A Q&A with Alexandra Wilkis Wilson, 3-time co-founder, 2 exits, and a new Miami-based fund

If you like to shop for designer clothes at better prices, get your hair and makeup done in the comfort of your home, and have your closet organized and your outfits styled, you’ve probably heard of tech-enabled companies such as Gilt, GLAMSQUAD, and Fitz. What you may not know though, is that they were all co-founded by a Cuban-American woman who was born and raised in New York City and who recently moved to Miami.
I’m talking about Alexandra Wilkis Wilson. Wilson, who sold both Gilt and Fitz and moved to the Magic City in June 2020. Her latest “baby” is a growth fund called Clerisy, where she and her business partner, Lisa Myers, invest in sectors they have expertise in.
Gilt sold to Rue La La for $250 million and Fitz sold to Tradesy, a company that counts Richard Branson as an investor.
I talked to Wilson to learn more about her move to Miami, her latest venture, and her tips for founders, both in terms of building a business and what kind of deals Clerisy is looking for.
What brought you to Miami?
My husband and I moved here from New York with our 2 kids in June 2020. My mother is Cuban, and while I’m only 50% Cuban, I feel 100% Cuban. I grew up spending the summers in Key Biscayne – which is where we live now – so Miami has always played a role in my life and it was always on our radar. We just couldn’t figure out how to make it work with our careers. On a social level, we’ve had many friends here for a really long time, but over the last 6 months, we’ve seen more people moving here from New York and San Francisco, too. I think we’re going have a second wave of movers when school ends, because they’ll have time to get their kids set up for the next school year. I speak 5 languages – English, Spanish, Portuguese, French and Italian – so one thing we’ve always really liked about Miami is the international aspect.
Can you tell me about your most recent role before starting Clerisy?
I was SVP of consumer strategy and innovation at Allergan — the global pharmaceutical company — where I led new efforts in revolutionizing digital marketing and DTC initiatives for Allergan’s leading aesthetics portfolio including Botox, Juvederm and Coolsculpting. *Allergan was then acquired by AbbVie for $63 billion.
Can you tell me more about Clerisy?
Lisa is based in the Bahamas and I’m based here, so we really view Miami as our headquarters. She brings the investor expertise and I’m the one with the operator background – the investor-operator duo is unique. We’re a growth fund investing in companies with more than $10 million in revenues who are looking to scale, and we usually invest in consumer-facing tech. These companies already have product-market fit and they’re looking to grow. We’re particularly interested in health + wellness, beauty, and the commercialization of healthcare. I’ve worked on a lot of different companies in my career, but the thread has been that I always targeted the same consumer. She shopped on Gilt, got her makeup done with GLAMSQUAD, and had her closet organized with Fitz.
What do you wish you had known when you started your first company?

  • Entrepreneurship is a roller coaster. You can have the highest highs and the lowest lows.
  • It’s more of a marathon than a sprint.
  • Scaling takes time and it puts pressure on the company, on the people, and on the systems.
  • It’s important the founders spend time and energy doing due diligence on their investors, especially if the investors are taking a board seat. If there’s synergy between the investor and the founders, it can be magical.

What’s some general advice you have for founders?

  • Always think ahead, including in the hiring process, because when you need someone, you need them now, but it can take a while to find the right person, so you should be meeting potential new hires along the way.
  • Similarly, build other relationships before you need them, be that with investors or potential acquirers.
  • Keep your eye on the cash and always know how much runway you have left.

What’s some advice for founders who are looking to build and then exit?
I think it’s helpful to have possible strategics tracking you and your growth. And if they are looking at your company as a possible acquisition, keep in mind what’s important to them. It’s not to say, necessarily, that you’re going to build your business around it, but I found it helpful, personally.
What are some of the things you’ve seen done well when companies pitch you?
It shows when the founder really knows the business and has a strong handle on the metrics, and is also passionate about the brand and the vision. It’s compelling when we get the whole package.
I also really like founders who are transparent. A lot of founders like to sugarcoat it – and I get that – but most investors don’t want to hear that everything is rosy if it’s not.
What are some mistakes that you’ve seen so far with teams that have pitched you?
A lot of companies that have pitched us that are too early stage. It’s not a mistake, it’s just a timing issue. But I actually really like meeting founders early and watching them scale.
How quickly will you close on a deal?
It depends if the founders and management team have all the data we need upfront when we meet. Clerisy is very thorough.
Does Clerisy lead rounds?
Clerisy will always lead rounds in which we come in and we’ll always take a board seat and a board observer seat.
To contact Clerisy, email: [email protected]
An earlier version of this story contained an incorrect acquisition price for Allergan.
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Marcella McCarthy