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Warning! This post is going to be a little different.

Photo credit: Ryan McGuire of Gratisography

I hope by now you don't get the mistaken idea that I have all the answers..

While I'm doing the best to share what I've been learning about creativity and its relation to being an entrepreneur, I'll admit that I still struggle myself with not only learning these lessons but more importantly living them.

Over the years I've helped entrepreneurs and wannabe's with everything from simply getting started to taking their first baby steps - to building teams and social media and even ultimately selling their businesses.

The only rule is that there really are no rules - or let's put it another way. What works in one set of conditions won't necessarily work - even when everything seems the same.

As much as I believe in always doing what we can to learn from "failures," sometimes you just salvage what you can out of a situation and walk away with that box of unused file folders and highlighters that might come in handy.

More recently, I've been experimenting with writing / blogging and posting on social media while testing online chats like Hangouts on Air and even Meerkat, Periscope and now -

Why am I doing this? With the limited success of past launches I'm working to build a deeper relation with my audience - my 1000 True Fans.

Meanwhile, on the more "creative" side of the spectrum I'm working on some fiction and interactive media including a Twine game.

It's not easy to do these things while doing freelance work and earning whatever income I can to keep food on the table. Nope, sorry - no rich spinster playing sugar momma to this creative.

Recently, I've been listening to Elizabeth Gilbert's Big Magic where she shares how she did what she could to keep writing.

"I wrote my first book while I was a diner waitress. I wrote my second book while I was a diner waitress and a bartender. I wrote my third book while I was a bartender who also worked in a bookstore and who also worked as a journalist. When EAT PRAY LOVE (my fourth book) came out, I was still working at a flea market on weekends. If it wasn't for the bananas success of EAT PRAY LOVE, I would still be doing other jobs."

Gilbert implores us not to depend on our art to pay the bills - until it does.

In other words, as she puts it - “To yell at your creativity saying ‘You must earn money for me!’ is sort of like yelling at a cat; it has no idea what you’re talking about all you’re doing is scaring it away, because you’re making really loud noises and your face looks weird when you do that.”

So, while I'm saying that creative entrepreneurs need to play it safe - in fact, I've been thinking about the advice that Jim Carrey gave at commencement speech. Like the best poker players make sure the odds are your in favor, but don't play with your rent money!


Nothing like graduation.. and in the commencement speech the mayor of your city confuses the name of your engineering college for that tech school. You know the one that airs those cheesy commercials in the middle of the day..

Yeah, to this day I don't remember anything else the mayor said but I still remember the collective groan and wave of cringes that echoed in that auditorium.

I don't know about you but these are the commencement speeches that I wish I had heard before going out into that big wide world after college..

First up, of course, is the one and only Steve Jobs addressing the Stanford graduating class of 2005 who shares his journey as a creative entrepreneur and how "you can't connect the dots looking forward, you can only connect them looking back.."

Next is author / artist Neil Gaiman who I recently learned about from his relation to Amanda Palmer and got highlighted on Brain Pickings -

Last but not least is comedian Jim Carrey who shares the tragedy of his own father's dream that got left behind in choosing the safer route -

So, what I find the most inspiring is the advice that no one really knows anything, and you need to do what you can to practice your art - your craft. Most of all you have to be willing to fight for that right because no one else will do it for you.

Which commencement speeches have you found to be most inspiring for creative entrepreneurs? What do you wish someone had told you as you graduated?

Making our way through the pile of chairs in the narrow hallway hours before lunch service began, the worker finally pointed to the makeshift shack hidden behind the restaurant. I thanked him and knocked on the door. It all felt like some Prohibition era speakeasy.

photo: Blue Bottle Coffee

A bright-eyed man with glasses invited me in. He looked like one of those musicians who you couldn’t tell their age because of the gray hair and youthful features.

“What would you like?” he asked.

“I don’t know - what do you suggest?”

“Well, if this is your first time, I’d recommend the Guatemalan medium roast. You can’t go wrong.” He hands a brown paper bag to his partner.

“Sounds good,” I replied.

This was the early days of Blue Bottle. A coffee roaster filled up the room barely the size of a single car garage. From these modest beginnings grew a caffeinated empire that now spans across the Pacific.

In February of this year they opened their first store in Japan to lines around the block. Only a few months later they began a second store. Meanwhile, in June they raised $70 million in funding.

What struck me about Blue Bottle from that first bag to the last drop I've enjoyed so far is the attention to detail and quality. You known when you drink a cup that this ain't your neighborhood Starbucks.

At the center of this is James Freeman who started what some have called the “Apple of the coffee industry.”

“I think Apple has been really influenced by the very rigorous simplicity of a lot of Japanese design elements and their focus on simplicity and quality. I'm obviously very influenced by those things too. Apple's doing it for the world; we're doing it in twenty stores. Lessons are lessons,” says Freeman.

Freedom to Take Creative Risks

While it’s easy to point to success and oversimplify the process of getting there, Freeman was well aware of the risks and went into this with eyes wide open.

“If we were going to make a big mistake, I wanted it to be my big mistake, not anybody else's big mistake. I wanted to be more responsible for all the details and I knew there would be more risk because we might have gotten it wrong—and that's expensive,” he said.

Finding the Right Creative Team

For the missing pieces of the business DNA that Freeman felt they needed, Blue Bottle acquired several key players including San Francisco bakery Tartine.

“If you could have the world's best croissants, why not? I've known Chad (Robertson) for a long time. He's been wanting to grow, but he hadn't found the right team. Then he was here when we opened. The first week, he saw how well the team here was working with this launch, as well as the incredible demand, and that's when he said he found the team that he wanted to work with.."

"So much is about the team," Freeman says, "because these are people I’ve got to see every day or every week—so it has to feel like it's a natural fit. It's not just about how much money we're going to make, or real estate or anything like that.. It's all about who we want to work with.”

Be Willing to Play the Long Game

Although Freeman wants to expand more quickly, he realizes that quality takes time. Blue Bottle now has twenty stores with ten more coming. "We're getting better and better at it," he says.

"The store feels a certain way because we really care about things; like how the doorknob feels when you walk in, as well as what you see, and how the light shines in the pastry kitchen. It takes a lot of time to do that."

I love a nice latte for a bit of liquid inspiration, but these are just some other bits of creativity that you might find in your next cup.

Quotes are from Toyokeizai - (Part 1) (Part 2)