Free Product Idea: One Fine Day


I travel quite a bit for work.  

I'm also mildly OCD, so I have a mini-ritual of sorts whenever traveling to a new city of buying a new Lonely Planet "Encounter" travel guide for that city before traveling there.

They're handy little books, pocketable at 6x4 inches.  They contain a condensed listing of major sights, restaurants and the like, with a decent detachable map at the back.  I appreciate the density of the information and also the slightly offbeat selection of places each editor includes which a more conservative guide might skip over.

The ritual part is that I enjoy adding a new book to my collection slightly more than I do using the things.  On my bookshelf, they are a visual representation of where I've been and gone, all in a nice orderly set, each city marked by a unique color on the spine.  When I arrive back home, I take the book out, place it next to its brethren and stand back to admire the set and reflect a bit on my trip.

I've gone so far as to buy a book for a city I've visited in the past and don't necessarily intend to visit again, just to pad the collection.  Some of the places I visit don't have a book in the series and so I am forced to buy one of their larger books as an ill fitting substitute, and this irks me more than I care to admit.  

Many people have this sort of relationship with travel.  One of the most cliche visual representations of a traveler is a weathered suitcase covered with stickers from various locales.  I know fellow travelers who collect kitschy souvenir spoons or refrigerator magnets in a similar way.

Ultimately, what we traveler/collectors are attempting to do is collect experiences, and yet, the actual experiences are often much more mundane and anti-climactic than our collections might belie.   

To the Product-mobile!

There are any number of travel products in the world, from television shows to books to websites.  All effectively seek to create a repository of information about places one could visit.  The good ones winnow down the vast world to a manageable list of places one should actually visit.  The best ones offer a glimpse into the experiences of people in those places, be they visitor or inhabitant.

That's all well and good, but in my experience, the place is really not the thing I'm after.  I often arrive at a location I've heavily circled in one of my trusty travel guides, only to be profoundly disappointed because it didn't match my imagined expectation of what it would be like to be there.  

It's the experience rather than the place that I'm after, and travel guides often lack clues as to how a traveler should engage with a place once they've arrived.  Also, some experiences worth having don't really have a locale at all.  Some exist in time.  Others can only be had by being with people.

So, how about a travel site that is focused on these experiences instead of just places?

What does an experience look like?  To me, the format for sharing an experience is a narrative and chronological description of a span of time.  Something like:

"I woke up in the early dawn, still acquainting myself with the time change, and bored, I grabbed my camera, hopped a train to Shinjuku station and walked around the neighborhood.  Tokyo is a very different place at 5am.  The bustling crowds are replaced by occasional pairs or threesomes of still drunk stragglers from the izayakis, squinting at the daylight as they stumble to their beds.  An army of somber men in little helmets and orange vests comes out to clean the streets and pick up bags of garbage set out the night before by the businesses and homes.  Most of the shops are closed and their garish displays of baubles shuttered behind steel doors."

This content should be richly linked to locations on a map, business listings, photos, and other related content.

The core use-cases for a minimum viable product would be something like:

  • Contributor posts new experience. 
  • Traveler searches for experiences related to a place, time or person. 
  • Traveler "pins" an experience.

I'd eschew a commenting system in favor of a more simplistic bookmark/like system.  I think that provides the right degree of moderation without distracting from the content.  It may later still be worthwhile to provide a feedback mechanism for readers to interact with contributors, though I envision this as being a private exchange.

This "pin" system could also serve as a way for travelers like myself to collect those experiences that I've already shared with the author.  This may require a second "done that" pin that segregates future vs. past experiences, though I'd want to observe how people use a single "pin" feature before deciding on that.

Advertising is an obvious source of revenue, high-traffic travel content is generally quite valuable, though incorporating it would need to be done with some care lest it cheapen the experience.

It might also be interesting to consider a "pay what you want" or even fixed subscription model with revenue sharing amongst the top contributors.  This would greatly encourage contributors to post high-quality content and would foster a sense of innate value in the community that would lead to a more engaging experience.

To go to market, I'd begin by launching a closed beta, inviting notable travel writers/bloggers to try out the platform.  This would serve to create an initial nucleus of high-quality content and would accelerate the iteration of the design and function of the site towards the easy creation and beautiful presentation of that content.

The rest is left, as they say, to the reader.

Hiring to Create Great Teams

First, go read Joel Spolsky's short book about finding talent, Smart and Gets Things Done, so we're talking the same language.

Done?  Okay, perhaps not, but my takeaway from his book is that it's your responsibility to do anything and everything to find people with general intelligence and who work hard.  

That doesn't, on the surface, sound very complicated.  Our brains are basically hardwired to be able to make these kinds of snap judgments  and if Malcolm Gladwell is to be believed, we should listen to this intuition.  But then, why do the hiring practices of most of the companies I've worked for often fail?

 Photo by Alan Chia

Photo by Alan Chia

I think one reason is the tendency for people to breakdown teams into roles.  They think of their teams as being made up of big squarish building blocks with pretty colors indicating where they belong in some grand scheme.  They jostle them around occasionally, repaint the blocks, write long winded job descriptions about them.  

And it's only natural, building a team is a thicket of interdependent decisions that have to be made promptly and at great risk/cost.  Theoretical physicists call this simplification process:  "idealization".

It's a perfectly reasonable way of solving complex problems.  And in the main, for a large company with a sizable base of employees with diverse talents, role-idealization is a reasonable enough approximation.  They can absorb a less than ideal person because there's a better chance that some arrangement of all the parts will be able to accommodate them (including the arrangement where you hide them in a corner so they stay out of the real team's way).  

But for a small team, one bad hiring decision can be deadly.  There's a reason why people use the euphemism "role-player" to denigrate a person who is useful for some specific task now, but will someday become useless.

A slightly better approximation for thinking about fit would be to think of roles in the same way we think about skills.  Each candidate is going to have some mixture of roles they can play, each with a degree of competency.  Instead of thinking about a person as "a developer", think of them like "a developer who knows how to manage people and run a project".  

Start by making a map of roles that are needed to be successful:  A base of product management, a dash of people management, a hunk of sales, and 2 cups of developer.

Then figure out how the multiple roles of the existing team fits together against that recipe.  Assuming you still have some gaps (and often you don't really, you just think you do because you have money burning a hole in your accountant, or because you're desperate to go faster) you are now ready to hire.

Sourcing multi-dimensional candidates is tough in a world where people search for jobs by role, job boards are all organized by role and recruiters filter resumes using role-related keywords.  You can try to play job description mash-up, "Project Manager/Developer/Marketer", and while this may attract just the right person, you're actually much more likely to just accumulate a blizzard of lower-quality resumes for each of the roles.

So choose a primary role, write the job description to emphasize that you're looking for a flexible candidate rather than list a litany of "responsibilities", and let your recruiter know that you're looking for people with a range of experience.

Once you've winnowed the candidates down, how do you go about interviewing them?

I've always been an advocate for measuring candidates by watching them do the thing you want them to be doing.  For development, this involves asking them to bring in a laptop with an IDE installed.  For product management, this might mean giving them a hypothetical product to build and asking them to create a backlog for it.

As you construct an interview loop, assign a person to each role you wish to test the candidate against.  Multiple separate interviews for any role you're particularly keen to fill.  Include a lunch or cool down interview with a leadership type, but think of it as your opportunity to sell your company to them as opposed to the more typical interview for "team fit".

What if you don't have an [INSERT ROLE HERE] to interview them for [ROLE]?  It might not matter.  Have someone who works closely with that role conduct the interview anyways.  A good developer will know what a great backlog looks like and a good product manager should know what great coding looks like.

After the interview, get all the interviewers in a room and have them secretly cast a yes/no vote for their interview.  Do NOT include the person who did the lunch/cool-down, as this has a high likelihood of being a false-positive/negative.  Briefly review what you were looking for in a candidate in the first place, then have everyone show their votes.  

There are no hard and fast rules on how to consolidate the feedback into a decision.  Sometimes one thumbs down is enough.  Other times the person is such a great find in one role that this trumps their unsuitability for every other role you care about. 

What you're looking for is for the group to come to a consensus on whether or not to hire.  The team should have a working knowledge about the challenges they're facing and you should expect a healthy debate about "what we need" vs. "is this person the right one".  At the end, if you can't reach consensus, then pass on the candidate.  Either you don't really know what you need yet or the candidate isn't really the one you need right now.

The Tyranny of Choice

There is an interesting tension in product design between features/functionality and usability.

On the one hand, users of an application, as they gain expertise, demand sophisticated and nuanced features that allow them to do more varied tasks and create more efficient workflows.

On the other hand, new users to an application are intimidated by large menus and palettes of buttons that deter them from getting basic value from the application.  

More often than not, designers err on the side of features/functionality because they are necessarily experts of their own product and thus subjectively over-value those features that broaden and deepen the experience.

This, as some established product teams eventually learn, can be a recipe for failure as they race ahead of the mass of potential users waiting behind their early adopters.

One interesting way to look at this problem is to consider how, for people, choice can be a bad thing.  

At first blush, this seems very counter-intuitive   

In almost any domain, it always seems better to have more and varied choices.  More styles of clothing, more flavors of ice cream, more ways to get to work in the morning, more colors of paint.  And companies work very hard to give consumers these choices.

And there's no denying there are a lot of good things about choice.  

Novelty is one of the strongest human emotions.  So too is self-identity, and a plethora of choices allows us to construct for ourselves an experience to suit and, sometimes, identify it to others.  The t-shirt is one of the the most elegant vehicles of self-expression ever invented.  Imagine explaining to a Victorian how people would someday display, emblazoned on their chests, their current thoughts about philosophy, culture, and ideas.

And yet, people complain bitterly about the complexity and pace of change that these same choices induce.  We're punished each day by thousands of decisions, some important, some trivial, but many made poorly because of lack of time or energy.

The Rise of the Curator

I signed up recently for Bombfell.  Their service is to deliver you an article of clothing on a set schedule (i.e., monthly) and for a set amount ($69).  You choose some parameters for what you'll receive, like your sizes and preference for long vs. short sleeves, and a personal shopper picks something within those parameters and sends it to you.

I signed up out of interest for their model after reading an article, but after 4 deliveries, I'm quite enamored of them.  

The clothing they choose for me often falls somewhat outside of my standard repertoire, but not embarrassingly so.  As it turns out, this is exactly what I want, though I didn't know it when I signed up.

Another service I started using is Quarterly.  They provide care packages of curated swag, again as a subscription, selected by notable writers, entrepreneurs, organizations or other personalities.  I've yet to receive my first package (from Mark Frauenfelder), but I find myself anticipating it as I would a gift from a friend.

The thread that ties these two services together (and they with this blog post) is that they are fundamentally about taking away choices, rather than creating them.  And they do this while still retaining the novelty and self-expression that come with making good choices for yourself.  

Curation is a bit of a buzzword, even though it's a concept as old as media.  The lasting engagement of broadcast television despite the near-infinite choice available online, is an example of successful curation.  Any story, whether told to friends or written down in a book, is really just a curated set of experiences, arranged to clearly express a larger idea or emotion. 

Both remain compelling, in part, because they liberate their audiences from the tyranny of making endless choices.

When designing a product, it's worthwhile to consider the "cost" of choice in your design.  Walk through your most important use-cases and:

  • Score -1 point for each choice the user is presented with.  And, yes, every widget on that toolbar is another choice.
  • Score -2 points for each time a user is forced to choose between multiple options in order to continue.  
  • Score -5 points for each instance the same choice is presented multiple times without regard to what a user has previously chosen.  
  • Score -10 points for every choice that has serious repercussions if made badly ("Do you want to save that?  Yes/No/Cancel", I'm looking at you..)

On the positive side. consider how your application can make good decisions on your users' behalf.  Use your expertise of the domain and your product to provide a guided workflow that shows the user how to work or play without wasted steps.  Share your deep and nuanced perspective of your content by providing curated spaces where users can passively discover and absorb it.

Done well, good decision making on the behalf of the user, like Bombfell and Quarterly, can be a wonderful product in and of itself.

Birth of a Pessimist

I have a reputation, in my social and professional circles, for being something of a curmudgeon.  

I find this to be roundly unfair. 

Okay, yes, over a pint, I'm more likely to argue with you than agree with you, that's true.  And yes, I tend to be rather critical, and vocal, about things I think could be going better.  I just like to be convinced of a thing before I believe it.  But once I believe a thing, I become its earnest champion, arguing for it and vocally criticising all that...

Okay, perhaps they have a point.

I know the exact moment when I turned.  I was standing at a podium in high-school.  My first debate.


For the uninitiated, formal high-school debate, the kind the National Forensic League gives out certificates of achievement for, is a peculiar institution.  

It's a highly structured speaking format with lots of rules and lots of insular jargon.  It has about the same relationship with a lively argument as chess does with a fist fight.

There is a resolution is chosen at the beginning of each year that forms the major premise for all of the debates that follow.  My year it was (from Wikipedia): "Resolved: That the United States government should reduce worldwide pollution through its trade and/or aid policies."

Evidence of a master debater.  Photo from  Wikipedia

Evidence of a master debater.  Photo from Wikipedia

An Affirmative team posits arguments in favor of the resolution while a Negative team looks to undermine or refute their claims.  Judges decide a winner based on whether enough of the Affirmative team's arguments are left standing after a few rounds of discussion.

The peculiar part is that to win, you don't have to be right.

Instead, the goal was to be the one with the best Evidence.  Each team in a debate brings with them great stacks of index cards with bits of text glued to them.   These make up all the arguments, counter-arguments, counter-counter-arguments, and counter-counter-counter-arguments that you'll need.  The best teams obsess endlessly about Evidence  and you could generally size up an opponent based on the size of the stash they hauled into the room with them.

Back to the Podium

I was on the Negative.  I'd just heard the Affirmative opening arguments, something about how the US should promote nuclear power, and being pre-curmudgeon at that point, I was quite inclined to agree with them.  Their points seemed perfectly valid.  Nuclear power seemed to be an elegant solution to the world energy problem.  While it had/has problems to be addressed, there's no reason why these technical problems couldn't be solved, in time, with better technology.

I suppose I could have just walked off and dropped the class, but I recognized this as a game, and I liked playing games.  I was good at games.  And also being a good student, I had collected many pieces of Evidence to counter this specific argument, so had a chance here and now to win the argument, even if I believed I was wrong.  

So I launched into a rebuttal of each of their arguments, hand waving and pausing for effect while the Affirmative team scurried about trying to find the index cards with the right counter-counter-counter-counter-arguments.

We won that debate.  My partner and I won all the debates that year.  

(This is nothing particularly to brag about.  This was debate class, not debate club.  The bush leagues of debate.  My teacher later lobbied me to join, but I ignored him because it would have interfered with football, which TV had lead me to believe led to girls, and, well...puberty is its own best rebuttal.)

It was at that moment, for something as silly as wanting to win a game, I began to learn how to suppress my emotional and subjective beliefs from the exchange of purely objective ideas.  Or perhaps more properly, to temporarily direct and shape my beliefs towards a contrary viewpoint to allow me to argue it more strongly and convincingly.

Pessimism About Products

As it turns out, this is a wonderful skill to have.  

Very often, we are put in situations where our beliefs are put into conflict with cold hard reality.  The revenue projections that were missed, a heartfelt promise you made to your team but couldn't keep, or a customer looking confused and concerned at your product roadmap.

In these situations, there is a strong temptation to externalize and rationalize what has happened.  The market wasn't ready, the team didn't work hard enough, the customer just doesn't get it.  Its far better if you can be self-critical, take your lumps, and move forward with a newly straightened perspective.  Better still, if you can see ahead of time when your beliefs are leading you over the cliff's edge.

To an outside observer, this can appear to be pessimism.  Particularly if that observer shares the errant belief that should be changed.  

Most people loathe changing what they believe and fear the uncertainty that follows discovering that they are wrong.  They therefore loathe and fear the pessimist, who seems to be tearing away at the fragile veil that lets them act with confidence.

Those people squander confidence.  Yes, it can inspire a team to do remarkable things.  Terrible risks are sometimes only undertaken because of misguided confidence, and great rewards reaped as a result.  But if you deal in it, and it fails the test of time, you're marked a fool.  Being thought of as a fool is far worse than being marked as a pessimist.

Use confidence at the moment of truth, at the end, rather than the beginning.  When there's one last unimaginable leap to cross and you need the team to come with you.

Now, this isn't to argue that I should be forgiven all my trespasses as a curmudgeon.  I'm a creature of emotion as much as reason, just like the next guy.  Sometimes I argue out of bad habit, rather than any particular insight into a situation.  Sometimes I'm the starry-eyed true believer that can't see the imminent danger just in front of me.  

But, if you're not persistently and actively challenging your own assumptions, then you might try a little pessimism yourself.