Author: nancyhua

When I stepped down as CEO in 2018, I wrote a post mortem and shared it privately with founder friends who directly asked when I blogged here. The company got acquired in 2019 and now I’m sharing the post mortem publicly because readers told me they saw novel concepts in my document they hadn’t heard elsewhere (as I write this I wonder if it’s because I was wrong. LMK!).

I used to abhor failure, but publicly releasing this post mortem no longer holds charge for me. Through Apptimize, I’ve learned and changed such that my subsequent companies will be very different. One of my biggest learnings is that I’d played a finite game and missed the infinite game. I didn’t know those concepts at the time and saw “product innovation” as a separate category of work. After shifting my reference frame, I now know innovation as a sign of infinite game behavior. Anyway, I hope the below is useful to founders whose sales motions aren’t getting easier years into their venture backed company and want to consider frameworks for evaluating their position. 

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Startup Post Mortem, written Q3 2018

At times, the company we founded in 2013 seemed to be doing well by various objective metrics— we had a prestigious customers list ranging from CNN to Comcast, we raised 3 funding rounds summing to over $20MM in venture capital investment, and our revenue grew exponentially for the first few years (obviously easier to 3x when x is small). As the cofounder and CEO, I always bet on our ability to figure it out and be a financial success. I put in the first $50K and bought our domain for an additional $10K, which isn’t much money in the scheme of startup funding, but this was before we had users, before we’d gotten into Y Combinator, before it was anyone other than me and my cofounder. I used to be a trader, so I wasn’t goofing around— I fully expected to eventually make tons of money off our startup. I wrote a draft S-1 for how we would IPO, I didn’t pay myself for the first year, I was the lowest paid person in the company for years, and I guarded our equity like it was the blood of my children. I always wanted more equity because I valued it so highly. When founder friends told me to pay myself more, I asked for more equity instead. When we raised an oversubscribed Series B, founder friends told me to ask if I could sell some of my shares or take money off the table, but again I asked for more equity instead. Suggestions to get cash seemed ridiculous to me because I didn’t think I deserved cash yet; we weren’t a success and I, more than anyone, knew all our warts. When we were getting acquired, founder friends suggested I block the acquisition unless I made money off it, but that also sounded ridiculous to me because I felt I deserved money least of all. I’m sure my VC’s would’ve agreed.

Our company didn’t exit at anywhere near as well as I’d pitched, and I felt sad to fail after so many years of everyone working so hard. For years, we worked weekends and holidays, regularly in the office till 10pm. My VP of marketing was back at work weeks after birthing each of her babies, working through her pregnancies, and we forced anyone who entered my house or office to do user tests. Had it all been a waste? Should we have spent that time partying instead? Being successful is important to me and I felt ashamed my company wasn’t a financial success despite how hard everyone worked on it and how much money we raised. Sure, I could twist the story to make it sound like a success in terms of learning and building, and we made a product people used, and we got acquired, but the fact is that the company didn’t make money the way I’d imagined and pitched. I felt scared my investors would view me as a failure and dislike me or view me as incompetent. We should’ve done better— we had some of the smartest people you’d ever meet working on this problem that I convinced them was important enough to warrant their time and resources. How had I been so wrong about the financial outcome? 

Two Key Qualifying Questions:

One of my investors put it well: everyone in a company is either a) making the product or b) selling the product. I learned there were 2 key questions that separated successful vs unsuccessful hires in our company:

1. How hard is it to make this product?
2. How hard is it to sell this product?

Our product was both hard to make and hard to sell. What do I mean by this and how does this impact the hiring profile?

Product vs Sales Driven Company:

On the spectrum of how hard it is to build a product, web forms are on the easier side. Easy products are anything that a person could do with a series of google docs and sheets, anything that you’re 100% sure is possible to make. On the harder side, there are products like a rocket or a flying car, where it’s <100% guaranteed the engineering will get there in the time required. If the product is easy to build, then engineering is easier and it’s more on the sales and marketing teams to drive the company forward and show why your company is better even though others can make this commoditizable product (through network effect/ better land grab execution, brand/ trust, integrations/ partnerships, “thought leadership,” customer service/ support, etc). 

In contrast, the harder a product is to build, the better engineers you need and the more everything depends on the product team shipping something 10x better. 

Our product was nowhere as hard to build as a rocket, but it was harder than a webapp, and we made design choices that increased the difficulty of building and maintaining our product in exchange for gaining competitive advantage, which was high at one point but eroded. This means our company had to be product driven. But after the first few years, we failed to be product driven because 1) I struggled to hire product leadership that was technical enough and 2) I was short term focused on revenue goals. Single-threaded on sales, I didn’t focus on the product roadmap because all I cared about were short term goals to lead us to the next funding round because I was mainly driven by my fear of the startup failing versus any love for shipping a better product. 

Transactional vs. Consultative Sales:

Everyone in B2B SaaS knows from SaaStr etc you’re supposed to distinguish between sales people who sold to technical vs non-technical teams, and differentiate sales candidates based on the price point they were comfortable selling at, but I learned an additional point of differentiation: how consultative must the sale be? On the spectrum of how hard it is to sell a product, widgets like video conferencing software are on the easier end, easy to explain and demo. On the harder end, there’s consulting services to suggest TBD process improvements. Even harder is stuff that’s a new category where you have to educate the buyer on the need. The hardest sales require founders to drive sales; the salesperson needs to be at least as smart as the buyer so they can credibly educate the buyer on how the product will urgently impact their revenue. Buyers of video conferencing software don’t expect to get promoted because they chose Zoom over Webex or talk about the impact of their choice at a conference, but buyers of analytics software do want to hear how they’re going to become Chief Product Officer vs VP, that they’re going to show their CEO a powerpoint with graphs clearly illustrating the revenue their analytics choices have created for their team, and how they’re going to speak at the conference on their data driven decision making processes.

If the product fulfills a clear, established need, you can hire a wider variety of salespeople. But when the product’s harder to sell, you need a “consultative” salesperson, a specific profile correlated but distinct from price point. When the product differences/ usage/ impact are hard to explain, or there’s no category yet, or it’s not a drastic, budgeted need, you need sales people who are like consultants, subject matter experts who are smarter than the buyers. 

If the sales person is interested in presenting a custom, strategic overview of how our product impacts the buyer’s product strategy, they eventually want to become customer success managers. Other than our first business hire, who was more like a cofounder to me and eventually founded his own company, I couldn’t get anyone to do both sales and customer success at the same time. I think our deals weren’t big enough and our customer success process was in the awkward gap between easy and hard— not hard enough to warrant consulting services, but not easy enough to remain a yearly check-in to upgrade the account. 

Fear/ Ego:

Shifting gears from the tactical company building stuff to the touchy feely, the following section is philosophical.

It had started out really fun. In the 2nd year of the company, one executive told me that she got all her social fulfillment from our work. We were always together, working from my house on weekends, engineers sleeping over when they got tired, cooking together, talking about each other’s love languages, a group of friends going on an adventure together. 

But now I see that I didn’t start the company with a pure heart. I started the company because I thought it’d be successful and I wanted to prove I could contribute something to the world, not because I specifically cared about our product or market, which I learned matters for me as time passes. 

I thought I could get passionate about anything, and that was true at first, but it drained me to force myself to be an expert on our product for years because it wasn’t something I would’ve done if it weren’t for the company, the team, and my ego. For years, I always knew the most about our market and would send links to the rest of the team for news that had come out, anything they needed to know. I’d talk with all the CEO’s in our industry and obsess over competitive intelligence. But I didn’t enjoy it for the sake of it— I did it because I felt responsible for everybody and didn’t think anyone else could be held responsible for anything. 

Over time, I learned that my energy was the limiting reactant to much of the company’s forward progress, so I had to focus on what would energize me and manage my own energy. I learned that I do best when something is new because I’m intrinsically interested in learning new things. But after a project gets going, I can only continue gaining energy from the project if it’s something I’m intrinsically interested in, if it’s something I’d work on even if no one knew about it or if I never got any reward for it. 

It took me years to admit I wanted to stop being CEO because I was scared the company would die if I stopped. I wanted to quit, but I view myself as a strong, successful person who doesn’t give up and always figures it out. When I started thinking it wasn’t fun anymore, I thought about how I should be grateful for my amazing life, and a lot of the time it was still fun… I made excuses and suppressed my “weak” or “useless” feelings. When I wanted to give up, I’d listen to Ben Horowitz’s writing on “the struggle” and think about how it was supposed to be hard; I was supposed to not have fun— otherwise everyone would be a billionaire. It took me time to peel back my ego so I could admit my true feelings. 

Those are the only regrets I have, times when I didn’t listen to myself. All the strategic and tactical mistakes, I don’t regret those because I did the best I could. But when I knew that it wasn’t what I wanted but went along with it— I regret that because I wasn’t true to myself and I knew better. 

I was scared to tell anyone I wanted to leave because I was scared of what would happen. I think it’s a rare company where people are vulnerable about their thoughts around leaving, especially if they’re founders or executives, because it’s scary to lose control. We hide our emotions because we want to control peoples’ potential reactions to us. I had lots of justifiable reasons for not admitting even to myself that I wanted to leave. I was scared everyone would leave if they heard I wanted to leave, I didn’t want to burden them with something they couldn’t affect anyway, it’d distract them needlessly from their work. I learned that if I don’t figure out how to be vulnerable with my team, I can’t build the culture I want.  

For years, I tried to shield my team from investors and my desire to leave because I thought they couldn’t handle it and I wanted to control them. I thought if I focused them on their goals, everything would be fine. This was not fun for me because it was lonely, but I didn’t know another way to operate. I made sure to be reasonable and had a slew of advisors and executive coaches validating my choices, but my conventionally justifiable managerial moves weren’t authentic to me. 

At various points during the CEO hiring process, I told my board members I didn’t care about staying CEO, but I don’t think they believed me and assumed I was ego attached to the title or role. This was false. I told them, “Ideally, I would do no work, and people would still give me money,” but I didn’t believe this was possible. Rather than the role or title, the thing I was actually ego attached to was the company being successful, which I was sure was tied to me being CEO even though I didn’t want to be anymore— that’s a different kind of hubris/ ego attachment. 

It wasn’t until I hired an amazing executive team that was smarter than me (V1 of my exec team was also smarter than me but I didn’t trust our inexperience so I messed up that team) that I felt ready to stop trying to manage their emotions and admitted the truth to myself and to them. It was futile to try to control them because I needed their help. I was tired after 6 years of running the company and was no longer too proud to admit my needs. I realized my ego was keeping me from my true desires because all my ego cared about was my image, looking like a success, when inside I wanted to be more playful. For years, my ego kept me doing something I thought I “should” do, when I didn’t want it anymore.

Market Size, Product Market Fit, Raising Venture Capital:

This section is relevant if you are raising venture capital. Unlike VC-backed startups, bootstrapped companies are not as reliant on growth. A profitable small business might have zero competitive advantage and never think about building moats or expanding outside of a tiny niche and still be making bank for its owners. In contrast, VC-backed startups need to grow at all costs to be worth it.

VC’s always ask about market size and competition, and I had a reasonable answer for this. Our market size was small but growing. We would expand out of this market through new products on our roadmap. The thing we didn’t realize is that we needed to be a product driven company, and we weren’t anymore. After the Series A, I focused on hitting quarterly sales goals and we all believed we could do that without product innovation or market expansion, because product only impacts things longer term. Driven mainly by fear of failure, I was not thinking longer term than the next funding round and board meetings were lasered in on short term quarterly targets. 

However, in a small/ developing market, you can’t hit the next sales goal by pouring money into marketing. Our market wasn’t so small that we couldn’t hit our next sales goal with our existing products, but it was small enough that increasing costs on sales and marketing didn’t get us anywhere. The “gas on the flame” model is what everyone assumed we should follow, and it’s what you basically have to follow if you want to grow exponentially in the way the VC model demands. If the market is large enough, then pushing additional marketing dollars into it gets you more leads for longer, but if the market is small, additional money stops working too fast. In that situation, strategies that work for big markets don’t work for a small but growing market because it’s not just a matter of more marketing dollars, automation, or SDR’s. We tried these things, and frustrated a bunch of SDR’s and marketers who thought it’d be easy but then realize they couldn’t hit the goals they’d set for themselves. When people are scared to miss goals, they want to blame the other legs of the org, leadership, etc. 

We always pitched that we’d expand out of our market, and this is plausible and what we attempted to do, but we didn’t do it successfully. Although our core product was still the best, it was no longer 10x better. We had to come up with another product but we were already a company with an established product that was hard to maintain, and the magic that came with the first versions of the product wasn’t in our DNA anymore. Only a few people on the team even still remembered the days when we’d release mind blowing features that were obviously patentable, made our customers say, “Wait, how did you do that?” and force our competitors to freak out and start rewriting everything.

I don’t think the VC’s ever thought we had a product issue because:

1. At our stage and revenue, VC’s were used to the product being fairly well baked with a pretty obvious roadmap. 
2. SaaS VC’s are finance focused because SaaS has so many metrics to fixate on and it’s easier to fiddle with the arithmetic of the funnel conversion rates and CAC and so forth than to look at the product. 
3. My MIT background implies I should be the product visionary so they trusted I was dealing with it. Sadly, this was not happening.
4. Everyone they talked to, including product VP’s who came to interview customers and assess our issues, would talk about how our product was the best. “Best” is a squishy concept and not good enough to solve our issues. 
5. The VC’s who passed because of market size were sort of right, and we were with the VC’s who didn’t believe it was too small and could keep going with the existing product.

TLDR: we weren’t focused on product innovation because, after raising a Series B, you’re supposed to be in scale mode, not majorly reconfiguring product market fit to try to grow at the rate required. But we couldn’t scale sales for a small market in a Series B way. We should’ve been in product development mode, but my Series B focus was all on quarterly sales goals, so we poured money into sales with little effect while chugging along half heartedly on product. 

I wanted to make my VP of Product CEO because he is amazing at product and strategy and leadership, but neither of us thought anyone else would support this because the board thought my inexperience was the problem, not product, so someone with zero CEO experience would’ve been the opposite of what they prescribed. If I’d had more energy and courage, I would’ve fought to make him CEO anyway and told him I would’ve had his back and helped him run everything, but I was tired, unsure of myself, and didn’t want to get blamed if we failed, which was very possible even with the best CEO ever, so I went the conventional choice that no one would blame me for and that everyone else wanted: an experienced, sales oriented CEO (I also have post mortem notes on what it was like as a board member with an outside-hire CEO, but that’ll be relevant to fewer founders so I’ll only share that if enough people care). We’ll never be able to run the experiment of what would’ve happened if I’d made my VP of Product the CEO, but in the future I can trust myself and stick to my gut vs going with popular opinion.

There were other VC-backed companies we were competing with, and that fueled the high cost, land grab mentality. We could’ve operated profitably, grown more slowly, returned money to investors, and become a small business until we were ready to scale at a VC rate, but all of us were on board for something higher growth and weren’t interested in this path. 

In my mind, I wanted to get us to the next funding round so I could leave and thought there was no way we could hire a CEO who wouldn’t kill the company until I fixed xyz first. I didn’t see that my mentality made it so there were always more things to fix before I could leave. I always found fundraising from VC’s way easier than making it from customers, plus that’s what competitors were doing, plus so many random SaaS companies with easy products that were basically webapps that I could make in 5 minutes using google forms were raising tons of money (our product was way harder to make and so much more advanced!) so I didn’t think twice about the potential strategic obligations of raising more venture. 

Lastly, Hiring:

As a leader, if you suck at hiring, you suck at everything. For example, if you’re bad at hiring, you’re scared to fire underperformers because you’re scared you won’t be able to backfill them in time, so now you’re making excuses about how you’ll fire underperformers after you already have someone else in place, which is increasingly awkward the more senior the role is because now you’re secretly interviewing for replacements. Being great at hiring means sourcing, which means getting really clear on the criteria. It took us a few iterations to get the criteria right because we learned there was a lot we had taken for granted when we put together the initial scorecards. 

I read many books on hiring and had overqualified hiring committees of top executives interviewing each candidate, but we still made mistakes. The biggest learning I had was that experience is much less important than the candidate having a growth mindset and the drive to learn. The deal with experienced candidates is that they will do whatever has made them successful in the past. This works if you precisely diagnose your problems and know exactly what you need to hit the goal, which is hard to do if it’s your first startup. 

I had never even worked in a business with customers before, so I knew I had blind spots in my ability to assess candidates. But I best knew all the things that actually needed to happen to hit goals and function well at my company because I had experienced it happen. Nevertheless, I didn’t trust myself and overly relied on the hiring committee. 

Hearing experienced candidates tell me with such confidence that they would fix all my problems was so comforting. I deeply wanted to believe them. What did I know anyway? We’ve closed a few million in revenue, but this person has closed a hundred million. I’ve done X at my company for a few years, but they’ve run that function for decades at various, more successful companies. The safe thing seems to be to hire this person so I don’t have to worry about it again. However, I learned these claims were uninformed because there was no way they could understand our issues well enough through an interview process to know how to solve them. Because our product was both not easy to make and not easy to sell, and our market was small, we weren’t just missing the obvious things to do and just hadn’t written the correct playbook or set up the right interviewing process. It worked better to hire people who didn’t know how they would solve our problems but had demonstrated scrappy problem solving abilities in the past. 

After hiring someone who wasn’t going to work, I usually knew within a week because they would still have no clue how anything worked (in contrast, execs like my CEO-level VP of Product was teaching me things about our company and space and writing documentation within a week). But I’d fear I was wrong or inadvertently creating a self fulfilling prophecy by not supporting them enough. Thus I’d let them hire people and stay out of their way, but ultimately the original team would leave and the new team wouldn’t be hitting goals, and we’d be left worse off than before. It’s better to make the tough call right away and admit you mishired, even at the cost of all the time invested and the team initially being excited and having to pay the recruiters, but it took me time to gain the confidence to do this, to trust myself and thus earn my team’s trust. 

Hiring experienced candidates worked if I knew exactly what I wanted, which I came to trust more over the years. Then all you need is to get confidence the candidate can do it for you because they’ve done it before themselves. References corroborated whether they were instrumental versus “around” at a hot company growing irrespective of their involvement. But you have to make sure the problem isn’t going to change from that diagnosis, and that the candidate is self aware about their strengths and weaknesses. The candidate has to get comfortable that their experience aligns with the diagnosed issue and that if the diagnosis changes, they may no longer suit the job. If you aren’t able to precisely diagnose the thing you want them to solve for and what it takes to do it, or if you think the problem will evolve, then hire someone who is more open and willing to grow, even if it means less experience, or experience that’s not as applicable, eg. a different price point, space, or buyer. 

I struggled the most to find good product leadership. Many good product people with remotely technical backgrounds become founders themselves, so it’s a tough role to hire for unless you invest in someone less experienced with a growth mindset who’s willing to join you for a few years so they can learn faster and have a bigger impact. I think this is the deal you often have to make in engineering and product hiring. 

I can see how my hiring mistakes often came from my ego driven fears of failure. I’d forgotten that one of the reasons I’d started a company was because I wanted to choose who I wanted to work with. Now I know I’d rather fail with a team and product I love and learn together with, than to “succeed” with a team and product that isn’t right for me.

Aftermath: 

We started the company in 2013 and, for me, it was fun for 3 years, then un-fun for 3 years, then I spent 2019 distancing myself from it. I wasn’t involved in the acquisition conversations, nor did I go with the team and product upon acquisition. 

I wish I were better able to show my appreciation for everyone. I felt guilty my company was an expensive learning experience for me. I don’t think any other experience would’ve been challenging enough to force me to change because I’d always gotten what I’d wanted before— my standard operating procedure of being smarter and harder working than anyone has always been enough when it came to the types of things I was pursuing. But this challenge was what I needed to force myself to confront my blind spots. I had never worked so hard at something and had it fail like this. I definitely gained tactical skills with regard to everything from executive hiring to enterprise sales, but ultimately I learned about my own psychology. 

Isn’t it always about people? I still feel haunted by the people I fired who feel unjustly treated, and my investors who saw me fail. Simultaneously, I feel awed by everyone who worked for the company because I saw how much people gave, and how everyone stepped up when I felt useless. Ultimately big takeaways devolves into platitudes, but the parts I loved the most were the relationships. Our customers became my friends and allies and, as far as I know, our product is still alive at the acquiring company. When I started the company, I didn’t know what it meant to have full partners in the business who I utterly trusted. Now I know what it’s like to not have to be alone, what it’s like to be with people smarter than me. My team inspired me and raised the bar. In future companies I start or join, I know what I need out of the team and how to be a better teammate and leader. 

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Reading through the above document I wrote 2 years ago, I appreciate how I’ve gotten to know myself better. Sounds cliche, but self awareness is the ultimate power. Regardless of $ or resources, without self awareness, I’m at the mercy of my thoughts, emotions, sensations, stories, friends, etc, reactionary and subject to un-designed manipulation from random stimuli. As I keep learning about myself and my blindspots/ assumptions, I gain more power to know and act from my true self, vs reacting to what I think will impress others or what sounds like a good idea right now because of this thing I just read or because of my mood.

Now I’m willing to allow my life to be 100% exquisite. I used to fear getting soft if I indulged certain facets of myself. Like, if I got a cat, or had kids, or meditated too much, I might lose my drive and leave a lesser dent in the universe. But now I see that I don’t have to worry about that. Now I trust and know myself better. The competitive part of me will always be this hyperproductive, demanding, ruthless achiever who constantly strategizes about how to crush every potential threat— I don’t need to worry about not being driven enough; I trust and know it’ll always be there when I want it. The thing to be aware of is whether I’m doing it reflexively versus consciously. That’s all Conscious Leadership, which I constantly talk about. Anyway, for all you founders out there, let me know if I can help. I invested in 2 companies in the last YC batch, Backlot and Known Medicine, because, for me, startups and angel investing are about supporting founders and learning and having fun. I love founders, so let me know if you want to connect.

I’m thankful for COVID because it’s helped me finally love my loneliness. I was in denial about it for years, rejecting loneliness as weak, immature, and painful. I kept myself from feeling it by having a lot of friends, making myself into a busy and important person, and generally repressing such a useless emotion. After all, aren’t we supposed to be zen and totally independent of others? Any kind of neediness is unenlightened and lame, which obviously isn’t me. I’m strong, emotionally stable, and only look towards myself for approval… right?

At T-group, I learned I couldn’t say, “I want people to like me,” without adding in a bunch of qualifiers, like, “but not at the expense of being authentic,” etc. 
Jeff pointed out, ‘Seems like we finally found your edge. You’re scared of admitting, ‘I care about being liked.’” 
“I’m not scared! It’s just not that important to me compared to other stuff.” 

But I wondered, “Why do I keep qualifying that statement? I can say other stuff that I also don’t prioritize without qualifying it. Like, I can say, ‘I like 30 Rock,’ without adding, ‘but not as much as I like, ‘Rick and Morty.’” I saw all the judgments I had about wanting to be liked, wanting others’ approval, needing others. I hid behind my openness— I’m not scared of revealing personal facts or controversial views, so I didn’t have to be vulnerable myself to touch on topics others viewed as edgy. Was there even a difference between openness and vulnerability? Turns out there is— that by definition, being vulnerable means you give someone else some power to affect you. That’s what Jeff had kept pushing me on— what was actually vulnerable for me? Well, it turned out I was scared of admitting that others had power over me. Why would I be so stupid as to invite suffering by giving others any control over my internal state? I wouldn’t do that.

Acceptance is the first step, and I was in denial about wanting to be liked. Who cares what others think, I’m an iconoclast, others’ opinions say more about them than about me, etc! But humans want to be liked. I took a step towards accepting myself as a human— I wanted to be liked, but I didn’t want to care about being liked. 

My fear wasn’t just from my aspiration of being high status and empowered either. It was from being scared of needing someone else for my happiness, and having them reject or fail me. I was scared of heartbreak. Isn’t that logical? Isn’t it clearly more stable to have your emotions depend on nothing you can’t control, including anyone else’s behavior or anything that happens in the outside world? Nice ideal, but I was fooling myself that I’d already gotten there and had skipped all these other steps to enlightenment. It just wasn’t true that I didn’t care what others thought of me.

When I told Simar my life story, I noticed the parts where people left me, and where I left others. My mom abandoned me twice. When I was 2, she came to America without me; I don’t remember but my cousin tells me I cried big, slow, silent tears when she gave me the letter my mom sent. My cousins cried around me, watching me miss my mother, 想妈妈. In college, I wrote about my mother moving out of the house when I was 15 and me not realizing she wasn’t coming back. Until she called to say, “It’s my time now,” and to send her all her things. I’d answered, “That makes sense. I’m fine. I’ll stay by myself; I don’t want to live with Dad.” I didn’t need her. I didn’t need my dad either. When my professor read my writing and said, “She abandoned you,” I was surprised because I’d never thought of it like that. 

I saw the parts of my life when I’ve abandoned people, like the neighborhood kids I left without a word whenever we moved every few years around Pittsburgh, my friend asking, “When did you find out? Why didn’t you tell us you were moving?” and me shrugging. Or my teacher giving me an addressed and stamped envelope so I could mail in my finished story exclaiming she was sorry to be so pushy but she wanted to know what happened to her favorite character Queen Purple, me taking it though I thought it was silly she cared so much. Whenever I’ve been separated from people, I didn’t want to be heartbroken again, I didn’t want it to matter. What was I supposed to do about it? We’d be fine. I was always fine. 

In elementary school, I kept our house key tied around my belt loop with a thick piece of bright red yarn. I’d go outside and play with the neighborhood kids who were all older, and after they were called home for dinner by their parents one by one, I’d go back to our apartment and turn on the TV and lights so it didn’t feel as melancholy and quiet in the twilight. The TV and I would watch each other until my parents came home. At night, men would break bottles and yell across the parking lot. Lying in bed, staring at the yellow from the street lights slanting across my ceiling, I’d sink into the astounding realization that I was me; no one else could ever know the experience of my brain. Lying awake at night, 8 year old Nancy would meditate on this magic: I was alone in my consciousness. 

I thought I was really good at never feeling lonely, but it started to break down when I turned 30. Living in a huge house with my best friends, I felt lonely. My cofounder had left and I told everyone this was the best thing ever, not a big deal, very mutual, but I was scared. I’d told a friend I’d broken up with my boyfriend and he said, “But he’s great! And you guys were together for so long! Wasn’t it already decided that he was the one?” When I told my team, they said, “Oh no! We’ll never see him in our office again,” and I immediately said, “It’s for the best. Long distance wasn’t working and we’re both starting companies. We’ll still be friends. I’m really happy!” I was happy that stuff was happening, and I’m usually cheery and smiley, but I also wasn’t happy. Was I losing my edge? I just had to find a new boyfriend, and work even more, and control my emotions even more. I didn’t find loneliness an attractive emotion in me so I didn’t let myself feel it or acknowledge it. I was disciplined, long term greedy, and good at self denial. Everything was fine.

But I started to do things that surprised my friends. 
“Why are you going out with that guy?” they’d ask about various dates. “You don’t seem happy. I’ve never seen you cry this much.”
“It’s just for fun,” I’d say, illogically. I always had an explanation, or a distracting, funny story about my dating life. I’d wonder, “Am I going crazy because my uterus is aging? Must be more emotional because of hormones. Doesn’t mean anything. Ignore.”
“Are you lonely?”
I protested, “No, I’m great at being alone. I’m single for at least 8 months between relationships. During those times, I focus on work and projects and friends and working out. It’s great!” But I was just white knuckling it during those breaks. I didn’t love it. I was forcing myself to be alone out of pride, to prove to myself I didn’t need anyone, because I didn’t trust myself and felt scared I’d dive into a random relationship too fast, because I liked to take a few months to decompress after relationships, because I didn’t see anyone I liked and the loneliness hadn’t gotten too bad yet.

It wasn’t until I dated someone who I didn’t even like that I was forced to admit I was doing it because I was lonely. My friend said, “You seem to like hanging out with my cat more than your boyfriend.” 
“Your cat is amazing! There’s no one like him.” But I finally let myself wonder what I was really doing. 

Her cat purred against me, rubbing his face against my hands. I loved petting his warm, soft fur. I remembered my old cat, how she pawed and meowed at my bedroom door because any separation was unbearable. It was a sliding door that didn’t always lock properly and she’d sometimes get a wedge open that she could start to thrust her face through. She’d scrape with her little paws tirelessly until finally she’d thump onto my bed in the dead of night. She’d contentedly arrange herself against my skin and start to lick her disheveled fur back into place, sometimes licking me until I couldn’t stand the scratchiness anymore and shifted away. 

I could feel a small cat like her inside me, mournful, yowling, wanting that warmth, that touch. All my life, I kept pushing it back, shoving its face into its box, telling it, “You’re fine, you don’t want that, you’re not here.” But it was there, it was getting louder, it was growing. I starved it but, skeletal, it escaped. A shadow, it lurked and loomed. I deftly ignored it, just an illusion. When it wouldn’t leave, I left it by the side of the road, but it always found me, fur matted and eyes glowing. It was never going to stop until I held it and caressed it all over and set out a bowl of milk for it. 

Before COVID, I had social events every night, often multiple. People told me I was the most social person they knew. I had amazing friends, many of whom had known me more than half my life. Wasn’t it dumb and silly and ungrateful of me to feel lonely? But I fretted that my friends would fall from me as they had families and rightfully prioritized them over me. I distracted myself from this fear through my usual methods. Geniuses asked me out at events, 24 year olds asked me out on the street, I wasn’t lonely, I could date anyone, everything was fine.

But then during COVID, there were no social events for me to feel FOMO about. Friends said I was the only one who was saying I loved COVID. I loved focusing on my art, video chatting with friends, feeling my feelings, and indulging my introvert.

One day, I admitted the loneliness was mine and let it in. After I acknowledged it, loving my loneliness was surprisingly easy. What’s the difference between ignoring it and loving it? It’s dancing with it. It’s feeling it. I savored my loneliness like I savor the delicious twinge of delayed onset muscle soreness. I savored that ache in my heart that wanted someone to love, that was afraid of separation, that missed my ex even though I’d judged him to be “unworthy” and previously would’ve thought I “shouldn’t” miss him. But I did miss him and others, my mom, my friends, my teammates who I would alternately be sure I needed to fire and be terrified would leave, my old cats, all these others in my life who I’ve loved and lost who I “shouldn’t” miss because it was pointless and weak. I let that missing in, I let my heart break, and I massaged that ache and poked it to feel it even more. I played with it and held it until it finally eased, and then I let my heart break anew to see if I could find the ache again. 

I’ve never consciously wanted to date someone just to avoid my loneliness, always saying I could get a pet or a sex robot if that’s all I wanted. But my inner needy cat had been riding me all these years because I’d been unconscious of it. That’s been the meta lesson of CLG: any pattern that you’re aware of you can play with, whereas any pattern you’re not aware of plays you. I don’t want to avoid my loneliness anymore. It doesn’t long term work to avoid it anyway. I have to learn to love it.

I wrote a poem for my friend’s open mic night. https://youtu.be/Q-7pjPsj0dY

“For My Unknown Soulmate: Love in the Time of COVID”

Behold, I ordered all new bedding, because I am ready for YOU
We’re probably both so busy learning achieving and quarantining
I have no idea how we’ll meet
But I hope you’re investing this time in getting ripped 
So you can attract my attention from across the universe
So one day we can take off our masks and 
Nuzzle each others’ naked faces

Even during non-quarantine times 
It was unclear how we’d meet because
I only left my house to go to barry’s bootcamp and eat with friends 1:1
I don’t like live music, sporting events, loud parties, or staying out late
I don’t drink or do drugs except acid
I can count on 1 hand the times I’ve been to a club or a bar for non-business reasons
But now COVID has leveled the playing field for nerds like me!

I love that quarantine has made social interaction rules clear at last, 
That all interactions are on zoom so networkers don’t ask me to coffee
If you’re the same way, we might never meet because
We both stay at home eating, writing, and doing jump squats all day
But I hope we meet because it’d be more fun doing it together
While we snuggle and joke and talk about our readings and writings
And riff off each others’ ideas
And massage each other all over
And make fun of each other
And tell each other stories
And play with everything that happens including COVID

Because I’m a rational person
As a science experiment
I rearranged the romance corner of my house 
According to a feng shui diagram 
So now I leave it to the universe and accept whatever happens

Quarantine has trained me to be zen and love aloneness
But I don’t feel alone bc I feel like we’re in this together
I feel like I’ve always known you so even if we never meet 
You’re out there and you’re with me
I’m with you 
And I’m with me
Quarantine or no quarantine

For the past 6 years, I was scared to openly share my writing because I feared it might somehow “matter,” ie. negatively affect my company or be misconstrued. But in 2019, my company got acquired! Now, I’m a cat of leisure so I can post whatever, starting with these notes on my 2019 and 2020 goals.

I had 3 big goals in 2019: 

1. exit Apptimize (done)
2. finish writing my YA sci-fi novel (not done)
3. go on a date with 1 person monthly with P score of 70%+ (done, although currently single)

Let’s drill in on each goal!

Apptimize learnings: 
I ran Apptimize for 6 years, constantly hero-ing before I became aware that there was another way to operate. After all, who else could possibly be held responsible for anything? Not only was I the founder and CEO, I’d always been the one responsible for everything I wanted my whole life, never viewing my teachers or parents as authority figures, always questioning directives. It wasn’t until the final version of my executive team that I was able to recognize I was working with people who were smarter than me about everything. Then I felt I could stop hero-ing and risk learning what happens when I stop (big thanks to my CEO group).

I wrote a post mortem of my experiences running Apptimize when we hired a new CEO in 2018. I was still technically at the company while he was selling it, but I was figureheading and not part of the acquisition. LMK if you want to see the post mortem bc publicly sharing my failures scares me. That was one of my learnings— I can talk myself into a lot of stuff that I don’t actually want for the sake of wanting to view myself as “successful,” but I don’t want to operate like that anymore. 

My new rule of thumb is to only do stuff that I’d do even if I knew it was likely to fail and if no one knew I was doing it. That eliminates me doing stuff out of ego/ fear/ status. This way I’m only doing stuff for the joy of doing it and not ascribing meaning to whether I achieve my preferred outcome. I’m always going to be an ambitious, driven person, so I don’t need to solve for that part of the equation as long as I’m focused on something I enjoy the process of doing, which brings me to my writing. 

Writing my book: 
Although my 2nd major at MIT was writing, I’ve never written a book and I almost gave up wondering, “Why am I doing this?” Writing a novel is easier than running a company (or possibly any job) in almost every way because it has no grounding in reality. Except writing’s harder in 1 way, which is staying motivated. I miss having a team I love. Writing is isolating and I’ve enjoyed partnering with Eva on our writing project and taking writing workshops at Stanford. After my 5 why’s on how I’ve missed my goal of finishing my book last year, I’m going to be at Stanford 3 or 4 days a week for the next 9 weeks because I have so many workshops. I feel like I’m back in school, except Stanford is so relaxing and resort-like compared to the Spartan halls of MIT. But to be clear, both schools are way easier than running a company.

I’ve learned life lessons from writing fiction. For example, you can increase drama in a story by amping up the subtext. The more desire, emotion, and expectation that’s unsaid, the more tension and conflict you can generate in a scene. There’s a gap between an external conflict and an internal conflict that drives all the action. Eg. the more the hero views climbing the mountain as somehow equivalent to gaining his dad’s approval, or the more the lovers are uncertain how they each feel while they’re competing against each other for the same trophy, the more emotionally turbulent the story. Drama entertains me in fiction, but is not fun for me in reality. Thus, even as I’m amplifying the subtext in my stories, I’m minimizing the subtext in real life. You know I’m already really direct, but now I’m even more direct about what I want. 

I realized that I had been in denial about some of my more “needy” needs, which was creating unnecessary drama in my life. My goal has been to delete the gap between my internal and external goals, between what I feel and what I communicate to myself and others. I’ve told people, “I’m afraid you’re going to think I’m weak if I admit to wanting to impress you.” Up until last year, I never would’ve admitted even to myself to caring what others thought of me except as a vague preference. I view myself as strong, independent, iconoclast who authentically does whatever she wants without considering outside approval, but I now recognize the part of myself that does very much care about being liked, being seen as successful, etc. Recognizing and embracing these internal drivers by bringing them out into the external realm has minimized the subtext in my relationships and drama in my life.

Other than drama, I’ve learned that the quality of my hero depends on the quality of my villain, and that this is analogous to real life. 2D villains are a missed opportunity for building a better hero, and that’s why my favorite villains (and corresponding heroes) are complex anti-heroes like the Joker and Batman, Magneto and the Professor. In life, whenever I’ve viewed a VC or competitor as an obstacle or antagonist, they’ve turned out to be my greatest ally in growth. It’s the challenge that defines the hero and gives you the opportunity to change and affect change. The villain in my book is my favorite character, and he’s taught me to appreciate the “villains” in my life too.

Dating: 
I’ve “dated” dated 4 people in the last 15 years. I started 2019 resenting dating. Dating was a waste of my time, not fun. I had a scarcity mindset about the candidate pool— the single guys my age were defective, hot guys tend to be idiots, etc, etc. I had a spreadsheet that estimated the probability with error bars that a particular candidate might be a match for me based on previous data points, eliminating candidates as soon as they became “known defective.” Although I’d update the weightings as new data came in, this scoring system proved faulty. Since I wasn’t running a company anymore, my executive coach refocused on my dating life. “How many dates do you need to go on this month to hit your goal? Your coaching worksheet says you went on a date with this high scoring guy but you’re not attracted. How will you adjust your process and scorecard as a result?”

Adjustments I made to my dating process: 

• Asking for playful interactions. I don’t find judgment fun. I also find talking about the past boring— I don’t care to hear a rehearsed spiel about the dude’s past and he can google me if he wants to know my resume.
• Guaranteeing 2 dates because I hate everyone on the first date.
• No longer using dating apps because I’m shallow and random when on apps— I don’t find judging fun. Now I’m back to dating people in my network after we’re friends, which is how my best relationships have started.
• Recognizing when I’m lonely so I can avoid dating in that state, because when lonely I throw the scorecard out the window and choose whoever’s most obsessed with me. Instead, when lonely, I should be snuggling cats, reading and writing, and hanging with friends.

I’ve also learned that my scarcity beliefs were false, which was a relief to discover. One of my board members caused me to realize one of my scarcity fears had to do with fearing being a single mom like my mom was after my parents divorced. I lived with my mom while she was dating and I was a teenager, and I had this narrative that it was tough for her because of me, and I was afraid of enduring something similar one day. I’m nowhere near being a single mom, so I wasn’t aware I had this fear, but it was great to identify it and realize it was irrational. This crazy unconscious fear had been making dating not fun for me, but now dating is fun. I also rediscovered this book while on the Southern Startup road trip and now aim to run all relationships with this type of integrity.

Going into 2020, this is the first time in maybe 7 years that I haven’t had a company or relationship goal. Company and dating goals were my top 2 goals in previous years, so this is a big change! I do get depressed when I’m not intensely working on something, and I miss working with a team I love, and I still want to build a fulfilling relationship with a man who inspires and loves me, but somehow I trust that those things will work themselves out without having a plan or goals. 
My goals for 2020 more have to do with all my writing projects, plus I want to make a short film (survey says the “dates with Nancy” short film sounds most fun. Sign up to see it when it comes out because whatever I make will have a limited, non-public release). At Apptimize we did pre-mortems in engineering. I like doing that for my goals: checking in on how shocked I’d feel if I didn’t accomplish a particular goal and then asking how I can make a plan and block out time to make myself more shocked to fail. If you want to share goals, let me know! I am a collaborative planning nerd. Happy 2020!

When I think about all my failures, I don’t regret any of them, except my mom’s death because I didn’t do anything to delay it. My friends told me I did a lot, but they don’t know. The thing with failure is that no one else knows the gap between your reality and your potential the way you know it. No one can judge yourself the way you can.

My dad found he had stage 3 colon cancer at the same time as my mom’s cancer. My mother had left her husband and I was visiting her in Virginia where she’d found a room in an old lady’s mansion. We went to the doctor together to learn what was causing my mother’s back pain. The doctor said, “You have stage 4 lung cancer. I take cancer very seriously. We’re going to fight this.” My mother wrote an email to her friends that she was coming to live with me in Chicago, eliciting responses with references to Jesus.

The next day she told me she was going back to her husband, which filled me with both relief and doubt. That was certainly more convenient for me- I’m not a naturally nurturing, caring person because I’m monkishly devoted to work, but how could they get back together so suddenly?

I alternated flying to Pittsburgh and Princeton to see my parents, 20x more than I’d ever seen them since I left for MIT. For a while it seemed like she was getting better. I told her I needed to go to the London office and didn’t have anyone to care for my cat, and she said she’d come take care of it for me. My coworker exclaimed, “Wow, that’s a VIP cat.” She gave my cat a name, Mimi. I loved this cat so much but I’d never taken the time to name it, and my friends would call it, “The cat w no name.” During her stay in Chicago, she nested the way she always does for me- she cooked, she got me a maid, she arranged furniture, she potted plants, she got them to hang the painting the founder of my company gave me. They were late to hang it and she was running (her, running, with her chemotherapy port!) through the airport to make her flight. Tearfully she exclaimed, “I give my life for you!”

Annoyed, I said, “I didn’t ask you to do that. Who cares about hanging the painting?” It’s easy to be short and mean to people who love you unconditionally.

When it seemed my mother was getting worse, I moved my team to NYC to be closer to Princeton. I neglected my dad more because he was only stage 3. Both parents tried to tell me their frustrations about the medical system, but I was impatient and didn’t want to think about it. I was selfish about my own stress. Wasn’t it enough that I went with them to the doctor even though it was boring and tiring and I would’ve rather been doing something useful like work? Even though I was there, I wasn’t present. I went through the motions without opening my heart. Even though my parents have always been proud of me and in most ways I was the ideal Asian child who independently, ruthlessly achieved more than what my parents could’ve imagined without anyone saying a word, I was a terrible child child.

My father sent her a cure that had something to do with aloe. I read a few books and websites on cancer. There are a lot of alt-medicine theories out there because people are fighting for their lives and need something to believe in. My mother wanted to move to Texas to try the Burzynski clinic. But I was slow to pay for the clinic because it didn’t sound like it could be real. People had sued this doctor as a fraud, and it was tens of thousands of dollars per month, and they don’t take insurance (or insurance doesn’t take them). Even though I could easily afford it, my mother knew I didn’t want to and at the last minute didn’t turn in the paperwork, saying she didn’t want to be a “burden.” There’s a Netflix documentary about this doctor and I have avoided looking at it because I’m afraid it’ll show it was legit.

She had problems with her phone plan and wanted me to deal with it because I was paying the bill but I was too impatient and hate these types of chores, especially talking with Verizon people. Thus towards the end she didn’t have access to good internet to stay connected with her friends. That must’ve felt terrible, to be so isolated while lying in hospice, because she was always texting and very social. I have a story that this phone problem accelerated her death and that it’s my fault she died so unhappily.

For a few weeks I had wished that she would die so it could be over. There was a ticking clock because insurance would only cover up to a certain date and everyone expected her to die before then. Her body had grown bloated and disgusting- I always washed my hands thoroughly after massaging the blood into her clay-like, swollen legs and feet, dying flesh that held the mark of my touch for an unnaturally long time. She had been incontinent for a while and sometimes we’d clean it ourselves when the nurse was slow and the smell started to sink in. My stepfather wiped with brusque efficiency while my mother gasped in pain. I watched awkwardly, embarrassed for her.

I wasn’t there when my mother died. Shameful. My stepfather even hinted, “I’ve never seen her look so weak.” I had a trip planned to go to Chicago for a short vacation, my first in years, so I still left. That night I got his voicemail at 3am saying she’d passed away. I flew back in the morning.

I’d never been to a funeral before. I had grown so thin the flower-y dress I’d long inherited from my mom hung off my body, but people who didn’t know why I was skinny would say I looked great, a real New Yorker with my blowouts and Pradas. Four men declared their love for me. I said that I appreciated it but it wasn’t necessary that they come to the funeral, especially on such late notice and in New Jersey. My team got me flowers.

Friends came and I’ll always be grateful. My dad drove from Pittsburgh and we didn’t know what to do with him, putting him in a back pew. He’d cried when I told him she had cancer. My middle school friend drove from Philadelphia and I took her to my favorite dessert places. Even though he hates taking breaks from his research, my best friend from high school nerd camp flew from Stanford to visit for 1 day and be with me at the funeral. Everyone thought he was my boyfriend and I was relieved to lean on him.

At the funeral, I gave a speech about how she sent me on a flight with a houseplant in my carry-on. My stepdad talked about how she’d get last minute tickets and magically access things and get people to do stuff for her, enigmatically explaining, “I’m Chinese.” The priest said how she had so much assertive personality and insisted everyone wear colors to her funeral. Afterwards, some fobby Chinese people posed and took photos with the casket flowers. I never talked with her church friends again even though they’d done more for her than I did, bringing soup and praying with her every day.

I was in awe of their Christian charity because I doubt I would’ve done this for anyone else. When my high school friend Jeremy was dying of bone cancer, I thought of him and donated money to his causes, but I never went to Pittsburgh to see him. I would sometimes think of how often I’d walk by his house with the red door, how he introduced me to sparkling water, how we watched “Hedwig and the Angry Inch” and he explained how her head really did get hit in the blooper, how we lay in the sun room and stared at the strangeness of how it is to be human in high school, how his dad smiled with delight at the “elfin” portrait I drew, immediately grabbing it to admire and figure out how to display.

I flew a lot to see my parents during their sickness, but it wasn’t real sacrifice. I didn’t know what real sacrifice was. I’d never been self sacrificing. With my parents, I was willfully ignorant and didn’t take ownership of helping them treat their diseases. I never viewed them as assets or part of my team, more as a burden I had to dutifully endure. I had my own goals separate from them.

Years later, I was at Beregovsky’s wedding and my date translated the Jewish contract, “He vows to give her the shirt off his back.” I thought about that level of love and commitment and thought about how much I’d have to love and value someone to be able to make a promise like that to my husband. If my mate had cancer, and I’d loved them enough to have vowed to become one flesh and give them the shirt off my back in the first place, I imagine I’d quit my job, I’d move with them to be near the best hospital, I’d become a research expert in the field, I’d do everything with a smile because there’s nowhere else I’d rather be. Basically the opposite of what I did for my parents.

I’ve always been very focused on my own goals. When I set a goal, I know it’ll happen because I’m an effective person and I always figure out a way to win. Nobody bets against me- when playing poker people say I’m intimidating/ scary, and my coworker wrote a song about how everyone wants to be on my team.

For me, failure isn’t about not accomplishing a goal. I fail at having the wrong goals in the first place, a deeper problem. I have the arrogance to believe that if I’d made it my goal to delay my mother’s death, I could’ve. I just didn’t think about it because I was too selfish and on autopilot in my focus on work. Because work was always making progress and thus more fun and easy to deem worthy of attention, whereas she was not making progress, her health hard for me to control, and generally thus a distraction. I don’t regret not trying harder to keep her alive, but I do regret not showing her more love and connecting more with her instead of sitting there with my kindle and VPN-ing into work- so much wasted time.

Even though she didn’t seem like a big part of my world, her death changed my world. I’m grateful for how selfless and kind my friends and family are. I try to be a better person every day but it’s hard. Since I was a child, I’d grade myself and I almost always give myself a B-, which is, as I explain to my team when giving out our grades, an Asian F. I’ll tell them, “99% of startups die, so if we’re not at least 99th percentile as a startup, we’re getting killed.” I hired the type of people who find this inspiring. We like to work and we like to win. But every day I remind myself that success without love is the biggest failure.

I knew from the womb that for me a life without impact would be failure. I knew from all my reading that wealth without meaning was failure. I never need to worry about not being ambitious enough, not growing enough, not working enough, not being insightful/ introspective/ perceptive enough. I don’t even have to worry about not being compassionate or empathetic enough because when my attention is on you, I’m emotional, giving, thankful, and intuitive. The failure modes I have are the flip side of my strengths- I can be too focused, too competitive, too right. I have to be less judging and more patient, more generous with my attention. Since her death, I’ve learned that everyone I love is a chance to practice loving more, loving better. Grading myself, I’m still generally failing at this, but I’m thankful that the people I love don’t judge me too harshly for it.