“How-Do”, not “How-To”

I’m a sucker for a good martini. I’m also a sucker for my bartender friend Sean, who likes to play “guess what’s in this drink” in order to make me better as a bartender and to try out his new combos. I have recently become a huge fan of the conversations that my roommate and I have after a few of these test-drinks.

We are toying around with the idea of starting our own creative ad agency (firm?). I know my strengths, what I can do and what I am capable of. Roomie knows her stuff too. So why not? We’re making decent money at the restaurant – we’re supporting ourselves and have some wiggle room. Working at the restaurant allows us to have ample time to think about getting this company in the works.

Where do you start? I’m up to my eyeballs in articles about this and I have a couple of mentors who have successfully launched their own companies. I don’t want to sound like a moron when I go to these people for advice. I need to know enough of the lingo to be dangerous. I need to sound like I know what I’m doing – when in fact I have no earthly idea.

This idea is great and it’s killing me at the same time. Does the “starving artist” lifestyle apply here? Penelope wrote a great article about how to be an artist, and that you shouldn’t quit your day job, etc. Does that same philosophy apply? In my case, I’m about to graduate, I’m starting to build my relationships with people who could some day employ me. Do I keep moving forward in the job search, accept positions so you can get experience and learn, and then whenever you get around to starting your own business, you do it? Or do you drop everything (except a source of income… like bartending) to start it?

My roommate and I will both be at SXSW from the 13th to the 18th. If you know anything about business, how to start one, or just want to have a couple drinks with us, we’re totally game to listen and learn from your successes and/or failures.

  • http://howardkang.com/ Howard

    If Social Media has taught me anything about life, which it has, is that barriers of entry are low and we can crush it if we have the quality, work ethic, and bring people great value. I mean you’ve already been scrapping and working so hard, you should go for it if you really want it.

    You really gotta check Gary Vaynerchuk out!

    http://garyvaynerchuk.com/post/78962355/you-can-have-bothjobs

    http://garyvaynerchuk.com/post/78965849/doing-what-you-love-can-lead-to-more-then-just-happiness

    Knowing that and having the hunger help me put in the extra hours.

  • http://howardkang.com Howard

    If Social Media has taught me anything about life, which it has, is that barriers of entry are low and we can crush it if we have the quality, work ethic, and bring people great value. I mean you’ve already been scrapping and working so hard, you should go for it if you really want it.

    You really gotta check Gary Vaynerchuk out!

    http://garyvaynerchuk.com/post/78962355/you-can-have-bothjobs

    http://garyvaynerchuk.com/post/78965849/doing-what-you-love-can-lead-to-more-then-just-happiness

    Knowing that and having the hunger help me put in the extra hours.

  • Carly

    Hey Sydney! I really liked this post. I’ve been ruminating over very similar thoughts lately about starting a business – and whether or not I should find another day job, or working at a restaurant to get by while spending more time on getting things started. It is definitely a tough choice to make, especially when bills and rent and student loans start to pile up on your thoughts. Even still, I think your approach of setting up relationships with mentors and learning everything you can is great, and it feels like there is no better time to do something risky than now. The links you included were helpful too. Can’t wait to chat when you come visit NYC!

  • Carly

    Hey Sydney! I really liked this post. I’ve been ruminating over very similar thoughts lately about starting a business – and whether or not I should find another day job, or working at a restaurant to get by while spending more time on getting things started. It is definitely a tough choice to make, especially when bills and rent and student loans start to pile up on your thoughts. Even still, I think your approach of setting up relationships with mentors and learning everything you can is great, and it feels like there is no better time to do something risky than now. The links you included were helpful too. Can’t wait to chat when you come visit NYC!