Category: startups

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YCombinator Summer 2013

The first day we all talked about our startups was called “prototype day” and presented as “a 2 minute way to introduce yourselves to your batch mates, talk a little about your startups, and tell each other what you could help with. Don’t stress about it at all, guys!” I made 4 slides with 5 words total, went up there and told our batch mates they should use our product if they had an app, and that although I used to be in HFT they shouldn’t ask me for investment advice.
When I sat down, PG said, “I’m going to say it again- don’t talk too fast.”
Geoff Ralston added, “And don’t drift off without a conclusion.”

After everyone was done, PG said, “You guys should notice that you guys, like investors, favor the serious startups that talk about revenue.”
I was like, “I thought this was a way to introduce ourselves, not a mock pitch towards investors! Why did everyone else clearly spend a ton of time on their presentations and assume their target audience wasn’t their fellow batch mates! Don’t they have companies to run!”
At the bar later, my drunk batch mate came up and said, “Hey, you did good, you rolled with the punches.” At that moment, I decided to win YC.
“What does ‘winning YC’ mean?” Jeremy asked.
“We’ll figure it out!”

A few days later, this resolution disappeared into the swamp of my mind along with everything that wasn’t frantically fighting to surface. There was so much shit happening that demo day nauseously oscillated between seeming ages away and then sickeningly almost upon us. Part of me had believed that if we got into YCombinator, all of our problems would be solved. Spoiler: this didn’t happen. While there were office hours where in a moment of intense optimism one might muse, “Should we be charging each user $400 or do more marketing and charge each one $10?” conversations with users that revealed they had no idea what 90% of your product did would quickly smack us down into realizing we didn’t have the luxury to discuss these types of problems.

Pre-YC, I’d wondered, “I’ve read pg’s essays. I can emulate him somewhat in my brain. Do I really need to give him 7% of my company so I can talk w him for 20 minutes about my company, which I’ve thought about a lot more than he has?” Yes, yes I did.  He really is that good. PG actually loves you and wants your startup to do well and is undyingly optimistic that it can succeed despite whatever dumb thing you’re doing. He cares about founders and developers and that’s the reason he’s doing it. Every time I’ve posted to hacker news, he’s emailed accusing me of gaming his algorithms: that’s passion. He’s a fountain of secret data no one else knows and is a genius when it comes to knowing what different groups of people like VC’s or users want. After YC ended, I was talking with pg, “How did you know x would happen?” and he was like, “Duh, I’ve seen more than 520 startups.”

Some people you talk with about your startup and it’s obvious they don’t care about you and aren’t really thinking and are just saying whatever knee-jerk thing the first google hit would say. The YC partners aren’t like that. They are excited / terrified for you and think about your situation. Each partner has their thing they’re amazing at. They’ll walk through your product with you and tell you where it sucks. Our main guy Geoff Ralston told me what to say to different leads. Mike Seibel and Ammon told me about their AB testing dramas. Sam Altman gave me his number and coached me through meetings. Kevin Hale user tested Apptimize and told us exactly what to fix. I still have screenshots of our first iteration that we were so proud of and now find quaint. It’s amazing to have some of the best and most well connected people in the world look at your disgusting fetus of a product and tell you their real opinion.

This summer, my brain was remolded into Apptimize CEO-shape. I started dreaming about Apptimize. Apptimize became the reason I was cutting my nails and working out. My whole life I’d viewed running as extremely boring but now I run 7 or 8 miles every time because it’s an incredibly efficient form of exercise for Apptimize. Apptimize lets me do anything, no matter how boring or painful. Every piece of food I eat is an energy source directed towards Apptimize productivity. Everything I do is because I did linear algebra in my brain and decided the vectors were sufficiently aligned in an Apptimize-beneficial direction compared to the other choices to merit incorporating. Every product, app, technology I see exists in the context of Apptimize and my first reaction is generally how much better it’s going to be once we get our Apptimize mitts on it.

Although these shoes "look gay," as my fellow batchmate informed me, my knees start to hurt after mile 5 so I wanted to try them out. Let me know if you have running tips!
Although these shoes “look gay,” as my fellow batchmate informed me, my knees start to hurt after mile 5 so I wanted to try them out. Let me know if you have running tips!

A week before demo day, we had the office hours with Paul Graham where you talk about your demo day outline and he yells at you while wiggling his toes. “Why are you going on and on about product features? You’re certain to cause vc’s to immediately start checking their email.” Despite this help, our rehearsal day speech was insanely bad. PG said, “I only remember 1 factoid from this demo,” before immediately proving he didn’t even remember it accurately (although Jessica did).

I have better UX now- I guess that’s another thing I learned at YC. Demo day was about having UX optimized for a particular kind of user that you don’t normally engage with- a herd of top venture capitalists. PG is a genius at demo day UX design. Every normal person is extremely bad at it (How could any normal person possibly be good at it?). Our presentations were sooo bad before PG got his hands on them. For example, I assumed VC’s wanted to know what our product did. Our product is complicated and technical with numerous benefits and applications which features I spent minutes giving examples of. PG put a stop to that and patiently listened to 10 iterations of our demo until it was pounded into something memorable. We learned to emulate PG better, which was good because we kept changing stuff until the last minute. On demo day, PG (and everyone) was seeing 20% of our presentation for the first time. Luckily, it worked out! He said our demos were “significantly improved even from yesterday.” More than 100 kick-ass investors came up to me and asked about investing, including MC Hammer who also followed me on twitter, meaning now a significant percent of my followers are celebrities named MC Hammer.

Hammer approved the posting of this photo.
Hammer approved the posting of this photo.

We almost didn’t apply to YCombinator because 7% sounded like way too much of my company to give away to a bunch of people whose blogs I already read. I felt I could get the benefit of the advice in other, cheaper ways than giving them a chunk of my company. Like, I already knew a lot of YCombinator alums from MIT so I was already quasi part of the network anyway, right? Wrong! The network is amazing. When we were going through a confusing situation, I emailed a few companies who’d gone through something similar asking for a quick phone call, and it didn’t matter that they were running companies worth hundreds of millions or billions- they called to give me the real story behind what went down.

A month after YCombinator ended, I missed everyone so much I ordered the hoodie and iPhone case and other schwag that I generally eschew. The bonds coalesce after the program ends- we all felt like we didn’t get to know each other well enough during YCombinator because there was so much going on, but now we chat online and meet up in Palo Alto. I feel so inspired every time I talk with my batch mates. If you have an entrepreneurial bone in your body, apply here. YCombinator is awesome and easily worth it.

PG and Nancy at YC

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Founding Our Startup: All about the Team

“Do not do a startup,” they said. “Run a team within my fund. You can hire whoever you want and we’ll give you whatever you need. It’s the smart move.” Why would anyone want to start a company? For money? Seems like an unlikely way to get rich. For fun? Seems like you need to deal with an endless parade of annoying tasks, from legal to logistics to facilities to finance. Better to curl up inside a cozy mothership.

Well, we did it anyway! What have I been up to since GETCO? Jeremy and I started Apptimize and we’re in the current YCombinator class.

I went to Mark Cuban’s high school, but kid Nancy was not an enterprising go-getter who went door to door selling powdered milk; I was a bookworm hauling stacks back and forth from the library, making robots at nerd camp. Only when I stopped wanting to be a physicist did my path diverge from the ivory tower. Unlike entrepreneurship, in academia everything takes forever, there’s no feedback for a long time, you work in isolation if you like, and you don’t need to worry about anything outside your field. That sounded awesome to 17 year old Nancy because why not skip the unsavory, avoid the unlearned masses, and focus on what’s important, i.e. math and physics? But academia sucks. Sorry, PhD friends and Dad: although it sounded cool to be building a laser for a superconductor, I hated lab because nothing ever happened.

Startups don’t have that problem. In contrast, a main problem is deciding what to work on because there’s constant chaos. On top of that, you get emotional whiplash because one week your launch site is abysmally far from the first page of search results and the next week people are imploring you to let them email you their source code.

You can’t avoid any unappetizing arena when starting a company- startups eat pain. As Kevin described, “You are eating the huge shit sandwich that no one else wants to eat.” I am surprised to have volunteered for that, but that’s what Apptimize is- addressing a big, unmet need.

I decided to start a company when I realized people are crucial. I want to work with exactly the people I want to work with, and the best way to do this is to found a team. Everyone says the team is important, but, despite the pyramids and the Manhattan project, it took years to see why humans are social animals.

A smart kid, it was unquestionably more efficient for me to do everything alone than to involve others. During class, I would read the textbook and do the homework while everyone else did who knows what. I wished for clones or a time turner, but enlisting my peers rarely seemed useful. Short term, if you’re smart it’s easier to get good yourself than figuring out how to leverage others. This is great for the first few decades of life when there’s no emphasis on hard problems, but it doesn’t scale when you want to work on something bigger than homework (how sad that none expect a child to do anything cool).

No one builds a spaceship alone because building something great is too much work for 1 person, even an intelligent adult. Thus, executing on real stuff involves teamwork. The more ambitious the project, the more help you need. Why did it take decades to figure out something apes have known for millennia? I’ll blame our educational system because it’s so messed up it’s got to be at the root of all problems somehow. In real life, if individuals are fighting for limited resources, when a subset of those individuals team up to get those resources, the loners lose, and then everyone learns the lesson that teamwork is important. In school, the supposed rewards aren’t scarce, and the work is easy.

Although MIT was harder than high school, it was GETCO that inspired me regarding people. Knowing and liking the founders of my old company both as leaders and as dudes helped me realize: the main gap between founders and employees is that founders decided to be founders. That’s the difference between Washington and the other old guys in wigs, between Jobs and other nerds- people decide to be what they become.

I think of GETCO often- the people, the best part was always the people. Some of my warmest memories are of poker, swearing across the table, Shu urging everyone to drink while he sipped cranberry juice, challenging you to bet more money from off the table (do not agree to this (he will pull out a gangster wad of what first appears to be $10’s before he discards the ten to reveal $50’s mixed with $100’s)), the peer-pressure-induced re-straddles that led to people going all-in pre-flop blind with $1024 in a $1-2 game, Dan systematically re-buying to match the chip lead while dispassionately folding 90%+ of his hands, then offering massive bounties on guessing the next song picked by his iPod shuffle (always guess something by Johnny Cash). I’ve played a handful of poker games since GETCO, and despite my high hopes they’re never anywhere near as fun.

Knowing the drama teams of all sizes have, I feel so blessed to have my co-founder Jeremy. We are both determined, ambitious, critical, and honest. Otherwise we’re opposites. He’s apathetic to competition whereas I find it extremely motivating and exciting. He’s verbose and literal whereas I am terse and subtle. He instantly responds inline to each line of each email whereas I boomerang email for days on end. He avoids rooms of strangers whereas I love new friends and learning about another person. When we disagree, we interrupt each other with increasingly dramatic supporting evidence before eventually convincing each other and swapping sides. I’m encouraging Jeremy to switch from soda to kombucha and he persuaded me to get a car instead of renting from the airport. He’s attentive and polite, nudging me warningly when I openly space out during monologues.

After our YCombinator interview, I said, “I didn’t know if we’d get in!” and Paul Graham replied, “You seemed like an effective team.” How formidable! The Apptimize team loves data, commits to the truth, invites feedback, listens, constantly improves, and boldly experiments. Everyone is curious, creative, passionate, authentic, and generous. We have the best game nights! If I didn’t know the true spell, I’d use the glorious image of us all focused together working as my happy memory to cast my patronus. When you’re swinging for the fences, building an efficient team is critical to execution. That’s what our startup is, an amazing team!

Jeremy and Nancy, founders of Apptimize
Jeremy and Nancy, founders of Apptimize!

Jeremy grilling

 

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What to Work on When You Don’t Need to Work

The “need to work” has to do with responsibility. As a kid, my only responsibility was not getting too sticky from all the candy I ate, and my work habits reflected this. As an adult, I’m responsible for myself and my family, but I don’t have a bunch of bloodsucking kids yet and my work habits reflect this: I don’t do any work I don’t enjoy; if something pooped its pants in my presence, leaping into work mode is the last thing I’d consider.

If I view my responsibilities as only including myself and my family, then the amount of “work I need to do” is small, especially since almost everything I want money for is either relatively cheap or really expensive. The first time I realized this, it felt great! I felt like I had arrived. I could watch movies all the time and have my “work” be shopping and exercise so that upon my high school reunion everyone dies of jealousy when they see how my hotness has only increased with time.

Ages ago when I graduated from MIT and told Junot Diaz about my uncertainty for the future, he shook his head and smiled, “You have nothing to worry about.” Since he’s super into the apocalypse and the injustice of inequality, I interpreted this as an allusion to our living in an illusory first world ivory tower, but now I think he also referred to how big my safety net is, especially considering the marketability of my degree. Working a white collar job was the default mode for me, not like North Korean prisoners for whom bathing means waiting for weather warm enough to allow standing in the rain. Working on Wall Street is beyond their greatest dreams, whereas for me it’s a backup plan. A poor person in another country takes a risk by experimenting with fertilizers, and if it doesn’t work out his family starves to death. If I take a risk that doesn’t work out, I’ll just feel embarrassed and delete some old blog entires. There’s no comparison.

I’m not sure when I realized my relative lack of responsibility was an illusion. Maybe it was from hanging out with altruistic friends or reading HPMOR that got me feeling it was a mistake and a sin to only claim responsibility for my own comfort and curiosity. Maybe it was when I saw Wall-E wherein through technology the humans have achieved a state of, “Well, I could do this forever: eat, grow fat, watch tv.” We laugh at the obese humans who can’t even stand up, but we are actually at that state now in our wonderful, first world, welfare society, incapable of starving to death no matter how much we lie around. Are we going to live like those hapless humans or are we going to exhume the Earth?

How can I go shopping and movie hopping all day if I’m responsible for my species? When I mentally tested expanding the scope of responsibility beyond my personal welfare to include my fellow man, my first reaction was to groan, “Oh no.” Because the instant you have that thought experiment, the amount of work we need to accomplish balloons up monstrously. If I’m responsible for more than myself, then the “need to work” morphs into a dauntingly huge problem with a totally different scope. Being responsible for another individual could include cooking meals for them or paying their rent, but you can’t take care of a whole species through chores or even money. To scale, we need to do bigger things, invent stuff, use our imaginations. I never cook and I’m still figuring out how to take responsibility for my family. How do I take responsibility for my species? This is the question I’ve been thinking about. What do you work on when you need to work for your species?

A while ago, I realized it’s mathematically irrational for people who can afford to take big risks to not take them, and who’s better positioned to take risks than us? Furthermore, if you claim responsibility for your whole species, it’s not just irrational to not take a risk- it’s irresponsible and morally wrong. Unambitious ambitions are false to my identity and potential: our ambitions have to match our abilities, and most people are not reaching high enough- because of fear, laziness, lack of imagination, etc, which is wrong. It’s like the Dalai Llama or someone wise was saying: if we have greater will and intelligence than flies, but we live the same as a fly lives, then the fly is more true and honest than we are. I have a duty to myself to monotonically increase in awesomeness, and I have a duty to mankind to do good in the world. From this perspective, there’s no end to the work I need to do. Which is sort of annoying and scary, but also fun and exciting! Just as we have a duty to pursue personal excellence, we have a responsibility to live up to our potential as a species. We humans could live off the land like flies, but we build structures and satellites because otherwise intelligent dolphins and alien civilizations would laugh at us.

So here’s the question that Elon Musk caused me to ask: What do you think are the biggest challenges and opportunities facing mankind? This question has led to many awesome discussions, so think about it. The only catch is that after you think about it, the follow up question is, “What are you doing to contribute to a solution?” If the answer is, “Nothing,” then we have to ask, “Why are we choosing to work on something we don’t consider important?” So watch out: a question can change everything.

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The and My Future

“Why are you taking the 101? Can’t you see your iPhone 5 is lying to you? Its map was wrong in Santa Clara and it’s wrong here.”
“The 101 is the 280’s uglier sister. Clearly Steve jobs wanted us to take this route. Anyway now we can have a nice talk where you advise me on my finances.”
It’s funny how I’m the financial expert amongst my non-trading friends even though my opinions are almost certainly things no financial advisor would recommend to anyone.

When I first joined GETCO, I introduced myself to a new employee saying, “GETCO is my first job after MIT,” and the closest person I had to a boss interjected, “And your last.” At the time I sincerely believed and hoped that this would be true. In 2007, the company had 30 traders across 4 offices. Each trader did whatever they decided was optimal in a market that bloomed with opportunity: it was like the wild wild west- so much fertile terrain waiting to be conquered by a few explorers, populated only by some occasionally annoying but generally innocuous natives. I loved it. I never had someone telling me what to do, or really even anyone questioning what I was working on. I didn’t think about the future after GETCO because who would ever want to leave? The business was exploding, we were at the forefront of technology, and if you hesitated to size up your coworkers would make increasingly loud chicken sounds.

4.5 years later, after Singapore I went straight to my NYC desk to clean it out, then to Chicago to resign. I and everyone assumed I was going to stay in HFT because I’m a “world class expert in HFT,” plus headhunters were busy setting up lunches with billionaires with ambitions regarding their nonexistent/proto/growing/declining HFT operations. I was advised not to sign anything till the noncompete was up so I participated in some fantastic handshakes and told everyone I’d see them after my noncompete was over.

I’m not good at vacation so I viewed this year as a rumspringa world tour- I just got back from New Zealand and am writing this while jetlagged, thinking about how my paid vacation will be up in 2.5 weeks. This year I zoomed my head out of focus to see what everyone else is looking at. Let me tell you: Other People are looking at some pretty crazy stuff. I met Verner Vinge and Ray Kurzweil at the Singularity Summit. Compared to these impassioned singularity people, I feel like an ape for mentally shrugging when they bring up existential risk and AI. Nevertheless, my main impression is it’s cool these people are contemplating and perhaps helping decide a vision of mankind as a species. Most people never think about that kind of thing, as individuals or as a species. What is the destiny of mankind? Who even asks this question? Shouldn’t we wander blindly towards our fates like all other species? Aren’t we just dominant, blessed by god to be gods among animals? Anyway, the Singularity Summit led me to go to Rationality camp. This post was originally about Rationality Camp but I guess I’ll write about that some other time (sorry to leave you as irrational as ever, although I can tell you that I made $280+ from poker, won a prize despite not being the most rational (Dilip had the most points in the whole camp but somehow lost his prize to me. Yes! Plus I beat him at some kind of augmented reality game, which victories are documented photographically)).

This year has been upside down: I’ve been paid to not work, spent more time in CA than NYC, and I realized I’m old- I think I’ve aged relative to my non-finance peers. I’m 27 and I’ve started finding younger people annoying. Those fools have no idea how lucky they are. At my age, people are suddenly so hard to impress. If I were starting a company at age 17 people would say, “Awesome.” Now everyone’s like, “Whatever.” Too old to be effortlessly impressive, too young to shove offending kids off my subway seat, I’m at an age when I don’t really notice anyone else’s age unless they bring it up, whereas for years I was conscious of even a year’s difference. Looking back at my childhood, the hours reading in the grass, the biking with friends, my main impression is that an idyllic childhood is a colossal waste of time. Yes, even the priceless hours bonding with family had diminishing returns, and no one really needs to read the collected works of anybody- very few writers have anything to say after their first real book.

Sometimes I see flashes of myself 10 years in the future, so clear it’s almost a memory. This year I started seeing what future Nancy would be if I kept going down the trading path, and I didn’t feel excited. In fact I felt bored. Because it’s basically the same as always, except I’d need increasingly larger sums to get the same level of stimulation. For someone who lives so much in the future, I hadn’t really thought about what I’d think about the future after (if) it already happened. When I’m 40 will I see my 20’s and 30’s the way I currently see my childhood- objectively successful by most measures but privately viewed by myself as largely a waste of time?

I feel ennui regarding the kind of stuff people are supposed to do in their late 20’s, early 30s: the house and marriage stuff. My mom was in constant turmoil over the fact that she was too sick to see me “settled” in my NYC apartment. Prior to NYC, she had “settled” me into all apartments I’d ever lived in. Perhaps out of a desire to do what I thought she’d want me to do, I went out and bought my first furniture since she forced me to buy my mattress 5 years ago when I first moved to Chicago and needed a non dorm issued mattress. I ended up buying a $5000 coffee table made from a single solid cross section of a gigantic tree. Maybe I thought my mom would rest assured in my competence if I showed her this coffee table and other furnitures, that I was a grown up and finally handling this kind of stuff. I think I even bought a house plant of some kind, which never would have occurred to me to do in my youth. Mom just wanted me to be happy, which might not be what I want for myself. Now that I know what it’s like to have the perfect set of plates, I never want to own plates again. That stuff is all at my dad’s house now, completely out of place with his ornate, plasticky furniture.

I think I might’ve reassessed my trajectory sooner if it weren’t for the parents’ cancers. Cancer put me in a mental state of martial law where I was single-mindedly attacking obstacles without considering the problems of philosophy- who cares about higher ambitions when it’s life or death?

Now I feel like there’s more pressure. Maybe this is true for us as a species too- just as we’re most successful, there’s the most danger. Humans have accomplished a lot relative to other animals so the universe is ours to lose, plus we have to decide the extent of our future ambition. Similarly, as a kid the difference between working a little and a lot was the difference between an A- and an A+, whereas now there’s so much at stake- it’s now the difference between losing money and making money.

I’m acutely aware of being the writer of not only my writing but also of my own life. It’s exciting and scary and writer’s block-inducing to decide the next act. But from my life there’s just one thing I ask: don’t tell me how it ends.