Mixing Friends and Business

Dating girls in my high school – that was a mistake! It was a small catholic high school (Mary Immaculate Academy) and everyone knew everything about everyone. My first “girlfriend” was in my sophomore year in high school, I was a bit of a shy guy then, and she had a big crush on me. Asking all her friends what to do, i quickly found out she was interested in me. So I took the plunge and asked her out. That was pretty annoying, the gossip, the stories, etc. Didn’t last long, and then more gossip, more pressure, more tension about the DRAMA. I decided I would date OUTSIDE OF MY SMALL HIGH SCHOOL so that the stories and gossip didnt go around the lunch table and I could control my personal life and my school life.

IS THAT EVEN POSSIBLE ANYMORE? I mean, I have written in previous post about separation of personal and business . Seems like this social media is good and evil at the same time……

Here are some examples of problems that may arise, and some other stories of what I have run into.

• Dating in the workplace – Similar to my high school girlfriend story about (blush still!), this is commonly said to be “don’t shit where you eat” – which crudely means, unless you are 99% sure you will marry this boy/girl, you had better not try it. Its not always fun thinking “with the end in mind”, but WHAT IF THIS SEXY GIRL or GUY puts you in a weird situation where you have to either go against them in the workplace. Or fight for a raise? Worse yet, what if you get in fights over the weekend, at night, and then you have to see them every day at the workplace. And then the breakup…yea, well not really a breakup because you have to see him/her every day, right?!?!

• Hiring Friends – I always have friends approaching me for work, or projects, etc. I guess I am a sucker, or maybe I get a power trip maybe a mix of both…..), but I would love to hire everyone – not just friends, but people who are excited and ambitious. Then, I have done it and hired friends. And we promise that we won’t let work get in the way,and if work becomes a problem we’ll stay friends. Yea, that is tough. And budget cuts, or job shifts, or raises, how do you handle it? And then, a night out on the weekend, how can you avoid discussing the job. Gossip, etc. I mean, its human nature.

• Customers that are friends – When I started a ecommerce website www.pimpguide.com, it was my first ecommerce site. This was October 2004. I thought, hey, if all my friends buy 1 thing, I’ll be rich! I can actually remember about 2 people who ever bought from me on that site. And that was after months of promotion, pushing, etc. But thats kind of easy, selling a couple products and the transaction is done. More difficult friend to customer sales are websites and service. You then wonder, ok, is this beer work, or are we out on the town? Who pays for dinner? How much should I bill.

• Business Partners that are friends – This is one that is always a red flag when talking to seasoned entrepreneurs. Similar to friends becoming roommates and then fighting about one not stocking the fridge as much as the other, or who cleaned the bathroom last. It means you have to share the decision making, the financial ups (and downs!), and other stress that comes along with a startup. Again, I think it comes down to writing it down, making a clear plan. Also, its almost better if there are “opposites” to fill the gaps in the organization versus the sales, financial, technology, etc. But I keep getting into situations where I mix friends and business, and it strains the friendship as financial strains so often get involved.

So when you make these deals with friends, its going to be tough. Especially in a small startup environment. How do you control the future – YOU CANNOT. It will test friendships, just as small startup test every single cell in your body. You have to be on your toes, watch your back, be flexible an adapt quickly and smart.

But yea, I guess it means sometimes you’ll have to “screw” your friends if you get in the above arrangements. Or the will “screw you”. But then you or they will say, “hey, this is business”. And you have to realize that.

Maybe not just that its business. But that its a GAME. Business is like a game. And in a board game, like risk, there will be winners, and losers. But after the game is over, hopefully people will shake and laugh about how it went down in the game. And learn about each other in the process.

But tying this to social media I AM GLAD facebook and this stuff didnt exist when I was in high school. It was tough enough with just phone calls and beepers. There is so much overconnection. I hope that students can focus on their studies and their careers. But everyone sees everything a bout us, and while that is great for promotion, its not so great for privacy and peace and quiet!