Recently, a reporter was asking me about founders and failure. Is there anything I’ve noticed about how they handle it well or badly? Are there general trends that unite how founders psychologically treat failures?

My immediate reply was “Founder’s Disease”. Its a term I made up once in a conversation to describe the way that founders have trouble admitting bad news and it is best crystallized in the following example:

A founder I knew well and I were out to drinks with one of his best friends. Because I had a minor stake in the company, I happened to know that it was doing badly and was a month or so away from running out of money. Nevertheless, the founder has a smile on his face and when his best friend asked how the company was doing, he said “Everything’s great!”

Everything was not great. In startups, everything is often not great. And yet almost every founder you meet will tell you about the positive events: traction, press, funding, whatever is most likely to put a positive spin on their company. And that, right there, is Founder’s Disease.

It is totally understandable. Most founders are all-in on a startup and have both their own money (and often friend and family money) and their own reputation tied up completely in its success or failure.  Which makes saying “things are bad” take on the larger meaning of “I am in danger of losing my literal and figurative self-worth”.

And presentation of your startup as successful is also a key component of the business of startups.  Look at Mint, which turned its constant “look at all our users” message into a decent acquisition (5X), conveniently ignoring that only a tiny fraction ever came back again.  Both investment and acquisition depend on defining your metric for success and selling it, hard.

So then why is it a Disease?  Because it leads you to tell your best friend in a bar that everything is wonderful, when your world is crumbling around your ears.  Not only is this incredibly emotionally depleting, because now you’ve literally lied to all the people that would provide commiseration and emotional support, but it doesn’t make good business sense either.

If I’m your friend, and you say “X is not going well”, of course I’m going to think about whether there is anything I can do to help.  And maybe it is just some advice, but maybe it is introducing you to a reporter I know to get you some press traction or an investor who I think can help you with funding.  In trying to self-present as strong, we weaken our position.

UPDATE 2: Apparently, Dan Storms of Originate also sent me Jelly Bellys, but due to a mail miscalculation, I just got them.  Let the weight gain begin!

UPDATE: Julie Fredrickson of playAPI sent me 10lbs of Jelly Bellys!  My dream has been fulfilled.

I recently wrote about a CEO I advise who was having trouble reaching out to others to ask for things, because he felt like he was always taking and never giving.  That post was about the problem and some solutions to it; this post is more generally about how to give back.

The general premise is this: as the CEO, you want to set aside a specific hour sometime during the week to show appreciation for others.  I’m certainly not the most new age guy, so I don’t mean that in the fuzzy, meditative way.  I’m talking about actually doing things for other people and giving them the rewards that they find rewarding.

This hour should be sometime in the evening or morning, so that you aren’t being bothered by incoming email, etc.  And it should be relatively focused on people who have either done something directly for you that week or someone who has done something for you in the long term that you haven’t yet recognized.
And this hour should have a budget.  It depends on how well-funded your startup is, but $100 a week isn’t unreasonable; I guarantee that if done well, this will net your business more than $5K a year.

The seemingly easy part (the appreciation) isn’t as simple as it appears, in part because you want to tailor your rewards to the people themselves.  Some people like public recognition for being awesome on Twitter, others would prefer an endorsement on LinkedIn, others want to get some Jelly Belly’s in the mail (this is clearly my dream).

Think about past people you’ve worked with, family and friends who have been supportive, anyone who has ever done you a favor (and if you’re doing your job properly, you should have plenty of those).  Think about everything you know about them and what would make them feel happy, honored, and remembered.  It doesn’t have to be time consuming or expensive, and you can probably get through at least 6 in an hour.

I’ll close with one of my favorites: cowboy boots and Dave Clarke.  Dave is a hell of a guy; he was our first hire at Churnless, where we literally just sent him an @Churnless.com email address and said that he worked for us now.  He came onboard without having a clue what we were up to and who could possibly ask for more than that?  He does great work at the practice he founded (AuthenticMatters) and remains one of my favorite people in the world.

Now Dave lives in Philly, so he used to come up to the Churnless office every two weeks or so to work.  Slept on the couch, put in two good days, went home.  So one night, while he was out to a meeting, I stuck a pair of cowboy boots with a note expressing our gratitude for his badassery on the couch before I left.

It isn’t just leaving the gift that matters.  I wear cowboy boots every day, and Dave is a guy with a rustic edge (he’s from Virginia, listens to a lot of Drive By Truckers, and accepted a hatchet from me for his wedding present); giving him cowboy boots was a way of communicating how we felt.

And he felt good about them.  Still wears them when I see him.  And moreover, the next time I asked people in the office if they needed supplies, our lead engineer said “No supplies, but I want cowboy boots.”  Which he got, when he completed his first major product launch with us.

There is no substitute for appreciating people.  Set aside the time and budget and get it done.

The short lesson here is: don’t keep in features just because they were hard to build.  Good and bad are not the same as hard and easy, and even if worthwhile things were always hard (which they aren’t), that doesn’t mean that all hard things are worthwhile.

The longer explanation starts with the documentary a friend shot.  When I was watching the rough cut, I was marveling at how varied the footage was: some extremely high quality and quite moving, others less so.  My favorite was a city council meeting with the world’s worst audio; periodically, a door chime would come on while people were talking that made it sound like it was filmed in a 7-11.

Yet it made it into the final cut.  And as I was talking to my friend, I began to understand why.  Getting into the city counsel meeting, and filming it, was a tremendous endeavor that involved plenty of red tape and logistical challenges.  And because it was so hard, she was experiencing cognitive dissonance: it must be valuable because why else would I have put so much work into getting it?

I’ve seen people do this product development meetings over and over again.  Either a feature was hard to imagine or hard to execute on, and so when all those resources had been put it, it was immediately imbued with tons of value.  Acquisitions are a classic case: we paid so much for this, it must be really strategic and core.

Mistakes happen.  Sometimes we built parts of our product that just don’t belong, either because of poor fit or poor execution or just plain bad roots.  By leaving them in, we compound the mistake: it is like watching idiots in survivor movies.  You want to tell them to hurry up and build a shelter already, or get some food, but instead they just keep spending a bunch of time building showers.

Don’t let your mind win.  If a feature is bad, cut it.  This also goes for team members, marketing campaigns, and bizdev deals.  The biggest mistake you can make is holding on to bad ideas.

This post has a backstory.  When I was considering colleges, I was living in Hong Kong and it was really between two great schools: Lewis and Clark (which offered me a full-ride along with a stipend) and Swarthmore (which offered me some aid, but not really very much).  Lewis and Clark, in their extreme interest, also managed to track down an alumnist in Hong Kong (whose name I have long-since lost, which is a shame, since I owe him a great deal).

I told him about my options and he was prompt in his reply: “Are you kidding?  Go to Swarthmore.”  Probably not the pitch Lewis and Clark was hoping he’d make.

“It is simple.  Money is just money.  Life goes in stages: first you learn, then you earn, then you serve.  Go to Swat, no matter what it costs, then earn good money until you’re 45, are debt-free, and have money saved up, then go serve the ideals you really care about.”

There is plenty to dispute about that advice: the value of a particular college over another, how hard it is to leave a job that pays you well at 45, how easy it is to serve when your knees are going and you really like comfy beds.  But there is a core of simple truth there: that you don’t have to do everything at once and that you can have ideals without having them be the primary force behind all decisions.  Indeed, any notion of “balance” suggests that different forces have to guide you at different times and that single-minded pursuit of anything just makes you sick and tired and too poor to have the effect you want to have.

The reason this comes up tonight is a conversation with a friend who is choosing between a job that will likely result in about $5m in two years (as a company exits) as compared to a job that gives him the chance to have paradigm-shifting power and pay relatively well (just not $5m well).  As we talked, it became clear that he really wanted to take the $5m job, but hated having to admit to himself that money matters.

But money does matter.  I’m not suggesting it is easy to remember all your lofty goals  after you have a $5m check in your pocket; on the contrary, I think it is damn hard.  But I think it can be done.

GetRaised.com got built because we had enough money to do it.  If we had more money, it would be even better.  And it is just that simple: all the millions of extra dollars that we’ve helped women earn, all the narrowing of the gender wage gap, would not have been possible if we hadn’t made enough money to see us through the creation of the product.  GetRaise is a pretty strong argument for why sometimes, taking the money is not only not bad, its actually good.

I’m convinced that a marketer could learn everything they need to know about their brand just by walking through NYC neighborhoods and listening to peoples’ conversations.  For example, today I heard someone tell someone not to get the iPhone 5 because “the maps suck” and that’s most of what they use their phone for.
I also heard a woman tell another woman that she had to register to vote because it was important.  It was a good day in NYC.

A friend pointed out this quote from a Vanity Fair profile of Obama.

This time he covered a lot more ground and was willing to talk about the mundane details of presidential existence. “You have to exercise,” he said, for instance. “Or at some point you’ll just break down.” You also need to remove from your life the day-to-day problems that absorb most people for meaningful parts of their day. “You’ll see I wear only gray or blue suits,” he said. “I’m trying to pare down decisions. I don’t want to make decisions about what I’m eating or wearing. Because I have too many other decisions to make.” He mentioned research that shows the simple act of making decisions degrades one’s ability to make further decisions. It’s why shopping is so exhausting. “You need to focus your decision-making energy. You need to routinize yourself. You can’t be going through the day distracted by trivia.”

It is hard not to love it when the President of the United States makes your case for you.  I haven’t gone so far as to wear the same clothes every day, but I have done some careful buying so that any two random items from my closet will match each other.  And that, I think is the next step in choice reduction and my main reaction to its critics: it isn’t about not choosing, it is about choosing when to not choose.

I think it is good to have expressions of your personality and selfness in your life.  Johnny Cash went with all black, I picked cowboy boots, and I’m sure one day I’ll raise kids with some equally odd way of going about it.  But even though I sometimes want to wear something distinctive, I’ve setup my life so that I don’t have to if I don’t want to.

Take, for example, the incredibly burdensome decision of “what to eat for dinner”.  Yes yes, first world problems, but a real one none the less; when I was a kid, my mother never minded cooking dinner nearly as much as she did trying to figure out what to cook (resulting in her trying to force my brother and I to plan the menu, which we were smart enough to avoid).  I hate trying to choose what to have when I get home now, which is why I have a default: the Matt Wallaert Salad.  Entire bag of lettuce, peanuts, cheese, fat free honey mustard dressing.  Instant dinner, and I make sure to always have the components in my fridge.

I also have the New York lifestyle down: a standard rotation of four resturants that I know are good, where I can always order the same thing, and I can go to any of them randomly when I feel like outsourcing food choice.  Sure, in some sense, I’m “choosing” but not in the active, cognitive-resource depleting way the President is pointing out.  And when I really care about what I’m eating, when I want to make that choice, I can.

Setting up defaults doesn’t mean you always have to go with them, just that they are there when we need them, and I think that is something we often forget.  Which may be the start of a followup post…

(Thanks to Sarah Duve for pointing out the original article.)

Update: Apparently, Zuck does the same thing.

Here’s the premise: if you’ve set your analytics up properly, it means you know which metrics mean success.  And knowing what success is means that you’ve chosen the goal of your product ahead of time (which, by the way, is a really damn good idea).  And if you can measure success, you know when your product goes from “not working” to “working”.

That’s test-driven design.  Engineers use it all the time, and I’d like to suggest that product people should too.

Engineers face a number of issues with TDD: it takes a bunch of time to write tests in advance, it requires a lot of upfront discipline before you even start coding, and it restricts agility (because you may end up scrapping a bunch of tests as scope changes).  It works well if you can get everyone on board, but it can be murder trying to get there.

Fortunately, these are mostly a non-issue for product because the whole point is that doing this in advance enables agility in meeting the goal.  That is, while engineers are writing many tests for many problems with only one solution, product people are writing a test that they can solve a variety of ways.  So here’s the drill:

1) Decide what is the single most important thing you care about your users doing. For example, sitting down with Estimize recently, the goal that came out of conversation was getting as many estimates from qualified professionals as possible.  Note “qualified professionals” – be careful about tossing out overly simplistic goals like just “user signups”, or you’ll end up like Mint, with plenty of registered users and no active ones.  Be specific in your goal, like “people who register and are continuing to log in at least once a month for three months”.

2) Decide how to measure that behavior. For RentHackr, where the goal is as many leases as possible, it is fairly simple: number of leases with valid data.  That means writing a quick script that counts the leases and then eliminates invalid ones (rents that are bogus, which is pretty easy to tell by looking at market rates in an area).  This measurement step is critical but should be fairly easy if you wrote a specific goal, as mentioned above.  If you didn’t, and you find yourself including a lot of junk data, you need to go back to Step 1.

3) Iterate, test, repeat. Once you’ve got a test in place, you can start building features against it.  Put out a feature, let it run long enough to get a reasonable sample, and see if you actually increased the metric you were trying to increase.  Debug.  Repeat.  This will keep you from releasing features just because your CEO “thinks that would be cool” and instead forces you to release features focused only on what your product is actually supposed to be doing (once again, product viewpoint for the win).

(Thanks to the DataGotham conference for triggering this line of thought.)

My most recent post got made into a Someecard, so I’m feeling pretty good.  Sure, its not something that my parents would understand (being made into a joke on a site that 800K people visit religiously) but it is still a high moment.  I was also on FoxNews, trying to help more women get raises.  Again, not everyone’s idea of having made it in the world, but something that I walked away from with a light step and the urge to crow.

Both of those two moments made me feel successful: good, accomplished, like I had achieved something.  And yet only one of them is also about progress: having actually changed the world for the better in a tangible way.

You could take a flying leap and suggest that if I died tomorrow, my Matt-inspired-Someecard still would have made a few people laugh and that is valuable (because the stick really is that far up my ass and I graduated from Swarthmore, I would be likely to kill a discussion by debating that).  But in reality, the Someecard is really just about me feeling personally validated; it doesn’t really do much for anyone else.  GetRaised, on the other hand, has helped thousands of women earn millions in raises, a feat that few others can say they’ve accomplished and with an undeniable positive impact on society.

What is interesting is how often success and progress don’t full overlap and how rarely we consciously make sure that we’re getting a balance of both.  People love to endlessly complain to me about their lack of work-life balance, but I think what many of them actually may be complaining about is their lack of success-progress balance.

For example, GetRaised wasn’t all that much fun to create.  It was built on the side, outside of our direct line of business, so that it meant it had to be cobbled together in between other projects.  The problem itself wasn’t particularly intellectually challenging, we didn’t get to use any whizbang technology or pyrotechnic tricks, and it is abundantly clear how much better it could be (I still have a wishlist a mile long).  And yet it was still a project worth doing: it made real progress, every day, and even if the high moments of launch and press and helping women aren’t constant, there are enough moments of success to make it maintain a healthy and rosy glow.
And that is what is missing for so many progress-driven projects: there is not nearly enough celebration.  I’m reminded of a quote From Dusk Till Dawn.

Are you such a loser you can’t tell when you’ve won? The entire state of Texas, along with the F.B.I., is looking for you. Did they find you? No. They couldn’t. You’ve won, Seth, enjoy it.

Too often, when working on something that truly matters, work really does feel like work.  The aching, grinding pressure that is doing the 100th wireframe to try to get a particular product point right is not fun, no matter what anyone tells you.  If we don’t look for moments of success, ways to feel good and accomplished, then we will quit long before we finish anything worthwhile.

Equally dangerous (or, given our current culture, perhaps more dangerous) is the feeling of success that comes without any progress at all.  The problem with attention from Someecards is that it can be addictive: it makes you want to get attention, to simply feel good, while removing any responsibility for actually doing anything worthwhile.  Success without progress is the flip side of the coin and it is the ugly underbelly of a lot of American culture right now.

There are plenty of Paris Hilton-like examples but those are too easy.  Even the business and political worlds have plenty of successes without progress.  You know them, people who are constantly telling you how important they are but you can’t figure out a damn thing they’ve done.  Sure, they’re great at promoting themselves within a community and may even feel genuinely good about their success (although most psychologists would suggest they don’t), but when they look back on their accomplishments, they’re still docked on shore while others are quietly sailing away.

We need enough success only to keep us making progress.  But we still need it.  And it is something worth looking around for in people.  Who do you need to congratulate on their progress?  Who do you need to offer a chance to make some?

The lovely and talented Meghan Casserly recently wrote a piece entitled “If Time Is Money, Millennials Are Broke–And They Couldn’t Be Happier“.  The piece is great, but the title is a bit misleading – I’d argue that she does a fairly good job of talking about all the reasons that the millennial race to be “busy” is actually eroding a lot of their satisfaction in life.

At Swarthmore, where people love to brag about how tough the school is (hence the unofficial slogan “Anywhere else, it would have been an A”), what Casserly described was known as “misery poker”, presumably because people were constantly upping the ante.  You’ve got a five page paper to do?  Well I’ve got a ten page paper and an oral.  You get the idea.

My argument is not that young people aren’t playing the “busy” card, but that they are…and it is making them unhappy.  Misery poker is a form of negative busyness: I’m so busy, isn’t it terrible (but not really terrible, because it says I’m productive/smart/etc.)  As Casserly’s experts point out, there are positive versions, like “being busy makes us feel valuable”, but the underlying current is the ways in which busyness is actually an inauthentic remedy for larger troubles, which ultimately only leads to greater dissatisfaction.

For example, if busy = valuable, then more busy = more valuable.  And since the hedonic treadmill means that we will always acclimate to our current level of happiness, that means that in order to stay happy, we will always need to be…wait for it…more busy!  Ditto for suggestions her experts make about feeling needed, self-presentation for social credibility, and other potential theories: the crux of the argument is always that busy replaces actually being needed/popular/etc.  Busy becomes the incredibly poor coping mechanism for not actually accomplishing fulfillment of those needs.

To put it a different way, the perpetually-wise Avi Karnani once pointed out to me that many people confuse motion with progress.  He has some great hand gestures, which you’ll have to imagine, but motion is lateral movement that looks like you’re doing something but isn’t going anywhere, whereas progress is actually moving forward.  Busy may make us feel valuable/needed/popular, but because it doesn’t actually push us forward, the moment we stop moving, we are immediately unhappy because we can look back at the shore and realize that nothing has changed.

The irony is that all this motion of being “busy” is actually doubly costly: not only is the busyness not leading to genuine progress and happiness, but it holds us back from taking advantage of opportunities that would.  In college, it was the equivalent of not going to a party so you could “work on a paper” and ending up just watching TV; in life, it is saying “you are too busy” and then ending up sitting home on a Friday night.  Or worse, not staying home and instead going to a birthday party just to “put in an appearance” and have no genuine interactions of any kind.

In the end, it all comes back to authenticity.  There is such a thing as being truly busy, and it probably does make people fairly happy, provided they are busy with things that they actually want to be doing.  But that’s not what Casserly and I are talking about.  What young people are doing today doesn’t have to do with being truly busy, it has to do with the appearance of busy for busy’s sake.  And as The Shawshank Redemption points out, you can get busy living or get busy dying…busy for busy’s sake is almost certainly the latter.

Chris Dixon recently wrote (in an incredibly brief post) that recommendation systems are features, not products, and pointed out that Hunch was only compelling after being bought by eBay, where it successfully powers both recommendations and discovery on the site (not 100% sure on this).  I agree with Chris and have a few notes.

1) Recommendation takes initial desire and channels it: you want a TV but you’re not sure what is the right kind, it tells you the right kind and thus makes it easier (lowered inhibiting pressure).  Discovery creates desire (higher promoting pressure): you weren’t thinking about food, but you are now.  People tend to mix the two up.

2) The reason that recommendations don’t stand on their own is because the intended action is to satisfy a desire.  If you are looking to buy a TV, the end state is the purchase and telling you which one to get doesn’t end the needstate.  So you’ll get outcompeted by anyone that does (like Amazon).  The only place where you can have just a recommendation engine is where you can’t complete the needstate in that medium: I can recommend recipes, for example, because there is nothing more than can be done online.    But these are dangerous plays, because you can get outcompeted by anyone who brings it closer to closing the needstate. Recommendations worked until Amazon made it so you could get recommended and complete the transaction in one place (just ask CNET).

3) Discovery, in contrast, can work on its own.  Not just because of SEO (Chris’ explanation), but because true discovery isn’t the same as a recommendation: it actually creates desire, often from adjacent desires.  Take Pandora.  Nobody puts on Pandora to purchase new music – that isn’t the point.  But in the course of satisfying one desire (good background music), it occasionally creates another (the urge to buy a song).  If you are browsing blogs about fashion for entertainment, sometimes you find things that you then want independently of your previous desire: buying something doesn’t make you want to stop reading fashion blogs for entertainment  That is generally a clue that discovery happened, when you do something but it doesn’t diminish the need that you came for in the first place.

Bonus: discovery and recommendation map to the two ways I break advertising down for people often as well.  Some ads are about creating a desire for a thing you didn’t previously want, often by coupling them with other things you want (like selling beer with naked women).  You didn’t want a beer, you did want a naked woman, now you do go get a beer, though it doesn’t quench your thirst for a naked woman (studies suggest it may even enhance it).  Other ads, in contrast, are about taking existing desires and channeling them.  You were already thinking about buying a car, you should buy our car, because it is the best car.  It fits your need.  Buy it and you will no longer need to buy a car.