So I’m launching a little club and since I’m a relentless ego-maniac, I’m calling it the RyanWaggoner.com iOS Apps Club (takes 5 seconds to join up).

Why would you join such a thing?

Before I get into the benefits, I have five promises to make:

1. I will never share your email address with anyone, ever, for any reason.
2. I will never spam you.
3. You can unsubscribe at any time with a single click.
4. I will not email you more than twice per month (and likely only once).
5. I will only email you the kinds of value-packed emails I would like to receive myself.

So what do you get for signing up?

1. Sneak previews of apps before they’re released
2. Promotional codes for new apps (read: FREE STUFF)
3. Priority support if you ever have any problems or issues
4. The chance to ensure that my apps have that one MUST HAVE feature from day 1
5. Insider knowledge of what it’s like to be an indie app developer

I think this will be a really interesting project and I’m hoping you’ll join me. I’ll make sure it’s worth your time.

Click here to sign up in 5 seconds

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I’ve been doing web development full-time for the last four or five years, and in 2010 I started learning how to create iPhone and iPad apps. I switched to doing iOS development fulltime in early 2011 and I worked on a number of client apps throughout the year.

However, I haven’t released any apps of my own…until now.

My very first app just hit the App Store. It’s called SignPad, it’s iPad-only, and it’s pretty much the simplest app I could think of creating. I wanted my first app to be simple, and to give me a taste for the process of submitting an app to the app store, marketing it, etc.

The concept

You know how you see those people at the airport holding a sign with someone’s name on it? I thought it’d be cool to create an app that takes whatever text you type in and displays it on the screen as large as possible.

But I had a few criteria:

1. I wanted the text to automatically scale to be as large as possible, breaking text into multiple lines and scaling optimally to ensure that the text is as large as possible while keeping all of it visible. So typing in “Hi” should result in a very large font size, while “Hey there, good looking” would result in 2-3 lines of text, so as to maximize the area of the screen used.
2. I wanted the font, background color, and text color to all be easily customized.
3. I wanted it to be beautiful.

I feel like I hit all those items, and I just got my very first review today (4 out of 5 stars). Can’t tell you how exciting that is

What’s next?

My goal for 2012 is to release one app per month. I have a list of about 150 app ideas, and I have selected the apps for February, March, and April, and have a couple of those at the rough prototype stage. If you’d like to be a beta tester for future apps, shoot me an email and let me know.

In the meantime, check out SignPad and if you like what you see, please leave a review and tell a friend. Thanks!

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If you’re curious about DailyPath, you can check out the video of my talk below (it’s just a few minutes long). Overall, I’m pretty happy with the way it turned out, but I’d love any feedback on how I could have made the talk more engaging, or how I could do better as a presenter.

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I’m very excited about DailyPath and the opportunity we have before us, but there’s a powerful group of lobbyists and corporations out there that have backed two bills in Congress that represent an incredibly grave threat to the free and open nature of the Internet. You have probably already heard of these bills: SOPA and PIPA. If these bills pass, it will give large corporations the power to squash new startups like mine before they really get started, destroying job growth, economic activity, and amazing innovations for millions of Americans.

If you’ve already taken action and contacted your representatives to voice your opposition, thank you. If you haven’t, please take a moment to do so now. Google has a great guide on what you can do, as does Wikipedia. Wikipedia, Reddit, Wired, and hundreds of other very-high-traffic sites are blacked out today in opposition, and Google and other sites have posted requests for help in opposing these pieces of legislation.

Finally, it can often seem that bills like these are abstract and it’s hard to see who they’ll help or hurt, so here’s something to make it more concrete: my name is Ryan Waggoner, I’ve made my living via the Internet for the last seven years, and these bills will eventually wreak havoc on my livelihood and the future of my company. 

Please help me stop them. It’ll take you a few minutes, but it’s incredibly important. Help us stop SOPA and PIPA now.

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3. 200

Background

For the last four and a half months, I’ve been in a startup incubator (for my startup DailyPath) in Portland called PIE (the Portland Incubator Experiment). PIE is a project sponsored by Wieden and Kennedy, and our batch of eight startups also had Google, Target, and Coca-Cola as brand sponsors.

If you’re not familiar with startup incubators, they basically give fledging startups a little bit of seed capital, mentorship, and in our case, office space and access to networking opportunities with investors, press, industry professionals, etc. Our program ran from Sept 1st, 2011 through Dec 15th, and throughout that time we had investors, entrepreneurs, and advisors come in 2-3 times per week to speak to the group and/or do 1-on-1’s with each startup.

Our demo day is today, Jan 17th, and all eight startups will be presenting to a theater full of investors, press, and friends and family about how we’ve spent the last four months and where each of us are going from here.

Since we’re wrapping up with PIE, I thought I’d write up a few thoughts on the experience, what Ben and I have learned from it, and what to be aware of to maximize your own incubator experience, should you choose to do one.

1. Be careful about doing an incubator at all

There are tons of startup incubators out there, and new ones are popping up every day. And while there are a lot of potential advantages to joining an incubator, there are also downsides.

The primary advantages of a good incubator are access to investors, access to a group of experienced mentors, and being in the company of other serious startups. While you get some money, it’s usually not enough to make a huge difference. Most incubators give out $15k – 25k for teams of 1-4 founders, which isn’t much for the three or four months you’re in the incubator.

That said, I don’t think the average startup would be best served by an incubator approach. The amount of cash is too little, the mentors are generally accessible in our industry via an email or a tweet, and you can get the camaraderie of being around other startups via a coworking space. As for access to investors, AngelList has become the way to raise money as a startup, and with some hustle you won’t need the incubator to make connections for you.

For us, our program being sponsored by the largest independent ad agency in the world (W+K), as well as Google, Target, and Coke, was a huge factor in why it’s been good for us. But while there are a few “domain-specific” incubators out there, I don’t think most of the generic ones outside of Y Combinator, TechStars, and 500 Startups are probably worth it. You’d be better served finding a coworking space with other legitimate startups that you can be around without giving up equity. And then there are some that are just pure scams.

2. Be careful whose advice you take

Image by Gregory Taylor

One thing that became immediately clear to us was that we weren’t focusing on a lot of things that desperately needed our attention. Speaker after speaker came in and gave us a list of things that we had to be doing, like working on getting press, or building financial projections, or practicing our public speaking, or doing marketing communications (blog, twitter, etc).

The next thing we realized is that most of these people were well-meaning, but wrong. Yes, all those things are important, but the people giving these talks are specialists and domain experts. They’re not generalists like entrepreneurs have to be, and they have the luxury of focusing on one specific area. We’re constrained for time and capital, but mostly for time. So some of these things simply didn’t get done, and that’s ok. The important thing is to be aware of what you’re choosing to ignore for now, and to make sure you understand the tradeoffs.

One more thing to mention: startups are by nature ambitious, and they attract ambitious people. Ambitious people are generally quite opinionated and aggressive, so startup environments are full of people with strong opinions that they can’t wait to share with you. Be very careful to look at the results of the person giving you advice, and don’t mistake the force with which advice is given with the value of that advice. The squeaky wheel isn’t always the one that should get the oil.

3. You are not a big shot

When you’re accepted, it can be tempting to let that go to your head, and get an attitude that you’re too important to meet with this person or that person. You’re not. Or at least, you’re not because you got into an incubator. Just like raising venture capital, getting into an incubator doesn’t mean much. You haven’t built a business yet, you just took a tiny step.

4. Don’t judge a book by the cover

Related to the point above about how you’re not too important to meet with someone, one of the best things about an incubator is that it brings you into contact with a lot of interesting people who can help you get started in your business. But some of these people may appear from a distance as if they’re not relevant or helpful for what you’re doing. Be really careful with this attitude. I’ve had multiple experiences of wavering on canceling a meeting with someone because I just didn’t see what could come out of it, and then they ended up being extremely valuable connectors, partners, or sources of advice.

The key here is to limit your exposure to the risk of it being a waste of time. I’ll write more about this later, but try to tease out more via email, get them to meet somewhere close to you, just do a quick cup of coffee, and try to get *something* out of the meeting if it turns out they’re not valuable.

5. Leverage to the next level (more press, more funding, etc)

Incubators are stepping stones, so make sure you leverage them as much as you can. Right after we got accepted, we used the social proof of the incubator to raise some more money from friends and family. And while we’re not fundraising right now, most of the other startups in our batch have raised or are trying to raise additional funds coming out of the incubator. There’s a multiplicative effect here for investment and press that you should squeeze as much as you can.

6. Avoid blinders or narrow-minded thinking

As I mentioned above, we’re not raising money. We’re the only startup in our batch not raising money, and I’ll write more later about why. But this was a tough decision for us, and partly because we’re in an environment where it’s just assumed that you’ll raise money. There are real, hard-core advantages to raising money, but to claim that it’s the only way of building a company is just sloppy and myopic. So we made it a point to seek out the advice of other entrepreneurs who had bootstrapped their companies.

There are other examples, but suffice it to say that while you’re surrounded with dozens of people just like you for 14 hours a day for months on end, it’s worthwhile to talk to: a) non-technical people, b) non-funded technical entrepreneurs, c) non-technical entrepreneurs, and d) people who are very good at what they do, whatever the space they’re in.

Bonus #7: Get a good pair of noise-canceling headphones

If you’re in an incubator that has a shared space, like ours at PIE, make sure you get some good headphones because it’s really loud sometimes and when you’re in the zone, being in a noise and visually distracting space is the worst. Ben and I also come in pretty early (usually before 6am), which gives us hours of quiet time before anyone else gets to the office. So do whatever you have to do, but I recommend headphones.

Overall Takeaways

We had a great time at PIE and we’ll be sticking around in the space for a little while longer. If I could do it again, I definitely would.

If you’re headed into an incubator, above all, remember to have fun. Life is short and if you’re not having fun with what you’re doing, what’s the point? Enjoy the privilege of being able to focus on your new startup, being able to touch every piece of it yourself, and being surrounded by startups and mentors who want you to succeed.

If you’re thinking about trying to get into an incubator, that’s awesome. A lot of the success or failure of a startup is mental, so you can gain tremendous benefit by being surrounded by supportive mentors and peer startups, like the environment an incubator offers. Just remember that most successful companies didn’t join an incubator and didn’t raise outside capital. That’s not to say you shouldn’t, but you definitely don’t have to. Take a hard look at the options, talk to people on both sides (especially people who have been on both sides), and make the best decision for you.

Please don’t hesitate to contact me if you have any questions or curiosities about the incubator experience. I’d love to chat more about it.

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When thinking about user behavior, expect the worst of people. Expect them to be stupid, lazy, greedy, cynical, and impatient. Because for the most part, they will be. Not in general, but when compared against the idealistic “User” that many would-be entrepreneurs seem to picture in their mind. In general, people are busy and overwhelmed, and have very little time or energy to check out something new. And even when they do, they’re constantly being bombarded by new things from entrepreneurs. Why are they going to check out yours?

The problem is that most entrepreneurs are optimistic people by nature. You have to be to invest the time and money that it takes to start a company. But optimism can be really dangerous to a fledgling business. It can subtly convince you that the unlikely is likely. It can convince you that people will go out of their way to buy what you’re selling.

Fundamentally, virtually every new startup is asking people to change their behavior in some way, whether large or small. As a general rule, people do not like change, so you must make this change as compelling and painless as possible if you have any hope of success. And optimism will lead an entrepreneur to believe that the pain of the changes they’re asking users to make isn’t really that bad.

The optimistic entrepreneur believes that users will fill out their 15-field registration page to check out the amazing new product. The pessimistic entrepreneur knows that 99% of users will leave and won’t ever come back, so she works really hard to make it easy to try the product and get hooked.

The optimistic entrepreneur puts share buttons all over the page, thinking that users can’t wait to share their new discovery with their friends. The pessimistic entrepreneur knows that he has to appeal to the user’s self-interests, and offers a bonus or other benefit for users who share the site with a friend.

The optimistic entrepreneur thinks that what they’ve created is so compelling that people will return. The pessimistic entrepreneur knows that the average person remembers 7 URLs, plus or minus 2. The pessimistic entrepreneur knows they can’t expect people to remember to return to their site.

I’ll give you an example of that last one: woot.com is a daily deal site that offers a great deal on a particular item every day. They sold last year to Amazon for $110 million. Huge win, right? From 2009 to 2011, another daily deal site (Groupon) went from $0 to a $6 billion offer from Google. There are tons of differences between the two models, but I am absolutely convinced that Woot could have been bigger if they had taken a page from Groupon’s book and focused on building a mailing list to offer their deals to. I first saw Woot years ago, but I’ve been back maybe twice. I just don’t remember to go check it out every day. But I never forget to check my email, so I always see what Groupon has on offer. And yet the Woot.com homepage still has no place to sign up for an email notification of their deals.

You get the idea. The challenge is that you have to be an overall optimist, and you definitely don’t want to grow to hate people, but you kind of do need to expect the worst from them when actually designing your product.

Of course, creating a great product is only half the battle; you also have to market it well. But that’s a post for another day.

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But how to choose? Before spending hundreds of dollars to buy a domain name and then investing in a logo and other design assets, we wanted to be sure we had the right name.

One of the things we’ve learned over the years is the importance of customer development. As this new startup has a broad consumer audience, what we really wanted to know was which name the typical consumer liked the most. Posting to our Twitter and Facebook streams yielded little response, so we started looking for some way to get our list of potential names in front of a bunch of strangers, hopefully without spending a fortune.

Enter Mechanical Turk. In case you’re not familiar, Mechanical Turk is a marketplace on Amazon for short, tiny tasks that only a human can do. If you’re a startup, you might use it to have people tag photos on your platform, or identify inappropriate posts. Things like that. You can price each task however you want, down to a few cents.

Worth a try, so I setup a survey on Mechanical Turk and set the “reward” for each answer to ten cents. However, I didn’t want people to just click a random answer just to get the ten cents, so I also included some questions about their demographic (age, gender, income, education), and some open-ended questions about why they liked or disliked the name, as well as questions about what kinds of things they’d like to learn if they had the opportunity. I did the initial run for 50 different people to respond, and published the survey.

I honestly didn’t think I’d be able to get 50 responses. I mean, it’s a freaking dime. But I was wrong: after only a few hours, we had all 50 responses. And some people took the time to write multiple paragraphs about which names they liked and why. Completely bizarre. DailyPath was the clear winner, with more than twice as many favorable responses as the next contender.

Best of all, the total cost was $5. Not the last time I’ll be using Mechanical Turk. If you have a question that you’d like 50 people to answer and you have $5, give Mechanical Turk a try.

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When you work 40 hrs a week for a salary, the value of your time is roughly your annual salary divided by 2000 (40 hrs per week for 50 weeks). So if you make $60,000 per year, then the value of your time is $30 / hr. When you include benefits and such, that number might go up to $35 or $40.

However, people don’t really seem to think like this. If the value of your time is $40 / hr, then it makes sense to pay $20 to save an hour of time, for example. If you can hire a cleaning person for $20 / hr who can work as fast as you can, you should. Period.

I think one reason that people don’t see the world this way is that their time is worth $40 / hr, but only for the first 40 hrs per week. They effectively have a limited market for their hours. And you can’t really bank hours to be used later (or can you? topic for another post) so it doesn’t really matter how you use those hours, because a) no one will pay for them, and b) they’re going to be gone either way.

Contrast this with freelance, where people have a lot more control over how much of their time they convert to income. There have been weeks where I wanted to work on a project of my own or where I was traveling when I did no work, or only worked a couple hours on paying work. On the other hand, there have been times when I needed extra income and I was willing to put in 14 hours per day, seven days per week.

Not only are the first 40 hrs usually more valuable for a freelancer, but they go up from there. When I’m pretty booked, I’m still open to taking on additional work, but my rates go up by 50-100%. If I’m working at night or on the weekends, I’m charging extra for that.

It’s a really good feeling to know that if something comes up, you can adjust your schedule to optimize for free time or for extra income. Of course, there’s still lag time, which can be a problem. I haven’t quite figured out how to setup an arrangement where I can work from 0 to 16 hours on any given day at normal quoted rate, and get paid immediately at the end of the day for hours worked. That would be the ideal scenario in terms of being able to adjust my work to meet any financial needs. However, it’s not too bad right now; I generally can adjust the amount that I’m working with a couple weeks notice.

This level of flexibility has a downside, though. I remember when I first started doing freelance, I was very aware of the fact that every minute I stepped away from my computer was a minute that was costing me in time I could have been billing. An hour-long lunch with friends went from costing me $10 to costing me $60 (my hourly rate was $50 at the time). So for a long time, I wrestled with trying to bill as many hours as humanly possible, because I felt guilty otherwise.

Today, I tend to set income goals for the month and then base my hours on that. I look at my entire month as monetizable, and I have to decide how much of my time I want to “buy” back with income that I’ll forgo. And because I’m focusing more on disconnecting my time from my income (which I’ll talk about in a future post), all I’m expecting from my freelance at this point is to hit those minimum income goals.

Still, it’s nice to know that if I want to earn 2x as much in March and then take April off to travel, I can.

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The hard part with self-learning new programming languages is that there’s a hump between the first few steps, which are relatively easy, and the point where you feel like you’re starting to understand what you’re doing and you can make forward progress, even if it’s slow. This effect is much worse if you’re going from a type of programming you understand (like web application development) to a completely new paradigm (like native mobile application development).

In that zone in the middle, it’s hard to move in any direction, because you don’t really know enough to overcome even the slightest barrier. Even worse, you know that the answer is probably only a Google search away, but you can’t access that answer because you don’t know what question to ask. And you don’t know who to trust and wouldn’t recognize the answer if you saw it. And you have no idea how to test it. What you really need is a step-by-step plan of action, but if it differs in any way from your setup, you’re likely to get lost.

I think this zone probably exists for most topics, it just occurs with more severity in some, and its position in the learning cycle differs by topic. It’s a very frustrating point, and I suspect it’s the point where most people give up on whatever they’re trying to learn how to do. The difficulty of trying to struggle through that zone without any external guidance is just too hard.

But that’s only one reason that people don’t self-learn more topics; the other one is motivation. Self-learning is generally self-paced, which is often touted as a benefit. However, anyone who has tried to learn something (or just do something) on a self-pacing basis quickly finds out that there’s an inherent problem: few other things in life are self-paced. For most things, there’s someone else expecting what you’re working on, so you have an external motivator. But just doing something on your own doesn’t bring that benefit. Just like a workout buddy for the gym, this is why learning something with someone else is so effective. I can’t tell you the number of people I know who have tried to learn something new and ended up frustrated and decided to just take a class. And it makes total sense: you show up in a class every week for a few months and go through the step-by-step plan, knowing that at the end of it you’ll have learned the thing you want to learn. It’s not easy, but it’s predictable.

(Shameless plug: this is the reason I started DailyPath with Ben Rasmusen. We’re both self-learners and we’re building a platform to help people learn and accomplish new things together while side-stepping some of the traditional difficulties with self-learning. If there’s something you’d like to learn, please check out DailyPath.com and sign up.)

If you’ve tried self-learning, what kind of results have you gotten? What works or doesn’t work for you?

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In January 2008, as part of our trek around Asia, my wife and I boarded a train in Hong Kong and traveled to Beijing, a journey of more than 1200 miles. The train was one of the nicest I’ve been in, clean and airy, private rooms with ensuite bathrooms, and electric outlets in each car. But of course no Internet, and we didn’t have cell phones for China. However, the journey to Beijing took about 24 hours and was pleasantly uneventful.

After a week of sightseeing in Beijing, we boarded the train for the return trip to Hong Kong. The first few hours went as expected, but then the train ground to a halt. We assumed it was just a minor problem, but the minutes turned into hours and it was almost 12 hours before the train moved again. This pattern would continue for three days, with us sometimes sitting for 24 hours on the track without moving. None of the train staff spoke English (or were willing to), so we didn’t really know what the issue was. I was bored and frustrated within a few hours the first time we stopped, so I wandered down to the dining car to have a beer. That’s when I met the old-timers.

The first guy was an elderly British man who taught at the university in Beijing. He was a big guy, a little gruff, and with that utter lack of concern that probably only comes from living in China for years and being used to these sorts of snafus. He spoke enough Mandarin to determine that the cause of the delay was weather-related, but that was the only info he could get out of the staff. Another elderly man, also British, took to joining us in the dining car and the three of us spent the better part of the next few days chatting over beers.

I don’t recall if it was a lack of reception or what, but for some reason their cell phones weren’t working properly, so we were effectively cut off from the outside world, so all we could really do was drink and talk.

And talk they did; they both had led fascinating lives, lived and traveled all over the world, served in the military, had multiple interesting careers. They told me about their travels, their jobs, their families. And we must have drunk cases of that shitty Dutch beer.

The level of connectivity and reliance on gadgets does worry me sometimes, but not because I wonder what will happen if it’s missing. People adapt quickly, so I doubt that losing access to our technology would be more than a temporary frustration. No, I worry because I wonder what we’re missing because we have the technology in the first place. The chances of me talking for hours with an elderly gentleman today are effectively nil, unless there’s some kind of blackout. There’s just too much to do and see online for me to wander down to a bar and spend a couple hours talking to a total stranger. And it’s not just me, either…all the strangers are busy too. Even the old-timers are on Facebook now.

I don’t recall a lot of those three days, but I do remember those conversations in the dining car, over lukewarm cans of Dutch beer. And thinking back now makes me feel…wistful? I have a sense of sadness, because maybe these kinds of opportunities for connections were once around if you looked, but now they’re disappearing altogether.

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