How to Pick a Winning Venture with Serial Entrepreneur Alexandra Wilkis Wilson
November 4, 2021
Alexandra Wilkis Wilson, serial entrepreneur, investor, author and public speakerAlexandra Wilkis Wilson is a serial entrepreneur, investor, author, public speaker, and co-founder of Gilt, GLAMSQUAD, Fitz and Clerisy.

Her string of digital enterprises has distinguished her as a thought leader in the on-demand economy, artificial intelligence and machine learning. She has advised many new and developing businesses and served on the boards of public and private companies. She is the co-author of New York Times bestseller By Invitation Only: How We Built Gilt and Changed the Way Millions Shop and began her career in Investment Banking at Merrill Lynch. Clerisy is her latest venture, and together with Co-Founder Lisa Myers, Wilkis Wilson is building a $100M growth equity fund and leveraging her trailblazing experience and extensive network to support extraordinary entrepreneurs of consumer and techsumer companies. Below she shares critical business advice and how she picks which ventures to invest in.

You are a very successful serial entrepreneur. What’s the common spark between each new business that attracted you?

In all the businesses in which I was involved, we took an innovative approach to solve consumer problems and fulfill needs that hadn’t yet been met.

How did the success of Gilt Groupe open doors for the business endeavors that followed it? And did it open doors to the extent you would have expected?

The Gilt experience launched me into the public sphere as a well-known founder, a pioneer and advocate for supporting female entrepreneurship. My network was naturally stronger than when I first got started when I built subsequent businesses. I think it’s fair to say that investors and consumers paid more attention to me than they would have if I hadn’t had the Gilt experience under my belt. I am a go-getter, not afraid to cold call and reach out to strangers. I never expect success to just fall in my lap. I do my best to “go for it.”

I am a big believer in hiring talented team members who are problem solvers, action-oriented and self-starters by nature.

What inspired the name Clerisy, and how does your fund differ from others? What was the intention behind focusing on growth equity instead of the pre-seed or seed stages?

My business partner Lisa Myers came up with the name Clerisy for our growth equity fund. I love the name, which means a group of learned, collaborative people. At Clerisy, we are always bringing people together—founders, experts, investors, friends, friends of friends, the list is long! We invite all of these dynamic and diverse people to take a seat at the “Clerisy table.” Lisa and I believe there is white space in investing in the growth equity stage for consumer and techsumer companies. There are countless opportunities to invest in fast-growing companies that have established product-market fit but need both capital and hands-on guidance to scale. Our investor/operator approach at Clerisy has been well received by founders who appreciate it when we roll up our sleeves, get involved, open doors and help them.

How has your experience as a founder and operator impacted your approach as an investor?

I genuinely understand what founders are going through because I have been there and have sat in their seats. Founders usually appreciate that perspective and tend to let their guard down more because I have this experience myself.

What is the key to business growth? What advice would you give to a mid-stage founder on how to scale?

I am a big believer in hiring talented team members who are problem solvers, action-oriented and self-starters by nature. People with these characteristics can help enable a business to scale. If a team member is proving not to be a cultural fit or team player, or can’t be as nimble, scrappy and flexible as is required in a startup, then that person is most likely not going to work out as a long term, successful hire.

Any advice on finding the right co-founder? What is the best way to keep a good working relationship?

Find yourself a co-founder who has experiences, functional skillsets and a personality that complements your own. It’s important to have an open relationship with your co-founder where you can have tough conversations, and you motivate each other to perform at the highest levels.

Find yourself a co-founder who has experiences, functional skillsets and a personality that complements your own.

What is your best fundraising advice?

I have so much to say on this topic! My best piece of advice would be to do your homework on a prospective investor before you take his or her money. Investors do their diligence on founders. Similarly, founders should do their due diligence on their investors. It is important to gauge how that investor will behave in both good times and challenging times.

What is a business mistake you have made and what did you learn from it?

In a startup experiencing hypergrowth, it is very tempting to hire quickly, but that can lead to impulsive hiring mistakes. Hire slow, fire fast.

To what do you attribute your success?

Establishing goals for myself, being unafraid to fail and asking for help.

Who are some women on your radar?

So many! I love helping other female entrepreneurs whenever I can. More importantly, I appreciate learning from the new guard of founders!



/*video overlay play button*/