Pathologically Entrepreneurial
Long ago, when I set up this blog I read a few primers on blogging. One of them suggested that you have a picture of yourself on your blog. There were lots of good arguments for doing it, so I dutifully hunted among my photos for a picture of myself. Turns out that I didn’t have too many (I tend to be behind the camera rather than in front of it).

I did find one that I liked. It was on a nasty old fishing boat on the Prince William Sound (in Alaska). A friend of mine had bought the boat and invited a few friends for an multi-day cruise. There was no running water. The bathroom was a 5 gallon green bucket (I’ll leave it to your imagination how we “flushed” it). At the end of the trip, I was scruffy as hell, but I’d had an absolute blast tromping around the rugged islands of Alaska. That’s where the pipe picture was taken.
As my blog actually accumulated readers, there came a trickle of negative feedback about the pipe, which has increased to a steady stream. Some people feel like I was trying to look serious. Or academic. Or rich. Or that I was just clowning around. To me, the photo had a ton of meaning. To anyone else, not so much.
For some reason, this made me think of one of my favorite posts on product/UX design. Here’s a quote:
“When I started working on Wufoo, I was definitely a bad designer. I thought I was hot shit and knew all the answers. I saw the user as a wild beast that needed to be tamed. He got in MY way. Use the tool the way I designed it, fool—not the way you think it should work [emphasis added]. Thinking back, I remember being angry all of the time.”
One of the big lessons (which I continue to learn a little bit more every single day) is that it doesn’t matter a damn bit what you’re saying (whether you’re “saying” it to a user with design or saying it with words or pictures on a blog), it matters what’s being heard.
So I’ve pulled the pipe picture in favor of a more recent one. Some people suggested that I keep it as a “schtick”, but I’d rather be known as “that guy who kicks ass with RescueTime” than “that guy with the pipe” (who actually never smokes a pipe).
One of the frustrating things about iterative software development is that you never get to do a heroic launch (a la Steve Jobs). Your software starts off to be barely good enough for someone to endure. The next week it’s better. Rinse, repeat. If you’re good, someday you wake up and you’ve built great software. We’ve got a long road before this day, but we think we’re onto something.
Anyhoo, hat tip to Web Worker Daily!
They posted a note describing some of the cool new features in RescueTime, including the very first version of RescueTime Groups, which seems damn promising. Give it a look!
[edit: I should probably have made a stronger point that I am talking about early early early stage startups. 2-5 people, pre-funding. Carry on!]
There is a tremendous amount of venom loosed towards so called “business guys” or “idea guys” (as I’ve called ‘em) in the startup community. They can’t catch a break.
A big part of the reason is that we’ve all had that hellish experience with the MBA. The guy who has his “big idea” and “just needs someone to build it”, presumably why he stands back and waves his hands a lot (and occasionally plays golf in space). You can find CraigsList littered with ads by biz guys, incredulous that hackers aren’t falling all over themselves to execute on their ideas.
It doesn’t take a lot of hunting around to learn that great technology startups aren’t generally built on the shoulders of a great business guy. Here’s a gem of a quote from a gem of an essay:
If you work your way down the Forbes 400 making an x next to the name of each person with an MBA, you’ll learn something important about business school. You don’t even hit an MBA till number 22, Phil Knight, the CEO of Nike. There are only four MBAs in the top 50. What you notice in the Forbes 400 are a lot of people with technical backgrounds. Bill Gates, Steve Jobs, Larry Ellison, Michael Dell, Jeff Bezos, Gordon Moore. The rulers of the technology business tend to come from technology, not business. So if you want to invest two years in something that will help you succeed in business, the evidence suggests you’d do better to learn how to hack than get an MBA.
Take a look at the genesis of your favorite startup and find me the MBA. Find me the program manager. They just aren’t there.
So your startup doesn’t need a business guy. In fact, there seems to be pretty compelling evidence that having a business guy in your software startup has a reverse corrolation with success.
So, take a walk, biz guy. We don’t need you.
Or do we?
It turns out that it’s not so simple as that. Startups are diverse– each startup has different needs. How do you think SalesForce.com would’ve done if it’d been started by a bunch of hackers? How do you think Zappos.com would have fared if it wasn’t started by a zealot for customer service and support? There are plenty of examples of great software startups with a critical founder who wasn’t really a technologist (arguably, Apple is a great example of this). And there’s no denying that for startups that have something that they intend to CHARGE for, a business guy is incredibly valuable– so long as he actually can dive in and do sales largely full-time. Most business guys I know turn there nose up at cold-call style sales– which is really what you need.
So what does every startup absolutely need?
Startups need BUILDERS. People who make stuff. Absolute animals, as Paul Graham puts it. People whose output is positively awe-inspiring.
But startups also need a product genius. Someone who has great instincts about what people want and need.
So what’s to stop a business guy from being a product genius? Not a darn thing. Sure, there are plenty of biz guys who are stupid about products, but it certainly doesn’t take much work to find a hacker who has a truly awful idea for a product.
It’s just not so simple.
But I’ll tell you something that is simple: a hacker or designer’s output is strongly correlative with their sense of ownership. Here are a pile of modifiers that can effect a sense of ownership:
In a world where startups are beset with endless challenges and frustration, anything you can do to heap on a feeling of ownership among the people who are actually building stuff is critical.
If there’s any indisputable advantage that startups have over big business, it’s the insane amount of sheer output that a startup can generate. Part of this is just being lean and bureaucracy-free, but a huge part of it is the motivation that comes with a sense of ownership. I think it’s pretty safe to say that the bigger a company gets and the more pure-play “managers” that get hired, the farther away the builders get from this feeling.
For all the startups out there who have a biz guy playing golf in space while a collection of hackers and designers slave away on the idea that they don’t really love…. Well, I don’t think you are necessarily doomed to failure. But I think you’ve taken an uphill road that’s a bit too steep for my tastes.
There’s quite a flap over Paul Graham’s recent essay.
The attacking author quotes a comment on Reddit (always a good sign) as a good summary of the essay of why we should all be terribly offended.
“I work with young startup founders in their twenties. They’re geniuses, and play by their own rules. Oh… you haven’t founded a company? You suck.”
I kinda feel like there is a reading comprehension problem here. Paul added a “Cliff’s Notes” version of the article to clarify, but I’m going to boil down what I got.
The point I got from the essay is:
“I work with young startup founders in their twenties [note: he works with me and a mess of other founders who are also in their thirties… at least 1 or 2 are in their forties]. They seem stressed, but they seem happier and more alive. I think it might be a socio-biological thing– human beings are meant to be working in smaller groups, with clearer goals, and more ‘on the line’. Small businesses and startups seem like the best place to find this environment.”
Period.
Saying stuff like “happier and more alive” (which PG did not– I’m paraphrasing) does not mean that everyone else is miserable and dead inside.
Anyways, this isn’t a wild idea. There are piles of studies out there that have found a correlation between self-employment and satisfaction/happiness. Incidentally, there’s also a strong correlation between self-employment and making less money (but that’s good news, because there are ALSO studies that show that money doesn’t do much for happiness once you manage to have enough coming in to cover the necessities)
I think that common sense goes a long ways in UI design… But not all the way. It’s a learned skill like any other. I was reading up on calendar controls today (which I’m obsessed with, by the way) and caught a great post by the curmudgeonly Jakob Nielsen. Here’s the snippet I like best (he’s describing the top application design mistakes):
“Affordance” means what you can do to an object. For example, a checkbox affords turning on and off, and a slider affords moving up or down. “Perceived affordances” are actions you understand just by looking at the object, before you start using it (or feeling it, if it’s a physical device rather than an on-screen UI element). All of this is discussed in Don Norman’s book The Design of Everyday Things.
Perceived affordances are especially important in UI design, because all screen pixels afford clicking — even though nothing usually happens if you click. There are so many visible things on a computer screen that users don’t have time for a mine sweeping game, clicking around hoping to find something actionable. (Exception: small children sometimes like to explore screens by clicking around.)
Drag-and-drop designs are often the worst offenders when it’s not apparent that something can be dragged or where something can be dropped. (Or what will happen if you do drag or drop.) In contrast, simple checkboxes and command buttons usually make it painfully obvious what you can click.
Common symptoms of the lack of perceived affordances are:
- * Users say, “What do I do here?”
- * Users don’t go near a feature that would help them.
- * A profusion of screen text tries to overcome these two problems. (Even worse are verbose, multi-stage instructions that disappear after you perform the first of several actions.)
When I tested some of the first Macintosh applications in the mid-1980s, users were often stumped by the empty screen that appeared when they launched, say, MacWrite. What do I do here, indeed. The first step was supposed to be to create a new document, but that command was not shown anywhere in the otherwise highly visible Macintosh UI unless you happened to pull down the File menu. Later application releases opened up with a blank document on the screen, complete with an inviting, blinking insertion point that provided the perceived affordance for “start typing.”
This Wednesday, I’ll be participating in a really interesting panel discussion entitled “Silicon Valley Fights Back Against the (Information) Monster it Created”. The panel is moderated by Matt Richtel (New York Times Correspondent). Here’s the description:
Intel launched no email Fridays. So did US Cellular. Some managers at Genentech urge employees to check email only twice a day. The Valley and its denizens are trying to combat a problem of their own making: information overload. Everyone knows the issue. The very tools spurring your productivity are also undermining it. This is not merely a question of personal organization. Information overload is spawning industries. New businesses and new products are being created from the likes of Microsoft and Google, and numerous start-ups, too, to help people manage and mute the cacophony and onslaught of information. The question: what can you do to avoid becoming overwhelmed? Even further, can you capitalize or build or enhance your business around helping others to regain productivity? Or have we created a monster here destined to eat us alive (please forgive the hyperbole…we wrote the end quickly because we have incoming email and need to get to it right away).
- Registration: 06:00 PM
- Buffet: 06:00 PM
- Program: 07:00 PM
Location:
Crowne Plaza Cabana Hotel
4290 El Camino Real
Palo Alto, CA
You can register for the event here. I have two guest invites– so holler if you’d like to go.
Don Norman recently wrote a fine piece entitled “Why is 37Signals So Arrogant?“. As a student of link/click bait, I have to applaud him. Bravo! It’s right up there with Jason Calacanis’ post about firing anyone who isn’t a workaholic (his followup is a bit more measured).
So I’m going to do one better than Don Norman, and tell you exactly why 37Signals is so arrogant.
But, first I’m going to tell you that they’re not. At least not in the way that Norman is saying. 37Signals listens VERY HARD to their users. It’s amazing to note that up until recently (correct me if I’m wrong) Jason Fried read (and sometimes responded to) every single support email. In light of this, to say that 37Signals doesn’t listen to their users is absurd.
Norman and Nielsen have always argued that the best way to understand users is to watch them use your product. I tend to agree- but dealing with support yourself as a product developer is a close second– it’s an amazing way to feel the pain and confusion of your users. Most product developers hire a cheap support staff as soon as they can manage– to get themselves out of the muck. These guys didn’t.
But, come on. Read their blog. Take a look at DHH’s (in)famous “Fuck You” Slide. These guys are clearly arrogant.
Here’s why.
Take a look at the people that most people envy. Hell, start in high school and work your way up. How many times have you said, “why is that girl dating that absolute JERK?” Look at all of the people who are successful in this world and you’ll find a fairly common theme. There is a decided absence of humble and self-deprecating people. There aren’t a lot of people on top who are frequently saying, “I am wrong and you are right”.
So it’s easy to say that as software geeks we are above that. We grew up on the wrong end of “nice guys finish last” and we’re going to be bigger than that. But look at the giants of our world. Steve Jobs. Linus Torvalds. Paul Graham. Joel Spolsky. Bill Gates. Jakob Neilsen. There are certainly degrees of it in this collection of stars, but every single one of them speaks and acts with near-absolute assurance and authority. They embrace controversy and sometimes provoke it. Every single one of ‘em has been called arrogant.
As masters of marketing, the fellas at 37Signals are (either consciously or unconsciously) lumping themselves in with the guys at the top of the food chain. They are the high school equivalent of the insensitive guy in the letterman’s jacket who always gets the girl. They are talking the talk, stirring the pot, saying surprising things, pissing people off, and daring the world to prove them wrong.
You might not like them, but you’re looking at them and listening to them– which is more than you can say for the thousands of other 10-person profitable software companies out there.
I would like to finish by saying that I’m better than you. I’m right. You’re wrong. My [insert language/platform/dev tool] is better than your [insert language/platform/dev tool].
Thanks for listening.
Well, not all of it. That title was blatant click-bait. You’re here and I’ve won. Nyah!
I’ve long been passionate about reading and digesting every tidbit of information about what it takes to build a successful startup. I’m an avid reader of people like Seth Godin, Paul Graham, Guy Kawasaki, the fellas at VentureHacks, Fred Wilson, Josh Kopelman, Andrew Chen, and more. As a participant in the YCombinator program, I have weekly dinners with entrepreneurs who have “hit it big” (Marc Andreessen, Ev Williams, Paul Buchheit, Chris Sacca, & Joe Kraus, to name a few).
All of the things I’ve learned are incredibly useful and all of it (paradoxically) can be incredibly wrong.
Let me explain my thinking here. Human beings love formulas. Human beings who succeed naturally think that they’ve stumbled onto a magical step-by-step guide on how other people can succeed, too. They blog about it, speak about it, and generally spread their wisdom far and wide.
The funny thing is that when you read/hear enough of this stuff, you start hearing brilliant and successful people presenting advice that directly conflicts with the advice from other brilliant and successful people.
Here are a few examples:
The list goes on. Find me a startup truism and I’ll find you a successful startup which is a living and breathing counter-example. All of the advice that you read and hear is incredibly valuable– but it’s very situational. Add it to your “startup utility belt” and whip it out when you hit a bump in the road that looks familiar. “Andreessen ran into this and solved the problem thusly. That’s what I’ll try!” But don’t think that you can arm yourself with a list of platitudes and expect to build a startup.
The Two Truisms that Aren’t Lies
Now that I’ve finished saying that there’s no formula, I’m going to give you the two pieces of advice that (near as I can tell) EVERY successful founder has followed. Zero exceptions.
I can’t think of a single startup that has died from an over-emphasis on these two points. Can you?
Someone posted an interesting “Ask YC”, asking:
“How to start becoming an entrepreneur while still being an employee?”
Having done this twice (started a company that eventually turned into a full-time startup), I settled in to reply. Before long, it was clear that my response was long enough to justify a blog post.
I’ve done two part-time-to-full-time startups (one resulted in a startup the sold, the second is RescueTime– currently a YC-funded company– cross your fingers).
At the end of the day, I think Paul Graham is right when he says:
“The number one thing not to do is other things. If you find yourself saying a sentence that ends with “but we’re going to keep working on the startup,” you are in big trouble. Bob’s going to grad school, but we’re going to keep working on the startup. We’re moving back to Minnesota, but we’re going to keep working on the startup. We’re taking on some consulting projects, but we’re going to keep working on the startup. You may as well just translate these to “we’re giving up on the startup, but we’re not willing to admit that to ourselves,” because that’s what it means most of the time. A startup is so hard that working on it can’t be preceded by “but.”"
In the beginning, however, it’s not always practical to dive in full-time. And sometimes when your idea is off-the-wall and also easy to build a prototype for, it’s smart to whip something out just to see if what you’re building is as cool as you think it might be before you take the plunge.
So if you’re too poor or too unsure to do the right thing for your business and dive in full-time, here are a few things that seemed to work for us when we did it part-time:
At the end of the day, you want to prove whatever you need to prove as quickly as possible, so you can dive in full-time. Near as I can tell, there are plenty of startups that have started as “hobbies”, but you need to take it out of that phase as soon as you can. There is nothing that drives a team forward like the fear of public failure, debt, and starvation. Leap off the cliff and start building the airplane on the way down and you might be surprised with what you can pull off.