Conversations about life & privacy in the digital age

Subdue the blue – It’s up to you

There was a day when all was blue
My computer seemed to catch a nasty flu
Unsure of what would then transpire
My situation was oh so dire

What of my pictures from days gone by
Birthdays, anniversaries, picnics in July
Or music collected over the years
Oh gee – oh golly – and now the tears

The documents from work there too
And my old college paper – Philosophy 202
Letters to the crushes I once had
Then some special ones to dear old dad

How could this have happened and oh so quick
It seems like some terrible cruel trick
In just a brief moment all can be gone
And now left with so little – oye… anon…

But wait – indeed – for what yonder light breaks
It is as if an epiphany did suddenly awake
I remember I remember I took steps long ago
To ensure my digital life I did forever bestow

A place for all my possessions to safely reside
Far far from harm and away from the tide
I did indeed find everything safe and sound
Amazing the glory that it can all be found

So what is the moral of this little tale you say
Be weary that something bad may befall someday
It could be an illness, a thief, or a trip
But always remember this cute little tip

Take measures ahead to backup what you’ve got
And sadness or pain you will surely feel not
Regardless of service – there are many to choose
Just use one and you can never lose…

Another Year – Another Burning Man

The other day I was invited to hear the ‘founder’ of Burning Man speak about the festival, its origins, and why it has captivated so many over the last 25 years. If you have not been or heard of Burning Man, it is a city that grows overnight in the Nevada dessert of 60,000+ people who come to explore the arts and music, let down inhibition, and search for their soul in the harsh late summer sun. For the first time in the event’s history, tickets have completely sold out.

So what is it about Burning Man? There are abundant theories of course and I do not pretend that my insight is unique. Is it the ‘gift econony’? The thumping music? The incredible art installations that liter the sand? The overall freeing spirit of the dessert? I would say yes to all the above and much much more.

Last year was my first experience on the ‘Playa’ and nothing can prepare you. Photos. Stories. Pre-parties. You can do all the research possible but this is just an experience you must know. Out there everyone is on equal footing whether a media mogul, a flight attendant, a technology baron, a teacher, a lawyer, a parent, a child – it matters not and, further, no one cares. The idea is to strip everything away (except the crazy gear of course) and think of a time in the past or in the present when life was this simple and we all helped each other through.

Burning Man 2011 – the 25th anniversary year – remains just a few weeks away now and this city is abuzz with preparation. For those who have been the excitement builds daily and for those who are on their first journey the nervousness grows. In the end, it is a wonderful alternative to our current social construct and one worth experiencing in my humble opinion.

However if you would like to go this year you best be served by hunting down a ticket on Craigslist or similar; that said, don’t pay more than face value as the act of charging more defaces the spirit of the event altogether.

The ‘Dog’ Post

I was told by the team that I could only write one blogpost about the fuzzy creature that sits beside me at the moment. So – here is my one and only post about my dog.

The first topic I would like to discuss are the two circular protrusions which dangle from below his tail. Yes – his manhood. As a new dog owner, I have heard hundreds of opinions about the right time to schedule the simple procedure to remove them. It would appear the consensus is somewhere between 6 and 18 months. And whereas they do cause quite a stir and always are at the center of conversation when he prances by, I still have no clue what to do.

Many have said that if he is still able to play with others without projecting his scent into the mix then he should be able to keep them for as long as he likes. After all, one could make a good argument that the testosterone produced is good for overall development and mass. For reference – the little guy is 10.5 months now and still gentle and sweet-as-can-be so I guess we will keep plowing along.

Curious to hear your additional thoughts if you would like to share?

The second topic speaks to a wholly different topic. By my place there is a wonderful hill with an amazing view of downtown. Dogs are able to wander freely. And given the dog-friendly nature of San Francisco, this haven is quite well and frequently visited by canines and humans alike.

I can tell you as a first time dog person that the worst element associated with having a dog in the city is bending over with that little plastic bag, forming an open crane-type position, and then tightening the wrist muscles causing the hand to clench and extract the excrement from the earth. I must tell you – this STINKS. However, it is an extremely necessary function for if this didn’t happen in the dense cities we have created today then we would all be stepping on some sort of shit all the time.

Now to my point – I am constantly impressed at the communal effort and responsibility taken by all to ensure we don’t spend each day with our heads down leaping and dodging like frogger. After all, it would be relatively easy to simply look the other way when that ‘squat’ appears and pretend like you don’t see it (or smell it). And at night when no one is around, little is keeping you from partaking in that night cap (or crap). Yet – as a citizen who now falls into the category of ‘dog owner’, I do feel the responsibility to ensure that the world has less shit in it then when before I accepted this role.

So to all those pooper-picker-uppers out there, I appreciate the comment on the larger society you are making every time you bend down by proving that social responsibility does exist and is in fine form. Thank you.

What I’ve learned from a natural expert in customer crisis management

In light of current events such as the AirBNB situation, I’ve now recognized how fortunate I am having a cofounder who truly understands how to have conversations with customers, especially in the most trying moments.

When the first customers started using version 1.0 of SpiderOak in 2007, inevitably some people ran into serious limitations with the software. In the first version of our Sync product, I recall a particular incident about SpiderOak mishandling deletions of the old Windows/MSDOC 8.3 “short file aliases” and how they expanded to long filenames that literally had a grown man in tears when it seemed like all his years of pictures were gone [1]. People are naturally very concerned about their data, and as a backup company, relieving that concern is our primary job.

Thankfully, right from the beginning Ethan intuitively understood things about these situations that I needed to learn, fast.. “It’s not about the problem. It’s about how you handle it.” Here’s what Ethan always made sure happened:

  • Greet everyone who contacts you warmly, regardless of their reason or their original tone. “First, Thank you for your email and your interest in SpiderOak. As it pertains to your XYZ….”
  • Respond as soon as possible to the customer, with or without a solution. The first response needs to communicate that we care and are working on resolving the problem.
  • Make it very clear, somehow, in the response that we actually gave individual attention to this specific customer and did not send a canned or copy-and-paste reply. This is about perception, not reality. A simple, minimal, formula for this might be, “I’m sorry to hear you’re having trouble with THEIR OWN WORDS DESCRIBING THE PROBLEM,” but of course you can do better. Find small ways to make your own thoughtfulness blatantly apparent.
  • “Customer service is about pride-swallowing.” For example, if for some reason you can’t respond promptly (it happens), don’t make an excuse and explain how other important things kept you away. Just apologize. “Sorry for the delay in sending this reply” is sufficient. It doesn’t matter how the problem happened [2].
  • Just admit it when you’re stuck. Some obscure problems maybe extraordinarily difficult or impossible to solve. At scale, all the bizarre edge cases find expression. You’re not going to be able to solve everything. Here’s the essence of what we tell a customer if we have tried hard and failed to resolve their problem: I want you to know this is one of the harder problems I’ve encountered lately. I very much appreciate your patience in working with us to try to solve it. At the moment I’m scratching my head and out of ideas. If you’d like a refund we can do that today. If you’re agreeable, I’d like to keep trying; we’ll suspend your billing until we get it figured out, and I suggest we proceed just by trying to simplify your configuration until we find a base that works…”
  • Occasionally, extraordinary circumstances warrant extraordinary response. It does not need to be a policy, but just use regular human judgement and do the right thing by the customer. I remember one time a SpiderOak customer had forgotten her password and was very emotional about the prospect of not being able to decrypt her backup data [3]. Ethan called her and sat on the phone being cool, smooth, and sympathetic while guiding her through conversational memory retrieval techniques to help her remember the password she had set. In a few minutes, all was well. No one could have handled it better.
  • Say something pleasant/encouraging/uplifting/funny at the close of almost every conversation. If you’re not this type of person naturally it might seem meaningless at first, or perhaps even be difficult to think of unique responses all day that don’t sound canned, but practice makes it easy. It’s just one last demonstration of simple thoughtfulness.

In those early days, Ethan answered all our customers himself, and continued doing so for as long as any one person could, and still answers quite a few today. Now Laura and several others have joined our customer relations team, and each has brought their own unique style. I’ve learned something new from all of them, and will of course continue learning the most from our many wonderful customers.


  1. This story eventually had a happy ending because of SpiderOak’s design choice to always fully backup files before deleting/overwriting them during a sync, so that any previous state can always be recovered.
  2. Maybe when your audience consists of engineers it matters, but I recommend setting that explanation apart from the rest of the conversation about the things you know the customer cares about. “If you happen to be interested in the engineering details …”
  3. Our ‘Zero-Knowledge’ encryption policy means that our customer data is only readable by our customers, not by us. Not the filenames, foldernames, or anything. If the password is forgotten, the data is not readable. During signup, instead of agreeing to an EULA, customers agree to a password policy that says that they understand their data is readable only with their password.

A First

Last night I had the honor of serving on my first panel discussion. As you might imagine, it was on the role of the big toe and its relationship to the other four toes it serves. Or – the future of the cloud and where we go from here. There were several other panelists covering various aspects of the ‘cloud’ and it was interesting to hear their take. A few takeaways…

1) It seems – based on the discussion – that everything is moving much more toward the small business and enterprise market and the consumer side will be won over by a few big players – Apple, Google, Microsoft, etc… This has certainly been the argument all along in opposition to us ‘smaller’ players but I am just not sure I agree. One of the big obstacles I have always seen with the big players is a restriction they all place on themselves – compatibility. They build their ‘stuff’ specifically not to talk to each other and as data resides across more machines, devices, and platforms it seems there will always be a place for someone to understand and organize regardless of restriction.

2) Differentiation of the different data elements and how we use them. Similar to how we live everyday, there are shirts and pants we wear quite often and others we pack away for special events or different seasons. Data is very similar to this and whereas you might not need to store your old prom dress or tuxedo in eyesight – so too is there data that you might not need to interact with day-to-day and therefore would prefer cheaper cloud storage. That said, documents you interact with daily would sit more front and center in the closet and thus you don’t mind paying a bit more.

3) Privacy is now and will continue to be a growing concern. The creation of our ‘zero-knowledge’ encryption was in direct response to what we felt would always be an important need as the cloud grew and grew and became more mainstream – privacy. However, there are varying degrees here as well.

4) Continued increase in the creation of data and the next wave. The discussion moved more to biometric devices able to capture heart rates and blood pressure and other body measurements into the cloud and then have automated systems created by doctors to alert you if there was potential trouble. Will be an interesting future…

In the end, it appears the ‘cloud’ is here to stay and will continue to grow and affect our lives in new and exciting ways. As for myself, I survived my first panel relatively unscathed as I didn’t spill my drink, fall asleep, insult the moderator, or say anything too scandalous about a competing CEO.

7 Posts –> 7 Days

I have decided to write 7 blog posts over the course of 7 days. Why? When asked why we climb mountains the answer always echos back ‘because they are there’. Similarly – I would like to see if it can be done and in which way it will be accomplished.

Leading up to this decision, many potential topics have come to mind. Others have been uncovered over the course of conversation and national spotlight. So now the problem exists as to which one should be the first…

The US seems to find itself in a place it has never been before – a week away from defaulting on its responsibilities. Wherever one might fall in this conversation politically, it seems everyone is to blame. From not getting into the fight soon enough to placating a very small minority to a complete and utter misunderstanding of what is being done, this debate about who and what and when will ultimately have long lasting and devastating effects. Is it the lack of responsibility our generation accepts? Or the advancement of an American ideal run so far down the line that the original principles have been fully lost in translation?

Ultimately, it is the rigidity of a few that will take down the many. Radical thought and projection seems always to be the root cause as history has proven time and time again. This country – the founding fathers – believed there to be a truth existing in a middle; however, through a lack of commitment/historical perspective, we find our old friend staring us back in the face. I suppose as humans it is just inevitable.

In 7 days we will know the outcome. And unlike the last day of a mountain adventure, may I be writing my final post about something other than descent.

More fun with SSL certificate verification failures

Some of you who tried to access a couple hours ago may have noticed a security warning from your browser complaining about an invalid certificate.


No, we didn’t forget to change the storage certificates again. In fact, the new certificate was purchased back in April.

Turns out there was some fun to be had with our new SSL certificate. (SSL is the mechanism that browsers use to encrypt your connection to the server, giving you the nice padlock icon so that you know websites like are secure.)

Geotrust changed their certificate roots due to some weaknesses in the old one, which meant that there was not only a new root, but also a new intermediate RapidSSL certificate thrown in for good measure. (The root is the certificate that browsers use to verify that all certificates are genuine. The intermediate certificate establishes a chain of certificates from the root to the certificate used by an individual website.)

This took me a few minutes to figure out, but once I got the extra intermediate certificate thrown in there, the website was happy.

Unfortunately there was another problem: the SpiderOak client didn’t know about the new certificate root. This would have affected anyone who was trying to complete their first signup or create a new device in the SpiderOak client.

The core of the problem is that by default, Python, the language that SpiderOak is mostly written in, does not verify SSL certificates at all, so we were forced to roll our own verification routines. We whipped up our own system that simply packaged the certificates in the client itself, which was better anyway because it didn’t rely on sometimes broken external SSL certificate chains. Today’s problem is the obvious downside. Our developers responded quickly and pushed out new builds with the updated certificate in about an hour.

So if you’ve had problems signing up, we’re sorry. We screwed up. Please download the latest version and try it again. I’ll be over here taking my due flogging.

TL;DR: All your existing backups, syncs, devices, shares, and everything else are fine. The next time you add a new device to your SpiderOak account, you’ll need to download the latest version of SpiderOak.

Update: If you tried to sign up during this time, you should be receiving an email from us shortly, along with an extra gigabyte of free storage to show our appreciation for your patience.

Update 2: It turns out that some older Android phones (older than Android 2.3) don’t include the newer CA roots! (Although, the original iPhone from 2007 does have those roots included via OS updates, and some Android vendors seem to include them also, so it is somewhat unpredictable whether a given phone has them.)

So, we’ve had to add an intermediate certificate to for older Android compatibility. We’ve published the desktop client revision 9830 which also recognizes this additional certificate. Once again, all existing devices, backups, syncs, etc. are fine. You’ll need the newest SpiderOak the next time you add a new device to your account (which is generally the best practice anyway.) -Alan

SpiderOak Looking Inward

Over the last several days, the SpiderOak team gathered in Kansas City. Of the many activities during our time together, one particular exercise involved looking internally and thinking about what each of us would improve about SpiderOak. It was left rather open-ended on purpose and the responses were varied and raw.

Given that transparency is the most important part of who we are as a company, we published these thoughts below so you might all know what we think about us. After all, internal reflection is crucial to strong and balanced growth.


I would improve SpiderOak by tightening the focus of our application to
provide a backup-only edition, in addition to our standard product.
This would make it easier to run SpiderOak on network storage boxes and
other ‘small’ devices. – Bryon

I would have a working read/write mobile-friendly API. – Matt

I’d make it easier to control how long and how often SpiderOak stores historical versions. If users could tell SpiderOak to delete these versions after a certain amount of time, or not store them at all, it would make space management much easier. – Laura

I believe that communication is the most essential part of any successful team. Developing a better understanding of everyone’s roles and responsibilities will improve all aspects of SpiderOak. – Alli

I want to redesign the website to be more mobile friendly, especially for shares/login. It’s something we really should have to provide mobile access on platforms we don’t officially support. – Chip

I would redo the web account pages to be more intuitive and readable. It would be nice to be able to bookmark pages, easily read what’s on them, etc. – Ben

We should hire more cute women who are into scrawny pale guys like Chip because it honestly bothers me that someone so brilliant isn’t more directly benefiting womankind. – Alan1

Currently, there are very few ways to gauge how the WL Program is growing. I need to know when a new user signs up through our WL partners, conversions from free to paid users and past due users. Better reporting would help me understand what resources we can provide to our partners to maximize profits. – Michelle

I imagine there will come a day when I am unable to recollect many of my memories from childhood. If only SpiderOak could figure out a way to back up the smell of my grandmother’s kitchen when she was baking chocolate chip cookies or allow me to share the feeling of her warm hug. – Linzi

Different internal event detection and reporting for servers. – Doug

I’d like for us to improve/develop a sense of community in the workplace by getting employees more involved in work-sponsored activities. Take an interest in the personal lives and interests of employees…. Helps the creative juices flow. – Jovan

Something I would like to improve about SpiderOak is the communication to customer relations. It would be nice to know, as quickly as possible, when there are problems with the program such as server issues, or a bug. – Dana

I think it would be great if we included music videos as part of our marketing efforts. SpiderOak Journey cover band? Fans singing about SpiderOak to the tune of trashy pop songs? Yes, please. I think that would be awesome, but if you’d prefer something more serious for the blog post:I’d love to see more opportunities for users to share testimonials and stories about SpiderOak (apart from what they might post on the forums). This will also help prospective users see from other users what we’re all about =) – Gwende

We should try to double Doug’s smiling time. – Alan2

I would implement a new billing system to better handle varying payment methods (CC, PayPal, etc). And to facilitate all the various things we bill and payout for, like whitelabels and affiliates. – David

Develop easy to use, web based administration tools for internal
functionality and processes. Making build processes and administrative
tasks easier to delegate and perform independently. – Daniel

Open source the SpiderOak client software. And I would love to have an office or work space in my city. Working from
home is great much of the time, but meeting with coworkers and bouncing
ideas off of each other is priceless. – Paul

We should become better champions for the cause of privacy in the upcoming era of cloud computing. And we need a live funk band performing during all company meetings. – Alan3

We should thank all that’s holy we’re not PSN. We do things better than that. – Gareth

Improve the communication between our various departments and create more opportunities for us all to gather. – Ethan


Now that you know what we think – let us know what you think. We always promote positive and helpful feedback from our community and look forward to hearing your thoughts / ideas / suggestions on what we can do better.

Ending with a quote from Joseph Chilton Pearce… “Seeing within changes one’s outer vision.”

Creating a Grayscale Icon – We’ll Leave That up to You

Through the SpiderOak Vine, we keep hearing that our Mac users would really enjoy a SpiderOak grayscale icon for the toolbar – keeping with the consistency of the overall Mac look & feel. After an internal conversation on the topic, we thought the best way to make this happen would be to open it up to our community to see what you all could come up with.

Here’s what you’ll need to do:

1. Make a SpiderOak grayscale icon (keeping intellectual property and copyrights in mind)

2. Send an image file to on/or before June 24

3. If you are so inclined, share the contest with your friends and family

Here’s what we’ll do:

1. Ogle over your icon submission

2. Pick an icon that we like best

3. Boost your account 20 additional GBs & feature you in our Release Notes

We are eager to see all your submissions! There are of course several tools that will help you along the way but we will leave those choices up to you. :-)

Special ‘Secret’ Note: Along these lines, we have been investigating a move toward a much more native look & feel across all of our supported platforms. Who knows – perhaps this will be available soon…

What are friends for?

It is good to have friends. They are there when you need a helping hand, a shoulder to cry on, or even to watch your dog for a long weekend. As we think about our friends at SpiderOak, it dawned on us that friends deserved quite a bit given all they do for us.

Therefore, to honor our friends near and far, we are increasing the amount of space users can obtain through the SpiderOak Refer-A-Friend program to…

50 GBs of FREE Storage for Life!

So here is how it works: if you refer a friend who signs up for a SpiderOak account then you and your friend will receive an additional free GB of space. Easy.

The SpiderOak Refer-A-Friend program is open to both free and paying users so everyone can earn an additional 50 GBs of free storage. You can visit our Refer-A-Friend page now and get started immediately: Refer-A-Friend Signup.

As always, we are eager to hear your thoughts and ideas so please don’t hesitate to pass them along. Remember – having friends is a wonderful gift & should always be celebrated.