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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Check out our first post below, and make sure you subscribe!

How Cheating Has Opened the Door for Real Learning

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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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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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“Don’t accept no from someone who can’t say yes.”

This stuck in my mind and has served me well ever since. Bureaucracies are built on the back of rigid rules and hierarchical structures, but even the most rigid systems need room for exceptions. But empowering individuals at all levels to make those exceptions is the antithesis of what bureaucracy stands for, so these organizations only give the exception-making ability to those at the top. But the hapless victims of the bureaucracy constantly want more exceptions than those at the top have time to handle, so the solution is simple: have the minions at the bottom just turn down any requests for exceptions to the rules as a matter of course. It doesn’t matter that those minions couldn’t approve the exception if they wanted to, because the victim asking for the exception probably won’t push it.

But if you do push, even a little, you can often get what you want. I left the Navy with about a year’s worth of college credits, across a hodge-podge of subjects. They didn’t fit the requirements for my degree at the University of Colorado, so they told me I’d lose some of them and have to take other classes instead. Unacceptable. So I fought and cajoled and bugged them until I got the decision-makers and got them to accept every last class. I didn’t lose a single credit.

Another example of this is customer service call centers. Roughly 90% of my interactions with customer service agents are negative, because I avoid calling unless there’s a problem. And they almost never solve the problem to my satisfaction. So I request to speak to their manager, at which point they balk and explain how there’s nothing better that can be done, that’s their policy, blah, blah. About 50% of the time when I get the manager on the phone, they offer me a better solution than the customer service guy at the first level did. If that’s still not good enough, I go to *their* boss, which is almost always very difficult. They very often just refuse to connect me, in which case I have to do some digging and cold-calling. But when you get that person on the phone, they’re completely empowered to solve your problem, and they often do. Kind of sad that corporate America has this kind of relationship with their customers, but that’s another story.

So decide what you want and ask for it. And don’t stop when they tell you no, especially if they’re not able to tell you yes.

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Then the Newsweek writer said something very interesting: large budget deficits are what you would expect to see in a democratic society that lacks a strong sense of priority and purpose. Instead of making the tough choices about what to fund (and what to NOT fund) based on what’s really important to us, we try to fund everything, and end up doing it all halfway and running up a huge debt.

I instantly thought of time management: don’t many of us play this same tired game with our time? We don’t want to make tough choices about what to cut from our time budget, so we juggle too many things while trying to “have it all” or “do it all”, and end up doing a bunch of things poorly, falling into mediocrity, and running up a deficit of time, money, or both. Just earlier today before hearing this story, I was contemplating my attempts to juggle too many projects and struggling to know which, if any, of them I should give up. This idea made it much easier.

I don’t want my life to resemble the current Federal government: an on-going war of different priorities and interests, vying for attention, and creating a dystopian clump of mediocrity. So I cut two projects from my life today. Maybe they’ll come back someday, but they’re officially on ice for now, and I’m down to three projects or areas that I spend my time and mental energy on. I hope to cut another by the end of the year, but that’s all I can say for now.

Does excellence require focus? Are there counter-examples? And if it does require focus, why is it so hard for some of us to just do one or two things?

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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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One of the quotes that stood out to me was this one from a teacher of Ms. Portman:

“I’ve taught at Harvard, Dartmouth and Vassar, and I’ve had the privilege of teaching a lot of very bright kids…there are very few who are as inherently bright as Natalie is, who have as much intellectual horsepower, who work as hard as she did. She didn’t take a single thing for granted.”

She didn’t take a single thing for granted. Here’s someone who had the start of a fantastic career and a clear road to stardom. The most natural thing to do with her academics would be to just coast. Or hire a private tutor to complete high school, like many underage celebrities do. But she didn’t do that. She pushed forward and accomplished as much as she could. She even published in a peer-reviewed journal while at Harvard (giving her an Erdős–Bacon number of 7).

She’s not alone though; many celebrities are incredibly smart, driven people off the screen as well. James Franco, nominated for an Academy Award for his performance in 127 Hours, apparently wasn’t satisfied with his film career and reenrolled at UCLA in 2006, receiving permission to take up to 61 (!) credit hours (as opposed to the normal 19) while still acting. He graduated in 2008 with a 3.5 GPA and moved to New York to simultaneously attend graduate school at Columbia University’s MFA writing program, New York University’s Tisch School of the Arts for filmmaking, and Brooklyn College for fiction writing. Naturally, he also occasionally committed to North Carolina’s Warren Wilson College for poetry. He received his MFA from Columbia and is now a PhD student at Yale and planning on attending the Rhode Island School of Design as well.

How depressing

I could go on…check out Dolph Lundgren or Mayim Bialik (now playing Dr. Farah Fowler on the hit sitcom The Big Bang Theory).

These people had already arrived in one sense. They had every reason to relax and just enjoy their success in their field, but they didn’t. They kept pressing forward, learning new things, reinventing themselves.

This is a lesson I constantly have to remind myself of. (Warning: egotistical statement coming up)  I’m not a big success yet, but I’m doing OK. In the last five years I’ve seen my income more than quadruple and earned the freedom to work when and where I want, on what I want. And I’m in the process of separating my time from my income. But sometimes I catch myself slowing down, subconsciously thinking that I’ve arrived somehow. Nothing could be further from the truth.

As the Apostle Paul said:

“I do not consider myself yet to have taken hold of it. But one thing I do: forgetting what is behind and straining toward what is ahead, I press on toward the goal to win the prize for which God has called me heavenward in Christ Jesus.”

Paul is obviously not talking about his career here, but this isn’t taking his words out of context. I think that being on guard against complacency is a principle to be applied to every area of life. It’s a constant danger that we have to be aware of.

On the other hand, where does contentment fit in? There’s a lot to be said for being grateful for what you have, instead of always striving to have more. There must be a sense of balance in terms of striving to be our best and not holding ourselves to an impossible standard; we should be proud of our accomplishments if we worked hard and did our best. So where is the line between contentment and complacency?

After some reflection, I think the difference is in the distinction between what we have and who we are. None of us are perfect, so while we shouldn’t beat ourselves for our limitations, neither should we be satisfied with them. We should always be pushing ourselves to new challenges and opportunities for growth, whether that’s taking a full-time course load at an Ivy League school while being cast in an Academy Award nominated performance, or just applying for that management position that’s just a little outside our comfort zone.

Just keep pushing forward and never be afraid to reinvent yourself. Who knows what your wikipedia entry might read someday?

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