For the past two years I’ve been trying to get myself to attend one of DC–and the creative world’s–best kept secrets: Creative Mornings. On the last Friday of every month, Creatives from all over the world gather in their respective cities to hear ideas on a theme of the month. In DC Creative Morning RSVPs run out within minutes. Tickets are posted at 10am and if you’re not logged in and ready to RSVP you will end up on the waitlist. In May I finally got over myself and secured a spot. May’s theme was risk. Speaking on the topic was DC’s own Michale Lastoria, cofounder of &pizza–the best pizza shop in DC. He made for a great first impression. Lastoria spoke on creativity in risk in the most novel way. We don’t often associate risk with creativity, but on that morning he revealed how they are inextricably linked. The words I heard and the notes I took are slowly changing my relationship with creativity and risk. I’ll share some of what I learned below.
Quantity over Is Quality
Back in 2014, I recorded a voiceover for a video on the culture of my ad agency, LMO Advertising. One of the lines I read was “We believe there is profit in all work, because the more we do, the more we can do” I didn’t realize that I never fully understand this until I heard Michael’s talk. He opened his talk using Thomas Edison and Leonardo Da Vinci as examples. Edison owned over 2,000 patents and was behind numerous inventions such as the light bulb, the phonograph, the motion picture cameras and a stock ticker. Da Vinci was an artist, a philosopher, poet, and an engineer among many other things. “The most brilliant creative people are also the ones with the most output” he proclaimed. Even one of my role models, David Ogilvy serves as proof for this theorem. In addition to being an ad man; he was a chef, salesman, researcher, and entrepreneur with a brief tour of duty at the British Intelligence Agency during World War II.
For so much of our lives we’re told to focus–find one thing and apply ourselves to it alone. Ever since I was in high school I always felt that I had too much going on. I swam competitively, had a rigorous academic schedule, I was trying to become an Eagle Scout, and I was running a budding little candy business. This continued in college. No matter how much I tried to alleviate my workload, somehow I always had a packed schedule. Ironically, the times where I felt most overwhelmed are the times I felt the most productive and accomplished.
Lastoria makes the claim that the quantity of your works enhances the quality of your work. I’m inclined to agree. The more you do, the more data you have to store in the conscious and subconscious parts of your brain. This gives you more ideas to choose from to solve problems. I’ll take it a step further and say that Lastoria’s concept of quantity applies not only to outputs, but to inputs as well. Consuming ideas, content, and experience enhances the quality of our work. Steve Jobs often cited calligraphy, Buddhism, and the Beatles as inspiration for Apple’s culture and the design philosophy of its products. The best musicians are known for listening to a wide variety of music outside of their respective genre. Combining ideas and experiences from many practices with our subconscious’ current database inhibits us to make many abstract, long-distance connections. To be creative, we have to act on these bets and take the time to work through our ideas. The more we train ourselves to act on these ideas, the more we’ll create.
Reward v Belief
During his talk, Lastoria explained how changing his relationship with risk changed his relationship with business. Typically, we appraise risk based on the value and probability of the reward. We ask ourselves: “is it worth the risk?”. However, Lastoria challenged us to use our beliefs to appraise the value of a risk. If every decision is a risk, the question to ask becomes: ” Do I believe in this decision?”. If the answer is yes, then acting on that belief is no longer a risk– it is a necessity. “I needed to execute on this vision because to not do so would have been a loss” Lasoria said of his desire to leave New York City to start a pizza shop in DC.
In the short-term acting on the bets we make in our head is risky, but we don’t regret failure or that an idea didn’t work, we regret inaction. We regret not trying. However, the risk in front of us often paralyzes us when in reality, these risks can be our greatest advantages.
The biggest risks are your biggest advantages
Before closing out his talk, Lastoria got vulnerable as he shared his biggest causes for doubt and ultimately the biggest risks of starting a pizza shop in DC. Prior to starting &pizza in 2012, Lastoria ran (and still runs) a branding agency In New York City, he didn’t come from the restaurant business. His amateur status as a restaurant owner led him to build his business based on his experience as customer. Rather than acting as someone who sees tables as dollar signs on a floor plan, he built &pizza from the customer’s vantage point.
Leaving New York City for DC–a foreign city– was a big risk. However, New York has a saturated pizza market and DC had no emotional connection to pizza, presenting with a huge opportunity for &pizza. While these competitive advantages may not have been obvious at first, he discovered them by acting on the bets he made in his head. One of my favorite examples of this was when he spoke of his fear of the “uncool”. Few entrepreneurial fantasies feature a pizza parlor as the dream. We tend to shy away from the uncool, but it’s where some of the greatest opportunities lie. The acceptance of the status quo among current players and the perceptions of consumers provide us with an opportunity to bring disruption and stand out. &pizza,Warby Parker, Zappos and Apple are all examples of this. By daring to enter the “unsexy” spaces of pizza, prescription eyewear, online shoe sales, and hardware these players have each redefined their fields.
Lastoria’s talk was a big wake up call for me. It reshaped my thinking on creativity, risk, and work. As I build up my entrepreneurial confidence and tolerance for risk, it might change my relationship with business as well
Lastoria’s full talk can be seen below.
youngrestlesscreative.com 
3 thoughts on “Lessons From My First Creative Mornings”