Photo Credit: Chez Andre on Flickr.

Entrepreneurial Priorities if You Don’t Want to Despise Yourself at Age 80

With the exception of a general, “We’re hiring” post a few days ago, my site has been largely neglected for the past year. It’s not that I don’t want to write. I do. And it’s not like I don’t have things to say because, if you know me, I do. I really do. And it’s not even that what I’d like to say isn’t all that important…. because it generally is.

I feel the need to write today, however, because it directly relates to why I don’t write as much as I used to. And it directly relates to why I, in the eyes of the typical startup founder or venture capitalist, am not a great entrepreneur. In their eyes. I’ll admit that I’m a terrible day to day running a business guy. I’m a terrible “take care of the basics” like health care and witholding taxes” guy. I’m actually a pretty decent entrepreneur though. Put me on the phone with a prospective client, and I can speak their language and close a deal. At the end of the day, being an entrepreneur is all about making money so you can live to play another day.

Or is it?

It’s also about life and lifestyle.

I feel really compelled to write about this because, though I sorta took a mental break from the tech startup world for a bit while I focused on my job and my new life back in on the east coast (and, you know, survival and keeping a roof over my head), I’ve dipped my toes back into the water.  I am as alarmed today as I was two years ago about the entrepreneurial scam that is peddled by basically everyone.

There’s an entrepreneurial scam?

Funny you should ask! Yes. And it goes something like this: “If you’re not willing to give 24/7 to build your startup or company, you shouldn’t be an entrepreneur”.

Jason Calacanis, famously, said in one of his listserv emails on September 27, 2008, eight days after the market crash of September 19, 2008 and two days after the FDIC seized Washington Mutual Bank, that the sign of someone (paraphrasing here) worth being hired/invested in in the startup world is the person who will gladly come in on Sunday. This was the actual passage from that email:

Hold an optional off-site breakfast meeting on a Sunday and see who shows up: If folks don’t show up for you to grow/save the company on a Sunday for a two hour breakfast, they probably aren’t going to step up when the sh#$%t really hits the fan. You need to know who the real killers on your team are and you need to get close with them now. Again, it’s fine to have 9-5ers on your team–if you’re the Post Office. You can’t have them at a startup company. Note: if you reading this and saying I’m anti-family, save it. Folks don’t have to work at startups and some of the hardest working folks I’ve met have families and figure out how to balance things.

UGH. So much wrong with this sentiment. This sentiment screams, “I am what I do” and that is simply the most self-loathing sentiment you can have. It is neither something to be proud of nor is it healthy mentally or physically. I have a lot of respect for entrepreneurs who will go to the Farmer’s Market on Sunday morning. Or who take their kids to the park. Or who go to brunch with their husband/wife/girlfriend/boyfriend. Not so much for the person who opts to work instead of doing these things.

Here’s what that mentality of roughly 2003-2008 got me. It got me a career, yes. It also got me a divorce and years of my life I will never get back. At nearly 38 years of age, that is a lot to bypass in the service of the almighty dollar, ego, prestige and “fame” (whatever the fuck that means).

While I worked my corporate 9-5, I was coming home and then working another 8 hours on client works, building a company or other nonsense. I neglected my son (who fortunately still loves me to death) and my wife, at the time, by working every night until 3am just to pass out exhausted and wake up at 6:30am to go to work again.

Those lost opportunities to be present were squandered because I bought into the charade that if I work longer and harder, I’ll succeed more and have a better life. Rubbish, hogwash, nyet, NO!

After my ex-wife and I split, I naturally did some soul-searching. Work wasn’t our only problem. But I’d say it was a contributing factor to all the problems I could see. I decided to do a 30-day “work cleanse”… For 30 days, work normal business hours – 9-5, 10-6, whatever… and then put my work down and find something to do to occupy my time. That was a hard thing to do since my work was my identity and my habit. However, after 30 days, I realized I was feeling more energized. I got more sleep. This enabled me to focus better on my work when I was doing it. It helped me get things done faster. I felt more alive.

By and large, this 30 day drill has become my lifestyle now six years later. I typically still work Monday through Friday, 9 to 5. I avoid after hours work or weekend work if I can help it. Though I still take side work, one project at a time in digestible portions, because… a little extra cash every month is nice. But, today, I spend time with my girlfriend, cook dinner sometimes, and do stuff that is fulfilling to my life (usually!) instead of investing all my energy into something that will ultimately fade away.

My greatest fear is that, in my latter years, I will look back on my life with regret, building something that doesn’t last while sacrificing the things that really matter on the altar of snake oil salesmen. You are not what you do. Your time spent does not define your character.

In the words of Trent Reznor Johnny Cash, three months before his wife’s death and seven months before his own:

What have I become 
My sweetest friend 
Everyone I know goes away 
In the end 
And you could have it all 
My empire of dirt 
I will let you down 
I will make you hurt

Joe Flacco

The Maturation of a Leader

Football has a striking resemblance to business sometimes.

Despite moving to Austin, my allegiance to the Baltimore Ravens remains as strong, and maybe stronger, than ever. It’s been an exciting offseason with lots of power moves and now training camp is in full swing.

For third year Quarterback Joe Flacco, this appears to be his coming out year. The Baltimore Sun ran a story about him the other day noting that this offense is now Joe’s offense. He’s taking command. He’s inheriting responsibility. He’s taking ownership.

He’s taking more command and making more adjustments at the line of scrimmage. He’s looking to become more effective in the red zone. And he’s tutoring new backup quarterback Marc Bulger when everyone thought it would be the other way around.

“I want to be able to just run the show and go up and down the field, blow out points on the board and come out successful,” Flacco said after a 75-minute practice featuring rookies and veterans coming off injuries. “That’s what it’s all about.”

That’s the mark of a leader and something that anyone who aspires to leadership is required to do at one point.

Since being in Austin, I’ve been exposed more and more to the startup life – something I used to live in as the Director of Technology at b5media, a company that used to be a blog network but now is something, well, frankly, unidentifiable.

As a result of my new exposure to a startup culture, I’ve already talked to a few companys to get a feel of how they do business. It reminds me of those early days at b5media. Four founders, making decisions by committee, and hoping for the best. Sometimes consensus was a blocker to real innovation.

This mode is common for early companies. Small group. Everyone needs to be on the same page to do anything. And they suffer from paralysis of no decisions. No one is willing to take charge and lead.

At b5media, once we took our first round of VC money, Jeremy Wright, became the CEO. He was forced into a role of trying to get consensus but not suffering from the paralysis of required consensus. Many times, those of us in those leadership roles diverged in opinions and advocated different directions. It was Jeremy’s role to distill this feedback, foster the discussion, and then ultimately take ownership of the situation and make his call.

Sometimes it was the right choice. Sometimes it wasn’t.

Imagine this. It’s a third and long situation. The Ravens offense is backed up on their own 10 yard line due to an unfortunate series of downs involving an incomplete pass and an offensive holding penalty. They are down by 13 points with 6 minutes left in the game. The safe call, and the one called in to Flacco by Cam Cameron on the sideline, would be a slant play down the middle to a slot receiver or tight end.

As the offense lines up, Flacco sees the defense showing blitz and crowding the middle. Understanding from experience that this is a situation fraught with disaster and the need for a big breakout play to energize his offense, he calls an audible. Ray Rice on a draw play – bait the offense to continue to see the pass, but then destroy them with an off tackle run. Rice runs for 24 yards and gets the first down and better field position.

If it wasn’t for the leader having the confidence and insight to see the minefield upon him, he might just go with common wisdom or, more naturally, the wisdom of his advisors. However, he decides that he has the information he needs to make a big play, owns the call and gets a win.

While it’s common for young startups to operate on consensus, sometimes it requires someone with enough balls to make a tough call and own it. A good team will support that and have their leaders back regardless. If they don’t, they shouldn’t be on your team.

Photo credit: Keith Allison

welovewordpress

Back in Startup Mode… Announcing WP Engine!

Since I moved to Austin, I have been very coy about what I’ve been up to. There’s a reason for that and today I can tell you all about it. Especially since my good friend Marshall over at ReadWriteWeb already has. :-)

It was very interesting. Back in May, my friend Pete Jackson, who works for Intridea, started making a point of introducing me over to Twitter to one of his friends in whatever city I happened to be travelling in at that moment.

It was in this way that I met Sean Cook, the manager of mobile integrations at Twitter in San Francisco and, when I was in Austin visiting in May, he made sure that I met Aaron Scruggs of Other Inbox who has since become a pretty good friend.

It was after that meeting with Scruggs in May that he connected me to one of the smartest guys I’ve ever met, Jason Cohen. Jason is one of the two founding partners at Capital Thought, an Austin-based incubator. Jason has also built several companies and parlayed two of those into healthy exits. I’ve come to have a tremendous amount of respect for his technical and business savvy.

Jason described to me the concept for a business that he was working on along with Cullen Wilson. A premium, WordPress platform that would cater specifically to the customers who want to make sure their blog is always taken care of from a maintenance and upgrade perspective, but also would offer significant value adds that nobody else is providing in a WordPress-optimized environment.

I’ll get to what all those buzzwords mean in a minute. Stick with me.

We started talking about me joining up with them to take this idea to the bank. Shortly after moving down here to Austin, I joined the team and we’ve been working hard over the last couple months to get to the point where we could reliably take on new customers and talk about our idea publicly.

Today is that day.

So, you’re still probably wondering what the hell WP Engine is and why it’s important, right?

Let’s talk security for a minute. There have been significant security “incidents” in recent months. Most people on the outside simply see “WordPress hacked! WordPress hacked!” – I’m looking at you Chris Brogan, Robert Scoble and Frank Gruber (Techcocktail). In the WordPress community, we know the real issues in these cases were not WordPress but the hosts that the blogs were on. Still, people saw WordPress hacked.

We take this very seriously and have partnered with a provider that has multiple levels of security including Intrusion Detection Systems (IDS) outside of our boxes. We have gone to great lengths to keep our customers connecting to us in very secure ways and keep a close eye on the activity happening on our boxes. This is all very important because if an attacker could get through our outside defenses, chances are they couldn’t do anything malicious without us knowing about it.

Our infrastructure is also built with optimization and blazing, fast speed as a core expectation and deliverable. We don’t overload servers and have the means to see potential performance problems before they arrive. With our dual nginx-apache server configuration, we are able to handle sustained high-volume traffic as well as spikes that are the pain point for WordPress bloggers who suddenly get a story featured on a prominent site.

For the people who claim WordPress doesn’t scale… I call bullshit. We believe we know exactly how to make WordPress scale.

But we’re not just a hosting company. If we were that, we would be our competitors. We are also working on additional features such as “Curated Plugins” which are plugins that are entirely open source, that are popular or in demand from our customers and have been vetted from a security standpoint. These are plugins that we support 100%. This does not preclude customers from using other non-supported plugins, and we don’t dictate what bloggers can have on their blog as some of the other hosted WordPress solutions do. We just say, “Hey, if you use one of these, we’re gonna have your back”.

Other things that make WP Engine different:

  • 3 Smart guys supporting customers personally
  • A “Staging” area for one-click deployments and testing
  • We give back to the community. In fact, I made sure that I could work on the WordPress open source project, write the second edition of my book, and that much of our work will be returned to the community. Code is a commodity. The people and service behind the code is not.

We are not perfect yet, nor do we claim to be. We are a young company and have hundreds of things still to do and hopefully learn from. We are in an “invite only” mode at this time as much of the stuff we are doing and want to do is still not ready. But we are open for business and taking customers. And for $50/mo 1 for a dedicated WordPress environment that has optimization, speed and security plus the flexibility of you doing your own thing with a safety net… it’s a steal, really.

Photo used with permission by Donncha O Caoimh

Notes:

  1. For most customers