Rob Thomas: 5 Lessons from 5 Years of a Startup

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5 Lessons from 5 Years of a Startup

Rob Thomas, CEO, Zilker Technology

Five years ago, four of us started Zilker Technology, a digital consultancy and systems integrator. We sat in a small room for almost 2 weeks (sometimes breaking for tacos and beers) determining who we wanted to hire, what our focus areas would be, how to scale and how we would get paying customers. It was a bit intimidating, but we took it one step at a time.

Over the five years, a number of concepts have emerged from the experience. I have Googled “lessons learned from starting a company” and there are a lot of great stories and lessons out there. Mine are somewhat covered in other lists, but these are personal to me, and truly keys to the success we have had at Zilker.

Bet on Yourself

When I moved into sales from a technical role in my late 20s, I was asked in an interview, “Why do you want to be in sales?” My inside voice was saying, “Well, I want to make more money”, but when I really thought about it, at the core of making more money is having a greater influence over the outcome. Most sales people have a significant commission element to their compensation (risk/reward), and therefore have a bigger impact on their income. I said, “I like to bet on myself”. That idea not only served me well through my sales career, but was at the core of my decision to leave a cushy VP of Sales job to start a company. It was an opportunity to again “bet on myself”.

I ask people that I am recruiting into Zilker the same thing. I believe that it is very telling about a person’s motivation. If someone wants to join a rocket ship for the ride, I am not sure a start-up company is a good fit. If you want to get on board knowing that the success of the trip will in some ways depend on you having a material impact on the outcome, you have come to the right place…which leads us to the next lesson.

Know when to roll up your sleeves and when to Enable and Delegate (Trust and Verify)

The smaller the company, the more hats people have to wear (and the more impact every individual has on the outcomes). The careers of my partners and me have been varied, ranging from founding a (different) company to being part of large corporations, as well as start-up experience (with mixed success). This variety of experiences prepared us to “do what it takes” to get results. Our CFO, for example, who will quickly remind he has no sales DNA, sold one of our first projects as the result of meeting a neighbor while mowing his lawn. Our CTO collaborated with me on our first marketing and sales collateral, some of which is still used today. As an entrepreneur, you begin by staring at a blank white board and then figure out, step by step, how to get your first customer, hire motivated people and continue to build from there. Flexibility of responsibility is key, until…

You get bigger and the CFO selling deals is not an effective use of his time. Same for me, the CEO, who sold to and managed clients for the first 3 years. As the company scales, it is critical to hire, develop and empower leaders and doers in the organization. When a company has 4 customers, it is pretty easy for the founders to stay on top of sales, marketing, delivery, etc. When a company has 60 customers with multi-million dollar clients, a broad and strong team is critical. I have seen too many entrepreneurs (and my partners and I have been guilty of this as well) not let go of the responsibilities and activities that got them this far. Proactive talent recruitment and mentorship is critical, but something often forgotten is delegation. You have these talented and capable people…why do you need to be on every call with them? With our growth rate at Zilker, this is an ongoing challenge, but as they say, “admitting you have a problem is the first step to recovery.” If any one of our founders or leaders cannot take a 1-2 week vacation without checking in and being involved, we have failed to properly scale.

Be Aggressive, not Conservative

Since this is the first company where I have been a founder, I initially did not have a good grasp on how fast we were capable of growing. We did not take investment capital, so we were living hand to mouth, so to speak, on the business we were selling and delivering. A key early lesson was to not wait for the business to arrive before investing in the talent, but to instead invest in the talent to get the business. In the services world, it is easy to assume that you cannot hire delivery talent until the services are sold. My experience has taught me otherwise. Hire the talent that will help you sell the business. They will not only be ready to deliver the work when it gets sold, but will have helped you seed many other opportunities along the way, allowing you to hire even more people. I have seen many professional services companies take the opposite approach. Some of them started years before we did and are still about the same size as they were a few years ago. Hiring to the demand you know you will create is another example of “betting on yourself”.

Lead, Don’t Manage

There is not a lot to say here that hasn’t already been said by a lot of people, but it is worth reinforcing its importance. Command and control management structures in business are just not effective anymore. A common counter to this position is “Without clearly defined management structures, how do people know what to do and how they are measured?” That is simple…a lead first style doesn’t mean you do not provide guidance, enablement, direction and feedback. It just means that you do it in a way that encourages people to want to perform with and for you, not because they fear making you unhappy or worse, potential punishment. You should have a management structure, but the managersleaders should focus on pulling the string, not pushing it .

A Remote Workforce is both a blessing and a challenge, but mostly a blessing

I live in the San Francisco Bay Area and am the CEO of a company that is headquartered in Austin, TX. We have 150 teammates in North America across at least 20 states. We also have offices in Belgrade and Chennai. 20+ years ago, this remote concept would have been considered absurd! Our focus has been on hiring the right people regardless of where they live. When you are growing as quickly as we are, talent, motivation and experience are difficult to find in just one or two markets. Creating and maintaining a connection to each other is obviously difficult. Most people in North America do not go to an office every day, and most don’t even have local access to a Zilker office. So, we take full advantage of video conferences, annual company get togethers and gatherings when people are visiting customers or otherwise nearby. We have developed a “sherpa” system where everyone in the company has a person they touch base with regularly to chat and share (this is not their manager). We even have a virtual happy hour once a month on video conference that is organized by one of our team members. We have a lot more evolution and improvement to get and keep our teammates fully engaged, but I firmly believe in remote workforces. Hire motivated and talented people where they live and you can build a stronger team for the long haul.

If you made it this far, I hope you found a useful nugget or two. I am very proud of the the Zilker team, our growth and am excited for the next 5 years!

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