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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

Her Father Ignored Her For 8 Months When She No Longer Wanted To Be A Doctor

This may have happened to you (maybe not the musical writing part), or you may know someone from an Asian background who is currently struggling as their parents had strongly expected or already had chosen a job for them.

But how many of you have bravely rejected your parents’ desires, and followed your true passion? Take it from this courageous girl, Joy Regullano. You might remember her from the viral YouTube sketch called White Fetish, or various random acting gigs like the TV Series Crazy Ex-Girlfriend (her line was “Yeah, bitch!”) or Modern Family (with her line was “You fools!”).

That’s right, Joy is quite too far from wearing a white coat. She’s an actress, comedian, and writer — every Asian parents’ nightmare. So when she told her parents that she didn’t want to be a doctor anymore, her father didn’t talk to her for 8 months. Years later, she wrote a comedy musical about it, called Supportive White Parents.

“Working on this musical has been a major part of my healing journey (my parents are imperfect people who were just passing down intergenerational trauma) and maybe it can be part of yours too,” Joy expresses.

Read through as Joy shares how she has discovered her passion for comedy, and her journey to healing and acceptance through her musical.

MY WHOLE LIFE, I THOUGHT I WAS GOING TO BE A DOCTOR JUST LIKE MY PARENTS

My parents were born and raised in the Philippines. My dad grew up very poor in one of the provinces, but after scoring in the top percentage of all students across the country on an exam, he got a scholarship to a prestigious science high school in Manila that was all expenses paid. My parents met in medical school, and soon after graduating, they came to the US by way of New York. Eventually, they made their way across the country to Eagle Rock in LA and then Orange County, where I grew up. 

My whole life, I thought I was going to be a doctor just like my parents. I tried my best to be the perfect daughter. I got straight A’s and took piano lessons since I was 3 and violin lessons starting at 8. (Well, actually, I got one B+ in AP/IB Physics, but we don’t talk about that B+) I studied math outside of school at Kumon and played educational computer games because it was a productive use of my time. I read medical books my parents had lying around the house and had subscriptions to science magazines in high school, for fun.

But as I grew older, there was a part of me that was starting to love writing and making people laugh. For 7th-grade vocabulary exercises, I cared more about making my sentences funny than using the word right. My favorite part about English and Spanish group projects was writing the scripts and acting in them. I wrote bad high school poetry. But I didn’t think that was an acceptable thing to want to do with my life, so I shoved that part down, deep inside me. I did write for the school newspaper and compete in speech contests and debate teams, but that was about the extent of my (public) creative life. 

But as I grew older, there was a part of me that was starting to love writing and making people laugh.

-Joy Regullano

I LOVED FEELING LIKE I COULD MAKE THE AUDIENCE LAUGH AND CRY JUST BY TELLING AN HONEST STORY

I went to UC Berkeley pre-med and was planning to take over my dad’s clinic when he retired. But in the first semester of my freshman year, I got a B on my first math test and a C on my first chem test, and I panicked. After some soul-searching, I realized I wasn’t actually passionate about any of that and ended up cycling through a bunch of different majors before landing on Theater and Southeast Asian Studies.

I wrote a play in college about a friend who had passed away in high school, and when I put it up in front of an audience, I was hooked. I loved feeling like I could make the audience laugh and cry just by telling an honest story. Just by being myself. I wanted to do that for the rest of my life. I loved Tina Fey and Amy Poehler’s work so much that I couldn’t even watch them for a long time because it hurt that I wasn’t doing what they were doing. 

WHITE PARENTS: A MUSICAL INSPIRED BY MY LIFE

I wrote the book and the lyrics to a comedy musical called “Supportive White Parents” about an Asian girl who tells her parents she doesn’t want to be a doctor anymore, and when they’re disappointed, she wishes on a shooting star for supportive white parents. Eventually, she learns to love her Filipino parents for who they are. My friends Sam Johnides and Tony Gonzalez wrote the music.

The musical was inspired by my life. When I told my parents I didn’t want to be a doctor like them and take over my dad’s clinic, my dad yelled at me, called me selfish, and didn’t talk to me for 8 months. I was absolutely devastated, even though I knew that making people laugh and cry was what I had been put on this earth to do. 

I felt so jealous of my white theater classmates with their seemingly endlessly supportive white parents. And funny enough, they were jealous of me because I had something called “discipline”, played multiple instruments, and knew other languages. And thus, the seed of a musical was born.

Eventually, she learns to love her Filipino parents for who they are.

-Joy Regullano

LAUGHING AT OURSELVES CAN BE ONE OF THE BEST WAYS TO HEAL

There aren’t many Asian American musicals, let alone comedy Asian American musicals. One of my teachers says that comedy is the back door to the truth. I think that laughing at ourselves can be one of the best ways to heal, as well as realizing that we are not alone. 

We as a generation are going through this together, and also, we, as well as our parents, are the products of society and intergenerational trauma. We are all imperfect people who are trying the best we can with the tools we have. 

ACCEPTANCE IS THE QUICKEST WAY TO SANITY AND PEACE

I love the serenity prayer. There are some things that we can change, and we should do what we can to change those things. There are some things we can’t change, and it’ll drive you crazy trying to. You can’t control other people. You can only control yourself. The sooner you can accept other people are how they are, the sooner you’ll stop giving your energy away. 

Also, one thing I learned that blew my mind is that it’s actually not love, to wish that your parents or family were different than who they are. If what I was asking from them was to love me for exactly who I am, with all my imperfections, isn’t that what I should be giving them too? Unconditional love and acceptance? (That’s not to say that you shouldn’t have boundaries – that could be a whole other article.) But accepting things you can’t change is the quickest way to sanity and peace. 

If what I was asking from them was to love me for exactly who I am, with all my imperfections, isn’t that what I should be giving them too?

-Joy Regullano

It’s a daily practice. But try it! After reading “The Subtle Art of Not Giving a F*ck”, I tried to imagine that I only had one f– to give a day. How much energy would I be saving by only getting bent out of shape over the most important things!? I’m not really good at giving only one f– a day. But I’ll keep trying.

One more thing – some people need to be angry before they move to acceptance. I know I did, and I still feel angry sometimes. Accepting yourself and your feelings is part of the process too. Wherever you are in your journey is okay.

CONNECT WITH JOY

Instagram: @supportivewhiteparents @joyregullano

Twitter: @swpmusical @joyregullano

Website: www.supportivewhiteparents.com

Be on the lookout for the upcoming Supportive White Parent concept album, to be released in January 2023, with singles leading up to it! 

  • 8 min read
Image Source: Melissa Keomoungkhoun / Tatsu Dallas

News

Dallas Omakase Restaurant Makes Memorable Dining Experience For Deaf Couple With Staff Using ASL

Victor Montiel and Melissa Keomoungkhoun were on the verge of tears as they expressed their gratitude to the Tatsu Dallas’ personnel for making their experience unforgettable.

The couple, who are both deaf, revealed in Today that they are used to getting ready in explaining themselves using their voices and American Sign Language, displaying texts from their phones, or even asking for pen and paper.

Melissa’s sister was worried that interaction with the staff would be difficult because she was aware that “omakase” means that diners receive meals that include foods chosen especially by the chef, which means more word-of-mouth discussion.

In advance of this, Melissa wrote Tatsu to inquire as to whether they could still enjoy the meal to its fullest without being able to hear the chef describe each course. She was shocked to learn that they had already gotten the tasting menu, which also listed the available drinks/cocktails, and that a complete menu will be available when they visited.

What surprised them more was the night of their reservation as they were greeted in American Sign Language (ASL) by the staff, including the Beverage Director who is the wife of the chef-owner.

Melissa was quoted saying that “With the staff signing at Tatsu, we didn’t feel left out even though it created some attention in the room.”

She also shared that they gazed in wonder at the excellent service that they received.

The excellent personnel and food service that Tatsu delivers to its guests were posted on Twitter by Melissa’s sister Nataly Keomoungkhoun, the online dining editor of D magazine. Her tweet received thousands of likes and retweets.

The chef-owner Tatsuya Sekiguchi, claims that when working in New York City, he had an encounter that solidified his resolve to always offer the best service he can, he stated “I believe that everyone and every day are unique.” He went on to clarify that his current objective is to just make every meal a special and memorable one.

In her tweet, Nataly put into words how Tatsu exceeded the couple’s expectations where they had the best experience possible.

  • 2 min read
Image Source: Michael Tran / FilmMagic file

News

Award-Winning Director Ang Lee To Direct Bruce Lee’s Latest Biopic With Son As Lead Role

Multi-award-winning director Ang Lee is set to direct Bruce Lee’s latest biopic with his son Mason Lee playing the role.

The martial arts legend died young at 32 in 1973, a month before “Enter the Dragon,” the first Hollywood/Hong Kong film he co-produced, was set to premiere as mentioned in NBC News.

Since his passing, many biopics have been made like Dragon: The Bruce Lee Story, Bruce Lee: A Dragon Story, Bruce Lee: The Man, and many more.

And now, the Academy Award–winning director of “Brokeback Mountain” and “Life of Pi,” along with Lawrence Grey, Ben Everard, Brian Bell, and Shannon Lee, Bruce Lee’s daughter, will be directing and co–producing his newest biopic in honor of him as an actor, style icon, leader, and philosopher who brought martial arts to the global stage.

Ang’s son, Mason Lee, who is known for his roles in “Hangover Part II” and “Billy Lynn’s Long Halftime Walk,” will be playing the role.

“Accepted as neither fully American nor Fully Chinese, Bruce Lee was a bridge between East and West who introduced Chinese Gung Fu to the world, a scientist of combat and an iconic performing artist who revolutionized both the martial arts and action cinema,” Ang Lee was quoted saying.

He also said that he feels driven to share the story of this intelligent, singular human being who craved belonging, possessed incredible strength in a 135-pound frame, and through unrelenting hard work, converted impossible goals into reality.

Ang Lee is the first person of color to win the Oscar for best director and directed the 2000 martial arts film “Crouching Tiger, Hidden Dragon,” the highest-grossing foreign-language film in U.S. history. 

As an accomplished director, 12 of his 38 films which were nominated for Academy Awards won. 

Meanwhile, 3000 Pictures president Elizabeth Gabler said that Ang has long dreamed of directing Bruce Lee’s biopic, an inspirational tale of twists and turns, a story of the timeless premier real-life action hero.

  • 2 min read
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Stories

How Christopher Thang Juggles Medical School and Entrepreneurship With Time Optimization Strategies

You don’t really need to feel motivated to start — you just need to start! (easier said than done, right?)

While it’s also important to understand why you put off doing something and what causes it, what’s even more important is overcoming it.

Christopher Thang is a medical student at the University of Texas Medical Branch. He is also an Online Fat Loss Specialist certified by the National Academy of Sports Medicine.

His current mission is to help busy working professionals lose 15+ lbs in 60 days with his Progressive Eating Strategy and fitness-lifestyle optimization systems.  

Read through as Christopher shares how he manages his time as both a full-time medical student and entrepreneur.

The Chronic Procrastinator

Now, I am not saying I have the busiest schedule out there, and I definitely do not. But, I’ve included a breakdown of my time-saving strategies below that help me find time to work on my business, study for medical school exams, and travel across the US to meet clients.

My deep dive into time management started in college. I was a chronic procrastinator and always rushed to meet deadlines the night before they were due. This left me super anxious and my disorganized tendencies, unfortunately, caused me to arrive late to almost everything. It got so bad that I showed up late to or forgot about work meetings, social events, and even important family gatherings.

Eventually, I had enough of winging my schedule every day (some days I didn’t even know I had tasks due). I tried countless things to improve my time management, and after a few years of trial and error (still ongoing), I came up with these 3 approaches that helped.

I was a chronic procrastinator and always rushed to meet deadlines the night before they were due. This left me super anxious and my disorganized tendencies, unfortunately, caused me to arrive late to almost everything.

-Christopher Thang

Strategy 1: Time Block Everything

Simply put, I time block my entire day out on Google Calendar as the day goes along. It may sound intense, and it honestly is… But, after I delegate tasks, meetings, and other life events, I gain structure and peace of mind for the day. I’m also able to look back at each day to see what I can be more efficient on.

Now, I don’t time block out every single minute of each day a week in advance (would be overwhelming), but I plan ahead for important events. By including things such as meal prep, working out, and business meetings, I can make a micro-commitment beforehand to fit these things into my schedule.

On the day of such events, I time block my day in 15, 30, or 1 hour+ chunks. Once I gain control and understanding of my time, I leverage it to do more work in less time throughout the day (of course, I have to be realistic when time blocking out tasks). I’m also able to enjoy social events, family time, and travel without worrying about work which brings me to Strategy 2.

Strategy 2: 100% Work or 100% Relaxation

Building off of Strategy 1, I stick to a hard rule of either working 100% or relaxing 100%. I take every effort to avoid the gray area in between, where I’d end up working inefficiently or trying to relax (and failing) because work is on my mind.

So, on my calendar, I include 15-minute blocks labeled “Break” (when I’m dividing up work into several chunks using the Pomodoro Method) and long hours blocked off for “Social Events” or “Family Time.”

Of course, life happens frequently, and sometimes events may take longer/shorter than expected or something may come up that interrupts my entire schedule. This brings me to Strategy 3 below.

Strategy 3: Plan Ahead, But Be Flexible

Whenever something unexpected happens, I time block it out in my calendar and shift everything down (Google Calendar lets me click and drag events around on my phone really easily).

Sometimes I shift down tasks so much that I have to move them on to the next day (if possible), but I remind myself to stay realistic if life suddenly hits on some days.

Connect with Christopher 

Now, I didn’t develop these approaches overnight, and they took time to develop into daily habits.

However, I hope my strategies would be able to inspire others to stay mindful of their time and perhaps try some of my approaches to elevate their personal lives and hustles.

Linkedin: Christopher Thang

Instagram: @christopher.thang

Website: https://www.hgbtconsulting.com/free-case-study

  • 4 min read