
BEHIND THE LENDER – Ep. 53 with Jesse Bobroski, Calvert Home Mortgage
Hosts: Dean Lawton & Deryk Williamson
In this episode of The Mortgage Broker Podcast, Dean and Deryk continue the Behind the Lender series with Jesse Bobroski, Vice President of Calvert Home Mortgage. Recorded on-site at Calvert’s Calgary headquarters, this conversation dives deep into how one of Canada’s most established private lenders—now celebrating 50 years in business—continues to evolve, innovate, and serve brokers across the country.
From Bartender to Private Lending Leader
Jesse shares his unconventional path into the mortgage world. After completing a finance degree in Ontario, he moved to Calgary during the financial crisis and stumbled into alternative lending while bartending. A chance meeting with a couple who ran a syndicated mortgage firm opened the door to a career in private capital—a world Jesse found refreshingly transparent and relationship-driven.
Nearly two decades later, he’s built a career defined by mentorship, curiosity, and an unwavering focus on helping borrowers who fall outside the banks’ comfort zones. Today, at Calvert, he helps manage a diversified Mortgage Investment Corporation (MIC) that funds short-term mortgages for both real estate investors and clients who simply don’t fit the traditional mold.
Inside Calvert Home Mortgage
Founded in 1981 as a MIC by Everett Keller, Calvert has grown from a family-run brokerage into a nationally respected private lender. Now led by Everett’s sons, Dean and Dale Keller, the firm has expanded from $35 million in annual fundings to over $550 million—supporting more than 1,400 transactions a year.
Calvert’s approach is rooted in service, education, and innovation. A key differentiator? In-house valuations. Instead of relying on third-party appraisers, Calvert employs its own appraisal team to assess properties and manage risk. This allows for same-day funding, faster decisions, and greater confidence for both brokers and investors.
Valuations, Risk, and the “After-Repair” Mindset
Jesse explains how Calvert’s internal valuation system is central to both client speed and investor security. Every deal is stress-tested and backtested to ensure accuracy. When discrepancies arise, Calvert takes a collaborative approach—welcoming appeals and feedback from brokers and local experts.
Their After-Repair Value (ARV) model also sets them apart. Especially for flippers and real estate investors, Calvert acts as both lender and consultant, evaluating renovation budgets, utility costs, and even carrying expenses. Borrowers can secure financing with as little as $10,000 down, enabling more opportunities for investors and tradespeople to participate in the market.
Multifamily Momentum and Market Trends
The conversation turns to multifamily lending, where Calvert is gaining traction. Rather than ground-up construction, their focus is on underutilized small-scale multifamily properties—sixplexes, eightplexes, or similar—that can be repositioned and refinanced through CMHC’s MLI Select program.
Jesse also highlights major industry trends, including consolidation among private lenders, increased professionalism, and a more data-driven approach to risk. He notes that Alberta’s cyclical market has taught lenders resilience—an experience now helping them navigate corrections in BC and Ontario.
Behind the Scenes: Calvert’s Team & Workflow
Calvert’s workflow is designed for speed and precision. Underwriters are empowered to make exceptions, escalate intelligently, and communicate directly with brokers to find solutions. Every deal moves through a refined structure—from credit decision to legal instruction—largely managed in-house, including their legal team, to minimize cost and friction.
Their culture rewards underwriters who “find a way to make deals work,” reinforcing a make-sense approach that values relationships and creativity over rigid formulas.
The Broker Relationship
When asked about working with brokers, Jesse is clear: “We want to win with the winners.”
Calvert prioritizes partnerships with top-tier brokers who understand their products and share their mindset for speed, transparency, and trust. These relationships are strengthened by responsiveness—returning texts after hours, collaborating directly with borrowers, and delivering on tight timelines.
Renewals are handled ethically and proactively, with brokers always contacted before the borrower and no surprise fees. It’s all part of a long-term retention philosophy that protects both client and broker relationships.
Compliance, Technology, and the Future
Calvert approaches compliance as a strategic advantage, not a burden. As early supporters of the Canadian Alternative Mortgage Lenders Association (CAMLA), they’ve helped shape industry standards and policies. Jesse emphasizes a balanced approach: staying ahead of FinTrack and AML expectations while keeping processes “make-sense” and client-friendly.
On the tech front, Calvert is investing heavily in data centralization and AI-driven insights. Their long-term goal: a fully integrated platform that connects accounting, underwriting, business development, and broker portals—automating valuations, pricing, and performance analytics to improve service and scale intelligently.
Borrower Experience
For clients—especially real estate investors—Calvert strives to make borrowing “as effortless as possible.” Their team can manage everything from document collection to direct communication, always keeping the broker in the loop. Once a client is introduced by a broker, they remain that broker’s client for life.
This trust-based system has built a loyal network of repeat investors and brokers who rely on Calvert not only for financing but for mentorship, analytics, and market insight.
Final Thoughts
As Calvert celebrates 50 years, Jesse Bobroski and his team are proving that innovation and integrity can coexist in private lending. With their in-house valuations, commitment to education, and data-first strategy, Calvert is redefining what it means to be a modern MIC.
Their focus remains clear: faster decisions, stronger broker relationships, smarter technology—and a mission to help more Canadians build wealth through real estate.
Why You Should Listen
This episode offers a masterclass in how modern private lending really works—from underwriting culture and borrower psychology to valuation, tech, and risk. Whether you’re a new broker learning the ropes or an established pro seeking trusted partners, this behind-the-scenes look at Calvert Home Mortgage is packed with insight, strategy, and inspiration.
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