I don’t like gambling. It’s out of character for me. No, not at the casino, but by pursuing my passion and resigning from a great job. After contemplating for months if  I should go all in, I decided to pack up my entire apartment and move 3,000 miles back to my childhood bedroom.

I knew if I didn’t take a chance, I would regret it for the rest of my life.

I cashed in my entire life savings, took my seat, and put my chips on the table. I sized up my opponents and tried not to break a sweat. In this card game I chose, I’m up against world-class wine industry giants, who have been at it longer than I’ve been alive. During my first handful of months as the CEO / Winemaker of RedHead Wine, these are four important lessons I’ve learned:

  1. Entrepreneurship isn’t solitaire, you shouldn’t do it by yourself!

I wasn’t single when I started RedHead Brands: I was in a committed relationship with my business.  It was just the two of us, but I realized it wasn’t working.

I thought I would have an Olympic gold-medal-worthy swan dive into the cutthroat world of competition. But the reality was more like me breaking my neck in the “no diving” section of a kiddie pool.

So much to do, only 168 hours each week to do it.

Little did I realize just how much there would be to do. Or that hours would disappear in minutes. Countless days were consumed by meetings, attorneys, permits, potential partnerships, budgets, presentations and more. I decided to systematically find others to help me divide up the work, so I didn’t feel like I was failing at something I wanted so desperately.  

Now that I have more “players” on my side, I am starting to feel like I am getting somewhere with RedHead. What a world of difference it has made for me!  It really is okay to admit you don’t know something and to reach out for help.

There are an enormous number of resources available for startups and young companies regardless of where you live – don’t be shy about tapping into them.

  1. You can create your own kind of “beginner’s luck” with what I call “unintended consequences.”

It’s almost eye-roll worthy when I hear myself say, (echoing Woody Allen) “Half of success in life is just showing up,” but it is so unbelievably true.  Get involved in the community, but ALSO make sure you have a positive attitude while doing it.  The more visible AND visibly happy you appear, the more people will be willing to talk to you and learn about what you or your business offer.

In addition to doing the usual things – going to business meetings and networking events – it’s important to discover new opportunities.

A recent example: I was at the Fort Lauderdale airport busy eating Bare Baked Coconut Chips as if my life depended on it. (side note: My love for anything coconut is borderline crazy). I hate eating on planes and wanted to get my snack in before I boarded when suddenly, a gentleman who sat near me asked if I was heading back to Pittsburgh.

I could have blown him off and been like “yes” and quickly start texting to avoid further conversation, but I decided to learn more about him and his story to pass some time. He told me he and his partner recognized me from the flight down (the bright side of having red hair and wearing a highlighter pink track suit).

Through this totally accidental meeting, I learned his family owns malls and restaurants and expressed interest in getting RedHead into them!

The unintended consequence? Being visible and noticed can give you a breakthrough for your business if you are open to them.

  1. Keep your poker face on, take your time and do your research.

I have a flaw that I’ve been working on. I’m gullible and show my emotions, or what I like to say is that I easily trust people. This is interesting since I know many people have “trust issues.”  

“If I trust you, you can trust me.” – sounds like a good mantra to live by, right? Wrong.  In business, this is NOT best practice. Having an overly trusting attitude has hurt me more times than I want to admit.

I don’t want you to think that you shouldn’t trust anyone, but take your time and do serious due diligence and research on everyone you consider using for their services – whether it’s a consultant or a player you may want to add to the game. I didn’t do this very well with a few people and ended up getting more burnt than a marshmallow engulfed in flames at a campfire.

The best way to find out if a working relationship is good for you is to observe carefully when interviewing and to ask for references. Find out exactly how helpful the person you are researching was to other businesses and what they did for them. Googling social media may be great, but nothing replaces interviewing someone in-person to see if they’re the right fit. Signing a contract they construct usually protects them and NOT you.

  1. Move the chips to the side and stand out from competitors with unexpected personal touches.

This point might seem trivial but being unique and different is how to garner attention. I personally enjoy thinking outside the box and use creativity for business and in my personal life.

Examples: instead of showcasing a picture of myself dressed up, in heels doing a dirty job necessary for the business or instead of showing a picture of RedHead wine displayed sitting on a table, I display it upside-down.  

Once in a while – do the unexpected like writing a person a note instead of just sending a text or e-mail.  In this technology-filled world we live in, creating a personal connection can be a challenge. Develop your story and be original. It’ll go a long way.  

This is what I learned my first year in business. I’m sure there are more lessons to come.

Here’s what I know: if you play your cards right, have a great attitude and remain authentic and honest with yourself, you too, will find success at the dealer’s table.

When the feeling is right – throw all the chips in and go for it.  If not, get out of the game.

Want to connect? You can reach out to me on Twitter here.

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