This chapter is a free excerpt from Make Something People Love: Lessons From a Startup Guy.

Think of Steve (or better, pick one of your friends or loved ones) there behind the computer. Think of a normal person sitting there, engaging with this machine, trying to have a good experience and you’ll very quickly see why so many startups are doing it so well. The way I look at it is: your “UX” (user experience) shows me how much you respect me or, in some cases, how much you disrespect me.

1) Your UX shows me how much you respect me.

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Think of Steve (or better, pick one of your friends or loved ones) there behind the computer. Think of a normal person sitting there, engaging with this machine, trying to have a good experience and you’ll very quickly see why so many startups are doing it so well. The way I look at it is: your “UX” (user experience) shows me how much you respect me or, in some cases, how much you disrespect me.

1) Your UX shows me how much you respect me.

Take SeatGeek for example. This site reinvented how we find the best ticket for any sporting event, for any music event, for anything anywhere, because it makes so much more sense when you can see the entire arena and where the best deals are based on location and price. This was a major UX change from the old way of looking at a bunch of lists and comparing multiple sites across different tabs. It was hard to figure out where your seats actually were, and even harder to figure out if you were paying a reasonable price. In short, it was a terrible experience. And then SeatGeek came along and gave us this one stop aggregator where everything was beautifully executed. That’s what design looks like when you think about your users.

Look at Instagram, which made it possible for anyone with a smartphone to take a photo that looked interesting, that looked good, that was something they felt good about sharing. As soon as you hit that front page, you know you’re going to have a beautiful user experience because it’s so obvious that they give a damn. They pulled off success in one of those cliche startup ideas “photo-sharing app” by focusing entirely on the iOS experience and making it as easy as possible to take and share a pretty picture.

Your design doesn’t have to be revolutionary (spoiler alert: I’ve rarely come across a startup that wasn’t derivative of some other idea—it’s OK!). For instance, temporary home rental website Airbnb’s success is really just an iteration of the couchsurfing model which has been around for ages. What they did, however, was take an already robust model and make it more beautiful. While they were still struggling to find a foothold, they started going out and taking good photos of the rooms themselves. They realized they had no choice but to make sure that their presentation, their aesthetic, was as good as it could be, because that was the deciding factor for many people.

Take a site like Dropbox. Dropbox launched at a time when everyone was doing the same kind of effortless cloud syncing, right? At some point a venture capitalist asked Dropbox’s founder, Drew Houston, “Why are you getting into such a crowded market when there are so many competitors?” and Drew simply said “Do you use any of them?” and the VC had to say “well, no I don’t.” Drew understood how important it is to create an awesome user experience. And if you can make something so easy on your users, you’ll have something they’ll want to talk about, and you’ll have something they’ll want to love. Users are remarkably adept at telling when they’re being respected.

2) Your UX shows how much you disrespect me.

For every beautifully designed website out there, there are a dozen or more terrible ones. If you’ve ever tried to look up lyrics online, you know what I’m talking about. More often than not, these sites bombard you with flashing ads and windows for ringtones before they even consider letting you see the lyrics you came there looking for.

Why do you hate me?

That’s because whoever made this website clearly hates you (or at least does not value you). Their main concern is getting as many advertisements in front of you as possible on the off-chance that you’ll click on one of their horrible pop-ups and make them 1/10 of a cent. And it’s inexcusable.

Another Y Combinator alumn, RapGenius (full-disclosure: I really love this website) decided to fix this type of disaster site. They had a very simple goal: help songwriters and their fans discuss and debate lyrics. They saw the wasteland of online lyrics searching and said, “No, no, no. Let’s actually make this a great experience.” They put together a website where you not only find the lyrics you’re looking for, but also have access to a Wikipedia-style creative space that allows fans to endlessly debate the meaning of lyrics (e.g., Rihanna’s “Birthday Cake” is not in fact about cake), bond over a love of Lil’ Wayne, and see how songs relate to one another. Where other sites are busy coming up with new ways to hate their users, these guys built an awesome website that uses great design to treat its users well. In a much shorter period of time, they reached traffic levels that far exceeded what reddit had when we were acquired.

The bonus? It turns out great design will also prompt fans to tattoo themselves with your brand. That’s when you know you’re making something people love!

(We couldn’t secure the rights to include photo of the rapgenius tattoo, but here’s a link to it on the rapgenius blog.)

This rule also applies to less-heinous abuses of users. Consider a site like Experts-Exchange which of late has been having its proverbial milkshake consumed by StackExchange.

The guys at Experts-Exchange thought they could keep all of their best content hidden from their users. They made it such a challenge to find the information you came looking for that when a better website like StackExchange appeared—which actually had all the great content you wanted and made it accessible—users switched over in droves.


So as you’re building your user experience, I implore you, please think of someone you care about. Because when he/she has a terrible user experience it feels like this:


And no one, no one should feel that way when using your product.

At hipmunk, our inspiration was this: This is the twentieth page of search results for a flight. Look at these search results:


Do you really think any human being would see this and think: “Oh, finally! I found the awful flight I’ve been searching for! I’ve been dreaming of a red eye with a six hour layover and here it is, twenty pages into the search results.”

No human would ever want this. So why would you ever show it to them? Some websites disrespect you by keeping valuable information from you. Others disrespect you by giving you so much information as to be utterly unhelpful. This was the case with airline searches.

To top it off, if you look at the very bottom, you’ll see it says:

Too many pages? Use the filters to instantly narrow down the list.

Why don’t they have these filters on in the first place? The only reasonable explanation is that they hate you and want you to have a terrible time using their website. So when you find yourself getting apoplectic while using a website, you know you’ve found a model that needs to be crumpled up and tossed so you can start from scratch.

Building hipmunk, Steve and Adam had a simple rule in mind: find the least agonizing flight possible. I joined a week or so before launch and remember when they told me about this special sorting algorithm they were internally calling “suckage.” We needed an alternate name before it went online, and someone (I don’t remember if it was Adam or Steve) offhandedly mentioned that they were thinking of calling it “agony.” I got excited. They had no idea, but they’d just stumbled upon the core branding for our website. It was so perfect, I exclaimed: we’ll take the agony out of travel search!

We approached travel search from the standpoint that most people would be willing to pay a little bit of extra money in order to avoid a really awful layover so our default search is ordered by “agony.” But we take into account all kinds of agony factors to make sure we show you the least agonizing flights first. Of course, you can still search by price if you want the absolute cheapest flight. We wanted to give our users something extra, another way to search for flights that could actually make them enjoy finding flights more—or at the very least hate it a little less.

We then we built our search results around a visual interface because we figured nobody wanted to look at twenty pages of masochistic flights they had no intention of taking. So we simply hid them. We also hid all duplicates so all the results could fit on one beautiful page, with a bunch of rows that show you when your flights take off and when they land.

We wanted the most honest way of doing business; we wanted to make it as simple and intuitive as possible for you to pick the least agonizing flight. So we only get paid when you book the flight, and we don’t show you any advertising. This is a big difference, because all the competition actually makes a majority of their revenue from ads. However, when you make a majority of your revenue from ads, you’re actually dis-incentivized to show better search results because more pages of search results means more opportunities to show ads, which means more opportunities to make money. We’d rather just earn money when you find the perfect flight and it’s been working out well so far. All the features we’ve included, from tabs within the page, to visual hotel searches sorted by “Ecstasy” (not what you’re thinking, probably) are based on maximizing your happiness per dollar. Take a look:


We’re the only travel site that does all these things because I think we’re the ones that care the most about making travel search better. That's not something we arrived at, it’s something that started at the very beginning, with the founders and continuing through every single employee, because we’re all obsessed with making sure you love travel search and we want that to show in everything we do.

That said, hipmunk is just a small part of the much bigger tsunami of UX, and it’s changing everything. Frankly, if Steve and I had launched reddit this year the way it looked in 2005, launch day would have been a little bit more awkward; fortunately, although reddit wasn’t polished, at least it put content first.

On the whole users’ expectations have changed so much in the last six years. But really, those changes just mean opportunity, because if six years has been this dramatic on startups, think of how dramatic it’s been for the rest of the business world. A lot of old playbooks are ready to go out the window because there are smart people dedicated to building products that put their users first. One of the greatest advantages we have as startup founders is that we’re not beholden to the old ways of doing things, and we can do things that larger companies could never dream of because they can’t abandon the old system.

The reason we at hipmunk felt so good about entering such a crowded market, even when some investors were a little hesitant, was the fact that we saw that no one had been innovating in this area, and we had such an opportunity to totally rewrite the way people do travel search.


UX: Keep a list of all the terrible, hair-pulling experiences you have using different websites. Write down what you wanted to do, and what thwarted you from doing it. Somewhere in that list is going to be a great new startup idea that someone is going to do, because there is no excuse for terrible user experience, none whatsoever.

When you’re thinking about reinventing user experience:
  1. Start with the core problem, the one that everyone else is failing to solve, and throw out whatever everyone is doing.
  2. Ask yourself the fundamental question: “What problem am I trying to solve?” If it’s making file sharing easy, start there. And if it’s finding the best, least agonizing flight, start there.
  3. Build a user experience that solves the simplest problem you can and you’ll probably be onto something.
  4. After you’ve mocked up a bunch of different approaches, try to find the simplest one that that still solves the problem, but doesn’t include anything that gets in the way.
  5. Talk to your market! Build a consumer app prototype. Then take this down to your local independent coffee seller and offer people a free cup of coffee to get their opinion on what you’ve built.
Ideally you’ll have something that is at least in static HTML, so you can get someone in front of it and can watch while they interact with what you’ve made. Remember to assure them that it's a no pressure situationand I’ll let you know, odds are they’ll never take you up on that free coffee. People are actually really nice. I’ve done this through reddit and beyond and rarely do they actually make you pay for the cup of coffee. But their insight is invaluable. Users don’t usually know what they want, but if you present something to them, chances are you’re going to get some good insights into whether or not they get it. And a lot of the most useful information that you get from them won’t actually be what they say, it’ll be the way that they use the site, the way they interact with your product for the very first time, even at a rudimentary prototype phase.
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