Harley Finkelstein and Lindsay Taub : for the love of Montreal 

Harley Finkelstein is a great entrepreneur and the CEO of one of the biggest and coolest tech companies in the world: Shopify. Shopify is worth $150B+ in 2025 and is unquestionably one of the greatest successes in the tech world—and it happens to be a Canadian company! He also started the Big Shot podcast, which showcases inspiring stories of the greatest Jewish entrepreneurs. Their stories are so inspiring and the podcast is one of my personal favourites. Lindsay Taub is a professional psychologist, mother and philanthropist. Together, they have built a unique and strong partnership and purposely chose Montreal as their home. 

I personally have loved Shopify as long as I can remember, but I only heard about Harley on my way to a commercial mission in Paris in 2023 listening to the podcast Diary of a CEO. That same day, I fell in love with the mission, the drive and what Harley stands for. When I heard the tech giant was moving to Montreal with his family, I was astonished: THIS guy, choosing MY city!? So, I reached out. Many times (lol). Finally, we met for coffee. We bonded over food and restaurants, over our shared passion for entrepreneurship and building things that matter, and our love of Montreal. It has been 18 months since Harley moved to Montreal, and I have had the pleasure of spending some amazing quality time with him and his wife. They are both wonderful people, they both fight to build amazing things, they both are huge foodies, and they both love Montreal. 

What’s great about them is that they truly invest in our culture: they dine out, explore, and support local restaurants with both their time and money. They quite literally put their money where their mouth is! A conversation with a power couple I admire. 

Where are you both from?
Lindsay & Harley : We are both from Montreal but initially met in Ottawa. — For a little backstory, Harley’s grandparents were immigrants in the 1950s, and his grandfather started an egg stall at Jean-Talon Market called La Capitaine. The stall is still owned and operated by his family. 

How did you meet?
L : We met through speed dating (haha!) It was a leap of faith, stepping out of our comfort zones, but we knew each other already. Interestingly, we did not match at first. Harley called me later, and we went on a date. The rest is history.
H : Our relationship is built on teamwork. We strongly believe that the structure of a team matters, whether in romance or business. A partnership thrives when both individuals share a common vision of success. We both live meaningful lives and approach everything with intention—nothing happens by accident. 

Why did you choose to live in Montreal?
We love Montreal’s culture. We love the multiethnicity of this city. The fact that it was built by immigrants. It’s a diverse city with a rich heritage, an incredible restaurant scene, and a vibrant arts and music culture. We always say: go where the poets, DJs, chefs, and artists are—that’s where real culture is. And that’s Montreal. It is a beautiful chaos and that is where the magic happens. The entrepreneurial spirit in Montreal is infectious. It’s a city filled with ambitious people who want to be the best while staying true to themselves. We love that about Montreal. The city gives energy. 

Cooking & Dining

Do you cook at home? What’s your favourite dish to make?
H: Lindsay cooks!

L: I cook a variety of dishes, but my favourite is Ina Garten’s roast chicken covered in butter. It’s a staple, especially with two little kids at home.

You favourite type of cuisine?
L: Italian-Mediterranean, but I would say Italian!  

H: Japanese. I appreciate the flavours, the preparation, and the aesthetics of Japanese cuisine, especially the beautifully designed bars.

Tea or coffee?
L: Both. There is a time and place for both. We love coffee but Harley also started a tea company. 

H: Coffee in the morning (Xbloom – sold on Shopify 😉 and green tea (Firebelly – my new company) in the afternoon.

Sweet or savoury?
Savoury, always. Bread and butter over everything.

What are your favourites restaurants in Montreal? 

H & L : For a cozy Japanese haven, Kitano Shokudo is perfect. We love Hiroshi (the owner and chef). Otto Yakitori is always fun and delicious, and Sushi Nishinokaze is one of the best restaurants we’ve ever eaten at.

If you’re looking for a French-inspired dining experience, Le Chien Fumant and the new Rôtisserie La Lune offer something exceptional.

Joe Beef and Liverpool House are true Montreal institutions, known for their unique culinary experiences. Tavern on the Square, with Steve and John at the helm, is a fantastic place to visit, even on a Monday. The vibe at Gibbys St-Sauveur is incredibly cozy, making it a great escape for a comforting meal.

In what we would call the ‘flavor explosion’ category, some of our favorite places include Beba, Oncle Lee, and Kam Fung, each offering a distinctive experience.

Damas is a favorite for its consistent quality, always delicious dishes, and a beautiful terrace. Bistro La Franquette is a standout neighborhood restaurant where the quality of the food speaks for itself.

As for the new delights in our culinary adventures, places like Café Gentile never disappoint. Romies, with its New York City polo club atmosphere is always so fun and delicious and La Spada with its warm and inviting ambiance, both offer a similar vibe where you instantly feel comfortable.

L : Olive et Gourmando is one of my favourite lunch places, especially the new location at Royalmount. The vibe is casual and homey but the food feels very gourmet. The tofu noodle salad is delicious and feels very healthy so I come back to it again and again!

Foxy is also definitely a hidden gem. Every time I go there I am truly blown away by the service, the quality of the food and the lively but loungey atmosphere. Best martini in town. 

The best restaurants strike a balance between a lack of pretentiousness, high-energy vibes, and exceptional food quality. And that is Montreal. Montreal is truly an “if you know, you know” city. There are so many hidden gems waiting to be discovered. It is a city full of secrets – it is an open secret, but still.” 

A restaurant on your bucket list?
There are so many! Au Pied de Cochon, Club Chasse et Pêche, and Hoogan et Beaufort are high on the list.

Where do you take an important client in Montreal?
Liverpool House is quintessentially Montreal. The vibe, wine selection, and diverse menu make it the perfect representation of the city. And Chris (Morgan) is quintessentially Montreal too!

Montreal’s Business & Entrepreneurial Scene

What do you like most about Big Shot? What are you learning from this adventure?
H : I never idolized athletes growing up but rather collected news clippings of entrepreneurs. Big Shot is an archive of the greatest entrepreneurial jewish minds, capturing their stories. Many of these individuals started from nothing—some were refugees who built legacies. It’s an honor to share their journeys. At the end of the day, these multi-billionaires all share the same recipe for success: sharing your life with a truly great partner. 

What’s the best advice you’ve ever received?

L : Believing in yourself, trusting your voice, and embracing learning moments lead to a richer life.

H : Failure is simply the discovery of something that didn’t work. It provides insight for the next opportunity. 

How would you describe Montreal in three words?
L : Beautiful chaos, grit!
H: Joie de vivre!

Where do you see yourself in 10 years?
Still in Montreal, continuing to grow, explore, and contribute to the city’s evolving landscape.

Any final reflections on Montreal?
Montreal is the greatest city on the planet. We will always be its biggest cheerleaders, and we believe that anyone choosing to live here should do the same. It’s a city that fuels ambition and passion, where creatives, chefs, and innovators thrive. Entrepreneurs shape the fabric of our city, bringing innovation and vision. It is the city of entrepreneurs.  

Written by Élise Tastet