Use Short URLs Without Losing the SEO Juice!

Ok, this post is going to get a little technical. It’s even going to include some open source code, which if you’re so inclined, you can use under the Creative Commons Public License. But before I bore you with the techical details, let’s talk a little about some interesting product trends that have really taken off lately, and why, if you’re not careful, you could end up shooting yourself in the foot.

Short URLs worth $46 Million?

You already know I’m a big fan of Twitter. Well, one of the interesting side effects of the rise of twitter is there has been a comparable rise in the use of URL shortening services like TinyURL. In fact the recent news that raised a $2million A round suggests that venture money is even taking notice of these services. TechCrunch recently speculated that TinyURL, the dominant player in this space, could be worth as much as $46million dollars.

Why are services like TinyURL getting so much attention? Well, since Twitter limits posts to 140 characters, most users try to save as much space for content as they can, by using URL shortening services for any embedded links. Twitter will even automatically use TinyURL if your tweet includes long URLs.

Worth more, BUT Worthless for SEO

The problem with using these services is that your domain loses the SEO juice normally associated with inbound links. While it’s true that most links on Twitter pages are tagged as “nofollow” which limits their SEO power somewhat, one thing is certain, an link to or or any other url shortening service will never give you SEO juice. However, if you could include shortened url links to your own domain you have an opportunity to have that link copied and pasted around the internet giving you direct traffic and SEO link power to your domain.

So, hopefully I’ve convinced you that you don’t want to continue to give away links to generic URL shortening services, and you’re ready to tackle making your own URL shortener. Here’s where we’ll get a little more technical. If you’re not a developer, then have no fear, just take notes and send your dev team to come read the article and add url shortening to your product road map.

How to Build a URL Shortening Service

Developers, let’s talk design for a second. Assuming your building out your own web property and you’ve done some integration with Twitter, Facebook, or other social networking platforms, then you’re probably already familiar with the APIs available from services like TinyURL to post URLs and get back shortened forms.

These services have a much more challenging problem then you do. They need to shorten URLs from an infinite number of domains, and more importantly they need to support arbitrary resources from those domains. Granted, its not too hard to implement a solution for this, you can basically hash the URL into a sufficiently sparce id space and get a unique idenitfier for each URL. A truncated MD5 hash is probably a good solution. Then store the hash in a database, and whenever someone requests the shortened URL you can do a lookup and return the correct long URL from the database.

There are some great services out there that have taken this idea to the next level, and even include analytics, click through tracking, toolbars that frame the content and allow comments, bells and whistles galore. But what they make up from is splash they sacrafice in SEO juice and direct references to your domain. And so you’ll want a solution you can host off your domain.


In all likelihood, you’re content is probably database driven already, and so each potential URL is probably already associated with some unique asset ID. So instead of implementing a one-way database based solution that maps arbitrary URLs into short URLs, you could implement a solution that maps your asset IDs into short URLs.

For example, let’s say you wanted to do this for a WordPress blog, or even a WordPressMU blog network. Since is based on the WordPressMU core, we developed a solution that allows us to map any blog post in our network onto a shortened URL in our domain.

Our goal was to implement a solution that wouldn’t require a new database table mapping between short and long URLs.  We wanted a two way programatic solution, so that we could map to and from shortened andlong URLs with only the characters of the URL. Since we already had asset IDs to work with (in this case a blog_id and a post_id) we could map those IDs into a compressed form like a base46 encoding.

base46, You mean base64? No, actually base35!

What do I mean by base 46? Well imagine a numerical set that is made up of all the digits 0-9, all of the alpha characters a-z, and the 10 URL safe characters: “$-_.!*’(),” allowed by RFC 1738 (the URL spec). If you used those characters as digits for your encoding, then you’d have 46 characters to work with, and you’d be able to encode your asset IDs in base 46. It’s a pretty good system as, the asset ID 9,999,999,999 would be shortened to “f’*ip21″ and so most platforms could save a lot of space on URLs.

There are a couple of gotchas though. First of all, you might want to think about what happens when an asset ID like 1973507, 60546, or 2861642 randomly pops up and your encoded url ends up with words that might be considered offensive. I’ll go ahead and let you figure out what those IDs would encode into, but suffice to say, we wanted to protect against that. One solution, which we ended up choosing, is to simply remove the vowels from the allowed character set. It’s pretty hard to come up with randomly generated dirty words if you have no vowels to work with.

The second problem you might notice is that even though $-_.!*’() and , are allowed in URLs, they are rarely used and as such both Twitter and Facebook get confused when they see these characters in a web url, and they will truncate the link at the character that confuses them. Through testing we determined that ‘-’ ‘_’ and ‘.’ are really the only special characters that Twitter and Facebook allow in URLs.

So, if you just use the digits, the consonants, and the characters ‘-’ ‘_’ and ‘.’, you end up with 35 characters to work with. And as a result, you can encode your asset IDs in base 35. Now, 9,999,999,999 becomes “sb5.fh5″, which is still pretty short, and certainly moves you toward your URL shortening goal!

Quit Your Jibber Jabber, Give Me Some Code, Fool!

Ok, ok, so here’s a link to a WordPressMu plugin that will do URL shortening in base35. There are a couple important caveats. First of all, it’s only designed to work in WordPressMU, not WordPress. Second, it’s only designed to work in WPmu running in VHOST mode. And finally, this code is licensed under the Create Commons, Attribution-NonCommercial-ShareAlike 3.0 Unported, license, and so what that means is that you are free to use this for non-commercial purposes under the following restrictions: you must attribute the work in the manner specified by the licensor, you may not use this work for commercial purposes, if you alter, transform, or build upon this work, you may distribute  the resulting work only under the same or similar license to this one,  and for any reuse or distribution, you must make clear to others the license terms of this work.

The code is pretty self explanatory, but it’s also got tons of comments. Out of the box it will trap and redirect any shortened URLs that reach your server. In order to encode long URLs into shorter ones, you should can call either kmxt_url_to_shorturl($url) or kmxt_shorturl_from_ids($blog_id,$post_id) from somewhere else in your WordPress code. For example, if you’ve implemented a twitter auto-tweeting plugin, you could replace your calls to TinyURL with a call to this shortener.

Good luck and Happy URL Shortening!

Would a Website by any other Domain Name, Still Smell as Sweet?

I was recently approached by a friend who has an interesting idea for a new business. He wanted to pick my brain about what domain name he should buy to best position himself for search engine optimization. I won’t tell you his business idea, but suffice to say that a key strategy for his business will be to compete effectively on SEO. Hint: that probably should be a key part of anyone’s business strategy these days!

The good news for him is that the market he’s going after has very nice long tail characteristics, and no estabilished players. So he’s got a real shot at growing a nice little side business with some well optimized pages and an obvious monetization strategy.

But he’s a guy with brand marketing experience, and so the list of names he wanted to bounce off me had a very “brand” feel to them. He was thinking about the logo and the corporate mission statement and the feel good intagibles that a brand name leaves with a consumer.

After quickly looking through his list I asked him a really simple question: ”Have you checked out any domains that might have built in SEO strength already?”… ”What?” he said… “What are you talking about?”

If you don’t already have an account with, you either need to get one, or you need to make friends with someone who has one. SEOMoz has the most amazing set of tools for really analyzing what you’re doing right or wrong with SEO. I’m not going to tell you I’m an expert at SEO, heck, I make plenty of mistakes, but I can tell you that SEOMoz’s tools are some of the easiest and clearest tools to use, and they’re great for telling me about the mistake I make, so I can go fix them.

If you are considering building a site that has a long tail SEO strategy to it, then you have to check out SEOMoz’s Trifecta tool. One of the ways to use this tool is to ask the question: all else being equal, where does “this domain” rank from a raw SEO potential. One great way to use this would be to compair two potential domains against each other.

My buddies business isn’t trading cards, but I’ll use that market as an example. Let’s say my buddy had come up with the domain name Sounds like a reasonable name right? It’s got some good key words in the domain, it might be a little long, but hey, he could buy it and start rolling.

Instead, let’s take a look at DMOZ, for those of you who haven’t heard of it is an open directory of websites. It was orginally designed by the open source community as a competitor to Yahoo’s directory of sites. It was a great idea at the time, but unfortunately it’s become very difficult to get any sites listed in it.

The bad news is, your new site is not likely to get listed. The good news is, that if you can pick up a site that is already listed, then you get the trust benefit that comes from being listed in DMOZ. Trust me, this is SEO gold.

After checking out DMOZ for a couple minutes, I’ve found two interesting candidates. - This site has been around for almost 7 years, it has a google page rank of 3, and several hundred previously indexed pages in google. But it gets no traffic, and doesn’t seem to have a web based monetization strategy at all. - This site has also been around for almost 7 years, it has a google page rank of 5, and also has several hundred pages indexed in google. Like Trading Card Hobbyist, it doesn’t get much traffic, and appears to only monetize through Google Ad Sense.

All else being equal, either of these domains would be a far better choice to start a trading card business online than a brand new domain. Good news for my buddy is that he’s got madd negotiating skillz, so now he’s off negotiating with a couple domain name owners to see if he can pick up a “prime” chunk of realestate for cheap. We’ll see if he succeeds. In the mean time, if you’re thinking about starting a new online business, take some time up front to see if you can get a better domain name. Where better is less defined by “brand strategy” and more directly defined by “SEO Strategy”!

In this case, a rose by some other domain name, may in fact smell more sweet!

Twitter and Facebook - Very Different Vehicles

I often hear people ask “What’s the deal with Twitter? Isn’t that just like the Status feed feature of Facebook? Isn’t it just a feature?” On the surface this may seem to be the case. Twitter’s main purpose and functionality is indeed a micro-blogging feed, much like Facebook’s status feature.

But comparing Twitter to Facebook status because the are both micro-blogging platforms is a little like comparing UPS Trucks to Taxis because they are both automobiles.

Facebook and Twitter are different not because of their features, but because of how people use them. Specifically, they are different because of the differences in how people manage their social networks on Twitter and Facebook. Understanding this difference is critical to your effective use of both as a marketing or professional networking tool. I’ve also talked about how important it is for technology startups to think about how they can leverage these platforms to help virally spread awareness of their product. In order to successfully develop a viral strategy around these platforms, you have to understand how people use them.

The vast majority of Facebook users treat their friends list as a narrowly scoped list of people they know in the “real world”. They are their school friends, their work colleagues, their family members. They have a prior connection with the person in the off-line world, and they’ve extended that connection into the online world. There’s nothing wrong with this use of a social network, in fact many people would argue this is the point behind social networks. But this is very different from how most people use Twitter.

Users of Twitter tend to be much more generous in making connections with people they’ve never met in the “off-line” world. This isn’t to say that the connections made on Twitter aren’t as substantive as those from prior off-line relationships. It’s not lesser or greater, just different. I suspect this difference is primarily due to two distinctions. First of all the “creation myth” of these platforms are very different.

Facebook (as the name implies) was created to emulate the social network of a college yearbook, it was designed around personal connections at school. Twitter was created around the idea of highly wired/connection people who needed to communicate in real time with larger groups of people.

Beyond just the creation myth, these products have slightly different features that make social network growth and expansion operate very differently. One encourages public dialogs and broad reaching nets of friends, while the other makes it easy to find real people you know from the real world.

Twitter for example allows you to have unidirectional follow/following relationships, follow/following lists are public, and by default tweets are either broadcasts or narrowly scoped to an individual recipient, but still presented in the public forum. Facebook on the other hand has tools for quickly finding people by name, location, and association that you’ve already indicated your affiliation with. Facebook has a plethora of features to dial in the scope of a dialog to one, several, or all of your friends.

So what? How does this effect me? It’s important to understand these differences in order to understand how to utilize these platforms. How should this awareness effect product integration? How would it effect using these platforms as broadcast mediums for things like product launches? In upcoming posts I will talk about how these differences can and should inform your strategies for using these platforms. Stay tuned.

Lead from the Top - Citi CEO takes $1 Salary

In today’s House Financial Services Committee hearing, several CEOs of the largest and most prominent banks to receive TARP money were grilled by Congressman. 

On interesting bit of news was Vikram Pandit’s announcement that he has instructed his board that his salary should be set at $1/year and he should receive NO BONUS until his company has returned to profitability.

This is particularly interesting when you consider the debate that has been brewing about executive compensation and the recent rules set by the Obama administration that companies receiving TARP funds must cap their executive compensation at $500k per year.

Many people have argued that this cap will cause “brain drain” and a flight of talent away from an industry where talent is most needed. When I posted the comment “Executive pay caps for TARP, your thoughts?” on my twitter/facebook feed, I got a received a fair amount of debate from my friends and colleagues.

Bob: I’m not supportive of exec pay caps. Regulation-yes, accountability-yes, but pay must be based on performance to be competitive globally. Unlimited upside and unlimited downside. We’re shooting ourselves in the foot with pay caps. Motivation issue. Clearly, no compensation for failure. But the talent will always follow the money - to other industries or even other countries

Me: I agree that we should allow performance to guide compensation, but the results from 2008 suggest that we had a system of unlimited upside and limited downside. Multidecamillion payouts for bankruptcy is not an incentive to make SMART risks, its just an incentive to take bigger risks.

Interestingly Larry Kudlow (can’t get more free market then him can you) said he liked all the elements of Obama’s plan. Basically:

  • Small base salary (check)
  • Incentive “bonus” through restricted stock options (check)
  • No golden parachutes (check)

This sounds like upside for success, and downside for failure to me.

Chris: These top execs have been over-paid for so long and now they’re just making sure that they’re not being over-paid with tax payer money. Makes perfect sense to me.

Bob: “Overpaid” is relative. Was Bill Gates overpaid? 25 years of MSFT shareholders would probably say no. Many other examples. The issue is regulation, oversight, accountability where the public good is at risk, e.g. banking. Clearly we’ve got serious housecleaning to do. But I believe in the power of the individual and great execs are not commodities. If compensation is a motivating factor in an exec’s decision to join/stay with a company, then it is highly likely they will follow the money to companies without compensation caps, which will ultimately hurt or even destroy the capped companies that are now funded by our taxes.

Me: I agree with Bob, that “overpaid” is relative. Also, clearly, the market has allowed the current state of affairs to exist/expand. Not unlike pay in Major League Baseball, companies have been chasing star executives with more and more lucrative packages for fear that the “great manager” will go to the next firm that offers a better package.

So, I agree that we should let the market set compensation…

However, we have long since left the free markets when these companies, managed by these start managers, imploded and required tax payer support to keep themselves afloat.

It’s a little like the young adult who after leaving home, partied away all his inheritance on sex, drugs, and rock’n'roll, and now has come crawling back to live with/off his parents. The idea that their would be new rules in the house: no parties, no hookers, no drunken metal fests at 3am… doesn’t seem unreasonable if you’re gonna live in my house.

Also, heard a great line on NPR yesterday…

“But if we don’t pay these executive market compensation, don’t we run the risk of the ‘best and brightest’ going somewhere else? Won’t the replacements perform worse?”

“How could the replacement perform worse? The current batch has produced the worse results in more than three generations. It’s very unlikely anyone will perform worse.”

Chad: the Obama plan looks pretty sharp - market decides incentives through stock options.

Do a great job, stock goes up. Rake in your duly earned merit bonus. now shut up and row!

Bob: Agree. Punish bad behavior, reward good behavior. But fix/regulate the playing field, not the reward-punishment system. Match the medicine to the disease.

Me: Great point Bob, but… I’m starting to think that compensation structure may actually be part of the disease.

Follow me on this:

  • The circa 2007 comp structure rewarded taking bigger and bigger risks, and had little or no downside for failure.
  • This resulted in smart people coming up with ways to take astronomical risks (massive leveraging) but since there was no downside for failure they stopped paying attention to the potential ramifications of the risks.
  • This sense of all greed for the upside (ok if balanced with fear) and no fear of the downside (whoops, what’s balancing the greed?) fueled the sub-prime bubble.

Regulation - requiring more disclosure of the risk, more transparency, etc… might have helped slow it down, but, I doubt that really would have done much.

I like the idea of giving shareholders a vote on comp packages, at least that would create more transparency. In this case, for TARP, tax payers are the share holders, seems reasonable to Obama the proxy vote.

Chris: Great CEO’s in this generation work for pride and getting their companies where they want them to be. Both Gates and Jobs both take $1 annual salaries. Gates was actually in front of congress and when pressed on his salary he did comment that today’s executives make too much for too little.

Bob: There are so many factors behind our economic problems that I would never claim to understand even a fraction of them but I know that corporate CEOs are definitely not the only issue. Obviously, a big issue is how we keep score as a culture, which created these guys in the first place. I am a bit of an idealist myself but I’ve been around long enough to know that money talks, and for better or worse, we’ve got to compete with China, India, the EU and Russia. I want the companies we bailout to succeed and I just hope that salary caps don’t result in the next generation of management superstars passing over certain companies and industries that we need as a nation.

The news that Pandit is willing to work for free, would seem to suggest that the idea that brain drain will occur if we enforce salary caps is not true. Now, to be fair, there are plenty of people who are detractors of Vikram Pandit. And so he may be a case of exactly the wrong kind of person we want leading out of this mess. But if we believe that the market knows how to pick good leaders, than Pandit is a product of that exact same market we seem to trust. We can’t have it both ways.

Independent of what you may think of Pandit as a man or Citi as a company. I am pleased to see a business leader who is willing to stand up and really put his money where his mouth is.

Sex & Controversy - Getting Your Brand to Go Viral

Is there really no such thing as bad press?

Well, leave it to the crew at PETA, they know how to stir up controversy. They’ve grown out of throwing red paint on rich folks wearing fur… and set their sites on a bigger target: the meat loving, BBQ roasting, and bacon loving (lusting), cowboy culture of America. And honestly, what better way to get cowboys riled up then with hot chicks?

By now, you must have seen the sexy new ad that PETA attempted to run in this weeks Super Bowl. I’ve included it here for your critical analysis. The question I have is, was this a smart move for PETA’s brand?

Ignoring for a second wether or not you actually agree with PETA, or whether or not you find the ad offensive, or for that matter whether or not NBC is acting on good faith by rejecting this ad, but gladly airing the sexy ads from, Budweiser, or other mega brands, there is an interesting analysis to be had of the online marketing strategy employed by PETA in this increasingly online world.

I suspect that PETA’s strategy was actually simply link baiting executed perfectly.

What’s link baiting? If  you’re a brand marketer that’s paying any attention to the online world you had better already know what link baiting is. In all likelihood you’ve paid or considered paying an SEO expert tens of thousands to develop and execute a viral campaign. But if you weren’t rigorous and thoughtful about the goal of the campaign, and you didn’t have a clear grasp of your brand values, then you probably won’t pull off a stunt like PETA has.

The whole point of a link baiting campaign like this is to get people linking to your site… Whether or not people are talking about your brand (good or bad)… may not matter to you. Of course, if you execute your campaign “well” and it does take off, then people will talk about your brand, and you’ll get detractors as well as fans.

It doesn’t hurt if your brand is already considered edgy… Frankly you can’t get much edgier than a brand that literally assaults people by throwing paint on them… So being racy, and objectifying women: it’s hard to make a case that this will tarnish the PETA brand.

What was PETA’s goal? My hunch: Turn some heads (check), get some inbound links (check), and increase their page rank on terms related to vegetarianism and health benefits (check?). PETA already runs which ranks 2 on google behind Wikipedia for “vegetarian”; 5 for “health benefits of vegetarian diet”; 5 for “health risks of eating meat”. That’s pretty good rank to begin with, but this link baiting campaign certainly isn’t going to hurt.

Always Take The Meeting

I have a confession to make… I’m an introvert. This may come as a surprise to anyone who’s worked with me or met me, because as they will tell you, I am one talkative guy. Oh boy, when I get going… watch out. But the truth is, when the phone rings, I’d much rather let it go to voicemail.

Being a technologist, I’ll admit to being more comfortable sitting in my office writing code, designing a database schema, or planning a new cloud computing infrastructure rollout. But as an entrepreneur, you have to get out there. It’s really simple actually, and most people would say it’s obvious.

Customers- they’re outside the walls of your office. Investors- they’re outside the walls of your office. Partners- they’re outside the walls of your office.

If you allow yourself (and your team) to be isolated, you are destined to fail.

But, how do you know when to take the meeting? How do you know it will be a good use of your time? Is that a vendor calling you? Is that investor really going to be interested in your business? Why meet with that business leader if you don’t have something to sell them. How do you decide. Well, it’s actually quite simple…

The secret: Always take the meeting.

I’m reminded of this fact after a couple of completely unexpected meetings this week. Yesterday I met with Kevin Merritt, CEO of Blist, a local startup in Seattle focused on building a revolutionary kind of database that makes it easy for anyone to “Easily share and publish data and lists on the web.”

Kevin and I met through local entrepreneur resources like the Seattle Tech Startups mailing list, and eventually connected on Twitter, but we’ve never met in person. He suggested we meet in person and grab a cup of coffee. I’m not sure if he had an agenda going in to the meeting, but I know I didn’t. Beyond just getting a free cup of Joe (Thanks Kevin! I’ve got the next round!), I got to meet a smart entrepreneur and extend my network. I’m not sure what will come out of it, but after meeting Kevin, I’m sure we’ll be able to be a resource to each other in the future.

It reminds me of a meeting I had last year with a local venture capitalist. I wasn’t really in the market for VC money, and I wouldn’t have considered our venture to be appropriate for his fund’s strategy, but I got an introduction through an entrepreneur friend of mine, and said, hey, I have to take the meeting. Although the meeting didn’t result in an investment, I did get to meet a new business leader, and I must have left him with a positive impression: a couple weeks later, out of the blue, I get an email introduction from this VC to the CEO of Brooks Sports.

Not a bad connection! Good thing I took that meeting.

Ironically, at the time, we didn’t have a product to sell to someone like a Brooks, but again, I took the meeting… who knows where it could go. Our first meeting was just a friendly conversation about Social Media and the Fitness Industry, there was no sale to be had, as we had no product to sell. But the connection was made and eventually a couple months later that connection turned into a great partnership.

The lesson is simple: When the phone rings, answer!

Don’t Let Twitter Pass Your Startup By!

Hitwise, recently released details about Twitters amazing growth, and it appears as if twitter has now surpassed Digg to rank #84 in Hitwise’s list.

If you’re a media start up which has been executing a “social networking” strategy around Digg, StumbleUpon, and other user meta filters, but you haven’t yet embraced Twitter, you’re about to start falling behind.

It’s time to start paying attention!

Some interesting details in the report include:

  • Twitters traffic from users aged 25-34, went from 12% a year ago to 45% today.

  • Digg gets nearly 38.8% of it’s traffic from organic search on Google. Twitter however gets only 9.23% of its traffic from search, and instead gets most of it’s traffic from social networks and other web applications that integrate Twitters APIs. Traffic from Facebook and MySpace combined are almost double the traffic Twitter gets from Google.

  • Also worth noting is that Hitwise’s report only tracks web traffic, and therefore misses all of the twitter traffic which comes from mobile applications.

Why Your Startup Can’t Afford To NOT Hire a CTO

As I mentioned in my last post, one of the many things I do as an entrepreneur is to advise other start up companies. One of the common requests I get as an adviser is the help interview and vet potential CTO candidates. Unfortunately in many cases, the choice to hire a CTO is the worst choice a CEO or management team could make.

But don’t misunderstand me, every technology startup needs the skills embodied by a great CTO, you can’t afford to NOT have a CTO.

So what do I mean, but the skills embodied by a great CTO? Understanding these skills is critical to understanding how to hire the right people to flesh out your technology team.

I recommend that management teams think about the roles of engineering management in three parts:

  • Leading, inspiring, and managing the engineering team - Some people think of this as primarily a “people management” skill. We often give the title of “Development Manager” or “Technical Lead” to this role. These are very much “soft skills”, related to making other people successful, happy, and motivated.
  • Leading the architecture and technical direction of the product - This is closely related to leading the development team, but it is really a different skill set. These responsibilities are much more focused on hard skills, related to deep technical knowledge. We often call this role “Architect” or “Chief Scientist”.
  • Executive technology representation and leadership - Representing the technology team to the rest of the executive team, Board of Directors, company, key outside customers, government or legal parties. This is high end stuff, requiring a level of maturity and preparedness. It’s a combination of soft and hard skills, mostly soft skills. But it should be noted that the more sophisticated versions of these skills are only rarely needed in most start ups.

In very large organizations you will often see these roles divided into different jobs: “Development Manager”, “Architect”, and “Chief Technology Officer”. But in a start up, you can’t realistically afford to pay three six figure salaries to fill these skills.  So what are you to do?

Can you live without these skills? NO! You need to find these skills for your start up!

You need these, and hopefully, you can find them in a single person on your team. My recommendation is to start as close to your engineering team as possible and find the person who is closest to embodying these skills. Once you find that person on your team, then cultivate them to fill out their talents to include the rest of these important skills.

I’ll explain how to do this briefly, but before I do that let me quickly address the most common retort I hear to this advice. Often CEOs and BoDs will insist that executive technology representation is the most important skill they need filled. From there, they usually assume they already have a good enough architect but what they really want is “someone to manage those engineers”. This reaction is understandable, most of us feel more comfortable with “people like us”, so executives want to find other executives to hang out with, and they are afraid of those “engineers” and they want someone like them to “take care of it”.

The problem with this view, is that engineers are usually only inspired by other engineers. Yep, that’s the hard truth of it.

If your “engineering leadership” lacks street cred, then you can be certain that they won’t get far with your team.

Air-lifting in an “expert people manager” is one of the most dangerous things you can do. But finding that inspiring engineer on your existing team, and making sure they have or are learning good soft skills, is a sure way to take your engineering team’s productivity to the next level. If you have five engineers on your team, and they’re being productive and getting stuff done, then you can be certain you already have that leader on your team.

If you don’t have that person on your team, then you need to be very careful in how you add that leadership to your team. Look for someone who could slot into your team and sit side by side with your engineers and write the same code that your existing engineers are writing.

Don’t confuse years of leading large teams, with street cred. In fact, the longer that manager has lead large teams, the higher the probability that they’ve lost their street cred.

This is critical! If your “hired gun” hasn’t fired his weapon in years… he won’t make it on your team. Your engineers will eat them alive. Instead, look for an engineering manager that is still comfortable writing code. Maybe you won’t have them writing code in your organization, maybe you will. But if they can still write code, then they will do a great job leading your engineers that must write code.

Another common mistake that executive teams make is to assume that your architect and your engineering manager can’t be the same person.

It’s certainly possible for these roles to be seperate, but it’s much more efficient and cost effective to have a single person who fills both these skills. And I’d argue that a great engineering manager has many of the same qualities of a great architect. In particular, as your team and your mission grows, more and more delegation to talented engineers are required. This means that your CTO will need to be able to unselfishly delegate to the rest of the team, and truly inspire those engineers to run with the vision of the company and build a great product to meet the business needs.

Finding all of these skills in a single person may seem like a daugnting task, especially when you consider that I’ve said that person also needs to be able to code. But these people are out there, and if your company has a great idea, with an exciting market and the opportunity to work on great technology, then you’ll have no problem attracting them to work for you.

“…people will judge you on what you can build, not what you destroy.”

Wow! What a day. What a day! There is so much to be said about today, so many emotions, so much hope, and an amazing sense of the enormity of what’s ahead of us as a country and a world.

But, I guess, my true colors as an entrepreneur came out today… as I listened to Barack Obama’s inaugural speed I couldn’t help but be inspired as a “builder”, as a “doer”, as a “maker of things”, and as someone who wakes up every morning feeling deeply accountable to make the world a better place than it was when I went to sleep the night before.

There were so many lines that struck me for so many reasons… but as an entrepreur, this line, borrowed only slightly out of context, really hit home.

“…people will judge you on what you can build, not what you destroy.”

This is idea, that the nay sayers, people who prefer to blame others for their plight will ultimately be judged by history for what they are… the problem… this is a very powerful and inspiring idea for those of us who are driven to create against all odds.

In the Seattle high tech startup scene, like much of the country, there has been a rash of recent business closures. And sadly, too often in our immediate community, those entrepreneurs are derided and mocked by the bystanders. This is so common in Seattle, that many entrepreneurs have begun speaking out, and itemizing this local cultural phenomena as one of the reasons our Seattle tech community is less vibrant as other regions (like the oft-cited Bay Area/Silicon Valley).

I have my theories for why this negative attitude is so common in Seattle. I believe this attitude comes from the relatively large mass of local success which has come from a few number of very large organizations. Unfortunately, if my theory is correct, then it’s not something that is likely ever going to change. So instead of worrying about it, and railing against it, I choose to create in spite of it.

I couldn’t possibly say it better than our new President did:

In reaffirming the greatness of our nation, we understand that greatness is never a given. It must be earned. Our journey has never been one of short-cuts or settling for less. It has not been the path for the faint-hearted - for those who prefer leisure over work, or seek only the pleasures of riches and fame.

Rather, it has been the risk-takers, the doers, the makers of things - some celebrated but more often men and women obscure in their labor, who have carried us up the long, rugged path towards prosperity and freedom.

Here’s to a new day in America and the World. Here’s to the Entrepreneurs, “the risk-takers, the doers, the makers of things”!

Why Your Startup Can’t Afford To Hire a CTO

Before Founding Konamoxt, my last gig was the Chief Technology Officer for a local Seattle Startup. I have the classic resume for a CTO of a Startup company… if you’re trying to hire a CTO, I’m sure your recruiter has called me… I get those calls all the time. Mr. Startup CEO, I’m here to tell you, you can’t afford to hire a CTO.

[Note to tech managers and wannabe CTOs out there: Oh, don't worry guys my next post will be why you can't afford to not hire a CTO.]

Today, one of the many things I do as an entrepreneur is help advise other Startup companies. I’m on the Board of Advisers of several other startup companies in the Seattle area. One of the common requests I get as an adviser is the help interview and vet potential development leadership candidates.

Inevitably someone on the management team will say “What we need is a CTO! Can you help us make sure this candidate would make a good CTO?”

Whenever I hear this, my alarm bells go off. Do they really need a CTO? What is happening in the organization that causes them to think they need a CTO? And maybe more importantly what do you think you get when you hire a CTO?

Most of the time, a startup CEO (or more likely the Board of Directors) will decide he or she needs a CTO because the organization is feeling pressure about the product. Maybe the schedule has slipped, maybe the product is buggy, maybe they just have this feeling that something isn’t working right. This usually happens in the case where the CEO is not technical themselves. That CEO/Founder was very likely the product visionary, but they don’t know how to build a product, write code, or lead an engineering organization to build the product.

Another very common situation is when outsiders, often the Board, is frustrated with the overall performance of the business, and they begin looking for “problems”. Unless one of the founders has a past track record of being a CTO or VP Engineering in a larger organizations, this lack of experience will often be blamed for the frustration without much analysis at all of the actual facts on the ground.

Sometimes, this “gut reaction” is correct. Sometimes the engineering organization is indeed rudderless, and the right solution is a new technology leader joining the team. But more often then not, I’ve seen the non-technical leadership jump to the conclusion that new “experienced” blood is what’s needed. When in many cases, that move can actually be counter productive.

The common euphemism seems to be “We need some adult supervision in here!”

But if you’re looking to hire a CTO, you probably already have your engineering team in place, you may already have a team of engineers that are building and have built something. How have they gotten as far as they have without this “technical leadership” you’re so convinced is missing? Nine times out of ten, the CEO has become convinced that the existing team is just lacking that leadership.

That search inevitably begins like this… “Let’s find someone with years of experience. And since this company is gonna be huge, we need someone who’s managed big teams, someone who can take us all the way to going public! We’re going to be a $100m/year business with hundreds of developers in different divisions. We need the kind of leader who’s been there and done that.” Sounds like a job for a CTO, right?

Hiring that CTO, will be the biggest mistake you make. You’ll alienate your engineering team, you’ll waste your money, you won’t be satisfied with the results, and in all likelihood that CTO won’t last in your organization anyway.

Here’s the problem… 99% of the time “that guy” you think matches your wish list, hasn’t written code in years. He might have managed a 1,000 developer organization, but he hasn’t directly managed engineers in years. She looks great on paper, managed a 10,000 cpu data center processing billions of transactions a day… but she hasn’t ever done anything with cloud computing.

When ever I’m confronted with this dilemma as an adviser I’m reminded of a great quote I once heard about NASCAR, I believe it was the late great Dale Earnhardt that said…

“If you see a wreck in front of you, drive toward it, because by the time you get there, it won’t be there!”

This philosophy can apply to a lot of things about startups. The key to applying this quote is to recognize that things are always changing… and if you continue to move forward, then in the future you’re guaranteed to be someplace other than where you are right now. What looks like a disaster in front of you if you stay on course, may in fact be the best, safest, fastest, game winning decision by the time you actually get there.

How does this apply to searching for a CTO? Well, it may be the case that you already have your CTO on your team. You don’t recoginze them yet, because they haven’t yet managed that 100 person development team. That doesn’t mean they won’t be ready when the time comes. You probably only have 3 to 6 developers right now. And even though you don’t think you have a development manager, doesn’t mean that team doesn’t have a leader.

Sure, it’s possible your team has gotten as far as they have with no leadership… maybe as the CEO you’ve been guiding that product vision and you’ve been managing those developers. But unless you speak their language, because you’ve sat in their chair before… then I’d be willing to bet you that one of your developers is actually leading the team while you’re not there. Maybe it’s the most senior developer, or maybe its just the most passionate and sharpest developer.

Instead of hiring an outside CTO, you probably need to take a close look at your team and try to determine if you already have a CTO working for you… but under a different title.

Next post… Why Your Startup Can’t Afford To NOT Hire a CTO

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