Photo above: 2014 Endeavor Gala at New World Center in Miami Beach. Photo Courtesy Endeavor Miami. 

At Endeavor Miami, we like to highlight the stories of high-impact entrepreneurs to inspire others to thrive on their own. We are looking forward to giving the first IMPACT Award to Alexandra Wilkis Wilson co-founder of GLAMSQUAD and Gilt, and Jim McKelvey, co-founder of Square and LaunchCode, two entrepreneurs leading successful careers.

During my work at Endeavor Miami, I’ve found that entrepreneurs may feel very lonely at times, though the ride itself is very rewarding. With the support of leaders such as Alexandra and Jim, who go beyond their own companies to help other entrepreneurs, that same ride seems easier. Endeavor has been great at engaging world-class business leaders, entrepreneurs and investors around the world to support emerging entrepreneurial ecosystems. It is really rewarding to see the ecosystem grow here in Miami. In that spirit of highlighting the stories of great entrepreneurs, Alexandra and Jim share their insights on commonly asked questions. We hope you find their words and advice encouraging as you continue to thrive.

Endeavor Miami Gala will unite 300 global business leaders and influencers in celebration of high-impact entrepreneurship on Nov. 18. We hope you can join us.

Alexandra Wilkis Wilson, co-founder of GLAMSQUAD and Gilt.

Q: What does high-impact entrepreneurship mean to you?

A.W.: High-impact entrepreneurs pursue ideas and visions to create companies that have a significant impact on creating jobs and opportunities for a large number of people. I believe these businesses typically disrupt the incumbents, and are by nature innovative and relevant to today’s changing society.   

Q: What advice would you give to an entrepreneur who has good traction and wants to scale?

A.W.: Build the best team possible. Find individuals with skill sets that aren’t your strength and who have a different Myers-Briggs profile than you do. Diversity on teams is an asset.

Q: What does it take to be a good leader?

A.W.: A good leader connects with diverse people, inspires them and unites them to accomplish greatness. A good leader is not afraid of adversity and can demonstrate grace under pressure.   

Q: How do you define yourself in terms of your entrepreneurial abilities?

A.W.: I am a doer. I like variety. I like engaging with people every day. I like to sell, and I believe that I can do that authentically. Entrepreneurs need to be able to sell their vision to team members, investors, clients, partners every single day. I think the ability to be able to sell is often overlooked in the startup world. If I had a start-up super power, it would be the ability to “sell.”

Q: Do you have any role models?

A.W.: I have many role models, beginning with my parents and expanding to many great entrepreneurs, corporate executives and people who are not afraid to push boundaries, who are resilient in the face of adversity. Some of these are people I actually know well and can go to for guidance, others I have just watched from afar and have served as inspiration for me to achieve and push forward.

Q: You first went to learn about fashion before jumping into entrepreneurship; what was the defining moment?

A.W.: I guess the defining moment for me was the day of our first live sale on Gilt: Nov. 13, 2007. Zac Posen was the first brand we ever sold. Our founding team had no idea what to expect that day, but as an entrepreneur, you learn to expect the unexpected. Fortunately, it was a very good day and the start to something that truly disrupted consumer behavior as well as the fashion industry. 

Q: From Gilt to GLAMSQUAD: How is this new venture different for you as an entrepreneur and CEO?

A.W.: This is the first time I am a CEO, so that is different, exciting and very motivating. I was only 30 years old when we started Gilt, but now I have years of experience under my belt, and also as an adviser and a mentor to many startups that I have supported along the way. I am trying to channel all of my learnings to apply what is most relevant to GLAMSQUAD. 

Q: What tips can you give other entrepreneurs on how to select and manage relationships with co-founders?

A.W.: Communication is very important. I am a big believer in having an executive coach. Our management team at GLAMSQUAD recently went on an executive off-site together, something we used to do periodically at Gilt. The purpose of the off-site was to create a dynamic of open communication and trust so that we can ensure we have a high performing team. We used Myers-Briggs as a framework. 

Q: What are your ties to Miami and where do you see Miami’s entrepreneurial community?

A.W.: My mother is Cuban and I have been coming to Miami, specifically Key Biscayne, since I was a baby. Miami has always been a big part of my life, I even got married in Coral Gables back in 2007. I am on the board of Perry Ellis which is headquartered in Miami. One day, I hope to move full time to Miami. I have seen a lot of progress in Miami’s entrepreneurial community in recent years, thanks in large part [to] the great work of Endeavor, eMerge [Americas], Knight Foundation as well as groups like Rokk3r Labs and Büro’s office sharing spaces. I think all of the cultural advancements in the arts have also played a positive role in Miami. 

Q: What’s the value of Endeavor in Miami?

A.W.: I see Endeavor in Miami as a gateway between American and Latin American entrepreneurship. There was a need to build more startup friendly infrastructure in Miami and Endeavor is taking this on and making significant progress.

Q: What advice can you give to entrepreneurs in Miami who want to thrive in an emerging ecosystem?

A.W.: Get out there and meet new people! Relationships matter! Encourage people to move to Miami! Help recruit engineering talent to Miami! It is paradise after all and shouldn’t be a hard sell.

Q: What’s the best advice that someone has given you?

A.W.: I often tell people, “If you don’t ask, you don’t get.”

Jim McKelvey, co-founder of Square and LaunchCode.

Q: What does high-impact entrepreneurship mean to you? J.M.: Entrepreneurs are the change agents. A high-impact entrepreneur eliminates a significant problem in the world. Q: What advice would you give to an entrepreneur who has good traction but wants to scale? J.M.: Resources for good ideas are plentiful, but people with the energy and skills to execute those ideas are more rare. Focus on the team.  Q: What does it take to be a good leader? J.M.: A good leader inspires others and provides a sense of purpose for what may seem like routine tasks. Q: How do you define yourself in terms of your entrepreneurial abilities? J.M.: I’m an optimist who believes any problem can be solved.   Q: Do you have any role models? J.M.: I’ve always admired Edwin Land and Nikola Tesla. Q: You are an artist and a serial entrepreneur; what was your defining moment? J.M.: I’ve had several, but perhaps the first major one was when my first company was failing and I deicided to work alone until I could get everything resurrected.  Q: From Square to LaunchCode: Why? Are there any differences in the entrepreneurial abilities you’ve used to spearhead both? J.M.: In both cases, my work was convincing people to believe in a better way. At Square, we challenge the biases in the financial system; at LaunchCode we challenge the biases in employment and education.    Q: What tips can you give other entrepreneurs on how to select and manage relationships with co-founders? J.M.: Choose a co-founder with a complementary skill set. Q: What are your ties to Miami and where do you see Miami’s entrepreneurial community? J.M.: My wife and I could live anywhere, and we chose Miami. This is much more than a party town, and the energy and open-mindedness of the population is infectious. Q: What’s the value of Endeavor in Miami? J.M.: It’s fitting that a worldwide organization like Endeavor would choose our most multicultural city to open its first U.S. location. Q: What advice can you give to entrepreneurs in Miami who want to thrive in an emerging ecosystem? J.M.: Travel. Q: What’s the best advice that someone has given you? J.M.: Don’t just learn how, learn when. Advice from Lino Tagliapeitra (the world’s best glassblower).  

The Endeavor Miami Gala will take place on Wednesday, Nov. 18, from 7:30 to 10:30 p.m. at New World Center, 500 17th St., Miami Beach. Tickets are $500 each and can be purchased at endeavorevent.com. Proceeds from this event directly support Endeavor Miami’s mission to select, mentor and accelerate high-impact entrepreneurs in South Florida.  For more information, visit endeavorevent.com or email [email protected].

Photo: 2014 Endeavor Gala at New World Center in Miami Beach. Photo Courtesy Endeavor Miami.