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How to Pack Like Tech Entrepreneur Anthony Lacavera

Roll, fold or stuff? We caught up with Anthony Lacavera before a business trip to London.

Anthony Lacavera

Ten years ago, looking to shake up the telecom industry, Anthony Lacavera founded Wind Mobile, a wireless carrier that offered affordable mobile plans. Since then, he’s focused on moving Canada away from traditional industries, like fossil fuels, by investing in tech start-ups. Now, he’s taking on blockchain and artificial intelligence: His new venture, Globalive Technology, works with companies like VIDL, which uses both technologies to report breaking news. We caught up with him before his next business trip to London.

Scrunch, roll, fold or stuff?
I roll everything, even suits. And I always have plastic bags in my carry-on, for shoes and dirty clothes.

What’s exciting you in the start-up world?
Artificial intelligence. Canada is a global leader in AI; we’ve invested in it smartly over the last 30 years. I mentor entrepreneurs who are developing early-stage AI through Creative Destruction Lab, which helps to scale Canadian start-ups. We lose great tech companies, like Nortel and Research in Motion, when we don’t sustain them at a global level.

What do you look for in entrepreneurs before you invest?
Relentlessness, perseverance, discipline and consistency.

When do you unplug?
On long-haul flights. I like to listen to music while I’m watching movies – so I can see the films, but can’t hear them. I’ll make a playlist for a 15-hour flight with DJs like Calvin Harris, Tiësto and Paul Oakenfold and play it non-stop.

You have your pilot’s licence. Where is your favourite place to fly?
The Hamptons on Long Island. It’s super aviation-friendly and it’s beautiful in the summer. My plane’s home base is Toronto’s Billy Bishop Airport and I mostly fly to Boston, Montreal, Chicago and New York. My daily life involves tons of calls and meetings, so going up in the plane is an amazing escape.

What's in the bag of Anthony Lacavera

I’ll put on one of these 24K Gold Hydrogel Masks from Toronto-based Victoria Radford during a long flight. It’s supposed to go on for 15 minutes, but I leave it on for an hour – it has eyeholes, so I can watch TV.

Emperor’s Clouds and Mist from Teavana is my current go-to, but I make a point of trying different brands because there are always new green teas coming out.

I’m constantly on the lookout for unique sunglasses and watches, the only two accessories I wear. Chrome Hearts’ designs are so detailed; they’re the best I’ve found.

These dress runners from Louis Vuitton are a little pricey but extremely comfortable and great for both daytime or evening events.

I always carry it with me because I never know when I might need an escape route via air. Too bad I can only fly a single-engine airplane – that won’t get me very far!

This Christian Louboutin wallet is the perfect size for travel: It’s small and compact but holds everything I need.

For all of the guys out there who don’t use cream because they think men don’t need it: You’re wrong! Olay Eye Gel is amazing for brightening up travel-weary eyes after a red-eye flight to Europe. I use it every day now.

My Audemars Piguet Royal Oak Offshore watch is the most versatile one I own. It’s dressy enough for a suit, but works well with jeans, too.