Our daily routines had become stale. We finished the accelerator as four guys living in a one bedroom apartment and moved in to a spacious townhouse. Instead of working out of the office, we were now in the living room plotting our internet takeover. Everything was going great, but it was just a bit more boring than when you’re sharing space with 26 other companies. We needed to do something to spice up our daily lives. With some inspiration from Project Enrichment, our team’s solution was to run a weekly challenge. Sunday we would set our goal and the challenge would last until the following Sunday where we would each write about it and bask in our glory. Challenge accepted.

Week 1: Wake up at 8:30am every day

Startup life of working 9am until 3am wasn’t proving to be sustainable after the summer. During the week of Demo Day, I was on a regiment of 3 cappuccinos a day. Our overarching goal was to be more productive and personally be more effective. What challenges could we craft for ourselves to form habits that make our daily lives better and improve ourselves at the core. We saw waking up at the same time and giving ourselves more of a rigid schedule to be the first step in that process, although in itself not the most difficult of challenges. We set our alarms and stocked up on coffee to prep for the challenge ahead.

Results

Great success, coming from waking up between noon and 4pm every day, the shift was quite a shock. The first few days felt like getting “flashbanged” out of bed. Our handy french press and some freshly roasted beans from Red Rock made the morning enjoyable. By the end of the week, it wasn’t a struggle anymore. Tips for success: - Go to bed at the same time, with the same routine. - Don’t read e-mail or schedule anything within a few hours of bed. Mostly before bed I would play with our turntables or on the occasion some Half-Life 2. Avoiding work right before bed helped that sense of monkey mind, where your brain goes into overdrive when you lie down. - Read articles from Instapaper in the morning. Usually I check tweets and electronic mail in the morning, but after switching to Instapaper I stopped getting that feeling of, “I could sleep another hour… or write 60 emails back.” - If you work from home, take a shower and eat before you do anything else. Morning where we got right into work, we tended to skip both until we totally crashed out midafternoon. Update: The week after was not quite as sustainable, with one day waking up around 4pm. Most day, it feels more natural to be an “early-riser” and I find myself waking up without an alarm more and more. My new favorite morning habit has been reading an article or two from Instapaper while in bed, truly fantastic.

Next Challenge

Read through GTD, set up a calendar, and to-do system.

Being known as “the website guy” really sucks. You have everyone and their mother pitching you on why you should build the love children of existing popular internet companies. My favorite was “so I want to build like a yellow pages, but instead of set prices you can bid on them”… ebay? That was a typical request when Alex and I ran Kiwi Grove, our web design agency. Really our entire business broke down into three categories, e-commerce sites, business sites, and personal sites. Our workflow for taking clients was super simple. E-commerce? Build a shopify site and pick a theme. Business? Setup wordpress and setup a themeforest theme. Personal pages? Nope, sorry we just don’t do that.

One day my little brother showed me a flavors.me page and asked if it was worth the $20 to get one. I laughed that he even wanted such a thing and said I could build it an hour if he really wanted. So an hour later the template was born, complete with google apps for email, links to his social networks, a picture of himself, and quick bio. It was so pathetically simple, yet he was totally satisfied owning a small piece of the internet. The no personal page rule had been broken. A few weeks went by and Alex came to me with an observation, programmers have the worst websites. He showed me a few links from his friends on github and man they were bad. Lorem ipsum text was everywhere, links were broken, information hadn’t been updated in years, and to top it off they were just plain ugly. We hatched a solution; improve upon the template we used for my brother and release it to open source!

With some tweaking and hacking during accounting class it was pushed up and released on Hacker News as Maori, our moment of glory was here. Before the project dropped off the homepage, we got about 40 forks of our project. Our template starting sprouting up in a few places and life was good. Alex and I actually used the template to make our own pages and made some more improvements and then released the changes back to github. The problem was no one was picking up on our new changes, it didn’t matter how awesome the improvements were, no one was willing to duplicate their work to get a few new features.

Frustrated, we let the project sit. Things were all quiet until we saw a hoard of tweets pointing to the then private beta About.me. So wait you mean we have to wait weeks until we can use this thing? I don’t think so. Alex and I converted Maori into a Rails app and launched within a weekend. We needed a URL even cooler than About.me and came up with WhyHello.Im. With a few tweets and emails to friends, we wrapped up our side project and called it a smashing success. We had built something that we used ourselves and could push updates out to the few people who wanted our template without any work on their part. Things went back to normal for a few days until Alex noticed some database errors. Checking it out we realized that our few tweets travelled a LONG WAY, and turned into ~2,000 Why Hello users over a three day period. Our non-marketing somehow worked and even got Dave McClure to sign up and Why Hello featured on Lifehacker Japan.

We spent hours trying to figure out how this happened. Turned out that by pure luck a few tech influencers signed up and loving that we let them use Markdown in their bio, shared the app. Seriously, Markdown… who would have thought. Our users, besides friends and family, all other developers that were too lazy to make their own personal page. Realizing this, we knew that we built the whole thing wrong. Instead of ease of use, we should have focused on what makes developers look and feel awesome about themselves. A few hours was spent sketching and we registered an alternate name, helloworld.im. Then the idea just sat there, we brought it up and were reluctant to resume work on Why Hello because we knew we were going to build this new product soon. New user growth stopped on Why Hello as About.me came out of private beta and then it went off to join AOL as quickly as it started. The space got super hot and other clones sprouted up, but somehow our’s wasn’t forgotten. Let’s be honest, it was a remarkably similar to About.me at this point, so much so that we got an email from Tony Conrad, the founder of About.me telling us to “find our own vision”. Interestingly though, our retention was really high. The few users we did get loved the product, so much so they linked to it from their Twitter pages, Facebook, etc. and our traffic remained steady.

The opportunity to participate in 3 Day Startup at Rackspace HQ came up and we decided to take it to build Hello World out. Our grandiose plan was to clone Why Hello, add premium features, and start charging users. We would be the only 3DS startup in history to have recurring revenue at the end of 72 hours. Bad news though, I had an asthma attack that put me in the hospital the whole first day and we couldn’t activate our payment gateway on the weekend. Our plans got cut back, but we released an entirely new product in just two days and presented it. The panel that we presented to didn’t really get what we were trying to do, but a few of the guys at Rackspace loved it and encouraged us to work more on it.

A call to an old friend, actually to complain about their terrible UI skills, totally changed our trajectory. When I shared Hello World, they totally got it and introduced us to the team at 500 Startups. Alex and I had thought it couldn’t hurt to pitch to them and set up a phone call. The hours before the call were terrifying. We had met Dave McClure the year before at SXSW and seen him steamroll a few entrepreneurs egos. We expected a metric torture session and prepared the best we could for it.

When the call finally came, the vibe was completely different, we talked about our product, how we met each other, what we wanted to build, and how we would work through certain issues. It wasn’t scary at all. The most terrifying part was just knowing that the accelerator program we would be joining started in a week and that we would need to 180 our entire lives to make it happen.

We went back to business as usual and then two days later, the news came. Hello World would be joining the 500 Startups accelerator batch #001 and we needed to be in Mountain View by the end of the week. Quitting our jobs, transferring our clients, dropping out with three classes left, and packing our lives into a Jetta was a non-decision. Working on Hello World and being surrounded by the best in the business was where we had always dreamed of going. There was no choice, we just did.

Every product has a story and this is how our’s begins. Hello World.