Upside Partners
Startup DNA at Corporate Scale



Our Team

Successfully bridging corporate and startup worlds requires bringing together expertise and perspectives from many different fields. Based in the San Francisco Bay Area, home to Silicon Valley, our team of experienced industry practitioners delivers a unique blend of corporate & entrepreneurial, operational & strategic, and generalist & fintech-specific expertise.


Mike Sigal

Mike is a Co-Founder of Upside Partners. Mike also serves as a Venture Partner at 500 Startups Fintech Fund.  With over 230 investments in 26 countries, including Credit Karma, Grab, RealtyShares, Simple (acquired by BBVA) and Stripe, 500 Startups is the world’s most active early-stage venture fund and accelerator supporting the digital transformation of financial services.

Previously, Mike served as Founding Executive Producer of SWIFT’s Innotribe Startup Challenge and Industry Challenge programs which have resulted in an estimated $1B in investments, acquisitions and partnerships between participating startups, SWIFT’s member institutions and FinTech investors globally.  The methodologies Mike developed to support the Innotribe Challenges represent the cornerstone of Upside Partners’ methodology.

Mike’s spent 25 years working in the global startup ecosystem as an entrepreneur & innovation advisor, including as founder of 7 companies (3 exits, 1 IPO) and advisor to dozens of institutions on implementing startup ecosystem inspired innovation strategies. He’s an active startup mentor and frequent speaker at startup and FinTech conferences.


jelena ewart

Jelena is a Co-Founder of Upside Partners. She serves on the Board of Directors of San Francisco Federal Credit Union and on the Advisory Board of Wirecutter Money, a New York Times company. Jelena was recently recognized as one of Innovate Finance’s global Fintech Powerlist senior leaders.

Previously, Jelena was a General Manager and senior executive at NerdWallet, a San Francisco-based Fintech company still privately held at a valuation of $500MM+. At NerdWallet, Jelena built and grew the cross-functional Credit & Banking verticals to $100MM in annual run rate, and was a key member of the strategic and product leadership at the company.

Jelena also served as a Fintech investor at 500 Startups, the world’s most active Fintech investor.

A multiple International Math Olympiad medalist with a professional degree in Architecture and a nearly-complete BFA in Music Performance who also worked in 3D printing and digital fabrication, investment banking, and advisory for both startups and incumbents in financial services, Jelena has no shortage of hard-won lessons from the trenches to support clients in reaching their innovation goals.