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The Key to Success Is Finding Your Trouble

Recently, a budding entrepreneur came to me frustrated that there was so much for him to do before he could even think about starting his business. Antonio said he needed to save up enough money, quit his job, do market research, develop a business plan, write a pitch deck, design a logo, get an office, hire employees, develop an advertising plan, etc. His thinking was when he had everything on his list checked off, then he could press “go” on the business.

This is a very common perspective — that we can only be successful if we have all of our ducks in a row before we start. But the truth is, you don’t need to have all of your ducks in a row to be successful. You only need to have the right ducks. And there are fewer of them than you might think.

As we talked, I told Antonio the story of a little coffee shop located in San Francisco called Trouble and how Giulietta Carrelli got it started.

Before opening Trouble, Giulietta had been a barista in many coffeeshops over the years. One day, her boss suggested it was time for her to open up her own place. She found a tiny store front the size of a one-car garage just blocks from the Pacific Ocean and secured it. With little startup money, Giulietta used found objects, tree trunks, driftwood, and plants as the decor. She also asked favors of her friends to help her fix up the place for opening.

The wooden benches encouraged patrons to share seating, rather than pairing off at tables. Giulietta liked that this facilitated communication between her customers and created a cozy, community feel. The menu was spartan, too; being limited to drip coffee, young Thai coconuts served with a straw and a spoon for digging out the meat, shots of of fresh-squeezed grapefruit juice called “Yoko,” and toast with butter and cinnamon.

Giulietta chose these items because they have special significance in her life. To her, the coffee represents speed and communication (like the furniture). The coconuts and the grapefruit juice on the other hand, represent survival. Theoretically, one can live off coconuts as long as you have some source of vitamin C. In fact, before founding Trouble, Giulietta tested this theory for three years when she was in and out of homelessness. Finally, the toast represents comfort and family to Giulietta. Growing up in Cleveland, her Italian immigrant family didn’t eat much standard American food. The exception was cinnamon toast, which was their American comfort food.

Beyond being connected to Giulietta’s life experience, she says these menu items helped ground her, as well as feel connected to and remember who she is. Trouble is authentic to her and its unapologetic honesty was like a beacon into its Outer Richmond neighborhood that attracted lines down the street.

Today, Trouble still does not have any tables or chairs. The atmosphere of Trouble is not only a safe haven for Giulietta, it’s also sustainable both ecologically and economically. Giulietta started with the core items she felt were needed for her to open a coffee shop, and it turns out that’s really all her customers were looking for. She didn’t need fancy espresso machines, swanky furniture, advertising or even a detailed business plan. All Trouble required to get started were the basics, a few customers and some word of mouth.

When many of us contemplate building a business or making a big change in our lives, it feels risky and unsafe. So, we tend to wait until we feel completely secure in our decision before taking the plunge. Usually this means taking more time than we need to make preparations, and waiting around for the “perfect time” to press go. All of this time spent planning and preparing can give us the feeling of being in action, of accomplishing something without actually taking any risks. Our perfectionism can become a sophisticated form of procrastination, and usually by the time we recognize it’s the perfect moment, we’ve already missed the window.

Instead, many of the most successful ventures get started the way Trouble did. They start with the minimum required to begin building revenue and a customer base (in agile development, this is referred to as the Minimum Viable Product, or MVP). Then they watch their customers and the market for signals on where to focus next.

Over the years, Giulietta has expanded the coffee menu from drip to a variety of espresso drinks. The menu’s broader too, including local pastries and three more versions of her now famous toast. I’m willing to bet, the impetus for adding these items came because they helped her customers feel more welcome and comfortable at Trouble, not because Giulietta thought she “needed” them to succeed.

Had Giulietta waited until she had a financial backer, the perfect location, or the perfect time, Trouble and the artisan toast trend it inspired may never have happened. Now, maybe the world doesn’t really need hip coffeehouses around the country selling $4 toast. But it can always use a little bit more Trouble.

What kind of “trouble” are you waiting around to get into? What conditions or requirements have you put on this dream that’s got you in a holding pattern?

Make a list of everything you think you need to do before you can move forward. Then cross off anything that is not absolutely, 100% essential and see what’s left. Is this your Minimum Viable Product? What’s one action you can take this week to make this vision a reality?

“Start by doing what’s necessary; then do what’s possible; and suddenly you are doing the impossible.” — Francis of Assisi

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