Logan Bartlett?

  Profound, profound advice.

• 1:07:17Speaker 01

  Yeah, someone, someone on his deathbed who wanted more time and wanted to make sure that he got his last thoughts to a friend.

• 1:07:28Logan Bartlett?

  Yeah, it's pretty, pretty powerful. And obviously, I can't even imagine going through that, that experience.

• 1:07:34Speaker 01

  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

• 1:08:15Speaker 01

  and they need to recover. Like, life continues, even though we were trying to do something really hard, like starting a startup.

• 1:08:23Logan Bartlett?

  Can you draw me the through line from that hacker house to five 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?

• 1:08:37Speaker 01

  We moved out of the hacker house. We had a small office in Hayes Valley, just a thousand square feet. We crammed like 15 people in there. 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 PlanGrid 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.

• 1:09:19Speaker 01

  And so we would get phone calls. There was so much inbound for our product inbound demand. We were just 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 Planer 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 Planer 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

• 1:10:02Speaker 01

  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.

• 1:10:13Logan Bartlett?

  How do you think about that of 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 Plan Grid, it might be Procore, 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 NetSuite and whatever 99 or maybe Intact.

• 1:10:45Speaker 01

  I think AI will change that.

• 1:10:47Logan Bartlett?

  Maybe so. But how do you think about like the inevitability of a market versus, you know, trying to will yourself into a market?

• 1:10:55Speaker 01

  Well, 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 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.

• 1:11:35Speaker 01

  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 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.

• 1:11:58Speaker 01

  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.

• 1:12:22Logan Bartlett?

  In raising your Series A, Doug Leoni showed up at Plan Grid's office

• 1:12:26Speaker 01

  Yeah, he did.

• 1:12:27Logan Bartlett?

  three straight days. What was that process like? Did you guys realize you had captured lightning in a bottle to some extent? And that

• 1:12:35Speaker 01

  I was so scared because I'd heard all these horror stories about deals falling through 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, clear product market fit, which I think is interesting to any Series A investor, disrupting an entire industry for the first time. 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. And I signed the one with a heart on it because I thought it signaled that they cared more.

• 1:13:16Speaker 01

  But I think I should have done more about just evaluating the partners that we worked with.

• 1:13:22Logan Bartlett?

  What is the lesson now, other than don't sign based on the emojis that are put 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

• 1:13:34Speaker 01

  Yeah, he was surprised. I told him a few years later that he did that. He's like, really? I did? I was like, let me have a picture of it.

• 1:13:40Logan Bartlett?

  Yeah, yeah. Other than take your time and be deliberate, was there any lessons?

• 1:13:44Speaker 01

  Yeah, just spend spend time with the partner.

• 1:13:46Logan Bartlett?

  Get to know them.

• 1:13:47Speaker 01

  Yeah, is this someone you want to work with? Because it's going to be if you're if you're lucky, it's going to be a 10 year journey. If you're really, really lucky, it's going to be a 10 20 year journey or longer.

• 1:13:55Logan Bartlett?

  You were at Autodesk for a year.

• 1:13:57Speaker 01

  Mm hmm.

• 1:13:57Logan Bartlett?

  Was it your obligatory, you signed on for a year to kind of manage the integration?

• 1:14:01Speaker 01

  We were actually out shorter than our required 18 months. 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.

• 1:14:22Logan Bartlett?

  Um, you tried being a VC for a bit or?

• 1:14:25Speaker 01

  We did. It's a hard job.

• 1:14:27Logan Bartlett?

  Did both of you do it?

• 1:14:28Speaker 01

  We both worked for Y Combinator.

• 1:14:30Logan Bartlett?

  Oh, wow. Uh, what did you, uh, dislike about that job? Or what pulled you back into being a founder? I guess two separate questions.

• 1:14:38Speaker 01

  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 Y C 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 Plankford. It's why I decided to build Tiger Eye. 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.

• 1:15:22Speaker 01

  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.

• 1:15:37Logan Bartlett?

  The feedback loops are very long and 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.

• 1:15:51Speaker 01

  Yeah. And I saw, I saw what I thought were successful VCs and I it was clear to me I didn't have that.

• 1:16:02Logan Bartlett?

  You referenced this earlier, but both companies you've started were pain points that you uniquely felt. Do you think that's a key ingredient to being a founder? Is that something you solve for?

• 1:16:14Speaker 01

  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 a 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.

• 1:16:44Logan Bartlett?

  I had heard you say that Tiger Eye was about activism in some way for you and showing representation of female founders and CEOs in the B2B enterprise world as well. Can you speak specifically about that?

• 1:16:58Speaker 01

  Yeah, I had the privilege to work for YC for a year. 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-hanging 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.

• 1:17:43Speaker 01

  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.

• 1:17:58Logan Bartlett?

  You all have been focused on building remote from day one, which was probably an outgrowth to some extent of the circumstances around COVID when you when you got going. But also, it seems like a purposeful thing that you guys believe in. Can you talk about how you landed there and what some of the things you do to make sure you can maintain the culture and the process and the documentation and all that stuff?

• 1:18:24Speaker 01

  Yeah, so there's trade offs 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. I got to see the power of having everyone in the office and the culture that that can bring. And now we've been running Tiger Eye for two years remotely as a much smaller team and everyone's experience, you know, the average age of Plangron when we started it must have been in the mid twenties. I'd say the average age of Tiger Eye's team is probably mid forties. So we're just more experienced and many of us have worked together before. There's trade

• 1:19:07Speaker 01

  offs to everything, but net, net for us, the positives outweigh the negatives. I'll give you a few examples. One, there are, we are a diverse team. We are all over the world. 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

• 1:19:49Speaker 01

  that works, we have flexible work hours. There's six hours each day where, because we're all on 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 six o'clock to seven 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 happens. 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.

• 1:20:35Speaker 01

  Two, everyone's really good at communicating, 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.

• 1:21:11Logan Bartlett?

  So, so the, uh, it's allowed you to hire a more diverse 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, 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 culture?

• 1:21:46Speaker 01

  There's 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 offsites where everyone comes back together like we did last month.

• 1:22:31Speaker 01

  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, like a five minute phone call or pulling someone into a Zoom room.

• 1:22:44Logan Bartlett?

  Do you think you could have done a remote startup if not for the experience? Like if you're a first time founder, do you think you could have done a?

• 1:22:50Speaker 01

  Ten years ago, I didn't think it would be possible. It wasn't until COVID happened where I was like, whoa, actually this is a lot better.

• 1:22:56Logan Bartlett?

  And if you hadn't lived the experience of PlanGrid though, do you think if you were a first time founder today at 26 years old or whatever?

• 1:23:04Speaker 01

  I think it's possible. I don't think it would have been possible for me.

• 1:23:07Logan Bartlett?

  Got it.

• 1:23:07Speaker 01

  It'd been, it'd been too hard.

• 1:23:09Logan Bartlett?

  Yeah.

• 1:23:10Speaker 01

  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 was remote. If I had to drive to an office and sit there for eight to 10 hours a day. It'd be really, really hard to, to want to do that and live that life.

• 1:23:26Logan Bartlett?

  What pulled you out of, you, 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?

• 1:23:58Speaker 01

  It's funny you say that because um, couple of folks, we really wanted to recruit us on the team. I did look them in the eye. It's like, this is the last company. I'm not starting another company.

• 1:24:08Logan Bartlett?

  Yeah.

• 1:24:08Speaker 01

  So if you've ever thought about working with us again, this is it. This is the time to join Tiger Eye. You know, it's, we are, we are busybodies. 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 spreadsheet 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

• 1:24:49Speaker 01

  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

• 1:25:35Speaker 01

  of a CEO at our home life. But it's welcomed in the 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.

• 1:25:51Logan Bartlett?

  What's the advantage of keeping Tiger Eye in stealth for the first two years or how, how long?

• 1:25:57Speaker 01

  It's been two years.

• 1:25:58Logan Bartlett?

  Two years.

• 1:25:58Speaker 01

  It was just the founders, the two of us.

• 1:26:01Logan Bartlett?

  Initially.

• 1:26:01Speaker 01

  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.

• 1:26:18Logan Bartlett?

  Was there something about the copycat experience with PlanGrid that led you down this, uh, this path?

• 1:26:25Speaker 01

  Yeah, I'm still shell shocked from 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 billed, it's Autodesk billed. 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?

• 1:27:07Speaker 01

  Um, we wanted to come out into the market strong.

• 1:27:11Logan Bartlett?

  Yeah, have customers live.

• 1:27:12Speaker 01

  Because again, we were so seen as a point solution in the market in 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, um, the past, present day and future.

• 1:27:43Logan Bartlett?

  One of the things I heard you say to founders is that they should keep their, uh, personal burn rate low in the early days. Um, why is that the case?

• 1:27:51Speaker 01

  Because you might not pay yourselves for a really long time in a startup. Um, that was true for PlanGrid, that is true for Tiger Eye, although circumstances are different, of course. And so if you keep your burn rate low, then you can just last longer. At PlanGrid, I remember we were all engineers, we were 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.

• 1:28:30Logan Bartlett?

  There's a quote I heard you reference, "Face reality as it is, not as it was, or how you want it to be," by Jack Welch from GE.

• 1:28:36Speaker 01

  By Jack Welch, yeah.

• 1:28:37Logan Bartlett?

  Why do you like that quote?

• 1:28:38Speaker 01

  Oh, I love it. It's like my motto. I think it's incredibly practical advice for any problems, whether it's personal or in business, 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 body reaction of like flight or fright or freezing and not doing anything. Well, if you can just forget about the expectations and just look the problem in the eye and let yourself go where it hurts, then you can actually start solving the problems instead of spinning your wheels about what should have happened or what should not have happened.

• 1:29:21Speaker 01

  Because what's in the past is like, totally doesn't matter. 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.

• 1:29:42Logan Bartlett?

  I heard you say that you should raise or not, and there is no in-between.

• 1:29:46Speaker 01

  Oh, yeah.

• 1:29:47Logan Bartlett?

  Venture capitalists can be pretty compelling to sit down with and talk to about businesses at times.

• 1:29:53Speaker 01

  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 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.

• 1:30:25Logan Bartlett?

  How do you tie that back with the three-day process in the early days and getting to know someone? How do those two things fit together?

• 1:30:32Speaker 01

  If I could do that round over again, I might have run a one-month process and talked to as many people as I can and see who's the best partner for us.

• 1:30:40Logan Bartlett?

  Got it. So when you're in fundraising mode, focus on it, but spend the time. You don't need to get to know someone over... Months or years, you can, you can, you can keep it short in terms of process, but just really dedicate yourself to it.

• 1:30:54Speaker 01

  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, the attraction and please buy a piece of it. Right? And you're getting diluted as part of it.

• 1:31:15Logan Bartlett?

  You have very specific opinions about how to structure board meetings. First, what do you view as the purpose of a, of a board meeting?

• 1:31:23Speaker 01

  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 getting to do this a second time around, and we're, we're a young company where we can keep

• 1:32:06Speaker 01

  our board meetings short because not much is changing, not many decisions are needing to be made. 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. This kind of a lot of waste of time trying to update the board where now it's,

• 1:32:51Speaker 01

  let's run the business, let's show them, let's just take screenshots of like the work we've been doing, dump it in this letter I write to the board. There's no preparation I'm really doing other than like piecing everything together into a 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.

• 1:33:23Logan Bartlett?

  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

• 1:33:33Speaker 01

  Time-based snapshot update and then zooming out on what's going on in the market. This 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.

• 1:33:55Logan Bartlett?

  How do you think about work-life balance now that you're?

• 1:34:00Speaker 01

  Yeah. One of our core values at Tiger Eye is wholeheartedness. 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're at Tiger Eye, I don't want them thinking about their personal lives. These are the hours dedicated to Tiger Eye. I'm here with you too. And we're going to have our hearts completely here for this period of time. And then after work, it's their own time. Like again, I don't want them answering messages from me or anyone.

• 1:34:40Speaker 01

  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 about being present. I'm here with you right now, Logan.

• 1:34:57Logan Bartlett?

  You are.

• 1:34:57Speaker 01

  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. In about 10 minutes, hopefully, whenever this interview ends.

• 1:35:06Logan Bartlett?

  That was my last one. So now, actually, that was my last question. So thank you for doing this. This was great.

• 1:35:14Speaker 01

  Yeah, thanks for the conversation.