I think I’ve got some good momentum now.

I’m really excited about it.

I’m just gonna keep working on it.

I think I’m getting my head wrapped around Illustrator. The concepts, at least, if not exactly the skill.

I’ve been starting to practice copying icons (this one’s taken from 750words.com, it’s the badge you get for writing your 750 words pretty quickly many days in a row):

The left side is my vector-made version, and the right side is of course the blown up original.

Here’s how mine looks in Illustrator’s pixel preview:

Not quite as good, but not too bad, right?

I got a small Wacom tablet on loan from a friend, too. Though, I think it needs some calibration because it’s all loosey-goosey with its lines right now. In any case, I’m super stoked and motivated to make a few of my own illustrations and icons for this new site I’m planning.

For anyone who is interested, I’m reading the Adobe “Adobe Illustrator CS4: Classroom in a Book” and watching all the tutorial videos on this page.

In the meantime, I’m officially out of the starting gates on the development of my website.

Here’s what I’ve been working on the last couple days:

• Made a few more changes to the data model, added a bit more of a wild card element to the “game”.
• Am reading “A Theory of Fun”.  Loving the amateurish drawings that go along with the writing.  Sometimes unpolished is full of charm.  This book was recommended to me by 3 out of the 4 people who responded to my original question about game-design books.  So far, it’s living up to the hype.
• Found a few ways to super-simplify the idea.
• I am prototyping the interaction and design for what will be the first major action on the site after signing up.  I think this is the heart of the site, and I think it’s good to start at the heart.
• Realized my mantra: seek out complicated, ugly, tedious, and useful parts of the world and make them simple, pretty, and fun.
• Have been drawing lots of pictures and going on lots of walks.

Tomorrow is the end of week 1, and I was hoping to have a bit more done by then, but I’ve been exhausted the last couple days (I think 5 weeks of wacky sleep patterns is finally catching up to me).  I got a lot of good sleep last night and am still exhausted today.  I’m hoping that my body either adapts or more sleep eventually fixes the problem.  Can’t really think creatively and embark on huge tasks of design without a fully rested mind.

After I decided to sit down and figure out how to draw in Illustrator, I think it’s going to be easier than I thought.  I stayed up a little late and watched a bunch of tutorial videos on adobe.com, and think I can wrap my head around handles and anchors.  In fact, I think it’ll probably be easier to draw in Illustrator than to draw on paper and scan it in.  At least for the level of complexity that I’m interested in being able to do (not much).

I’m excited about that.  New skill!

When I woke up this morning (well one of the times, since there are now about 3-4 separate wakings up to have new ideas from) I started thinking more about the multidisciplinary nature of entrepreneurship, especially when you’re a 1-person company and want to do as much of it yourself.  Of course, I realize that this is sort of a “bad idea” amongst some entrepreneurial thinking.  Almost all VCs and other entrepreneurs recommend having a 2-person team, at least.  Personally, I think that that applies mostly when your “idea person” is not technical, or isn’t technical enough.  My strength has always been the ability to be creative and technical at the same time.  My weaknesses have always been design, completing that last 10% of polish, promoting completed products, and scaling successful ideas.  I’ve made a pretty conscious decision to try harder at the last 10% of polish by having smaller projects, promoting projects (this blog is one attempt at that) in the last year or so.  And scaling, has mostly been taken care of by the improvements in cloud computing hosting services.  That just leaves design.  And I’m on it!  I also have found a couple great designers that I like working with… I just feel bad asking them to work for little pay, as it’s always at the beginning of a project that I most need their help and have the least resources to compensate with.

Here’s a quick list I put together of skills, and the types of people that are generally expected to have those skills.  Some of them are “nice to haves” but all of them (I think) can play a crucial role in the success or failure of the project if they are absent.

What’s missing from this list? Everyone has these skills to a certain extent, but many of them must not only be trained over time, but also simply embraced as skills worth having. So often I hear ideas from people who are almost proud of having no technical ability. Is drafting technical people a fun pasttime? Why not just spend a week or two with a book and a good technical friend willing to answer questions and knock that skill out? It really doesn’t take much more than that. I’ve come to believe that skills are mostly personality decisions. We often decide to write off certain skills as a way of defining ourselves.

Learn a new skill. It will save your project a lot of time and money in the long run. Life is long.

My brain is in that stage where all of the ideas are coming together in a very fortunate way. Ideas that I didn’t realize were related, become related. Complicated things become simpler, difficult things become easier. It’s that stage of creativity that often gets attributed to a muse, because it’s almost like the ideas are just falling in your lap. I love it.

I did have one setback. There is a company out there named Esha, which aggregates nutritional data from a bunch of sources and licenses it back out. Some popular iPhone apps use them. I wrote to them the other day asking for a price quote. Get this. $35,000 one-time fee with a $15,000 yearly fee to get the information updated. That’s crazy, right? They’ve been around 25 years, though, so it must mean that people are paying for this. I guess it’s just shocking to me because I’m one person, and most people who want this data are probably big businesses. Still. It just feels like this is a company that the internet is going to destroy. That information should be free, because it’s nothing that people wouldn’t be willing to aggregate and share in this new world.

On the other hand, the USDA publishes their nutrient database every year for free, and it’s what most of the iPhone apps use.  It has 7,000 foods in it instead of 40,000, and in my comparisons I’ve been a little disappointed by some of its omissions (no pesto, for example, and no peanut butter and jelly sandwiches), focusing more on ingredients than staple foods, but sites like dailyburn.com have APIs that include an exponential number of foods, all user-submitted, to even Esha.  Esha, watch your rearview mirror!  Okay, enough poking at Esha… I just couldn’t believe it when they wrote to me with that quote.

I’ve also decided to take my drawing skills to the next level, and learn how to import drawings into Illustrator and work on them from there.  I’ve been sort of afraid of learning these skills, even though my drawing skills aren’t bad, and I’ve used Photoshop for many many years.  What’s to be afraid of, really?

Being able to work on my own icons and images would free me from being tied to a designer.  I’m not saying that I won’t enlist the expert help of some designers, because they’re years ahead of me on skill level, but I have just never felt comfortable relying on them entirely.  What if I need a single icon and they’re on vacation, or slammed with another project?  I want to be able to knock one out, and not break out in hives.  You know what I’m saying?

If anyone has any tutorials or books to recommend me, that would be very helpful.  I have figured out that autotrace might be useful in converting drawings into vector graphics.  Let me know if that’s the wrong path to go down.  I’m thinking that I’ll draw things on paper in black in, scan them in, autotrace them, clean them up, and color them in Illustrator (I have CS4, if that matters at all).

There’s so much freedom and power in being able to not only think up an idea, but build it, and design it, especially in the early stages.  It’s not about having the best skills in the world, but being willing to pick up new skills.  So, to all of you “idea people” out there who are afraid of learning how to actually build your ideas, I say pick up a book, ask a few questions, and build it.  It will be so much easier to pitch your idea or move from prototype to final product if you aren’t relying on someone else to implement or design your ideas.  There’s nothing to be afraid of.

Maybe I’ll post some of my creations here as I go along as proof that you don’t have to be great in order to make serious progress.

The combination of starting a new project and dealing with a 5-week old’s sleeping patterns has rendered me a little sleep deprived.  Can’t sleep before 2am because I’m buzzing with ideas, and can’t sleep past 5:30am because Niko needs to be talked to and played with.  So I’m in a bit of a zombie state today, and while I should be taking the weekend off, I’m still thinking about things and thought I might as well post about it here.

What is my 90 day challenge’s measure of success?  I’ve been working with goals and challenges long enough to know that it’s pointless to make goals that you can’t verify success or failure from.  So, I came up with what I think “success” would be for this project, by September 16th.

• Launched
• Making $3,000 a month
• The work is meaningful and the result is fulfilling

I say $3,000 a month because I thought my original hope of $5,000 a month was probably not going to be possible.  Can an idea go from zero to $60,000/year run rate in 90 days?  My Locavore iPhone app did, last year.  It took 2 years for 43 Things to become profitable, but when it did it was profitable on a much larger scale than $3,000/day.  All of the other sites we made, however, had more difficulty getting to that milestone.  So, it depends on the ideas.  Some ideas make money quickly but don’t have much growth potential.  Others take longer and grow bigger.  Others burn a  lot of money and either fizzle out or get bought up.  I don’t have the luxury of a long runway.  The 2 years of 43 Things seemed short at the time, but 90 days is pretty much ridiculous.  I’ll need a lot of luck, I guess I know that, and might as well admit it publicly.

Ways to make $3,000/month that I’m considering:

1. Sell 1,428 iPhone apps at $3 each, or ~47/day
2. Get 600 people to subscribe to a service at $5/month
3. Some combination of the two

Because of my personal strengths and what I think works best with my set of ideas, I’m probably going to go with #2, and then transition to #3.  I don’t think I’ll be able to do all of that in 90 days, but who knows.  Locavore took about 3 months to make, but I was only working on it in evenings and weekends at the time.  It did take about a month or two to get any momentum in sales though, and without big press-worthy news on a daily basis, and Apple’s help marketing, it hasn’t been possible to maintain that rate of sales over the year (which is another reason why I’ve decided not to put all my eggs in the #1 basket… it relies a little too heavily on the good will of powers outside my control).

Anyway, those are my zombie-like thoughts of the day.

I have to admit, I do like the drawing board. All of that potential, none of those nagging worries about reality.

After waking up at 6am with Niko, I decided to start writing some notes to myself (on 750words.com) about this 90 day challenge with myself.  What kind of business do I plan on building?  How will it sustain not only itself, but also me and my family?

I’m going to stick to my strengths.  This means, currently, Rails websites and iPhone apps.  Since I’m stronger on the Rails front than the iPhone front, I’m going to run with an idea I’ve been playing around with in the back of my head for a while.  Something somewhere in between Locavore and 750 Words and 43 Things and McLeod Residence and also inspired by other current faves in the world like Foursquare.

So, what have I done today?  Here are a couple things:

1. Decided to build a website that exists somewhere between free and subscription service.
2. Made a list of big problems that I’m going to have to solve.
3. Drew out some very basic sketches for what I think might be the most important part of the UI to begin with.
4. Started a new Rails app, set it up with Compass, jQuery, my default layouts, blah blah blah.
5. Set up subversion.
6. Looked into Heroku for hosting… didn’t quite figure it out but will have to return to it later.  If anyone has a great cloud-based Rails host to recommend that doesn’t require a ton of sysadmin knowledge (I hate doing that stuff), let me know.  I see that Rackspace has something new along those lines.  Has anyone tried it?
7. Built up the User model with signup, login, logout, forgotten passwords, email verification, and edit (using this old tutorial that I always end up going back to reference).  Decided not to go with just OpenID like 750 Words since that has actually turned out to be a bit of a pain, and confuses people.  This is another step of building websites that I hate.  It’s boring and yet complicated and you have to get it absolutely right or else you’re going to pay for it later.

Now, I’m going to take a walk, get a coffee, and think about the ideas that are spinning together in slow mucky motion.  I LOVE this part of the project.

Ah, day one.  Such a crisp feeling.  If only every day was going to be as simple and clean as day one.

And in a bit, it’s the weekend, and I’m going to enjoy it, and come back for day two on Monday.

A little over a year ago, I left the Robot Co-op and started Enjoymentland here.  Since then, a lot has happened.  My wife got pregnant and we had a son, to name perhaps the most life-changing one.  I continued to develop Locavore.  A worked on a little side project that ended up turning into 750 Words.  And behind the scenes, there has been another big project that I’ve been working on, which involved creating a tool for restaurants and bars to run more efficiently.  It was a paid gig, and I partnered with a great friend and a great business to put this together.  We built something amazing, really useful, and actual simple and fun to use.  Before I left for paternity leave, I had it at a point where it was 98% done and was being rolled out to our alpha testers.

Yesterday, we decided not to launch it.

It’s not that we don’t think we built something amazing.  I think it’s probably the slickest thing I’ve ever built, actually.  I put in a ton of work, and addressed some amazing problems with simple solutions that things like the web can now solve easily for businesses that are a bit behind the times, technology-wise.

Mostly, for me, it came down to a few frustrating technical problems (one of our data-suppliers decided to bail on us at the last minute), and the fact that selling new technology to non-tech companies is sort of difficult.  It reminds of the feeling I had when (as a hopeful young novelist) I had to start pitching manuscripts to agents and publishers.  The joy of writing and the joy of selling pull from two completely different springs.  One spring is bountiful in my soul, the other, not so much.

And then there’s the issue of opportunity cost.  Doing anything costs exactly as much as the price of not doing something else.  Sometimes it’s not enough to have a good idea, or a good business, or even big success… we should all be striving to find the success that best suits us, that ties our passions up with our work, that sustains our sense of purpose, that justifies this one chance on this planet that we have to do anything we want.

One of the benefits of small companies and few business partners is that we can make swift changes.  We can “fail” early.  We haven’t made any giant bets that we can’t take back.  There is not an irrecoverable amount of sunk cost.

So, without much further ado, we’re freezing the project, stepping back for a bit, and re-assessing.  Sure, it sounds suspiciously like The Dip, or The Resistance, speaking here, but I’m almost certain that we’re all doing the right thing (after a night’s sleep).  In fact, I think it’s mostly fear and uncertainty that would keep us on the project, rather than take us away from it.  Leaving the project is what I’m afraid of.  Especially since it means that I’ll be losing 66% of my monthly salary (which was already down 50% from The Robot Co-op), and we’ll be living on life support until something fills the gap.  Also, strangely, I was on their payroll as a means to secure a home loan originally (one that never went through since we didn’t sell our house before Niko was born, and now we’re off the market until next year) so that might become an issue again when we decide to move if I still don’t have an “official job”.  But whatever, right?

Talking with Kellianne last night about it, I think I’m going to give myself 90 days to either come up with, build, and become profitable on a new idea and business, or strongly consider re-joining the gainfully employed people of the world.  Which, back in the day, I thought I’d never be able to do because I was too spoiled by the luxuries of self-employment, but it turns out that luxuries also mask dangers and anxieties that taunt us in the night.

90 days.  That puts me at September 16th.  New profitable business or bust.  Now that I’m 100% above ground again, I’ll be posting here more.  Wish me luck!