Why I joined Automattic – Part I of II

To answer this question, I must first explain how I fell into with the domain industry. This story begins in 2008 after spending the better part the previous 10+ years in and out of the internet space working for various companies from a hosting company in 1997 (the year Dreamweaver was released and long before Matt dreamt of Automattic) followed by IT consulting firms, to eventually becoming a partner in an email encryption start-up. After this company wrapped up (many lessons learned – we got into bed with the wrong VC) I consulted with start-ups in the Toronto area, writing business plans and go-to-market strategies while helping them raise seed capital. On an excitement scale, this was about an ‘hmm, it’s ok, I guess’ but I wasn’t inspired by any new technologies I saw, though some mobile apps did come close.

For anybody who has ever been at a professional crossroads in their life, start-up consulting was also my way of buying time as I contemplated my next move. Being single at the time I didn’t feel the responsibilities I have today – a wonderful wife and two beautiful young boys. Then an opportunity to work at Tucows came my way through my previous business partner who was consulting with them at the time. Being an early user of the internet I knew the brand Tucows but I didn’t ‘know’ Tucows. For me, it was a place where I downloaded ICQ and other free software in the late 1990’s, but I quickly learned Tucows later morphed into one of the world leaders in domains, email, and SSL. They were interested in my business development/sales background and I was interested in learning the inner workings of this well-respected internet pioneer. But as it turned out in 2007 the timing of their email product overhaul wasn’t quite right for me so I politely passed on the opportunity and turned back to consulting for another year, though I did keep in close contact with Tucows. Something about them, their culture and Elliot Noss’ vision of an open internet intrigued me.

Then in 2008, I was once again approached by Tucows to consider a new position they were thinking of experimenting with. Work with the largest clients, learn their respective businesses, consult with them on domains, email, and SSL, keep them abreast of Tucows’ product roadmap, garner feedback, and facilitate the regular day-to-day account management tasks. Career wise several close friends thought this was a step back but I realized I was presented a wonderful opportunity to learn. Email and SSL were quite familiar to me having spent many years working directly with those products, but looking back now domains were still a bit of an enigma. I registered many over the years, even back when we had to fax in orders and it took 10 – 14 business days to actually get it (.coms were also $100 / 2 years back then too). I am not an overly technical person so I didn’t fully understand the deeper inner workings of domains – name servers, DNS records, add grace periods, redemption periods, secondary market, drops, UDRPs, etc. But I was willing to learn.

I was given clients like Endurance International Group which at the time was a small representation of the hosting powerhouse it is today; VistaPrint, a billion dollar company that had just decided to move into the electronic services space; The Planet / EV1 before they were acquired by SoftLayer and now IBM; Media Temple before it was acquired by GoDaddy; soon afterward it was groups like 123-Reg and Fasthosts; until eventually new web-builders like Squarespace and Yola.

It was working with these groups when I actually developed a deep fondness for domains. I was intrigued how each company approached their end users so very differently despite having the same innate goal of selling them a domain, getting them online and up-selling them more ‘stuff’. Aside from the ccTLDs which were mainly getting their traction in Europe at the time, the other main TLDs were .com, .net, org .biz and .info and .me, to a certain extent. Others like .co, and .xxx were not yet commercially available. And name suggestion was very basic and certainly only utilized by a minute portion of the hosting industry.

I would try to educate clients on the importance of domain search and suggestion as an integral part of onboarding, reinforcing how relevant domain choices will lead to higher domains sales and subsequently the sale of more hosting products.  But at that time domains were less of a priority and unfortunately for most hosters, an afterthought. Registering a domain was often buried somewhere on a site between ‘now-that-we-have-your-credit-card’ and ‘did-I-mention-we-have-domains?’ Instead, hosting packages and all of their technical features are what was front and center.

Not long afterward .co and .xxx were introduced (re-introduced in the case of .co.  Over the course of those years the industry was shifting to website builders and ease-of-use web tools. Domains was a way to hook customers in. Blogging was also getting more popular. WordPress was becoming a staple in hoster’s offerings thanks to WordPress.org. At the same time, the .com zone was getting more crowded by the minute. The domain space wasn’t progressing or innovating as fast as it should have been but rejuvenation was around the corner in the form of new TLDs.


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