Tracy Young is a founder who has been on my radar for a long time. Beyond the fact that she is a successful exited founder, having sold PlanGrid to Autodesk for just under $900 million, Tracy’s family–like my own father–immigrated to the United States following the Vietnam war. With one major success under her belt, Tracy is going for a second, having recently founded a new startup named TigerEye, which focuses on AI-powered strategic planning. I sat down with Tracy to chat about lessons from PlanGrid, what she’s currently working on at TigerEye, and her identity as an Asian woman.

On Identity

I wasn’t the only one with a newsletter on the call! Tracy also recently started a LinkedIn newsletter titled Predictable Growth, a monthly Q&A with women leaders generating revenue for their businesses. I asked Tracy what the motivation behind starting it was, and what she hoped to see it accomplish:

Representation matters. In sales and go-to-market functions, women are underrepresented at the leadership level. However, many impressive, talented, and hardworking women have achieved the CRO/CMO level, and I wanted to hear their stories. So, it’s a way for us to showcase women and give them a platform to tell their stories and how they got to where they are. There are many great jobs in sales, but many women don’t realize that they’re available to them. Anyone can be good at sales, it’s not just men. Reaching the highest levels in sales gives women a lot of power to help out their families, help the economy, etc.

In previous interviews, Tracy has pointed out how women are especially underrepresented in enterprise SaaS. I asked Tracy if she had any ideas why this is the case, and how we can increase representation:

I’m not sure why that’s the case. But you can see it if you look at the stats or walk into any enterprise company. I would guess it’s systemic. I think it starts with the words we use for boys and girls, the way we treat them, and what is expected of them. This is part of our cultural history. One way to change that is to show what is possible. What Predictable Growth aims to achieve is to showcase all these women who are leaders at their companies. There’s no decision that the CEO is making without running it by them. We want to say: “This could be your future, if you want it”, for anyone reading, and hopefully, it’s a young woman reader.

Next, I wanted to get Tracy’s thoughts on how being an Asian woman has affected her experience as a founder:

My PlanGrid co-founder, Ryan, and I met in college. He’s been trying to convince me to start a company with him since I was 18. Being an Asian woman, I didn’t think it was possible. I brushed him off for many years. I thought, “I’m not a founder,” because I looked at all these other founders, and they didn’t look like me. That kept me from starting a company for a long time. Around 2007-2009, I remember Ryan really wanted me to apply for Y Combinator with him. And again, I told him, “I just don’t think it’s going to work.” I didn’t think other people would accept me, and I didn’t want to put myself through it. It wasn’t until Y Combinator put out a request for startups working on the exact problem we were working on that I felt comfortable applying. That request for startups almost gave me permission to apply to YC. But even when we got in, and we were making real revenue, and we fundraised, and we had real customers, and our product was getting better… even then, I still felt that founders should look a certain way. I don’t know how many years in we were before I finally realized how wrong I was.

In an interview eight years ago with Ron Miller at Techcrunch Disrupt, Tracy responded to a similar question very differently. I asked her what motivated her shift in perspective since then:

Back then, I really tried to separate myself from being a woman. I felt like that was not part of the equation. And again, it’s such a big part of me, I am a strong woman. For many years, I pretended that I wasn’t, down to how I dressed. What really woke me up was becoming a mom. Going through pregnancy and birth and postpartum recovery, and taking care of a baby, I think it was really at that point when I realized how strong women are, how strong our mothers and grandmothers are, and how strong my colleagues are. It was a disservice not to acknowledge that our journey is different. It’s not better or worse. It’s just different.

TigerEye

I asked Tracy how she came up with the idea for her new startup, TigerEye:

There’s no shortage of problems to solve in business software. If you talk to anyone who works for a public company, you’ll find a lot of outdated software still in use. After selling my last startup, I worked for a public company and got to use these expensive products that our company was paying for every year. I saw firsthand how they made us less productive and frustrated our team. Many areas need improvement, such as HR software, finance software, sales software, and everything in between, including development tools. 

A common strategy I hear from founders is that they want to start by selling to other startups, and then grow into an enterprise software company alongside their clients. I asked Tracy how she decided to skip that and go straight for enterprise customers:

I like to solve problems that I have experienced. TigerEye comes from my experience running a fast growth company for ten years. When we reflected on our PlanGrid journey, we asked ourselves a few questions: What would have accelerated growth? What would have made the difference between us still running PlanGrid today versus needing to sell? TigerEye is that product. This is a scientific tool that would have helped us grow more efficiently, be more profitable, and would’ve enabled us to be more courageous in our decision-making by providing extra validation. It’s an AI-powered business simulator. You can test out your plans before you make your team execute it. You can test out as many plans as you want and as many scenarios as you want before you bring it to the board for sign-off. Back at PlanGrid, we had a bunch of very smart people trying to generate the same thing that took months that TigerEye is outputting instantaneously now. This is the product that I wish I had to help grow PlanGrid. And this is why we are building for the enterprise. All I know to do is build things to help me with problems I’ve faced.

Starting a Company as a Second-time Founder

I asked Tracy what she thought about distribution at PlanGrid, and how that has changed for TigerEye:

PlanGrid was always mobile first. We really benefited from timing. Steve Jobs announced the first generation iPad, and we decided to start building construction software for that device soon after. We were one of the first enterprise apps to launch on all of the app stores. 

Let’s say you’re a construction person and you’ve got your new iPad or other tablet. You search for construction because that is your profession, and PlanGrid pops up as the top result. If it looks interesting, you might download it, and we had a freemium model so users could try us out. As a mobile-first company, having great SEO on the app stores was crucial for our inbound growth. That’s how we thought about distribution for PlanGrid, but that is totally irrelevant for TigerEye (although we do have a mobile version of our software). TigerEye is an enterprise-grade product, and you can’t just try it out as an individual. It is being deployed to whole departments, and that is a completely different distribution model. For many years, PlanGrid was sold on a per-seat basis. At TigerEye, we have an unlimited seat model, and it’s deployed to several teams at once, and the starting fee is five figures. It’s an enterprise-grade product. And so for us to get deployed and adopted usually takes a field sales team two or three conversations with the company, because it’s not just sales, it’s revenue operations, it’s strategic finance, and then it’s a champion at the C-suite level. It’s very different from PlanGrid’s model, where anyone with a credit card in a job site could swipe their credit card and buy PlanGrid today.

Next, I asked if she felt that being a second-time founder came with any benefits:

There are definitely benefits. For example, the first 15 people we recruited were people we had handpicked and worked with before. As a result, we were able to recruit a talented team with a strong track record and a strong work ethic. It’s difficult for first-time founders in their early 20s to attract talented individuals. The people who worked for us were our friends or recent college graduates. From our decade of experience, we’ve also seen what works and what doesn’t in terms of core values. This time, we made sure to have a set of values that we live by personally and professionally. These core values are non-negotiable and we share them with candidates we’re trying to recruit during our first phone call. We’re serious about it. Everyone says they care about their core values, but we actually hire and fire by them. 

Tracy’s emphasis on core values stood out because this was the first time I had heard a founder emphasize them to this degree. I asked Tracy why this mattered so much to her:

Through my experience growing PlanGrid to 450 employees and scaling the team to 1,300 employees post-acquisition, I got to see what slows down a team. I got to see how infighting can destroy a company. There are minor things that you can put in place to mitigate this, such as basic rules of engagement. We have a document called “Our commitments to working with each other,” which outlines how we work together at TigerEye. The document clarifies our five core values. It’s very simple, you cannot misinterpret what the core values mean. I’ll give you a couple of examples: 1) I will walk it like I talk it. 2) I will never speak destructively behind my teammate’s back. 3) If I have a problem, I will go to you and talk it out because we’re professionals and I can trust that we can have the hard conversations. If everyone follows these rules, then we’re in a really good place. That means that when there are problems, we can speak openly as a team and get through it together. We were very deliberate about the culture and work environment we were creating, especially as a remote company. I think our culture is especially important because we aren’t together every single day.  

Fostering a Culture of Authenticity

Throughout my research, a consistent theme Tracy touched on was being authentic as a leader. I asked her if she felt there are boundaries to authenticity and if it’s fine for CEOs to express fear or lack of confidence to their team.

There is definitely a line in terms of vulnerability and authenticity. It’s never acceptable to be disrespectful. Some might argue that they’re just being direct, but there’s a difference between being direct and being rude. It’s okay to question things and suggest new approaches. When I’m concerned about something related to the company, I share it with the team. I either present a potential solution or let them know that I’m working on one. This approach makes it easier to lead and get the team on board with the direction we’re heading. They may not always agree, but at least they understand why I’ve made certain decisions. If they understand, it’s easier for them to commit to the decision, even if they initially had reservations. 

To your second question, I think it is completely okay for a leader or anyone in the company to show that they are human, and as humans we experience fear and insecurity–they are natural emotions. As a leader and a productive teammate, it isn’t beneficial to dwell on these negative emotions. It’s challenging, if not impossible, to suppress these feelings because they will eventually surface. My approach is to allow myself to experience these emotions when things are tough, but also to take control and not let them linger. For instance, I might allow myself a day to experience these feelings, but the next day, it’s time to put on a game face and figure things out together. As long as there’s movement and progress, then it’s okay. Feelings like anger, insecurity, and sadness, when prolonged, are completely useless. They don’t serve anyone any good. They’re just there making everyone feel bad and that is absolutely not okay.

I asked Tracy what actions she takes to make sure everyone on her team is comfortable being authentic and vulnerable with each other:

We do this fun activity. We all take the Enneagram test. New teammates will take the test and present their enneagram results sometime within the first few weeks. The presentations are basically: “This is when I’m at my best. This is how I am at my worst. This is how I want to get feedback.” This helps us understand who we are as people because there are all kinds of different personalities, and conflict comes from two personalities at their worst coming together. If we can acknowledge and understand that might happen, it’s easier to get through it together. Essentially, it’s having self-awareness and giving your team a blueprint of being aware of who you are. 

For those who don’t know, Enneagram is a popular personality test that emphasizes how you interact with other personality types, making it a popular choice for teams. I am normally skeptical of these kinds of tests, but even I am a big fan of Enneagram, and I think it has helped me better understand myself and my interactions with others. For those curious, Tracy is Enneagram type 1, “The Reformer”. A fitting type for a person with such ambition and vision.

Shoutouts

If you are a leader in sales, RevOps, finance, or marketing, TigerEye has built a go-to-market planning tool to help you track, plan, and predict your go-to-market performance. The tool analyzes every change in your CRM using artificial intelligence to guide decisions and show you where you’re headed.

If you are interested in checking out what Tracy and TigerEye. have built, please drop her a note on LinkedIn or on X (f.k.a. Twitter) @Tracy_Young. Thank you Tracy for the interview!

Venture capitalist Ann Lai is, by all measures, an absolute beast. From earning a PhD from Harvard at 25 to becoming Managing Director at her own firm–Skeleton Key, Ann has clearly achieved a great deal of success throughout her career. Ann is also notable for speaking up publicly about the misogyny she has faced in VC, despite it nearly forcing her out of the industry. I had the honor to chat with Ann about her career journey pre-VC, reflections on her identity, and also about her exciting new firm.

Journey to Venture Capital

Ann’s journey to Venture Capital is at least 50x cooler than mine. In fact, it’s one of the coolest there is. It all started when she read a biography of Marie Curie at the age of six. I asked Ann to explain what drew her to Marie Curie so much that it set her on a trajectory she is still on today:

The recognition of women in science has historically been insufficient, and I have consistently been attracted to narratives that feature an underdog. Marie Curie’s achievement as the first woman to win a Nobel Prize, and then winning it a second time, was profoundly significant to me as a young person. From a very young age, I had an affinity for science and engineering. My mother, a teacher of literature, encouraged me to read or listen to autobiographies of diverse individuals. My early fascination with NASA was spurred during the time my father worked there. Marie Curie significantly altered the landscape and methods of many scientific endeavors.

Marie Curie’s story inspired Ann to study science. By age 25, she had earned three STEM degrees from Harvard including a PhD in microfluidics. While studying, Ann was starting to notice things that would push her away from being a scientist towards investing:

I noticed that many significant scientific advancements were transitioning to privatization. There was a golden era of science in the United States during the 1970s, characterized by substantial government funding and innovative labs such as Xerox and Bell Labs, but it is now over. I hypothesized that the most groundbreaking scientific discoveries would increasingly be funded privately. The sectors that remained vibrant, like CRISPR and space exploration, were those receiving substantial private investment. And although I was satisfied in the laboratory, my broader interests and extroverted personality drew me toward the funding side of science.

However, that was not quite what the universe had in mind for Ann. Ann graduated right around the 2008 financial crisis, which had pretty much killed off all appetite for investments in science. Thus, she instead started her career at a firm pioneering big data analysis:

I joined a company on Wall Street that pioneered what is now commonly referred to as “alt data”. We acquired, scraped, and sourced new and proprietary datasets, transforming them into predictive models for public company earnings. This was a rigorous introduction to the underlying forces that influence corporate dynamics; we had to understand the key performance indicators driving stock market values. (It was like going through a condensed MBA program.) By modeling quarterly earnings, where data points were scarce, I applied methodologies from my graduate research, collapsing extensive data sets by normalizing or parameterizing the variables, allowing for a comprehensive, dynamic model. This approach was highly effective, blending scientific and business analytics.

After her stint working in finance, Ann went on to lead business intelligence for international territories at Riot Games and then worked in a few early-stage startups in preparation for a transition into Venture. One thing she said especially caught my attention:

There was noticeable skepticism towards PhDs and academics in venture capital. Despite my extensive scientific background, I was told to strategically minimize the emphasis on my PhD on my resume. It’s evident in the venture space that there is a prevailing belief that academics lack practical business acumen.

When asked whether this skepticism extended to PhD founders, Ann elaborated:

This skepticism is indeed still prevalent. However, many PhDs are exceptionally practical. For companies involved in iterative development, such as SaaS companies, the requirements are different. In these fields, the emphasis is more on user interaction and less on deep scientific knowledge. But, for science-driven enterprises, a thorough understanding of the fundamental sciences is crucial.

Hopefully, this gives some hope to the PhDs out there who are looking to start a company! In fact, VC has been trending more towards deep tech evidenced by an increased share of investments into the space.

Advice for Women in Venture

One aspect Ann has been noted for is her outspokenness on the misogyny she has faced in the Venture ecosystem. For more specifics about her experiences, you can check out this Elle article written about her. Given her experiences, I asked her what advice she would give to women who want to go into the VC or startup space, but are concerned about the misogyny and fraternity culture that is still rampant.

Establishing a close network of mentors and peers for support is essential. This has been invaluable to me. Unfortunately, the prevailing culture remains challenging, and the progress we’ve made has perhaps deteriorated in the past year due to decreased venture capital availability on the LP side. There’s still a lot of work to do. The solidarity of women supporting one another is crucial for fostering progress. Maintaining a commitment to support each other is critical. Although most days it may not seem particularly difficult, there are specific moments where you can just feel a very big demographic difference in terms of who’s empowered. Partners are partners, but managing partners are different categories of partners. Until more women are managing partners or running their own sizable firms as partners, there’s still not enough leverage in the space.

Being Asian

I asked Ann to reflect on how her identity as an Asian woman has affected her lived experience:

My mother is incredibly liberal for her generation of Taiwanese. She has always been supportive, telling me I don’t need to get married early or worry about having kids, which is rare for Asian moms of her generation. At the same time, my parents weren’t financially very well off when we came back to the States. I contributed to my family’s income from the age of 12. There was no safety net. If I didn’t make it, nobody could pay the bills. It taught me resilience and gave me a “no way back” approach to life.

My dad raised me with a strong sense of right and wrong (We watched a lot of Asian martial arts dramas and stories.) It’s not really about being visible–it’s about doing the right thing. This Asian heroism as defined by martial arts movies approach is quite different from American heroism, and it’s the reason why I stood up for myself even when it might have prevented me from working again.

Being an Asian woman in the US is difficult. I often get the assumption that I’m a lot younger, for example. So, you always have to go into a meeting fighting that. That’s something my cohort and I have talked about a lot, like, you learn how to dress and style yourself to appear older sometimes so that you will be taken more seriously.

For meetings in East Asia, I was coached to open meetings by stating my qualifications, the PhD from Harvard, etc.This way, they respect the degree and then they respect you. Male executives and men who attend meetings weren’t prepped in this way. But I’m starting to see more evolution, especially with the younger, successful Asian male founders and groups. They’re very supportive, which is great. The older generations still tend to have a more patriarchal mindset, but it’s getting better, especially in the US.

Anecdotally, children of first-generation immigrants often pursue more stable, high-paying careers (doctor, lawyer, etc.), yet Ann has clearly bucked this trend. I asked her why she thought she ended up doing so:

My parents have been very modern in their thinking. They’ve never said I had to do things in a certain way. They’ve always supported my decisions. It made me feel like I could do anything. I’ve never worried that I might not succeed. If you are fearless, you end up doing aggressive things, aggressive in a good way.

Having grown up in both the US and Taiwan, I think Western and Eastern education are quite different. The American system encourages exploration and aspirations, whereas there’s a lot more regimen in the Eastern education system. The way I was raised was very much a marriage of those two aspects in an unexpected way. I have a lot of friends who were told to be a doctor or a lawyer, but if you think you can do better at other things, why do you have to do that?

Skeleton Key

A Skeleton Key is a type of master key in which the serrated edge has been removed in such a way that it can open numerous locks. It is also the name of Ann’s new firm. While researching for this interview, I came across this article by Ann, where she lays out the argument for why Deep Tech is venture-backable. Towards the end of the article, she shifts the focus to ScienceTech (SciTech), which she defines as: the software, platforms, or tech-enabled services that accelerate scientific discovery or assist in bringing science to life. I asked Ann why she chose Skeleton Key’s focus to be on SciTech instead of Deep Tech:

Deep tech is definitely fundable, as I’ve talked about. But now with AI, I’m thinking about how to make deep tech happen faster. Instead of investing in a drug, I’m looking at the platforms helping people discover drugs faster. Those layers are interesting to me, and I think those are the layers where a lot of the accelerated computing power can come into fruition in an interesting way. The accelerated computing power means you can map out a lot of things that have historically been very difficult such as fatigued glass behavior or certain thermal dynamics, nonlinear dynamics, and anything that’s related to nonlinear systems. 

There’s even a lot of interesting stuff happening around the application layer of science. For instance, bringing chemicals to real-life applications usually takes a long time. You find a chemical and wonder where to use it and what it can be used for. Then, usually, you need a different type of manufacturing protocol or a different variation for each use case. But now,  you can find a lot of those variants much faster. The formulation or the tuning of that molecule, protein, etc. can be assisted on by AI and you accelerate that process of bringing it to a real-life application much faster.

As you may have gathered from her background, one of Ann’s specialties is data analysis. In her previous VC roles, Ann leveraged her background to evaluate companies based on their data in an apples-to-apples way. You can hear more about her approach in this podcast. Given that Skeleton Key is working with a type of company that isn’t what the typical VC invests in, I was curious to know if she had to adapt her process:

It’s definitely different for Skeleton Key. We deal with a lot more data around R&D and early applications because we’re focusing on a second or third institutional round for these folks–so it’s a post- R&D but before they actually hit ramping revenue. That means you still have time to work with them on exploring the business–is it a software platform approach, or is it a single molecule approach, or a single robot approach? 

I asked Ann what revenue the companies typically are at in their second or third institutional round:

I think the specific revenue number doesn’t really matter. It’s the mechanics of what the early performance looks like. If they have a couple of contracts which are scalable over time and show real adoption and real usage–that’s a lot more important than one marquee SaaS contract that you can get through relationships. It’s more around the usage, the actual day-to-day functionality or day-to-day use. 

Earlier in our chat, Ann touched on how Skeleton Key plans to help startups explore different business angles, I asked Ann to elaborate on this process:

Our approach is very collaborative. My philosophy has always been to provide as much help as the founder wants. The goal post-investing is to help them with monetization, go-to-market strategies, and thinking about how to scale from a scientific lab mindset into building a company. We also assist them in fundraising. There are a lot of resources post-investment, and whether a founder will leverage them is their choice, but we prefer that they are open to us being more involved. In this category, where there are no established revenue models and many founders are coming from academic backgrounds, this advisory capacity is helpful to give them the full lay of the land, let them explore, and let them test different monetization hypotheses quickly.  Inflexibility or lack of adaptability can be a problem down the line, especially in these categories that require a lot of money for ramping up and the revenue models aren’t so obvious. In fact, we’re planning on helping founders in this way before even investing, as part of our process.

I mentioned to Ann that this kind of help seems very valuable, especially since the only resources available online tend to be very reductive:

My biggest pet peeve is when VCs prescribe a framework without actually understanding the problem. When we help companies, we don’t do that. We workshop their unique situation and how to price best for their product, without capping future revenue. For example, a lot of people like to suggest ARR subscription SaaS, but that model doesn’t work for everyone. There’s a lot of possibilities around pricing and revenue that isn’t just about “getting ARR.” I think those are the interesting exercises to think through when you’re in these new categories.

Shoutouts

Ann is amazing  and I am super excited for the launch of Skeleton Key. If you’d like to hear more from Ann, you can sign up for her Science Fair newsletter here, where she writes about science and venture. Thank you Ann for the great interview!