Confidence Meets Chutzpah, a Tale of Entrepreneurship

, CareerConfidence Meets Chutzpah, a Tale of Entrepreneurship
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One morning, after returning from a week in Las Vegas for a big event, I had an epiphany; it was time for me to start my own business. It was the calling I had longed for since my days as a neighborhood door-to-door saleskid.

I’ve always had the entrepreneurial spark. Growing up, I was master of lemonade stands, and once, even took our golden retriever door to door and trained him to perform tricks in exchange for payment. That day I took home a Tupperware full of loose change, an orange, and a box of matches (by the way, who gives a kid matches!?!?!). As an adult, I fell in love with an amazing career in event management, but never reached a point where my confidence met my chutzpah enough to fuel the fire of entrepreneurship. Until one day in April 2018.

But first, let me take a step back to explain how I got there. Several years ago, after working for over a decade on the agency side in Chicago, I decided to try my hand on the brand (a.k.a. “client”) side of the business. I took a giant leap of faith and moved to Boston for a role leading reunion events at Harvard Business School (HBS). It was a refreshing change from the nonstop pace of agency life, with just two events each year, a 9-to-5 schedule, and few (if any) emails streaming in on evenings or weekends. Being on the client side was an incredible experience, even though it took a while getting used to being the client rather than serving the client. I loved the people and the work, but deeply craved the adrenaline rush and the high-energy environment of agency life, so I returned to the agency world as the Director of Events in the Boston office of a global experiential marketing agency. The company was incredible, and our team was full of all-stars, but I began having visions of running, designing, and producing exceptional experiences and memorable events end-to-end and I knew I could bring the capabilities of a big agency to companies of all shapes and sizes.

Working on the brand side empowered me to lead teams while doing the work I love, but it wasn’t enough of the intense rush that feeds my drive and passion. And then chasing the action I craved on the agency side stripped me of end-to-end control over the project I wanted to bring to my clients – new ideas, innovative experiences, creative tactics, and new ways of connecting with customers. I became increasingly motivated to define my place in the events world – to realize my purpose – harnessing the collective experience leading up to this point. So, I dedicated every waking moment to creating something special.

Enter my epiphany moment. Arrow Events was born.

Throughout my career, I’d considered starting my own business; and once, about ten years ago, even tried my hand at freelancing. So, why now? Why after these years was the time right to blaze my own trail? I think for the first time ever, I realized that the culmination of my diverse background on both the agency and brand sides could translate to profound value and an elevated experience for my clients. For the past 15 years I have walked in the shoes of the agencies and brands and could bring a 360-degree appreciation for the challenges of designing and delivering exceptional events and experiences. I know what brands go through when planning make-or-break events for their most important customers and stakeholders. Likewise, my agency experiences gave me the complete playbook for how to do things right, right from the very beginning. I created a vision for a company that is laser-focused on brands looking for a full-service agency at a price point that can match any budget. Armed with a global network, I knew I had the ability to scale teams of designers, AV experts, event managers, and more, to suit my clients’ needs – anywhere in the world, any time. The time was right, and I made the leap.

The idea of creating Arrow Events was exhilarating and terrifying, yet I knew I was ready. My confidence and chutzpah kicked in and I sprang into action doing what I do best: planning! I spoke with a friend and former colleague who had done something similar and she shared her experiences and lessons learned about life as an entrepreneur. I assembled a team of mentors and advisors who were (and continue to be) invaluable in helping me navigate the risks and obstacles of creating a competitive company capable of making my clients’ visions a reality. I dove into the details of planning my financials, marketing plan, delivery capabilities, operations, and legal aspects of starting a new venture. I even spent the better part of a week brainstorming website names and contacting the owners of unused domains to see who might release their hold for less than $10k (spoiler alert: nobody!).

There were a million other things keeping me busy in those very early days. But eventually, with my business plan in-hand, and with support from a handful of potential clients, I felt ready to give notice at work. For almost a month, I spent the days transitioning out of my full-time job and spent evenings bringing my business plan to life.

It wasn’t easy, and success didn’t come right away; and frankly, it’s probably way too early in this journey (almost six months in!) to say that I’ve made it. At the very least, I’m making it, with business booked through April and a backlog of events forecasted even beyond that. (Can I get an amen!?) But it was hard and stressful and scary at first. Before I had even launched, a couple of friends shared my new venture with their contacts. Almost immediately after launching, I got a large contract and was on cloud nine. However, several days after submitting my marquis proposal, instead of receiving a countersigned contract, I got an email letting me know the client had decided to manage the project internally. Par for the course in this business, and totally understandable, but a little disappointing for a budding entrepreneur.

Two weeks later, I received my first signed contract and was elated! This was shortly followed by another new client and then ANOTHER! With each win, I celebrated. With each disappointment, I pushed harder and learned even more from it. Along this journey, a friend told me that in the life of an entrepreneur, the lows are low, the highs are high, and they happen way more frequently than you’ve ever experienced before. This statement is so real, and I think about it daily, usually during a high moment. Since making this brave (if I do say so myself) and purposeful career transition, my days have been filled with happiness (okay, some stress), wins (okay, some losses), and PROGRESS. Starting a business is not for the faint of heart, but I wouldn’t trade this adventure for anything.

I look back on that post-Las Vegas day in April with a smile on my face and optimism in my heart. It was the day that changed my life. I made the calculated leap and it has proven to be one of the best decisions and most rewarding professional experiences of my life…well, except for my brief stint as a door-to-door golden retriever trick performer. But who can live off loose change, an orange and matches?

I dedicate this, my first-ever professional blog post, to my mama, who told me from the beginning that I should start my own business and call it Arrow Events. Moms know.

About Emily Olson

Emily Olson is Founder, Principal and Executive Producer of Arrow Events, an Event Management Firm in Boston, Massachusetts. Emily is known for her no-nonsense, results-oriented mindset and readiness to try anything twice. She brings her sense of humor and a human element to creating memorable events, and is inspired by the quote, “They may forget what you said; but they will never forget how you made them feel.” When she’s not creating magical event experiences, you might find her on a mission to find the best pork bun in Chinatown, watching superhero movies, or traveling around the world. Follow Arrow Events on Instagram, Twitter, and Facebook for event inspiration, tips, and best practices! Emily can be reached at emily@arrow-events.com.

Photo Credits: Emily Olson and agencyEA

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By |2018-11-19T21:54:41+00:00November 20th, 2018|Categories: Business, Career|Tags: , , |

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