Matt Miles

Matt Miles is a real-estate capital markets executive and founder focused on residential real estate finance, private credit, and proptech. LinkedIn lists him in the San Francisco Bay Area with Flipside Lending and Michigan State University; California filing data for Flipside Lending LLC lists Matt Miles as manager and chief executive officer, with the company formed in Delaware and filed in California on September 13, 2024.

Before Flipside, Miles was Chief Capital Markets Officer at Anchor Loans, which announced his hiring on July 12, 2021. Anchor described him as bringing more than 20 years of real-estate capital markets experience, with a special focus on fix-and-flip lending and investment. Anchor also noted that he had founded Civic Financial Services, a fix-and-flip lender, and Aperture Real Estate Ventures, a proptech company focused on analytics and technology for fix-and-flip investing.

Earlier in his career, Miles was Head of Capital Markets and fix-and-flip Portfolio Manager at Sundae, a Partner at Wedgewood, and founder of Civic Financial Services while at Wedgewood. Before moving into operating roles, he spent 13 years at RBS Securities, formerly Greenwich Capital, most recently as Senior Vice President of Investment Banking and Principal Finance. Anchor’s announcement says he began his career at GE Capital and graduated from Michigan State University.

Miles also appears in startup-investor databases as an angel/individual investor. Wellfound describes him as an investment banker, founder, and advisor, and lists founder roles at Civic Financial Services, Western Bridge, Acceleration Motoring Club, and other ventures, plus advisor roles including Recess.

• Flipside’s current credit strategy is residential real-estate private credit rather than traditional venture capital: fix-and-flip loans, ground-up construction, bridge loans, rental property loans, and multifamily lending.
• Flipside’s stated positioning is operator-led lending: “As former investors ourselves, we understand how residential real estate investments work and the needs of our customers.”
• The firm says its lending team has “closed over $9B of investor loans,” and emphasizes urgency, tailored structures, transparency, and investor/operator experience.
• Fix-and-flip program parameters include up to 90% loan-to-cost, up to 100% of rehab costs, multifamily eligibility, and up to $5MM per property.
• Ground-up construction program parameters include single-family, condo, and townhome projects; up to 85% loan-to-cost; 12- to 24-month terms; and up to $5MM per parcel.
• In a prior Aperture / Property Coin context, Miles’ focus was tech-enabled real-estate investing: using proprietary software and operator experience to buy, renovate, and resell residential properties and make loans to other property investors.
• AngelMatch lists his investor markets as Android, FinTech, Real Estate, and Media and Entertainment, though public sources do not confirm a current active angel mandate or standard startup check size.