Software Dev

Entrepreneurship and Youth

May 22

There has been some interesting discussion of late about the relationship between youth and successful entrepreneurship. It started with a from-the-hip post by Fred Wilson (which he later elaborated on).

After looking at the chart posted on Valleywag, it got me wondering about how old a fella has to be before he ought to get out of the business of startups.

After reading Fred’s musings and the (damn insightful) blog entry by Clay Shirky, I feel (at the ripe ol’ age of 35) less anxious about the whole thing. Of course, I might just be feeling young because I took the last couple of days off to pal around with my 70 year old father.

Clay states:

I’m old enough to know a lot of things, just from life experience. I know that music comes from stores. I know that you have to try on pants before you buy them. I know that newspapers are where you get your political news and how you look for a job. I know that if you want to have a conversation with someone, you call them on the phone. I know that the library is the most important building on a college campus. I know that if you need to take a trip, you visit a travel agent.

In the last 15 years or so, I’ve had to unlearn every one of those things and a million others. This makes me a not-bad analyst, because I have to explain new technology to myself first — I’m too old to understand it natively. But it makes me a lousy entrepreneur.

“A Lot of Knowledge Is A Dangerous Thing”

One thing that struck me about the “unlearnings” that Clay brings up is that they are pretty idea-centric. That is to say, these are the sort of learnings that could keep you, as an entrepreneur, from hitting upon the “big idea”. As I’ve mentioned before (liberally quoting from folks who are smarter than I am), ideas aren’t necessarily in short supply. While I’m sure many startups fail for lack of a good idea, I’d wager the majority fail from poor execution. Methodologies, strategies, and staffing levels that work at Fortune 500 companies simply don’t fly in a small company. The careful modeling, planning, and PowerPoint wrangling that you learn in business school really isn’t a great way to invest your time when your business model might need to change dramatically in a month or two. And I’d wager that the more experienced you are (and the more confident you are in your hard-won wisdom), the less likely you’re going to be able to adapt to working in a small business environment.

I want to explore this a bit more, but (given that I’m buried under a pile of email) it’ll have to wait for another blog post.

5 Reasons you don’t want to partner with an “Idea Guy”

May 17

(apologies for the lack of gender neutrality in this entry– idea girls exist too…)

I had a colleague the other day refer to me as an “idea guy”. I’m sure they meant it as a compliment, but I winced when I heard it. As a guy who tends to lurk in entrepreneurial circles, I often run into self-identified “idea guys” (usually, they are in “stealth mode”, which I generally find similarly ridiculous)– and virtually every time I do, I tend to walk away shaking my head. Here are 5 quick reasons why your startup doesn’t need an “idea guy”:

1. Everyone is an idea guy. Well, strictly speaking, that’s not the case. I’ve met plenty of folks who aren’t interested (or aren’t good at) the strategy and tactics of software/product development. There are plenty of engineers out there who just want interested technology to fiddle with and couldn’t care less what the grand plan is. There are plenty of designers who just want a good set of design specs so they can make pretty pictures or highly usable prototypes. There are plenty of salesfolks who don’t give a darn what they are selling. So what makes an idea guy an idea guy? Usually it’s the simple fact that they don’t have any other skills to bring to the startup.

2. By virtue of the fact that they consider themselves an idea guy, it quite likely means that they are convinced that their ideas are better than yours (or anyone elses). Of course they are! They are an idea guy! The big problem with this is that startup ideas need to change… Very few startups stick with the exact same idea. How excited is an idea guy going to be about shifting to a new idea that he didn’t generate? Not very exited, as it turns out.

3. Ideas are relatively valueless… because smart people say so. Don’t believe me? Here’s what Paul Graham has to say (though I think the argument about the “sellability” of ideas is pretty weak). Don’t believe Paul? How about Guy Kawasaki? One one my favorite quotes from Guy when he was asked how an entrepreneur could keep their idea from being stolen. His response was “”You could discuss it with no investors, show it to no customers and never hire employees….” (see it in context).

As a test, approach a dozen venture capitalists. Explain that your primary skillset is “idea generation”. Do your best to defend this and give copious examples of your genius. Go home and wait for the phone to ring.

4. Ideas aren’t defensible. Google “First Mover advantage” and you can find all sorts of people debunking that particular myth. Google moved into an established market and clobbered it. Ipods certainly weren’t the first MP3 player. Dodgeball lost out to Twitter. Friendster was sucker-punched by Facebook and MySpace. The first movers spend tremendous amounts of money educating the market and making all sorts of stupid mistakes and the second movers come in when the market is primed and make it look easy.

5. In startup businesses, idea guys run out of things to do pretty quickly. There’s no room in a startup organization for someone to sit around and spew out ideas. Startups need builders, whether you’re building software, hardware, visual interfaces, teams, bank accounts, or audiences. If you’re a founder, you probably need to be good at more than one of these things.

Despite the evidence to the contrary, I feel like every day I run into founder and consultants who think having a million dollar idea is enough to bring to the table. Most of the time, I think this is because they haven’t the faintest clue how hard it is to turn a great idea into a great product or service.

“Get in, Get it, Get Out”

May 14

Just read a great article on BBC by way of Slashdot about Web 2.0 (tip o’ the hat to Brian Fioca, who IM’ed me the link) It liberally quotes usability-zealot Jakob Nielsen who, as you can imagine, is not all that enamored with the Web 2.0 movement.

As usual, someone more famous than me summarizes some of my thoughts better than I’m capable of.

What I find strange about Web 2.0 is that we web geeks are losing sight of the fact that the vast majority of people use the internet as a tool. They want information. They want pictures. They want music. They want to buy stuff. They want to search for jobs.

But do they really want to socialize online, just for the sake of socializing?

Certainly teenagers do. I suppose I would too if I had a job that was 8am-3pm, had virtually no responsibilities, and had 16 weeks of vacation time.

There’s a great new study out that says:

15% of Americans don’t have an internet connection
10% view the Internet as a “hassle” (probably because ever site is trying to get them to join their community)
About 50% of the population “doesn’t use the internet very much. I’d presume that when they DO use it, they use it as a utility.

To me, the most exciting startups are those that solve problems. That provide a transactional product or service. That, in the words of Nielsen, allow users to “get in, get it, get out”.

I tend to be suspicious of businesses that are trying to create an online “community”. You can certainly build a successful business by doing so. But I think online communities are extremely challenging to build, and they tend to turn off the much-more-massive audience that Nielsen talks about. Amazon would be a LOT less easy to use if they were constantly bombarding me with community features.

Look at LinkedIn. They’ve been around since 2002. They’ve gotten over 28 million in VC and they have a tremendously viral service (WAY before it was cool to be viral!). They are the poster child for social networking for grownups. Yet they’ve only managed to collect 9 million accounts in 5 years (and I’d wager than only a fraction of those are active given that it’s nigh impossible to delete a LinkedIn account).

To this day, I still hear people ask, “So what can you DO on LinkedIn?” I’m hard-pressed to give an answer.

At the end of the day, there seems to be a pretty finite number of adults for whom social networking is at all relevant. And there’s a huge pile of sites that are vying for the attention of these busy users. I’d wager that the only ones who are going to succeed (on a grand scale) are also going to allow the other 90% of the internet audience to “get in, get it, and get out”.

Linebuzz Starts Humming

May 07

Jobster alumnus Mark Maunder has put his travel blogging startup on hold for a month or two to pursue his muse… Which, in this case is (drumroll please) inline blog comments! It would be irresponsible of me not to mention Mark’s wife and biz partner, Kerry– who is quite likely the only reason that this thing has gotten off the launch pad…. Kerry is a seasoned QA manager and has almost certainly kept this thing from being a bug-ridden pile o’ PERL code.

It’s in “soft-launch” phase and they are working out a few kinks, but I think it’s a pretty exciting idea. So try it out here, head over to Linebuzz.com and bury Mark and Kerry in feedback and bug reports.

9 Reasons why Web Software Teams get Too Big

Apr 28

Before I got involved with product development a few years ago, my entire career was spent owning and running a small (10-20) person web app consulting firm. Clients (ranging from mom-and-pop operations to Fortune 100 megacorps) would come to me with a problem and I would assemble a team to solve that problem with some sort of web application. 99% of the time, the size of that team was somewhere between 1 and 4 consultants.

When I started a little Web 2.0 company, it seemed natural to keep the team to 2 people, with me doing some design, PR, marketing, and biz related stuff, and Brian doing the assorted geekery required to make a web app go (server and client side coding and a bit o’ sysadmin work).

When our little company got bought by Jobster and we relocated to Seattle, one of the things that truly blew me away was the SIZE of the product development operation at what most Jobsterites felt was a lean operation. There were literally dozens of developers, a few designers, a mess of program managers, and a small army of offshore QA folks. I don’t have the exact count, but I think that somewhere in the neighborhood of 35 people could honestly say, “My job is to build software” at Jobster.

So why the discrepancy? The little teams that I had worked on for most of my life weren’t solving tiny problems. Sure, we had an occasional brochure-ware client, but a big slice of our time was build applications that were pretty darn complex and sophisticated. There are two very legitimate reasons that software teams get big:

First off, some web software is just big/complex/ugly… and it has to be. Enterprise software tends to be bigger, more complex, and have lots of integration points which get pretty complicated. The “two guys in a garage” theory doesn’t really work for such things. The more I play in the world of web development, the more adamant I am about not wanted to play in the world of “big” software. Big projects might have merit, but they are certainly a helluva lot less fun.
Some teams are really a bunch of smaller teams working on different things. Jobster was (and is!) definitely engaged in several different initiatives. So the team of 35 people were really (depending on how you slice it) working on two or three very different problems.

Unfortunately, the list of reasons for team bloat goes on and it gets pretty ugly (note: some of these are paraphrased from Parkinson’s Law)

People make work for each other. Certain people are REALLY good at creating LOTS of work for other people. Some of this work is valuable and productive, but much of it (excess documentation, “here’s what I’m up to” meetings, etc) is not.
The amount of work on a team ebbs and flows. Sometimes there’s a ton of work, and an undisciplined (or over-funded) team will seek to get bigger rather than just suffering through the peaks.
People like subordinates. Oftentimes, a manager is measured by the size of their team. Bigger teams mean bigger budgets and more responsibility, and that looks good on a resume.
Work, like water, spreads out and seeks to fill the nooks and crannies of an organization. If a 10 hour task for one person spreads around to involve 4 other people, it’s likely that the manpower spent on the task will explode to something well beyond 10 hours.
An individual’s tasks will expand to fill the time alloted to accomplish them. This seems like the other side of the “necessity is the motherhood of invention” truism. In the times where people have more time than they need to accomplish a task, they’ll find a way to stretch it out. This includes surfing the web or (much more dangerous) adding complexity/oversight to the processes involved in completing the task (creating a longer term “bloat”).
Communication paths grow exponentially with the size of the organization. With two people, there is exactly two possible communication directions. With a team of 10 people I have 9 other people that I have to communicate with (and who have to communicate with me). This dramatically increases the chance of miscommunication, confusion, excessive questions/clarifications, and (everyone’s favorite) office politics.
Low quality team members can hide in the herd. If a team member loses their motivation in a two person team, it becomes pretty evident pretty quickly. On large teams, low-productivity members can lurk for months without any problems.

Of course, there is some value in larger teams. And, in my opinion, there is simply HUGE value in growing your team from 1 to 2. Two brains are most certainly more than twice as sharp as one. Beyond a team of two or three, however, I think that the added manpower offers asymptotically diminishing returns. While I truly believe in the Wisdom of Crowds, I think the best way to harness this wisdom in software development is by collecting thoughts and opinions in a one-off kind of way (usability tests, focus groups, consultants and the cheaper alternatives of asking peers, friends and family for their opinions).