A Startup Guy

There’s this image out in the world of the lone entrepreneur anonymously toiling by himself, carving the next great company out of the wilderness with his bare hands. I admit I’ve held that image myself. I think it comes from the stories we hear as kids of Americans being rugged individualists.

But the image isn’t really true. People who accomplish great things, including business startups, do it with help. Lewis had Clark. Hewlett had Packard. Robert E Lee had Stonewall Jackson. Larry Page has Sergey Brin (and Eric Schmidt).

You don’t have to have partners, but you need someone to talk with. Someone you can bounce ideas off of. Someone to brainstorm with. Someone to be an advisor. Someone to call you out when you do dumb stuff. I think author Keith Ferrazi has a new book out about this, Whose Got Your Back.

I spent years trying to go it alone, without much help, advice, support or feedback. It sucks. Don’t do it that way. As I’ve considered this situation I’ve come to realize that I’ve got to get out in the startup world. Mix it up with the upstarts out there. (I really want to name a startup “The Upstarts”!) Find people I can collaborate with, exchange advice with and, sometimes, just shoot the bull with. So I’ve created and scheduled an event named Startups Over Coffee. it’s similar to groups like Geek Breakfast and Startup Drinks, and we’re going to meet at 9am on Saturday, July 11 at Fido coffee shop on 21st Avenue in Nashville. If you’re into startups and in the area, come on by. We’ll be meeting and mixing with other startup enthusiasts. Come share some ideas and grab a great cuppa joe. Who knows what might come out of it.

We’ve already got some smart people signed up for the event and I”m excited to see what happens.

Meeting New People is Fun!

Being shy, especially those of us who are painfully shy, is not conducive to business leadership. It holds legions of people back from achieving greater success. It’s also incredibly hard to overcome. In an article titled Bashful in Business, the Financial Times reports that there is evidence that this “social awwardness” can be overcome with practice. Evidence Sir Richard Branson, who admits to being shy, but has overcome to lead one of the largest brands on the globe. He’s everywhere, including on television.

I’m incredibly shy. Put me in a room full of people and I’ll usually clam up. I don’t know what to say or how to say it. When we’re going to a social function, my wife will usually look at me just before we arrive and say, “Now, you HAVE to talk tonight. People will think you just don’t like them.” That’s not the kind of personality you want running your company or even some department inside of it.

However, over the last several years I’ve finally started coming out of my shell. It’s tough. It’s emotionally draining. It’s also worth it. At each event I attend, I make it a point to meet new people and get myself embroiled in conversations. Inside I’m screaming, “Let me out of here!”, but at each event it gets a little easier. At last year’s BarCamp Nashville, I interacted with lots of people. I was a virtual freakin’ social butterfly compared to how I normally am.

Here are 8 things that have worked for me and may help you start to overcome your shyness:

1. Use online social networks as a way to get to know people you will be meeting at real-life social functions. (Beware! Many of us use services like Twitter to allow us to interact with others without having to meet them in person. Don’t fall in that trap!) Before I attend an event like PodCamp or BarCamp, I always check out who of my tweeple (Twitter people) will be there. Then I encourage them to say hello to me. Talking with people I know helps me to open up and prepare to talk with strangers.

2. Have some questions ready to ask people. I think many introverts are like me and our brains freeze when we enter a social situation. We can’t quickly come up with conversation topics or even simple chit-chat questions. So in my mind I’ve got a few points mapped out in case I panic and freeze. It’s usually simple stuff like, “What do you do for a living? What part of town do you live in? Are you married? Do you have kids? What are you favorite TV shows? What is your opinion of PHP vs. Ruby on Rails vs. ASP.NET?” (I threw the last one in to see if you were still awake!)

3. Find common ground. Use questions like the ones listed above to find a topic of common interest that you feel comfortable talking about. Once you get on a topic you’re knowledgeable about and comfortable with, conversation comes easier.

4. If the conversation begins to get awkward, end it gracefully. If the discussion starts to die and those awkward silences are coming back, don’t feel badly about breaking off the conversation to go do something else. “Hey! It was nice talking with you. I’m going to go scout out a place to plug in my laptop before the next session gets going.” Also, don’t take offense if someone else breaks off the conversation and moves on. They’re socializing and meeting new people too.

5. Invite people to contact you later. “If I don’t see you again before you leave today, be sure to shoot me an e-mail and we can talk some more.” If you like the person you’re talking with, always encourage them to contact you later to help build a relationship. The point is to foster social interaction and meet new people. I have a tendency to feel like no one’s really going to want to talk to me later, they have more engaging people to talk with, so I wouldn’t offer my business card or give them my e-mail address and invite a follow up. Turns out, that tendency is wrong.

6. Find a wingman. It sounds a bit silly, but this can work. Find someone who is better at socializing who will hang out with you for a while at the social event. They can help break the ice and keep conversations going. It needs to be someone who understands that you’re shy and need some social guidance. However, you cannot talk only to this person and ignore everyone else. That won’t get you anywhere. You also need to participate in all conversations. Don’t just stand there and let your wingman do all of the talking. Be willing to break away from them after a while and fly on your own.

7. Take baby steps. You’re not going to be a social butterfly your first time out. Keep your expectations realistic, but be willing to push your boundaries. As you get more comfortable, push your boundaries further. It’s the only way to grow.

8. Take time to decompress when it’s over. “Being on” is tough on most people. It’s exhausting for those of us who are incredibly shy. When the event is over, make sure you get some quiet time to recover, even if it’s just on the drive home.

Overcoming shyness, introversion, social awkwardness, bashfulness or whatever you call it takes a lot of work, but it can be done. And the rewards can be great. Don’t let it hold you back in business (or life)!

Do you have tips on overcoming shyness? Leave them in the comment section.

I’ve had (have) several blogs over the past few years, but most of them related to specific websites I had started. This one is different. It’s mostly for and about me. I got tired of restricting what I said to the “subject” at hand. I needed some place to write what I wanted to write about. So, here you are.

Mostly, this blog will cover business startup info, marketing, history and anything digital that interests me, but I may also stray into whatever other shiny things catch my eye. What’s in it for you? A wild ride. So, hang on…!