Led · Series B · Feb 2026

Pay With Spire develops a modern Pay-by-Bank solution that rides on existing credit card rails, giving merchants near-universal acceptance while lowering payment costs. The platform works across more than 200,000 point-of-sale terminals without requiring new hardware or software integrations. Shoppers can pay via a mobile app, physical card, or other digital methods, keeping the checkout flow familiar. For merchants, the system delivers actionable transaction data in addition to cost savings. The company recently raised a $10 million Series B round and brought in former Ally Bank CFO Jennifer LaClair as its new CEO. Pay With Spire plans to devote the fresh capital to client acquisition and to scaling the infrastructure needed to extend Pay-by-Bank access to more retail verticals.

Led · Seed · Sep 2023

Layup is a New York-based provider of bank-offered prize-linked savings accounts (PLSAs) targeting sports fans. The company has created PLSAs by offering competitive, chance-based sports games that reward saving with increased opportunities to participate in equal-odds sports-based games. Its product aims to provide sports-betting-like engagement without the financial downside, promoting savings instead of losses. A beta version of Layup is currently available on the Apple App Store and the Google Play Store. Led by CEO Owen Monagan and CTO Oisin Tiernan, the company plans to expand product capabilities, recruit talent, and market its game-based savings application to sports fans and other end users. Layup completed a $2.3M Seed financing to support those initiatives.

Participated · Series B · Apr 2022

Prizeout is a New York-based adtech company founded in 2019 and led by CEO David Metz. The company works across gaming, neobanks, crypto, the gig economy, payroll and finance to convert withdrawals into growth solutions for e-commerce and retail businesses. Through exclusive partnerships Prizeout offers users bonus offers on brand favorites while providing a fast, secure and curated experience. On the merchant side it has secured partnerships with thousands of national and local brands via gift card partnerships, point-of-sale integrations and proprietary gift-card technology. Prizeout sells a B2B2C offering that embeds these incentives into partner flows and plans to expand that reach, advance product innovation and grow headcount following its latest funding.

Led · Series A · Nov 2021

TheDrop.com operates a curated, multi-brand marketplace that syncs inventory across hundreds of streetwear, sneaker and skateboard brands and boutiques, providing 70+ new 'drops' daily. The company uses proprietary in-house software to synchronize inventories (the article cites 300+ brands and over 30 top shops, and elsewhere references 700+ brands) and to surface real-time trend intelligence for a $200 billion youth market. The platform positions itself as a DTC extension for brands while serving multi-brand shoppers who discover emerging designers. TheDrop.com plans to use its Series A proceeds to launch new content and brand storytelling strategies, build real-time personalization across the user experience, and expand its DTC ecosystem into new parts of the world. It is turning on localized instances of its marketplace in a growing number of international markets to expose products to new global audiences. The company says many one- and two-location boutique retailers have relied on the platform during the pandemic to extend their digital reach.