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Start-Ups: The Best Rush Imaginable by Alexandra Wilkis Wilson

Start-Ups: The Best Rush Imaginable by Alexandra Wilkis Wilson

Start-Ups: The Best Rush Imaginable by Alexandra Wilkis Wilson

Employee Emeritus Employee Emeritus ‎10-19-2016 07:46 AM

Alexandria Wilkis Wilson (2).jpgHaving been active in the start-up trenches for the past 9 years of my career, I can honestly say that there is nothing like the thrill of being a part of a start-up in hyper growth.


Many people often say that entrepreneurship is like a roller coaster, and I couldn’t agree more. There are people who love roller coasters and want to ride them again and again. I’m one of those people. I love the crank part of the ride when reaching the tippy top, because it is filled with anticipation, excitement and the unknown. There’s no turning back at that moment you reach the top. The next few minutes are entirely out of my control and yet feel strangely safe to me. Strapped in, it feels like a calculated risk, not a reckless one. Going down in a roller coaster is the really fun part. I like to scream as loud as I can with my hands in the air. Often I laugh uncontrollably, tears in my eyes from the wind, or from joy, possibly even fear? It is such a rush to go zooming downward at 60+ miles an hour, then back up again slowly, only to confront new twists and turns as the ride continues.


Entrepreneurs will experience some of the highest professional highs imaginable. I have experienced the rush of conceiving of a new business, building the infrastructure and operations, creating the brand, raising capital, launching the business and then scaling it. There is nothing like it. Launching a business with an extraordinary team is an incredible adrenaline rush.


However, I would be remiss if I didn’t acknowledge that with those highest highs, come the lowest lows. Start-ups can be emotional. Entrepreneurs can take things personally and in a start-up, things will go wrong—you can pretty much count on that. In those moments when things don’t go according to plan the entrepreneurial “gods” really test us. Can we keep our cool under pressure? React quickly? Be flexible? Own up to our mistakes and learn from them? Embrace setbacks, small or large, to make us stronger and more successful in the long run? In fact, I believe if a start-up isn’t making any mistakes, then it probably isn’t taking enough risks and moving fast enough. Speed plays a necessary role in a start-up. Sometimes you have to be first to market, not necessarily perfect.


In all of the startups I have been involved in directly (Gilt and GLAMSQUAD) or indirectly as an advisor, angel or mentor, the businesses that scale fastest are the ones who push themselves the hardest to a place or a goal that is often uncomfortable and surrounded by uncertainty.


I am a big supporter of entrepreneurship, especially of encouraging female founders to take risks and to think big. I want to help increase the chances of success for more businesses. I would like to see more founders raise capital for their start-ups. I have seen many start-ups fail, not because they were bad ideas, rather because of lacking execution of the ideas. We all have ideas! But how can we turn those ideas into viable businesses?


I would like to highlight some of what I’ve learned in the near decade I have spent in start-up land, experiencing highs like meeting Madonna and enduring lows like suffering from ongoing migraines.


I recommend that if you are an entrepreneur, you be able to describe your start-up in one sentence. Practice, practice, practice explaining your business to others.  Simplify the one sentence company description. It should roll off your tongue and be easy for you to share, not cause you to take a deep breath and cross your fingers hoping that your audience will “get it”. Test your one sentence out on loved ones and ask for feedback. Often loved ones can be your toughest critics—that’s ok. They care about you and want the best for you. Tell them to “talk to you straight”. Don’t let them sugarcoat. Can they repeat the one sentence back to you? You never know when you’ll be asked to describe your business. It often happens unexpectedly, so be ready. Never miss an opportunity to pitch your business.


Building the team for your start-up is probably the most critical aspect of creating a business from scratch. Hire for intelligence, passion and relevant experience. A candidate with raw smarts and relentless drive can learn on the job, so I am sometimes open to putting candidates in roles that don’t 100% correlate to their past jobs. I like hiring people who have a track record of dedication and success. Hire remarkable people and together your team will achieve remarkable things.


I have only founded businesses with co-founders, never alone. I have relied on my co-founders, trusted them, respected them and learned from them. I know I would be lonely and less effective doing a start-up by myself, largely because I love being part of a team. My energy and creativity stem from being stimulated by others, rather than operating in a vacuum. Know yourself- your strengths and weaknesses.


Through a career coach named Barry Carden, one lesson I learned in my early Gilt days is to avoid the temptation of hiring similar people. It will increase a start-up’s chances of success to have a diverse team. There are many lenses through which to hire for diversity; one lens we used at Gilt was the Myers-Briggs test. Ideally your start-up team consists of varied profiles. This will help set your team up to be high-performing, equipped to handle challenges.


Creating a culture from Day 1 of a start-up is very important. Certain aspects of a culture may not be scalable from 10 employees to 100 to 1000, so focus on the elements you intend to keep throughout your company’s trajectory.


I have never liked the word “networking” but I believe in it. I think of networking as building authentic relationships over the long term. Some people are naturally prone to meeting new people and connecting with them. If you are comfortable doing this, embrace this as a gift. If you aren’t comfortable building and maintaining relationships, push yourself. Your relationships are valuable and are yours to keep. No one can take them away from you.


Make time for self-reflection. Recognize what you have learned from previous work experiences and concentrate on what you should carry forward to your next role.


The start-up landscape has changed a lot since we launched Gilt in 2007. New York now has a legitimate place on the map as being a city for entrepreneurship, with an ecosystem of successful entrepreneurs and venture capitalists. I am thrilled to see more women creating disruptive companies that have changed industries and consumer behavior. I feel so fortunate to be a part of this community of supportive founders sharing and learning from one another every day. I have several mentors in my life who have been there for me in pivotal moments in my career. I similarly do my best to share many of my lessons learned with fresh entrepreneurs as they come out of the gate, bright eyed, filled with passion and a touch of endearing naiveté.  


In my upcoming Verizon Webinar, I look forward to sharing in greater detail my thoughts on these topics including my personal checklists on how to hire effectively, how to create a company culture, how to lead a team and how to build and maintain your network effectively.


-For more thoughts on entrepreneurship from Alexandra Wilkis Wilson, you can look for her book written with her Gilt Co-Founder Alexis Maybank in 2012 called “By Invitation Only: How We Built Gilt and Changed the Way Millions Shop” (Penguin/Portfolio).

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