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.

• 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.

• 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

In this episode of MikedUp, we sit down with Lisa Lang, Executive Vice President and Head of Capital Bank Home Loans, to explore how creative technology and sustainable innovation are shaping the future of the mortgage industry. Lisa brings a wealth of experience, deep market insight, and a proven track record of leadership to this conversation — making it a must-listen for anyone passionate about the evolving housing and lending landscape.

With decades of experience across every facet of the mortgage business, Lisa has dedicated her career to building systems that foster both growth and resilience. As a lifelong resident of the DMV area and a graduate of George Mason University, she understands firsthand how communities thrive when financial institutions are committed to progress and innovation. Today, Lisa leads Capital Bank Home Loans with a vision that blends technology, service, and social responsibility to deliver meaningful change.

Lisa shares her perspective on what it takes to lead a modern home loans division, from developing forward-thinking products to implementing technology that meets borrowers where they are. She also emphasizes the human side of mortgage lending — empowering teams, building trust with clients, and ensuring every decision reflects the long-term health of the community.

Beyond her professional expertise, Lisa is deeply involved in breast cancer advocacy, bringing the same passion she applies in the mortgage space to causes that touch people’s lives directly. This balance of career leadership and personal dedication gives Lisa a unique lens on sustainability — not just in business processes, but in creating lasting impact for families and neighborhoods.

This episode explores:

• The role of creative technology in driving efficiency and accessibility in mortgage lending

• Sustainable innovation strategies that keep communities strong and businesses thriving

• How leaders can align corporate goals with social responsibility

• Why the future of housing depends on trust, transparency, and forward-thinking solutions

• Lisa’s journey from local beginnings to national leadership in mortgage banking

Join us as we discuss how to build a future-ready mortgage ecosystem that empowers both lenders and borrowers. Whether you’re a mortgage professional, housing advocate, or simply curious about where the industry is headed, this conversation offers practical insights and inspiration.

This episode is made possible by our incredible sponsors who are helping transform the mortgage industry:

• Mortgage Connect – Leading provider of end-to-end mortgage solutions designed to streamline the lending process.
  Visit: https://www.mortgageconnectlp.com

• Aidium – A powerful CRM platform built specifically for mortgage professionals to manage relationships and drive growth.
  Visit: https://www.thinkaidium.com

• Floify – Simplifying the mortgage process with innovative point-of-sale technology that improves borrower experience and lender efficiency.
  Visit: https://www.floify.com

• TrueWork – Providing secure, instant income and employment verification to make lending decisions faster and more reliable.
  Visit: https://www.truework.com

• FundingShield – Protecting lenders and consumers from wire fraud and closing risks with advanc...

In this episode, we dive deep into how homebuying has changed — and where it’s headed — with Dan Richards, President of Flyhomes Mortgage. Dan’s story is one of bridging tech, finance, and real estate to create more accessible paths to homeownership, especially in a market that’s constantly shifting.

Dan joined Flyhomes in October 2022, bringing with him a rich background from SoFi (where he led the Home Loans unit and played a role in acquiring Wyndham Capital Mortgage), Homie, and many years at Academy Mortgage Corporation where he rose through roles in technology, growth, and strategic partnership. Before that, he worked with major tech companies like Microsoft, Google, and Nokia — all of which inform his view of what happens when you blend real estate, customer experience, and innovation.

• Dan’s view of how homebuying has evolved since the early 2000s — from heavy reliance on brokers to more lender-led, tech-enabled models.

• How regulation, credit expansion, and consumer expectations have shaped risks and tools in mortgage lending.

• The role of products like “Buy Before You Sell” and Cash Offers in helping buyers avoid common pitfalls, like selling too early or losing leverage in bidding wars.

• How Flyhomes is retooling its business (including selling or narrowing some product lines) to focus more sharply on mortgage services and less on home search tech in order to better serve both buyers and agents. GeekWire+2flyhomes.com+2

• Dan’s leadership lessons: how to grow with integrity, stay nimble, and make decisions that put customers first even when the market demands speed.

This conversation isn’t just about how to buy a home. It’s about reshaping expectations, unlocking tools that work for more people, and creating a homebuying journey that feels doable — not daunting — for today’s buyer. Whether you’re a loan originator, real estate agent, or someone thinking of buying your first home, there’s something here for you.

We’re grateful for the support of sponsors who help us bring you insights like this:

• Mortgage Connect – Offers comprehensive mortgage solutions across the full loan lifecycle: title, closing, valuation, and risk mitigation, helping lenders improve the borrower experience.
  Visit https://www.mortgageconnectlp.com

• Aidium – A modern CRM platform built specifically for mortgage professionals, helping teams manage leads, pipelines, and client relationships smarter.
  Visit https://www.thinkaidium.com

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