Archives For CEO Friday

Crazed ramblings by the CEO.

At some point, a startup outgrows its lack of structure, but isn’t yet ready for the real deal. What do you do? There are some lessons to be drawn from how P2P networks grappled with the same problem.

1. Fully Connected (2-4 people)
When a P2P network is very small, every node sits next to every other node. If there’s something you need, you just directly ask the nodes around you, and they can give it to you in one step. This is akin to the early days of a startup: just turn to the left or right and every problem is solved.

2. Gossip Protocol (5-10 people)
As the network grows, not every node sits next to every other. But this is fine, because the network is still small: even if your peers don’t have the answer, odds are they just need to ask one of their peers, and the answer is found. So every question can be answered in 2 steps, which is still pretty good.

3. Supernodes (10-20 people)
However, as the network continues to grow, sometimes gossip isn’t effective: it’s possible that there are nodes sitting more than 2 steps away. In startup terms, this means peers who are off in their own direction, and nobody knows what they’re doing. But because everybody has already accepted there are things both they and their peers don’t know, it’s easy to assume that somebody else knows what they’re up to — when in fact nobody does.  Accordingly, people can be overlooked: they don’t get the support and oversight they need to be effective.

To solve this problem, a small group of well-intentioned employees — generally without any formal acknowledgement — steps up to take on greater responsibility. They don’t have any formal titles; nobody technically reports to them. But everybody knows they are doing far more than being individual contributors: they are “supernodes” who just take it upon themselves to pay attention to more than most. They are the people who walk around and ask questions.  They notice when people are unhappy, overwhelmed, unsupported, or unsupervised. They are the people everyone turns to when nobody knows the answer.  They are the unsung heroes who keep a startup from imploding under the weight of success.

But inevitably, the supernodes themselves burn out. After all, they’re consciously doing more than anybody else — but without any real extra incentives, resources, or authority. And when a supernode burns out, the whole network they support burns out, too.

Up until very recently, that’s where we were. So we’re moving on to the next stage: DHT.

4. Distributed Hash Table (21-?? people)
Because supernodes are volunteers, they don’t necessarily have any formal accountabilities — being a supernode isn’t a job, it’s a calling. And though over time supernodes tend to focus on certain areas, and though all nodes tend to learn what those areas are and act accordingly, those focuses aren’t documented or even formalized. This means new employees don’t know who knows what; people don’t know who is more qualified to make a decision than the next person. A supernode can only do so much as a volunteer: at some point your organization needs to upgrade to a DHT.

At a high level, a “distributed hash table” is a data structure where given any particular question, you can determine who knows the answer — in one step.  No searching, no gossip: just ask the right person and they will know.  In organizational terms, it’s kind of like an org chart: it documents which people are in charge of which areas. Ideally anybody can look at this chart and immediately determine the correct person to ask any question.

But it’s only a partial org chart: only the supernodes are put into the chart, and all the other nodes are left ambiguous. It’s not about strictly defined teams operating under a chain of command — it’s about a mob of people, where some people carry megaphones. Anybody can switch who they follow at will, depending on what they’re trying to accomplish. But those carrying the megaphones coordinate to ensure that the mob overall continues heading in the right direction.

That’s where we are today. Expensify is a mob, with megaphones. Naturally, I reserve the loudest megaphone for myself (as would any benevolent dictator), but more and more it’s the jobs of the supernodes to keep the mob moving forward — with me just helping coordinate behind the scenes.

How long will this last? I’m not sure. Like so many things, our lack of overt structure has worked much longer than I think anybody realistically thought was possible. Indeed, I attribute how well things have worked so far entirely to the fact that we only hire a very particular sort of person who can thrive in this environment. But I’m confident that it’ll keep us moving forward at our already astonishing rate, to whatever level comes up next.

Q: Why not a strict hierarchy; isn’t that more efficient?

A: In content delivery terms, that would be a “broadcast tree” — you have a single source, which broadcasts to the first set of nodes, each of who broadcast to the second set, out until all nodes get the content.  It’s a top-down control network, and yes, it is optimally efficient.  In an established company where all the kinks of the business have been ironed out, everyone’s job is well defined, and the success of the organization rests upon minor tweaks applied top down — yes, it’s ideal.  Most large companies are structured this way for a reason.

But a startup is nothing like that.  At least, our startup isn’t anything like that, and we all quit places like that to come here.

Rather, it’s more like I throw a flaming torch way out ahead of us, and we all try to figure out how to get there.  Sometimes it involves building bridges, blowing up mountains, and occasionally burning our boats behind us.  But my job is only to figure out (roughly) where we need to be: how we get there is up to the mob.  So our structure is optimized to put maximum control into the hands of the most people.  It can be chaotic, confusing, and sometimes a bit scary.  But it’s a lot more productive, and infinitely more fun.

-david
Founder and CEO of Expensify
Follow us at @expensify

My hat’s off to the Yammer team for their $1.2B acquisition by Microsoft!  I think everyone else has already said about everything, but I wanted to add my own spin: the incredible valuation of Yammer isn’t that it’s social — that’s so 2012.  Rather, Yammer’s value is that it is pioneering a revolutionary sales model that is going to wholly transform the enterprise space.  I wager Microsoft bought Yammer not because it needed to plug a social hole, but because they saw it as fundamentally lower-cost-of-sale model that threatens Sharepoint’s long-term success.  This wasn’t about adding Yammer’s revenue, but about preventing an even greater loss of Sharepoint revenue.  This was a defensive move on Microsoft’s part to avoid being disrupted by a competitor they can’t possibly beat.

Said another way, I suspect Microsoft didn’t buy Yammer because they wanted a piece of their $22M revenue stream.  Especially as, so far as anybody has reported, Yammer didn’t get that revenue in a profitable manner.  Rather, Microsoft bought Yammer because they were afraid if they didn’t, people would gradually leave Sharepoint for it.  Even if Yammer can’t profit from those users, Microsoft can, and they want to ensure that they do.

Like anything, I’m sure there are a hundred angles, all of which bear some grain of truth.  But the one I hadn’t heard was about Microsoft’s deep seated fear that whether or not they wanted Yammer, they needed it.

That might sound obvious. I was employee number one, and I’ve been personally involved in hiring everybody else in the company. So I less than anyone should be surprised by what this team can do. But when Tom builds a remote-controlled, webcam/microphone/speaker equipped, four-wheeled robot just so Tony can attend a Thanksgiving party — I mean, who can’t be surprised by that level of awesome? And then for Tony to casually drive this silly robot into a roadmap meeting to discuss some fundamentally radical mobile ideas, not the least of which is how to maximize the value of our totally custom cross-platform mobile layer — my mind is blown.

I’m not saying every day feels like living in some parallel universe where Sneakers meets Ocean’s Eleven. But some do, and I can’t help but think “Damn! I love working here.”

PS: Did I mention we’re hiring? Programmers, salespeople, and desperately looking for a designer. Know any? Send them our way, please!

When giving the same pitch over and over, you quickly settle into a specific way of delivering a line, and then say it so often it becomes second nature. Most conversations I have with investors or the press really just involve stringing together a series of well-rehearsed snippets that address pretty much any question I could ever be asked. One of those snippets starts with:

“Now, I don’t read many ‘pop business books’ (air quotes), but there’s one I really swear by called the Innovator’s Dilemma.”

That’s been part of my pitch for a long while now. It’s even on tape. So guess how pleased I was to learn who else swears by it? None other than the late great Steve Jobs.

However, never one to pass up an opportunity to disagree with Mr. Jobs, I should mention that I took away a different lesson. Granted, I haven’t read his biography so I’m going off of other reports. But I’ve heard his opinion summarized as:

“Over-focus on profit is the problem, and the solution is to focus on the product.”

Granted, that’s watered down to a nice-sounding but highly ambiguous statement, so I don’t really know what he meant by that in practice (or if he’d have even agreed with that summary). But despite what he may or may not of have thought, I’d say the pursuit of profit isn’t itself the problem. Profit isn’t some happy accident that can only be pursued out of the corner of your eye. Rather, it’s how you pursue that profit that causes the dilemma.

Specifically, if your profit depends on continuously abandoning your core to move up market, you’ll eventually hit the top and be incapable of going back down. This is the inevitable fate of any (successful) organization with a direct salesforce that:

  • Is compensated through commissions, and
  • Sells to leads gathered from outside the core userbase.

Indeed, if your salespeople are encouraged to always go out and get the “next biggest deal” — and are given free reign to get it from anywhere — how else could they possibly accomplish that goal without abandoning the core market? If there aren’t an equal number of people pushing the product down into smaller markets, naturally you’re going to find yourself drawn into inexorably bigger markets. An organization like this can’t help but use their current market position as a stepping stone to move somewhere else, which as the book explains, is a fantastic rocket ride up to the top followed by disruption from below — typically by another rocket using the same strategy, and then another after that. It seems the cycle of life.

Mr. Jobs broke the cycle by (apparently) decoupling product focus from sales. And luckily he’s a genius with the intuitive vision to predict where the money was, so it paid off.

But I think that’s a risky gamble that could have gone the other way. Apple bet it all on black (or brushed aluminum, in this case), and it paid off handsomely. But don’t forget that it didn’t pay off so well a couple decades back when he tried the exact same strategy: Apple was only able to have this stunning rebound because of its previous tragic decline.

So I feel there’s got to be some other way to break the cycle — some way that doesn’t require going “all in” on the gut instincts of a genius at the helm. Some way to build an organization based on repeatable, customer-focused development that can be accomplished by mere mortals instead of an endless game of “double or nothing” played by the gods.

If product isn’t the answer, and sales isn’t the problem, then where else to look?  And that’s where I lay the blame at something surprisingly benign: the lead source.

Nobody talks much about lead sources. “Leads” — the people at which you point your salesforce — are just assumed to come from the same places other companies get them. SEM and SEO to landing pages, going to conferences and gathering business cards, channel partners, affiliate programs, buying contact lists from the many, many people who sell them, etc. And you might argue that all these leads come from such a diverse array of sources that you’re naturally inoculated against myopia. But all those sources have one thing in common: none of those people actually use your product.

So if your salespeople are always talking with people who don’t use your product, and are always incentivized to start with the biggest first, then they can’t help but pull you away from the needs of all the smaller people who already do use your product.

(This is aggravated further by outside sales typically talking with the “decision maker” — a person whose likelihood of actually using the product they’re buying decreases as the company size increases.)

All of this inexorably shifts your customerbase’s center of gravity up market, day after day, such that even if you’re in the most customer-focused organization, you can’t help but realize “our customers are getting bigger, that’s where our resources should go”.  This inevitably de-prioritizes the initial customers who got you where you are, in favor of the bigger customers that you’re always trying to get. It’s a vicious cycle; it’s a dilemma.

But what if you could somehow keep your center of gravity stable? What if instead of building new features, you just kept your organization focused on improving the features you already have, for the same people who already use them?  It means you have a lot fewer features.  And require fewer engineers.  And have less to support, all of which is higher quality.  Wouldn’t it be great if you could do this, and still achieve your growth and profit goals?

There are some obvious ways to try. One way is to just not take on larger customers — maintain a laser focus in a particular customer segment, always resisting the urge to move upmarket. That’s one way. But I wouldn’t recommend it — in any market, upmarket is where the money’s at. The margins are thicker, the opportunities bigger, the names sexier, etc. Any company that has no interest in going up market is one that intends to be overrun (or at best, acquired) by someone who does.

Another obvious way to do it is to have two teams: one focused on moving up, and another on moving down, such that you always balance out your growth. And that might work, if they’re very carefully balanced.  But that seems impractical to manage, so again, I wouldn’t recommend it.

A third option, and the one I would recommend, is to focus your sales effort on people who already use the product.  This way you avoid shifting the center of balance and create an organization focused on increasing engagement amongst existing users. This approach addresses the core deficiency of the lead source itself: the fact that new leads don’t use the product.

Now you could argue “Of course they don’t use the product; if they did then sales wouldn’t need to talk with them.” If the only way to use your product is to buy it, then that’s quite right! But as we know, that needn’t be the case. The internet is full of services that offer huge value at absolutely no cost. Services that have millions of “users” who aren’t yet “customers”. People who already use the product, even if they haven’t yet bought it.

What I’m describing of course is the classic “freemium” model: give away basic functionality for free such that some users will decide to upgrade. This isn’t terribly new.

But what is new is applying the freemium model in a space where the “deal size” is big enough to enable a sales team to make postive-ROI sales (where the cost of the sale is exceeded by its revenue). This isn’t Farmville — no salesperson is going to earn a commission by convincing you to buy a purple cow. And this isn’t a consumer product that encourages you to upgrade to a $10/mo plan. This is an enterprise product, with customers having hundreds or thousands or more employees. And using the existing users within an organization to serve as leads into converting the organization overall.

Ultimately, the primary purpose of sales is to drive up market. And it’s a slow, steady march taking on new customer segments as you firm up support in existing segments.  But this process is only destabilizing if doing so distracts from the core userbase. If the sales leads are instead drawn from the core userbase, however, then the only way to increase leads (and thus increase sales) is to also grow the core userbase from which the leads are drawn.  So long as your leads some from your active userbase, then you simply can’t lose touch with it.  This makes the entire organization — from the most senior salesperson selling the largest deal, to the most junior support person talking with individual freemium users — play for the same team, aligned toward the same goals.

In a sense, the whole company is spinning up the same flywheel.  It doesn’t matter who pushes, where, or how hard: the bottom-up adoption curve allows everyone to contribute to top-line sales success, no matter where they are in the organization.

This is how you solve the innovators dilemma, without sacrificing the move up market, and without losing touch with the core.

At the very least, this is the strategy that Expensify is using, and it seems to be working pretty well for us.

Note: If you’re interested, consider joining our “Salesforce of the Future!

After a quick halftime break, let’s resume the second half of the series. As mentioned in the past, this is the fourth in a six-part series elaborating on a presentation I gave at the AlwaysOn OnMobile 2011 conference titled “Disrupting the Enterprise”. I suggest reading from the start (or watching the video) and then continuing on below.

Recap: The Three Conditions Underpinning Sales (N+1).0

So there are three interesting conditions at work:

  1. The “Consumerization of IT” empowers employees to promote products up the chain in an enterprise
  2. “Word of Mouth” has become a “Winner Takes All” phenomoneon where early dominance of the global conversation becomes self-reinforcing
  3. There was a one-time “Cascade of App Stores” that gave a substantial and lasting advantage to first movers

The upshot of all of this is I feel there is an enormous opportunity to reach into previously inaccessible parts of the market using a sales strategy that I call Sales… 3.0? 4.0? Let’s just say 10.0 to get ahead of the curve. The very modestly named “Sales 10.0″ strategy conists of three principles:

Principle #1: The Bottom Up Adoption Curve

Many industries share a common chart: a very wide base of customers at the “bottom” of the market, narrowing down to a very pointy tip of customers at the “top”. What “bottom vs top” actually means and how it’s quantified depends on the market. But if you’re reading this blog, odds are you’re targeting the “bottom” of the market while some other big company has a stranglehold on the “top”.

At some point, the big company at the top will decide it wants to capture some of the action down at the bottom. It’ll do this by instructing its massive salesforce to start going after smaller deals — probably by adjusting their commission incentives to make smaller deals more attractive than they’d normally be (or by hiring a new sales force devoted to just this). If they’re really serious, they’ll come out with some new product targeted squarely at the small business space.

But don’t worry, because odds are no matter what they try, it’s not going to work. The product and skills needed to operate in and maximize the value of the top of the market just don’t translate down market. Small businesses aren’t small versions of big businesses, they’re an entirely different beast. Any company optimized to hunt whales just isn’t suited to trap squirrels.

This is where the “bottom up adoption curve” comes into play.

In the top-down sale, you typically start talking with senior management — nobody really experiences the product until they’ve already signed off on it. But the bottom-up sale reverses the process, giving a trial of the product straight to the rank-and-file employees, before senior management even hears of it. So while a top-down salesperson would fight tooth and nail to get a limited trial authorized by senior management, the bottom-up product just walks in and starts a trial on day one. Top-down requires some high-level introduction to start a conversation with a new customer, while bottom-up can start with anybody, anywhere in the company — the lower the better. While the top-down company builds a wide range of complex features that appeal to management, the bottom-up company builds the few core features that the actual users of the product love.

The end result is the bottom up adoption curve reaches out directly to the innovators in every company, empowers them to initiate a limited trial without the need for anybody’s permission, and then champion the results internally — essentially giving you an “inside man” pulling for you in every sales lead.

So it’s “bottom up” because you start with the users first, and percolate up to senior management only after the trial has already successfully completed (and thus, there’s no reason to say no). And its an “adoption curve” because it takes a graduated “innovators first” strategy where those who come before learn and train the people who come after (as opposed to a top-down sale where all users are signed up at the same time). It allows your product to be pulled into organizations by the people who need it most, and then sold to all internal stakeholders by someone intimately familiar with the local conditions — all without you ever picking up the phone.

So it’s a system that definitely works in the small business space. It’s very hard to design a product to accomodate it, and it’s very hard to get all the incentives to line up. But when you do, it takes off under its own steam, with each new user expanding your salesforce — and thanking you for it. Everybody wins.

But it’s also “bottom up” in another sense: with this technique, you start with the bottom of the market, and gradually work your way “up” to the top.

Granted, this is the only thing that will work at the very bottom of the market. The deals are so small, and there’s just so damn many of them, you absolutely need to have something like this to survive. The most important feature you ever build is the one that finds the next customer, automatically, while you’re asleep.

And to be fair, if you were only going to sell to the top of the market, you wouldn’t bother with this. It’s really tricky stuff, and it’s so much easier and more effective to just go out and get a sales force (assuming the cost of sale is substantially less than the revneue it brings).

But if you *do* start out at the bottom, and if you *have* already gone through the trouble to make this work… why not use it upmarket as well? After all, there’s nothing about this process that doesn’t work in large companies as well as small. Sure, big companies have bigger requirements. And you might need to get more clever about how exactly you support your internal champions — giving them the tools they need to start a trial without anybody noticing, and promote your product up the food chain in a non-disruptive fashion. But maybe it’ll work there too?

The bottom up adoption curve is a strategy for not merely taking over companies, but taking over markets. And as we’ll see next week, holding onto them forever when you get them.

Thanks for reading, keep an eye out here to read more next Friday!

Previous: A Cascade of App Stores (3/6)

This is the third in a six-part series elaborating on a presentation I gave at the AlwaysOn OnMobile 2011 conference titled “Disrupting the Enterprise”. I suggest reading the first (or watching the video) and then continuing on below.

Condition #3: A Cascade of App Stores

This third condition is done; it was a one-time wave that will likely never be repeated. I’m referring to the overnight rise of a series of web and app stores, and the cascading effect of new stores inhereting the rank of the old, creating a sort of “meta rank” where apps on top of one tend to dominate the rest.

It all started with the iPhone. (You might argue it started with the BlackBerry or even Sidekick, but those stores never really caught on like it did for iPhone.) It seemed like overnight a million apps appeared, vying to appear at the very top of a seemingly infinite list of applications in each category. Furthermore, because your rank was largely a function of your install rate (and your install rate was largely a function of your rank), this created a feedback loop where the people at the top tended to stay at the top and increase their lead over time: it created a strategic high ground with incredible staying power.

Quick on the heels of iPhone was Android. To a degree, the apps at the top of the iPhone App Store were the first ported to Android, and re-established their dominance in the Android Marketplace. (The difficulty of porting to a new platform allowed a bit of discrepancy to appear, but the iPhone ports came in with an advantage over original Android apps.) And then after Android came the Amazon, Verizon, and Windows Mobile app stores — each reinforcing this hierarchy to a greater or lesser degree, and each opening a brief window of opportunity that has since irreparably closed.

(As an aside, the conventional wisdom — so far as I can tell — is to just buy your way up to the top of the app store using TapJoy and its brethren, each time hoping that some of your rank sticks. This does seem to work a bit. But it also tends to flood your data with low-quality leads, such that the more you employ this strategy, the less actual awareness you have about whether any of the signups are worth having. Furthermore, it seems the quality of the installs “at the top” aren’t as good as the quality somewhere in the middle: people who scroll down a couple pages to find you seem more loyal and genuine than those that simply install whatever app appears at the top of the list. But that’s a different topic.)

The upshot is in rapid succession, the mobile app stores established a murky order that tends to slosh around a bit, but generally settle back where it started. I speak here from experience: we missed this wave, and thus our app has a very low rank on each store — and there’s very little we can do about it except fight hard each and every step. But as luck would have it, we were given a second chance.

Right after we launched, Salesforce held a fortuitous contest to create the best expense reporting app, listing the result in the Salesforce AppExchange. We did really well, and earned our place amongst the illustrious “Force 40″ — the top 40 Salesforce apps. Right around then, Intuit saw the meteoric rise of the iPhone and Android app stores and thought “I wonder if we can do the same with QuickBooks?” So they came out with the Intuit App Center. And naturally, they approached us to be early adopters, primarily due to our high rank in the AppExchange. This good fortunue repeated with the launch of the Google Apps Marketplace, which obviously couldn’t launch without the top Salesforce AppExchange and Intuit App Center apps (including us). This process repeated a couple times more, and now Expensify appears at the top of all the major web app stores, much to our delight.

But all that is done. Sure, new app stores open up every day — for both mobile and web. But all the major players have already made their moves, and their not going to make them again. That wave has washed ashore, and though we can scramble along the beach for a new position, those that were washed far in have a large, enduring lead over those who weren’t.

Why you should care: If you have an app with high rank, celebrate. If you don’t, prepare for a very long, hard slog to the top. It’s not impossible — and there are snakeoil salesmen touting every dirty trick to accelerate it — but ultimately the deck is stacked against you for the forseeable future.

Tune in next week to continue the series and read about how these three conditions have created a new opportunity for selling into the enterprise in a faster, lower-cost, and higher-quality way than ever before. See you then!

Previous: Word Of Mouth is Winner Takes All (2/6)
Next: The Bottom Up Adoption Curve (4/6)

As I mentioned last week, I recently gave a brief talk at the AlwaysOn OnMobile 2011 conference titled “Disrupting the Enterprise” (video). I was asked to give a bit more detail, so I’m doing that now, in six parts. This is the second one; read last week’s and then continue on below.

Condition #2: Word of Mouth is now Winner Takes All

A second, no less important condition is how blogs and social networks now cause conversations to converge swiftly and globally. This means that word of mouth — something that might have previously shown strong regional or vertical tendencies — has instead become a universal phenomenon with “winner takes all” properties.

Now I’m no social scientist, and I think this trend has been growing for a long time. But there are more options than ever to directly broadcast your ideas to world in a completely unfiltered fashion. Prior to the Internet, what were your options to broadcast to the world without the permission of some large publisher? Ham radio? BBS’s helped, but were mostly regional (due to long-distance fees, and Fidonet was a pain). Usenet was limited to very techy spheres. IM was instant and global, but not broadcast. Email mailing lists and web forums are starting to get truly global reach amongst average folk. Comments on blog posts are even better — it combines quality editorial content with feedback from the unwashed masses. (Oddly, Facebook is a step back as you only talk to your friends.)

But Twitter takes the cake. Now anybody can broadcast from essentially any device, using essentially any form of media, to essentially any number of people — at essentially no cost. The “follower” model allows it to take advantage of quality (*ahem*) editorial content, while realtime searching, hashtags, trending topics, and retweets allow even the unpopular to get heard. It’s as close to an unfiltered meritocracy of ideas as we’ve ever seen. All this creates any number of interesting consequences. But of particular relevance to this discussion is that it helps the whole world converge on a consistent story with exceptional speed.

I say this based on the theory that the “distance” an idea travels is some function of the “strength” of the idea and the “resistance” of the medium, and that given two equally strong but conflicting ideas you’re more likely to believe with whichever one you’ve heard longest and most frequently. This means the more resistant the medium, the more it allows competing ideas to survive simultaneously in different regions or “verticals”. Then, by the time the ideas “collide”, each has built up a following that has heard it so often for so long that they’re not nearly as receptive to the idea as had they heard them both first.

But all these advances in broadcast communication have reduced the “resistance” of the medium to such a degree that every new idea is heard by almost everyone, all at once, everywhere in the world. When TechCrunch covers a new product, it’s a matter of hours, minutes, or seconds (but certainly not days or weeks) before everyone who might conceivably care knows. This triggers an immediate global discussion to evaluate the impact of that idea, with the winning option being broadcast further and faster than the loser. The result is on any given topic, there’s one major idea that dominates (the winner), maybe one alternative (the runner up), and that’s about it. Because as information flow goes up, attention span goes down (Twitter’s 140-character limit illustrating this nicely), meaning it’s simply not possible to sustain more than a couple competing ideas on a given topic for long.

When the conversation dies down and everybody moves to a different topic, the winning idea gets the lion’s share of the attention. And because everybody is biased in favor of what they’ve heard the most in the past, the winning idea of the last conversation has an advantage in the next conversation, causing it to strengthen its position over time. So in a field of largely equivalent ideas, once one gets a slight edge, that edge just keeps increasing forever, until all the other ideas are forgotten — even if they might have been nearly as good in the first place.

Why you should care: If you find yourself in a field of equals, with none of you getting any attention, beware: once somebody gets a little attention, they’ll get all the attention. Make sure it’s you.

Expensify example: Even though Expensify is without question the leading small-business expense reporting system out there today, we didn’t start out that way. In fact, a few other very similar options came onto the scene right before or around us (and new ones are springing up all the time). And though I wouldn’t say we were all equivalent (because we actually all had very different approaches), I would say that none had a clear advantage over the other. But somehow we got an edge. I’m not sure exactly what happened: we had good early coverage, knew some good people, were emphatically interactive with and supportive of our early adopters, and just had a really good product. Maybe even the best product. But once we had a slight edge, it wasn’t so much that people suddenly started talking about us a whole lot, but they simply stopped talking about the alternatives. The discussion shifted from “There are several options including X, Y, and Z” (where we might not be listed) to “Concur is for big companies, Expensify is for small companies.” And once you hear that a few times — especially when you try us and realize that we’re actually quite good — it’s just not worth your time to investigate alternatives. After all, if nobody discusses them, how good can they really be? Granted, I’m hesitant to say any of this without knocking on wood — I’m extremely conscious of how fast the tides can turn.  But I’m willing to take a chance as I think we now have a very comfortable lead in terms of functionality and usability over any competitor. But back then we didn’t, though you wouldn’t have known it by listening to the global consensus.

 

Tune in next week to continue the series and read about “A Cascade of App Stores”.  (Follow us on Twitter at @expensify to be notified when it comes out.)  See you then!

Previous: How To Disrupt Your Industry (1/6)
Next: A Cascade of App Stores (3/6)

Last week I gave a brief talk at the AlwaysOn OnMobile 2011 conference titled “Disrupting the Enterprise” (video). It was pretty well received, and I promised to write up more that Friday.  Well… it’s two Friday’s later, so here goes.

To start, this isn’t really about Expensify. It’s about the conditions that allow Expensify to exist — conditions that simply weren’t true a few years ago, and at least one condition that will probably never be true again. It’s about conditions that I’m theorizing affect (or could affect) more industries than just expense reporting, including maybe yours? If so (or if not) I’d love to hear from you in the comments. Because ultimately, my goal is to learn if our experiences are unique, or if we’re just missing something, or if maybe we’re actually ahead of the curve and have some valuable lesson to share. Whatever it is, let me know what you think.

Condition #1: Consumerization of I.T. == Employee Empowerment

The hip term used to describe the first of these conditions is the “consumerization of I.T.”. I think that name is supposed to convey that “information technology” departments (does anybody even use that term anymore?) are grappling with a massive influx of consumer products brought into the work environment. As best as I can tell, this really started in earnest when people started bringing Macs to PC-only shops. They didn’t ask permission, they just sorta plugged in and got to work.

(In my case, during my very brief “experimental” time after I left Windows and before I adopted Ubuntu, I had a Mac. It was during that short window that my tiny startup was acquired by a very large company, the sort that uses the term “IT” with a straight face. At the time, they didn’t officially support Mac: none of their custom tools worked on it, and it violated all sorts of internal company policy to even plug in an unauthorized device. They gave me and my team PC’s and instructed us to use them. Instead, we imaged the hard drives and installed them on Mac VMs — to use in those rare instances we needed them — and then ported the tools we needed to Mac. It took a day, and made questionable use of some SSH proxy servers placed strategically on the internal network, but on day two we were productive again.)

I’d wager that in most cases, IT didn’t even realize this was happening until they strolled by somebody’s desk and saw the wrong color laptop plugged in to the corporate LAN. If they said anything at all, the conversation probably went like:

IT: “Hi there, we don’t support Macs.”
Employee: “It’s what I need to be productive, go talk to my boss.”
IT: “Ok…”
(one day passes)
IT: “New policy, we support Macs!”

I think Macs led the charge, but then iPhones followed suit in BlackBerry shops, DropBox followed suit in SharePoint shops, etc. The specific pairings of corporate/consumer technology are debatable — and I don’t know that one always replaces the other versus just obviates it — but I think the results aren’t: more and more, when employees want something, they get it. Maybe not always, and maybe moreso in smaller companies over large, but it’s a growing trend that I don’t see reversing anytime soon.

Which is why, incidentally, I don’t like the ambiguous “Consumerization of IT” term. Not only is it straight up unclear, but it emphasizes the wrong thing. Whether the technology is “consumer grade” or not is far less important than who picks it. And the key point is it’s the employee who is doing the picking. In an area where employees previously followed strict IT policies, they are now empowered to make their own choices. This is why I prefer to call this trend one of “Employee Empowerment”.

Why you should care: Previously, if you wanted to sell into an enterprise, you had no choice but to go straight to the policymaker. But now there’s an opportunity to enter the enterprise through the back door: the employees themselves. If you can find a way to get employees to individually and proactively adopt your product, then they sell you to the policymaker when that time comes. Which is great as they know the local conditions and political landscape better than you. It’s like having an “inside man” championing your every sale.

Expensify example: Once upon a time there was a company that processed a lot of expense reports using paper printouts of Excel spreadsheets with physically affixed paper receipts. On a bright and sunny day with magic in the air, a department manager takes the next of an endless series of expense reports off a tall stack of envelopes, only to find that it is a printout of something called Expensify. All the same information is there, all the receipts are there… just not in the format expected. He sets it aside. Later, he finds another employee has done the same — an employee on the other side of the country, who likely has no interaction (or coordination) with the first. Eventually enough employees have done this that he reaches out to Expensify to start a trial. While the trial is ongoing, more employees — without even knowing Expensify is being trialled by the company — submit Expensify reports. Sometimes via printouts, sometimes by emailed PDFs, and sometimes submitted online using the service itself. Eventually that department adopts. Then other departments. Now everyone uses Expensify and they’ve just finished processing their 5000th Expensify report. All due to a few proactive employees just trying to be productive.

Tune in next Friday to learn how “Word of Mouth is now Winner Takes All”. (Follow us on Twitter at @expensify to be notified when it comes out.)  See you then!

Next: Word Of Mouth is Winner Takes All (2/6)

“Go West, young man!” Those words have rung true for many a generation, and will likely ring for many more.  Sure, the meaning of “west” has gradually become more precise, and the tools have definitely changed.  But the spirit remains the same: leave the comfort of where you are for the danger, excitement, and opportunity of the unknown.

Granted, our generation has it considerably easier. I haven’t heard of a single startup fail due to dysentery, bear attack, or by falling prey to any of the unimaginable physical hardships our ancestors endured. But I do think those same ancestors would recognize some of the emotional hardships we face on a daily basis. The tremendous personal investment with an entirely uncertain return. The constant skepticism by your peers. The lonely nights working in the dark while other, more sensible folk are comfortably tucked away or out with friends. The trail isn’t as hard as it was. But it’s still pretty hard.

And one of the most difficult times, oddly, is when you stumble out of the swampy woods and into the soft expanse of a fertile valley. Because then you need to decide: do you stop here, or keep going?

Expensify’s path hasn’t been a straight one. We spent forever carefully plotting a course in one direction, only to hit an unfordable river right as we found a tempting tail into the woods. That took us to a steep wall, which we climbed merely because we had no other option. Which took us to another, and then another. There was more than a little hardship along the way.

But it’s taken us to a wide, verdant, entirely unexplored landscape known generally as “expense reports that don’t suck”.

I could rave for ages about how fantastic it is here. Viral dynamics have combined with mobile marketplaces — all enabled by the consumerization of IT — to create a once-only customer acquisition opportunity that looks like it’ll keep accelerating steadily at essentially no cost, forever. We’ve got an unbeatable customer set of business travelers — high spend individuals who spend other peoples’ money. We’ve got a surprisingly small and tight product that addresses the needs of a surprisingly wide set of users. The view from our high mountain pass is fantastic, with easy inroads to many other valleys.

Things are really, really good in the Expensify Valley, and they’re only going to get better.

But do we stop here? That’s the core question. After all, there’s more than enough opportunity to keep us busy for years. Why bother trying to find more?  The answer is: because not all opportunity is created equal.

Yes, things are great, and we’re absolutely going to take care of the many, many users who depend upon us. But we’re not quite ready to settle. Our valley is surrounded by even more interesting opportunitites, extending as far as the eye can see.  There’s gold in them thar hills, and we’re determined to find it.

Basically, I’d say we have the basics down cold.  We’re the clear leader in small business expense reporting, we have a quickly growing userbase, everything is looking up.  But we’ve only got the basics down cold.  It’s time to go beyond the basics and start raising the bar — redefining the state of the art.

Our first move along these lines was our receipt scanning service.  If you haven’t already checked it out, give it a shot — every account starts with ten free scans.  (Invite a friend and you’ll both get five more, or buy them for $0.20 each.)  We’re not even a month into it and it’s already proven to be incredibly popular.  But we’ve got a few others planned, and they just keep getting better.

So things might be quiet for a bit while we settle in to our idyllic valley and set up a permanent camp.  We’ve got a large stack of work in front of us, including massive performance improvements, improved mobile apps, streamlined accounting flows, an so on.  They’ll be trickling out here and there, sticking with our goal of just getting a little better every day.

But one day soon, when you least expect it, something big is going to happen.  And man, I just can’t wait to show you what it is.

Awesome people have more fun working than most pople have playing. It’s because they work hard on things they care about, with people who share their passions. They kill bugs like others catapult birds. They don’t need sudoku because they have SQL. Hard work is naturally fun work, if you’re in the right environment, with the right people.

But work-fun is very different than play-fun, and as surprising as it might sound, when you’re so busy with the former you sometimes forget the latter. If that sounds familiar, my suggestion to you is: Don’t forget to have fun. Play-fun. Schedule it in. Take advantage of it when the opportunity arises. Set aside the deadline for a moment and go do sommething stupid. Your compiler can wait, but once those moments are gone, they’re gone.

This mantra occurred to me recently upon learning of our billboard. Getting a billboard is a long, painful, and expensive process. We debated it forever, discarded countless concepts, payed an enormous deposit… and then forgot about it and got back to work. But then one day, we heard rumor that it was there — and we were having lunch only a few blocks away! We had huge deadlines looming before us and couldn’t reasonably spare the time for a field trip. But you don’t get a second chance at seeing your startup’s first billboard. This is what it was like for us:

Expense reports that don't suck

David Barrett, CEO of Expensify Expense reports that don't suck Expense reports that don't suck

It’s a little thing, perhaps. But I’m glad I was there when we saw our first billboard for the first time. It’s one of those opportunities that only comes once. Don’t forget to have fun, and you won’t ever forget it.