In psychology, we talk often about the survivorship bias: the tendency of people to focus on winners, rather than losers, as a way of trying to insure future wins.  The prototypical example is airplanes in war (one used in a great recent post on the topic): if you want to figure out how to keep planes from getting shot down, don’t look at where the holes are, look at where the holes aren’t (because you can presume that the planes with holes in those places didn’t make it back alive).

But there is actually a larger trend here than just losses and wins.  In my traditional style, I’ll call it a true two-by-two matrix: expectation given resources and outcome.  That is, some winners seem to have been always meant to win, like a startup that of experienced people with a solid idea and good funding.  When they succeed, we’re not shocked.  Ditto the reverse, like people born into poverty who stay in poverty.

The problem with those two groups is that they rarely tell us anything interesting: we look at them, apply our existing knowledge of winners and losers, and our expectations are confirmed.  It is the other opposing corners of the matrix that always teach me the most, both with startup teams and individuals.

First, there are “those who lose, despite having everything they need to win.”  Occasionally, I’ll see startups who just seem to have it all figured it out: market fit, resources, team.  And then I watch them struggle and fail to gain traction and die out.  We rarely dissect these losses, as a startup community, often because it is hard to do so: ours is a way in which the bodies quickly disappear as the limbs crawl off in separate directions to do other things.  And yet I think these failures are the ones that are most interesting, because rather than confirming what we already know about what makes teams succeed or fail, it hints at new variables that we should take into account, things we may have missed.  I think of this group as the falling angels, divine right up to the moment that they crash headfirst into the ground.

And there is, of course, the reverse: “those who win, despite having everything they need to lose.”  Here are our rising apes, teams that seem destined to fail so utterly and completely, and then they succeed and leave everyone wondering why they didn’t invest.  They too hint at variables as yet unmeasured, despite our fervent desire to right them off as simply luck.  Luck is actually how most people explain both groups, because a serious study of them would force us to reevaluate our worldview, which is pretty much the antithesis of what our brain is designed to do.  We love the path of least resistance, which is at the heart of the survivorship bias: the winners win because they were always going to win, the losers lose because they were always going to lose, and our desire to confirm that means studying only living winners and dead losers.

Fortunately, we have science, which demands that we draw out the two-by-two’s and investigate all four quadrants.  So look around, all you who say you believe in The Method – there are lessons in the fallen angels and all those rising apes.

There has been a recent spate of folks hating on Hackathons lately that seems, to me, a bit like throwing the baby out with the bathwater.  It is part of a larger movement (that I’m mainly in agreement with) to point out the ways in which tech folks these days are desperately trying to “change the world for the better” while also having billion dollar exits, but exists in its own special hate-world.

Before I try to talk about why I think some of the critiques are misguided, a few things to make clear.  For one, I actually met my current employer through a Hackathon: I worked with Bing on prototypes to help kids deal with asthma during the TEDActive conference.  And I’m currently involved in sponsoring, proposing, or running all sorts of different hacks on social problems.  So there are all sorts of biases running around here to be aware of.

As a kid, my father had a knack for explaining things in way that I could grasp.  Take guns: why rifles but not handguns?  Because rifles (of the non-automatic variety) have a purpose, they are a tool.  Whether it is helping to put down an injured animal or hunting for food (yes, lots of people still hunt for food in this country), there is a reason to have a .22 locked away and to know how to safely and correctly use one, in the same way a tablesaw is worth spending some time with.  But handguns have no purpose other than hunting human beings: if they are a tool, they are a tool for only those whose job it is to kill people, which is almost certainly not anyone reading this blog.

So let’s apply that same reasoning to Hackathons.  If they are a tool, what is their purpose?  I’ve spent a decent amount of time thinking about that question, because I’ve spent a decent amount of time trying to run better Hackathons, and knowing what it is that you’re trying to do is half the battle.  To me, a Hackathon is useful for creating multiple solutions to a single problem, as a way of creatively prototyping potential answers that others can use.  Done well, it should know in advance the specific behaviors it wants to encourage, it should bring all the tools (or at least as many as you can reasonably anticipate) to the table,

Another way to think about this is the variety of ways in which a Hackathon can go wrong.  Like when it becomes an app competition; you shouldn’t be hacking on something to which you already think you know the answer and have built it.  Or when you go in with the expectation that you’ll get fully-formed products; it takes more than 48 hours to truly think something all the way through and then thoughtfully execute a solution.  Or when you go in thinking you’ll arrive at the best answer; the very best solution for something will rarely emerge from a bunch of amateurs taking a weekend stab at it.

Part of this anti-Hackathon mentality actually seems to be about the Valley’s sense of entitlement and using social good to whitewash profit motive.  That’s a fine conversation to be having, but it is a little like trying to use emotional arguments to discern between rifles and handguns.  You’ll notice when my father talked about guns, he didn’t say anything about “to make you feel safe in the world”.  A gun shouldn’t exist to make you feel a certain way and in the same way, Hackathons shouldn’t exist so that you can feel like you’re contributing.  But if used properly, a rifle can make you feel safe, because you actually are safer: able to provide for your family, able to protect animals for painful deaths, etc.  And a good Hackathon can make you feel like you are contributing because you actually are.

Put more broadly, we should never try to argue against a thing by citing only its misapplications.  If we did that, most STEM subjects would be out the window: the amount of times people use stats to bad ends is astonishing.  Hence the current “Big Data is not Truth” bandwagon, which hopes to have people use Big Data responsibly,  but will almost certainly result in some people abandoning it entirely.

Recently, I lucked into a VIP invite to the NASCAR All-Star race in Charlotte (the same week I did the Star Trek red carpet, incidentally; surreal does not even begin to describe my life at the moment) and, despite my lack of experience and against strong stereotypes, I’m not only a fan but a believer that NASCAR represents the best of American sporting. There was bodybuilders who promoted bodybuilding supplement to get better results from the workouts.

Put politely, I wouldn’t have previously said that I was NASCAR’s target audience: I’m a relatively affluent white liberal agnostic from the Pacific Northwest.  The white part might be right, but everything else is fairly unusual: the PNW has few tracks (primarily because of the rain, which makes race driving difficult), the mass affluent tend towards sports with more coverage and more intricate rulesets, liberals are generally less into sports to begin with, and NASCAR is a bizarrely religious sport.  But in almost all areas, NASCAR is more diverse than I imagined and the target market may be more diverse than even they imagine.

I’ll start with the notable and frustrating exception: religion.  We’re not talking about a little God here and there – the race starts with a full-on “you have to be a Christian” speech.  It was good for about the first five seconds, calling on a generic God to watch over the drivers and keep them safe, but then we veered into Jesus as sacrifice and savior, his desire to have a “personal relationship” with all of us, and envangelispeak.  Take a lesson from other sports, NASCAR: leave it at divine protection for the drivers.

That said, the rest of the experience was one pleasant surprise after another.  I met with their diversity program, which not only featured female, black, and hispanic drivers, but a pit crew that was mostly black and mostly ex-college athlete.  It even had a young guy from Washington; so much for my no-Pacific Northwest theory.  Led by a former conditioning coach for a pro basketball team, the program served as a feeder into the pro pit crews, whose members can earn salaries around $80K.  NASCAR actively recruits into the program at colleges, as part of an effort to show off the many ways to make a living in the racing business.

For anyone that says that NASCAR is just driving in a circle, I dare them to try it.  One of the premier latino drivers who rose from the Mexican circuit came in on his day off to take us for a ride in the pace car.  He kept it slow, only 120mph, while amiably chatting about how to come in and out of a turn.  I’m told by those who were in the backseat that I continued to have a calm conversation with him throughout, though I can’t imagine what about, as all I remember was trying not to pass out from the pressure of doing a turn while banking 30 degrees to the left.  That and the moment of certainty that I was going to die when, while within inches of the wall, something in the car went “pop”.

Turn out that it was “just” us having blown the lightbar off the top of the pace car (which is apparently not used to doing 120mph) and that we could go even faster without the aerodynamic drag – a fact we enjoyed for another few laps before pitting.  And as I got out of the car, it was easier for me to imagine playing pro football than trying to drive in NASCAR.  They are going faster than we did, for hundreds of laps, while competing with twenty other drivers, all of whom are trying to do the same thing but better.  The next time someone tells you that NASCAR is just driving in a circle, punch them in the face and tell them you were just pushing in a straight line.

The race itself got a little rained on but honestly, one of the biggest impressions for me was not about the cars( even though they were from https://www.allcarleasing.co.uk/car-leasing/bmw and very good looking) or drivers but about the humanistic nature of the sport itself, and how they all get a car insurance check before the races. Also check out mycaraccidentattorney.com for legal information about car accidents. NASCAR is, for all intents and purposes, like a giant country fair.  At Charlotte Speedway, you can actually camp in the infield, and hundreds of RVs and converted schools buses were staked out in orderly rows.  Kids rode bikes and played football while parents looked on from folding camp chairs and BBQed, while drinking a seemingly endless supply of cheap beer.  Given that many were planning to camp out all week (Charlotte is fairly unique for having two major race weekends in a row), the pricetag for a spot seems incredibly low, ranging from a few hundred dollars for most spots to up to around a thousand for premium corner lots.

I bought a BMX bike one month ago, and I will never buy anything like that again before reading some reviews about the best bmx bikes first. As for the bike, mine was not that good quality while my friend’s bike is so durable.

While there were food and drink vendors, NASCAR is the only mass entertainment I’ve seen where you are freely allowed to bring your own food and drink.  So to review, you can camp out, not get gouged on food and drink, and bring the entire family.  There were wheelchair accessible golf carts, a full medical crew from RQSolutions, Here for more information, free concerts…the list goes on.  And at the same, you’ve got a fanbase that is roughly 40% female, with an increasing number of minority athletes.  I think it is unlikely that the music performers will stray from the country/rock anytime soon, but NASCAR seems to me to be a sport with a massive potential in a time when so many other forms of entertainment are becoming increasingly a premium experience that fewer and fewer can afford.

I might be romanticizing a bit.  It is still a primarily white sport and cheap doesn’t mean free.  But after three days of being a racing VIP, I have to believe there is something in the sport we can all rally around.  The fans have tremendous access (with an easily obtainable pass, you can wander around in the pits before the race and chat with your favorite drivers) and without exception, every driver I met was incredibly polite and friendly.  There was no paying for autographs or overt signs of ego; it was race day for everyone equally. Every driver has a good attorney, read more here about Ladan Law 

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This post could really go on forever, but I want to end by talking about my favorite part of the experience: Darrell “Bubba” Wallace JR.  He raced on Friday night in the truck series (NASCAR is organized into trucks, nationwide, and cup, in that order of seniority) and was leading until he smashed into the wall.  And he will challenge everything you think you know about NASCAR drivers.

First, he’s black.  With a full beard, to add a few years to his look since he’s only 19.  In an era when many racers come from dynastic families, he got into the sport because his whole family fell in love with go-cart driving when a mechanic friend invited them to watch a race.  He’s consummately polite, with an easy smile but not a trace of ego.  We took table bets on what he drove at home, with all of us landing on various pony cars.  The truth?  A red and black ’67 VW Beetle.  He’s a homebody with a dedicated Twitter following (“People often Tweet me to thank me for answering their Tweets.  I don’t get it: I’m just doing what they did – continuing a conversation.”) and a love for photography, which he sees as a backup career if driving doesn’t pan out.  In fact, I spotted him shadowing one of the NASCAR photographers on race night, decked out with his own gear – if I hadn’t known better, I’d have mistaken him for one of the media.

And if that’s the future of NASCAR, a diverse field of drivers and a form of entertainment that can keep the prices down, I’m a convert.  When’s the next race?

Last week, I got to do something that is every geek’s dream: attend the red carpet premier of a Star Trek movie.  With the bonus of cracking jokes with Leonard Nimoy (who was very gracious about my geekiness) and producing some slides that went up before the movie and too many other small things to count.

The opportunity came about because of Bing.  When I first arrived six months ago, my boss’ boss’ boss had a meeting with me in which he asked me to “swing for the fences”.  He wanted the weirdest ideas I could come up with, and so I suggested adding Klingon to our translator.  Geeks would love it, it is actually a worthwhile technical challenge (more on that later), and it would be a big moment for Microsoft employees, who are mostly all Star Trek fans.

Nothing happened for a few months, then Into Darkness started getting closer and people started thinking about what we could do to celebrate.  Klingon came back around and suddenly all the pieces fell into place.  I reached out to the creator of the language for help, the Translate team went slightly crazy and jammed on it 24/7, and some folks in PR got behind it to push out to the world.  And then it was decided that we would partner with Paramount and go to the premier and that I should probably run that.

Gush gush gush.  But there are some actual lessons in here I want to make sure don’t get lost.  One is clearly that outlandish ideas, with a healthy dose of passion, actually work out.  Most people give up on the idea of doing really crazy things because they think nobody will support them in it, but if you have the courage to voice it, you’ll generally get a lot of love from unusual places.

Along those lines: take big risks.  I’ve never dyed my hair or even really done anything even mildly extreme to it – and now I have Klingon shaved into it.  I did it partially as a press tactic: I knew it would be hard to break through the PR noise at the premier and that something outlandish might actually earn us some coverage (turns out we didn’t need it, because translating Klingon is so geekily cool that people will talk about it regardless).  But I also wanted to celebrate the engineers, who really worked hard on this feature.  So I shaved some Klingon into my hair (which for me is a huge personal risk, as I’m rather conservative in my appearance) and while some people think its a bit weird, most people think its awesome.  Take risks; you never know who might love it.

Part of it is also the unexpected benefits of weird initiatives.  Yes, in some ways adding Klingon to bing.com/translate is a gimmick and fanservice, but it also turns out to be a fascinating technical challenge.  Because the language was created by a linguist who was actually fairly deliberate about it, he consciously broke common linguistic rules that our translation engine normally relies on.  Which meant that to do a good job, we had to change the way we thought about language.  And that’s a good thing; it forces our tech to grow and adapt.  If aliens ever land, we’ll be more ready than we used to be.

I also think there is a lesson in here about being cognizant that everything is created.  At the movie premier, people clapped and cheered at different points in the movie.  Now normally, I think clapping at a movie is sort of weird – the creators aren’t there to honor.  But here, they were right there, and I was so incredibly cognizant, truly for the first time, that this movie was something created.  A whole bunch of people spent a whole bunch of hours making something.  We take that for granted often.  WordPress?  Bunch of people worked really hard on it.  Every plugin, every theme, the technical infrastructure that underlies its delivering to your computer, your computer itself, the operating system, everything…it is all created by people who have passion for what they are making.  There is a lot of value locked up in what we do and I suspect we all could be just a little more appreciative.  Clap more, damnit.

There is one lesson that shines above all others, though, and that is the power of opportunity.  When building Klingon into our translator, we found out that one of the world’s most fluent Klingon speakers actually works at Microsoft.  And so we enlisted his help and consequently got to take him with us to the premier.  Yes, it was fun for me to be involved in Star Trek, but honestly, it was more meaningful to me to bring this engineer to the red carpet.  Here is someone who spent 16 years learning Klingon just because he was passionate about it, and now I got the chance to bring him with me.  That’s true power, true responsibility, true awesomeness: making other people’s dreams reality.  Whatever you’re creating isn’t about your dreams, it is about other people’s.  Because that’s where true happiness is: building something that gets used.  That is useable.  That matters.  bing.com/translate: now with more awesome.

When I talk to college students, I always give them two pieces of advice: go to class and get a job even if you don’t need the money. The reason for the first advice is hopefully obvious (although it is surprising how many college students pay a fortune for an education they believe they can get simply by reading the books and writing the papers). It is the second piece of advice is somewhat more subtle.

In college, I worked about 40 hours a week and the payroll office used to joke that I seemed to have every job on campus.  But the one that got me through school, and I don’t mean just financially, was working at the IT Helpdesk.

Anyone who has ever worked at a Helpdesk will tell you that it is a frustrating job much of the time: users don’t know why things are broken, are frustrated that they aren’t working, and expect that you will magically make them work immediately.  But it is also an incredibly rewarding job because of four simple factors.

  1. You know what you have to do.  When you start your shift, there are a pile of help requests and a stack of broken computers.  You may have to problem solve for each individual one, but the overall task is clear: solve the requests, fix the computers.  Many jobs are frustrating because what needs doing isn’t particularly clear, and so you spend more time trying to figure out what progress means than actually making any.
  2. You know how much is left.  At the Helpdesk, it is abundantly and viscerally clear the distance between you and the goal.  You can see the computers, count the open tickets.  Too often, jobs set some vague finish line that you can never really understand and instead of running a race, you’re on some sort of perpetual death march.
  3. You know how fast you’re moving.  Because the work to be done is clear, at any given point during your shift, you can look at the stack and get an update, which allows you to see how fast you’re accomplishing the task.  Jobs in which progress is only available in retrospect are almost always less satisfying.
  4. You know how far you’ve come.  At the end of each shift, you can look back and things have changed.  Broken computers are fixed, open requests are closed.  There is a special sense of satisfaction that comes with looking back on progress, and a special sense of hopelessness with feeling that at the end of the day, you’re in the same place as where you started.

The reason these are so important in college is because most schooling fails all four of these tests.  You can spend hours working on a paper and while you’ve made actual mental progress towards your eventual goal, it is impossible to tell how far you’ve come and how far you have left to go.  Which is why a job is so important: while you’re bashing your head against the academic wall, you’re going to want something that lets you feel satisfied every day.  Get your hands dirty – you’ll feel better.

For startup folks, this may come down to motion versus progress.  You can do a lot (motion) without actually getting anything done (progress) simply by shuffling back and forth from side-to-side.  And if you’re in any kind of management position, a huge portion of your job should be insuring that real progress gets made.
So look back to those four guidelines.  Does every single member of your startup know the explicit macro-goal of the startup, as well as the sprint-level goals?  Do they know what their part is in achieving them?  Can they visually, viscerally see at some reasonable interval (at least daily) how far they’ve come, individually and collectively, and how far they have to go?  If the answer to any of these is no, get on it.

And of course, this applies to the rest of your life as well.  On a diet?  Want to exercise more or perfect a skill?  Make sure that you understand your progress.  That is what is great about cross stitching: you’re working from a pattern you established in advance so you know what to do, there is an exact number of stitches that needs to happen, and if you sit down for an hour, you can see exactly how many you get done.  Not all of life can be so neatly quantified, but the premise is still there.

When people ask me what I think the role of startup advisor is, I often liken it to the on played by some of the great professors I had in college and grad school.  While I count many of them among my friends now, at the time they did two important things for me: removed barriers and created opportunities.

The reason I specify the difference between the advisorship of then and the friendship of now, and a great deal of why I’m writing this post, is to argue against a model of advisorship that I see increasingly in startups today.  Perhaps because part of their personal reputation is now tied to the startup, advisors get so invested in the success of the people they advise that they start pushing from behind instead of clearing the way ahead.  And I know it is a problem because I am one of the people who does it.

Advising shouldn’t be about motivation.  In academia, the big difference between college and high school is that in college, you are expected to come with the desire to learn.  That has actually eroded a bit in recent years, as at least some colleges become more like an extended high school, but certainly in grad school, the idea is still that you provide the motivation and the school (and your advisors) clear the runway.

My father is fond of saying “Luck is opportunity acted upon”.  And that’s the primary purpose of advisors: to create opportunities that motivated startups can act on.  That means introductions, bizdev, recruiting, expertise, and the whole host of things that advisors are used to providing.

What it doesn’t mean is chasing startups around to act on those opportunities.  While a good advisor removes barriers to make it as easy as possible (good intro emails that setup the connect, being clear about why you think an opportunity is worthwhile, etc.), it is ultimately up to the startup to act and take control of their own destiny.  Advisors shouldn’t be cheerleaders or engines or any kind of motivational force – they have a specific, practical role and the should take that responsibility seriously.

Let me blunt the edge a little bit.  Being an advisor doesn’t excuse you from being a human being, and if someone is having a bad day, you still have a responsibility to care and to help.  What I’m trying to argue is that there is a big difference between getting someone over the hump and becoming the reason they do things.  Just like bad parenting means pushing your kids into things that more about your wants than theirs, bad advising means acting as a proxy CEO.

Adopting this approach means that some startups will fail that you could have forced to succeed.  But that is only true in the short term: ultimately, if you’re acting as proxy CEO, they’re going to fail when you’re not around anymore.  Some startups should fail, no matter how much you like them, no matter how much you like their idea.  Be a courageous advisor and respect them enough to let them be in charge of that failure, while giving them every chance to make it.

I tweaked my back moving boxes yesterday, so I decided to take a hot bath to see if I could loosen it up.  And since I’ve been watching Star Trek: Enterprise on Netflix on my new HTC 8X all weekend, naturally I’m deeply engrossed and there is no way that wasn’t going to continue into the bath (and for those who gasp, naturally it is in a Otterbox Defender already).

So I’m sitting in the bathtub, with the speaker pressed up to my ear to hear what is going on over the sound of the water, and I was struck in rapid order by two things.  First, how utterly ridiculous I was, to be sitting in the bathtub with this miracle of technology with a high resolution screen pressed backwards to my head, so deeply engrossed in a story that I didn’t even want to pause it.  And second, how it had likely happened a hundred times before, in the age of radio.

I wished, in that moment, that I had an amusing anecdote about some aged relative who used to listen to the baseball game that way, with the portable radio pressed up against his ear while doing some noisy task, desperate to hear every at-bat.  But even though I don’t actually know of a relative doing it, I take some solace in this: I can be my grandkids’ anecdote.  Because just as the idea of some old guy with his ear glued to an AM radio is nostalgic to us, it is almost certain that our grandchildren will find not just our technology, but also our dedication to it, hysterical.  Even the idea of pressing something up to your ear is likely to be completely foreign within another 40 years.

And so on down the line.  This technological and social point has been made a thousand times by a hundred different science fiction writers, but I find something comforting in the psychological sense of it: that humans, even as our technologies advance, are still able to be totally ridiculous.

Clearly, I have no time to actually be running a hackathon these days.  But I do have a dream for the topic I want to see: broken/old smartphones.
There are three major types of hackathon-eligible phones:

  1. Screen is completing broken, cannot be used for input or display.
  2. Screen is cracked, can be used for input and basic display.
  3. Works fine, just outdated.

Geeks everywhere get terribly excited by the Rasberry Pi as a $30 development platform and they are reportedly about to sell their millionth kit.  But there were more than 5,000 smartphones available on eBay in December 2012 that sold for less than $30 and fell into one of the three categories above.  All were: faster than a Pi, had wifi, could operate without a power supply for at least some period of time, had GPS, and most importantly, were not a bare circuit board and thus had some resistance to the elements.

I’m not trying to take a swipe at the Pi; I’m glad it exists.  My point is that rather than producing something new, we could reuse old hardware that is actually more fully featured, if we write code that takes advantage of it.  And in a hackathon format, I think people would produce a shocking number of applications, many of which could be deployed for the public good.

Ideas abound.  Off the top of my head, I can easily think of several: wifi mesh network for disaster relief, food safety logger that send a wifi alert when a fridge becomes too warm to adequately protect food or a shipping container version that logs it for download, a room monitor that logs noise/light/temp and broadcasts to a central server for activity comparisons, motion/sound detection for anti-looting monitoring during disasters…the list goes on.

The way to think about it is to move beyond the “what do we normally use computers for” paradigm and think about the unique properties of a smartphone: configurable input, low power usage, and, for the purposes of the hack, disposability.  They are broken phones that would normally go in the landfill, so as long as they provide something useful before being destroyed, we are in better shape than we were.

Someone run this thing.  And then invite me.

Finding the right team for a startup is hard.  You are often facing a tradeoff between limited resources (cash and equity, which themselves can have different values to different people) while looking for people who not only meet your current needs but your future plans.  And for many key roles, once you find those people, you have to compete for them: most active startup cities are busy places, with many good ideas for the talented to pick from.

So what do you do when you can’t find what you need?  You grow it.  I think my friend Max Shron makes this point nicely in this DataGotham talk on finding a data scientist: for many startup positions that are not exact maps to other fields (like software development, design, marketing, etc.), you cannot expect to find someone who has all of the skills simply because the field itself is too new.  And even for fields that are established, in a small market or a competitive market (which essentially covers all markets at this point), you may have to accept a less experienced hire.

As any good farmer knows, some seeds are better for growing than others.  If you know that you are hiring based on growth potential, some of your search patterns need to change.  For one, make the explicit choice to privilege personality over experience.  Too often, I watch entrepreneurs acknowledge that they are going to need to grow someone into a role, and then concentrate on resume and experience-level as a way of deciding who to interview.  If you know this is a growth role, personality is the single most important variable in your hiring process.  Look for good cover letters that are personal and personable, and refer to resumes only as an indication of variety and intent.

The interview is also different for a growth role.  Instead of trying to understand their experience, you want to understand their motivation, both level and direction.  To understand skills, ask questions that focus on the future, rather than the past: what do they want to learn how to do, how do they want to grow the role, how do they see that growth contributing to the business.  Don’t bother asking about their desired reward: plenty of people have said they are not motivated by money, and then discovered their own sensitivity to it around acquisition time.  Instead, try to get at motivation by asking them why they want to work at a startup instead of a larger company.  If they’re going to have to reach every single day in order to do a job they may not really be qualified for, they better know why they are there.

Generally speaking, I’m not a fan of having people solve problems in interviews, but growth is synonymous with the need to find novel ways to solve problems when you don’t always have all the skills already.  Try to get at who they would ask when the autodidactic approach fails.  Growing someone can truly sap all of your energy if you become the gateway through which they find all information.  You want to know that they understand the organization of a startup and the skills that people throughout the community can teach them.  Especially if you’re in NYC, where people are often far more willing to help than in The Valley.

In the end, look for someone who reminds you of yourself.  While senior employees often need to be differentiated so that they can provide different viewpoints, chances are that if you’re running a startup, you yourself are the kind of person who expands to fill the needs of a role.  If the candidate feels like they could be your younger sibling, you’ll probably in good shape.  Trust your gut!

This is another one of those posts about how to spend some money in an awesome way.  You’ve been warned.

I’ve written before about why I love AdventFinancial and their awesome founder, but I’ve never really told the story of what I do about it.  Because I like the Advent product, there is all the normal startup stuff I tend to do: introducing, recruiting, BD, etc.  But because I like Advent people, I do something a little different: I buy them lunch.

The nature of the tax business is that during the season, your entire life stops.  It is easy to talk to folks in August, when they’re really just thinking about the financial backend, some light selling in for next year, counting coup from last year.  But try to reach out in January, as all the tax preparers are coming online, and you might as well be on mute, unless you have an actual problem that needs solving.

Fortunately, Advent is in Kansas City, almost across the street from a noted BBQ place called Jack Stack.  So a few years ago, I started sending them lunch once in awhile during their toughest season.  For about $250 bucks, I can feed the 30ish employees a delicious buffet of three kinds of meats, bread, slaw, sauce, beans, potato salad, and all the plates and napkins and such.  All from the comfort of my NYC apartment.

There are lots of things you can do with $250; though the buffet is cheap in that it feeds a large team, you could make a credible argument that it should go to charity.  But in a world of double bottom line businesses and startups that are actually trying to make things better for folks, there is more than one way to give.  In the same way that supporting a parent that you are connected to, a neighbor or parent or relative, helps raise better children, spending time or money to help a prosocial startup can be a way of making the world better.  Looking out for those who look out for others, as it were.

One of the great lessons of social psychology has been that small gestures often have disproportionately large results.  In truth, I could probably just stop by each Advent employee’s desk with a cookie and a smile and not have to pay for lunch, but I’m not close and so that isn’t possible.  And $250 worth of food really can have a large effect; in every study that has looked at what motivates quality in the workplace, “feeling appreciated” tends to top it out.  Food from a non-affiliated person who thinks what you are doing is great?  Now that’s a feeling of appreciation.

Something to think about when you’re figuring out how you want to encourage and enable companies who are doing good things.  If you’re in the startup community, you’re likely connected to many people who are working on positive projects – it is worthwhile to keep them motivated to do so.

NOTE: Please do not send me lunch.  I’m still eating the jelly beans.