Jason's Blog

Ditch the safety net, you slacker.

I was a slacker growing up.  In fact, I prided myself on it.  

Great standardized test scores and shitty grades? That must mean only one thing (I thought) - I was a genius who chose not to apply himself. Imagine how good my grades would be if I tried.

Didn’t study, but solid SAT scores? Imagine (I thought) if I had only studied, my scores would be off the charts.

Out partying the night before a big hockey game and still played a decent game?  Imagine (I thought) how amazing I would be if I only got a good night sleep like everyone else.

At the time, I legitimately believed this bullshit. I thought I was some wonderkid, as I measured my success not based on what I was able to achieve, but on what I was able to achieve without applying myself.

In hindsight (and I suspect, I knew deep down at the time, as well), I knew this was bullshit.  Did I really know for sure that I would be amazing if I applied myself?  Certainly not. Was I terrified about what would happen if I applied myself and was not exceptional?  You bet.  I was afraid to fail, and used my slacking off as a built-in excuse and safety net - if I failed, I could always blame it on the fact that I didn’t try.

This is an awful trap.  Somewhere along the way I thankfully broke out of this, and started measuring myself on absolute success, versus “success based on minimal effort”.  It is essential to do so if you want to achieve great things.  And I’ve been infinitely better off for it.  Every once in a while I fall into the trap yet again - like with my Boston Marathon training this year.  But I’ve got a much better pulse on it, and am watching it constantly.   

I know I’m not the smartest in the room, or the most talented.  But I try to make sure I outwork anyone else out there - hard work is my superpower.  Now I’ve got the opposite problem, which is that nothing I ever achieve is good enough.  But I’ll save that post for another day.

The Rise of the Invisible App

This post initially ran in Fast Company April 19, 2013

Our phones have become an extension of ourselves, so much that we get anxiety when we leave them at home. Nearly 84% of people worldwide said they couldn’t go a single day without their phone, according to Time. But fewer of us consciously think about the potential for our phones to get to know us, just by virtue of being on us all the time.

Now, wearable technologies like Pebble and Google Glass are changing the way we interact with our phones and how our phones interact with us. With these innovations come big opportunities to transform how we go about our lives. But in order for phones and wearables to be truly transformative, the apps that run on them will need to become invisible.

Wave one of the app revolution has been a great first step. Now you can keep track of your daily calorie intake, your personal spending against budget, find driving directions to your destination, and many other functions that help make our lives easier. But each of these apps still requires a fair bit of work, and as a result, many people aren’t sticking with them over time. This problem is compounded as more apps proliferate, and as people’s overburdened schedules continue to get crazier. A shining example is email. It is engrained in our business culture as an efficiency-driver, but increasingly bogs people down with more and more required actions that disrupt the flow of their workday. Lots of companies are out trying to tackle the email challenge and make the technology more invisible, before people declare email bankruptcy and throw in the towel altogether.

The second wave of the app revolution will be the quest for invisibility. Invisible apps run passively in the background, meaning they are always on collecting data, with no action needed to enable them. The information that they surface is proactive and timely, without you, the consumer, needing to look for it. They leverage many data sources, including other apps, and the more they know about you, the smarter they become. As the technology fades into the background and these apps get better at solving everyday problems effectively, they will become indispensable across more and more aspects of our lives. 

This quest for invisibility is already in progress. Google Now, for instance, not only prompts you when it is time to leave for your next meeting, but it tells you which route to take given current traffic patterns—without you having to ask. Uber doesn’t just let you book a taxi from your phone, it shows where the car is in real-time as it approaches, how many minutes away it is, and prompts you as it is arriving so you can head outside just in time. Square doesn’t just enable merchants to accept credit cards via their phones, but also lets you place an order just by saying your name while inside the store. 

While these examples may seem like magic, it’s only the beginning. As your phone has more sensors in it, and more access to integrated external sensors, it will continue to know more about you and your surroundings. As this occurs, the friction involved in using apps will continue to decrease, and the proactive insight and value that these apps provide will increase exponentially over time.

I’m not claiming the robots will take over quite yet, but as apps become more invisible, we can start to live more productively and get closer to reaching our fullest potential.

How scaling a company is like riding a motorcycle

When I was younger, I had a motorcycle. In fact, I LOVED that motorcycle (see pic below).  Learning how to ride it was interesting, to say the least. I have quite a few embarrassing stories I could share that I’ll save for another day.

One of the most non-intuitive things about learning how to ride a motorcycle is how to handle turning.  When you are going around a turn, in order to turn left, you need to countersteer and turn the front wheel to the right. And if you are turning right, vice versa. This is the opposite of what you would intuitively expect, as on a bicycle (for example), it works in the reverse.

Even when you think you get the hang of this on a motorcycle, it is put to the test the first time you don’t lean quite hard enough into a turn and realize you aren’t going to make it.  Instinctively, you want to hit the brakes and stop leaning so hard, but doing so will only make the situation worse and pretty much guarantee you won’t make it. The best approach is rather to stay off the brakes, push the front wheel harder in the direction it is already going, and lean harder into the turn.  This is not initially intuitive, but it becomes second nature as you get more comfortable on the bike.  

There is a similar phenomenon that occurs when scaling high-growth companies.  In the early days, everyday issues get resolved by rolling up your sleeves and addressing them directly.  This is the intuitive way to solve problems.  But the larger your company gets, the more you need to get yourself out of the weeds of everyday issues and trust/empower your team to address them effectively on your behalf.

You’ll think you’ve got this down as you navigate different issues, until a tough one comes out of nowhere and you need to think fast on your feet.  You will intuitively want to revert to addressing tactical issues yourself, but it is important to resist this tendency.  Like turning while on a motorcycle, the best way to make it is to stay off the brakes, lean harder into your team, and trust that they will come through for you.  While this may not be intuitive at first, it becomes second nature as you get more comfortable on the bike.

New Year’s Resolutions Are…

Our attempt at a viral marketing campaign to make light of the fact that the success rate on New Year’s resolutions is so low. With some simple tweaks to the model, the success rate gets MUCH higher.

Also our secret attempt to turn Larry into a cult phenom like the Old Spice guy. I think we still have some work to do :)

runkeeper:

See what Larry has to say about New Year’s Resolutions, and go here to see if you can make a worthy one. 

This is my shot.

It’s been a while since I’ve done any blogging.  Between trying to scale a company and adjusting to being a new dad, the past few months have been the craziest of my life so far.  When I read Dave McClure’s blog post today about being a late bloomer, I couldn’t resist taking a quick break from real work to crank out a post of my own.

Dave’s post resonated with me on several levels.  I too am a late bloomer, and I too feel like I haven’t proven shit (and to be clear, I have proven way less than Dave has).  I remember in first grade when my teacher used to call me gifted due the scores I got on some stupid standardized test.  I was the fifth grader who went door-to-door to every local business selling sponsorships for our local hockey tournament.  The kid who organized the other neighborhood kids into a snow shoveling business.  The kid who was so proud of the job he got at the local sporting goods store when he was 15, especially because he got it all on his own.

But somewhere along the way, I started caring less about achievement and more about partying and having fun.  I started skipping classes, not doing my homework, and gliding through school with as little effort as possible. I went to a good college, but only because the hockey coach said he could get me in.  I was actually pretty sure before I went there that I wouldn’t like it, and sure enough, that was pretty much the case.  I took the easiest classes I could find, and barely applied myself at all for 4 years straight.

Then I got into the real world.  While I worked hard in every job I had, in 10 years of working I never spent more than 2 years at the same company.  I would follow a similar pattern at every job… get in, be thrilled about drinking from a fire hose and bust my hump working non-stop for the first year or so.  At about the year mark, I’d start to feel like I wasn’t drinking from a fire hose as much, and I’d start to get the itch to do something different.  And 3-6 months later, I usually did.

The entire time I was going through this journey, all I wanted was to ‘find my thing’.  I was hugely impatient, and when I couldn’t find it, it frustrated the hell out of me.  It got to the point where I wasn’t sure if I truly hadn’t found the right thing, or if maybe there was no right thing and I was just destined to be a slacker that never did anything exceptional in his career.

Then, at 31 years old, I finally found something I cared about deeply enough to set out and build a company around.  When I did, I just knew it was the right thing for me, and from that moment forward I set out aggressively to make my dream a reality.  Just like every other new journey I had set out on in the past, I came out of the gates drinking from a fire hose and working around the clock.  But this time was different.  It wasn’t practice before the big game any longer, the big game was finally here.  4.5 years have gone by and I am still drinking from a fire hose each and every day.  Each new milestone that the company gets through brings a whole new set of challenges, and continuing to take it through new milestones in the future is about the most exciting and rewarding thing I could ever imagine doing.

I don’t know what the future holds, but I know I feel very fortunate to have finally ‘found my thing’.  It has all of the ingredients that should hold my interest over a long, long period of time, and honestly, I don’t know if there is anything else out there that could do the same.  While there may be, why would I ever chance it?  This is my shot.