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Family Fantasy

my parents and me
my parents and me

Fantasizing is a waste of time. If I catch myself fantasizing, I think about my missions and get back to work. But one fantasy has persisted about my future family. This vision formed when I was small, and I only recently realized not everyone’s vision of their dream family differs so much from their actual family. That’s probably how you know happiness, when you hope your kids get to have the same life.

I consider my childhood happy, but it was confusing. My dad came to the USA when I was 1 and my mom followed after, so the next few years I was in China, living with my parent’s friends and my aunt. I remember not knowing if it was safe to leave preschool with someone claiming to be my mother’s friend, instead of my mom. I remember my dad’s teacher hauling me by the hand across a concrete tundra to get endless shots in my butt because I was always sick in China.

I stopped getting sick when I came to America at 4. Alone on the airplane, the flight attendant told me not to eat a gold yellow packet. When she turned, I opened the shiny square and stuck it in my mouth. I immediately gagged at the taste. Seeing my face, she said, “You ate it, didn’t you?” Later, I realized I’d bitten a pat of butter, the first milk product I’d ever seen.

When we landed in America, 2 men took me to another man. One man hesitated, then said, “Do you know him?” I shook my head no. He drew my attention to another person. “Recognize?”
Yes. I knew my mother after all those years. The man turned out to be my father. We went to a restaurant and I asked, “Is that guy eating poop?” My dad explained, “It’s mustard on a hot dog.” Life was one discovery after the next.

In America, I was always at the library. My goal was to read every book in the children’s section and I made good progress. When I read the Boxcar children, I fantasized I’d have 5 children who all had different favorite colors. An only child, I never wanted a sibling, but I wanted my kids to have many siblings. Despite much begging, I wasn’t allowed a dog, so I wanted my children to always have a doggo. My vision incorporated scenes from Madeleine L’Engle books like A Wrinkle in Time where a tumble of children would help each other through scientific/ Biblical adventures, singing hymns, the dying grandfather reading poetry aloud, the upright dad trapped on Mars while everyone actively misses him, the scientist mom holding it all together and cooking dinner on her bunsen burner, the baby wandering in to eat the skin off the warmed milk, while upstairs a kitten nestles the awkward daughter in the chilly attic bedroom. I wanted a kooky house filled with love and science and animals.

In 5th grade my best friend gushed over cute babies, while I called babies “gross.”
Anjani said, “When I’m old, I’d love to have a nice yard with cookies for the neighborhood children, like how Jane Austen lowered baskets of treats for them.”
I said, “I’d have big black dogs that’d eat anyone who snuck onto my property uninvited.”
She scolded me for my remarks, while I suspected she was putting on an act perpetuated by Society. Alleged love of someone else’s children must be a myth, because have you seen other people’s children? As a 5th grader, I couldn’t stand many of the kids I knew, and younger kids were even worse than us because babies are sociopaths until the empathy parts start developing in their brains and you have to teach them to restrain their natural cruelty through songs on how to share without punching. This is science: babies are designed to be sociopaths so that you don’t let them die despite their useless annoyingness- I was being smart by not caving to their machinations.

Being a parent seems like the essence of responsibility without control. This fundamental experience that humanizes any villain and connects all life is so simple, just a roll in the hay away, and yet such a big deal. It’s simpler to have kids accidentally because deciding to have kids is choosing to become a new, unknown person through your values/ priorities and brain chemistry all changing. Hopefully a better person, but potentially a person that the current you would despise. Part of me has a horror of being “normal.” Another part doesn’t believe it’s possible to have it all because of how focused I am on my goals, how I guard my time- how could I bear the love and pain and boredom of being a mom?

Then another part of me thinks it’d be fun to have kids! I want to see what they’re like, to learn together and joke about how they’ll never live up to my legacy while warning of my disappointment if they don’t attend MIT and live in East Campus. I want to see if they’ll believe my stories and see how much savvy and imagination I can beat into them. I’ll watch them assert their own personhood and become DJ’s (what do DJ’s do??) while I bemoan their squandered opportunities and inability to speak Chinese. I’ll be secretly proud of them for teaming up against me to sneak out or cover up shenanigans.

This is fantasy, because I know nothing about children or siblings, children do not act this way, and adventures aren’t safe or fun. Part of me denied wanting this ridiculous fantasy because it seemed too mundane for someone like me to dream of domestic bliss. “I’m too special and ambitious, not the type to seek a normal life. If I ever had kids, it’d only be after reigning in Fillory for 9 times 9 years.” But the other part of me wants it without letting go. Like after a hike to the top of a mountain, hearing the wind stroke the forest below, a thought might surprise me, “My kids would love to see this, I know.”

I haven’t kept a plant alive since 2015, and I started thinking about freezing my eggs. I put it off for a few years because I’m young and it seemed potentially risky and annoying. It wasn’t until Diane and my VC froze their eggs in 2017 that I acted. didn’t want to worry about a biological clock even a little bit. I went to UCSF because it was really close to my office and Diane had warned that you couldn’t travel during the last weeks because you needed to go in to get your blood drawn daily.

I’m an impatient patient. Dealing with 2 parents who’ve had cancer and seeing the death and pain that comes from naively trusting the experts, I’ve lost faith in our medical system and am openly skeptical and suspicious of something so misaligned with our long term health. Egg freezing is a long term health thing, so I was prepared to discover they wouldn’t act in my best interest.

The doctor was a jolly Santa who didn’t acknowledge my impatience. Although he asked me what I knew about it and I replied I knew it all, he launched into his standard speech on the history of egg freezing science. “This paper from 2011 shows our procedure,” and he handed me a stapled packet of papers. Not knowing what else to do, I read the abstract as he continued monologuing.

I interrupted, “How many babies have come from the eggs you’ve extracted?” This triggered a rewind of afore-summarized statistics around how many eggs survive the thawing, etc.

I interrupted again, “Do you have specific numbers? How many eggs have you frozen, and then how many babies have come out of those?”

After a few back and forths, he said, “It’s impossible to know due to reporting difficulties. We have to call the mother months after she thaws the eggs to see if it took, because they don’t always do that here, and they’re often hard to reach, and even then they don’t always tell us. Statistics of any kind are also impossible to get because of the rules around data collection and all the bureaucracy and you can’t transfer stuff between hospitals.”

“Got it. You get why I’m asking, right? I want to get a sense of the probability that in 10 years when you ‘unfreeze my eggs’ and I or a surrogate eventually gives birth to some Asian-looking baby, that it was actually my egg. Or that, in 10 years when the staff’s all different and I ask for eggs, some new doctor shrugs, ‘What eggs?’ I won’t know until years from now, so I want to know what’s happened in the past.”

“They’ll be your eggs.”

“So you’ve seen babies come out of eggs you’ve frozen, you just don’t know how many.”

“Yes, lots of babies. You can have babies even when you’re 70.”

“You’ve produced hundreds of babies, or thousands…?”

“So many! We’re one of the biggest facilities in the world. The average facility does 20 procedures a year, we do 20 a day. We pioneered this in the 90’s. Our first paper-” More stuff from the papers, but I was done pushing. I was surprised and underwhelmed to hear him say it was literally impossible to know real stats, but I figured it was probably ok.

The next few weeks, I stuck myself with needles day and night and went in for endless blood draws and ultrasounds. I was surprised their appointment scheduling system worked because it seemed so disorganized, and a few times they scheduled appointments for things that could’ve 100% been done through email, but I endured despite how clearly the system didn’t value anyone’s time and was both over-engineered and un-designed. I told my CEO group, “I wonder what crazy things I’m going to do over the next few weeks because I’m on these hormones,” but interestingly no one observed anything unexpected re: my behavior, which gives me hope that I’d be a relatively sane pregnant lady.

The extraction itself was invisible to me. I had never had surgery except wisdom tooth before, and I was amazed by how one second they’re asking you boring questions waiting for you to pass out and the next instant you’re in another room and Gemma’s there. My first question upon waking was, “How did you move me?” This interval is what I imagine being cryogenically frozen and revived would be like, and decreases my fear of death because now I understand that when you’re dead, you really don’t feel anything, so who cares?

Anyway, Gemma had brought me Gatorade and I was thinking we’d go back to the office but then I acknowledged wooziness so she took me home. Then nesting hormones kicked in and I did some uncharacteristic things. For example, I took quizzes on my gardening style (vegetable and herb) and figured out what kind of architecture I favor (modern / log cabin). I found myself on Zillow looking up modern houses in Pittsburgh and marveling, “I could buy 10 of these!” while browsing some show called Reign on Netflix and considered coming to work in a ball gown. It’s amazing what happens when you’re souped up on hormones.

And that was that. They claim the eggs are safely frozen somewhere and I assume they’re right. It took 2 months from initiation to close and it wasn’t that painful- I didn’t gain weight or do anything too crazy and I picked up needle skills.

Freezing my eggs, I’m freezing the fantasy so I can have it one day when I’m allowed. When I was a kid, I vowed I’d do all the forbidden things when I became a grown-up, but the thing is you grow up and become responsible. In some ways, I allow myself less than my parents allowed me as a kid- no more diet of Cap’n Crunch, Fruit by the Foot, and m&m’s; no more jumping from tall objects; no more running across busy intersections on dares; no more picking at scabs. But sleeping in, unfinished food, constant reading- allowed, allowed, allowed!

I think the step for me before children might be an old dog. I’m not allowing myself a dog yet, but one day I’ll have one. This fantasy dog lurks in shadow, working up the courage to creep to the ring of my fire. One day when it lets itself take food from my fingers, I’ll have allowed the wildness in.

Apptimize S5E5: SF Office Move

People care about office location. Conflicting priorities and the existential danger of commitment charge the question of office location with powerful emotions, emotions I’ve been both agonizing over and toying with since Season 1 Episode 1. San Francisco, the South Bay, and our Apptimize office have formed a multi-year long “will they or won’t they” love triangle, a staple source of dramatic tension in the context of our startup growth- growth fueled by our industry revolution, a revolution set in the backdrop of our species’ social and technological revolutions. Exciting! This month, our team committed to a move away from our original pairing.

To recap the past: we started Apptimize in Mountain View in 2013. Our first office was in a building on the Google campus rumored to be scheduled for tear down. Trust was so high and the weather so mild in the Google garden of Eden that the building was unlocked and nerds wandered in and out freely. Khan Academy was in our building (I snuck food from their office often (not often enough)), as was Clinkle. We did not pay rent but lived off the land in Jeremy’s old company’s suite even as another company moved in, surely eating of any fruit of any tree we chose. In our purity as a proto-person, we dared to ask the new tenants if we could continue to use their furniture and office space for free. And we dared to continue working there for weeks after their awkward silence hardened into awkward post-it notes tagging, “These office chairs came with our lease.” Jeremy told me, “I think they’re too scared to approach you but that one guy whispered to me that we should probably go.”

Robot Invader’s office was in the same office complex and they took us in and ultimately became our first users. We took money plants with us in the move because Jeremy assured me that the new tenants wouldn’t have gotten those as part of the lease, and I loved free stuff and plants (although they died immediately because I don’t love caring for them). I did our office move by myself one night, lugging Jeremy’s monitor up and down various staircases by taking rest stops. Jeremy told me, “I appreciate you doing this but you should have asked for help because you cracked the monitor. A piece of it fell off and people who know me know my monitor is my baby.” I was unapologetic, a recurring theme in the recurring chaos I caused in our recurring moves.

After we got into Y Combinator, we split time between my house and Robot Invader because some of our early developers lived with me for free for years. We had a 5 bedroom house 5 minutes from Google that was sometimes our office especially when we worked weekends for the first few years of Apptimize.

We also worked out of a fellow Y Combinator startup’s offices in SF out of a compromise for our SF contingent- the dozen of us alternating days between South Bay and SF. I asked Y Combinator what they thought of this dynamic arrangement and Justin Kan told me, “When you’re small you can do whatever you want,” advice I overly liked and recalled.

After raising our seed, we moved into a 10K square feet office across the street from Facebook owned by one of our angel investors Massy and Sateez. They used to house 100+ people in this building and now it was for our team of 12, so we had lots of room to grow. An instance of startup karma, our users Robot Invader moved into our Menlo space, turning the tables from the days when we stayed with them at the old Google Building.

We slowly eventually tore down the cubicles after a few years. One executive recruiter told me a candidate called our office dark (following his linkedin since interviewing him, he’s been a trainwreck- I maintain that cubicles are good), but we were already contemplating a redesign. Shauna helped us redo everything [photos]. I loved that this office was right across the marsh where we did walking meetings.

apptimize menlo cubicles

When I moved to SF personally, I assumed we’d move the company to SF soon. We’d been discussing it for months and the SF people, while a minority in the company, were annoyingly vocal complainers (is that any surprise to anyone?). I said we’d do it after the Series B because I needed to focus on our funding strategy first and the move could be tied to a celebration of not dying.

We raised our Series B during a hard fundraising time. 2016 started with the SaaS-pocalypse where public markets were getting pounded, Silicon Valley SaaS technology paragons like LinkedIn and Salesforce were dropping, startup founder darlings like Zenefits’ CEO were getting ousted, reporters were unhelpfully speculating the venture “correction,” and only the highest conviction VC’s so confident in their records that they didn’t read tech blogs were in the game. Our deck was coming together in January 2016 and my Series A investors kindly told me that it was not good. Undeterred and without Lynn to make our deck, I went out into the market and started taking meetings. For the first time, I envied bootstrapped startups. After decades of being straight edge and using clean language, I re-learned my middle school habit of swearing and gained 15 pounds in 1 month.

I’m not going to detail the drama of this time here. Despite the climate, we did well. The result was that this round was awesomely good to us. Within a few months, we raised >$15M with top investors such as Glynn Capital, Goldcrest, USVP, and Stanford Fund.

After we started getting term sheets, I turned back to the business and saw we had major stuff to focus on. I lost 15 pounds in 1 month because I had so much energy around all the work there was to do. When I said I was really happy during a meeting where it was clear everything needed work, Lisa said, “You’re happy because and you’re really busy.” Yes! Good-busy, like making-progress-energizing-busy, not gain-15-pounds-stressing-over-cat-herding busy.

Everyone was doing multiple jobs. I’m proud and inspired by how our team stepped up, how much we accomplished and learned. I had my ordered list of priorities, promising Chris I was going to un-fuck X after first un-fucking Y. So our long suffering SF contingent who I had hardened my heart against (with the taunting refrain, “You knew what you were getting into when you joined”), got their hopes shelved into “I can’t think about anything else especially a move until after this next milestone” purgatory.

Late last year, our team had a hard time hiring to scale. Here’s the thing with running a company predicated on the idea of data, testing, and iteration: you feel guilty if you don’t run experiments so people manipulate you into all kinds of things unless you’re consistently clever at poking holes in their hypothesis logic and test design. “Maybe you guys suck at hiring,” was my guess, but I entertained the idea of an SF experiment as a solution for accelerating hiring. Thus we opened up an SF satellite 6 months ago in Hiplead’soffice to test if this helped us hire salespeople. Adam said, “Wow, that was fast after you said you were going to do it,” a recurring theme in our moves. I forbade the non-sales team from venturing there and had strict rules of engagement around when and where meetings and candidates had to be, rules which my insubordinate team irritated me by increasingly flouting as they settled into SF. Brazen requests for catered lunch and dinner in the SF office to match the Main Office basics were admonished, “This is a test and we’re treating it as such so perks such as free food are not a priority.” After a few months, it did appear that our hiring pipeline was much improved, so we started the search for an SF office.

I optimized on one thing: being close to Caltrain to minimize marginalization of the South Bay loyalists who were having the rug pulled from under them. I checked the place our broker Brandon found closest to Caltrain and said we’d take it. Thus we’ve now moved into the one place I looked at because it best satisfied my Caltrain criteria by being literally across the street.

Looking back at the history of our office locations, from Google campus, to alternating days between the Mission and Mountain View with weekends at my house with Gemma cooking for everyone, to Menlo Park, to split between Menlo and Mission, to now everyone together in SOMA, I see consistent themes in our moves.

I’ve learned people care a lot about office location. Uncertainty and flux over office location was endlessly distracting for the team. I was pissed off by how people harassed me for information, lobbied, speculated, and irresponsibly promised SF timelines to team members. Part of me wanted to stay in South Bay so as to not seem to reward SF politicking, but I also blamed myself for not being 100% clear. I always had a soft spot for watching out for South Bay interests because they are uncomplaining and selfless about doing what’s best for the whole team, thus I optimized 100% for Caltrain and ignored Bart. I don’t know what this teaches anyone about interacting with me other than that I make decisions fast by focusing on what I want to optimize and I worry about sticking up for people who don’t stick up for themselves.

After the location factor, all our moves optimized for cost. Our gigantic space in Menlo Park was a great deal because our investors are generous and supportive. I learned a lesson from the various dead startups we got most of our fanciest furniture from: we did not want to live in an opulent palace as though we’d won when we were still in the midst of fighting a war.

The underlying theme is that we do what lets us increase velocity to hire the teammates we want to hire. Are you or someone you know a potential fit because I’d love to talk? Let me know your information! Also, our office warming is tonight. Come to 330 Townsend!


2016: A New Era

Hart asked if I still write. I do, but I can’t blog as openly about life because of work. War stories are classified. Part of me wishes we’d followed through with filming everything with GoPro necklaces so we could carve the 99% that’s talking to computers to expose the gristle of business drama. But what’s the point? Nothing’s like what anyone can tell you.

Apptimize crew sailing around San Francisco
Apptimize crew sailing around San Francisco

Much work is objectively boring and hard for a long time. That’s what it takes to win, tens of thousands of hours of work that more reasonable people are unwilling to endure. It takes a wizard every hour of every day for years and years alone in a dark tower to draw the spell to craft and mark a new world. It’s pain, loss, sweat, time, boredom, all while fervently believing you must triumph.

More and more, I find myself saying, “I can tell you more in person.” I’m swimming the strange intersection between business and personal, because a startup is water that touches every part of you. In the ocean you feel the reality of constant motion, relentlessly pushed, engulfed by the smell and sound of the heavy waves. Fixate on the mission and row with boundless energy, lest you’re wrecked instead of carried. All your customers and friends and teammates swim together, making the same waves.

The amount of change Apptimize has gone through this past year is staggering. We’ve all changed. I was always ambitious, but my drive was as nothing to my fresh hunger, now that I know more what’s possible. Interviewing an executive candidate, he said, “Your words make me restless,” probably a funny reaction to debating the nuances of sales pipeline definitions.

A year ago, Apptimize was totally different. We made less than our server costs. Much of the impossible stuff we did, we were only able to do because we had no idea what we were getting into. I’ve seen us get so much stronger operationally, starting with learning the difference between strategy, plans, and goals. We’ve rebuilt again and again. We’re now about 25 people, long past fitting around the dinner table at my house, even with all the leaves in.

I’m different. After my previous life of prop trading our own money, I realized I love sales and the responsibility of customers. After 30 years of disdain, I started wearing high heels. I bought a brass rat; maybe one day I will consider actual jewelry. I finally started drinking alcohol. I’m learning more how to wield my weirdness: once upon a time, minutes after meeting someone I’d be ENTJ-ing them towards increased efficacy. Now I give it more time.

The last time I changed a lot was when I moved from NYC to the Bay. That was hard because I loved NYC. No matter how deep you get, NYC shows you something that takes your breath away, realizing you didn’t begin to know her yet. Deep was my love was for New York, the people, myself. I’d take the train down weekends to see my mom in Princeton. When Mom died, one of my best friends since 6th grade drove into NYC from Pennsylvania and I took her to my favorite foods. I had no hunger for food. A few months later, I moved from NYC to Palo Alto because I felt useless. You can’t be useless.

An addiction, NYC poisoned SF for me. I’d plan clandestine visits around NYC wishing we could get back together if it’d change just 1 thing. I’d fantasize about a bicoastal relationship, a modern jetsetter, brimming with love for everyone and no one, ready to forsake town whenever it threatened to get tiresome.

What is a home? I find my home whereupon returning from a journey the smell of the street fills me with gladness and relief and I restrain my haste in knuckling keys into a door to find a friend waiting inside to swing me in her arms and bring me tea.

For the last 3 years I swore I couldn’t find such a home in SF. The homeless people: that’s one of the first shocks. It still astounds me, the looks on their faces, approval through our mute acceptance. I drown in disgust and shame for them, myself, all of us. I lash myself to the mast and sail through the tempest. I staunchly ignore them and consider my own fortune. I resolve, “One day I will fix this pain. I’m still getting stronger and one day this will be simple to correct.” I retort, “Another empty, foolish, impulsive promise.” I rationalize, “This isn’t the most important thing.” I anguish, “But how do you know?” How much can you harden your heart before you’re no longer human? How much can you reach back towards suffering before your life is no longer yours? Torn and bloodied I reel until another of my multitude rips me from the centrifuge, sighing in my ear, “Enough, enough.”

Contemptuous and hating SF, 3 years ago I moved from NYC to Palo Alto. The South Bay has its own sedate majesty. Driving down from SF it’s like descending from Mount Doom into an Eden of sweet, warm air. Understated and grand, even the woods are a suburban paradise. Everyone’s changing the world in their garage- NBD. I plucked giant, perfect fruit from yielding trees, sucking the juice from my wrist. But I can’t stay still no matter how comfortable and serene- onward, onward, pushed out of paradise by the waves of the world.

In December 2015, I moved from my house in Mountain View to an apartment in SF. It rained and the streets were unprepared so I took off my wet socks at Plow. My soaked book crumbled. It rained as we explored an abandoned nuclear site. Nick reassured, “I’ve been over this area with my geiger counter and it’s not that bad.” I like cold, I like temperamental weather, I like Land’s End, the way the wind blows the water white and black. I don’t live next to water or eucalyptus; I’m tabling that until after I settle this next thing with my business. Today I live in the Mission, a place Dan took me years ago and I instantly hated. Love blooms more lustily out of the ash of initial, prolonged dislike. Love: you don’t say it yet but you start thinking it. NYC has much of the best of today, but SF is the swan of our hopes for everything in 100 years.

That’s what you discover in a startup- even after sighting product market fit, you never stop pushing the market and product and reinventing everything. I love my startup. I love SF. Join my SF crew! Come away with us to navigate this life together! Shall we press forward together no matter how comfortable each stopping place is? Shall we strive and adventure together until we die?

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