Guys To Know: Dirk Elmendorf

Married for seven years, Dirk and his wife, Annie, an amateur triathlete, have two children, and in Dirk’s words, “have happily put down roots in San Antonio.”
Though he maintains close ties with Rackspace, Dirk left the company in 2009, ready to take on new challenges. His latest venture, r26D, brought him full circle and back to his startup roots, where he now advises other startups through the difficult and often overwhelming demands of software and business development, an area Dirk knows well. He also runs TruckingOffice, an online application built to manage small trucking companies.

Despite his impressive workload, finding time and creative ways to give back to San Antonio is hugely important to this proud transplant. Currently, Dirk serves as a trustee for the Witte Museum and is on the board for the Hemisfair Park Area Redevelopment Corporation. Promoting education is also crucial to this polymath, and he is active in the GEMS program at UTSA and the Trinity Entrepreneurship program and serves as an ambassador for entrepreneurship and technology for the 80/20 Foundation. I caught up with the self-branded “economysizegeek” to find out a little more about his life, his passions and the many ways he puts his knowledge to good use.

Q: In what capacity are you still involved with Rackspace?

A: Once Rackspace got bigger than the town I grew up in, I got a lot less effective at getting things done. I’m still involved in the onboarding program, and I participate with special projects when it makes sense.

Q: At r26D, you’ve chosen to share your wisdom and experience with others who have their own Rackspace dreams. How have the challenges changed since you were building Rackspace?

A: With r26D, my original idea was to build a small team of people who could get things done and then seek out opportunities in the startup world that had big ideas, but lacked the experience to know how to scale them. Our path has taken a different turn. We do provide guidance to a number of startups, but that did not turn out to be our main focus. When we started Rackspace, it was incredibly difficult to get things going.

Everything about it was hard, but that ended up being a great barrier to keeping competitors out. Today, you can form a business and be online in minutes. Thanks to the cloud (and companies like Rackspace) you can scale as you grow. That has resulted in a glut of competition for any idea. That means that every startup has to get really good at standing out in spite of the noise their competitors generate. Technology still plays a role, but branding and communication are essential to success now. We were given a lot of time to figure all that out at Rackspace, but now you have to hit the ground running.

Q: You list your title as “growth hacker” at TruckingOffice. What does that mean?

A: Growth hacker is a specific kind of marketer. The focus is on using technology and testing tools to drive specific metrics that lead to growth (hopefully exponential growth). It allows me to combine my technology skills and my experience with traditional branding/marketing. It also marks a shift in my focus. At Rackspace, I spent most of my time working on the actual product. People with a lot more experience in the trucking industry drive our product road map. I’m focused on making sure that people discover, try and convert to our product.

Q: As the @economysizegeek, you recently tweeted this in regards to the new Legos targeting girls: “At this point all I care about is more kids building.” Care to elaborate?

A: Today kids are bombarded with technology that allows them to consume (Hello, iPad!), but the future belongs to the creators. I don’t know what their medium will be, but I know that the more you can engage kids in thinking about how to take what they have before them — break it, fix it, remix it and rebuild it — the better you are preparing them for the future. That is when they can apply all the things that they end up asking, “Why do I have to learn this stuff?” It isn’t so abstract when the problem is right in front of you. I think of Legos as that first gateway into the idea that you can take a pile of abstract pieces and turn them into something fun and meaningful. Those are early lessons that pay dividends down the road.

Q: Tell me a little about the volunteer work in which you are currently involved.

A: I have two main thrusts to my charitable work: The first is a focus on downtown San Antonio. San Antonio is a city on the rise. I feel like the San Antonio I came to in 1993 and the San Antonio of today are worlds apart. I’m not from here, but I’ve put roots down here, and I want this city to be the best place possible to live. I’m in the process of moving downtown, and I’m excited about all the potential being unlocked there.

That is part of the reason I got involved with the Hemisfair Park Area Redevelopment Corporation (HPARC). I really believe that making Hemisfair Park a place for San Antonians is an important part of reshaping how we all think about downtown. My second interest is in igniting a spark in kids for math, science and technology. When I was growing up, I couldn’t name a single programmer. Now even my mom can name three (Gates, Jobs and Zuckerberg). All too often the people who have great success are put on a pedestal, which makes it hard for kids to see how they can achieve great things.

I want to change that mindset. I try to get kids to see that they are all capable of being world class at something. It starts with a passion and a willingness to put in the time and effort to become great. Those small steps can add up over a lifetime into something truly amazing.

Q: I understand you are a beekeeper. Any plans for a honey startup?

A: This one is still pending. I’ve been housing my bees in hives I built myself as an experiment. I’m in the process of redesigning the hives for the hobbyist that is more like me pressed for time and loves gadgets. That may result in the first fully instrumented hive that lets you know what the bees are doing even when you aren’t around … or it could end in a disaster! That possibility is what makes it interesting.

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