5 with Bob Kerstein, the man who traded Windows2000.com to Microsoft in exchange for Bob.com.

Bob Kerstein, founder of Scripophily.com

Bob Kerstein is a certified public accountant who has held numerous senior accounting & finance roles, including several CFO positions at publicly held companies. In a roundabout way, his finance background is what got him involved in the early days of the internet.

Kerstein’s finance background helped pique his interest in scripophily, the study and collection of stock and bond certificates. Shortly after he began getting involved in the certificate industry, domain names were newly available for the public to register. Without knowing much about the internet, Kerstein registered Scripophily.com.

Here’s 5 with Kerstein:

How did you first get involved with the internet and domain names?

I bought scripophily.com in 1996 because my hobby had started turning into a business. I owned an antique store and about 5% of our sales came from stock and bond certificates. It made sense for me to try to sell my certificates online – and it worked. I passed by everyone else. Shortly after I began selling online, my sales reversed. Now, 95% of my sales were certificates from my website. Others in the industry weren’t happy. I attended a conference and was told that I needed to ‘pay my dues’ and work my way to the top like everyone else. But I got a lot of press when I launched the website and I haven’t looked back.

What are some of the other domain names that you owned early on?

I’ve owned and sold domains like:

-Broadband.com

-Dividend.com

-StreetMap.com

-Voltage.com

-Womb.com

Back then, no one was sure what would come of the internet. I believed in it, but it was expensive to keep domain names for a long period of time if they weren’t selling. I dropped several great domain names, including Englishman.com

Tell us the story of Windows2000.com

I registered the domain in 1996 and built a site with links to live cameras from around the world. The site was ‘your window to the world’. Well in 1998, Microsoft decided to call their new product Windows 2000. All of my friends told me I should sue them. In fact, I had several lawyers contact me to ask if they could represent me. I turned them all down, though. I’m not a litigious person and I wasn’t interested in the uphill battle that would be suing Microsoft. I was able to get in touch with someone at Microsoft and we basically agreed to not sue each other.

At the time, I formed an agreement with Microsoft. They used some of my content on their sites to help build their content brand. In exchange, they put a link back to my site that said “Windows 2000™”– my trademark.

I quickly realized that Windows2000.com had a limited shelf life. After the year 2000, it would be next to worthless. I decided to put my website up for auction. However, when I let my Microsoft contact know, he was less than thrilled. A short time later, I got a nasty letter from an attorney at Microsoft telling me that I couldn’t auction the site because I was using their trademark. I called the attorney and asked him to visit Microsoft’s website. When he saw the “TM” for my brand, he understood that I was well within my rights to sell the site.

Microsoft then made me an offer. I can’t discuss the financial details of the offer, but I can say this: It was good, but not life changing. However, I saw an opportunity. Microsoft owned Bob.com – my first name. I told the attorney that I would happily give them Windows2000.com if they would add Bob.com to my offer. They accepted, and the rest is history.

What do you think about the future of domain names?

I think that .com and brandable domain names will always be good – the shorter the better. You want to own a domain name that you can build a franchise or business around.

Early on, domain names were king. Now, Google has come along and has really diluted domains. Users used to find websites with direct navigation – now they rely on search. It hasn’t hurt the “brand value” in domain names, but it has hurt the direct navigation value.

What are your thoughts on the new gTLDs?

I think they are cool and there are some great names to be picked up, but I don’t see them showing up in search engines – that’s the problem. It’s like I mentioned before – there’s value in the brand, but I don’t see the direct navigation value there.

A big thanks to Bob for sharing his story. If you have questions for him, please leave them in the comments.