Win, Play and Lose

No matter what product you are building, you can’t be the best at everything.  Spread your resources across all areas equally and you will be average at them all.

So how do you figure out where to focus?

One technique we used at Shop It To Me was called “Win, Play and Lose”.  We divided up all the product attributes we could think of for a product into 3 buckets.

“Win Bucket”: The “Win Bucket” contained the few attributes we thought defined our brand or were most critical to solving a crucial problem (such as accurately showing prices or providing a truly personalized experience).  These were core to our offering and were the key way we separated ourselves from the pack.  They were also what we felt the customer needed from us most.

“Play Bucket”: Many of the attributes we would categorize into the “play bucket”.    These attributes are table stakes — we need to have them to be in the game, but we didn’t need to excel with them.  An example here is web page aesthetics.  Aesthetics are definitely important for an eCommerce fashion company.  When buying fashion, people are not just purchasing clothing: they are buying an image of who they want to be.  But we believed winning on aesthetics alone was not going to win the space.  Instead, it was more of a threshold.  If the store had an aesthetic above a certain level, people would feel comfortable to buy.  If not, they wouldn’t.  The most beautiful site might increase sales on the margin, but after a certain amount we believed there were other attributes more likely to move the needle.  So we set a goal for our aesthetics to be competitive but not to outright win in the space.

“Lose Bucket”:  For at least one third of the attributes we would concede and “lose”, consciously deciding to build a version that was less than average in the market.  These were  not easy decisions.  Many of these attributes we chose to “lose” at are the strengths of our competitors and touted on feature lists.  But excelling at these features would not help us as they were not the main reason people were using our service.    By not focusing on these areas, we instead could double-down on the few attributes where we really needed to “win.”   We specifically used the word “Lose”.  By consciously deciding to “Lose” in an area, we made it clear to the team that it was ok to have a sub-par experience in areas that were not critical to our company’s success.

By dividing the attributes of your product into Win, Play and Lose, you can focus your efforts on what matters — the few most important features or products that help solve your most critical problems and lead to success.



  • No startup can build a product from the beginning that is great at everything. The best new products were great at some things and not so good at others.
  • Rather than trying to be great at everything, consciously choose the few areas where you wish to be great (you want to “win”), the areas where you just need to be competitive (where you want to “play”) and the areas where you are willing to be substandard (where you explicitly decide to “lose”).
  • By dividing your product attributes into these three buckets, you can focus your resources on just the most critical issues to your product’s success.

Shop It To Me In Forbes and Hacker News

Two fun news pieces for Shop It To Me today!

1) Forbes just posted a great Q&A about myself and Shop It To Me as part of their designer spotlight series.  Check it out!

2) We just announced in our blog that we recently removed passwords completely from our Shop It To Me iOS app .   We’re really proud of this accomplishment as our app members no longer need to create and remember a unique password when they sign up or log in and we hope other app developers will follow suit.    Currently it’s gaining attention as the post is a top-10 listing on Hacker News.

Let us know what you think and Happy Thursday!



It’s Time To Get Emotional

At Shop It To Me we are customer-driven so we think about product a lot. We’ve noticed that too many Internet companies today think about their product almost exclusively in terms of a functional experience. What need are we serving? What solution do we provide?  What features should we add?  Recent books and blogs encourage that by having you ask questions like “what problem are you trying to solve?”, “what is the pain point you are addressing”?

Those questions are certainly important to answer, but if you want to build a deep connection with your users or customers, you will also need to answer a much more important question: What emotion should customers be feeling when using your service?

Successful consumer products are often valued more for the emotion they generate than the tangible value they provide.  If you look at almost all successful marketing campaigns, you’ll see the deep emotion behind it.  CPG companies are particularly amazing at figuring this out.

Some examples:

  • Michelin Tires are not just tires to help your car move.  They embody safety, security, protection. Michelin ads are all about safety — they have either a huge puffy mascot (who looks like an airbag), or a baby riding inside the tires.  With these tires, you not only have wheels to move your car, you can feel rest-assured your kids and the things you care deeply about will be safe.
  • CocaCola is not just carbonated sugar. It’s bottled up happiness.  Their ads (Happiness Machine, Sleepwaking) all show happiness in unlikely circumstances, and their tagline “Open Happiness” is a pretty obvious connection on how they want you to feel when you open a bottle. .

Having a strong emotional connection is not just for physical consumer products.  It is important for any online service or product as it can have a major impact on who uses the product, when they use it, what you can charge and your overall product’s success.

Take two recent mobile-based taxi-alternatives:  Lyft & Uber.  Both are trying to solve the same problem:  I need to get somewhere now and there is no taxi available.  But both are building different relationships with their users by touching upon very different emotions.

Uber’s messaging and service is built to make you feel pampered, like a high-powered executive.  They primarily use black cars or nice hybrid SUVs to pick you up.  Their site is in classic silver and black with a luxury car featured.  Their tagline “everyone’s private driver” —  reinforces the emotion.   With Uber, you are like the guy in the back of the limo passing the bottle of Grey Poupon.


Lyft is taking almost the opposite end of the spectrum.  They are focusing on being your pal.  Instead of black cars, they solicit regular people to be their drivers.   All of their cars identify themselves with quirky pink mustaches.   Their domain name is a quirky as opposed to a more standard   They encourage you to sit in the front seat and fist-pump the driver when you enter and exit.   Lyft is less like having a private driver, and more like having a friend who today is your designated driver.

 Screen Shot 2013-06-25 at 9.03.53 AM

Based on the marketing alone, one would expect very different experiences with the two services. Want a professional, polite, quiet driver?  Use Uber.  Want a friendly conversation and a quirky fun, low-key experience?  Choose Lyft.

If your business is in a crowded marketplace, creating a strong emotion can be a huge differentiator.    Bottled water is pretty commoditized, and yet companies like VOSS can thrive by creating a product more than 2x the price of the rest of the market (and therefore generate many more profits) because they aren’t just delivering water, they are delivering on the feelings of luxury, stylishness and exclusivity.

At Shop It To Me, we are constantly looking at not just what we do (giving you updates on what you want) but what emotions we want you to feel (smart, in-the-know, excited, accomplished).  Because while the service may help fill a need, it is the emotions that users will remember.

So next time you are thinking about your value proposition or what need you are serving, don’t just stop at the services and features.  Take the time and think about the key emotions you want your users to feel when you successfully fulfill their needs and you’ll end up building a much longer-lasting relationship.


Building An Indispensable Product

At Shop It To Me, we believe a key way companies disrupt a market and have long term loyalty is by building not just a great product or a insanely fun product, but an indispensable product.

Look at some of the services today with the most avid users — Google Search,  Apple’s iPhone (when it first came out), Twitter, Etsy, eBay, Pinterest — all have one thing in common:  They all have built a product that for some audience is indispensable.

What is indispensable?

So, what exactly is an indispensable product?  I believe you can divide it into three different components:

1) An indispensable product solves an important or meaningful problem.  

Every indispensable product out there solves important problems for its users. VCs often refer to this as as the “aspirin” vs “vitamin” scenario (whenever you have a headache or pain, aspirin is a must-have;  vitamins are a nice-to-have).

There’s a reason Google Search is so popular —   It is indispensable in two ways.  Users of Google search trust it to give them answers to the most important questions.  For advertisers, Google SEM and SEO has traditionally been the best place to find customers with active intent to buy their service.    Selling your amazing new tax software for businesses? Get to be at the top of the search results for “business tax software” and you’ll have the huge number of highly targeted leads you need to crush your quarterly goals.

2) An indispensable product has no good substitutes.

To gain real traction, an indispensable product not only needs to solve an important need; it must lack good substitutes when it first comes out.  You can’t have your product be indispensable if users can easily find an alternative.

When the Apple iPhone first came out, there were no other products remotely like it.  It was terrible as an actual phone, but it was the only phone out there for consumers that would let you actually search and view real web pages (as opposed to just mobile versions), or see your emails in a visually appealing and simple way.

If you want to build an indispensable product, you need to make your product unique for the customers you are going after — you can’t just be a slightly better version of a popular product and expect people to switch.

3) An indispensable product is ideally something you need on a frequent basis.

The third point is not a true requirement of indispensability, but an important attribute if you want to build a habit and get frequent usage.   If people find your product indispensable but only need it once every 5 years (or once at all), you may have a great product, but you won’t be building a habit for when competitors enter the space.   On the other hand, if people need your product frequently, you’ve got the ability to train them to be accustomed to your service which will keep users coming back long after other competitors make similar products.  (Think of the millions of people still using MyYahoo! 10 years later)

A quick test for indispensability

So you think your product has all three of the criteria for an indispensable product; how do you know for sure it’s indispensable?  Here’s one easy test: take it away from your users and see how they react. If people start screaming that the service you provide is gone, there’s a pretty decent chance you have an indispensable product.

Think about the products that are indispensable to you.   Smartphones, webmail, Twitter  are all indispensable to certain people.  (Think of how people tense up when their phone goes missing for 15 minutes, or how a reporter would feel if they could not access the Twitter feed and had to wait until news appeared on a website).

We know our Shop It To Me emails can be indispensable from inadvertent tests.  Every once in a while our emails get delayed and when that happens, we often know about it not only from our data but from our support box —  users email us demanding (occasionally with profanity) why their salemail had not yet arrived .   And with our new product,  Shop It To Me Threads, we occasionally test the waters of indispensability by asking user-testers how they would feel if we removed certain features.    We’ve had a number of features that users say are “really great” that we removed from our system because they didn’t notice when it was gone.

So for all of you working on the next big thing:  As you build out your product, and start prioritizing features — figure out what parts are need to make your product more indispensable and focus your energies on that.  You’ll build a stronger product and have a much larger chance of turning your idea into a wild success.


Technical Debt — when to deal with it?

One of the key themes In the upcoming presidential election is what should we do with the US fiscal debt. Some argue we should stop everything to pay it down right now; others think we should put our resources into improving the economy and then pay it down later when we have more resources (i.e. more GDP).

Technology companies face the same dilemma on a micro-level every day in terms of what is commonly called “technical debt”.  When developers write code for a product, they are inevitably writing in assumptions as to which things they will be developing more thoroughly and which they won’t.  For example, a developer initially coding an iPad app to track weight loss would likely put in extra code to record and share your weights on an iPad and not nearly as much code to record morning heart rates or sleep patterns or to record weight on another device like an Android device or a website.

The challenge is that your initial assumptions when you code often end up being completely wrong.   What you thought was definitely on the roadmap last week, might fall off completely after talking to more users, hearing about a competitor, etc… Likewise, the thing you thought was a tiny feature two weeks ago when you started building it now is considered the core of a huge new platform.

The result is Technical Debt — you end up with oodles of code that are being used for purposes for which it was not initially intended.  The code is sub-optimized so you end up taking much longer to build things, usually with more lines of code and more bugs.  The longer you wait, the more the TD will cost you valuable time and resources.  But fixing it means stopping new features, and spending time rebuilding functionality that already works.  It just  feels like you are wasting time that could be spent adding new functionality.

Every development product I have ever been involved with has at least some levels of technical debt.  So what do you do?  When do you pay it down and when do you ignore it?

One engineering philosophy wants to err on fixing all bad code.  As soon as you see any poorly written code, stop what you are doing and go in and find a more elegant solution.

At the other end are the people who don’t want to fix the code until it actually breaks and then go in and only clean the part that is broken.

I am somewhere in the middle.  While it is great to have super-elegant code everywhere you look, I think it ends up being a waste of time as you’ll be over-optimizing.  Sometimes, once the code works you never need to change it, so spending hours refactoring it to make it elegant decreases overall efficiency.  At the same time, waiting for the code to break and only fixing the part that needs fixing ends up penny-wise pound foolish.  You are spending all your time and money repeatedly repairing an old clunker when it would have been cheaper and faster to just get a new car.

So here’s my philosophy.  When considering technical debt, I think about 3 things and make my decision based on them.

1)   How will cleaning up the bad code affect the next few sprints in your roadmap?   Fixing something now that won’t really help make your next few sprints faster is probably not worth your time.  On the other hand, if fixing technical debt will speed up development of functionality you need to build soon, you may be able to get it in for free.

2)   What is the frequency of profanities —   How often are you cursing the poor code quality?  If the curse index is high, it probably will help both productivity and morale to fix it.  On the flipside If you don’t hear people complaining about it a lot, it probably is not a huge pain point.

3) How firm is your deadline?  Everyone has deadlines, but if your next deadline is an absolute MUST-make  (i.e. you are showing it to your largest customer’s CEO on date XX), you may want to just delay the technical debt until missing your deadline is not quite as costly.

So how do you handle technical debt?

Smart Tips for better customer feedback

My latest post, 6 Smart Tips for Better Customer feedback, is now on the website!

Three of the tips are:

1. Keep customer support in-house and staffed by smart people.

2. Initiate customer conversations yourself.

3. Test constantly.

To read more about them, check out the article.


What our customers say vs what they mean

My latest article on what customers say vs what they mean  and what you should do about itwas just posted at!

Here’s a snippet…

You know this meme: You hear one thing, but it probably means something else entirely. (Like when my wife says “Don’t worry about it,” it usually means, “It’s important. Worry.”) You’ve probably seen these sorts of lists for relationships,Americans, or maybe venture capitalists.

But funny as the jokes can be, the kidding stops when it comes to your customers–because knowing what they really want is critical to your business.

We’ve interviewed hundreds of users of our service and we found some common discrepancies between what they say and what they actually mean. Here are eight common comments, translated for you–plus some advice on what you should and shouldn’t do about it.

‘Your website should be more like [your competitor’s].’

  • What they mean: “I really like [your competitor] and think your site is pretty close to theirs, but I really prefer Site X.”
  • Don’t: Just make your site more like Site X.
  • Do: Figure out what makes you different, and change your site to reflect that. You want your site to be so different from your competitor’s that there really is no comparison.

To see the whole list, go to the article at

How to build a culture of experimentation

As you have probably noticed from my blog — at Shop It To Me, we are big fans of experimentation.   I believe to succeed you can’t just treat experimentation with lip-service.  It needs to be ingrained in your culture.

For those of you who want to start experimenting in your company, I just posted an article on  How To Build a Company Culture of Experimentation at Mashable.  Take a look!


Loyalty for Shopping Sites

At Shop It To Me, we interview people all of the time about their shopping habits, and with the exception of maybe Amazon, there currently really is no one major player among pure shopping search sites.

When someone wants to search for an item or shop for an item, they either shop a number of individual retailers or go to google and do a search.    Yes, shopping aggregator sites like Nextag, Shopzilla and get millions of users coming to their site, but for the most part their traffic is derived from some variant of Google search results.   Google “black trousers” and I promise you’ll see at least one of theses sites in your search results.  They’re awesome at figuring out how to be the top result.   But the relationship is really between the user, Google and the end retailer.   If Google one day swaps one of these aggregators for another the user doesn’t care, let alone notice.

And while ‘Loyalty’ and “Cash Rebate” sites have people coming directly, the customer’s loyalty is to the rebate — not the actual site.  That customer may come now,  but they’ll also be the first to leave when a retailer or another competitor has a better rebate or discount.

Shopping queries account for a substantial percentage of all searches, and while we have solutions for “searches for people” (LinkedIn/Facebook), Travel (Kayak),  Restaurants (Yelp) and general information (Google) we have no great solution for products.

I believe there is a huge opportunity to build a shopping experience (site, mobile, email) with real loyalty.  A site that people will actually access directly as opposed to via the search engine and will give customers real value.

To do this, I believe we need to rethink how shopping sites work altogether.  The site that gains people’s long term loyalty will be the one that optimizes the relationship as opposed to just optimizing the transaction.  It will be the place you go because it gets you;  it knows what you want, what you like, what you crave.  It will be the place that looks out for your best interest.  Going anywhere else would be a waste of your time and money.

At Shop It To Me, we’re building a next generation platform that I believe can one day realize that vision.  We’re not there yet, but we’re on our way and I’m really excited about the progress we have made so far!

And if you want to help us make this a reality, join us!

First Impressions

At Shop It To Me, we are constantly experimenting.  It’s one of our core values.  In fact, as of this morning, we have 24 different A/B experiments running on different parts of our site.    Each week we probably add anywhere from 1-5 new experiments to our testing pool (and take out 1-5 old ones).  We experiment not only with small features but big ones too.  At any given time have 1-2 completely new products that we are testing with a subset of our users.

But unlike a lot of companies who announce any new feature or product, we don’t announce even our biggest products when we first put them into the wild.   Even though we have press asking for new things and we could get a great “usage spike”  we actually tell our PR team not to talk about them until the time is right.

The problem is, until you have nailed the product, a press “spike” is just a spike.

Now don’t get me wrong, I’m not a big fan of the “stealth company” technique — companies that promote that they are doing something amazing but won’t tell you what they are doing.  I think these companies actually set such high expectations it is really hard for the user to beat them.

But I am a fan of not announcing a new product until we are pretty sure it is a hit.  Why?  I am a big believer in the disproportionate power of first impressions.  Humans are hard-wired as a species to take a tiny bit of data and extrapolate big decisions/impressions from it.    It’s leftover from when our ancestors had to quickly decide if a creature is predator or prey, and it is still in almost all of our decision making.

We make significant long-term, big decisions based on only on a first impression all the time.  Have a terrible first date and there’s a pretty high chance you will give up before going on a second one (even though even your “soul mate” and you are likely going to have bad days together).  Try out a new restaurant and have a bad service experience and you likely won’t ever return — even if they later get great service reviews.   And in business, start off a presentation poorly and much of your audience likely stopped listening  (and will rate it poorly) even if remaining 80% is amazing.

Remember that before spending loads of money announcing your next product. If someone tries your product and just likes it (or thinks it is mediocre), you have likely given them the permanent impression that your product is just OK.  They won’t return.  On the other hand, get a user to have an “I LOVE THIS!” first impression, they often will still have positive impression years later.  We’ve seen this time and again —  our best users are the ones who found something they wanted to buy in their first emails.

So before we turn on the PR machine for a new release and send it to all of our users, we make sure that almost anyone who sees the product is going to have a great first impression — such a good impression that they want to keep using it (and hopefully tell their friends).   How?  We spend months usability testing the heck out of it —  constantly tweaking it with user-testers and thousands of random users and friends and family-members and even random people we recruit off the street (yes we’ve done that).  And we learn from them and make the changes that gets their reactions from “Meh” to “Like” to “Love” (a subject of a future post).

So while we may lose some “brand-awareness” and short term traffic from multiple product releases, we more than make up for it by having a product that for most people feels “pretty awesome” right from the start.