In this episode of MikeDrop, we welcome Chris Vinson, CEO of Windsor Mortgage and head of the mortgage division at Plains Commerce Bank, for an unfiltered conversation about what it really takes to build trust in lending—beyond rates, margins, and spreadsheets.
Chris is a visionary leader who has built a legacy in wholesale and community banking by focusing not just on volume, but on relationships, coaching, and solving real problems for originators. Under his leadership, Windsor Mortgage originates over $5.6 billion annually, commanding over 25% market share in Sioux Falls, all while remaining deeply committed to education, innovation, and partnership. 
As both an executive and a mentor, Chris leads coaching programs like Coaching with Chris, through which he works with CEOs and loan officers nationwide to refine performance, scale with consistency, and weather changing market dynamics.

What You’ll Hear in This Episode


Chris’s journey from mortgage broker to building a national wholesale platform aligned with community banking


How Windsor differentiates itself against giants (like Rocket, UWM) through intensive coach support, originator-first strategies, and partner relationships 


Why trust is currency in lending—and how Chris believes lenders earn that trust through problem-solving, transparency, and backing brokers with tools, not demands


Tactical innovations in tech, process, and underwriting that reduce friction and make lending more human, not less


How Windsor’s warehouse lending, executive banking suite, and differentiated coaching give originators a competitive edge


The power of asking — for help, for clarity, for opportunity — and how that mindset shaped many of Chris’s biggest wins


Chris’s approach shows that lending isn’t just about what you offer—it’s how you partner, how you support, and how you help people believe again. Whether you’re an originator, loan officer, or bank leader, this episode will challenge how you measure success in mortgage.

Sponsors & What They Do


Mortgage Connect — A full-lifecycle mortgage services provider, handling closing, title, valuation, and risk mitigation to make lending smoother. Visit: https://www.mortgageconnectlp.com


Aidium — A modern CRM and pipeline management system built specifically for mortgage teams to convert more leads with less friction. Visit: https://www.thinkaidium.com


Floify — A digital point-of-sale and document platform that simplifies borrower interactions, speeds closing, and reduces back-and-forth. Visit: https://www.floify.com


TrueWork — Provides fast, secure income and employment verification to support lender decisioning and speed approvals. Visit: https://www.truework.com


FundingShield — Offers anti-fraud tools, identity verification, and secure transaction protection to safeguard lenders and borrowers. Visit: https://www.fundingshield.com

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