Canadian Private Lenders’ Podcast

Ryan and Neal sit down with Jason Alexander, CEO of Mortgage Automator and now also CEO of Lendr, for a candid conversation about the software powering a huge chunk of Canada's private lending industry. Jason unpacks his 30 year career in tech, from his very first job working for Mark Cuban in 1996, to leading multiple software companies through major growth and eventually landing in the CEO seat at Mortgage Automator just over a year ago.

The guys dig into the recent Lendr acquisition and why it fundamentally changes how Automator will operate going forward, with Automator becoming Canada exclusive and Lendr taking over as the platform for all US customers. Jason gets refreshingly transparent about what was working, what needed to change, and where the product is headed next. Expect deep dives on the upcoming loan servicing overhaul, why big lenders are asking Automator to help them get rid of their in house IT teams, how AI and MCP integrations will change day to day lending workflows, and Jason's take on the differences between the Canadian and American lending markets. If you use Automator, are considering it, or just want to understand where lending tech is heading, this one is essential listening.

Show Notes

• 00:00 Recap: hosts break down the biggest takeaways from the interview
• 01:31 Meet Jason Alexander, CEO of Mortgage Automator and Lendr
• 02:11 Starting his career working for Mark Cuban in 1996
• 05:20 How Jason went from retirement to running Mortgage Automator
• 06:40 Leaving college 32 hours short of a CS degree
• 08:56 What attracted Jason to Automator from his loan servicing background
• 11:02 Why big lenders want Automator to help them cut their IT teams
• 13:34 Rethinking what Automator's customer service team actually does
• 15:37 One year in: what Jason inherited and what he plans to change
• 17:35 Why the credit union segment needs a specialized product
• 19:10 The big reveal: Automator becomes Canada only, Lendr takes over the US
• 22:57 How the US customer migration to Lendr is being handled
• 23:59 The biggest differences between the Canadian and American lending markets
• 25:37 Why the Canadian mid market barely exists
• 26:07 Inside the Lendr acquisition: how the deal actually came together
• 30:04 The barbecue meeting in South Phoenix that sealed the partnership
• 32:09 How Bryce, the former Lendr CEO, is reshaping Automator's product philosophy
• 34:41 Are more acquisitions on the horizon?
• 36:06 Is AI a threat to companies like Automator?
• 39:11 What Automator customers can expect in the next 12 months and beyond
• 43:12 The MCP rollout and what it means for AI powered workflows
• 46:11 Bonus round: Jason's top food and travel picks in the US

Resources:
Keystone Capital Group
CPLP Instagram: @cplpodcast
Keystone Instagram: @keycapgroup

Find Neal On:
Instagram: @neal.andreino
LinkedIn: Neal Andreino

Find Ryan on:
LinkedIn: Ryan MacNeil
E-mail: [email protected]

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Ryan flies solo for Episode 152 and sits down with James Goode, a realtor with The Agency in Halifax and one of the most recognizable faces in Atlantic Canadian real estate content. If you have ever scrolled through TikTok or Instagram and watched a guy sprint through a stunning listing set to music, chances are you were watching James. In this conversation, he pulls back the curtain on how a random idea from a friend turned into a 200,000 view content formula, and how his social presence has actually closed deals for his clients.

James walks Ryan through his unlikely path into real estate, from a theology degree to becoming a CPA at Ernst and Young, before Covid pushed him toward a career reset. They dig into what makes content actually work in a saturated realtor market, why negativity in the comments is sometimes the best thing that can happen to a video, and the strategic differences between TikTok, Instagram, and YouTube. The two also cover the current state of the Halifax and rural Nova Scotia market, the price points that are moving versus sitting, and a preview of James's upcoming HGTV style TV appearance on Oceanfront Property. If you are a realtor, mortgage professional, or anyone building a personal brand, this one is loaded with tactical takeaways.

Show Notes:

• 00:00 Ryan's solo intro and setup for the interview
• 01:25 Meet James Goode of The Agency
• 01:55 From theology degree to CPA at Ernst and Young
• 04:04 How Covid pushed James out of accounting and into real estate
• 05:07 Why the accounting network was the biggest career catalyst
• 05:42 Hitting his stride five years into the business
• 07:25 The origin of the run through houses concept
• 08:52 Breaking down the time commitment behind viral content
• 10:12 How James is building a YouTube channel from scratch
• 11:35 The $6M Ontario listing that hit 200,000 views on TikTok
• 12:12 Why negative comments are actually great for the algorithm
• 15:06 Testing whether his social audience translates to new markets
• 16:20 Why real estate content is boring and how James breaks the mold
• 20:18 The strategy differences between Instagram, TikTok, and YouTube
• 22:20 Proof that viral content actually sells houses
• 23:20 The state of the Halifax and Nova Scotia market right now
• 26:11 The exact price points that are moving on the Peninsula and beyond
• 29:16 Whether James's clients are shifting toward mortgage brokers
• 30:54 A Keystone success story: saving the kitchenless house deal
• 31:17 James's advice to realtors: stop making boring content
• 34:15 James's upcoming appearance on the HGTV style show Oceanfront Property
• 37:33 Bonus round: favourite Halifax cafes and restaurants

Resources:
Keystone Capital Group
CPLP Instagram: @cplpodcast
Keystone Instagram: @keycapgroup

Find Neal On:
Instagram: @neal.andreino
LinkedIn: Neal Andreino

Find Ryan on:
LinkedIn: Ryan MacNeil
E-mail: [email protected]

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Neal and Ryan are back for a fun one, this time cracking open the strange, sometimes sketchy world of unique lending. Most people think lending means mortgages, car loans, and business lines of credit, but the reality is that almost any asset with real ownership, verifiable value, and a viable exit can be borrowed against. In this episode, the guys walk through the assets that actually get pledged as collateral every day, including stocks, cryptocurrency, fine art, watches, jewelry, wine, classic cars, receivables, inventory, patents, and even goodwill.

Along the way, Neal shares his skepticism on some of the market's more inflated corners, Ryan tells the wild true story of a $2 billion art thief who never sold a single piece, and the two get into the mechanics of how ultra wealthy collectors use their assets to unlock liquidity without triggering a tax bill. They wrap with a rapid fire round on what they would personally lend against, and the one form of collateral that keeps them both up at night.

Show Notes

• 00:00 Cold open and podcast intro
• 00:13 Neal's ongoing sleep struggle and watching his friends survive new parenthood
• 02:24 Setting up the topic: what makes something good collateral
• 04:34 Lending against stocks and investment portfolios
• 05:19 How banks offer 100% leverage on certain investment products
• 06:27 Would you rather lend on a diversified portfolio or a house?
• 08:02 Lending against cryptocurrency and the volatility problem
• 10:24 Fine art as collateral and the fraud risks behind valuations
• 12:58 Ryan tells the true story of The Art Thief and $2 billion in stolen art
• 15:07 Watches, jewelry, and gold: how influencers actually finance those Rolexes
• 17:14 A private lending story: taking a Rolex as second mortgage collateral
• 18:34 Fine wine as an investment grade asset class
• 20:15 Classic cars and the case for and against a $50 million Ferrari
• 24:03 Accounts receivable lending and invoice factoring
• 25:24 How commission factoring works in real estate
• 26:21 What makes good collateral: the five questions to ask every time
• 28:11 Rapid fire: what would you actually lend against?
• 32:22 Why goodwill and government down payment programs are quietly high risk
• 33:29 Closing thoughts

Resources:
Keystone Capital Group
CPLP Instagram: @cplpodcast
Keystone Instagram: @keycapgroup

Find Neal On:
Instagram: @neal.andreino
LinkedIn: Neal Andreino

Find Ryan on:
LinkedIn: Ryan MacNeil
E-mail: [email protected]

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Neal and Ryan hit a big milestone with Episode 150, and they're marking it with one of their most globally minded conversations yet. They kick things off with two massive Canadian deals that just crossed the wire: RBC and BMO offloading Moneris, one of the country's most important payment processors, to US private equity for $2 billion, and Air Canada selling a 25% stake in Aeroplan to Blackstone at a $10 billion valuation. The guys dig into what these deals actually mean for competition, consumer choice, and the quiet devaluation of your loyalty points.

From there, they zoom out to the main topic: private credit as a global asset class. Now worth over $2 trillion, private credit looks very different depending on where you are in the world. Neal and Ryan walk through how the US, Europe, Asia Pacific, Australia, and Canada each carved out their own version of it, why Canada's market is heavily tilted toward real estate, and where the sector may be headed next. They close with a sharp take on why Canada is unlikely to ever mirror the US model, and why that might actually be a good thing for disciplined lenders.

Show Notes

• 00:35 Episode 150 milestone and Neal's kiteboarding recap
• 02:15 Setting up the main topic: private credit as a global asset class
• 02:24 The Moneris sale and what it says about Canadian competition
• 04:03 Why the real problem is concentration, not the buyer
• 05:20 The Canadian monopoly problem: banking, telecom, and payments
• 06:08 Air Canada sells 25% of Aeroplan to Blackstone at a $10B valuation
• 08:07 Why loyalty programs are often worth more than the airlines themselves
• 09:00 How private equity ownership could accelerate points devaluation
• 10:05 The hidden business of loyalty: companies buying points in bulk
• 10:29 What is private credit? The categories that make up a $2T market
• 11:45 How the US came to dominate 65% of the global private credit market
• 13:56 Europe: infrastructure, renewables, and cross-border lending
• 17:15 Spotlight: United Wholesale Mortgage and the US private lending giants
• 17:35 Asia Pacific: Australia, Singapore, Hong Kong, Japan, and India
• 19:07 Canada's role: filling gaps rather than replacing banks
• 20:05 Why Canadian private credit is structured around real estate
• 21:31 Canada vs the US: mortgage-focused vs corporate-focused lending
• 22:08 Is Canadian lending really conservative? A different view on debt loads
• 24:08 Global trends: institutional capital, tech, higher rates, retail access
• 26:21 Where private credit is heading and Canada's real opportunity

Resources:
Keystone Capital Group
CPLP Instagram: @cplpodcast
Keystone Instagram: @keycapgroup

Find Neal On:
Instagram: @neal.andreino
LinkedIn: Neal Andreino

Find Ryan on:
LinkedIn: Ryan MacNeil
E-mail: [email protected]

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Neal and Ryan are back with a solo news roundup episode covering the biggest stories moving Canadian real estate, lending, and beyond. They kick things off with a wild data point out of Halifax: a brand new 291-unit downtown tower is sitting at just 20% leased, and what that could signal about vacancy risk creeping into REIT-owned portfolios across the country. Then they dig into new Mortgage Professionals Canada data showing broker share is climbing fast, hitting 38% overall and 48% among first-time buyers, with Quebec and Alberta leading the way and Atlantic Canada still lagging behind.

From there, the guys pivot into a very different conversation: Nvidia has struck deals with major investment firms to borrow against its chip inventory, and Neal shares his theory on why tech could become the next major asset class for lending (with a bonus Taiwan conspiracy thrown in). They wrap with a quick take on Mortgage Automator's acquisition of Lendr, why AI is starting to disrupt the legal tech stack, and a preview of who's coming on the pod next.

Show Chapters:

• 00:00 Cold open: broker share, tech lending, and Neal's electrolyte comeback
• 01:00 Catching up: biking, Portugal, kitesurfing in Brazil, and Costa Rica villa recs
• 04:12 The 291-unit Halifax tower that's only 20% leased
• 07:55 Overbuilt on multifamily, undersupplied on single family
• 09:58 Nova Scotia officially shifts into a balanced housing market
• 10:14 Why sellers are finally starting to concede on price
• 11:12 The ego problem in Canadian real estate
• 12:26 MPC data: broker share hits 38% overall, 48% with first-time buyers
• 13:29 Why younger buyers are ditching the bank branch experience
• 15:16 Continuity of service: why the broker relationship wins long term
• 16:32 Regional breakdown: Quebec, Alberta, Ontario, BC, and Atlantic Canada
• 19:22 How the UK compares and what it would take to close the gap
• 20:38 The education problem holding broker share back
• 22:13 Nvidia is now lending against chip inventory
• 23:32 Is tech becoming a viable asset class to lend on?
• 26:03 Neal's Taiwan conspiracy and the coming tech inflation cycle
• 28:28 Would you finance a phone on a 5 year loan?
• 29:51 The future of wearables, headsets, and brain implants
• 31:11 Mortgage Automator acquires Lendr in a major US play
• 31:43 Will firms start building their own AI tech stacks?
• 32:52 Preview: Jason Alexander of Automator coming on the pod

Resources:
Keystone Capital Group
CPLP Instagram: @cplpodcast
Keystone Instagram: @keycapgroup

Find Neal On:
Instagram: @neal.andreino
LinkedIn: Neal Andreino

Find Ryan on:
LinkedIn: Ryan MacNeil
E-mail: [email protected]

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In this episode, Neal and Ryan sit down with Arees Jiwani, President of TM Investments. Arees walks us through his journey from the Ivey Business School to helping build one of Canada's most rapidly growing financial services groups, going from seven employees to over 400 in a decade. We dig into RFA's acquisition of Street Capital, the launch of TM Investments in 2024, and the group's unique capital structure backed by long-term institutional investors and a wealth management arm based in the Cayman Islands.

Arees shares why permanent capital is the name of the game in today's private lending market, how TM Investments approaches AA and AAA deals in the competitive GTA space, and where he sees the biggest opportunity hiding in plain sight: the $3 to $4 million home segment in prominent Toronto neighbourhoods. We also cover bridge financing, blanket mortgages, creative deal structuring, and TM's ambitious plans to scale well beyond the $300M mark.

Show Notes

• 00:00 Hosts' recap: big goals, permanent capital, and competitive GTA pricing
• 01:30 Interview begins with Arees Jiwani
• 02:13 From the Ivey Business School to RFA: the origin story
• 04:00 RFA's growth story, from 7 employees to 400 in a decade
• 05:39 The three gaps in the private market TM Investments was built to fill
• 08:45 Breaking down the capital and infrastructure gaps in more detail
• 09:44 Inside the Cayman Islands wealth management operation (Five Continents)
• 12:06 The 20+ year investor relationships that anchor RFA
• 13:09 The RFA and Artis REIT merger and TSX listing
• 15:30 How TM Investments establishes truly permanent capital
• 18:31 Why the LP structure won out over the MIC
• 19:31 A walk through the RFA verticals
• 20:55 Ideal borrower profile: business-for-self and bridge financing
• 23:49 Underwriting the exit on bridge deals
• 24:53 The case for blanket mortgages in today's market
• 27:02 Beyond pricing: the step-up rate structure that wins deals
• 30:22 Average mortgage term and payout timing
• 32:05 The hidden opportunity in $3 to $4 million GTA homes
• 37:14 Scale on their terms: the 3 to 5 year vision
• 41:09 Opportunistic capital in a shrinking market
• 42:56 Acquisitions as part of the growth playbook
• 43:31 Bonus question: Flames or Leafs?
• 45:11 Restaurant recommendations in Toronto and Calgary

Resources:
Keystone Capital Group
CPLP Instagram: @cplpodcast
Keystone Instagram: @keycapgroup

Find Neal On:
Instagram: @neal.andreino
LinkedIn: Neal Andreino

Find Ryan on:
LinkedIn: Ryan MacNeil
E-mail: [email protected]

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Neal and Ryan step away from mortgages to tackle a topic Neal has been waiting three years to talk about: cars. In this episode, they pull back the curtain on how Canadian car dealerships actually make their money and spoiler, it's not from the sticker price. From lender commissions and rate markups to negative equity, money factors, and 8-year amortizations, the guys break down every trick, tactic, and hidden margin baked into the modern auto financing process.

They also compare Canada's auto lending environment to the U.S., U.K., and Australia (where regulators have already cracked down on dealer commission structures), talk about subprime auto lending, and dig into why the industry might be heading toward its own reckoning. Neal wraps things up with a bonus breakdown of the open-end lease structure he personally uses to finance his own vehicles, plus practical tips for using AI tools like ChatGPT to negotiate your next deal.

Whether you're buying, leasing, or just trying not to get taken for a ride, this one's packed with insight and a healthy dose of frustration from a genuine car lover.

Show Notes:

• 00:00 - Intro: Neal finally gets to talk cars
• 01:31 - Where dealers really make their money (hint: it's not the car)
• 02:47 - Why financing is always left to the end of the conversation
• 04:21 - The big question: is the dealer finding you the best loan, or the most profitable one?
• 04:53 - What is a "money factor" and why isn't it a legal APR?
• 06:04 - How Canadian dealer financing actually works (banks, credit unions, captive lenders)
• 07:31 - The subprime auto lending world and why it's different from private mortgages
• 08:48 - Lender commissions, rate markups, and how dealers stack margin
• 10:04 -The bait-and-switch: approved at 4.99, sold at 6.99
• 12:11 - Warranties, GAP, tire and rim protection and who actually claims them
• 13:08 - 0% financing decoded: the price is baked in
• 14:24 - Negative equity, 8-year loans, and the coming auto lending Netflix special
• 17:11 - How Canada compares to the U.S., U.K., and Australia
• 19:36 - Consumer protection in Canada and the cooling-off period question
• 22:48 - The must-ask questions before signing any auto loan
• 23:22 - The rise of vehicle brokers who negotiate on your behalf
• 24:20 - Bonus: Neal breaks down the open-end lease strategy he uses on his own cars
• 27:20 - Key takeaways for your next vehicle purchase
• 28:01 - Using ChatGPT as your negotiation copilot
• 28:57 - Final thought: the number that actually matters

Resources:
Keystone Capital Group
CPLP Instagram: @cplpodcast
Keystone Instagram: @keycapgroup

Find Neal On:
Instagram: @neal.andreino
LinkedIn: Neal Andreino

Find Ryan on:
LinkedIn: Ryan MacNeil
E-mail: [email protected]

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Greg Sinclair did not take a straight line into private lending. He went from teaching school in Ontario and the UK, to selling beer on the night shift at a local brewery, to building out the sales and marketing function for the Peterborough Petes in the OHL, to joining Magenta Capital when Covid shut down the sports world. He is now COO of one of the longest-standing MICs in Canada, a company founded out of a basement in 1994 that now manages $470 million in residential mortgages across Ontario.

Ryan and Neal sit down with Greg to talk through what has kept Magenta disciplined for 32 years, why they built a $470 million book with zero commercial, zero construction, and never leaving Ontario, and what drove the decision to finally enter the GTA a year and a half ago. They also get into Greg's read on where the Canadian real estate market sits right now, why condos are likely still a couple of years from recovery, what AI actually looks like inside a private lender's operations, and why tightening bank regulation keeps sending better and better borrowers into the alt space.

Plus career advice for anyone trying to break into the mortgage world, and some honest Leafs talk to close it out.

Show Chapters:

2:07 Meet Greg Sinclair, COO at Magenta Capital 

2:47 From Teacher to Brewery to OHL Analytics 

7:21 Landing the Peterborough Petes Job 

10:25 How Covid Led Greg to Magenta Capital 

11:09 32 Years and $470M: How Magenta Got Here 

13:36 The Decision to Enter the GTA 

16:57 $470M AUM on 1,000 Residential Loans 

17:19 Magenta's Products and Lending Parameters 

22:38 Looking Three Years Ahead: What Magenta Is Building 

24:29 Market Outlook: Near the Bottom or In It? 

26:20 Atlantic vs Ontario: Two Very Different Stories 

30:39 AI as an Accelerant, Not a Replacement 

33:40 Why Alt Lenders Keep Taking Market Share 

36:16 The Biggest Risk for MICs Right Now 

38:44 Career Advice for Mortgage Professionals

Resources:
Keystone Capital Group
CPLP Instagram: @cplpodcast
Keystone Instagram: @keycapgroup

Find Neal On:
Instagram: @neal.andreino
LinkedIn: Neal Andreino

Find Ryan on:
LinkedIn: Ryan MacNeil
E-mail: [email protected]

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Part two of the MIC series shifts from structure to strategy. Ryan and Neal make the case for why mortgage investment corporations have become one of the most compelling income investments for Canadians who have already won the real estate game and are looking for somewhere to put the proceeds.

They break down where MICs sit in the investment spectrum (between government bonds and equities), who is actually investing in them (it skews heavily toward boomers and recently exited real estate investors), and why the 9.2% average returns in 2024 and 7.7% in 2025 are pulling in institutional capital alongside individual investors.

They also go deep on the risks most people overthink: redemption gates, borrower default rates (around 2-3% in alternative lending), and what actually causes a MIC to blow up. Not every failure means investors lose money. Defaults are not the same as losses, and a fund that gates redemptions may be doing exactly what it should be doing.

Neal runs through the questions every investor should ask before putting money into a MIC: average loan to value, property types, first versus second mortgages, portfolio diversification, how loans are sourced, historical default experience, and how experienced the management team actually is. Plus one red flag worth knowing: a MIC chasing rapid growth is almost certainly lowering its underwriting standards to get there.

Show Chapters:

2:00 Today: The Investment Side of MICs

2:38 Where MICs Fit in the Investment Spectrum

5:11 The Compounding Math Nobody Talks About

6:32 GICs, Bonds, and Equities vs a MIC

10:02 Why Investors Love Monthly Income

13:09 Volatility Is Driving Investors Out of Equities

13:42 Who Actually Invests in MICs

14:19 9.2% Returns in 2024, 7.7% in 2025

15:36 Understanding the Real Risks

18:39 Redemption Gates Aren't a Red Flag

19:23 When MICs Have Failed or Struggled

21:20 Not All MICs Are Equal: What to Evaluate

24:57 Defaults Are Not the Same as Losses

28:16 Is a MIC Right for You?

30:00 Red Flag: Beware of Rapid Growth

Resources:
Keystone Capital Group
CPLP Instagram: @cplpodcast
Keystone Instagram: @keycapgroup

Find Neal On:
Instagram: @neal.andreino
LinkedIn: Neal Andreino

Find Ryan on:
LinkedIn: Ryan MacNeil
E-mail: [email protected]

Most Canadians think mortgages only come from the big six banks. They're wrong, and it's costing them. In part one of a two-part series, Ryan and Neal break down what a Mortgage Investment Corporation actually is, how it works, and why it exists in the first place.

They cover the borrowers banks turn away, how non-bank lenders get their capital, and why Canadian MICs are nothing like the Big Short. They dig into the numbers from Wawa's research: the top 43 mortgage investment entities manage nearly $38.5 billion in assets, delivered 9.2% weighted average returns in 2024, and yet still represent only 4% of Canada's total mortgage market. Compare that to the UK, where non-traditional lenders now account for 60% of gross mortgage lending.

They also break down what causes a MIC to blow up, why the biggest players are built to survive a downturn, and the uncomfortable truth about what your bank is actually doing with your savings account.

Show Chapters:

4:56 Today: What Is a MIC (Part 1 of 2)

6:09 Why Canadians Only Think of the Big 6

7:14 The Borrowers Banks Turn Away

10:44 Why Canadian MICs Aren't the Big Short

11:00 What a MIC Actually Is

13:30 What Causes a MIC to Blow Up

15:36 MIC vs Broker vs Bank

16:12 Who Actually Borrows From a MIC

18:39 $38.5 Billion Managed by the Top 43

19:22 MIC Returns: 9.2% in 2024

20:45 MICs Are Only 4% of the Mortgage Market

21:41 The UK Has 60% Non-Traditional Lending

23:32 Banks Give You 2% While Lending Your Money at 9%

25:47 Why Big MICs Will Survive the Downturn

29:39 How a MIC Expands Through Acquisition

Resources:
Keystone Capital Group
CPLP Instagram: @cplpodcast
Keystone Instagram: @keycapgroup

Find Neal On:
Instagram: @neal.andreino
LinkedIn: Neal Andreino

Find Ryan on:
LinkedIn: Ryan MacNeil
E-mail: [email protected]