• The evolution of UI/UX in enterprise companies, illustrated with GIFs.

    This post was originally published on Medium in 2015.

    The value of design in a consumer app is fairly well appreciated today— design, branding, and user experience have a meaningful impact on customer happiness and retention.

    For enterprise companies, however, it would be easy to underestimate the power of design. Many of these tools operate behind the scenes or on a server farm, so visual design isn’t a priority.

    Yet some of the best enterprise companies took design to heart. Their websites are an extension of their brand, and they use design to personify an otherwise faceless product. Stalwarts like Oracle and SAP might not have the most attractive sites, but new players leverage design to connect with their customers and differentiate themselves from their older and slower competitors:


    Some takeaways for enterprise companies:

    1. Plan an annual redesign. Most of the sites above completely overhauled their websites at least once a year. While some of the changes are visual, the general UX of the page also improves. A lot changes in the design world in a year’s time, and a lot also changes in enterprise. Redesign your site to reflect that.
    2. Photos of people help humanize your brand. Some of the above use stock photos (e.g. VMware), others use custom photos (e.g. Rackspace), and others use illustrated people (e.g. Joyent). In every case though, it seems like the company is trying to put a human touch on an otherwise amorphous product offering.

    3. Today, whitespace, color, and photos are preferred over dense text. This is partly a broader web design trend, but even enterprise companies that have complex offerings are putting documentation and features on separate pages, leaving the homepage free for calls-to-action, customer testimonials, and eye-catching photos. Consider Salesforce’s site in 2010, VMware’s site in 2010, or Heroku’s site in 2012 versus their sites today.


    If you found this post interesting, take a look at Bowery. We’re reinventing the local development environment, and it’s free.

  • Last spring, I took a class on social psychology. It was one of the most useful classes I’ve ever taken, so I figured I’d share some of the more interesting findings. Each paragraph has a citation to its right so you can get more information or read the original study.


    1. Reciprocity has a strong effect on us.

    20% of people send Christmas cards back to people they’ve never met, just because they received one from them. For the same reason, tips to waiters go up 3.3% when an after-dinner mint is provided with the receipt. And when the server looked the diner in the eye and gave them a second mint? Tips went up 20%.

    2. You attribute a higher value to things you already own—this is known as the endowment effect.

    Willingness to sell was twice as high as willingness to pay in one study. In other words, participants were willing to buy a mug for $5, but once they owned it, they wouldn’t sell for less than $10.

    3. Heat makes us angry, and sadness physically makes us colder.

    When you feel rejected, you report the room as being colder and you prefer warmer foods over colder foods. Crime rates are higher in hotter regions, and crime is more likely on warmer days. Baseball pitchers are more likely to hit batters when it’s hot. This occurs because heat causes arousal, but people misattribute that arousal to situations around them and not to the heat.

    Duchenne smiles (example B) that are exhibited in high school yearbook photos are correlated with better life outcomes 30 years later. Here, Paul Ekman—an expert in facial psychology—exhibits both non-Duchenne (exhibit A) and Duchenne smiles.

    4. Smiling is contagious—and can predict your happiness, professional success, and lifespan.

    Humans laugh more at movies when other people laugh. Additionally, many people smile at getting a strike in bowling only after they turn around to their friends—you smile for the social approval, not for doing something successfully. In another study, students who exhibited “Duchenne smiles”—a more authentic type of smile that engages the eye and mouth muscles—in their high school yearbook were more likely to get married and were more likely to self-describe as “happy” 30 years later. Students with less intense smiles were more likely to be divorced. And in any given year, people who exhibited Duchenne smiles in their high school yearbook were half as likely to die.

    5. How we’re approached and our desire to be consistent affect our decisions.

    If I asked you to volunteer for an “Experiment at 7AM,” would you do it? What about a “7AM experiment”? 56% of people asked to volunteer for the first did so, but only 24% volunteered for a “7AM experiment”—fewer people want to wake up early, so the ordering of the words matters. In another experiment, some participants were called and asked if they would hypothetically volunteer for the American Cancer Society. When they were contacted a few days later and asked to volunteer, 31% agreed—versus 4% of people who were cold-called and asked to volunteer for the first time.

    6. We act differently when reminded of who we are.

    When participants were told that men and women scored differently on a particular test, female participants’ performance dropped dramatically. Male participants’ performance on a task dropped after interacting with an attractive female participant. When children are in a group on Halloween, they take more candy on average—but when children were singled out and asked their names, they took far less candy.

    7. Being watched sometimes helps—except when eating.

    Having an audience of people watching you complete a task improves performance on simple tasks but hinders performance on more complex tasks or when learning a new skill (they showed this with both humans and cockroaches—don’t ask). The mere presence of someone in the room causes this effect; even a repairman working on something in the corner slowed people down. Yet when it comes to eating, a full chicken will overeat in the presence of another chicken, and animals eat more in pairs than when alone.

    8. Comparing people to their friends is the most effective way to make them do something.

    When an electric company tried to encourage people to save energy at home, telling them “your neighbors are reducing their energy use” led to a 2% reduction in household usage. Telling people “save energy to save money” or “save energy to save the environment” did not decrease, and in some cases increased, energy usage.

    9. Context—where we do something—has a substantive effect on what we do.

    56% of actual voters voted for a pro-school budget when voting in a school vs. 53% otherwise. While that effect may not seem huge, it’s statistically significant and was reproduced in a lab environment (64% of people voted for a fake pro-school budget when shown pictures of a school vs. 56% who voted for it otherwise).

    10. The more you’re exposed to something, the more you like it—this is called the mere exposure effect, and it works in milliseconds.

    Participants shown a foreign word frequently were more likely to say the word had a positive connotation. The most immediate application of this effect is advertising; the more often you’re exposed to a commercial or ad, the more positively you will rate the company. Flashing images that elicit positive or negative emotions for only a few milliseconds subliminally conditions your attitude.

    People liked familiar objects more than abstract patterns, but in both cases participants overwhelmingly preferred curved objects over objects with sharp edges. Objects in category C (featuring both curves and edges) fell in between.

    11. Curves > Edges.

    Humans overwhelmingly prefer curved visual objects over objects with jagged lines.

    12. Don’t get hurt when there are a lot of people around you.

    Bystanders are less likely to intervene in a crime or help in an emergency as the number of observers increases, as each individual feels that someone else will help and responsibility is diffused. When a victim is bloody, people help less often—likely because there is a chance they would be exposed to pathogens. But victims who scream receive more help than those who don’t—clear and unambiguous danger is helped far more often than not.

    13. We really want to be happy, but being too happy can negatively affect our work.

    In a study of 10,000 participants from 48 different countries, happiness is rated as more important than any other personal outcome—more than finding meaning in life, becoming rich, or getting into heaven. Happy people more often label themselves as “curious,” and depressed people are more likely to notice small changes in facial expressions. Yet extremely happy people (9/10 or 10/10 on a happy scale) got worse grades and had lower salaries than moderately happy people (6/10, 7/10, or 8/10 on a happy scale).

    14. We do stupid things because we want to conform.

    In one study, a participant was placed in a group and asked to answer a seemingly simple question. The rest of the people in the group were all told to respond with the same incorrect answer to the question, after which the participant was asked to answer in front of the group. 37 of 50 participants gave the same incorrect answer as the rest of the group (even though it was very clearly wrong), either because they wanted to be “liked” by the group or because they thought the rest of the group was more informed than they. This effect was dampened by having just one other person in the group agree with the participant.

    15. We have trouble separating out traits in a person.

    Globally positive or negative reactions on a person (“he’s a nice guy”) affect our judgment of a person’s specific traits (“he’s attractive”). This is called the halo effect, and is particularly noticeable in celebrities; their attractiveness or fame also leads us to believe they’re intelligent, happy, or honest.

    16. We’re influenced by very particular types of rewards.

    Expected rewards reduce motivation on a task. Surprise rewards increase motivation on the same task. Fixed rewards are less powerful than performance-based rewards, even with creative tasks.

    17. Authority can fundamentally change our emotions and behavior.

    In the Stanford Prison experiment, participants were split into prisoners and guards and placed into a mock prison. In just six days (of a planned two weeks), the experiment had to be shut down because guards were harassing and abusing prisoners, and prisoners began showing signs of emotional breakdown.

    65% of participants knowingly delivered a lethal dose of electricity to a participant (who they later learned was fake) simply because the instructor in the room told them to.

    18. Authority can also make us be obedient and do things to other people we could never imagine.

    In the famous Milgram experiment, participants were told to administer a shock of increasing strength when a participant in another room gave incorrect answers to a series of questions. About halfway through, the shocks were labeled “danger: severe shock” and a recording was played begging the experimenter to stop the experiment. Yet in 63% of cases, the participant administered the maximum shock, even when the person they thought they were administering a lethal dose of electric shock to another human being.

    A recreation of the original Stanford Marshmallow experiment is predictably adorable. Longitudinal studies have shown that students who can resist eating the marshmallow are better behaved and get better grades later in life.

    19. Self-control at an early age might be indicative of success later in life.

    In the famous Stanford marshmallow experiment, a group of children participants were asked to wait in a room with a table full of marshmallows and cookies. If they wanted, they could have one treat now and the experiment would be over. Otherwise, if they could wait for the experimenter to return in a few minutes, they could have two treats. The children who couldn’t delay their urges—either they asked for the treat right away, or tried to sneakily eat a treat when the experimenter left—had more behavior problems, lower SAT scores, more trouble paying attention in school, and found it difficult to maintain friendships. In fact, a child who could wait 15 minutes scored 210 points higher on the SAT than children who could wait only 30 seconds.

    20. People aspire to round number goals.

    I tried to make this list 20 bullet points long instead of 19, and you do the same thing when trying to run 2.0 miles instead of 1.9. In Major League Baseball, players were four times as likely to end the season with a 0.300 batting average than 0.299. And when looking at over 4 million SAT scores, students who scored a 1290 were more likely to retake the test than students who scored a 1300—even though admissions offices did not statistically favor one score over the other.

  • Rhetoric and Speech in the Clinton Administration.

    This post was originally published on Medium in 2013.

    Below is an abbreviated version of an essay I wrote on Bill Clinton, his administration, and how rhetoric saved his presidency. Before the essay though, I wanted to include some choice quotes I found in my research that didn’t make it into the paper.

    Any president would rather receive and reply as Clinton did at a town hall meeting:

    Q: Hello, Mr. President—President Clinton. My question is, my birthday is tomorrow and I’m twelve years old tomorrow, and my question is, what kind of future am I going to have in store for me and the country?

    The President: That’s a neat question, isn’t it? (Laughter) I think you’ve got a very bright future. The world you will live in will be freer of the threat of total destruction than any world we’ve ever known.


    The hottest moment of the town meeting came when the president abandoned his usual empathic style and directly confronted a questioner.

    Questioner: Mr. President, in 1993 when interest rates were declining, your administration took credit for that. But now both long- and short-term rates are higher than when you took office. Will your administration now take responsibility for higher rates?

    The President: Why do you think they went up?

    Questioner: Well, I’m asking you.

    The President: I’m asking you. You asked me to take responsibility, so I ask you why. They plainly went down after we declared our deficit reduction package. That’s why they went down. They have gone up, I think, for two reasons, maybe three.


    Oral history interviews confirm that Clinton often did work on speeches up to the very moment of their delivery—and indeed would often extemporize while speaking. The story of the teleprompter and the healthcare speech is recounted in George Stephanopoulos, “All Too Human: A Political Education”. The wrong speech was initially loaded into the teleprompter], an accident brought on by the fact that the text was being worked on so late that no time was left to check the process. For several minutes, Clinton was forced to speak before a national television audience while an alphabet soup of verbiage spooled past his eyes on the teleprompter screens.


    Peggy Noonan takes us closer to the answer to the Clinton paradox:

    “Never tongue-tied and never eloquent—six years into his presidency, his only candidates for Bartlett’s are ‘I didn’t inhale’ and ‘The era of big government is over’—his easy facility is a two-edged sword. While it suggests a certain command, it also highlights Clinton’s prime perceptual problem: that he is too fluid, too smooth, like a real estate salesman talking to a walk-in with a Rolex.

    Now, onto the essay.


    President Bill Clinton is a case study in the power of the rhetorical presidency.

    Richard Neustadt, in his Presidential Power and the Modern Presidents, describes presidents as formidable leaders who use their power to persuade. Yet Bill Clinton was not a towering, unopposed president. He served at a crossroads—the Cold War had just ended; the Internet, cable news, and consequent shorter news cycles were just becoming mainstream; and during his tenure Congressional opposition threatened the presidency in unprecedented ways.

    Compounding these larger trends, Clinton suffered what most pundits believed would be a debilitating scandal, yet left the office with one of the highest approval ratings of any president in modern times.

    “How can a man lie multiple times, cheat on his wife, commit perjury, and become one of the most popular presidents of recent history?”

    Clinton surmounted these challenges through his extraordinary use of presidential rhetorical power. To his supporters, Clinton seemed to have the magical ability to relate to anyone; to his opponents, Clinton’s magic was the seduction of the American people. The Clinton presidency demonstrates the importance of the Presidential bully pulpit—while his rhetoric shifted from at first attempting to directly reach citizens to eventually acknowledging the press’ role in spreading his message, Clinton’s legacy survived because he converted his rhetorical talent into political capital.

    Clinton’s rhetoric was unusually powerful because of its conversational style. As Clinton’s head speechwriter Michael Waldman remembers, “his strength was never soaring rhetoric”—thirty minute speeches were reduced into half the time, and new speechwriters were warned he took “Hemingway [and turned it] into Faulkner. Rather, Clinton’s powerful gift at communicating grew from the intensity of his connection to the audience before him….He might dutifully read along with the prepared draft. Then, when he sensed the listeners were with him, or were resisting, he would leave the text, start dropping his consonants, and loop around and around the subject, trying to persuade the audience until he had won the point.” After winning the presidency largely based on his rhetorical gifts in town halls and conversations with voters, Clinton was poised to benefit from and depend on rhetoric once in office.

    President Clinton’s first 100 days in office aimed to leverage this strength. Under Clinton, “speechwriters were once again privy to policymaking and political strategy,” reversing a pattern by previous presidents of pushing speechwriters out of the decision-making process. Speechwriters reported directly to the Chief of Staff and the President himself. Clinton gave 550 speeches in a typical year—nearly double the 320 President Reagan gave per year. In the two years between his inauguration and the first midterm elections, Clinton traveled to almost two hundred town halls across the country.

    These events were meant to sell the President’s healthcare bill, his vision for the country, and the Democratic Party. Clinton thrived in the town hall environment—the “relaxed questions he received” there allowed his enthusiasm for “spontaneous give-and take” to shine through. Clinton’s rhetorical strategy was to “bypass traditional journalist mediation between leaders and citizens” because he believed “journalists were gaining more influence over political and campaign agendas.” Given Clinton’s rhetorical talent, his administration’s strategy hoped to forge connections with voters and circumvent conventional media.

    Even after news organizations helped spread Clinton’s campaign message, the new administration failed to appreciate how conventional media helps presidents communicate once elected. President Clinton, like Presidents Eisenhower, Nixon, Carter, and Reagan before him, held the press at arm’s length and mainly spoke to press at more formal, controlled events. In a stunning rebuke of conventional media, Clinton held a question and answer session with schoolchildren visiting the White House before he ever appeared before the White House press corps. Within three weeks of taking office, Clinton had spoken with live studio audiences in four separate cities via satellite, but had still not held a formal press conference.

    When asked by the Radio and Television Correspondents Association why he shied away from press conferences, Clinton answered, “Because Larry King has liberated me from you by giving me to the American people directly.”

    The President opted for more intimate events, like one-on-one interviews with Larry King or town hall meetings, that allowed his unique talent for casual rhetoric to dominate.

    This strategy unexpectedly backfired for the Clinton administration. His signature healthcare bill failed in Congress, his poll numbers dropped, and Republicans took control of the House of Representatives in the midterm elections. Clinton’s favored town hall format was quickly abandoned as “the format increasingly became a forum for negative and confrontational interactions between citizens and the president, providing fodder for negative national news.” Yet despite these defeats, “Clinton never gave up on the idea that all he needed was a few more speeches, or a slightly better message. ‘I’ve got to…spend more time communicating with the American people,’ the President said in a 1994 interview….It seems never to have occurred to him or his staff that his basic strategy may have been inherently flawed.”

    Clinton initially blamed his waning support on the negative press he had been receiving, not on his rhetorical strategy. When asked by Rolling Stone how he would respond to a disappointed supporter, Clinton responded angrily, “that man has a false impression of me because of the way this administration has been covered. It is wrong. I have fought my guts out for that guy, and if he doesn’t know it, it’s not my fault.” In June of 1993, Clinton realized “the level of acrimony” between his administration and the press was self-defeating—“clearly harm was being done.” With the public losing faith in his leadership, he brought in David Gergen—who had helped Presidents Nixon, Ford, and Reagan with their communications strategies—to forge a new path.

    If Clinton’s first 100 days are the story of his rhetorical strategy failing to understand political and media realities, the Monica Lewinsky scandal is the story of the media failing to understand the power of Clinton’s rhetoric. Just days before the State of the Union, news of the affair broke in the press. According to Clinton’s head speechwriter at the time, the President and his administration decided he would not address the scandal at all in his speech; they wanted Clinton to use his rhetoric to put the administration back on message. And indeed, “Clinton went on to save his presidency with a rousing State of the Union address in which he secured public favor by sternly demanding that Congress ‘save Social Security’.”

    The resulting post-speech approval boost—by some measures, as much as 16%—carried him through the scandal to the end of his administration. In fact, Clinton’s approval rating never fell below 60% during the scandal and hit a high of 73% twice—once on the day the House voted to impeach Clinton, and again when the Senate voted to acquit. Despite the fact that nearly half of all stories about the Clinton administration in the three months after the scandal broke focused on the affair, the scandal provided a reason for additional coverage of the administration, which often included other positive coverage of Clinton’s policies and agenda. By staying on message, the Clinton White House leveraged the negative press to more frequently present their issues.

    With the scandal’s spotlight on him, Clinton used the media frenzy to showcase his rhetorical power, this time in conjunction with the press instead of in opposition to it. The day before the State of the Union, Hillary Clinton and Vice President Al Gore hosted a press conference on afterschool education programs. At the last minute, speechwriters were told the President would deliver remarks on education at the gathering, with the unstated goal of making a statement about the Lewinsky scandal as well. They hurriedly “spliced the entire education section straight out of the State of the Union address and turned it into a statement.” Those remarks—containing the President’s education vision for the next year—were presented to a live audience “larger than for the State of the Union itself.” The President used the scandal as a soapbox to elevate issues that affected the American people, and they in turn rewarded him with unwavering approval ratings above 60%.

    Despite initially miscalculating how to deliver his rhetoric to the American people, Clinton’s rhetoric successfully elevated the office of the president and inspired the American public. He successfully used his rhetorical talent to craft a rhetorical presidency that furthered his administrative and legislative goals, a success reflected in unwaveringly high approval ratings throughout the Monica Lewinsky scandal. Once he applied rhetoric through existing media channels, rhetoric proved to be one of his most powerful assets.

    “It was a new kind of presidency, less dependent on legislation, more rooted in a president’s unique power to act and to speak. With his stream of speeches and announcements, he was trying, bit by bit, to restore public confidence in government, to show that it could get things done… This will most likely be his lasting legacy: redefining the role of government and then successfully convincing the public to share that vision.”

    To President Clinton, the rhetorical presidency was the presidency.

    Works Cited

    Denton, Robert E., and Rachel L. Holloway. Images, Scandal, and Communication Strategies of the Clinton Presidency. Westport, Conn.: Praeger, 2003. Print.

    Dorsey, Leroy G. The Presidency and Rhetorical Leadership. College Station: Texas A & M University Press, 2002. Print.

    Friedman, Jeffrey. “A “Weapon in the Hands of the People”: The Rhetorical Presidency in Historical and Conceptual Context.” Critical Review. N.p., n.d. Web. 14 Oct. 2013. www.criticalreview.com/crf/pdfs/Friedman_19_2_3.pdf

    Klein, Ezra. “The Unpersuaded: Who Listens to a President?.” The New Yorker. N.p., 19 Mar. 2012. Web. 13 Oct. 2013. [www.newyorker.com/reporting…](http://www.newyorker.com/reporting/2012/03/19/120319fa_fact_klein?currentPage=all)

    Renshon, Stanley Allen. The Clinton Presidency: Campaigning, Governing, and the Psychology of Leadership. Boulder: Westview Press, 1995. Print.

    Waldman, Michael. POTUS Speaks: Finding the Words that Defined the Clinton Presidency. New York: Simon & Schuster, 2000. Print.


    In a speech to the Democratic Nation Committee in 1999, he waxed poetic:

    “And let me just close with this story. I want to tell you a story that I thought about that I told the folks at home when I went to dedicate my birthplace. Last year I had a 91-year-old great uncle who died. He was my grandmother’s brother. And I loved him very much, and he helped to raise me when my mother was widowed and went off to study so she could be a nurse anesthetist, and my grandparents were raising me.

    And this old man and I were close from the time I was born. He and his wife were married for over 50 years, and she came down with Alzheimer’s. And they had one of these old-fashioned houses with gas stoves, so they had to take her to the local nursing facility that was tied to our nursing home in this little town because they were afraid she’d turn on the stove and forget about it and blow the house up. We can laugh—we all laughed about it. It’s okay to laugh. I’ve lost two relatives to Alzheimer’s. You have to laugh to keep from crying half the time…”

    Two paragraphs, 224 words, and a lot of laughter later, Clinton was still at his story, with no end in sight. I cite the rest of the speech not for its significance but for its pointlessness:

    “So I went to see him one night, about 10 years ago, after his wife went into this nursing home. And they’d been married over 50 years. And the first 20 or 30 minutes we talked, all he did was tell me jokes and tell me stories and think about the old days. And I was walking out and for the only time in our life, he grabbed me by the arm. And I looked around and he had big old tears in his eyes. And I said, ‘This is really hard on you, isn’t it.’ And he said this, he said, ‘Yes, it is. But,’ he said, ‘you know, I signed on for the whole load, and most of it was pretty good.’

    When you were up there singing ‘Stand By Me’ tonight and I thought about how the American people have stood by me through thick and thin, I would just like to say to all of you, when I talk about community, that’s what I mean. [Applause] Now, wait a minute. You don’t have to sit down, because I’m nearly through. [Laughter] Don’t sit down. Don’t sit down. I’m nearly through. Here’s the point I want to make: The reason I wanted you to come here tonight, the reason I’m thankful for your contributions, the reason I’m thankful for what you do is, this country has got to get over believing that our political life is about beating each other up and hurting people, instead of lifting people up and bringing them together. That is what I’ve tried to do. That is what we stand for. And if we remember that, we’re going to do just fine in the 21st century.

    Thank you, and God bless you.”

  • Why you should spend your 3 college summers in New York, San Francisco, and Boston.

    This post was originally published on Medium in 2013.

    There’s something to be said about trying different industries or roles each summer while you’re in college. There’s also something to be said for living somewhere different each time.

    The college summer is a sacred time. Yes, it’s prime time for relaxation before another stressful school year, but it’s also one of the biggest opportunities you have to explore new fields and develop yourself professionally.

    Boston in the summer is a special place. With thousands of college students gone, an otherwise bustling city is made calm. A town full of academics and business leaders suddenly has more time for coffee meetings and advice.

    Time spent in San Francisco is the best way to learn the ins and outs of technology, despite being unreasonably cold for the entire summer. Nowhere else can you walk down the street and see the offices and founders of companies you admire.

    But there’s a special place in my heart for New York City summers. The cool nights, the sound of ice cream trucks, and the blisteringly hot subway tunnels give the city its character. You won’t find the same density of students in the same diversity of fields and industries as you will in New York.

    After spending my freshman summer in Boston, my sophomore summer in New York, and my junior summer in San Francisco, I have a new appreciation for each city.

    Don’t stick in the same city for your summers in college—travel and try living in a new city. Half of exploring during the summer is finding what you want to do after college. The other half is finding out where you want to do it.

  • This post was originally published on Medium in 2013.

    In high school I organized a large conference for 1000+ attendees. I managed a $20,000 budget and a team of ~15 other students, planning 6 months in advance for a 2 day event.

    Event planning might be the closest you can get to starting a company. You have people counting on you, you have a set of constraints, and despite months or years of planning, Murphy’s Law always seems to take hold.

    Remember Eyjafjallajökull? It decided to rain ash across all of Europe as a box of 1000 gift bags for our attendees was on a freighter en route to New York. Lunch was an hour late. Ice cream melted in the unseasonably warm weather. Our registration system went down when the internet connection in the venue slowed to a crawl. People were lost in the building because of poor signage.

    So much for planning.

    I don’t care how smart or experienced you are, how long you have to plan, or how many people you have helping you. When something goes wrong—when everything goes wrong—your success depends on how well you can adapt and fix things. You need to be more MacGyver than Nate Silver, more Jack Bauer than Sherlock.

    Problem-solving is a muscle, and just like muscles in your body there are slow-twitch and fast-twitch decisions. Engineers are great at analyzing problems over long periods of time. Trying to decide what car to buy or what framework will be most efficient? We can systematically analyze the data we have to come to a best guess. But how well do you behave under pressure? Can you find a bug in under a minute when it’s preventing millions of users from logging in? How do you respond when you have 1000 people waiting for lunch and the delivery truck is stuck in traffic?

    Things always go wrong. How quickly you make those snap decisions is all that matters.

  • On big decisions and the next two years.

    This post was originally published on Medium in 2013.

    Today I have the honor to announce a major step in my life—after several months of applications and a few weeks of heavy consideration, I’ll be taking at least 2 years off from Harvard in December to be a member of the Thiel 20 Under 20 Fellowship. The first of many thanks go to the Thiel Foundation for giving me this opportunity and giving me their stamp of approval—it’s been an amazing interview process and I couldn’t be happier to be a part of the Thiel Fellowship community.

    It wasn’t an easy decision to make, but I think my situation is unique. I’ve wanted to work full-time on education for a while, and I’ve been enveloped in entrepreneurship for the past few years. My mom is a teacher and my dad is a self-employed programmer. I’ve been breathing education since I could walk and designed my first website in 4th grade. It’s about time I put those skills to good use.

    After reflecting on where I’ve been and where I hope to be, it’s clear that 99% of where I am can be attributed to other people. Amazing people who took bets on me when they shouldn’t have, people who cared enough to reach out to me, people who I could call at any time for help. Tony Tjan, in his book Heart, Smarts, Guts, and Luck, helps entrepreneurs determine what their core skill set is, and by his assessment I’m overwhelmingly luck-dominant. Let me take this time, then, to thank everyone who has helped me to this point, and in doing so describe how I got here.


    My mom came to this country in high school from Cyprus after having spent time in London. Her father was a farmer and construction worker and her mother worked with textiles sewing clothing. My dad studied computer science and accounting in Egypt, then spent several years as a farmhand and sous chef in Spain and France before coming to the United States. Here, he continued studying engineering and computer science, working full-time and going to school on nights and weekends. My parents met at the City University of New York and got married a few years later. They’re the hardest working people I know, and I wouldn’t be here today without the many sacrifices they made for my education.

    By 1985 or so, my mom was a first-grade teacher in a New York City public school. (She still teaches in that same first-grade classroom, and has been teaching for 28 years.) Since both my parents worked full-time, I spent the first few years of my life in a crib in the back of her classroom. (I was a well-behaved baby.) I then enrolled in that same East Harlem, New York public school as a student. Through years of their hard work, long nights, and 4-hour commutes to and from Long Island into New York City, I was contacted as a fifth grader by an organization called Prep for Prep that helps minority students get accepted into private schools. After going through several steps of interviews and being accepted, I spent 14 months going to night classes studying U.S. History, Biology, Latin,and more. I wouldn’t be where I am today without Prep—thanks to Charles Guerrero, Katy Bordonaro, and the rest of the team there for all the work they do.

    After what I still consider to be the hardest academic experience of my life, I was accepted to Collegiate School, a small all-boys school on the Upper West Side. I realized there that I loved my extracurriculars above all else. I organized an environmental conference for 1000+ attendees and a $15,000+ budget. Event planning is the closest job to being a CEO I know. Everything that can go wrong will go wrong, and you absolutely need to think on your feet. Collegiate gave me the freedom to explore what I was interested in—thank you to Mrs. Foley, Dr. Beall, Mr. Hill, Mr. Gordon, and the million other teachers there who were my biggest academic and professional critics. Collegiate was my launchpad to Harvard and I can’t wait to give back to it in every way I can.


    I didn’t come to Harvard as an entrepreneur, but I knew I wanted to study computer science. This was the first computer I ever used:

    My dad wrote a game that helped me learn the alphabet on that machine, and computers were always around the house since he was a programmer. I wrote my first program in Visual Basic and wrote my first HTML code back in 4th grade for my own little company, Blue Box Software (the logo was suspiciously similar to today’s Dropbox logo). I took two Harvard Summer School classes in computer science and was hooked since then.

    Here at Harvard, I got involved with Hack Harvard and the Innovation Lab at just the right time. Interest in entrepreneurship was beginning to pick up, so I had the opportunity to learn from some of the best startup leaders around and help fellow students who were also interested in the tech world.

    So, thank you to the Innovation Lab—Gordon, Neal, Kate—for your support and mentorship over the past few years. Thanks to Harvard for accelerating my growth and helping to introduce me to some of the brightest minds in technology. Thank you to the rest of my mentors—Hugo Van Vuuren, Nick and Tuan from Tivli, Andrew Rosenthal, Bilal and Nitesh at General Catalyst, and so many others—who have been sounding boards for all my crazy ideas and questions. Thanks to my friends and roommates—Sebastian, Matt, Will, Mike—for dealing with my late nights and craziness. Thanks to one of my best friends, Andrea Brettler, who has offered her advice and support since freshman year. Special thanks go to Peter Boyce, who has been my biggest supporter and harshest critic for the past 3 years, and Perry Hewitt, who offers the most sage advice and the wittiest jokes of anyone I know.

    My work at Rough Draft Ventures over the past year has shown me how dedicated student entrepreneurs can be. After funding many of the best student ideas in Boston, it’s clear that Boston and New York are now tech hubs of their own. I grew up in New York and grew academically, professionally, and intellectually in Boston. Those cities are my roots, and I hope to be the bridge between this East Coast hub that’s rapidly growing and the storied Silicon Valley ecosystem that has so much to offer the students growing companies here in Boston. I will continue to work with Rough Draft and help students, and the fact that our partners are doing such diverse things is a testament to the types of students we’re looking to fund—people are willing to drop everything they’re doing and pursue an idea relentlessly.

    I couldn’t be more excited for what the next two years hold.


    Then the Popular Electronics article came out. Gates’ friend Paul Allen ran through Harvard Square with the article to wave it in front of Gates’ face and say, “Look, it’s going to happen! I told you this was going to happen! And we’re going to miss it!” Gates had to admit that his friend was right; it sure looked as though the “something” they had been looking for had found them. He immediately phoned MITS, claiming that he and his partner had a BASIC language usable on the Altair. When Ed Roberts, who had heard a lot of such promises, asked Gates when he could come to Albuquerque to demonstrate it, Gates looked at his childhood friend, took a deep breath, and said, “Oh, in two or three weeks.” Gates put down the receiver, turned to Allen and said: “I guess we should go buy a manual.” They went straight to an electronics shop and purchased Adam Osborne’s manual on the 8080.

    from Fire in the Valley: The Making of the Personal Computer

    By Zach Hamed on May 9, 2013.

  • This post was originally published on Medium in 2013.

    As I finish this semester, I thought it might be valuable to shed some light into the unique entrepreneurship scene at Harvard. It can be clichéd, but it’s hard to deny Bill Gates’s and Mark Zuckerberg’s Harvard roots. There’s increased interest in entrepreneurship on all college campuses, but at Harvard it has accelerated especially rapidly given The Social Network and the Facebook IPO. The startup scene has grown beyond recognition in the three years I’ve been on campus—I’m a junior now—so I’ll try to objectively describe the various initiatives around campus and then offer my own thoughts.

    Harvard Innovation Lab

    The largest addition to Harvard’s entrepreneurship efforts this year was the new Innovation Lab (i-lab for short). The 30,000-square-foot ground floor features day-use space, reserved space for incubated teams, a classroom, conference rooms, a kitchen stocked with snacks, and a game room filled with video games.

    Physically, the building is on the Harvard Business School campus. While it isn’t next to the center of campus (Harvard Yard), the vast majority of entrepreneurship events are now hosted there, so many students have been spending more time there. The i-lab has hosted a startup career fair, a Startup Weekend hackathon, and office hours with venture capitalists and entrepreneurs-in-residence.

    University-Sponsored Initiatives

    Considering that the i-lab hosts or runs many of these initiatives, it makes sense to describe these next. The administration recently came out strongly in support of entrepreneurship, sponsoring a President’s Challenge that awarded 10 teams $5,000 each to advance their ventures in the areas of clear air, clean water, global health, personal health, and education. A panel of professors then awarded a grand-prize winner and up to three finalists a total of $100,000 to develop their ventures during the summer. While money isn’t the only solution to encouraging entrepreneurship, the resources and backing of the University certainly go a long way to helping student-led ventures.

    The Experiment Fund

    Probably the second most important announcement of the past term was the launch of the Experiment Fund, a seed fund run by NEA, Accel Partners, and Polaris Ventures to help fund student ventures. While the fund was initially launched at Harvard, it is expanding to include other colleges in Cambridge. The fund has already financed a few ventures, including health incubator Rock Health and TV-over-the-Internet startup Tivli.

    Hack Harvard

    The newest technical addition to startup extracurriculars is Hack Harvard, an organization that brings together mostly engineering students who are working on personal projects. An emphasis is placed on cool hacks or integration of third-party APIs. In the last year, they welcomed a number of technical speakers, among them Aza Raskin of Massive Health and former creative lead of Firefox. They also welcomed the Winklevoss twins and Divya Narendra of The Social Network fame.

    Hack Harvard runs an incubator program over winter break for campus startups. Students learn more about web development and design through a number of workshops led by professors and upperclassmen. They spend the rest of their time advancing their projects in anticipation of a demo day for other students, investors, and the Boston community.

    Rough Draft Ventures

    Just a few months ago, General Catalyst helped launch a new seed-stage fund in Boston for students working on a startup of their own. Rough Draft Ventures gives students up to $25,000 in the form of an uncapped convertible note to fund their venture. Its first investment was $20,000 in Balbus Speech, a company focused on special education and speech therapy.

    Zuck returns to campus

    The biggest tech celebrity to come to campus in 2012 was Mark Zuckerberg, who returned for the first time since dropping out in 2004. His homecoming was billed as a recruiting talk, and he spoke to an audience of computer science students. Overall, his visit further invigorated campus interest in computer science.

    Computer Science Department

    The most notable addition to the Harvard CS program was Computer Science 164: Mobile Software Engineering. The class is not only an introduction to iOS programming and jQuery Mobile, but also a great primer in industry-standard software development practices, including pair programming, code reviews, source control, unit testing, MVC frameworks, and database scaling. The class is taught by star CS professor David Malan, who also teaches the introductory CS class, CS 50. CS 50, a 10-week overview of computer science in C, HTML, CSS, Javascript, PHP, MySQL, is now the second most enrolled class at the College following Introduction to Economics, demonstrating the surging popularity of CS at Harvard.

    Social Entrepreneurship

    The entrepreneurship scene isn’t limited to tech startups. Students are interested in social entrepreneurship across a number of areas, including education, health, clean tech, and more. Through extracurriculars like the Social Innovation Collaborative and University initiatives like the President’s Challenge, there is an emphasis on socially-oriented ventures.

    Business Plan Competition Winners

    There are two main business plan competitions on campus. College students enter the i3 competition, while HBS students enter the HBS Business Plan competition. Past winners of the HBS competition include Rent The Runway, Birchbox, CloudFlare, RelayRides, and thredUP. In 2012, the winner of the business venture track was Vaxess Technologies, a company working to commercialize a technology to condense vaccines into a thin film strip that can be shipped and stored without refrigeration. Here’s a full list of the winners and runners-up.

    On the college level, a total of $50,000 was awarded to six major award winners for everything from a foot shape analysis technology to an iPad point-of-sale survey platform. Here’s the full list of winners.

    Harvard College Venture Partners

    There is also a strong interest in venture capital on campus, the main activity for which is Harvard College Venture Partners, or HCVP. HCVP brings venture capitalists and successful entrepreneurs to campus to speak with Harvard startup founders. One of its main objectives is to facilitate cross-campus collaboration, particularly with Harvard Business School students and professors.

    HBS

    Harvard Business School has become notably more open to sharing its resources with the rest of the University. The i-lab is one way of connecting HBS professors with undergrads and other schools. A new class taught to undergrads this year was U.S. and the World 36: Innovation and Entrepreneurship. The class—a survey on innovation across disciplines—was taught with HBS’s signature case study method. It was primarily taught by professors Joe Lassiter and Mihir Desai and co-taught by visiting professors from other Harvard schools, including the Kennedy School of Government and Engineering School. The course culminated with students working on over 40 real-world projects at various startups and organizations.

    Harvard Business School students have also increasingly turned to the College to learn about CS. Enrollment in CS50 by HBS students was sharply up this past fall. Many students were happy with their decision to take it, and the increased interaction with undergrads was largely welcome (though I don’t believe many undergrads have bandwidth to work on outside projects, which I describe more below).

    This shift towards openness was both student- and faculty-driven. The new FIELD curriculum requires that all ~900 first-year students conceive, establish, and grow a business using $5,000 in seed money from HBS. This broad shift in the first-year curriculum followed the success of Startup Tribe, HBS’s homegrown entrepreneurship club founded just two years ago. As I understand it, entrepreneurship among the HBS student body was previously an afterthought, something only a small percentage of students did. Startup Tribe helped change the entrepreneurship scene on campus, so much so that its founders recently received the Dean’s Award for their efforts.

    HLS and the Harvard Law Entrepreneurship Project

    Further demonstrating how Harvard’s graduate schools are now collaborating, the Harvard Law Entrepreneurship Project (HLEP) helps student startups avoid common legal pitfalls and critically assess the viability of their businesses. Each semester, after a pitching and vetting process, the Student Practice Organization pairs law student teams and an attorney advisor from Cooley, Gunderson Dettmer, or WilmerHale with ten to twelve student entrepreneur teams. All projects are also reviewed by the current General Counsel of Charles River Ventures. HLEP has worked with entrepreneurs from virtually every school at Harvard so far. Recently, HLEP’s leadership organized Hack IP, a weekend-long event dedicated to brainstorming and developing a policy about copyright that HarvardX should adopt.

    i-lab Silicon Valley Trek

    Another effort to raise interest in entrepreneurship as a career choice was the Innovation Lab’s trek to Silicon Valley. About 40 students, evenly split between HBS students and undergrads, Graduate School of Education, Kennedy School, and engineering graduate students, visited Silicon Valley VCs, startups, and incubators.

    We heard from Michael Dearing at Harrison Metal; serial entrepreneur Mike Cassidy; Randy Komisar from Kleiner Perkins; Matthew Prince at Cloudflare; James Reinhart at thredUP; Diego Rodriguez at IDEO; and many more.

    Incidentally, Cloudflare was founded on that same trip in 2009, when founders Matt Prince and Michelle Zatlyn developed the idea in the hotel bar in between trips to startups. Having that in mind as we visited Harvard alumni across the Valley was even more inspiring. From my understanding, the general consensus from students on the trip was that they were newly inspired and driven to get a career at a startup after graduating.

    Here’s a short video chronicling our trip.

    Recruiting

    There is no shortage of startup opportunities for students, but it can be hard to sort out the good opportunities from the bad. The main recruiting mailing lists get 5-10 emails a day with startup opportunities. Here are a few excerpts of a few of the more interesting requests.

    We are looking for a technical co-founder who can build and design all aspects of the website, including creating an attractive product and managing the back-end database. The programmer should know (or be willing and able to learn quickly) PHP, HTML, CSS, JavaScript, and MySQL at a minimum. Familiarity with jQuery would be beneficial. The programmer should be able to essentially replicate Pinterest, or be confident that they can learn how to do so in a short period of time. Please provide any examples of previous work, if any. Our engineer will be an equity partner in what we believe will be a very profitable business and great learning opportunity. We are also open to discussing salaried compensation instead of equity. The co-founder will join a team with experiences ranging from entrepreneurship, design, consulting, and law, and will learn about the contacts and skills necessary to start a new venture.

    and

    I have a project which I need your assistance on. What am I offering? A partnership. I have a concept which I believe is worth pursuing. It most likely will involve php, sql, and rss. The first step would be letting me know if you are interested or not (I know some of you are very busy). The second step would be a non-disclosure agreement. I would then explain the concept, and you could tell me if you are interested in helping develop it. You would then tell me what percentage ownership in the company you would be seeking. I would then see which offer is a match between ownership and skills and select. You pick your own team. We will make it work. I look foward to hearing from you.

    On the other hand, we also get a number of recruiting requests from exciting, well-funded San Francisco, New York, and Boston startups looking for students to fill internship and full-time positions.

    If you’re interested in recruiting Harvard students, there are two main outlets to do so. First, contact the Office of Career Services. They’re the official middleman between employers and students, and they’re incredibly committed to increasing the number of students who go into the startup world after graduation. They can help get your job posting submitted into the Harvard job posting database, and will be able to tell you what career fairs are coming up. Second, submit your posting to [email protected]. Most CS students are subscribed to that list, run by the Harvard Computer Society, so it’s a good way to find qualified CS students.

    Thoughts

    In my opinion, Harvard’s startup scene is a microcosm of the broader startup environment: There’s a lot of noise, but there are many gems in the rough that will be hugely successful.

  • This post was originally published on Medium in 2013.

    I’m looking to invest in a company that:

    • Is a retail market leader
    • Sells everything from clothes and books to appliances and electronics
    • Has a loyal customer base
    • Allows customers to buy “membership” in return for special perks
    • Encourages customers to buy in bulk
    • Has expanded into verticals unrelated to the retail focus it had when founded
    • Sells generic products under its own brand name

    Any recommendations? Amazon comes to mind, but today I want to argue there’s a second, better candidate:

    Ready for your crazy idea of the day?

    Taxes and Physical Locations

    Amazon is slowly being forced to charge users sales tax in states across the country. California, Texas, and Pennsylvania residents are all being charged tax. Just this week, Massachusetts Governor Deval Patrick announced Amazon would begin charging a 6.25% sales tax next fall. Amazon’s reaction to these states’ actions is to open warehouses and distribution centers, seeking to reduce their already fast shipping time to hours, not days.

    Now if you wanted to open a bunch of warehouses all across a state, located near consumers, in advance of a large-scale implementation of same-day shipping, you’d be hard pressed to find better locations than these:

    That’s a map of Costco locations across the U.S. Costco has 600+ large warehouses already built, near major metropolitan areas. There’s no better way to reduce shipping time to customers than these centrally-located stores.

    Warehouses

    There’s a difference between buying a supermarket, or a Best Buy, or any other store, and buying Costco.

    All of Costco’s stores are warehouses.

    Let’s illustrate this for a second. Here’s Costco:

    And here’s an Amazon warehouse:

    See the similarity? I can imagine Kiva Solutions’ fulfillment robots working behind the scenes at Costco warehouses, fulfilling a user’s order while a customer picks up products in-person.

    Buying in bulk

    Amazon has “Subscribe and Save”. Costco’s whole premise is that you buy in bulk. The New York Times published an analysis of Costco’s prices against Amazon’s subscribe feature, and Costco came up as a cheaper option in most items, unless you take into account time to/from/at Costco. If Costco could ship to your door under the Amazon Prime umbrella, most people would just shop there.

    Membership

    Amazon has Prime. Costco has, well, Costco membership. Both of them use membership programs to encourage customers to buy more and buy often. Costco membership runs for $55 or $110 a year, while Amazon Prime is $79 a year (less if you’re a student).

    Why not Walmart?

    Assuming Amazon even wanted to buy a large physical retailer, it wouldn’t have many choices, since there aren’t many retail stores that cover the breadth of Amazon’s product selection. Walmart comes to mind, but their market cap ($230B) makes the purchase prohibitively expensive for Amazon (market cap of $130B).

    Conclusion

    I wrote this as a thought experiment after seeing the similarities of both Costco and Amazon on Black Friday and during the holiday shopping season. An outright merger probably won’t happen, but the two companies are definitely similar in how they operate.

  • This post was originally published on Medium in 2013.

    I love New York City. It’s home, but it’s also a million cities in one. You can go from one neighborhood to another in a span of blocks, and sometimes that transition can be jarring.

    If you want a taste of those neighborhoods, just drive down Madison Avenue. Let’s start at 57th and Madison. Looking downtown, we get a glimpse of IBM’s offices.

    Looking uptown, we see Mont Blanc and Coach stores across the street from each other. The next 40 blocks are similar: store after store selling luxury goods.

    At 96th and Madison, the transition gradually begins. These large apartment buildings are the last ones you’ll see with penthouses for a while.

    At 98th and Madison, you reach a 3 block stretch of Mount Sinai hospital complexes.

    When I was a kid, there were only 2 buildings. Slowly but surely, the hospital has bought whole blocks of the surrounding area and built a complex of emergency rooms, teaching hospitals, and doctors’ offices.

    At 102nd and Madison, construction on a beautiful new building that houses classrooms for Mt. Sinai’s medical school just finished.

    That new medical school sits across the street from the George Washington Carver houses, one of the first project complexes you’ll enter on the way into East Harlem.

    And at 103rd and Madison, you see a 1950s-era public school across the street from another low-income housing complex. It’s the school I attended for nearly 8 years in elementary school, but more on that later.

    There’s no real 100th and Madison, since 100th Street never actually intersects Madison. But it acts as a sort of “Platform 9 3/4,” dividing two very different socioeconomic classes. It’s a divide that shouldn’t exist.

    Let’s paint a more convincing picture. Here is a map of the city’s ethnic makeup based on the 2010 census, courtesy of the New York Times. Each dot represents 25 people. Green dots represent White New Yorkers, blue dots represent Black New Yorkers. Yellow dots represent Hispanics, red dots represent Asians, purple dots represent Native Americans, and grey dots represent “other”. See that line on the right side of the image where green ends and yellow begins? That’s 98th street.

    How about a map of homicides from 2003-2011, also courtesy of the New York Times:

    Want a clearer picture? Here’s a map of median income distribution from the 2010 census, courtesy of WNYC.

    At 96th St., median income is $184,583 +/- $75,883.

    At 98th St., median income is $82,750 +/- $40,958.

    At mythical 100th St. and the immediate area uptown, median income is $28,196 +/- $6,021.

    It’s a $150,000 decrease of income potential in 4 blocks.

    The real issue is educational opportunity. Here is a graph of student performance, courtesy of the New York Times, at P.S. 77 Lower Lab, located at 96th Street and 3rd Avenue. P.S. 77 has 340 students total (K-8). 7% are “poor,” qualifying for the federal free lunch program. 92% of 3rd graders passed their state tests, 55% were advanced proficient, and only 5% were below standard.

    P.S. 171–the school I attended from pre-kindergarten to 6th grade–is located at 103rd and Madison. It has 615 students total (K-8), 100% of whom qualify for federal free lunch. Of third graders, 64% passed their state tests, 24% were advanced proficient, and 2% were below standard.

    Now for P.S. 146, located at 106th Street and 1st Avenue. It has 450 students, 88% of whom qualify for federal free lunch. Yet only 20% of third graders passed their state tests, 2% were advanced proficient, and 35% were below standard.

    This is how cycles of poverty start. 3 schools, 3 very different educational outcomes.

    A block can make a world of difference.