About
Michael O'Brien is a fintech-focused angel investor and the founder of O'Brien Angel Syndicate, a 150-member network of finance professionals investing in early-stage fintech and proptech startups. With $15M+ deployed across 25 investments since 2018, Michael has established himself as a go-to investor for founders disrupting financial services.
Michael's investing career follows a 25-year Wall Street run including roles as Managing Director at Goldman Sachs (Merchant Banking), JP Morgan (M&A), and most recently as COO of a multi-family office with $3B AUM. This institutional finance background gives him unique insight into the regulatory landscape, distribution channels, and partnership opportunities for fintech startups.
He writes personal checks of $50K-$150K and leads syndicate rounds of $250K-$1M. Investment focus areas include: payments infrastructure, embedded finance, wealth management automation, real estate technology, and regulatory technology. He explicitly avoids crypto and blockchain investments.
Michael's value-add extends beyond capital. He's known for making introductions to potential customers within financial services, providing regulatory guidance, and helping founders understand the nuances of selling to enterprise financial institutions. His portfolio companies have collectively raised over $200M in follow-on funding.
Notable investments include PaymentHub (Series B, acquired by Stripe for $90M), WealthTech Pro (Series A, $18M raised), and PropFlow (seed, currently raising Series A). Two portfolio companies have achieved unicorn status.
A graduate of Wharton (BS/MBA) and CFA charterholder, Michael splits time between New York and Miami. He hosts quarterly Fintech Founders dinners connecting his portfolio companies with finance industry executives.
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