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I collaborate with lots of different teams, and collaboration often involves project management software. I myself am a Basecamp junkie, but when I suggest Basecamp or ask others why they do not use the application I frequently get responses ranging from the relatively benign “Basecamp does not do what we need” all the way to the snarky “Basecamp sucks.” I always find these appraisals of Basecamp curious. I typically make a small sales pitch for Basecamp and then back off, assuming that I might learn something new by collaborating with a different tool. Sadly, I never learn anything new. Every small team I work with uses project management software in the same way: as one big to-do list. So, in my experience, the debate is not about features.

At its core Basecamp is just a fancy to-do list tool. But the folks at Basecamp have done a world-class job of building an amazing application. Adding, assigning, and communicating about tasks is fast, easy, and enjoyable. Basecamp messages are never lost and it is very clear if someone is waiting for you to complete a task. Too often other project management software products on the market fail to achieve the same objectives. As a result, they can be more of an annoyance than a tool.

This post is not a review of Basecamp. What I find so interesting is this: Why isn’t Basecamp used by more of my colleagues? My theory is that Basecamp suffers from “blank canvas” syndrome. When you first create your Basecamp account there is no predefined way to organize your projects. You have an empty window waiting for you to create to-do lists. You have to decide with your team how to use Basecamp. Other project management tools tend to guide you into their way of organizing a project. Being guided is good for getting off the ground—but can be bad for long-term satisfaction with a product.


What is a good seat in this fast-moving business environment? Traditionally, our first thought would be the cozy corner office far away from those bright, naked cubicles by reception. But this is the 21st century and peace of mind is dictated more by solving problems and being productive than creature comforts like a quiet environment or a pleasant view—or even the freedom of a virtual office. No, the “good seat” in business is about managing technology and personnel needs. And that can be done from either side of the hypothetical desk.

Whether you are performing the job or having someone perform it for you does not matter. The important thing is understanding the big picture of what it takes to get the job done. Make sure you have a contract that clearly defines the scope of work, the infrastructure necessary for success, and the procedures for resolving problems. Not understanding the business model and its processes will put you in a no?win situation. Does the upgrade require new hardware or software? What does the maintenance phase look like? Who has control over the data? Will the budget be enough to see the project from start to finish? You don’t want to go in half?assed because cutting corners simply won’t get the job done. No, you are going to need to be fully assed to sit in that seat over the long haul.


So you have a fresh new idea for a product. Maybe an iPhone app, a web application, whatever. You saved up some money or wangled some investors, but instead of hiring a team to develop your project you want to subcontract out to an agency. Your thinking is that the agency can get your product to market swiftly as they have in house all of the designers and developers needed to build your dream.

In the last 15 years I have hired many agencies. I have also worked for many agencies. Heck, I even ran an agency. Let’s say I’ve seen the agency issue from all sides. So I wrote this post to share a few things to keep in mind when going the agency route. Most also apply to hiring a freelance designer or developer, but the focus is agencies—the types of companies that have fancy offices, charge boatloads per hour, and invite 25 people to every meeting (account managers, project managers, salespeople, developers, designers, freelancers, random dude not doing anything that day).

You Can’t Have It All

When hiring an agency you can’t expect to get a high-quality product at a good price delivered on a fixed schedule. An agency salesperson will always try to convince you that they can deliver on your schedule. If they are working on an hourly basis they will assure you that they “already added tons of padding to the budget.” And besides, their designers and developers are the best in the world! Simply accepting that you can’t have an outcome where quality, budget, and schedule are achieved you should maximize for one or two. Don’t be fooled into thinking you can have it all.

Most Agencies Don’t Care About Your Little Project

The best agencies spend their days working with the big boys, the Fortune 500. These clients have massive budgets and are a good agency’s bread and butter. Simply put, your little startup project is not going to get the best resources or the most attention. An agency will always choose a Fortune 500 client over you. Sorry.

Agencies Hire Lots of Freelancers

Agencies rely on freelancers to save money. They pay some eager freelancer $50 an hour (no benefits, no taxes) and bill them out for $150 an hour. The problem with these subcontractors is that they come and go—in some cases halfway through a project. Transferring knowledge from one person to another is costly, jeopardizes the schedule, and can negatively impact quality. Agency turnover can make you wonder if you should have just hired a freelancer yourself.

Your best bet is to make sure your agency is not going to subcontract out your project. If it’s unavoidable, be sure that your contract details what happens if things go wrong with the subcontractor. Also, confirm that an agency employee will manage the project. I have seen it happen over and over again: the agency hires a subcontractor for your project, puts you in contact with said subcontractor, and then takes a backseat. Dumping project management on the client is pure negligence on the part of the agency. (I doubt that it happens with their Fortune 500 clients.)


Ah, feedback. Life is unbearable if you cannot speak your mind, but in our everyone’s-a-winner culture anything short of ebullient praise is viewed as an affront. And so, to show that you’re not a glass-half-empty sort—you see the positive stuff, too!—you start with a few compliments before slipping in the unpleasant news. But you don’t want to end on a bad note so you close with something upbeat—another compliment or some hearty encouragement. Congratulations. You just served a “shit sandwich.” In more refined circles it’s called a “praise sandwich.” Either way, it’s a classic rookie mistake. Your protégé will take one look at this questionable offering and either see only the praise or only the criticism. You end up with the status quo or a new enemy.

(And in these wild and wooly times you don’t want an enemy. Best case: low-level passive aggressive retribution. Worst case: a digital smear campaign against you—that inexplicably goes viral. But I digress…) Negative feedback is not more palatable when it is preceded by a warm fuzzy: “You did a great job, really. But you don’t seem to understand the concept of a budget.” Even worse is verbally teeing up with a qualifier calculated to (a) distance yourself from the turd (“I hate to tell you, but…”), which often sounds disingenuous or (b) manage the response (“Don’t freak out, but…”), which usually has the opposite effect. Rather than feel gently enlightened, the recipient of your mixed message will either be confused or think you’re an asshole.


Risk Taking Over the course of my career I have had the good fortune of working with many innovative business partners. Regrettably, some partnerships ended poorly because my temper got the best of me. For years I was convinced that I did not get along well with others. But recently, upon deeper reflection, I concluded that something else was to blame because I have many great business relationships that have endured the test of time. So what sets me off? What makes a partnership toxic for me? In a nutshell: risk takers. I do not like taking risks. It’s not my style, and I can’t relate to it.

A scan of the entrepreneurial landscape suggests two fundamental types: risk takers and small bettors. Apple (under Steve Jobs), for example, took large risks—betting the company many times over. In contrast, Twitter has few big bets in its history (heck, it started as a side project), growing instead through iteration—one small bet at a time. Because both forms of entrepreneurship can lead to success, the question of which is better is settled by your tolerance for risk. I prefer to make a small bet, analyze the results, and build on that effort because it is the more risk-averse approach to growing a company.

When forming a business partnership make sure your entrepreneurial styles align. Compatibility with respect to risk can help you avoid painful and costly conflict down the road. Maybe take a trip to Vegas together: if your partner is sitting at the blackjack table the entire time while you sip fancy drinks by the pool, maybe you're not a good match.


There is a trap I have fallen into more times in my career than I would like to admit. I tend to stay too focused on the technology because that is what I know and am passionate about. The thing is, there’s more to a successful digital startup than the technology. For illustration purposes, let’s say I come up with a great idea for a service that will really help me and possibly others: a social network for dogs called DogBook. As a technologist I can pretty easily map out the digital design and development processes that need to happen to launch the service. But in the case of a social network for dogs technology is not the real challenge—marketing is.

That’s right. Getting the attention of possible users in a cost-effective way is the real nut to crack. I hate to break it to you, but if you build it they still might not come. All good startups set out to solve a problem. But when deciding whether to chase an idea it’s important to determine if the core challenge is technology or marketing. For example, in the case of Google the biggest hurdle was technology: building a badass search engine. In the case of DogBook, the difference between success and failure is marketing: customers need to be aware that DogBook exists and is awesome.


I have been working since age 12. An almost daily occurrence since my first day of work is that I screw up. I am human, just like most of you, and all humans make mistakes. What distinguishes good entrepreneurs, good employees, and good people is how we handle our screw-ups. Clearly, all screw-ups are not created equal. They can be as minor as showing up a few minutes late for a meeting or taking longer than necessary to respond to a customer—or as major as blowing a deadline or delivering the wrong product. But because screw-ups are about as inevitable as death and taxes, in business the most important thing is not what happened but what happens next. That is, owning up to the mistake and making it right.

All my professional life I have offered, as a matter of course, some kind of restitution when I screw up. As a consultant, if there is an issue with a deliverable I often lower my price or don’t bill at all. As a service provider, if I am not timely answering a support request I often credit the customer’s account with a few months of free service. It simply never occurred to me not to compensate a customer negatively impacted by a mistake I made. Only recently did it truly soak in that other professionals do not necessarily live by the same code. Over the past few months the employees of some companies I have been doing business with let me down by screwing up repeatedly. Oftentimes, when confronted, they owned up but offered nothing in return to make up for my losses. Not compensating for a significant mistake borders on dishonest.


Long EmailsMost people hate receiving long emails. In fact, some people think emails should be no more than 3 lines long (or 2, or 4, or 5). This is not my personal style. I like to give recipients everything they need in one email. I believe that doing so optimizes my time and theirs. One of two things happen when I send a long, detailed email to someone: either they never read it and drop off or they appreciate having all of the pertinent information in a single reference document. Either way, it amounts to one focused episode in my life versus scattered smaller ones.

Let’s look at the first case in which the recipient never reads my email. Maybe this person is a contractor, vendor, employee, friend looking for advice, or my mom :). If the person is not detail oriented enough to read and process my long email (my nice way of saying they are lazy), then they simply are not a good fit for me in terms of communication style (sorry, mom). And, most likely, working together is not in our best interest. In the case of friends or relatives seeking my advice, many simply move on and get the advice elsewhere if a long reply is too much of a hurdle for them. Simply put, long emails can serve to weed out lazy and needy people—a real time saver in the long run.

In the second case, in which the recipient of a lengthy email is appreciative, the flow of information is optimized to reduce the likelihood of lots of back and forth dialogue. This is a good thing because the fragmented nature of lengthy email exchanges makes them hard to follow and too often results in offhandedness. Providing a single, thoroughly informative document to which the recipient can refer as needed is much more efficient.


The first phone app I ever downloaded was Magic 8 Ball. Technically, the app is called Fortune Ball for trademark reasons, but the ersatz legalistic name does not obscure its identity. (Just as a freezer pop is a popsicle and sparkling wine is champagne, trademark and terroir issues be damned.) I was thrilled to have a digital Magic 8 Ball to help me make decisions, in no small part because it is much more portable than its analog cousin.

Magic 8 Ball had been a trusted guide of mine since childhood. My older sister had one that I borrowed when she was not around. I became enthralled and decided that she did not appreciate its true value, so I neglected to return it. In its physical form the Magic 8 Ball invited contemplation. It had the heft of a scaled-down bowling ball and the gravitas of its dark horse namesake and was filled with a mysterious liquid that concealed the answer on the icosahedral die until it floated into view in the circular window.

That Magic 8 Ball was eventually dropped one too many times, developing a crack and losing an alarming quantity of its inky lifeblood—which led to its confiscation by my mother. I didn’t buy or pilfer a replacement, but its power as a decision-making tool stayed with me. And then, years later, some magical thinking programmers developed the Fortune Ball. The app lacks the comforting solidity of the original, but it is surprisingly satisfying as so many physical things that we once believed could not be replaced digitally are. (Not that long ago I couldn’t imagine buying shoes online. I now buy shoes online almost exclusively. Sorry, shoe stores.)


Before we investigate this thought-provoking claim, let’s do a quick review. Conventional wisdom holds that the fundamental difference between business to business (B2B) and business to consumer (B2C) sales is the purchaser. Furthermore, although in both cases the marketing goal is to guide customers through the purchasing process, the tactics employed with businesses and consumers differ significantly. But things change, and the line between B2B and B2C is blurring.

Traditionally, B2B has been associated with old school sales techniques. Think dealmaking between a salesperson and a business representative—over golf and martinis, maybe. In contrast, B2C entails advertising across a variety of media to cultivate brand awareness and loyalty among individual consumers. Making the B2C sale has historically involved retailers and salespeople—but in many situations these intermediaries are fast becoming relics of the past. (So is the 3-martini lunch.) Social media and the troves of information available online now empower consumers to become well informed before making purchases. They are also more comfortable with—sometimes preferring—a self-directed role in transactions. Think self-service. At home in your pajamas at midnight, if you like.

In recent years B2B has begun to look a lot more like B2C. Although Skyclerk, Cloudmanic’s bookkeeping application for small businesses, is essentially a B2B product, we do not have dedicated salespeople. Instead, we market the product in the very same ways we would a consumer product. We use mobile apps stores, social networks, and online promotion to bring attention to Skyclerk and acquire customers. The product itself is our golf-playing salesperson—meaning it has to be designed to effectively sell itself.