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Awaken* newsletter

June 13, 2024

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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!

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Stories

This Young Baker Is Changing the Food System by ‘Vegan-izing’ Asian Snacks

Annie Wang, a baker from Oakland, recently had the opportunity of making custom almond cookies for the premiere of Everything Everywhere All At Once.

Made from only the freshest, high-quality ingredients and created with sustainability in mind, Annie’s vegan, gluten-free, and upcycled Taiwanese Pineapple Cakes are perfect for anyone who cares for the environment and their taste buds.

In this interview, Annie shares her experience of growing up in rural towns in America, where she witnessed firsthand the harsh realities of food production, her journey of developing her recipes, her passion for reducing the use of animal products, and her experience of baking for the premiere of Everything Everywhere All At Once.

SEEING THE HARSH REALITIES OF HOW FOOD WERE BEING PRODUCED WHILE GROWING UP

I was born in New York City, but growing up, my family and I moved every three years. The towns we moved to in the later years were smaller and more rural than the others. During the time I lived in these states, I saw the harsh realities of how we produce and handle food in America.

In one town in Illinois, my classmates and I had to plug our noses to guard against the toxic smell wafting towards us from a nearby pig farm. When we lived in Arkansas, we lived 15 minutes away from a Tyson chicken factory where runoff from the factory sat in huge silos. Ironically, these rural towns where I got to school by walking through crop fields were the towns where neighbors often struggled the most with unstable access to nutritious and responsibly grown food.

These towns were also where I first learned about the enormous harm inflicted on people and animals by our current agricultural system and decided to adopt a plant-based diet. That decision meant a lot of the staples I grew up eating with my family were no longer an option.

After working at environmental nonprofits and food tech companies, I decided to start Annie’s T Cakes to help myself and others once again partake in culturally important foods while also helping to improve the food system.

MY DREAM AS A KID WAS TO OPEN A BAKERY

The first thing I ever cooked was a scrambled egg in fifth grade. I forgot to oil the pan so you could say the first go was a fail. I didn’t really bake growing up unless it was a box of brownie mix or Pillsbury cookies. Most of my time in the kitchen was spent working the stovetop via stir-frying, steaming, and boiling.

I’d watch my mom cook traditional dishes like tomato and scrambled eggs with noodles or filled buns. As I got older, I started taking on more responsibilities in the kitchen and would cook tea eggs, and steamed bread on my own. I loved getting experimental. I always made my bread and dumplings in unique shapes.

Last year, my dad told me that my dream as a kid was to open a bakery. It was news to me since the one fleeting dream I can remember was about being a vet. But hey, here we are! Definitely much further than my first failed scrambled egg.

The base of the Taiwanese pineapple cake recipe only took me three tries to make (the fastest I’ve yet to develop a recipe). I started by making milk bread and buns but I remembered how much I used to love Taiwanese pineapple cakes growing up and took a crack at it. A friend of mine in Oakland runs a business upcycling tofu fiber into flour (Renewal Mill). Since the pineapple cakes didn’t need to rise as the bread did, I thought it would be a perfect way to create a gluten-free option for customers and support her business as well. 

VEGAN-IZING ASIAN SNACKS AND FOODS

I started to dig deep into climate change, including the impact of animal agriculture on the environment, when I was in college. At the time, I got involved in our school’s student-led fossil fuel divestment campaign (our school divested in 2020!).

I was taking classes and reading about all the intersections between society, the food system, policies, etc. with our environment. I also learned so much from the other passionate student activists I worked with. To this day, I still draw from the incredible strength and compassion I felt from the student leaders I worked with in those days as I think about how to build a team and partnerships. 

A couple of years after I graduated college, I started working in food tech. I was interested in the field for its vast potential to positively impact the climate by shifting our food systems. I wanted to start a business ‘vegan-izing’ the Asian snacks and foods I grew up eating for years.

When the pandemic hit and I was laid off along with half of my team, I took the plunge. Building the business now, I think really deeply about sourcing ingredients and how to make things sustainable. In addition to building a vegan brand, I also use compostable packaging and try to reuse shipping materials to reduce waste. 

We see more food products on the market these days that do not use animal products. Heavily reducing the use of animal products as a society would be huge for reducing our negative impact on the environment and taking care of all living things on our planet.

THE ‘EVERYTHING EVERYWHERE ALL AT ONCE’ EXPERIENCE

My experience baking for the premiere of Everything Everywhere All At Once was a whirlwind!

The week before the premiere, I was put in touch with A24. In each of the markets the studio had launched the movie in, they’d worked with local bakers to create the smiley face cookie that appeared in the movie, and they still needed someone for the San Francisco premiere.

When they reached out to me, I actually didn’t have my almond cookie recipe finalized yet. I had been working on the recipe for a year at that point and felt like I just had a couple of days to nail it. So, I told the studio I would get back to them, and I cranked out test batch after test batch over the weekend.

After a couple of days, I finally had it done! And just like that, the next week, I took the recipe I had just finalized, made and packed 800+ cookies for the premier. Two nights before the premiere, I had started baking at around 7 am and continued into the night packing half of them. I thought it wasn’t that late but when I looked at the time it was 4 am! Thankfully the next day my boyfriend and two of our close friends came and helped me pack the other half of the cookies and it only took us only a few hours.

To see a cookie I made in the hands of hundreds of people, including the cast and directors of a movie that has touched so many lives was a once-in-a-lifetime event, to say the least. At the premiere, one of the directors expressed his happiness to me. He told me I had been the only baker that had made an actual almond cookie. Remembering that moment, and countless others throughout the week, I am so grateful that I got to be a part of such a special event with incredible changemakers. 

ADVICE TO BUSINESS OWNERS TOWARD SUSTAINABILITY

As small business owners, most of the time we’re just running around trying to get products out the door. Compromise happens daily because bandwidth is limited and nothing ever happens in an ideal way. 

For those that are trying to find ways to be more sustainable, take small steps toward a long-term plan of sustainability. Take note of things like the ingredients you use, where you source everything from, the amount of packaging you use, etc. and make changes where and when you can to reduce your footprint. Start small and intentionally design your business in a way where you are putting yourself on the road toward your ultimate, climate-friendly operation. 

WHAT TO EXPECT FROM ANNIE’S T CAKES 

My vision for Annie’s T Cakes is to bring these nostalgic vegan treats to people across the globe, starting first in California. I also aim to support local agricultural efforts by donating profits to organizations focused on sustainable agriculture in their communities.

In the near term, I’ll be in my kitchen, continuing to bring delicious and culturally relevant foods to our community!

Website: www.anniestcakes.com

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Cooking became Leeann’s way of expressing love, even though she didn’t say it with words. When her older daughter tragically passed away, Leeann found comfort in the kitchen, and her passion for cooking grew. Her delicious Chinese dishes quickly gained fame when she catered a luncheon for her sewing clients. They loved her food so much that they encouraged her to teach cooking and cater more events.

With hard work, Leeann’s restaurant business flourished. She even got support from unexpected sources, like Carl Pohlad, the owner of the Minnesota Twins, thanks to a party she catered where Sean Connery, the famous actor, was a guest.

As word spread about her delectable dishes, lines of eager customers formed around her restaurant, and her culinary empire flourished. In time, General Mills acquired her successful chain, marking a remarkable milestone in her journey.

Leeann’s passion for cooking didn’t end with her success; it carried on through her daughter Katie Chin, who also pursued a career as a chef. Together, they became celebrated national TV cooking stars, preserving Leeann’s legacy for future generations.

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