Aaron Schiff

Aaron Schiff is a Southern California native entrepreneur and angel investor based in Venice Beach. He grew up in Los Angeles and graduated from the University of California, Santa Barbara (UCSB). Schiff has built a notable career as a serial entrepreneur in the insurance technology and digital marketing spaces, with a particular focus on leveraging technology to simplify complex consumer experiences.

Before entering the startup world, Schiff built his entrepreneurial foundation through early ventures in digital marketing. In 2011, he founded Adrenalads, an internet advertising network that reportedly generated $6,000 in its first three days and scaled to several million dollars in annual profit. His success in the search engine marketing space and ability to build profitable businesses from the ground up established him as a resourceful operator in the digital ecosystem.

In October 2012, Schiff joined Anthem Venture Partners as an Entrepreneur in Residence (EIR), where he advised multiple startups and deepened his knowledge of the venture capital landscape. This two-year tenure (through August 2014) positioned him at the intersection of entrepreneurship and venture investing, informing his later work both as a founder and angel investor.

In August 2014, Schiff co-founded Matic Insurance Services alongside Benjamin Madick, serving as CEO through 2018. Matic pioneered the integration of homeowners insurance into the digital mortgage workflow, becoming the first company to incorporate HOI into the e-mortgage process. The platform automatically extracted borrower and property data from loan origination systems, normalized coverage requirements, and facilitated competitive bidding among insurance carriers. Under Schiff's leadership, Matic raised a $7 million Series A round in December 2017 led by Mr. Cooper (formerly Nationstar), validating the company's model of embedding insurance into lending infrastructure. His work at Matic earned him recognition as a 2018 HousingWire Rising Star, an award honoring mortgage industry leaders and innovators under 40.

Following his tenure at Matic, Schiff transitioned to EasyHealth as Chief Operating Officer, where he currently leads operational strategy. EasyHealth redesigns Medicare by connecting insurance distribution with care delivery, aiming to improve health outcomes for Medicare-eligible populations. The company has raised $135 million in equity and debt from investors including Anthemis Group, QED Investors, Victory Park Capital, Nationwide Ventures, Healthy Ventures, Brewer Lane, and Operator Partners. Schiff lives in Venice, California with his German Shepherd, Maxwell, whom he adopted from a local shelter.

Aaron Schiff invests as an angel investor with a focus on seed-stage companies, particularly those operating at the intersection of technology and traditional industries. His investment interests reflect his operational expertise and include apps, mobile platforms, marketing technology, internet businesses, and insurtech ventures. Schiff appears to favor companies that leverage technology to simplify complex consumer experiences, consistent with his own entrepreneurial journey.

Based in Los Angeles, Schiff is active in Southern California's "Silicon Beach" startup ecosystem and serves as an advisor to multiple early-stage companies. His approach to investing appears relationship-driven, with investments often occurring through networks built during his time as an EIR at Anthem Ventures and through his operational roles. Schiff brings hands-on experience in scaling digital platforms, building go-to-market strategies, navigating regulated industries (insurance), and raising venture capital.

• Matic Insurance - Board Member (joined April 2014)
• Multiple early-stage startups in Southern California (specific companies not publicly disclosed)