We just rebranded and redesigned the entire Grouper site in about 3 weeks. We came in under budget, perfectly on time, and the results exceeded our expectations. It couldn't have gone any better.
We owe much of this to a single piece of brilliant advice we received a few months ago, which applies equally well to hiring a designer part-time or full-time.
I was chatting with Aaron Epstein and Darius Monsef (aka Bubs), the founders of Creative Market and Color Lovers — both awesome, designer-focused sites. I figured if anyone would have pro tips about working with designers it'd be them. They didn't disappoint and delivered this gem:
Make sure you like the designer's style so much that you would trust them to create a design for you without any input.
If you try to force a designer into a style that's not their own it's often slow and painful; if they're working in their own favorite style it's usually smooth sailing.
I spent hours and hours sifting through hundreds of Dribbble profiles looking for styles that I loved as-is. I settled on an awesome 22 year-old designer from LA named Kyle Miller.
We knew we wanted to do something retro to echo our product itself, which is all about getting back to what matters — your relationships with friends, old and new, in the real world. Kyle's take on mid-century modern is simply brilliant and is perfect for Grouper with little or no changes.
Working together was a breeze. Since I liked and trusted his taste so much, the revisions were few in number and usually concrete rather than creative in a nature. The small number of revisions let us work much faster than we could have otherwise. Not only did we come in perfectly on time and under budget, but we were even able to expand the scope of the project to include additional designs and even new t-shirts.
I rep a Grouper t-shirt every, single day. (Fortunately, I have a few).
There are two reasons why I do this:
I don't have to think about what to wear.
Free advertising.
The first reason I stole from Steve Jobs. His iconic outfit is often misunderstood. He wore that famous black mock turtleneck, Levi's, and New Balances not to make a fashion statement, but almost for the complete opposite reason: so he didn't have to think about what to wear. Apple is a tremendously focused company and it stemmed from a leader who tuned out all distractions, even ones as trivial as getting dressed.
The second reason was inspired by Larry and Sergey. An early Google investor told me that they wore their Google t-shirts every day in the early years. “Free advertising,” they explained.
I respect Dalton Caldwell as one of the smartest people in the Valley. He built two of the biggest near-misses of the past 10 years, Imeem and Picplz, and he writes excellent, thoughtful essays on his blog. I'm a huge fan.
For those who missed it: he is creating what is essentially a crowd-funded, ad-free alternative to Twitter, what he calls a “real-time notifications API.” He introduced this new service with a blog post and video railing against the hollow promise of ad-supported models, and promising to align incentives with users and developers.
While I have immense respect for his audacity, I think what he's proposing is as meaningless as what he's fighting against. It is an example of the insular, group think that can be a problem in Silicon Valley. Most people, outside of a tiny tech elite, don't care about the pain points nor the solutions he discusses.
To Dalton Caldwell
Dalton Caldwell: the world needs you to work on something bigger and more meaningful, just as you urge our generation to work on more than “getting people to click ads.”
You should move to New York and re-rethink app.net. The tech scene here is steeped in reality in a way that the Valley simply isn't. Most of the people you'll meet here aren't engineers or VC's or bloggers. They talk about real problems. Like loneliness or stress or sickness or unemployment or high prices or lack of education. Please, I urge you to use your undeniable talents and world class team to tackle one of these far more pressing maladies.
The world doesn't need a slightly better Twitter, just as the world doesn't need a slightly better ad model.
And, to this end, it would be helpful to escape the echo chamber of Silicon Valley and relocate to New York. Today New York has plenty of startup infrastructure in terms of funding and engineers, but it also has millions of creators and experts and consumers in fields beyond tech.
Dropbox and Github, which you mention as shining examples of ad-alternatives, are great companies that solve real, widespread problems and have real, sustainable business models. But I'm afraid “too many ads on Twitter” or “a slightly too restrictive developer API” are not actual, widely-held problems, and that Kickstarter-type donations aren't a sustainable business model for a massively scaled social network.
I don't mean to come off as a hater. Again, I truly respect your audacity and your willingness to take on such a bold project. I just think it's the wrong one.
But time will tell. Potential backers will be able vote with their dollars. It appears as though the project will not move forward if it does not reach its funding goal of $500,000 or approximately 10,000 users. If the campaign hits these milestones, it may suggest that there is more of a desire for this than I think there is (although I would still argue that winning over 10,000 technorati's doesn't mean it will cross the chasm to 500,000,000 normals as Twitter has).
I sincerely wish you the best of luck with this project, but If you fail to reach your funding goal, then I humbly ask you to consider my audacious proposal.
Many tech companies are trying to “disrupt” existing industries, but few actually do. There is, however, one unmistakable sign of real disruption: when the incumbents try to change the rules.
Uber, the outstanding on-demand car service, has ascended to this rare status. The taxicab industry/mafia has long felt threatened by Uber (even forcing them to drop their original name of UberCab). Earlier today the local government in Washington DC voted on legislation specifically designed to thwart Uber's new product, UberX – a hybrid fleet that offers lower prices than Uber's standard black cars. The cab lobby attempted to push through a “minimum fare” that was blatantly designed to protect them from competition with UberX, and would without question hurt consumers.
Airbnb is waging a similar battle with the hotel industry. The Hyatts and Hiltons of the world have good reason to feel threatened, too: Airbnb has more than 100,000 active listings, which is more rooms than most global hotel chains.
It reminds me of the legacy of basketball great Wilt Chamberlain, whose unprecedented dominance as one of the league's first athletic “big men” (he was 7'1") directly resulted in numerous rule changes to try to blunt his advantage. He still managed to score 100 points in a game (still a record) and win 2 championships.
While these legal battles may be expensive and frustrating for the startups that face them, ultimately they are an overwhelmingly positive sign: that you're so damn good, the existing players can't compete without changing the rules. Like Wilt, Uber and Airbnb will win, because their products are just so much better than the competition. Pesky rules changes can't stand in their way.
Congrats to Uber on prevailing today – fortunately the anti-Uber amendment was removed. And to all the other nascent startups out there: may you be so successful that your incumbents try to change the rules for you too.
I moved to Silicon Valley when I was 19 to embark on my first startup. I knew nothing and virtually nobody except for my co-founder.
It was 2006 and it wasn't as easy to learn the ropes back then. This was before much of today's startup infrastructure existed. There was no Hacker News or Github or Twitter or AngelList or Stack Overflow. This was before EC2 and the iPhone, when Myspace still had ten times more users than Facebook. Y Combinator was just getting started.
We raised some money and assembled an amazing team, but struggled as a company. Good people came and went, and as the ship was sinking many people jumped off before we went totally under in the summer of 2008. At our peak we had 25 full-time employees and ultimately had to let go everyone who remained.
One thing that stays with me is the way in which people carried themselves on the way down. Most were gracious and respectful, but a few were not. Some quit, some were fired, some left sooner versus later, others held on to the very end.
I tried to treat everyone with the utmost respect, because this is how I was raised. I was by no means perfect, but on the whole I'm proud of the way that I handled myself. And I'm glad that I did.
For all I knew I wasn't ever going to see any of these people again, but I couldn't have been more wrong. I have since run into almost all of my former colleagues in the wildly small social circles of the tech world.
Our lead engineer, Nathan left on great terms to work on his next project, which became Airbnb. My former co-founder Daniel became the first employee of a YC startup that was later acquired by Google. One of our VP's, Halle stayed on until the bitter end before going on to found a non-profit, graduate from HBS, and start the successful health care incubator Rock Health. Three engineers started Y Combinator companies and three more started other venture-backed projects.
I even ended up pitching one of our former interns who now works at a top-tier VC.
Sometimes in the chaotic trenches of a startup people make bad decisions. Your company seems like the only thing in the world and you're willing to do anything to ensure its survival. You're stressed and overworked. It can be a recipe for disaster.
Unfortunately a few of these episodes have played out on Hacker News and Twitter over the past few days (which, frankly, is what compelled me to jot down these thoughts). It's tough to watch.
You chastise a departing employee, or refuse to pay a contractor, or fire off an angry email, or get into a nasty feud with your co-founder, or worse. At the time it might feel pragmatic or cathartic, but it's a horribly bad idea, because, in the language of Game Theory, the startup world is a repeated game. It's never worth maximizing this round at the expense of all future rounds.
You're going to have to face these people again. And statistically this isn't going to be your last startup. Keep that in mind.
There's a relatively thick line between being resourceful and being a dick. Don't cross it.
You should always treat people with respect, first and foremost because this is how fellow human beings deserve to be treated. But you should also remember that it's a long life in the small valley.