Nov 2026, EUGENE, OR – Freestone Mortgage is proud to announce that Chris Watkins has joined the team as a loan officer serving the Eugene and surrounding Southern Oregon markets. With a unique background as both a seasoned real estate investor and mortgage advisor, Watkins brings a rare combination of firsthand investment experience and creative client engagement strategies to his partnership with Freestone.

“Chris represents exactly the kind of advisor we’re building Freestone for,” says Riley Anderson, co-founder of Freestone Mortgage. “He’s someone who got into this business to genuinely help people. His ability to connect his own real estate investment journey with his clients’ goals is exactly the kind of authentic, value-driven approach that separates great advisors from order-takers.”

From Accidental Investor to Trusted Advisor

Watkins entered the mortgage industry three years ago during one of the most challenging periods in recent history, driven by a desire to help others achieve the same financial freedom through real estate that his family had experienced. His background includes two decades of hands-on real estate experience—from building and renovating properties to managing his own rental portfolio.

“I became an investor almost by accident,” Watkins explains. “We bought a house in Washington in 2006, and when we moved to Oregon in 2010, the market was terrible. Instead of selling at a loss, we held onto it as a rental. Almost 20 years later, we still own that property, and I’ve used the equity to buy two more. That experience of building wealth through real estate, step by step, is what I want to help my clients achieve.”

His recent investments tell the story of someone who practices what he preaches. In the last two years alone, Watkins has purchased multiple properties in the Eugene area, including a fix-and-flip, a property he’s converting to a rental with plans for a lot split, and an Airbnb duplex. This active involvement in today’s market gives him an unmatched perspective on both the opportunities and challenges his clients face.

Choosing Small and Local Over Corporate Conglomerates

After interviewing with several companies: including brokerages and retail lenders, Watkins made a deliberate choice to join a smaller broker rather than pursue opportunities with larger national lenders.

“Over the last few years, I’ve watched real estate and lending companies merging and consolidating to try and gobble up market share,” Watkins observes. “I believe homebuyers are losing out left and right in the process as true client service is replaced with call-center efficiency. I was tempted by the product offerings and promised efficiencies of a national retail lender, but found the reality clunky, frustrating, and more expensive.”

What particularly drew Watkins to Freestone was the platform’s support for originality and its rejection of corporate homogenization. Known for his exceptionally creative and engaging content marketing, Watkins found that traditional lenders either restricted or standardized his approach.

“I want to share my story and my journey authentically,” he explains. “Everything I put out there, I want it to either be genuinely entertaining or add real value—or both if I can pull it off. I’m so excited to strip away the layers of corporate crud to be able to give the highest level of service directly to my clients, referral partners, and those just tuning in.”

What Changes for Clients and Collaborators

Watkins’ move to Freestone represents a significant upgrade in both service quality and product access. He’s candid about the limitations he experienced previously and enthusiastic about what he can now offer.

“With Freestone, I am freed up to take the hands-on personal consultant role that I excel in—to bring value to everyone who trusts my opinions and experience. Freestone gives me the diagnostic tools to sit with anyone and really diagnose their concerns and hang-ups, then I have the products and options to prescribe the right path forward.”

His approach centers on making complex information accessible and actionable —the kind of insights that real estate agents, financial advisors, and other professionals can immediately use with their own clients.

Technology Meets Personal Touch

Watkins is clear about his service philosophy: technology should enhance human connection, not replace it.

“People don’t care what you know until they know that you care,” he states. “Technology is great, but only where it serves to make me a better steward of my client’s money and time. Freestone has the perfect blend of cutting-edge tools that enable me to focus on the people in front of me.”

This philosophy extends to his work with clients at every life stage, particularly those in or approaching retirement who require an extra level of care and attention.

“There’s another level of care required when working with people who have worked and saved for decades to be able to live comfortably and confidently in retirement,” Watkins notes. “I’ve always been focused on being an educator and advisor first, willing to prescribe the best course of action for each individual situation, not just providing a one-size-fits-all product.”

Looking Ahead

Watkins is already planning educational initiatives, including developing a comprehensive investor guide for Freestone clients and participating in the company’s upcoming Real Estate Investor Summit in February 2026 —an event designed to educate those hesitant to take their first steps into real estate investing.

“With the average age of first-time homebuyers now at 40, there’s essentially a 20-year gap of people who should be investing in real estate but aren’t,” he notes. “My goal is to bridge that gap by showing people that getting started is more accessible than they think.”

For loan officers considering their next move, Watkins’ story illustrates what’s possible when creativity meets capability, and when a company’s structure supports rather than restricts an advisor’s authentic voice. His decision to choose a smaller broker over a larger national lender speaks to a growing recognition that bigger isn’t always better—especially when it comes to genuine client service.