Ep. 133 | Scotty Wittrup on Alt Lending, Growth & Reputation

Ep.137 | $400M AUM, Zero Principal Lost w/ Yitz Levinson

Neal and Ryan sit down with Yitz Levinson, President of Hillmount Capital,  a Toronto-based private lender with over $400M under administration and 22 years in the business. Yitz shares how his background as a licensed insolvency trustee shaped the way Hillmount underwrites every deal: exit first, entry second. The conversation covers their unique MFT structure, how they flex across residential, commercial, and construction depending on market conditions, their approach to special situations and insolvency lending, and why Yitz is more focused on deal terms than competing on rate in today's aggressive market. If you want to understand how a sophisticated, long-running private lender thinks about capital preservation, risk, and the current economic climate, this is a must-listen. Show Notes: 1:45 - From Accountant to Insolvency Trustee 3:23 - How Hillmount Was Founded 4:27 - The #1 Reason Deals Go Bad 5:56 - Hillmount's Lending Profile 7:21 - Construction Loans 8:12 - What Differentiates Hillmount 9:20 - Special Situation Lending 11:07 - Speed, Direct Lending & the HiLOC 12:30 - White Glove Service 14:54 - MFT vs. MIC 16:11 - Organic Investor Growth 17:59 - Staying Disciplined on Rate & LTV 18:15 - Preservation of Capital 19:09 - Concerns About Today's Market 21:49 - Tariffs, Recession & the Macro Picture 22:23 - Warning Signs on the Street 23:21 - Short-Term vs. Long-Term Loans 24:13 - Are We in a Recession? 25:33 - No Land Buying = Future Housing Shortage 26:06 - Regional Market Breakdown 28:06 - Bruised Credit Borrowers 28:45 - Working With Borrowers in Distress 30:14 - Mortgages Act Reform 31:45 - Concerns About New Products in the Market 32:46 - "We Underwrite the Story, Not the Box" 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: ryan@keycap.ca

Ep.136 | How Leadout Capital Fills the Gap Between Banks and Private Funds

Ryan and Neal sit down with Brian Suta, Partner at Leadout Capital, live at the CAMLA Ontario Expo. Brian breaks down how Leadout operates as a corporate debt fund,  lending to mortgage funds, MICs, and businesses that fall through the cracks of Canada's big banks. From borrowing base structures to a Winnipeg protein powder brand, it's a look at a corner of private lending most people don't know exists. Show Notes: 0:00 - Intro live from CAMLA Ontario Expo  2:11 - Brian's background: CPA, Street Capital, RFA  4:19 - How Leadout Capital was born  5:23 - What Leadout does and who they lend to  7:02 - Portfolio breakdown: mortgages vs. corporate debt  8:07 - The gap in Canada's banking system Leadout fills  9:33 - How they structure loans to mortgage lenders  13:44 - Case study: Kaizen Nutrition in Winnipeg  17:11 - Pricing, underwriting, and security  18:59 - Fund structure: GP/LP and tax treatment  24:08 - Case study: Alberta fix-and-flip lender  26:49 - Market outlook and rate forecast  29:12 - Hamilton Marathon sponsorship + bonus: Brian's 2:51 Paris Marathon 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: ryan@keycap.ca

Ep.135 | The Riskiest Loan in Private Lending

Construction loans can be incredibly rewarding, but when they go sideways, they can turn your lending business into a project management nightmare. In this episode, Neal and Ryan break down why incomplete construction loans are the riskiest deals in private lending, sharing a real story from their own portfolio where two simultaneous builds went off the rails. They cover the critical decision every lender faces in default: sell as-is or complete the build, the red flags to watch for, and the internal tools and processes that have saved them from bigger losses. Show Notes 0:07 - Cold open & intro 5:15 - Amazon building a 1M sq ft warehouse in Halifax 8:50 - What's the riskiest loan in private lending? 10:02 - Real story: Keystone's two construction loans that went wrong 13:37 - How secondary security saved them 16:30 - Sell as-is vs. complete the build 17:56 - Decision framework by completion percentage 24:13 - Red flag: when your borrower goes silent 26:02 - Ryan's biggest blow-up: fire + lapsed insurance on a 12-unit build 28:33 - Active management & draw tracking 37:10 - Key takeaways & best risk mitigation tools 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: ryan@keycap.ca

Ep.134 | How Private Lenders Should Handle Excess Capital

What happens when investor capital is flowing in, but strong deals aren't? In this episode, Neal and Ryan tackle one of the most underrated problems in private lending: having too much dry powder. They break down the dangers of forcing bad deals, the smartest ways to deploy (or hold) idle capital, and the levers you can pull on both the capital and deal-flow side of the business. Whether you're running a fund or operating as an individual lender, this one is packed with practical, hard-won insight. Show Notes: 03:20 Setting the stage: when capital inflows outpace deal flow 08:00 How excess capital leads to blown portfolios, the slow erosion of underwriting standards 12:17 Option 1: Pay down leverage first (lines of credit, co-lenders) 16:02 Option 2: Early investor redemptions, start with those already hinting at an exit 21:22 Option 3: If you must redeem, prioritize newer investors over long-term sticky capital 21:59 Option 4: Sit on the cash, painful, but better than losing it 23:08 Generating more deal flow: broker relationships, targeted outreach, and niche clarity 27:02 Liquidity forecasting: why most capital problems are really forecasting problems 32:19 Key takeaways and close 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: ryan@keycap.ca

Ep. 133 | Scotty Wittrup on Alt Lending, Growth & Reputation

In Episode 133, Ryan and Neal sit down with Scotty Wittrup, newly appointed VP of Network Development at DLCG, for a conversation that goes far beyond mortgages. From his early days in sales and brokering, to building a reputation across Canada’s mortgage industry, Scotty shares the lessons he’s learned about leadership, recruiting, credibility, and what truly makes a successful broker in today’s market. The episode dives into the evolution of alternative lending, the changing GTA real estate landscape, the realities of growing a national brokerage network, and why relationships still matter more than ever in this business. Plus: stories from Scotty’s East Coast roots, junior hockey days, nightlife adventures in Toronto, and his thoughts on where the mortgage industry is headed next. SHOW NOTES: 00:00 – Intro + post-interview recap with Ryan & Neal 01:17 – Neal’s ankle injury story and opening banter 03:21 – Scotty Wittrup joins the show 03:55 – How Scotty got into the mortgage industry 05:49 – His years with Mortgage Intelligence & INVIS 06:07 – Joining DLCG as VP of Network Development 09:16 – Why he made the move to DLCG 11:04 – Recruiting brokers and identifying the right fit 13:05 – What separates successful brokers from the rest 17:13 – Understanding the DLCG / MCC / Mortgage Architects structure 18:34 – The “ego” behind starting mortgage brokerages 22:33 – Growing broker networks in Atlantic Canada 25:30 – How Scotty evaluates where brokers fit within a brand 28:03 – Why brokers are approaching larger networks today 30:09 – GTA condo market struggles and pre-construction losses 36:32 – Why every broker needs alternative lending solutions 38:58 – Building long-term client loyalty through alt lending 42:34 – The hardest part of building a mortgage career 45:18 – The importance of presence, networking, and industry events 48:34 – Scotty’s Dalhousie days and East Coast roots 50:59 – Junior hockey stories and life in Halifax 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: ryan@keycap.ca Scott Wittrup 416-971-5534 Scott.wittrup@mtgarc.ca "Choose a brand that fits you, What to look for when joining a brokerage"