About Win Win Lending
Your Partner in Success
Win Win Lending was built on a simple belief: the best financing comes from someone who has actually been in your shoes. Craig Winquist isn't just a lender — he's an active real estate investor who understands what it takes to close deals, manage properties, and build lasting wealth.
Craig Winquist
Founder & Principal Lender
Craig's Story
30 Years of Real Estate Mastery
Craig Winquist has spent over three decades immersed in every corner of real estate — as a buyer, seller, investor, flipper, landlord, and lender. That breadth of experience is what sets Win Win Lending apart from every other financing option on the market.
Over the course of his career, Craig has personally flipped more than 100 homes and currently owns and manages 25+ active rental properties. He holds a real estate license and has spent more than 10 years on the lending side, giving him a 360-degree view of what makes a deal work — and what kills it.
Craig founded Win Win Lending on a straightforward philosophy: financing should work for both sides of the table. When a borrower succeeds, the lender succeeds. That alignment drives every decision — from loan structure to communication to closing timelines.
Today, Win Win Lending specializes in investment purchases, refinances, and niche financing products that traditional lenders won't touch — including condotel financing in markets like Myrtle Beach, Orlando, Miami, and Knoxville.
What We Stand For
The Win Win Philosophy
Investor-First Perspective
Craig doesn't just lend — he invests. Every loan decision is made through the lens of someone who has been on your side of the table, which means you get advice that's actually useful.
Transparent Process
No hidden fees, no complex jargon. From the initial discovery call through closing, you always know exactly where your deal stands and what comes next.
Niche Market Expertise
Where traditional lenders say no, we find a way. We specialize in condotel financing, non-warrantable condos, and markets that require a lender who truly understands the local dynamics.
Long-Term Partnership
We're not here for a single transaction. Craig builds lasting relationships with investors, realtors, and lenders — because a win for you is a win for us.
Loan Programs We Offer
Fixed Rate Loans
Long-term stability for buy-and-hold investors who want predictable monthly payments.
Hard Money Loans
Fast, asset-based capital for time-sensitive acquisitions and fix-and-flip projects.
Bridge Loans
Short-term financing to bridge the gap between purchase and permanent financing.
Ground-Up Construction
From raw lot to finished property — we fund every phase of the build.
Where We Work
Niche Markets & Specialty Financing
Win Win Lending specializes in markets and deal types that traditional lenders routinely decline. Craig's deep familiarity with these markets means faster decisions and smarter structures.
Ready to Close Your Next Deal?
Reach out today and let's talk through your deal. Craig responds personally.
Get in Touch