Awaken* newsletter

September 12, 2024

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In the half-year I’ve been writing this newsletter I have only interviewed established founders. This article is my first deviation from the pattern and I couldn’t have asked for a better guest. Emily Luk–though a first-time founder–is not new to startups, having joined Stripe as a founding member of their growth team back when the company was around ~150 employees.

Now, she is building Plenty, an investment platform for modern couples. Talking to Emily has convinced me of two things, first–that this is a very large and important problem, second–that Emily is probably the right person to build it. I’m excited to share my conversation with her.

TLDR; Key Takeaways

If you only have a few moments, here are a few golden nuggets from my conversation with Emily:

  • An exercise to find your calling: Write down everything that makes you happy, ~100 words. Keep cutting the list in half until you have five words. What’s the grounding/theme that goes through all five? That’s a good starting point to find your calling.
  • Address opportunity costs before starting a company: Running a successful startup is a long journey, the average time to IPO is 7-10 years. If possible, do the things you’d regret missing out on before embarking on your journey.
  • Aspiring founders should focus on developing taste: As a founder, you don’t need to do everything personally yourself, but you need to know what great looks like. Working alongside great talent can help you develop this intuition.
  • Being relatable is a core part of business: People are much more likely to do business with you if they can relate to you. Put in some effort to learn about common interests of the type of people you want to do business with.
  • We are in the middle of a generational shift: 33% of millennials got married or entered a long-term partnership in the past five years. This is the first generation where dual-income families are normal.
  • Financial products for couples need an update: Many financial products used today were built for single-income households and aren’t adapted for dual-income families.

Tell me about your journey, how did you end up in the Bay Area/tech?

It goes pretty far back. My grandfather started two companies. One he ran for 20 years, and the other for 25 years. Then my parents emigrated to Canada, started this company, and ran it for 18 years. Growing up, I thought most people started companies. It wasn’t until my grade seven careers class, where they walked you through all the different careers and had a chart about the percentage of people in each career, that I realized entrepreneurs are less than 10% of the population. I thought it was a much higher percentage because everyone around my parents was an entrepreneur. I have always been interested in starting businesses. I was that stereotypical kid who kept running side hustles.

I read that your first entrepreneurial endeavor was a fundraiser for UNICEF.

Yeah, it was grade one, and the teacher decided to have a competition to raise money for UNICEF. The idea was to go trick-or-treating using those orange UNICEF boxes to collect donations. I lived in Edmonton at the time, which is the most populated city that far north, so winter was basically already here by Halloween. We had this competition in class to see how much money people could raise, but my parents were really worried my brother and I would get sick if we went trick-or-treating outside when there was already a foot of snow on the ground. I really wanted to make sure I wasn’t going to lose in the UNICEF competition, so instead, I decided to take a bunch of origami, fold it into different shapes like planes and boats, and sell it during recess to the teachers. All the money went to UNICEF. This was my way of being like, “Okay, great, I can do this all the time during recess for a month,” and then raise enough money instead of going trick-or-treating as a workaround for that.

Let’s go back to your story.

I’d already started my own company in high school and had been really involved with startups in university, running a student-run venture fund that organized pitch nights. Because of these experiences, I had the chance to work at the largest VC fund in Canada when I graduated.  It was an incredible experience because we got to see a large breadth of startups during that vintage. Some of the companies I personally worked on included Sonder in their pre-seed stage and Hopper in the earlier days. About two years into my time in a venture, my younger brother told me he was thinking of moving to the Bay Area when he graduated from Waterloo. We’re very close, and I wanted to be in the same city as him. Around the same time, I was thinking about applying for jobs. My brother wasn’t going to graduate yet, but I figured I would start looking for a job there. And so I started applying for some jobs and just started talking to more people and getting more involved in the Bay Area. 

Right around the same time, Stripe ended up reaching out to me. I had met members of their team, and this was back when the company was like 150 people. The company was much smaller; they had just hired a COO and were just starting to build up their business and growth teams. We chatted about whether I would be interested in joining the stuff they were doing on the growth side. Around the same time, I had gotten connected to Gold House founder Bing Chen. I went to Bing for career advice because I had a couple of other opportunities that were also in the Bay which I was considering. I was 22 years old, trying to figure out what to do with these opportunities in front of me. On top of that, I was potentially moving to another country on the other side of the continent. I don’t even know if Bing will remember this, but it left such a mark on me. He walked me through an exercise he did when he was in university. It was something he found really helpful to understand your own values and what brings you joy. 

The exercise he walked me through was to start with an empty piece of paper and write down, in free form, everything that makes you happy. Anything that brings you joy—it can be an item, an exercise, or an activity. I jotted down like 100 different words. Then he said, “Now start to cut it down. Cut it in half. Take the ones that don’t matter. Now you have 50. Now cut it down to 25.” This is when it starts to get really hard. “Now cut it down to 10. Now cut it down to 5.” With the last five words, is there a grounding or a theme that goes through all of it? If those are the things that really bring you joy after you’ve processed this and wondered, that’s probably a very good starting point to think about what you dedicate your time to.

So what were your last five words?

For me, I remember really thinking about how I loved making and empowering. That was one of the words that came out. It was empowering, teaching. I really believed in it. At the time, I had done my CPA and CFA when I was in venture, and I really understood and saw how in the world of finance, things were so opaque. I had also thought a lot about family and friends, and I started thinking about how those words could formulate into almost like my North Star. Big credit to Bing; after I went through that exercise, the answer was very obvious to me. What was so exciting about joining Stripe back in 2015 was that we were really focused on helping SMBs and startups in this opaque world of finance. At the time, payment companies were used to dealing with massive enterprises, so if you were a startup or an SMB, you basically didn’t matter. The products were terrible, it was hard to integrate, and the process of using the product was terrible. For many entrepreneurs, being able to accept money for your product or service is a critical part of running your business. If you don’t have revenue, nothing else works.

For me, it was so obvious that of all the opportunities I had been looking at, Stripe was clearly the best one. Ironically, now in hindsight, I can say this: the other thing that was really crazy was when I decided to join Stripe, I didn’t know my title. I actually forgot to ask what my title was until I received the offer letter. I didn’t even bother asking. I knew what I was going to work on, and I knew who I was going to work with. It was also by far the lowest salary package compared to all the other companies. Given how much Stripe has grown, it’s definitely turned into the best decision. At the time when I joined, it was so clear that it aligned with the things I cared about most. The other things like compensation or title just didn’t matter as much.

You took a sabbatical from work before starting Plenty in 2022. What inspired the sabbatical?

When my parents started their business, they ran it for 18 years. My grandparents ran their businesses for almost 20-25 years. So, I never thought of starting a company as a quick two to three-year journey. I thought it would be a very long journey, and I wanted to feel like I was ready to commit that kind of time and have that kind of endurance. That was one part that was really important. Travel is very important to me–being able to see the world. I knew that if I didn’t have this period of travel, I would always wonder if I missed out.

Part of how I thought about the mental preparation to become a founder is being able to think about how it might feel. One of the parts that helps with the mental endurance of it is being able to realize what might make it harder and, if possible, try to solve some of that earlier. The sabbatical year was basically that. If I didn’t have it, I would look back at the very hard moments when you need to keep going when you’re starting a company and think, “Oh man, maybe I should just stop. Maybe now I can have my travel year because I never had it. Was it worth the sacrifice?” I think it just makes it so much harder instead of getting ahead of it.

What made you feel that it was the right time to start your founder journey? 

I think of myself as a lifelong learner. When I experience anything in life, I immediately start to think about what I can learn, what I can do differently, what I would do in the future, and what might have changed the outcome. That is deeply ingrained in who I am. I realized I would probably always feel like there was more to learn and never feel ready.

My mother had a philosophy when she was running her company: you don’t need to do everything personally yourself, but you need to know what great looks like. You need to have enough exposure to know what great products, sales, and marketing look like and have that intuition. You don’t have to do every single thing personally, and frankly, you can’t. There was a point at which I realized I had been exposed to enough people who did their jobs great and did really great work. That shift in mindset was really valuable. I thought, “I might not ever feel ready, and that’s okay, but I’ve also had some experience, so maybe it is time to take a bet on myself.”

For young people who aspire to start their own business in the future, would you say that the function of what they are doing is secondary to who they are around?

Here’s how I approached it when I was at Stripe. I was really lucky because Stripe had an incredibly high talent bar. I was surrounded by so many people. I was also the youngest person on the business team, so I was surrounded by all these people who were 5, 10, 15 years ahead of me career-wise. They were at the top of their game at what they did, and I just tried to be as much of a sponge as possible. I also moved teams a couple of times, which helped with getting exposure to a lot of parts of the organization.

One of the things I’m most grateful for is that Stripe used to have this policy where every email that is sent across teams or externally, is copied to an email list so anyone in the company can read it. It’s complete email transparency. They don’t do this anymore, but for the entirety of the time that I was there, that’s what they did. Also, every single team had to send meeting notes at the end of every meeting to these email lists, and anyone in the company could read the meeting notes. Every one or two months, I would really focus on understanding what another team did. For example, when I was on the sales team, I’d really focus on what the partnership team did and read every single one of their meeting notes for two months. Then I would rotate to another team. I spent a month thinking about risk and compliance, a month reading everything in the world related to the legal side of things, and then I would rotate to what product is doing, what engineering is doing, and how infrastructure works.

It felt like I created my own mini-MBA because I got to see not just the theory but how all functions actually work in a company. I took being a sponge really seriously. It was honestly so fun for me. I know it was rare to have access to all of this knowledge, to have that quality of thought and quality of people around me that I could easily learn from.

Could that be replicated at larger companies?

It’s really only startups where you can get that level of access. Another thing that benefited my learning was that Stripe was growing rapidly while I was there. It grew from a couple hundred to a couple thousand people during my time there. Because it was growing so quickly, I saw many chapters of a startup during that time. There was such an emphasis on communication. Because the company was growing so quickly, documentation was especially critical so that work was not duplicated. That, I think, is one of the unique growth opportunities of being in a startup that is harder to get access to when you’re at a big company.

Given that you come from a family of entrepreneurs, do you find yourself asking your parents and grandparents for business advice?

I definitely talk to them about work a lot more after starting my company. Before I started Plenty, when I talked to them about work, it was sometimes a little frustrating because they’d say, “Why don’t you just ask for the promotion?” I’d be like, “Mom, it doesn’t work like that. You have to earn it and wait your time.” My mom, being an ultra-entrepreneur, thinks it’s exclusively merit-based. In reality, in a big organization, there are performance cycles, and you have to wait six months. You can’t just suddenly say, “I want to be promoted today,” and have a multi-hundred or multi-thousand-person organization just say yes. It doesn’t work like that. 

At that time, it was much harder to ask for career advice. But now, it’s really helpful because my parents deeply understand. It’s not even the practical business advice, frankly; it’s the emotional journey. It’s so hard to hire, support someone to perform, deal with a supplier not living up to expectations, or have a backup plan in case things don’t work out. These are all fairly generalizable pieces of advice that have been incredibly helpful. More than anything, starting a company is an extremely lonely experience. It’s been incredible to talk to my parents, not about the specifics like our cost per click, but about the emotional aspects. It’s hard to feel the pressure of needing to have all the answers and supporting your team’s families. They instinctively understand it on an emotional level, which doesn’t need to be explained.

What is the core problem that inspired you to start Plenty?

If you look at the two generations that are going to undergo the largest amounts of change in the next decade, it’s the baby boomers (who we are not optimistic about being able to sell software to), and then the millennial generation. The reality is that millennials are now turning 30, and this chapter from 30 to 40 years old is generally when you find a partner, buy a house, have kids, and get promoted. There’s so much change that happens. If you navigate your finances well during this chapter, you can set yourself up for the rest of your life.

We saw that it’s also the chapter where people want to take their finances more seriously. They’re actively looking for things to do, but if you’re building up to your first million dollars, there aren’t great products or services meant for that. Once you get over a million dollars, there are lots of financial advisors who are really good and can help you, but why would the best financial advisors want to work with clients with less capital? What we saw was that this industry doesn’t have the best people working with the people who arguably need the most help.

The other aspect of Plenty came from personal experience. When Channing and I got engaged, we couldn’t find any products that made it easy for us to manage our money together. We believe very deeply that the best decisions we make as a partnership are the ones we make together, and that financial decisions are very important in unlocking optionality down the road. If there aren’t great products that make it easy for you to work together, then you’re probably going to have a much harder time trying to figure out things in the future too, right? Those two things were the core motivations for starting Plenty.

Why do you think there is a gap in products to help couples manage their finances in tandem?

Nowadays, it’s normal to be dual-income because both people are educated and everything costs more. It’s more fulfilling to feel like you both have careers and jobs, and it might be necessary in order to support a family. At this point, about 80% of this generation are dual-income families and couples. 

This used to not be the case. In the two generations before us, the majority of people were single-income families. A lot of the financial products we use today were designed by people who were single-income household members of other single-income households. So it completely makes sense why they designed a lot of joint products the way they did because it used to make sense, but it doesn’t make sense anymore. 

One example of this is if you look at American Express or Chase, there is no concept of a joint credit card. You are both legally on the hook for paying the bill, but both of you don’t get to see what you’ve spent. That doesn’t make sense. So if you get a credit card with Chase and add your partner to it, your partner doesn’t even get a login. They can’t see anything, even though they have a credit card with their name on it. American Express is quirky in a different way. We have both of these cards and from personal experience, when you add your partner to an American Express card, they can only see what they spent on their card. They cannot see what you’ve spent on the main card, even though you both share the card. 

There are all these little bumps related to access or permission, but it dates back to a time when it was very normal for one person to earn an income, but it’s not very normal anymore. People and couples nowadays expect to have fairly equal access to understanding their money together. It’s not the same as, “Oh, if they know everything, that’s fine. I don’t need to know anything.” That’s just not nearly as common anymore. Nowadays, conversations around family finances are happening with both people being more equal than ever before. 

What we also noticed is that because people are getting married later than ever, they are already used to having their own financial accounts. Even after getting married, maybe they open up some things that they share. But it’s a journey towards sharing more of their finances. They still have things under each of our names. A lot of the financial system was built around the reality of the single-income family that had everything fully joined. But that’s just not the case anymore. That has changed especially quickly in the last five years. Five years ago 33% of this generation was married, and now almost 60-70% of this generation is married or in a long-term partnership.

How do you think being Asian has impacted your founder’s journey? 

For better or worse, I have been on the other end of bias, but not because I’m Asian. At least, I think not because I’m Asian. But for other reasons, like being part of a husband and wife team. I’ve even had a VC comment about how he would never report to his wife. I don’t think anyone has ever explicitly called out the fact that I was Asian, but it is something that I am aware of. And here’s the reason why. I feel like I have to work extra hard to be relatable, and frankly, there are assumptions that people have.

My husband is from Virginia and his family’s been in the US for a while. Lots of people are surprised when I mention that I’m the sports person in the relationship. I watch basketball, I watch football, I know the players, and he doesn’t watch any of it. Even when we’re in conversations with potential investors, they’re surprised by that. I don’t know why that might be the case, but I joke about it. I say, you probably wouldn’t have expected a short little Canadian Asian female to know this much about football, right? 

I do think what you like to talk about is important. When it comes to attracting business partners, of course, the way you think about business and strategy makes people want to work with you. But there’s another aspect to it. If someone feels like you have something in common with them, they think that you can be a friend. Whether or not they want to spend more time with you is actually really impactful for whether or not they want to back you.

I think I’ve always been aware that I have to work extra hard to be relatable, but I don’t try to spend too much time thinking about it beyond thinking of ways that I can support other Asian founders, because it’s not something I can change. Frankly, I just focus on what needs to be done. I’ve always enjoyed football, but I’ve definitely put in the effort to stay aware of what’s going on because I know it is something that is unexpected when I talk about it.

I’ve talked to a few female CEOs whose husbands are also part of the company. Can you comment on what that’s like?

I think it might be happening more frequently as we go along. I mean, it makes a lot of sense, right? There is no one else in your life that you respect, admire, and trust to that degree. Building a startup is not an easy or linear path. In those moments where you’re like, “Oh gosh, what should we do?” not needing to doubt if you’re building with the right person or if you can trust that person is actually so important. It helps stabilize you through the hard moments because you know they’re in it with you, you can trust them completely, and they care about you. That psychological trust is crucial.

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Plenty is hiring! If you are interested in working with Emily to build financial tools for the modern couple, check out the available job listings here!

Emily has also graciously offered a 3-month free promo code for our readers. If you are interested in trying out Plenty, use code AHNCommunity to get 3 months free. Thank you Emily for joining us!

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Ann Lai

Awaken* newsletter

VC Veteran Ann Lai is Leading the Charge to Fund the Future of Science

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!

Larry Liu

Awaken* newsletter

Weee! Co-founder and CEO Larry Liu reflects on his underdog journey

Welcome to another edition of AHN awaken*! Apart from our guest, I’m excited to introduce a new member of our team, Han Yue Yin! Han Yue is a current Stanford GSB student and was my fellow jazz bandmate in college. Although this article was written by me (Edwin), Han Yue co-interviewed with me and will be taking the lead on writing some great articles in the future. Everyone, please welcome Han Yue!

Our guest for this edition is Larry Liu, co-founder and CEO of Weee! (exclamation mark included). Weee! is the leading online Asian supermarket in America, think Amazon but for Asian groceries. Larry is an exceptional founder, and his journey of immigrating to America without any connections into founding a company worth $4.1 billion truly exemplifies the American dream. As an aside, Han Yue and I were especially excited about this interview as avid users of Weee! ourselves. Without further ado:

The Origins of Weee!

Our first question for Larry was how the idea for Weee! first came about:

Originally, we started as a WeChat (Chinese messaging app popular with the American diaspora) group-buying company. I believe it was really an opportunity we observed around the 2014-2015 time frame. This was when WeChat became extremely popular among Chinese immigrants and many people formed WeChat groups to buy food together, among other things. We found this to be a very interesting business model. As you may know, I was an eBay seller for more than 10 years and was familiar with the traditional e-commerce model, which is search-based. So, when I saw the group buys, I thought it was a completely new model, not search-based, but recommendation-based. I believed it was very promising. That’s when we decided to quit our jobs and start the business. However, it turned out not to be the right model. We pivoted in 2017 because social buying was not what we thought it was. It was not the ultimate solution to solve the lack of service experienced by Asian Americans for their food needs. The delivery-to-home model is a much better model. So, we pivoted in 2017. I believe it’s one of the greatest pivots in history.

The reason we pivoted was because we couldn’t grow the original group buy model. We couldn’t raise money because we didn’t grow. This forced us to think very hard about the fundamentals. That’s when we realized that the reason most people used group buys was actually because they didn’t have easy, affordable access to the food they love. It wasn’t apparent in the beginning because people were group buying all kinds of things. But those were only distractions. When we thought deeper, it was about the food. That’s why we had to pivot. 

Following up, we asked Larry what lessons they were able to port over from their group-buying stage into their current business model:

We learned a lot during the group buying stage. We had already built some warehousing and delivery capability during the group buy era. Many vendors didn’t want to sell to the group leaders directly, so we had to build a warehouse to buy a lot of products from the vendors. We acted as the supplier to many of the group leaders. This already made us into the warehousing and delivery side of things. We also learned that people were willing to wait for great products that were hard to find. This gave us the confidence to not do same-day delivery or on-demand.

Obviously, we had to ask what were these products that people were willing to wait for:

It’s usually the products that are hard to find even at Asian supermarkets. For example, super fresh fish, very fresh produce, and fruits. In the early days of group buying, the Pacific Black Cod was very popular. People were buying pork bellies together because they were not easy to find in mainstream supermarkets. During winter time, a lot of Chinese immigrants make sausages themselves, so they buy a lot of pork bellies. 

One of our most popular items was Kyoho grapes. Kyoho grapes are not always available in Asian supermarkets. Additionally, Asian supermarkets have issues with consistent quality, the range of products, and the fact that a lot of people live far away from those supermarkets. That’s why those kinds of products were very attractive. During the group buy days, we would never do tofu, soy sauce, or green onions. Those kinds of products were not considered exciting for group buys. So we only would do, like I said, super fresh seafood or produce or restaurant food or things not so readily available.

The Business of Weee!

One of the big ongoing initiatives at Weee! is adding storefronts for more ethnicities, complete with their own goods. We asked Larry what opportunities and challenges they’ve experienced expanding into more ethnicities:

All of them are very underserved, which makes our business very attractive to all these ethnicities. If you look at U.S. history, there was a very important piece of legislation passed by Congress called the Immigration Act of 1965. It really started this whole demographic shift in this country. It’s a once-in-a-century shift. That’s when the Asian and Latino populations started to grow in the U.S. Right now, if you look at the Chinese population, five to six million people in the U.S., this group is still quite small, less than two percent of the U.S. population, so it’s very hard for mainstream supermarkets to try to serve the specific needs of Chinese Americans. It doesn’t make sense for them to focus on this two percent of the population and try to bring in thousands of products to serve them. That gave opportunities for offline Chinese supermarkets, but the offline model is not the ideal model to serve low-density populations. That’s why there aren’t that many such stores. 

Ranch 99 is the biggest Chinese supermarket chain. The biggest Korean chain is H Mart. It took them more than 40 years to build less than 100 stores. The reason is that the population density is not high enough for them to build thousands of stores. All the mainstream supermarkets have thousands of stores. But these ethnic ones can never achieve that, which means they will always be more inconvenient to access. And that’s physics. You just can’t have that many stores when the population is so low. The good thing for our business is that our model is a better model. You don’t have to drive to us, we deliver to you. We have very large warehouses and we can cover a very wide range. Another big advantage for us is that we can be authentic to multiple ethnicities. An offline Chinese supermarket can never be an Indian supermarket at the same time. An offline Korean supermarket can never be a Filipino supermarket at the same time. No matter how you design this, it’s impossible. But online, you go to us, the first thing we ask you to do is choose the store. You choose the Filipino store, it’s all Filipino. You choose the Vietnamese store, it’s all Vietnamese. We can really be authentic to multiple ethnicities, and that can only be done online.

One thing that caught our attention was Larry’s point about how sparse populations inhibit additional stores which inhibit accessible stores, which would make more people turn to online stores such as Weee! We were curious if the converse was true, whether or not customers use Weee! less in Asian-dense areas where there are accessible in-person stores, like in cities such as Cupertino, CA:

That’s actually not the case. We actually have a lot of customers in Cupertino. Here’s the reason: our assortment is not the same as offline Asian supermarkets. A lot of things we carry, they don’t carry, and a lot of things we carry consistently, they don’t carry consistently. The assortment of items is differentiated. We also have a third-party marketplace. Right now, we have more than 50,000 third-party marketplace products on Weee!, these are all products that brick-and-mortar stores don’t carry. We have sellers in Japan, Korea, and China. Some other sellers are local restaurants and local bakeries. For example, on Weee! you can buy a local bakery product at the same price you would pay in the local bakery, and that is just not available in other apps. You can go to DoorDash, you buy the same product, you pay 40 percent more, 50 percent more depending on what’s your total order value. We have a lot of products that actually aren’t available from Asian supermarkets. In fact, we have slightly better prices than Asian supermarkets because our supply chain is more efficient. Even if you live in Cupertino, we have a better selection and prices. Plus, you don’t have to go out. You don’t have to spend your entire Saturday afternoon grocery shopping. You have better things to do. I’m not saying offline supermarkets shouldn’t exist. That’s not what I mean. We actually don’t see them as competitors. I think that they will exist for a long time and a lot of people like shopping offline. That’s totally fine. We just try to serve underserved communities and we believe we have better products and services than anyone in the marketplace.

A common customer behavior in Asia that hasn’t quite made it to the US is browsing online stores. For instance, most people who go on Amazon already know what they want to buy and only search for that, you generally don’t wander a disparate tab and scroll through those listings. Given that Weee! targets people from Asia, we asked if Larry has noticed such behavior on Weee!

Our customers tend to browse more. With our design, we actually want people to browse more. There’s a common belief that grocery shopping is boring and repetitive. Almost every single website prominently features a ‘buy again’ option. Amazon does that because it makes sense. If you think of shopping as a chore, then it’s logical. However, we see grocery shopping, especially for immigrants, as an opportunity to discover exciting new things that they may not even know exist in the U.S. We always try to create that excitement. That’s why we want people to browse. These exciting products are also important for our user acquisition strategy. People tend to tell their friends about the exciting things they find on our site. If you buy things from Amazon or Safeway, you probably won’t tell your friends about it because it’s the same old thing. But our customers actually tell their friends a lot after they buy something from us because we offer a lot of exciting products.

For our readers (and ourselves!), we asked Larry for examples of some of these exciting products on Weee!:

Nowadays, we’re really strong at seasonal fruits. We really care about flavor because our customers do too. We carry things like the Ori Mandarin from Israel, which is very tasty. Our dragon fruits and coconuts are super popular. In fact, we’re America’s largest retailer of fresh coconuts.

It’s fascinating because this ties in with our multi-ethnicity strategy. We have a lot of customers from different ethnicities. People from Vietnam, China, the Philippines, Southeast Asia, and India all consume coconuts. We are the only place that aggregates so much demand for coconuts and our price is unbeatable. For instance, if you go to Whole Foods, a coconut costs $4.99 each. If you buy on Weee!, it’s $14 for nine. It’s the best price on the market and our volume is really big. We’re also strong in fruits, vegetables, and hot pot-related products. We have all kinds of sliced meat, lamb, beef, pork, and different sauces and vegetables.

Larry’s Personal Growth

Although Weee! is not Larry’s first venture (he did some dropshipping previously), it is the first business he has scaled. As such, we asked him about his process of learning how to be a leader:

It was not very natural. It was a very steep learning curve for me. I managed like two people before I started Weee! at my previous company where I worked in finance. So I had very limited management experience, but as a founder CEO, you just have to learn everything on the fly. Not just managing people, but also how to raise money, how to come up with business strategies, and how to communicate the strategies to your team. 

I read a lot of books. I like to read. So I guess I had some knowledge on paper. This was my opportunity to apply that knowledge to the real world. I also reflect a lot. I’m a huge believer in deliberate practice. So I think I approached the job as something I need to really break down into different areas. For each area, I try to have some mechanism to get feedback and to check whether I did well or not so well. One of the reasons I was really attracted to retail is because retail gives you a very fast feedback loop. If you do a B2B business or pharmaceutical, it can take years for you to get the feedback. But in retail, if you do something right, you can literally see the results in minutes.

Also, I later realized that my finance background gave me an unusual habit. I try to forecast everything. For a lot of people, if you ask them about their strategy, they can’t tell you the impact of that strategy. I think forecasting is important because it requires understanding the mechanism between the input and the output. It also gives you the chance to constantly compare your expectations to the actuals, allowing you to fine-tune your understanding of the business. That feedback is very beneficial for improvement. 

I also hired really good people and learned from them. Our COO is very experienced. When she joined us, she managed teams with hundreds of people. I learned a lot from her. A lot of our management practice is what she brought to us. It’s really a combination of learning from experienced leaders and your own curiosity to constantly get better, to seek feedback, and just a lot of hard work.

We followed up by asking Larry if wished that he had done anything differently in his journey:

I think everything that happened was necessary. If I went back and told myself 10 years ago the things I know today, I still wouldn’t learn from my own advice. There are so many management books, and so many wise people out there. They give talks. Can you really learn from that? Even this conversation, can you really learn from this? I don’t think so. I think it’s just one piece of information. When I read a book now, I see it as one data point, one piece of information. I have to actually do it or be in the process of doing it, then revisit the concept I learned on paper and try to connect that concept to my real experience to make it part of my own. But without the doing part, the information is just a piece of information, nothing more. I could go back and tell myself a lot of things, but it wouldn’t help me 10 years before.

I have the habit of reading certain books over and over again at different stages of my life. For example, one of my favorite books is Sam Walton’s autobiography, “Made in America”. It’s very interesting. Throughout my journey, every time I read it, I pick up different things. The book didn’t change, I changed. A lot of things I didn’t understand before, but now I can understand because my experience grew. Sam Walton, I think when he wrote the book, he was diagnosed with cancer already. He probably gave everything he knew and put it in the book, but unfortunately, most people don’t understand all those things. They have to experience it and then they can relate to that. That’s why I think reading a really good book over and over again is a good idea.

I had heard Larry talk about Sam Walton in other interviews before so I figured that Walton must be one of Larry’s favorite entrepreneurs. We asked Larry what draws him to Sam Walton:

There are a few things I really admire about him. Firstly, in his whole life, he only did this one thing. He started Walmart and then he just stuck to it. He spent his whole life working on that. I’m attracted to that kind of entrepreneur. I’m not attracted to so-called serial entrepreneurs. I admire people who just try to do one thing super well, the best in the world. Also, he’s kind of an underdog. He was in Arkansas, a Midwest town. For a long time, Walmart only served towns with less than 5,000 people. It’s like how we at Weee! focus on serving minorities.  But he, as an underdog, built a business against all the odds. He started in the late 40s, and early 50s. His company went public around 1980. It took him 30 years to bring the company public. But even going public was just the beginning. In the next 20 years, I think Walmart’s stock price grew like a thousand times. Now, I think it has the most revenue out of any U.S. company. He was the richest man in America, but he lived a very simple life. His values very much match my values. So, I do see the parallels with us. If you read his book, you will love him. He’s very simple. I like a simple life. I don’t want things to be so complicated. Just figure out one thing you want to do, and then go for it and spend the rest of your life pursuing it. 

Asian Representation and Identity

Given that Weee! is the largest platform selling ethnic foods, we asked Larry how he sees Weee!’s role in enhancing the representation of ethnic food in the broader American landscape: 

We actually have a lot of mainstream users, and they’re growing very rapidly. We are the top seller on TikTok Shop in the U.S. in the food and beverage category. Almost all our customers on TikTok are mainstream Americans. I think it’s a less intimidating way to shop for products from another ethnicity if you do it online. Let’s say it’s a Middle Eastern store. You just want this one thing, you really like the lamb, what do you have to do? You have to drive to the store, go in, and it’s very unfamiliar. The barrier for mainstream Americans to try Asian supermarkets is a lot higher if they try to do it offline. It’s a lot lower if they do it online.

Personally, I found this extremely insightful as I had never thought of that. When you go to ethnic grocers such as Ranch 99, the store employees sometimes don’t speak very much English. I never thought much of it since I can speak the language, but I can see how the experience could be a lot more intimidating than buying online. For our next question, we asked Larry how being an Asian immigrant has impacted your founder journey:

I’m a first-generation immigrant. I came to the U.S. 20 years ago. My experience really put me in the position to do this business. That’s why I want to be like Sam Walton. I think this is almost a perfect business for me, and I want to keep doing it for as long as I can. There are so many smart people in the world, but what you can accomplish has a lot to do with what position you are in to see and recognize a great opportunity. I just felt like I was at the right place at the right time and I had the right experience and I met the right people. I owe everything to my background as an Asian immigrant to do this business. There were a lot of challenges in the early days. It was very difficult to raise money because people in the VC industry, the mainstream investors, didn’t really understand this opportunity. They couldn’t relate to it. But we were lucky enough to find Asian partners from those investment firms in every round of financing. I think I counted eight or nine rounds. In every single round, there was at least one Asian partner in the deal. They understood what we were trying to do.

Shoutouts

If you ever find yourself looking for Asian groceries, please consider joining millions of other users and trying out Weee! You can order on the web at https://www.sayweee.com/en or through the app, which you can download from all major app stores.

Weee! is also looking to grow their exceptional team across all functions. If you would like to work at the fastest-growing ethnic e-grocer, please check out their available job openings at https://www.sayweee.com/company/careers.

Thank you Larry for joining us!

Stories

Creators Podcast: Chef Priyanka Naik Makes Waves in Vegan Cooking

AHN and Meta Prosper have partnered on a new podcast series highlighting API creators. Meta Prosper is dedicated to amplifying and supporting the API community and driving economic growth and equitable representation. The Creators Podcast series delivers stories on how creators achieved success and created impact through their platforms, serving as an inspiration for the community.

In the first installment of the Creators Podcast series, we shine a spotlight on Priyanka Naik, a first-generation Indian-American whose path took her from pre-med and economics to a career in media and tech, before going full-time into the culinary world.

Priyanka Naik is a self-taught award-winning vegan chef who grew up in New York, incorporating her family heritage into her plant-based cooking. But she didn’t stop there.


Drawing inspiration from her travels to over forty countries, Priyanka infuses each place she visited into her recipes while focusing on sustainability. She practices no-waste cooking and consciously sources ingredients to minimize her environmental impact, making her a leading advocate for eco-friendly culinary practices. 

Priyanka’s cooking skills have landed her on TV shows like The Today Show and The Kelly Clarkson Show, and have led her to become a Food Network champion, TV host, author of The Modern Tiffin, columnist for Ecokitchen in The Washington Post, pop-up restaurateur, and a TEDx speaker.

Listen to The Creators Podcast featuring Priyanka Naik here.

CONNECT WITH CHEF PRIYANKA NAIK

Instagram: @chefpriyanka

Facebook: Chef Priyanka Naik

Threads: @chefpriyanka

Anna Fang

Awaken* newsletter

Candid Conversations on Venture Capital and Entrepreneurship with Anna Fang

Anna Fang is the CEO of ZhenFund, an early-stage venture fund that has invested in over 600 startup companies, particularly in e-commerce and AI, with successful investments in unicorns like RED (XiaoHongShu), Perfect Diary, and Horizon Robotics. Anna began her career in investment banking at JPMorgan in New York City and later helped expand M&A efforts at GE China before joining ZhenFund in 2011.

In a recent interview with AHN Ventures, Anna shared insights about her venture capital journey, the high standards ZhenFund maintains for selecting founders, and the evolving landscape of early-stage investments. Read through to learn more:

HanYue: What inspired you to start Zhen Fund?

Anna: I began building Zhen Fund in 2011 after a significant tenure at GE. The catalyst was a conversation with a Graduate School of Business friend who was with Sequoia China about initiating a Y Combinator-like model in China. During this period, I met Mr. Xiaoping Xu, whose vision was truly inspiring. Additionally, the vast opportunities in China’s entrepreneurial landscape were too compelling to ignore.

HanYue: You are one of the pioneers in China’s venture capital industry. How has being an investor changed over the years?

Anna: Ten years ago, being a VC wasn’t as glamorous as being a private equity or angel investor. The scene was quieter. Entrepreneurship wasn’t as trendy, so it was easier to find thoughtful, high-caliber founders. Our first fund was $15 million, and we made 16 investments, including Xiao Hong Shu, which topped lifestyle app charts, and Huobi, HTX, which became China’s largest crypto exchange, and Deeplint, which went public. The VC scene entered a hype cycle from 2014 to 2020, with an overwhelming amount of money chasing deals. It felt wasteful to me. Now, with a ‘VC winter,’ I appreciate the slower pace that allows for more selective investments.

HanYue: Can you discuss the high standards Zhen Fund maintains when selecting founders?

Anna: There’s a high bar, especially for AI nowadays. Founders must deeply understand the technology. For example, we invested in Zhilin Yang, a renowned and famous PhD.  Zhilin Yang is the founder of Moonshot AI, with a ChatGPT-like product Kimmy Chat.When I was looking for interns, there are kids these days who would say ‘whoa, you invested in Dr. Yang? That’s so cool. I want to work for you.’ Interns want to work for us because we invested in Yang, that was really something special.

HanYue: Yodu achieved many significant successes with your first fund. What excites you currently?

Anna: Lately, I’m fascinated by AGI and the global integration of foundational models into robotics. There’s also a burgeoning interest in applications built on these models, alongside video and productivity apps like monaco.im and max.me. Observing how human and AI co-pilots can coexist and interact is particularly intriguing.

HanYue: You’ve invested in many successful founders. What traits do they share?

Anna: It all boils down to hustle – your organization’s name Asian Hustle Network really speaks volume by the way. Successful founders are not afraid to get out there and continue to network. They have an infectious enthusiasm. Even I had to do it once. When I was just getting started, I would put ‘send me deals’ directly in my email signature.

HanYue: What challenges do early-stage startups typically face, and what advice do you have for navigating these challenges?

Anna: All successful companies have experienced moments where they almost didn’t survive, be it due to regulatory issues, cash flow problems, or founder conflicts. My advice is not to be phased by difficulties. Believe that you will pull through. Having mentorship is also crucial as it provides support and helps solve problems together.

One thing I really love about angel investing is the thrill of being the first to adopt new and innovative ideas, always staying alert and aware of emerging trends. Emma and I often joke about not being the top students at Stanford, always admiring how incredibly smart our classmates are. 

Bob taught me the essentials: reviewing the team page – I often feel like an admissions officer searching for predictors of future success. It’s like trying to find Yao Ming among a crowd of tall people—a search for standout talent in a field of strong contenders. 

With everything changing so fast, I am more excited about looking for really thoughtful founders. For example, I am really excited about this one young man, who used to my intern, he could just sit there and talk about the macroeconomy trends forever. And the way he thinks about what might become popular among young people continues to impress me. For example: The younger generation embraces ‘YOLO’—living in the present. And as a founder, you will need to think about new hobbies and cultural shifts that might emerge, and find ways to take advantage of that. 

HanYue: As a lecturer at GSB and a seasoned investor, how do you differentiate in a crowded VC landscape?

Anna: Our differentiation lies in our founder-first approach and our simplified, transparent investment process. Even when we pass on an investment, we provide thoughtful feedback. Zhen Fund is not just about funding; it’s about fostering a community and offering programs like the EIR and Ostrich Club that systematically identify and support potential top founders. We want to build a supportive community. 

Edwin: What trends from China do you see influencing the US, and vice versa?

Anna: E-commerce platforms like Shein and Temu are leading trends, with TikTok’s integration of e-commerce being particularly noteworthy. We’re also seeing interest in replicating China’s online education model and infrastructure globally. Additionally, attempts to mimic the success of businesses like Luckin Coffee in various international markets highlight the growing influence of Chinese business models abroad.