Don't Read Emails You Wrote At Age 25


When my nana passed away this past spring - my immediate and extended family promptly ransacked her house for goodies. I found a drawer - in her really ornate 1970’s side table - a bunch of “Jen Kirkman” memorabilia…horribly embarassing headshots, newspaper clippings of me on a pony in my childhood and various emails that I had sent my mom, who apparantly printed them and shared with nana.

One such email that I wrote in 2000 caused me to cringe so much I had to be removed from my floor by the jaws of life. My injuries are minor except I have a slight film of douche-bag on me that I’m not sure can be removed anytime soon.

I had a job in the year 2000 that was pretty sweet. I was hired to travel the country in a van but sleep in nice hotels and eat in nice restaurants when not driving in said van. I was with a few producers and other writers. We ate oysters and drank cocktails on Miami Beach, staged a parade in New Orleans and ended up spending 2 weeks in all parts of California, from podunk military towns that wouldn’t let us go to their karaoke nights - to a wild week on the Sunset Strip.

What the hell kind of job is this? It was one of those internet start-up companies. Our bosses, who were not wrong - just too early, knew that the next phase of the internet was watching video. I thought that was absurd since I had a crap laptop and it took so long to download email, I just called people. But I realized that these guys were millionaires for a reason and I was not…for a reason.

We had a web-TV show that was like Road Rules meets The Real World. We pulled stunts and pranks around America while revealing our personal selves and interactions with each other via short web videos and blogs - before they were called blogs.

Obviously, my bosses were right. People do this shit now. But they didn’t then. And after our first round of investments, no one else would sink their money into us and we were all let go over a case of beer one Friday afternoon. I had trouble understanding. When were we let go? Right now? Like, right this second? But, I thought you guys had millions? Oh, you personally do but can’t bankrupt yourselves on a business model that is ahead of it’s time? Should I have been paying attention to all of the news coming out of Wall Street, considering I worked…at a dot-com, on fucking Wall Street????

So, week one of this job - we were all flying high. Promises were being made and smarter people were hoping the promises were real but knowing how business works. I didn’t know how anything worked. So I wrote this email to my mom…(I included only the most cringe parts, which is most of it.) Oh, and the email is titled, “For Those Who Doubt…”

“Hey, well, it turns out the two 27 year olds who run the company are worth three HUNDRED million, not thirty million as previously thought. They are extremely well-known in the web world so their connections are helping out our press. We are pretty sure we are going to get written up (I don’t know if it will be an article or a blurb) in Time Magazine.

For our trip we are getting equipped with cell-phones, laptop computers and a little device, which I guess is a mini laptop but it’s as small as a phone and you can type on it - from even a mountaintop! The GAP is totally going to sponsor us, so we will get free clothes.

Also, it looks pretty good that a better website or even a TV "network” on the web will buy us, which would mean a lot of $$$ for us, as in retiring early. It’s business stuff that I’m not too sure about except that it will mean BIGGER paychecks.

I am not in any way saying this will become a hit web and TV show but this is all about connections, if the show fails we have made definite TV connections so we are totally safe.  I am writing this so you can tell your friends when they say, “Well…I never heard of it.”

If this company were to fail, it would be nearly impossible and only due to a literal disaster like an earthquake or flood…or something else that I don’t even know what. It’s as solid as anything else.

Love, Jen"

CRINGE!!!!!!!!!!