Author: nancyhua

I’ve always been obsessed with growth. When I was CEO, this obsession went into hyperdrive because startups are all about growth and I kept telling myself, “I have to prove I can scale.” For 6+ years, I went through dozens of executive coaches, CEO groups, and coaching programs, read 100+ business books, all with the aim of continually exponentially leveling up in life so that I was bottlenecking my company’s growth as little as possible. Every coach has their own framework, and I went through different types of coaching: productivity/ accountability coaching, therapy-like communication/ group dynamics sessions, skills coaching (from media training, to operational leadership like running meetings, KPI’s, hiring, management, 360’s, etc). After $100K+ in coaching and self development services, what did I learn about how to best level up?

I concluded that increasing in self awareness is the ultimate power. No matter how much power and resources and money I have, I’m restricted to reacting at the level of awareness I’m operating at. At the lowest level of consciousness, I’m a slave to my desires, a beast, easily manipulated by external circumstances, my body, my emotions, my biases, my ego. At higher levels of awareness, I can notice and appreciate my patterns, and I can change them.

The best way I found of improving self awareness is Conscious Leadership forums. I want you to do it. It’s ~$10K+/ year and if you can’t pay for it, I will pay half the fee for 5 people who ask me.

I’ve been in many founder/ CEO groups, often because I was excited to join something exclusive. Each time it was fun onboarding onto a new framework and meeting people, but then we’d fall into the same patterns. We’d whine about engineering/ executive hiring, fundraising, engineering management. We’d end with exchanging intros for recruiters or doing arithmetic around SaaS metrics. I’d start looking for a new coach/ group to join. I’d wonder, “Is there more? Do I really know so much already? Are these fields just not that deep, or am I an idiot, or are these learnings experiential and unlearnable through abstractions like language?”

I’m a writer, I love the science of story structure, and I often look at my life as though it were a movie. Waking up is a key part of my favorite movies like Fight Club and The Matrix. I love the moment of revelation that unlocks and repaints the story. Going through CLG has been one of those fundamental shifts for me. Now, I look back on my experiences and can tell a more insightful story about them, not just a simple villain/ victim story of blaming someone / circumstances for the conflict, or with a deus ex machina event where that new hire or my great idea swoops in to save the day, but a philosophical story that changes how I see the world.

I love being able to dissect the story of my life on a meta level so that it’s not just an episodic sitcom that keeps repeating and glorifying how great the protagonist is at fighting or seducing people while everyone else acts as an antagonistic/ comedic foil. This is my life we’re talking about- I want to build a deeper arc and unveil my wizards of Oz. I don’t want to sweatily re-live my favorite scenes again and again, the same pornography of impressing the highest status whatever, getting into the most elite thing, being the most desirable/ successful/ smart. I want the story of my life to be mind blowing on a totally different level. I want to grow substantively, repeatedly. The movie of my life doesn’t need expensive special effects so long as it’s thematically rich. The wonderful thing about theme is that it’s free. It’s all in the writing, in the awareness of the writer, and the writer is me.

What entertained me for hours when I was naive to story structure- Wile-E Coyote endlessly chasing the roadrunner with bigger and bigger explosives- left me hungry for capital-M-More once I understood the cartoon’s underlying structure. When I learned the tropes and how the conventions of genre work, the patterns unveiled themselves to me, I could predict how the movie would go, and I could choose how I wanted to innovate on the script. Isn’t that more fun than continuing to watch the same thing unfold forever? It remains literally world shattering to see the stories I unconsciously tell myself about my world, to gain the lucidity to affect the script instead of blindly continuing to chase my roadrunners with bigger and bigger explosives. Do you want to learn the underlying structures behind the stories you tell yourself about your world every moment? Isn’t awareness of story structure key to experiencing the most exquisite movie, the movie of our lives that we’re currently casting, writing, and acting in?

Writers learn that in the most powerful stories, underneath your protagonist’s conscious, voiced drive, they have an unconscious, subliminal need (ie. Ricky Bobby consciously wants to win car races but unconsciously wants his dad’s love). The arc of the story requires bringing the unconscious into the light so that the protagonist can grow and their world can change. A well structured story circle feels surprising, revelatory, satisfying, and inevitable. It’s so cheap to insert substance- if a story doesn’t have theme, the only reason is a lack of awareness. Why blow millions on special effects if your story doesn’t explore a heart shaking, deep truth?

Anyway, that’s what I realized was happening in my life- the movie of my life was exciting in a shallow way, with $ and stakes and drama at various moments, but it was a fleeting story that had limited depth of meaning. I had the conscious drives of proving I was the best XYZ, all the while being driven by unconscious desires for love, to be worthy, and I kept missing the turn that would break the story. Until I brought my unconscious desires into the light, my story would keep feeling like Act 1. I’d keep wondering, “Is there more?” and, so long as I wasn’t seeing the truth, “more” would just seem like more of the same old thing, which isn’t actually more of anything. People gain awareness through repeatedly unveiling the unconscious desire driving their conscious actions, and after they see the unconscious, they can finally change the pattern and go a layer deeper to find a new pattern. We can control patterns that we can see, but not the ones we can’t see.

Without awareness, we’re repeating the same thing again and again, an episodic, masturbatory tv show of Sherlock Holmes solving crimes again and again, showing how dumb everyone else is, how he’s always right, never learning, never changing. And that’s fine as entertainment- it’s fun to be right, it’s celebrating and embracing an event that we enjoy and want to see again and again. But that’s not our highest art, that’s not all the meaning there is, that’s not our full potential, that’s not how I want to experience my whole life. I want to change and figure out how I’m wrong. I want to see the meta pattern and tell a full story of my self and my world in a way that doesn’t blame anyone. When we talk with each other and tell each other the stories of our lives, let’s not masturbate the whole time. Let’s go deeper and birth something new and magical. Let’s always keep leveling up. Let’s not keep cycling through our narrative patterns without curiosity.

TLDR; I would love to invite my wider network into CLG. They have forum openings right now. If your company won’t pay for it, I will pay for half of it for 5 people so long as you are in the program for the full year. Contact me if you want my support in doing CLG. I’m excited to commit to leveling up in consciousness together.

Self awareness is the key to easing suffering. Without self awareness, we’re slaves to the patterns in our brains. The universe reflects our unknown biases, so we’re caged within our own blind spots, trapped in patterns that reinforce how we’ve learned to see reality, missing the richness of the infinite other possibilities. It’s easy to read stoic/ buddhist philosophy and think we’re enlightened, but there is a huge gap between theory and practice. CLG takes it beyond theory into structures that make it easier to see when we’re reactive and blinded to higher levels of awareness. Let’s level up so the movies of our lives can become more thematically deep.

I froze more eggs during COVID! Now I’ve done 3 cycles and feel I have abundant eggs. Even if none of them turn into a baby whenever I’m ready to have them, I feel like I gave it a solid try and am free of biological clock time scarcity. FB posts from friends have motivated me to freeze my eggs, so this post is my way of passing on and adding to the story.

Birth control unlocked freedom for uneducated women, giving the choice to go to school, to get a job. Egg freezing is the 2nd half of that equation. Egg freezing unlocks freedom for educated women, giving us the choice to enjoy the fruits of our careers instead of feeling like we’re sacrificing personal life for career, or being rushed because of time scarcity. For the first time in human history, the 2 technologies give women male-like freedom over their reproductive destinies. Egg freezing + birth control level the playing field for women. Until a few years ago, I never thought of a new path towards domestic bliss because, until the last few decades, stories of successful women being single moms via surrogates at age 45 didn’t seem accessible, financially or biologically. But now there are other stories that are possible, and we’re the first generation that will see what kinds of families we’ll create. 

The happily-ever-after story I learned as a kid went like this: I’d effortlessly marry my childhood sweetheart (even though I didn’t have one), we’d take over the world together by day while making love all night, and when we’d sufficiently mastered and indulged that phase of life, start pushing out as many babies as possible. In high school, I chastised my best friend for dating idiots who were clearly beneath her. In college, I didn’t date seriously, especially no one my senior year because, even if I liked the guy, we were going to get jobs in different cities and break up anyway. I didn’t date for most of my 20’s because I was focused on my work and my family. But when I hit 30, I realized that my family fantasy was not coming true. It had already not happened. I had to catch up! My high school friends were long married. My MIT friends weren’t married yet, but they were heading there. 

My executive coach asked me, “How old is your dad? Do you want him to have a relationship with your children? Right, so when do you need to marry by? So how many dates do you need to go on per week?” I was busy running my company, and I resented that I, the great Nancy Hua, had to go on dates with internet strangers just to build pipeline. Why couldn’t I effortlessly fall in love with some supermodel genius who was already my best friend and had loved me for years, as per my childhood fantasy? Instead, I was stooping to swiping on apps. 

I told my personal trainer my dating stories to make him laugh. He said, “You’re such a badass. I told my friends your dating stories. That last guy isn’t good enough for you.” Then he looked at me aghast, “Are you crying?!” I couldn’t explain why I was crying into my towel, mid-dead-lift. When he said, “You can have any guy you want. Every girl here wants to look more like you,” I cried harder. When people told me they were sure I’d find someone, I’d feel so hopeless and heartbroken. One of my executives discovered this the hard way when he remarked during our 1:1, “You’re the most eligible catch I can think of,” and I burst into tears. “Why are you crying?” he asked, eyes wide. “Don’t go into the office or the bathroom in case the team sees you.” 

Dating was not fun for me because I was doing it out of fear, so I’d try frantically dating in bursts, get tired and sad and delete all the apps, take 8 months off during which I’d distract myself with my friends and my work, then get scared of dying alone again and re-download all the apps. This happened for several years. With my biological clock counting down, I wondered if I should just settle. 

Then I stopped being CEO of my company and decided to never do anything that I wouldn’t do solely for the fun of it again. This included dating, because dating for me was about alleviating the fear of being alone, not about the joy of dating. I got curious about all my fears and sat with them. I was scared of my friends leaving me behind, of not prioritizing me once they got married and had kids, of being a single mom, of being lonely. I sat with each fear, and looked at the opposite story. I thought of how I’d seen married friends get divorced, how I’d grown closer to friends after they’d married and had children, how it could be better to be a single mom than co-parent with someone who wasn’t right for you, how married people could be even lonelier than single people. I saw how I was making finding a partner the Way to Having a Happy Family, when really it was no guarantee of happiness, as evidenced by so much experience I’d personally witnessed and experienced. I started looking for counterexamples and saw them everywhere, single moms, successful women I knew like my VC’s, or celebrities like Lucy Liu or Shonda Rhimes, raising children on their own even though they could probably marry genius supermodels if they wanted. I started to see another way the happily ever after story could happen. 

I wrote on my goals doc, “Freeze enough eggs such that I feel abundant about future progeny.” Then I did nothing for years. 

One day, Diane posted on FB about freezing her eggs, which inspired me to get off my butt. I did one cycle, then thought I was done. But my founder friends told me stories that scared me into intending to do more cycles. I procrastinated that until Jessica posted on FB about freezing her eggs. Then I did 2 more cycles and crossed off “freeze enough eggs” from my goals list. 

In my 20’s, I thought I wasn’t afraid of being alone, or afraid of anything, but I was just better able to ignore fear then. My 30’s forced me to face my fears, which I’m grateful for because now I don’t have those fears. Facing fear, I saw that the fear I was avoiding was with me all along, and that I was fine. I was always feeling it even when I was running from it. So it’s better to love it and feel it instead of trying to control it, which is futile and was actually making everything worse. Trying to control my emotions or the future is like building a sandcastle. It’s a fight against nature. Life wants to shift and change. Emotions want to be felt, to move and to move you. All I can do is play with it. And when I dance instead of control, I see life can be better than I’m able to imagine. 

Now I look forward to potentially being a single mom, to dying alone. I’ve embraced being a cat lady. Not to say that I’ve given up on love! I want to love again and raise a family with a man I’m devoted to. I’m just no longer afraid of that not happening. Rather than settling, my standards have gotten higher over time because I love my friends and my aloneness and my cat more every day, and anything new would have to be better than investing in my existing exquisite life. I look forward to making beating my aloneness as hard as possible, and to being delighted if it ever happens. 

The Egg Freezing Process: 

Each cycle took 8-10 days. So fast! COVID is a great time to freeze eggs because, unlike my first cycle, I don’t travel or do anything, freeing my body to do nothing but cook up eggs. The first cycle, years ago, I went to UCSF because Diane used them and it was close to my work. They extracted 16 and froze 11 eggs. 

My friend Jessica went to RMA so I decided to use them for my extractions this year. Sart.org only had data for RMA’s NJ office, but that data was good and Jessica is smart, so I went with them. I loved RMA! They were really communicative over text and super organized. They worked during Thanksgiving and Christmas. 

At RMA, the 1st cycle took place a week or so after my period. The time from 1st injection to extraction was 10 days. I went in about every 3 days so they could check on the follicles, and I found the process fast and fun. I never felt like they were wasting my time or being inefficient. Everyone was smart and nice. I loved interacting with everyone and highly recommend them. 

I injected myself with 1-3 medications every night for 10 days. I figure out how to have fun no matter what I’m doing, so I generally enjoyed injecting myself. I felt like I was playing at being a mad scientist mixing powders and tapping for air bubbles. I found it satisfying to *poink* into my juicy flesh. I did get scared towards the end of the last cycle when I started making mistakes. I bruised myself by hitting a blood vessel or something somehow, and I injected air by forgetting to expel the air, which made me scared I was going to die, but a doctor friend said I was fine.

The extraction took about an hour and I was knocked out. When I woke up, the first thing I exclaimed was, “I feel great!” They said they extracted 27 eggs and froze 21.

The 2nd cycle took place immediately after my period, and was just like the 1st cycle except 2 days shorter and with fewer side effects. The time from 1st injection to extraction was 8 days. They extracted 19 and froze 16. With 40+ eggs banked, I felt abundant about future progeny. 

Costs per cycle: 

$8K for the procedure. 

~$2K for medications. You don’t know how much medicine you’ll need because it depends on how your body responds. Alto delivers same day, so you can avoid ordering more medication until you’re sure to save $. Also they give you a caramel with every delivery, so you’re incentivized to increase delivery count. 

Side Effects: 

The first cycle I did with UCSF, I don’t remember having any side effects even though I was worried about acting crazy. I did feel sore after the procedure and watched hours of Reign (a show I’ve never watched before or since) and shop for elaborate ball gowns, which is uncharacteristic of me, but that was just for 1 day. 

The first cycle with RMA, I gained 9 pounds in 3 days! I’ve never bloated like that before, and it was uncomfortable. Lying on the exam table, I felt like a queen bee whose limbs had withered off, only a gigantic thorax remaining with drones swarming around me feeding me royal jelly while I pooped out eggs. It was water weight, and the day before the procedure I somehow lost 4 pounds, maybe because I had swapped the hormones for the trigger shot. Anyway, a week after the procedure, I was back to my normal weight. 

I babied myself this whole time with lots of heating pads and soups and basically followed what I guessed my cousin would say Traditional Chinese Medicine would say, and basically soupifying everything before I ate it (even fruit) and under-washing my hair. I started getting into making mushroom barley and other veggie soups. I bought a bread machine, an electric steamer, and tons of wild rice. But when those hormones went away, so did the urge to bake. 

The final time with RMA, I didn’t bloat, which made me worried it wasn’t working, but it was. We did this cycle immediately after my period, whereas with the previous cycle, we started injections about a week before I would’ve normally ovulated, so maybe that made a difference.

Both times, my uterus and boobs felt sore so I used heating pads. Unlike my first cycle years ago when I was running around working a ton, for the cycles with RMA, I basically lay in bed all day for a week under a giant heating pad. Generally lethargic, I was not in the mood to do anything other than watch pretty people entertain me via Netflix. My cat was really happy to get so much snuggling and warmth.

The day after my extraction, I got the strong urge to do annoying tasks I’d been putting off for literally years, like a super-charged PMS time (when I’m in my PMS zone, I get into hyperproductive, focused, conscientious mode). For example, I got very interested in my taxes, which has never happened before. As I’ve aged, I’ve learned to notice and love my cycles. My hormone cycles weren’t noticeable until my 30’s when I started getting PMS symptoms. When PMS-ing, I start to clean my house, figuratively and literally. I throw out stuff, organize drawers, and speed to inbox zero with renewed zeal and certainty. The morning after my extraction, I, with genuine gusto, got new health insurance, transfered my retirement accounts, and mailed a package. My body was like, “I guess we’re not pregnant so let’s get busy creating whatever else we do with our lives when we’re not making babies.” All my times of the month bring unique benefits, and I love making the various parts of the cycle work for me. 

Reproductive Therapist:

I was thinking of freezing embryos, so I did a session with a fertility therapist Annie that RMA referred me to. 

Annie asked, “How did you decide to freeze eggs?”

I said, “I always meant to, but I kept putting it off. Finally my friends posted on Facebook and that inspired me to pull the trigger.”

She said, “Yes, that’s often the case, where women in tech read on some message board randomly and then finally do it.” Indeed, my friends who posted are both women with STEM PhD’s from Stanford and Caltech who work in tech. This post is my way of passing on and adding to the story. Sharing more personal experiences has been a gift from Facebook because it safely normalizes / surfaces some things we can normally view as private, which can help us learn more faster together, so I want to share my experience of this process.

Annie asked, “When do you want to have children?”

I said, “It sounds silly, but I read Lucy Liu had her kid via surrogate at 45. She’s Asian, and I’m Asian, so I arbitrarily pegged that age in my mind as roughly when I’ll have kids if I still haven’t by then. But a decade is so far in the future; I almost can’t imagine it.”

She said, “That makes sense. There aren’t a lot of models for successful women who can afford to be single moms with abundant resources and support network. It’s new.”

I asked, “What blind spots do you see women having?”

She said, “I see people who have a very specific time they want to have kids by, and that lack of flexibility can cause issues. I also see people underestimating the support of the community and overestimating the importance of their significant other.” 

“I won’t overestimate the importance of my significant other versus my friends. My friends are the standard that helps me set the bar and decide if a guy is worth dating. He’d have to be really special to be worth investing in instead of just continuing to invest in my friends.”

“What if holding that standard means you are alone?”

“Then I’m alone! I saw a video on tik tok where this girl was saying we don’t need men because women make sperm in their bone marrow.” We laughed. 

Philosophy: 

The future is fundamentally uncertain and thus scary, so I try to give myself the illusion of control to try to alleviate my fears. Yet control is impossible. Even with all the eggs I’ve allegedly frozen, who knows what power outage or earthquake could happen. Maybe I’ll go to the doctors in 10 years and they’ll be like, “What eggs?” Maybe none of my eggs will convert to being a child. Maybe my child will die young. Maybe my child will grow up to hate me. No one knows. From the view of fear, nothing I do is ever enough to make me safe, because safety and certainty are impossible. All is illusory. So we might as well choose the illusion of abundance instead. And, of course, take advantage of the amazing, abundant technologies available to us. Scientists can make embryos out of skin cells. Through science, much is possible. 

Anyway, abundance teaches me that even if my friends spurn me, and I never find true love, and I never have children, I’ll always have me, and that’s just as abundant as it is scarce. It’s cool, having enough, being enough, letting go of control, all an illusion anyway. Whatever happens, I know I’ll be ok, more than ok. I’m not going to do anything out of fear anymore. I’m doing it because I can, because I want to, because it’s fun. 

Technological change drives cultural change, and in this case egg freezing changes the possible futures I can envision for myself. Now I see infinite stories full of abundant joy and no longer feel any scarcity or pressure.

“Annapurna, to which we had gone empty handed, was a treasure on which we should live the rest of our days. With this realization we turn the page: a new life begins. There are other Annapurnas in the lives of men.” There are other Annapurnas in the lives of women.

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.