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. Before you cry foul and try to define love for me I simply want to say that my definition of ‘love’ is probably a tad looser than your traditional definition; however english simply lacks the appropriate emphasis. The point is that I’ve experienced deep heartfelt emotions for several people and have also experienced the deafening heartbreak of having to let them go (except possibly one, who ironically I met on Tinder and lives in Seattle… but that’s a tale for another day). 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 :)

Lifestyle Business Challenge – Month 1

Backstory

I quit my job and will be traveling around the world for at least a year. The lifestyle business challenge is a self imposed goal to have $5000/month in recurring revenue from various software products at the end of the year.

Month 1 (August 15 – September 15)

Since I didn’t officially leave my day job until August 30th it was a bit of a slow month, but this post should give you an outline of where I currently stand with existing products. I’m leaving the United States October 20th and have taken a couple consulting gigs to help pad my savings prior to traveling but will continue to push out my own products too.

Existing Products

My existing products include the following iOS Apps:

Results – $296.84

~$300 is pretty consistent with what my iOS app have been bringing in for the past 6 months or so. Most of that revenue comes from the phone lookup apps with about $50 to $100 coming from ad revenue from inspirational quotes

What Went Right

I managed to round up consulting hours for the next month to add a little extra to the traveling savings account, finish up my day job, move out of my house, and submit a rewrite of inspirational quotes which went live two days ago. I’m pretty happy with the new release of inspirational quotes which was my original iphone app published way back in 2008. I’ll likely be driving that app the most from a marketing perspective in the coming weeks.

I’ve managed to push myself in terms of productivity through a combination of fire in my pants and the discovery of the pomodoro technique. I’ve been keeping an excel worksheet for each of my ongoing projects and find that the time boxing aspect of it pushes me to solve problems rather than spin my wheels ‘engineering’ it.

What Went Wrong

Quite a few things hit the fan this past month which was amplified a bit by the fact that I didn’t have as much time to work on my own products as I would have liked.

I originally had hoped to teach a class on lean startup methodology mixed with intensive out of the building ‘talk with your target customers’ techniques and I put up a landing page at http://leanlauncher.com. After talking with the ten people I thought were most likely to give me good leads on candidates I gave it up as a failure. I’m confident there is value in teaching the class; but very much skeptical that the bay area is the correct location. I failed for now but will hopefully revisit the concept in the future.

I discovered that a recent update to Phone Search broke all functionality. The most recent update swapped in a keyboard that had numbers for faster entry, just like the native phone app. Unfortunately the bottom right button, which was previously ‘Search’, is actually the backspace key. That means that no one who downloaded it was able to search for anything. Not exactly a happy ending. I’ve submitted an update to the appstore but am still waiting for approval.

The inspirational quotes approval process was also pretty rocky. Originally I was rejected for not having a ‘restore’ functionality for the in app purchases that are available despite including that functionality in the top right corner of the screen. I submitted a message back to the reviewer with the requisite screenshot who approved it about 5 hours after that event. Once things went live I happened to hit a problem in which Apple’s IAP servers were having caching problems. That event resulted in IAP’s not being available for ~18 hours. There were about 5k users who upgraded who missed out on an opportunity to purchase those in app upgrades, but it’s pretty likely the the best candidates for upgrading are repeat users so it shouldn’t be a big problem in the long run.

Next Steps

In the next month I plan on finishing up client work and pushing inspirational quotes as far as it can go from a marketing perspective, likely using mobile install ads from facebook. If you are at all interested in the app I would very much appreciate a download, which you can do here: Inspirational Quotes for iPhone and iPad

 

Join The Mailing List

If you liked this post please subscribe to my mailing list. I’ll keep you updated with monthly stats as well as learnings as to what’s working for me as I strive to build a lifestyle business and suite of products. Also if you are in south america I would love to meet up with you sometime in November or December so drop me a note!


Never Lose Sight Of What Really Matters

I stumbled across this post from my old (and now defunct) tumblr account today. It is dated June 23, 2012, right after I graduated from Stanford to begin working on the startup I will be leaving on August 30, 2013.

As I take some steps away from the shore and safety of the bay area I think it’s appropriate to repost.

———————————————————–

Tomorrow marks a beginning for my current fledgling startup. We will begin pilot testing with real users, plan to get user feedback for a couple weeks while we fine tune our user interface, and then will begin to distribute our app to our customers. It’s been a whirlwind of a few months for me between graduation, moving into a new apartment, and working hard on our product.

But you know what the most important part of today was? My parents sending me a little flash animated e-card to tell me good luck, congratulations, and that they are proud of me.

That little card means more to me than any of the work I’ve done in quite a while and served as a great reminder that life isn’t about how good of an iOS app I can make, how successful I hope to be, or following the newest technological development.

You only get one shot at life. Surround yourself with people who make you happy and who love you. Don’t be fooled by money, fame, or power. You have the power to impact everyone around you if you choose to.

So stop kidding yourself into believing that extra 15 minutes of coding will get your new startup somewhere and go spend time with your kid, your wife, or someone who really matters in your life. And never forget how the smallest things can have the greatest impact on someones daily life.

Tell them people around you how much you love them, you never know when you will see them again.