12 years at SilverStripe: Q&A with the founders

It was a leap year, the year 2000, that saw 29 February become the day that CMS history was written and SilverStripe officially incorporated. Two years ago we did a little retrospective to see how it all began with Sam, Tim and Sig. There were three fearless young guys fresh out of college who knew the world was their oyster; the world was waiting for them to create something awesome. Tim’s life savings were spent on some equipment, they built their first website with ASP 2.0 from their bedrooms at mum and dad’s, and named their company Totally Digital, which is today known as SilverStripe. Luckily they soon discovered the beauty of PHP and matured into serious businessmen who today have the trust of some multi-million dollar organisations.

Last week, I met with these, still fearless but slightly older, guys to speak about the beauty of being young, innocent and taking advantage of opportunities.

How did it all start?

Tim: At the beginning, Sam worked with ASP from Microsoft as a technology. Then Sig introduced PHP to the game.

What was the biggest challenge you faced when you started your business?

Sam: Going from hobby to business. We were young and had no experience. Coming fresh from college we had no experience from previous jobs. And sometimes we had to make expensive learning curves.

Did you start with a big vision?

Sam: We were focused on the technology, making the business side of it up as we went along. We pretty much did what was in front of us.

Tim: At the time it was dotcom boom, all the hype and craze and a lot of energy and passion, but it was unfocused.

Sam: We saw the case by case individual needs and a client needed to be looked after in a certain way. So building them a website and a CMS from scratch was mostly in response to individual needs.

Sig: We had the idealism of doing something really wonderful with the web, but really; we had no plan.

Tim: We knew we wanted to take over the world, but we didn’t really know how. We saw and took the opportunity to build the tools that would eventually shape the future of business.

Sam: It’s much easier to be idealistic when you’re young. We had no sense of limits, and were arrogant enough to think we could achieve anything. We started very broad - we did everything from building databases to websites and CMS’s, right through to building a scoreboard system for an indoor sports centre.

Sig: Then we found what we liked doing and what we could make money on. We had no mortgages or kids; so we had nothing to lose. It was low risk. Some monthly income in the early days allowed us to experience and dabble in what was going on in the Internet.

What’s the advantage and disadvantage of starting a business when you are quite young?

Sam: The younger you are, the bigger risks you can take. You might not have money, so you don’t have to worry about losing it. One of the good things about the software industry is that the amount of capital you need is very low. This enables young people to start out and gives them that extra opportunity, especially those trying to start out with skills in the IT space.

Is there anything you would do differently today if you could start over again?

Sam: I would choose carefully what I want and focus more on that. We went in many directions, and it helps a lot to focus on what’s important, and really hone in on that.

Tim: We had a good lot of lessons learnt. We had a lot of bad experiences and bad clients. So you should really define for whom you want to work. But in saying that; you learn from bad experiences, too.

Sig: Either direction, it probably would have just been a different set of mistakes. Something we could have done is actually set our sights higher, set the goal and really channeled that.

Can you name a couple of lessons learnt?

Sig: The matter of funding your business through cash-flow, as opposed to taking large investment, is a worthwhile process that constantly refines everything you do. You can’t go the wrong way for too long, or you get into trouble. But focusing on the cash-flow helps you to quickly learn if you’re heading the right way.

Sam: Aim to create a company you’re proud of and passionate about. Its not enough to follow a good idea; you need to deeply care about what you are doing.

Tim: The range of different personalities and opinions among the three of us has been a learning curve in itself. We have our conflicts, but it is always constructive and we always come to an agreement.

Is it difficult to be friends as well as business partners?

Tim: The business was first, the actual friendship came later.

Sam: I met Tim around the time that we started the business. The most significant similarity in your relationship is that you’re doing business together. It becomes the substance of the relationship, and although it doesn’t necessary diminish the other side of the friendship, it by sheer volume it can come to dominate it.

Tim: It would be difficult to work together if you didn’t like each other...

Sam: ..you are sort of getting married, you’re spending half of your life together, your deeply reliant on each other, and if you were to leave, the others would be screwed. You’re committed, and tied to each other in a meaningful sense. You can’t just hand in your notice.

Sig: There needs to be an element of loyalty and respect, too; we try to row in unison. We need to be in sync and heading in the same direction.

What do you like most and least about your job?

Sam: I like watching this company growing into something that is bigger than every one of us. It stands alone. The tough part is when you have to make a decision that is best for the company, but you know you will disappoint someone. But I have to take the responsibility of the consequence of my decisions.

Tim: I like the ability to indirectly touch half a million businesses, then all of their clients too. That’s the beauty of the net. What I don’t like is to see so many opportunities out there and not to have the time or resources to take advantage of them.

Sig: I see web as the major medium in which the world’s humanity is interacting. It is rapidly changing and rapidly increasing its influence in the world. It’s a fun area to be in and to even contribute to. My dislike is the same as Tim’s; all those missed opportunities. How often have I thought: “If only someone built this iPhone app”.

How much of SilverStripe is driving revenue and how much is ideology?

Sam: It is both; ideology and profit. Have your cake and eat it too. We see open source as that opportunity.

It is important to create a business that makes money, otherwise it won’t last. I like Tim O’Reilly’s analogy: “Profit in a business is like gas in a car. You don't want to run out of gas, but neither do you want to think that your road trip is a tour of gas stations.”

Tim: We commercialise the open source tool by using it for our clients. The CMS and Framework give us the USP we need to be ahead of the competition. This is how we grow and why we have an international brand.

Sig: It really is a strong mix of both. If it were just one or the other, we’d either have no customers or no community.

Sam: I would say that we’re socially conscious capitalists.

What’s special about SilverStripe?

Sam: We are kiwis, we’re not very good at listing the reasons that we are special. (laughs)

Tim: We have a good, fun work environment.

Sam: SilverStripe has a culture that focuses on the things that matter; like giving people the freedom they need to create great work. We don’t want to create a bunch of prima donnas. People here are talented, they listen and learn. We are problem solvers, we help businesses and we need our knowledge and talent for that.

What is open source for you?

Sig: It’s partially creator of good will, marketing, and deriving satisfaction for our developers, as well as a billboard for our customers, so that prospective customers are able to fall in love with something real. They can try it before they invest any money. Broadly, its a much improved software. Without open source, it’s too easy for a software to get stuck in the hands of one vendor.

Sam: We wouldn’t be here if we hadn’t open sourced. Industries that focus on capitalising intellectual property directly are struggling. Open source in the software space is an attempt to grow a software businesses without locking down IP, and in that sense, I see open source as the future.

Tim: We give value away for free. We make good profit, but not mega profit. We are not capitalised like other companies, which keeps the playing field level. Software is a way of codifying ideas and thinking. Ideas get more actionable, and open source keeps that knowledge on the table.

What would you do if Google knocked on your door tomorrow?

Sam: What is the outcome going to be? What we’ve created is pretty special. If someone was going to help make that even more special, then maybe we’d consider. But if it was to be swallowed up and consumed by another big ecosystem, then we wouldn’t be keen on that.

Tim: Our vision for SilverStripe was always to create long term value rather than something we’d sell overnight. We’ve had offers in the past, but we never seriously considered them.

Sig: Buying a company usually means buying the customers and sunsetting the product. That is entirely against the idea we had when we founded the company.

Thank you very much for this interview. Congratulations to 12 years at SilverStripe!