Insanely Simple

I recently picked up the book Insanely Simple by Ken Segall after my roommate insisted it was a ‘game changer’. I’d originally pegged it as a book on minimalistic lifestyles, but it’s actually a book about how simplicity has driven Apple’s design decisions for most of it’s history. Segall touches on Steve Jobs illness and quotes a few lines from the commencement speech he gave to Stanford in 2004.

Remembering that I’ll be dead soon is the most important tool I’ve ever encountered to help me make the big choices in life. Because almost everything — all internal expectations, all price, all fear of embarrassment or failure — these things just fall away in the face of death, leaving only what is truly important. Remembering that you are going to die is the best way I know to avoid the trap of thinking you have something to lose. You are already naked. There is no reason not to follow your heart…

No on wants to die. Even people who want to go to heaven don’t want to die to get there. And yet death is the destination we all share. No on has ever escaped it. And that is as it should be, because death is very likely the single best invention of life. It is life’s change agent. It clears out the old to make way for the new.

… and yet Steve Jobs continued to work until his death in 2011. For me, close encounters with death and radically changing perspectives from traveling have led me down the path of savoring life, rather than influencing change like Steve Jobs seemed to have done even after getting a terminal diagnosis. I’m not sure there is a correct answer here but it does beg certain questions. Am I spending my most valuable asset, time, correctly? Am I simplifying my life down into moments that maximize the happiness I get out of it? Should I even be maximizing my own happiness, or is that too selfish? Why aren’t I out trying to change the world to make it a better place so that others can lead happy lives too?

AppleWatchWeekly.com – A Newsletter Experiment

From my corner seat at a Silicon Valley startup, the Apple watch is pretty much everything the media talked about this week. As an iOS developer it means brand new exciting times and a future that holds at least one more piece of wearable tech.

I’ll be building out a few apps for launch day, but I’m also going to be experimenting with a curated newsletter for all things Apple Watch in an alternative bid for readership and possibly even a new revenue stream. I’ll likely be posting more numbers (and hopefully sponsorship revenue numbers!) at some point, but for now if you are interested in getting a newsletter every week related to all things Apple Watch sign here:

AppleWatchWeekly.com

 

The Year I Discovered My Life is More Important Than My Startup

“They just fired me”

The words caught in her throat and reverberated oddly into my brain. I could feel the moment starting to warp into some sort of shakespearian ‘lesson’ I was supposed to latch onto and spit out at my junior employees years into the future; and yet I simply stared staunchly back into that statements twisted face in denial. Standing before me was one of my best friends who I had recruited a year earlier to be a linchpin in a company I helped co-found. That moment would cause me to leave the company. It also changed my life forever.

Beginnings

My life up until this moment was a fairly standard american dream story, and I was doing well on that scale. Born to middle class parents in the suburbs of seattle; I tottered my way through early childhood with an incredible amount of love and support. In high school I would captain two sports teams, graduate at the top of my class and be lucky enough to get an opportunity to attend and wrestle for Stanford.

Fast forward 4 years and I graduated with a degree in Computer Science, which essentially means I was now able to do weird things with computers and had managed to vaguely understand some basic theoretical computing knowledge.

Startup Echo Chamber

As I progressed through my undergraduate studies I became infected by the startup itch. It started small but was compounded by the seemingly mainstream idea that all computer science people were supposed to be the next tech millionaires. After all, we had all been successful thus far into our lives…. what was to stop us from becoming the next Zuck or Gates?

Halfway through my senior year of college I was put in touch with three people (two domain experts, one serial entrepreneur) who were interested in forming a company. I was the first technical guy on the scene. We had a real team with some serious depth, a small amount of seed money in the bank and hopes of wild success both monetarily and in the industry we were hoping to help.

My wrestling teammates would joke that I would be the first guy to be a millionaire. He’s got it all right? Engineering degree, a fledgling startup…. oh and he’s young. That means he can pound the ‘work’ drum 24/7 like ‘all’ the successful startups stereotypically do.

Soul Searching

I had worked on the company for a year and a half prior to the firing incident. I wasn’t unhappy with my life but it had the feel of suburbia to it despite the fact that I was 24. I rarely tried new things, dates were virtually nonexistent, and I’d let friendships flounder all in the name of a startup. Forced to choose between a friend who I felt had been wrongly fired and the startup I’d help nurse from infancy I decided to choose my friend, a decision I’m proud of.

My lease ended two weeks after I told everyone I was leaving, and after being best man at a fairytale perfect wedding I was sick of the status quo. My friend called me up shortly after….

“I’ve got a year before I start medical school. I’m leaving to travel South America for two months, you should come with.”

…and there it was. An adventure I hadn’t even considered taking was now staring me straight in the soul just daring me to say no. Equal parts scared and exhilarated I decided to freelance for a month to get some extra cash, and then I jumped straight into the abyss of traveling.

The Most Soul Stretching, Personality Bending Year of My Life

I ended up traveling for 9 months, and it was the best decision I’ve ever made. I spent 2 months in South America, 1.5 months in Ireland/England, 1.5 months snowboarding and 4 months in Southeast Asia. With the exception of South America and a stint in Vietnam I traveled solo.

Honestly, words cannot describe how much I have changed, nor accurately catalogue the experiences I’ve had while crisscrossing the globe with nothing but a backpack. I managed to knock out traditionally stunning bucket list places like Macchu Picchu, Bagan, Angkor Wat, and Stonehenge. I’ve also managed to sleep in an oasis in the middle of one of the deepest canyons in the world, pulled a snooze on several villagers floors, and done things that shouldn’t be written about publicly in many a hostel dorm room.

And yet none of those majestic places hold a candle to the people I’ve met. The sheer fact that as a solo traveler you have the opportunity to walk downstairs and interact with people from all over the world is simply stunning. It refines your own personality as you retell your life story while simultaneously bringing out the inquisitive extroverted side of you. There are simply so many people to meet with interesting tales that it’s stupid to not be start conversations. Usually I ended up tagging along with other travelers for days or weeks at a time, which makes the ‘solo travel’ thing a bit of a misnomer. Several people I have met I now consider to be lifelong friends who I hope to see again (oh and special shout out to you ‘Sleazy Riders’, the appropriately dubbed motorcycle gang I was a part of in Vietnam).

On an emotional level all the travel has caused me to be more blunt and honest with my feelings without fear of rejection. I fell in love four times. Well maybe not love in the traditional sense, but  I’ve experienced deep heartfelt emotions for several people and have also experienced the deafening heartbreak of having to let them go. For a guy who had previously only been in two serious relationships, I’m much more developed and in touch with emotions as well as confident in what I want.

On a personal level I’ve also managed to find peace in the moment. I’m much more content and happy, largely because I’ve discovered that my life as a whole is head and shoulders more comfortable than 99% of the people in this world. If a naked, barefoot little kid in Myanmar who lives in a bamboo hut can jump up and down in excitement before giving you a high five; surely my petty problems are miniscule. Perspective is a wonderful gift.

 The Valley Round 2. This Time As An Employee

Since the beginning of September I’ve been back in the valley, and have taken up a development position at a seriously cool company called Curious.com. The team is an incredible mix of diverse personalities that mesh astoundingly well, and being the destination for learning anything is a goal I sincerely hope we fulfill.

Since being back I’ve been camping, started learning how to draw and play guitar, been on 4 dates, work out 3-5 times a week, baked some delicious muffins, ridden the majestic beasts known as roller coasters and have spent time with friends long neglected. I’m finally filling my life with experiences that touch me as a sentient being rather than some robot drone who supposedly gets his adrenaline kicks from development or company milestones.

I’m not trying to make a point about founders vs employees. I am trying to make a point about all of us as people. Do you really want to look back on your life and remember that time you increased the lifetime value of a customer by $1 through an A/B test? Even if you are ultra successful, will your life become 100x better because of an influx of money?

Cherish the time you have. Work on problems you want to see solved, but work with people you want in your life. Get out of your inbox and go push the boundaries of your existence. Cast away your comfort zone and wrap yourself in the unknown. I’d like to believe there is a clock counting down the number of days we have left to live that exists somewhere in the magical organ we call the brain. I have no idea when my clock expires but I do know that someday in the future when that clock expires I will confidently proclaim that I have lived. This past year has given me a taste for life, and I will boldly stride through the next years of it seeking more.

Take a step back and give your life a hard look. We don’t all have to live a drone like existence of work 24/7. There’s more, and I urge you to discover it.

 

Postcard Panda is now live!

Postcard Panda, an app that allows you to send a real snail mail postcard from your iPhone is now live in the app store! The idea stems from the fact that during my south american adventures I managed to buy a lot of postcards but never managed to actually drop one in the mail which I felt a little bad about.

The app is powered by Lob.com, and the artwork was skillfully designed by David Laplante.

You can download it directly from here:

Postcard Panda on the app store

or view the landing page at:

Postcardpandaapp.com

Two Questions That Will Make You A Better Leader

To me a highly effective leader is someone who leads from the back. Like a good user interface an effective leader frames the problem, points their employees in the right direction, and then gets out of the way. If a leader has surrounded themselves with the right people (aka people smarter than themselves), getting out of the way allows your organization to fully unleash their collective creativity on a problem and grow closer together as a unit.

As a leader from the back it’s imperative that you are continually getting feedback from your team, but it’s often an awkward and formal experience. One leader I had the opportunity to work with briefly, Matt, asked me two questions at the end of every week (and I asked him the same questions) that grew the rapport between us incredibly quickly. Sit an employee down and try them out, you’ll be surprised at the results:

Tell me three things I did this week that you think I did well

Tell me three things I did this week that you think I can improve on

 

Make it a conversation and ask these questions on a regular basis. You’ll learn a lot about your employees perception of you as a leader, will smooth out any issues before they become issues, and get a chance to give your employees continual feedback as well.

Quantity vs Quality In Early Stage Prototypes

Way back in 2009 I took my first Human Computer Interaction course at Stanford from my future advisor, Scott Klemmer, that sparked my curiosity with early stage products. Recently I decided to relive some memories and logged on to his 2012 coursera course where I was reminded of an incredible story that really embodies the value of low fidelity prototypes and not being afraid of putting your work out there at it’s earliest stages.

Here’s a transcript from a section of his lecture “Creating and Comparing Alternatives”:

When you’re designing, does it make more sense to go for quality and try to come up with the best possible design? Or does it make more sense to go for quantity first as a path to try and learn and understand?

There’s a story that Bayles and Orland tell about an art teacher who divides the class in half, and he tells one half of the class, ‘You’re going to be graded exclusively on the quality of the very best thing that you make.’

He tells the other half of the class, ‘You’re going to be graded on the quantity of things that you make. Doesn’t matter how good it is; all that matters is how much that you make.’

And what this teacher found was that while the quantity group was busily churning our piles of work — and learning from their mistakes — the quality group sat around theorizing, and at the end of the day they had little more to show for their efforts than grandiose theories and piles of dead clay.

So this gives us some intuition that rapidly producing many alternatives has a lot of value.

Prototyping isn’t all about just fine tuning the interface. It’s about gaining experience and learning from your mistakes as fast and as quickly as possible. Think about your ‘MVP’. Now go draw it on paper and have a conversation with a target customer.

 

More Reading:

For a deeper dive I suggest reading more about Steven Dow who does fantastic research into parallel design practices.

If you are interested in the book in question it’s titled “Art & Fear: Observations on the Perils (and Rewards) of Artmaking

One Question To Rule Them All – Getting Honest User Feedback

One of the big issues with in person user testing is that people lie to you. Not in the sense that they want to hide something from you but rather that they don’t want to hurt your feelings. There are a lot of techniques to combat this; but I’d like to share with you one of my favorite questions that really allow your users to open up to you:

“Let’s pretend this is baseball. How would you rate our product on a scale of strike-out to home run? A strike-out means ‘I would never use this product ever’ and a home run means ‘The product is flawless, don’t change anything, just take my money'”.

[User Answers… it doesn’t really matter what they say. Most likely they are going to say double so you feel good, substitute whatever base is necessary below]

“Alright now let’s say we want to make this a triple instead of a double. Not going for a home run yet, we don’t want to get too greedy. What is the one thing you think we can do better to turn this product into a triple?”

At this point you’ve allowed the user to save your ego (even if you didn’t need it) and they can now open up to you about what is lacking. Don’t fall into the feature creep mode just from this single answer, but rather use it as a tool to get inside your customers brain. If they give you a answer like ‘I want feature X’ dig deeper with a simple “Why do you feel X?” question that turns things towards a more emotional based response.

More tips coming soon!

Postponing the Lifestyle Business Challenge

Some of you may have noticed that I missed my last report of my self imposed ‘Lifestyle Business Challenge’. I will be post-poning the challenge until after I finish traveling the world. Unfortunately (or maybe fortunately) the last two weeks have been filled with adventures in South America that I will carry with me for the rest of my life. I’ve been so busy trying new things (hiked a volcano!), exploring new towns and meeting new people that I’ve barely managed to put a couple hours into any programming project.

It’s a nice change to take a step back and absorb cultures that aren’t so wrapped up in the American rat race or the silicon valley startup grind. I’ve only been out of the country for two weeks, but I will recommend backpacking to foreign countries until the day I die. This year has been an interesting journey but I get the feeling that this journey is something that will shape me as a person for the rest of my life. Lifestyle business will be my next adventure, I just need a few months to do this whole traveling thing :)

What iOS 7 Auto-Update Means For Developers

Way back when the app store first opened there was a list called ‘Just Released’ that showed a feed of apps that had been released in chronological order. Developers soon discovered that updates were also included in that feed, which caused a continuous stream of updates to be pushed out. That feed was responsible for your launch day blitz (for developers who didn’t take marketing as seriously as they should have… like me). Fast forward 5 years and the needle has swung completely in the opposite direction.

Today an update was approved for my Inspirational Quotes app. As usual I waited a half a day for DNS to figure itself out and then opened the App Store to retrieve the update but this time something magical and terrifying happened, it had already updated itself.

On the surface this feels like a win for consumers and a feature that will encourage developers to produce apps that actually create value. But a deeper dive shows a few nasty edge cases and a lost opportunity for developers for reengagement.

The Good

Auto update means more people will have the latest version of your software and will probably result in a lot less headaches when people not as familiar with technology need to update an app. As an ex mobile health entrepreneur I can attest to the fact that there is a large majority of people who have an exceedingly hard time installing apps, let alone remembering the apple id and password. Ask them to update an app and it’s enough to make some tech support lines cry. 

The Bad

As an indie developer I enjoyed the fact that the update screen was basically a small chance for me to re-grab my users attention. This is probably not as bad as I think since long term usage actually requires a compelling app, but I would be lying to say I didn’t like seeing the small bump in traffic after an update was released. It made me tingle just a tiny bit knowing that people cared enough about my app to give it at least one more shot. 

The Ugly

The ugly side effect of auto updates are bugs, and the lack of expectation management the system provides. Take for example my bank’s app. I use mobile banking heavily, and the current version of the app on my phone crashes every time I try to do a mobile deposit.

Before auto update if a bad bug was released into the wild prior to the developer catching it (aka test your apps in release mode!!!) the process was kinda simple. Submit an update as fast as possible, preferably with one of your expedited reviews, and then update your apps ‘What’s new in this version’ description to include “DO NOT UPDATE TO THIS VERSION! APP CRASHES!”. Developers pants are on fire, but at least the consumer has a chance of avoiding headaches.

With auto update consumers have a few problems. Since there is no indication that apps are updated without obsessively checking the updates tab on the App Store; they will likely go for several days or weeks without realizing the mobile deposit feature is fixed.

 Next Steps

A nice first step would be for apple to think about some way to notify users when updates occur. Something as simple as a badge indicator on the app store icon that builds up until I at least scroll though the updated list would be a good start.

As a developer I’ll probably start working on reengagement strategies a lot more seriously. Some combination of push notifications or more traditional email campaigns is probably a safe bet. It’s also a nice kick in the pants… maybe this will actually force me to create some value with mobile apps after all :)