Retail Online Training


As a child, Samir Kulkarni was always surrounded by business with his family.

It seemed only natural that the current CEO of retailer Showcase would end up running a business one day. 

Kulkarni was born in Brampton, Ontario. He received a Bachelor’s Degree in Philosophy/French at York University then an MBA in Strategy/Finance at Yale University.

“I grew up in a business family. I was mentored by my father and my uncle almost from when I was born and actually used to go with my father to business meetings from age eight onwards. Every weekend and every holiday I would spend time with him and my uncle at the office and so my career ambition was to always join the family business which is a group of different businesses and help the family in some way. That was always the ambition,” he said. 

“During my undergrad, I actually was running one of the businesses full-time and really didn’t have much of an undergrad experience as a student because I was really working non-stop and then went to Yale and did my graduate school and became a true student there.”

Samir with family 1983 – Samir (center front) at 7 years old, with mother Bakula (left), Kiran (right), and sister Sonal (center back). Samir was immersed in the family business from the beginning, learning under his father in business meetings from age 8 onwards, while Samir’s mother mentored him in languages and arts. Samir’s sister Sonal studied the law and today is Showcase’s corporate counsel.
Samir Appleby 1984 + Kids 2023 – Samir (left) attended prestigious boarding school Appleby College in Oakville ON during 1984-1993. Coming full circle, his kids Arjun (center) and Karishma (right) were accepted into and enrolled at Appleby in 2023

Kulkarni said the family is involved in many different sectors including manufacturing, financial and tech. 

“We’re a pretty diversified conglomerate but the business I’m involved with, Showcase, was actually not part of the group as I was growing up. It only came available for investment as I was finishing up school. So as we were acquiring that business that’s when I got involved. That’s where my focus has been with the group.”

Showcase was founded in 1994. The Kulkarni family invested with the original founder in 1999 as Samir was finishing business school. He came back to Canada and has been driving the business forward since then.

“It was a very contrarian decision at the time because all of my classmates were going off into management consulting and the dot com boom was started then in the late 90s or going into investment banking,” said Kulkarni. 

“My training is in finance and investment management and so on. Retail was definitely an unconventional move but what has been really interesting is to look at what used to be an old world business of retail and how really the old world and the new world have come together with technology, with social media, with pop culture. We’ve infused a lot of new world technology into what we do and so it’s really become a new world business in that way and the old world and the new world have sort of come together to create a really interesting business model.

“A few people were probably scratching their heads back in the early days, now it all makes sense and it’s come together and has become a really interesting modern business.”

Samir Breakfast Television 2013 – One of Samir’s early television appearances, introducing Showcase’s products on Breakfast Television with Dina Pugliese in December 2013.
Samir with Showcase leadership team 2015 – Hosting the ribbon-cutting of Showcase’s new head office. Leadership team Greg Synowicki (left), Samir (center left), founder of Showcase Amin Jivraj (center right), and Rob Watt.

When the family looked at Showcase, it was a very unique business model. Not a typical retailer. It is able to identify trends and commercialize those trends immediately.

“Think of us as a real-time trend store of whatever is hot on maybe television, on radio and these days on social media,” explained Kulkarni. “So that was what was intriguing. We are selling the products that everyone wants that no one can find and they want a storefront to be able to go to buy them.

“That’s what makes us different than retailers selling commodities.”

Chrystia Freeland Meeting Oct 2022 – as a member of the Board of Directors of Retail Council of Canada, Samir travelled to Parliament Hill to meet with Deputy Prime Minister Chrystia Freeland, Minister of Innovation Francois-Phillipe Champagne, and Deputy Minister of Finance Michael Sabia.

Kulkarni said data is his passion. He looks at different data sets every day with the Showcase team.

“There are simple sources of data. For example, going on TikTok and watching TikTok for an hour. I do that probably more than I should but I spend a lot of time on social media as a daily routine. But it’s also looking at other data sets and seeing what people are searching for, what people are tweeting about. I love to go through reams and reams of data and try to help find that next big thing.

“Data is a big part of what I do. In the old days, I used to travel a lot more. I used to travel to China, meeting with vendors, traveled to trade shows. I don’t do that as much now. It’s become much more of a data driven business. So I spend a lot of my time in front of a computer.”

Samir + Divya – TIFF 2023 – Samir and his wife Divya Kulkarni walk the red carpet at TIFF 2023, being long-time supporters of the festival.

Outside of work, Kulkarni is passionate about playing billiards. In his younger years, he was a competitive player. He didn’t turn pro as he got into the retail sector. 

“But it’s certainly a passion of mine and it’s something I spend a few minutes every day playing and it’s a game I feel I understand. I’m also a big squash player. I’ve been playing for 40 years. I make time for squash every week,” he said.

“I started playing pool in high school. I remember through university I was playing 20 hours a week of pool. It was a very serious endeavour. What I like about it is that it is mathematic and controllable and it’s about geometry and logic and I love those topics. That’s probably why I play squash as well. It’s a square box where the ball is going to bounce in a predictable way and that’s why I gravitated to those sorts of controlled fun as opposed to golf which I’ve also tried which is not controllable at all.”

Kulkarni described his leadership style as being all about speed and entrepreneurship, spotting the opportunity in things and pivoting very quickly based on new information.

“We have set up our corporate culture in that way where we try to remove bureaucracy, red tape, layers of approval and things like that. And we try to make decisions very, very quickly. So people have information at their fingertips, they’re encouraged to try things, to experiment. Failure is not a problem. Failure is just a delayed success. We encourage people to roll the dice, try things so that we can learn quickly and so in terms of my leadership I try to encourage those parts of our cultures because that’s really what makes Showcase work.”

Image: Showcase

His passion today which he tries to spend half his time on is Artificial Intelligence.

“I’ve been working on AI in a very big way for the last year and a half. It’s a huge part of where I see opportunity in the retail sector and beyond,” explained Kulkarni. 

“Really what changed at the end of 2022 when ChatGPT came out is that it was the era of large language models which has now really taken the world by storm because it can essentially read, it can write, it can analyze, it can generate new thoughts, new words, new images, new videos. It’s a completely new era of technology.

“We have been experimenting with AI and we’ve started to inject AI into a lot of trend technology. So one simple example of that is that we watch social media at scale. On any given day, using AI, we are watching 50,000 social media videos a day. And of course that’s more than any human can watch and we’re training that AI to watch it and to understand it and to categorize videos, help us identify new trends, help us identify how new trends are evolving. This is the type of thing that two or three years ago would have been impossible.

“We’re also using AI to develop product ideas, to generate new products, new designs, whether it’s logos, whether it’s art. AI is very, very helpful on that front as well. Of course, AI isn’t perfect and it makes all kinds of mistakes and so it’s something that needs to be developed and trained but we do see it as the future and it really is a way that retailers can get an edge over the competition by being able to adopt these new technologies and deploy them very quickly whether it’s in product development, whether it’s marketing or whether it’s in data analysis. We see a big potential there.”

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