Here’s to Keeping It Real

My girlfriend has grown impatient with my lack of progress.  We have no doubt hit rock bottom.  I say that this is rock bottom because no matter what I can wait tables anywhere and sustain this level of existence and unless I commit a felony I can always get a job waiting tables somewhere.

Today I submitted a couple of ideas I’ve had rolling around in the back of my head for a while to a fast pitch event that connects entrepreneurs with angel investors.   I bounced some of the details of my ideas off her and she was clearly annoyed by it.

Tonight we had a good talk after a few drinks.  We started out talking about her goals.  She’s at that point in life when she realizes she is going to have to make a decision about what she wants to do with her life but hasn’t found her calling.  I can relate because I’ve been there.  I try to be sensitive but I also try to challenge her to think it through and work the problem without talking down to her, making her feel stupid, or pissing her off.  Usually I piss her off.

As usual the conversation turned to me.  What have I accomplished?  Why am I so special?  She is reserved and it’s rare that she opens up about what she really thinks although I can usually tell what she thinks before she admits it.  I love the real conversations.

She admitted that has grown impatient and weary of all my ideas.  No surprise to me because it’s no secret that she wants to get married, buy a house, and start a family.  She feels that every new idea means failure of the current idea and further delay.

She came at me hard.  She said that as this drags on she increasingly doubts that I will be successful.  I can see why she thinks that.  She sees other guys my age with stable salaried careers.  I tried to defend my choices by arguing that the experience I’ve gained is far better than any of our peers/friends who have chosen a stable career.  I added that although I they may seem better off right now, in the short run, in the long run I have better positioned myself for greater success.  She countered, “why do you think you’re so special.”  Using my own words against me.

It cut deep but strangely I loved that with one simple question she was challenging everything I believe in, everything I’ve ever done, and everything I’m striving for.  It forced me to do some soul-searching.  Why am I special?  Damnit, I’m special because I have ideas, the courage to give them a go, and some savvy to execute them.  Instead of wavering I am now even more entrenched in my conviction that building my own successful business is my path to happiness.

But how do long do I have before she leaves me?  I have always wondered but never asked.  Given her rare brutal honesty it seemed like time to ask so I did.  She roundaboutly said 5 years although I suspect it’s really much less.  Judging by her increasing impatience and frustration I give it 2 years at best.  Can’t blame her, wouldn’t blame her, that’s just real.

It’s tough to swallow when those closest to you don’t think you’ll succeed and may leave you if you don’t.  On the flip side, I am more motivated and energized to make something happen and for that I am grateful for her brutal honesty and implicit challenge.  If she continues to challenge me in this way it will be far better than her benign complacency, pretending to listen or care about my latest idea.

Here’s to keeping it real.


Inspiring Others

One of my friends at work is a beer enthusiast, or more appropriately a certified beer expert.  It’s her passion and she lights up whenever we talk about it.  She has accumulated a vast body of knowledge of all things beer; pairings, cooking with beer, beer history, glass ware science, hops, and brewing techniques.  She is one of two women in the entire state that is a certified brewer and she is plugged into the beating heart of the beer culture in this town.  It pains me that she is stuck working in this restaurant and I can tell it pains her.

Yesterday we were talking and she began telling me that she wants to move to a bigger city and find a job in a micro brewery, preferably a brewer position.  Then she told me that although she enjoys making the beer she likes educating people about beer the most.  What she really wants is to have a job where she just talks about beer all day, like a beer historian, or consultant.  I asked her then why the move and why wait?  You could do that here, tomorrow.  I threw some rough ideas out about how she could make money doing that as a consultant to restaurant owners and maybe eventually opening up her own micro brew that focuses on a unique beer experience and the history behind beer.  She instantly lit up but then just as quickly began to tell me all the reasons it couldn’t work.  I knocked down all her objections one-by-one and layed out the model for how she could give it a try for less than $200.  It’s basically the same model for how I started Digital Whale.  It’s pretty much the same type of business just different subject matter.

She realized that she doesn’t have much to lose except her time and as she put it, she has lots of time.   She was inspired and you could see the pistons pumping in her head as she vowed to put some stuff together.  I can’t wait to see what she comes up with.  Her passion for beer is exceptional and I bet her ideas will be too.

Her inspiration was infectious too as I look down the barrel of week two of January with my goals in the sights.  I keep wrestling with the idea of starting a failure club or group for young entrepreneurs.  Although I know I don’t have the time to devote to it this month, hopefully I can make that one of my monthly goals soon.

Good Talk

I have become increasingly isolated since I have had to cut out all of my social activities.  I talk with people at work and my girlfriend at home but it’s mostly small talk.  There isn’t anyone around me other than my dad who enjoys chatting about business, politics, or philosphy.  Since he’s been pretty busy this year, I often yearn for a stimulating conversation.

Two nights ago I stopped off at a friend’s pub for a cocktail on the way home from work.  I sat next to a couple guys at the end of the bar who were watching the football game.  One of them had a laptop and appeared to be working on something in between watching the game and carrying on conversations with the guy next to him and the couple in the next chairs over.  Towards the end of my drink, just before asking for my tab, we struck up a conversation.  My curiosity getting the best of me I asked him what he was working on.  It turns out he was writing content for his website and is one of the most respected and well known writers on FCS level football.  He and his buddy were in town for the weekend covering a game.

We found common ground on blogging, the trials and tribulations of entrepreneurship, the rise and evolution of the internet, social media, content creation, finding a niche, and such.  It was the best conversation I had in months.  I gave him a few tips on how to promote his new site and business through social media and I gained a bit of wisdom, perspective, and inspiration through listening to his stories about the last twenty years of his career.

You never know who you might meet.  I realize now that the social isolation I have resigned myself to is perhaps doing me more harm than good.  I need to meet new people to build up my network and to find like minded people just for the sake of conversation if nothing else.  After Christmas I will try to go out for a drink or two at least once a week and try to meet as many people as I can.  If my finances allow I’ll join a new pool team or dart team too.  I also have this idea to start some sort of group for entrepreneurs that has been rolling around in my head for some time.  Perhaps I’ll finally pursue that as well.

We all have read stories about the eccentric and determined entrepreneurs who literally live in their office and do nothing but work around the clock to create the next big internet start-up.  That type of commitment is inspiring but I would argue that for most entrepreneurs it is not the best path.  What was I thinking I could create a social media marketing business without being social myself?


He ran for state legislature and lost.

Then, he started a business and failed.

He ran for Congress twice and lost both times.

He ran for Senate and lost.

He ran for Vice President and was defeated.

He ran for Senate again and wasn’t elected.

In 1860, he was elected the 16th President of the United States.

Abraham Lincoln.  Imagine if he had given up.