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Caroline Wozniacki Is Our Next Great Tech Investor

And other lessons from the 166 accounts she follows on Twitter

Musto Design
Musto Design

Caroline Wozniacki is ostensibly a professional tennis player. She’s currently the 74th-ranked women’s tennis player in the world, and she has advanced to the third round of the U.S. Open. [Update, 1 p.m. ET: Fourth round!] Great job, Caro! If you were ever the single best person at a given thing — and Caroline was; she was ranked no. 1 in the world back in 2011 — that thing would likely define your identity (at least publicly). But this Woz, whose tennis abilities are in decline, is clearly looking ahead, beyond her playing days. A broken engagement to Rory McIlroy, a tight friendship with Serena Williams, modeling, and zero Grand Slam titles will not be the epitaph for this great Dane. Based on her Twitter follows, I feel comfortable saying that Caroline Wozniacki is preparing to embark on a second life.

Woz follows 166 accounts. She joined the service back in 2009 and has amassed 1.19 million followers since, though she has tweeted only 4,507 times. That averages out to 1.83 tweets per day since she joined, which is a civilian level of tweeting. Tennis stars — they’re just like us. Woz’s Twitter usage rating is not insignificant when you consider how many hours per day she must spend without her phone in hand (because she has a two-handed backhand) and beyond the proximity of a laptop. Plus, she’s a Dane who travels the world for her craft, and she owns homes in New York and Monaco (at least), so she must be changing SIM cards all the time — another barrier to frequent tweeting. But communication is important to her, which we know based on her role as senior editor at Derek Jeter’s Web Anthology of Personal Essays and the fact she often punctuates her tweets with emoji. Why limit yourself to words when there are so many ways of expressing how you feel and what you see?

Her embrace of the platform and emoji is not surprising when you take a closer look at who she follows. There are a few discrete groups among the 166 accounts (which is quite low for a seven-year user), and I consider a perusal of this list tantamount to looking into a crystal ball showing Woz’s future. Amid the 140-character missives and heart-eye smiley faces, there are clues to be read. Like a college senior at a career fair, Woz is using Twitter to figure out what comes next. She’s curated her follow list to serve as a casual window into various endeavors she could pursue.

Here are the options:

1. Keep on Modeling

Caro was part of the body paint portion of the 2016 Sports Illustrated swimsuit issue. She’s got the experience here. And she’s very pretty, meeting American conceptions about Norwegian aesthetics perfectly. The only problem here is she’s already 26, positively ancient by industry standards. The models she follows — Karlie Kloss, Kate Upton, Gigi Hadid — are all younger than her. Sorry, Caro. You need to get more creative.

2. Become an Actress

Caro was recently on an episode of Ballers, and she follows the Rock.

He has 10.5 million followers and is one of the most bankable actors working today. Of course she follows him. Learn from the master. I’m not sure acting is where her passion lies, though. Her other significant Hollywood follow is Doug Ellin, creator of Entourage. I’m sure Caro loved the early seasons and Mandy Moore’s extended cameo just as much as we all did. But a true thespian is not relying on Doug Ellin for a big break. Doug Ellin is who you turn to when you’re walking along the beach of Hollywood, allowing your legs to get wet but never taking the plunge. Caroline doesn’t really want this life.

3. Buy a Majority Stake in ‘The Players’ Tribune’

She’s already a senior editor. She’s on the board, whatever that might mean. She follows Hannah Jeter (wife of founder) and noted contributor Kobe Bryant. She’s embedded in this world.

But she’s written (“written”) only three pieces so far. Kobe has written 11. Maybe her Players’ Tribune board work requires her to stay late talking about the editorial direction of the publication. Or maybe she’s still fighting with developers after the site crashed on both Kobe and KD’s big days. But still, that kind of written output doesn’t indicate the kind of commitment this career path requires.

Also, she doesn’t follow Derek Jeter.

4. Become an Angel Investor Specializing in the Tech Space

Yes, this is the most unexpected move, but I think it’s where her heart really lies. She already follows these accounts: Mark Cuban, Uber Support, Bill Gates, former tennis player turned investment banker Mario Ancic, senior VP of shop.com and self-described “Successful Internet, Cosmetics and Fashion Entrepreneur” Loren Ridinger, and noted actress-turned–business woman Jessica Alba. All of these people are polymaths dabbling in many fields — just as Woz is already doing. Woz has an advantage on so many new billionaires, because she already has multiple residences and therefore several options of places to hide cash and evade taxes. Kobe (reminder: she follows him) is laying the blueprint for the athlete-to-investor transition already.

The main requirement for the tech option is to have a lot of money. As a highly successful tennis player who has parlayed her fame into modeling gigs and who knows what other for-profit ventures, Woz has a lot of money. If she uses some of the liquidity to surround herself with savvy advisers and experienced operators, she’ll have no trouble succeeding.

The immediate course of action for the Woz is to pare back her 166 to a deliberate 125. Get rid of accounts like UberFacts and OMG Facts and Girl Dictionary. These are just distractions when you could be figuring out your entire next life. Maybe add a few media accounts like Wired and Recode to get a grasp of the landscape. When losing in the late rounds of international tennis tournaments gets old, she’ll be ready.