Midnight Oil

There’s been a lot of buzz surrounding Google Wave recently, and I’m proud to admit that I still have really no idea what it is. I’ve decided to ignore it and let the rest of the community digest it and tell me whether it’s the real deal or just a flash in the pan. Why? Because I’m trying to be an entrepreneur, and Wave is not going to make me any money.

I’ll admit, it’s tough not to get caught up in the excitement. Here’s a snippet from an email I received recently regarding a meetup to discuss Wave (original emphasis left intact).

I’m going to make this short and sweet. We have a meeting this Thursday July 16th. The next paragraph explains why, if you are a true web enterpreneur, you shouldn’t miss the event.

If you didn’t cash out during the DotCom boom and haven’t found success with the Web 2.0 surge including the Facebook and iPhone app bonanzas yet are still looking for opportunity then you need to seriously think about Google Wave. To learn how Google Wave could be the “3rd wave” of Internet Innovation behind “DotCom” and “Web 2.0″ come to our AWE meeting this Thursday July 16 as we’ll present Google Wave and have an open discussion on the opportunities that it presents.

Wow. When I read that, my first thought was: “I had better be there. I don’t want to miss the boat yet again.” I never made a Facebook app (except for work), and I likewise didn’t make a million in the App Store. I’m still working on making some Web 2.0 money, but it sure hasn’t resembled anything like a hockey stick. So, getting a foot in the door early on “the next big thing” holds somewhat of an allure for me, as I’m sure it does for any hacker.

However, I’m trying hard to keep myself head-down on DoLeaf and Obsidian Portal and ignore all non-core technologies. I don’t need a new toy, I need new customers. Plain and simple. Jon Crawford of Storenvy says it best: Stop learning new stuff! (13:40 minutes in) I think that’s the difference between a hacker and an entrepreneur. At some point, the entrepreneur has to do the 90% of the app that’s not cool and not fun. Hackers can put down their current project and pick up a new toy whenever they feel like it. It’s a good life, but I doubt it leads to financial success.

So, if you’re a hacker, please play with Wave, make something cool with it, then push it in my face so I can’t ignore it. Meanwhile, if you’re an entrepreneur who already has a project, I suggest you do what I’m doing: Get back to work.

I noticed the other day that some of the organizers in The Scene (ie. Atlanta startup culture) are hosting a meetup to talk about the next steps needed by the startup community. In big bold letters are instructions detailing that possible attendees should evaluate themselves according to these criteria:

Who SHOULD Attend

If one of the following phrases describes you then you SHOULD attend this event:

• Entrepreneurs who “Swing for the Fences”
• Angel Investors, Venture Capitalists and Institutional Investors
• Service Providers that service the Startup Community
• Other Supporters of the Startup Community Ecosystem

Who Should NOT Attend

If one of more of these labels describes you more than one of the previous labels then you SHOULD NOT attend this event:

• Lifestyle Entrepreneurs (emphasis mine)
• Small Businesses using the Web for marketing
• People who prefer the security of employment
• Developers, Designers, Freelancers
• Internet and Network Marketers
• Interactive Agencies

No Lifestyle Entrepreneurs?

As a recovering wannabe “Swing For the Fencer”, I’m dismayed at the specific exclusion of lifestyle entrepreneurs. When did running a successful-but-not-Google-size business become a failure? Wouldn’t The Scene be much better off with dozens or hundreds of successful small businesses as opposed to a handful of mega hits and hundreds of failures? Let’s keep this list growing at a healthy clip, while keeping this one as small as possible. I know people love to throw around fail-fast as a mantra, but I prefer to win-slow. Successful small business that pays the bills? Put me down for one, please.

In my own experience, I was only able to truly get a shot at success when I stopped swinging for the fences. When I stopped dreaming about VC money, IPOs, and a Google buyout, I set about to actually building a revenue model for my projects. In addition, I stopped pursuing ventures that had no underlying business model besides the get-big-get-bought prayer. All of a sudden, I started making money. It’s not a lot, but it’s growing. I bunted my way to first base, and now I’m trying to figure out how to steal second.

Any bootstrapping entrepreneur needs the ability to barter. There are a lot of things you can do, but many many more that you can’t. So, you partner up with other like-minded people and barter your skills and time.

For Obsidian Portal and DoLeaf, we’ve been getting lots of free graphic design work from our friend Drew at Fifth Street Creative. He’s really great and does awesome work. The only downside is that I feel it’s too much of a one-sided relationship. We get so much, and I’m not sure what we provide in return. I’m afraid we’re draining the well dry and eventually he’ll say no, or even worse, won’t be a friend anymore.

They’re fast, I’m slow

Given an hour or two, a graphic designer can make some great stuff. A handful of new icons, a couple ad banners, even a brand new logo. The end result is easy to transfer, and it’s immediately useful. I don’t want to underestimate the amount of effort that goes into graphic design, but it just seems to me that most designers can create some great stuff really fast.

What about a programmer? What can I do in an hour or two that’s useful to a designer? I really can’t do any meaningful programming. A “whole site” is completely out of the question, and a new feature is often pretty tough to implement as well. I might be able to help fix a bug, but even just getting the development environment set up can take anywhere from ten minutes to a couple hours. It’s just not practical to do any real programming in such a small time frame.

The Goal

My goal is to figure out a symbiotic relationship where everyone benefits, everyone stays happy, and it’s sustainable. The ultimate setup would be where both parties always feel like they’re getting a little more than they’ve earned. I want it to be where both parties are saying, “What I do is so simple and easy. It can’t be worth the awesome help the other person is giving me.” From that perspective, here’s a few things I think I could offer:

Javascript

I think a lot of designers deal with Javascript, and I can imagine it’s a frustrating time for someone with very little programming experience. I’m definitely no expert, but I can usually get the job done.

CSS Help

Again, no expert here, and I’d imagine that many designers are already better than I am. However, if I’m working with someone whose experience ends with Photoshop, I could probably help quite a bit with turning a PSD into styled XHTML.

General Troubleshooting

You can’t become a decent web developer without learning a little about sysadmin tasks. Managing databases, creating users, and creating cron jobs are all skills that every decent programmer can handle. I know a lot of people are terrified of a shell prompt, so I can imagine this kind of help would be very useful.

From the comments

As usual, our readers have a lot of great ideas. I’ll try to compile my favorites here.

User Interface/Experience Advisor

You can help your designer friends by being another set of eyeballs and allowing them to bounce ideas off you. In addition, with your knowledge of server-side programming, you can advise on what is and isn’t possible/practical in terms of interaction or AJAX.

Submitted by Stephen and Ali.

Backups

Keith G had this idea, and it’s quite novel. I doubt people will ask you to help them with a backup strategy, but you could definitely suggest it. Just ask your friend, “What’s your data backup strategy?” A blank stare means it’s time for you to explain the importance of database and asset backups. A little work with mysqldump and S3, and you just saved them a world of hurt.

CMS Setup and Education

I always assumed that graphic designers all had their favored CMS’s. However, according to Jordan Lev, this is not the case. Spend a couple hours showing your designer how to install WordPress or Drupal, and you open up all kinds of doors for them.

Others?

Is there anything I’m missing? I’d especially appreciate commentary from graphic designers who are in need of technical help. What do you need? What could a programmer do to help you?

On January 23, Gabe over at Penny Arcade gave a fairly glowing review of Obsidian Portal. It was short and simple, but basically said “They get it” when it comes to managing a D&D campaign. Minutes later, the PA masses started streaming in, and thus began the craziest couple of hours in Obsidian Portal’s history, and what I will forever call PA Day.

Beware the Cave of Tits!

The Epic Tail

Our traffic spiked by at least 1000% pretty much immediately. Page load times skyrocketed from a second or so into nearly a minute range. To compound the issue, I was at work plugging away on a hard deadline of “right now!” I couldn’t just ditch and go work on Obsidian Portal, so I watched helplessly as we were wanged.

Luckily, Ryan was a little more flexible than me, and he got to work. Logging into our slicehost panel, he immediately started spinning up a slice with 2GB of memory. All the while he was giving me updates via IM. It was like something out of a BSG episode, with the heroes spinning up the FTL drive while the Cylons are swarming them. (Note: We don’t consider the Penny Arcade users to be Cylons, although they might like that.)

Ryan: It’s at 30%
…
Ryan: 60%
…
Ryan: 90% almost done
…
Ryan: 100% – New slice is ready. It’s syncing and doing the switch
Ryan: come on…come on…
Ryan: We’re up!

All the while, I was terrified that something would go wrong in the switchover causing both the original and the new slice to be inoperable. Further, what if there was a problem with the DNS, causing requests to go to the old slice instead of the new one? I thought I was going to throw up, I was so nervous.

But within only minutes our new slice was up and running and doing a much better at handling the influx of traffic. Still, just to be sure, Ryan went in and started tweaking Apache / Passenger settings to make sure that everything was in tip-top shape. As we all know, Apache is pretty damned complex and it’s pretty hard to get the settings just right for your particular instance, especially on the fly. Things were running much better, so I was finally able to start relaxing.

The Fallout

Obsidian Portal had a massive spike in both visitors and signups. Our overall traffic was up 1,000% from the previous day, but even better, thanks to Gabe’s endorsement, the Penny Arcaders were signing up at a rate twice as high as regular visitors. Compare that to your average digging, reddit, or slashdotting, where visitors browse through and possibly leave a hate-filled comment, then move on.

By the time the dust settled on Monday afternoon when Penny Arcade posted a new story on their homepage, we had received thousands of new signups and hundreds of new campaigns. All in all, it was a fantastic weekend.

Visits were way up, but even better…

Pageviews stayed high even as visits declined. That means we hooked some of them!

Lessons Learned

Success or Failure?

Campaign updates were streaming in.

When the first wave hit us and our server started collapsing, it seemed as though we had failed. Here were thousands of people trying to get to our site, and they just plain couldn’t. Ryan especially seemed very frustrated.

However, when I thought about it later, I realized that it was a success, even if the site would have crashed and burned. Why? Simply because thousands of people were trying to get to our site. People were eagerly attempting to connect to our server and in the meantime were spreading the word about our site through the blogosphere, twitter, and others, letting all their friends know how the guys at Penny Arcade thought Obsidian Portal was so awesome. They also found resources in other locations such as previous reviews, Obsidian Portal’s Twitter account, Obsidian Portal’s Facebook Page, and even Michael Harrison’s Viemo Video World Building with Obsidian Portal.

The lesson? Maybe you scale, maybe you don’t, but at least you proved your idea. It’s a lot easier to take a popular site and make it faster than it is to take a screaming fast site and make it popular. The technology issues are by far simpler than the social ones.

Break out the credit card immediately

The very first thing Ryan did was to spin up a bigger slice, and that had by far the biggest impact on the number of requests we could serve. We could have tweaked MySQL settings, adjusted Apache processes, or experimented with exotic caching. Maybe it would have helped, maybe not. Optimization is a tricky business. When you’re at the point where your server is on its knees, you don’t have time to figure everything out, so spend money instead of time. Call your host and say “Gimme the biggest one you got!” You can always downgrade later.

Make basic optimizations ahead of time

Go ahead and spend a couple hours doing basic optimizations. For example, on Obsidian Portal, we had already applied some aggressive caching to the home page prior to PA Day. It took Ryan a couple hours to figure out. That’s a couple hours we didn’t have on PA Day, so we’re glad we spent them up front. Lesson? Don’t go nuts and try to optimize everything, but go ahead and do the basics. Do it now! Don’t wait!

Always have two sysadmins

I’m glad I have a day job (and a paycheck!), but that means I’m not always available to handle issues with the site. On PA Day, I was in crunch time at work and therefore pretty much helpless for Obsidian Portal. Luckily, there are two of us who can essentially do everything. That way, there’s a much better chance that if something happens, one of us can get to it and fix it before it causes too much trouble. It’s important to have failover backups for people as well as hardware, and someone to double check your ideas before implementing them in a hurry.

Yay Slicehost

Getting bigger iron was our fastest, safest, and best course of action. Slicehost made it easy. We were able to spin up a new identical slice with double the RAM and CPU in only a few minutes. Essentially, Ryan flipped a switch, waited 15 minutes, and we were on a beefed up server. No service call, no email, just raw speed. Perhaps other hosts offer this solution, I don’t know. What I do know is that Slicehost has always preformed exceptionally, and we thank them for that.

Yay Passenger

When Ryan wanted to move from Mongrel to Passenger, I was a little skeptical. I’m always hesitant to “fix” that which isn’t broke. Seems a little like running in place to me.

However, Passenger made scaling a snap, at least as far as server management went. No editing the mongrel cluster. No managing and restarting via God or Monit. Just leave Apache running and it will do its thing when the requests start rolling in. It’s just one less thing to worry about.

Going forward

Things have calmed down a bit now, and we’re back to the sure and steady growth that we’ve been seeing all along. Our new Penny Arcade fans have been successfully hooked and are steadily churning out new storylines, characters, and campaigns.

On our end, we’ll keep working on the site, adding features, fixing bugs, and improving server performance to be better prepared for more days like PA Day. The continual good feedback we get keeps us energized and hopeful that it will continue to grow. We may not be rich (yet), but we’re creating something that people love, and that feels great.

And one last thing. It’s a site written in Ruby on Rails and we made it scale!

I had lunch with a friend the other day, and he pitched me an idea he had for an iPhone/Android/whatever app. When he was done, he asked, “What do you think?” Without thinking, I answered with, “Hmm, sounds neat. Cool idea.” He told me that’s what everyone said. It was then that I realized he had asked the wrong question. Instead of asking, “What do you think?”, phrase it like this:

Friendly Optimism

If you’re asking friends (or even just generally polite people) about your idea, they won’t want to hurt your feelings. They can tell you’ve got a lot of enthusiasm and excitement tied up in your idea, and it would be a real jerk move to throw cold water on that. So, they answer, “Cool idea!” or perhaps “That’s neat. You know what else you could do?” Very few will give you real, jarring, critical feedback. Instead, they’ll try to be good friends and cheer you on. Unfortunately, you need a reality check, not a cheering section.

Ask to be bruised

If you make it clear that your goal is to get real, unbiased feedback, you pave the way for someone to be honest without seeming rude. In addition, if you explicitly ask them for negative feedback, they will be pressed to come up with specific criticisms, instead of vague encouragements.

Once the truth starts flowing, take some notes and ask for more. Resist the urge to get defensive and just let your reviewer express their opinions. Once they realize that you’re truly appreciative for the beating they’re giving, they’ll really start to build up steam. Thirty minutes of this can generate some truly exceptional insights. You may think you know what sucks about your idea, but others may be able to poke holes in it you never imagined.

React and Adapt

No idea is perfect, and your job as an entrepreneur is to overcome and adapt to the imperfections in your idea. If you can’t recognize and counter your own weaknesses, then your success will be severely limited. It’s nice to get a pat on the back every now and then, but it’s absolutely necessary to get raw, unfiltered criticism. Very few will give this freely, so it’s up to you to drag it out of them.

I saw an article in the New York Times the other day about working 10 hours a week and making $10 million a year. The article profiles Markus Frind, who started an online dating website, Plenty of Fish. The main thrust of the article is that Markus barely works at all and just sits back raking in cash. Are there any other web entrepreneurs out there who are sick and tired of hearing this story over and over? This is all I ever hear, and I secretly dream about it while working on my projects, but it doesn’t match up well with the real world of late nights and no money.

Hmm, let’s look through the NY Times article and see what the keys are to creating a cash-cow website:

• Just sit down and create a site as an experiment in teaching yourself a new programming language.
• Ignore the interface and usability. If stuff looks bad, just say, “Users don’t care about that.”
• Forget about customer service and moderation. Crowdsource it to the forums.
• Don’t charge users for anything. Rely 100% on advertisements.
• Lie in your hammock and collect checks.

Ok, I’ll admit, this is the life I want to live. This is the dream of all us web guys. However, I’m starting to suspect that the vast majority of “successful” web entrepreneurs invest a lot more effort and reap much smaller rewards. How many of us out there are pulling in $50, $100, or dare I say it, $500 a month from our projects? If I could get Obsidian Portal to generate $100 a month, I would be ecstatic. After paying off the hosting fees and whatnot, my take-home would probably be less then $1/hr. Still, it’s a goal to shoot for.

We can’t all be Digg, YouTube, or Facebook, but that’s OK. Success has different levels, and if we can just generate enough income to justify the amount of time we spend working on the sites we love, then that’s success. I just wish the media would profile a few more of us who live on the wrong side of profitability, work until 3:00 in the morning, and jump for joy with every subscription or CafePress T-shirt we sell.

Are you like me, barely scraping by (or not, as it were)? Drop a comment when you take a break from furiously writing code or begging someone not to cancel their account…

Update(Feb 2010) – We’re now making a decent amount of money from Obsidian Portal. Not enough to live on, but that goal is starting to become visible on the horizon. We’ve been at it for 3 years now, and maybe, maybe we’ll be ramen profitable in another 2-3. Still, from what I’ve seen of other web entrepreneurs, that’s a smashing success. So, to all you others out there in the same boat: It’s possible, but it’s slow and it’s damn hard.