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Top 10 Questions To Ask Your Pineapple Mortgage Broker When Renewing Your Mortgage

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Pineapple Wins the Award For Digital Innovation in the Canadian Mortgage Industry

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In The Media

Pineapple is a leader in the Canadian mortgage industry, breaking the mould by focusing on both the long-term success of agents and brokerages, as well as the overall experience of homeowners. For media inquiries, please get in touch.


Pineapple Financial

FinTech TV

Interview with Pineapple CEO, Shubha Dasgupta

By Remy Blaire

Pineapple’s CEO, Shubha Dasgupta, was interviewed by Remy Blaire from FinTech TV on the trading floor at the New York Stock Exchange.

Cheddar News

Using A.I. to Improve Homebuying - Interview with Pineapple CEO, Shubha Dasgupta

By Kristen Scholer

Pineapple’s CEO, Shubha Dasgupta, was recently featured on Cheddar Business, discussing the ground-breaking new AI technology, Maui.

Manitoba Inc.

Pineapple Expands Into Western Canada

By Manitoba Inc. Staff

Toronto-based Pineapple Financial Inc. announced on Dec. 1 that it has established a new office in Western Canada to complement its expansion into Manitoba, Saskatchewan, Alberta and British Columbia.

The tech-enabled mortgage brokerage will have a new office in Coquitlam, B.C., serving as a central hub for the company’s operations in Western Canada.

Pineapple has 50 new mortgage professionals in three of the four western provinces, including the Jan Reyes Team and the Marilyn Magtoto team, both based in Winnipeg.

CMP Magazine

Over $2.5 trillion of opportunity ahead in Canada's purchase market: CEO

By Fergal McAlinden

Shubha Dasgupta (pictured) calls it the $2.56 trillion opportunity: the potential amount of purchase activity that could be unlocked in Canada’s housing market in the coming years as younger Canadians come of homebuying age and immigration continues at a rapid clip.

Speaking at his company’s flagship Xchange event in Markham last week, the Pineapple Financial co-founder and CEO told an audience of mortgage professionals that those factors were set to spur resurgent housing and mortgage markets in the years ahead, despite the downturn that’s taken hold in recent times.

CMP Magazine

Pineapple IPO a testament to the strength of mortgage brokering, says CEO

By Fergal McAlinden

Pineapple Financial president and CEO Shubha Dasgupta (pictured) has described the company’s landmark listing on the New York Stock Exchange (NYSE) as the proud culmination of a “lengthy journey” for the company after its stock went public last week.

Speaking yesterday at Pineapple’s flagship Xchange event at the Crystal Fountain in Markham, Ontario, which he said drew over 600 attendees, Dasgupta told Canadian Mortgage Professional the achievement was a reflection of his team’s shared focus toward hitting that milestone target.

Trusted Mortgage Capital

Canadian mortgage broker lists on U.S. exchange


Toronto-based mortgage broker Pineapple Financial is listing on the NYSE American exchange, because its management sees growth potential, not just in its home country, but across borders, including the United States, as well.

“We took all that into consideration,” said its CEO Shubha Dasgupta. “We looked at what would be the optimal exchange that would provide us with the requirements that we needed, as well as the visibility and the NYSE [American] checked all the boxes on that.”

The company priced the IPO at U.S.$4 per share. But once trading commenced on Nov. 1, the shares started falling — a factor with several of the U.S. mortgage company offerings as well — to a low of $2.67 per share before regaining ground to $3.30 per share by noon.

That growth potential is through its technology. Pineapple’s roadmap calls for others to utilize and deploy its software and platforms, Dasgupta said, although things could change given the fluid nature of the mortgage business.

Besides the expansion of its business, the aggregate gross proceeds of U.S. $ 3.5 million are to be used for improving technology; developing Pineapple Insurance; and giving Pineapple working capital and other general corporate purposes.

CMP Magazine

Pineapple CEO on housing market prospects for the rest of 2023

By Ephraim Vecina

Canadian households have seen their budgets significantly curtailed by sharply rising borrowing costs over the past year.

The impact of elevated interest rates is likely to last much longer than many would expect, warned Shubha Dasgupta of Pineapple.

For the rest of 2023, “we’re probably going to see activity at a level [where] it is today, at the base level,” Dasgupta said in a recent interview with Canadian Mortgage Professional.

CMP Magazine

Pineapple CEO on the importance of R&R in 2023

By Ephraim Vecina

Tech-focused brokerage highlights its guiding philosophy for this year.

With tech-focused brokerage Pineapple having established itself as a formidable industry presence over the past few years, president and CEO Shubha Dasgupta said that the company will be focusing on buttressing the fundamentals.

“Each year at Pineapple, we like to take a philosophy of following a theme – and this year, our theme has been ‘R&R’,” Dasgupta said in a recent interview with Canadian Mortgage Professional.

However, Dasgupta stressed that Pineapple’s R&R is nowhere near being a lackadaisical phase of rest and relaxation.

CMP Magazine

The Most Influential Women in the Canadian Mortgage Industry | Top 50 Women of Influence 2023

August 2023

Canadian Mortgage Professional’s Top 50 Women of Influence for 2023 have had an extraordinary impact on the industry, significantly shaping the future of a dynamic market and lighting the path ahead for others. Selecting this year’s cohort proved daunting for the esteemed judging panel, which remarked that there was no shortage of accomplished women driving change and progress.

Pineapple's Chief Strategy Officer, Christa Mitchell made the list this year as did Petra Keller, Director of Sponsorships and Events.

The Canadian Mortgage Broker Magazine - (CMBA National)

Pineapple’s Shubha Dasgupta shares insight into his mortgage industry career and the values that drive his success

By Lisa Gordon
Summer 2023

Shubha Dasgupta has never been one to avoid a challenge. In fact, he believes that on the other side of adversity lives greatness.

It’s a viewpoint that has served him well, from his childhood in Scarborough, Ont., to the present day as the CEO and co-founder of mortgage brokerage Pineapple.

“I’m famous for saying that when you ask people at age six or seven what their dream job is, no one says mortgage broker,” laughs Dasgupta. “What brought me here to this industry was entrepreneurship. I’ve been focused on that since the age of 20 when I launched my first business.”

CMP Magazine

Pineapple CEO talks company growth, market outlook after expansion

By Fergal McAlinden

The brokerage has taken on a new CFO and widened its reach into Western Canada.

An eventful 2023 to date for Pineapple Financial has continued to gather pace in recent weeks, with the company announcing its expansion into Western Canada and unveiling a new chief financial officer.

The brokerage revealed an alliance with Canada Lending House in British Columbia at the end of May, a partnership that will see it offer mortgage services in the West, just days before naming Sarfraz Habib to the CFO position.

Pineapple president and CEO Shubha Dasgupta (pictured top) told Canadian Mortgage Professional that the news reflected a strong first half of the year for the company, marking its growth amid a turbulent but resilient mortgage market.

Global News Morning BC

Is the demise of Silicon Valley Bank the break Canadian home buyers have been waiting for?

By Craig Lord

What does the collapse of Silicon Valley Bank in the U.S. mean for Canadians? Global News Morning speaks with Pineapple CEO Shubha Dasgupta about the potential silver lining for Canadians looking to buy a home or renew their mortgage.

Global News

SVB Instability Could Drive Some Canadian Mortgage Rates Lower.

By Craig Lord

The fallout from the collapse of Silicon Valley Bank has spread to the Canadian mortgage market, with some forecasters now expecting the Bank of Canada to cut interest rates sooner than previously thought.

But some experts say that while the recent shakeup in financial markets could drive fixed-rate mortgage rates lower in the near term, whether the disruption is enough to shake the Bank of Canada off its rate path remains to be seen.

Global News

‘Airbnbust’? Why Canada’s short-term rental hosts are in for a harsh winter

By Craig Lord

When Tamara Saeed and her husband were looking for a way to save for their children’s education a few years ago, the allure of Airbnb caught their eye.

The family bought a cottage near Grand Bend, Ont., in late 2019, with plans to host the property on the short-term rental platform. They almost second-guessed the move when the COVID-19 pandemic struck, but the waves of Canadians looking to escape the city during lockdowns proved a boon for the new cottage owners.

CMP Magazine

The People-First Path To Success


Shubha Dasgupta has never lost sight of the importance of service throughout his distinguished career to date

Few, if any, six-year-olds initially aspire to be mortgage brokers – and Shubha Dasgupta was no different. As a child, he harboured ambitions to become a doctor as a means of helping people, but fate works in mysterious ways and Dasgupta ultimately pursued another form of service: as a mortgage professional, assisting Canadians across the country in their efforts to realize their homebuying dreams.

Toronto Star

How To Navigate A Real Estate Market In Flux


The pandemic poured fuel on an already red-hot housing market in Canada and sent house prices soaring. But with interest rates rising, home prices are now showing signs of stabilizing or even dropping. And that’s generating uncertainty for prospective homebuyers.

We asked Shubha Dasgupta, CEO and founder of digital mortgage company Pineapple, to answer some of your burning questions about how to get into the home of your dreams.

CMP Magazine

Housing Market Slowdown: How Have Things Changed For Buyers?

By Fergal McAlinden

The housing and mortgage markets may have cooled off substantially in recent weeks – but that’s bringing opportunities for buyers including greater choice and less competition from rival bidders, according to a prominent industry figure.

Shubha Dasgupta, CEO of the Pineapple broker network, told Canadian Mortgage Professional that the recent slowdown, which has seen home sales activity drop off across many markets, has removed some of the intensity from the purchasing process and provided some welcome respite for buyers and brokers alike – not least because supply is becoming available at last.

CMP Magazine

Canada Housing Crash – Mortgage Professionals On How Likely It Is

By Fergal McAlinden

As interest rates continue to rise and home sales experience a marked cooldown from the barnstorming activity of the past two years, there’s been much furore of late over the prospect of a housing market crash in Canada.

Still, members of the country’s mortgage industry don’t appear convinced the bottom is about to fall out of Canada’s housing and mortgage markets. Rather, many have emphasized to Canadian Mortgage Professional in recent weeks that home buying activity across the country is experiencing an inevitable drop toward more normal levels, having witnessed an unprecedented spike throughout the low-rate environment of the early pandemic.

CMP Magazine

Ontario Election: Brokers Have Their Say

By Fergal McAlinden

Ontario voters head to the polls on Thursday (June 02) to decide who will lead the province’s 43rd parliament – and it’s no surprise that housing issues have been placed front and centre as an election issue throughout the campaign.

Few parts of Canada have seen a housing affordability crisis as pronounced as Ontario, with prices shooting far beyond the reach of many would-be buyers. That’s been especially apparent in the Greater Toronto Area (GTA), the province’s most populous urban sprawl, where two metropolitan areas – Toronto and Hamilton – feature in the top 10 least affordable cities in North America, according to Oxford Economics.

Good To Hear Podcast

Pineapple Mortgage Raises Funds for MLSE

By Jim Lang

Christa Mitchell meets with Jim Lang to discuss how Pineapple Mortgage raised $15,000 to benefit youth sports and the MLSE Foundation.

The Morning Rush

The Morning Rush - Shubha Dasgupta Interview: "Gifted Down Payments And How Do They Work?"

By Bill Carroll

Shubha Dasgupta - President of the Canadian Mortgage Brokers Association and CEO of Pineapple, Canada’s digital mortgage solution “Gifted down payments and how do they work?” The Morning Rush with Bill Carroll every weekday from 5:00 am to 9:00 am on News Talk 580 CFRA.

CMP Magazine

CEO Offers Mortgage Market Updates

By Fergal McAlinden

As Canada’s spring market ramps up, Canadian Mortgage Professional sat down with Pineapple CEO Shubha Dasgupta to hear his thoughts on market activity this year and the role technology is likely to play in the industry in the coming years, as well as checking on the latest updates at CMBA-Ontario.

Toronto Star

What do rising interest rates mean for you?


Whether you have a mortgage or you’re in the market for a home right now, you’ve probably heard interest rates are rising. And you’re wondering how that may affect you.

The good news, says Shubha Dasgupta, founder and CEO of digital mortgage expert Pineapple, is that “The sky isn’t falling.” Rates are expected to rise only minimally, at least in the short term. But it’s wise to pay attention to the changes. Here’s what you need to know, depending on the type of mortgage you have, where you stand in your mortgage journey, or whether you’re simply in the market for a home:

CMP Magazine

Manoeuvring The Reins Of A Mortgage Space Disruptor

By Ephraim Vecina

Scaling a valuable tech innovator at an accelerated pace presents a significant challenge.

As part of the pioneering Capital Lending Centre, later rebranded into Pineapple, co-founder and chief executive officer Shubha Dasgupta (pictured) believes that the mere presence of a tech disruptor brings with it a unique set of challenges.

“The most challenging has been scaling Pineapple at a very rapid pace,” Dasgupta told Canadian Mortgage Professional.

This stemmed from “ensuring that our infrastructure and resources were able to handle the growth and that we did not allow that growth to impact our service levels,” Dasgupta added. “We always ask ourselves about purpose and intent and having a clear insight into these areas for all aspects of our business. When you understand the goal, you can work back to create the roadmap.”

Toronto Star

The Right Mortgage Broker Can Smooth Your Path To Homeownership


Pineapple CEO Shubha Dasgupta explains how to choose the right mortgage broker, and why it matters.

You’ve found the home of your dreams. But that’s just the beginning. Your choice of a mortgage product is almost as important as your property, according to Shubha Dasgupta, CEO and founder of the digital mortgage company, Pineapple. The right mortgage broker can guide you through the entire process, saving you time and reducing stress, and can help you pick the product and provider that are best for your circumstances.

Where to find the right broker

Digital mortgage platforms with brokers at the helm, such as Pineapple, are changing the game when it comes to finding a mortgage. “We have over 450 highly experienced and well-trained mortgage agents in our Canada-wide network, available through our tech platform,” said Dasgupta. “They all go through a rigorous interview process as well as validation and background checks before they can be listed. We provide more than 45 hours of live training every month, as well as a fully digital platform to ensure they deliver best-in-class and proactive service.”

Toronto Life

Pineapple Financial Is Empowering Homebuyers Across The Country


While modernizing mortgages is no easy feat, this new consumer-facing brokerage holds the keys to success—and your new home.

In the same way that technology has changed how we shop for clothes, catch up on news and communicate on a daily basis—the way we manage our financial lives has evolved as well. And for homebuyers, the experience of accessing a mortgage is no exception to this much-needed evolution. More than 400 mortgage brokers and agents, AI-driven systems and cloud-based tools make up Pineapple Financial, a digital-first brokerage reimaging the home buying experience.

The company’s forward-thinking approach has established itself as a destination for all types of homebuyers seeking secure and trustworthy expertise to enhance their purchasing power. Dedicated to providing mortgage-seeking Canadians with the best service on the market, Pineapple’s smart software makes communication easy, while a flexible range of products make every client experience custom fit. Thinking about the possibility of homeownership for yourself? Meet some of Pineapple’s clients who’ve made the most of their means with the brand transforming the way Canadians access mortgages. 

Toronto Life

The Pineapple Financial Success Stories You Ought To Know


The innovative brokerage is on a mission to guide all of Canada into a new age of mortgages.

Accelerated by the pandemic, tech integration has shifted nearly every industry into the future, and the financial sector is no exception. Pineapple Financial has secured its role in kick-starting that shift with an integrated network of more than 400 mortgage brokers and agents, AI-driven systems and cloud-based tools to make the home buying experience seamless and transparent. The digital-first brokerage believes the road to homeownership, a major milestone in your financial journey, ought to be a process inspired by the brand’s namesake—a symbol of warmth and hospitality. 

Whether you need a clear assessment of your buying power or find yourself in a time-crunch to secure a mortgage, Pineapple takes on the heavy lifting to save you time and money, acting as an expert advisor throughout your entire mortgage process. Start with an online application, explore the intelligent MyPineapple platform and gain full insight into deals and optimal offers based on their needs. Many Canadians have successfully secured their dream homes by working with a Pineapple broker. If you’ve begun to think about homeownership or are actively searching for a property, let their stories inspire you.

Toronto Star

Why Working With A Mortgage Broker Can Save Time And Money


Say ‘home sweet home’ with Pineapple’s personalized mortgage brokerage model.

It’s no secret that Canada’s housing market is having a moment. With housing prices on a continual rise, especially in urban areas, plus new and ever-changing mortgage rules, it’s a challenging market to navigate, especially for those looking to buy their first home. Many first-time buyers looking to get a mortgage – or those looking to renew, refinance or tap into their home equity – go straight to the bank. But what if going through a mortgage broker could save you time, and even money?

Working with a mortgage broker can help homebuyers understand the market dynamics. With a strong focus on client service, a great broker will help you secure not just the best mortgage rate, but one that is the best fit for your specific financial situation.

This, at least, is the goal of Pineapple, a Toronto-based mortgage brokerage that is setting itself apart from traditional mortgage brokerages in Canada. With a growing network of more than 400 highly trained agents and brokers and with cutting-edge technology embedded into their processes, they have extensive knowledge of the Canadian housing industry, a focus on exceptional service and a diverse range of mortgage products at their fingertips.

CMP Magazine

What Does This Innovative Exec Depend On?

By Ephraim Vecina

It's a lesson that every mortgage professional could take to heart.

As co-founder and chief executive officer of mortgage industry innovator Pineapple, Shubha Dasgupta (pictured) leans on a fundamental lesson that every mortgage professional should take to heart.

“Look at the first few years of your career as a paid internship,” he said. “Don’t be afraid to try things; succeed and fail, but be patient with yourself. There is no such thing as overnight success, and everything comes to those who wait. Remember that patience is not about waiting but the attitude and work you put in while waiting.”

The mindset of patience and perseverance came naturally to Dasgupta, despite the mortgage space not being his first choice of vocation.



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