I’ve noticed a pattern in many of the VC and entrepreneur blogs I read – very few people ever talk about failure.  

Failure is a key part of entrepreneurship.  As an entrepreneur, angel investor, and venture investor, I’ve had lots of success, but I’ve also had lots of failures.  So has everyone that I know that has accomplished much of anything.

While it’s often difficult to talk about failure, there are a lot of lessons that can be learned from it.  The cliche “I learn more from my failures than my successes” applies directly to entrepreneurship and creating companies.  It can be difficult to be self-reflective, but I’ve personally found it very cathartic to study my failures, understand what I did wrong, learn as much as I can from them, and move on.  Occasionally I’ll have a similar failure a second time or a third time – hopefully I learn eventually.

I’m going to start writing more regularly on failure.  For those of you that have been involved in failed businesses with me, I’ll be careful about confidentiality – so many of my examples and stories will have the names changed unless I feel like sharing the posts with the people involved in advance.  I’ll try not to self-censor the stories, although the “personal denial / rewrite history impulse” is a often a tough one to overcome.

I also encourage my fellow entrepreneurial and VC bloggers to talk more about failures, alongside their successes.  Entrepreneurship is really hard and the lessons come from both sides of the equation.

Nick Bradbury, one of the great programmers that I know, has a post up about his approach to working out new ideas.  He also has a few hints about things he’s playing with for the next version of FeedDemon.  I’ve gotten to know Nick over the past year or so since NewsGator acquired Nick’s company and love his style and his products (I use FeedDemon all day long on several machines – it’s my primary newsreader.) 

Back when I was one of the world’s best Basic programmers (self proclaimed, although my partner at the time liked to remind me of this random outburst on a regular basis), I used a very similar approach – just start coding for a while, bang into some of the real issues, and – when I feel like I’ve figured out the right approach, but well before I’ve put the final touches on everything, throw it all away and do a design / code process.  As I’ve been able to work with some great software developers (and plenty of not so great ones) over the past twenty years as well as helped build companies like Rally Software that are working hard to help spread new approaches like Agile Software Development, I’ve seen – over and over again – that there there are a few key techniques that make all the difference in the world, especially early in the design phase of a new project or feature set.

Yesterday was my 13th wedding anniversary.  Amy and I went out to dinner at the Flagstaff House with Seth and Greeley who were celebrating their 3rd anniversary.  We had a wonderful time – I wouldn’t trade the last 13 years with Amy for anything (and I suspect Seth and Greeley feel the same way about each other.)

We spent a lot of time talking about how satisfied we are with our respective existences on this planet.  It’s a huge pleasure to be able to sit quietly at a nice dinner, looking out over one of the most beautiful views of any city that I’ve ever seen (Boulder from the top of Flagstaff is special), and enjoy the company of a few of the special people in my life. 

At some point in the conversation, we started discussing the ever present “introduction” question that comes up often, which is “What Do You Do?”

We decided the best answer – inspired by one of Amy’s friends – is “I’m Happy.”

When Niel Robertson – the founder and CTO of Newmerix – started talking about his idea for a set of “next-generation software quality assurance” products aimed at packaged application vendors, he regularly listed several packaged application vendors, including PeopleSoft, Siebel, Oracle, and SAP as candidate packaged applications to target.

Newmerix focused their development initially on PeopleSoft products and has released three products – Automate!Test (automated software testing), Automate!Change (change management), and Automate!Program Manager (product management and regulatory compliance) – all for the PeopleSoft platform. 

When Oracle acquired PeopleSoft, a number of VCs that I know said something like “Brad – your screwed – there’s no reason for these products after Oracle owns the entire ERP footprint.”  “Au contraire” I responded (using one of the few French phrases that I’ve actually managed to learn), the trend and complete migration zoo that Oracle will generate insures the need for these types of products (if you want a hysterical and detailed overview about why this is happening, take a look at Niel’s brilliant post titled “I Pity The Fool” – I bet you never thought that Mr. T and the elusive Dirk Benedict could be woven into a serious discussion of Oracle’s migration path for the various products they’ve acquired.)

Of course, only time (and performance) will tell the end of the story, but so far it’s getting more and more exciting every quarter.  However, every time I talked to Niel, he’d look at me and say something like “SAP.”  Sometimes it was more, but often that was it.  Today, he backed up his word(s) by announcing that Newmerix now supports SAP’s products.  We are starting via the acquisition of the Object Manager product line from a company named Skywire – these products immediately become Newmerix Automate!Change for SAP and Automate!Program Manager for SAP.

These acquisitions use a long time “early acquisition” strategy that I’ve used successfully in many of my portfolio companies (Fred Wilson kindly referred to me as the “master of the venture rollup” – fortunately I can count some real masters like Jerry Poch and Len Fassler as mentors.)  If you’ve followed NewsGator’s trajectory, you know that they have acquired three companies to date – FeedDemon/BradSoft, NetNewswire/Ranchero Software, and Smartfeed.org/Windows Mobile Reader.  

As an early stage VC, I’ve found that when you’ve got a clear long term strategy developed, a super strong leadership team that is open to integrating new technologies, people and products into their company (vs. a classical “not invested here approach”), and a willingness to get close to great small companies that can help you quickly extend your product footprint, a buy (vs. build) approach is often really compelling.  There are lots of risks and not every acquisition or company is successful, but if you do it right, you can end up with some very nice companies like Return Path.

Congrats Niel and the Newmerix team on your nice strategic move – I look forward to the next one.

A blog reader pointed me at the new JWP creative ads that are up on The Huffington Post web site.  I think they are absolutely brilliant, although Amy suggested that the Scruffs ad was simply an excuse for pornography.  It’s pretty wild what you can end up when you don’t have to worry about the FCC.

One of my portfolio companies – Klocwork – has started a blog called g2zero: better code = better business in conjunction with New Rowley – a technology research and analysis company. If you are a software developer or a business person who cares about software quality, take a look.  A similar blog – On Be(come)ing Agile – run by Rally Software (another portfolio company) – on Agile software development – has been well received. 

If you are interested, take a look at them – feedback welcome and encouraged.

My buddy Ryan McIntyre – who is in the process of moving to Boulder – gives a great example of an issue with our friendly neighborhood online mapping services and then goes deep to understand what is actually going on and where the problem comes from.  He also describes the obvious unintended side effect – one that I personally experienced last week in Connecticut when my driver was relying on Yahoo Maps for directions to my meeting.

A blog reader who I know and have worked with in the past asked me the following question:

I was interested in your thoughts on when entrepreneurs realize they need experienced help and have taken the company as far as they can, when they let go, when they stay too long and the real smart ones that know when to bring someone like me in early and work with me instead of fighting against me.

This friend has been the number two guy in several companies.  In each case, he was brought in by the entrepreneur as the CFO or the COO.  In the situations I’m aware of, he was initially welcomed by the entrepreneur (who – in each case – was the CEO and had an autocratic style), but – after a while, started to have real difficulty working with the entrepreneur, especially as the company outgrew the entrepreneur’s experience base.

As I pondered this question, which would require an entire book to really address it, I realized there was a parallel issue in all the situations I was aware of.  My friend is an extremely capable medium stage executive.  He’s not a raw startup guy, but he knows what to do from 50 to 1,000 people.  In each case that I’m aware of, the entrepreneur “brought him in” to help “get the company to the next level” (where have you heard that before.)  However, the entrepreneur / CEO didn’t really cede control and – when my friend started to put his mark on the company, a very predictable friction occurred.

While I think this kind of relationship is possible, it’s critical that the entrepreneur and the new executive agree on roles and rules of engagement up front.  I think the biggest problem is that during the recruiting process, both sides are selling the other side on their desire to work together and their ultimately flexibility.  Since the entrepreneur is looking to hire and the executive is looking for a job, there’s a fundamental conflict in their motivations and the honest, difficult, confrontational stuff doesn’t come out – until later.

My simple advice to my friend – once you get past the “selling part” of the process and have a real offer on the table from the entrepreneur, go out to dinner (or better yet – get on a plane and go somewhere together for the weekend) and have the real conversation about what life is going to be like.  See if you can get the issues out on the table before you accept the job.  If you can, listen carefully, engage, and see where you go.  If you can’t, you just learned something huge.

Predictably, the same information applies when an entrepreneur is considering a new investor – VC or otherwise. 

One of my favorite words is “fuck” – I’ve always viewed it as one of the most versatile words in the human language.  My mom used to cringe whenever I said it – now she just smirks at me.

Imagine my delight when I came across a scholary paper titled “Fuck” by Christopher Fairman of the Ohio State University – Michael Moritz College of Law.

Fairman’s paper is phenomenal.  In his words, his goal with the paper is as follows:

This Article explores the intersection of the word fuck and the law. In four major areas, fuck impacts the law: First Amendment, broadcast regulation, sexual harassment, and education. The legal implications from the use of fuck vary greatly with the context. However, to fully understand the legal power of fuck, the nonlegal sources of its power must be tapped. Drawing upon the research of etymologists, linguists, lexicographers, psychoanalysts, and other social scientists, the visceral reaction to fuck can be explained by cultural taboo.

This is not a humorous paper (although I found myself laughing out loud numerous times.)  As I worked through the paper, I got increasingly frustrated and discouraged by the inconsistency in the application of the law and the irrational behavior in key situations by people reacting to the word fuck.  Like every good scholar, Fairman states his conclusion in his introduction.

Fuck is a taboo word. According to psycholinguists, its taboo status is likely due to our deep, subconscious feelings about sex. The taboo is so strong that it compels many to engage in self-censorship. However, refraining from the use of fuck only reinforces the taboo. In the process, silence empowers small segments of the population to manipulate our rights under the guise of reflecting a greater community. Taboo is then institutionalized through law, yet at the same time is in tension with other identifiable legal rights. Understanding this relationship between law and taboo ultimately yields fuck jurisprudence. However, all the attempts to curtail the use of fuck through law are doomed to fail. Fundamentally, fuck persists because it is taboo, not in spite of it.

74 pages and 409 footnotes later, Fairman finishes with “Fuck must be set free.”  I agree. 

Oh – and the title of this post pays homage to Bono at the 2003 Golden Globe Awards.  His statement “This Is Really, Really Fucking Brilliant” which he made when he received the award for Best Original Song in a Motion Picture was delivered live on the East coast but was bleeped out on the west coast.  Maybe Bono will come up with a song titled “Set Fuck Free.”

Update: I just stumbled upon Mark Cuban’s post titled Cursing that he wrote earlier today.  It’s brilliantly aligned with this post.