Second Alpha

Second Alpha Partners is a private equity firm based in New York, founded in 2012, that specializes in secondary investments in private companies. The firm acquires shares and convertible securities from existing shareholders, including founders, executives, and investors, and also provides direct capital investments in private firms. Second Alpha primarily focuses on growth equity opportunities in the telecommunications, media, and technology sectors, targeting companies in the United States and Canada. The firm is known for its strategic approach to investing in late-stage venture-backed and middle-market enterprises, with a particular emphasis on software and technology-enabled services.

Richard Brekka

Managing Partner and Co-Founder

Eugene Galantini

CFO and CCO

Joseph Hickey

Analyst

Ryan Kober

Senior Principal

Jim Sanger

Managing Partner and Co-Founder

James Sanger

Co-Founder and Managing Partner

Nico Serpa

Associate

4 past transactions

Bespoke Post

Series B in 2021
Bespoke Post is a subscription service that curates themed boxes of lifestyle products for men, focusing on enhancing their everyday experiences. Each month, subscribers receive an email showcasing a selection tailored to their preferences, allowing them to customize their order by adjusting colors, sizes, or opting to skip a month without any charge. The offerings include limited edition items across various categories such as grooming, style, food, drink, and gear. In addition to the monthly boxes, Bespoke Post also features a shop with unique standalone products. The company emphasizes a hassle-free experience with free shipping and easy returns, creating an accessible way for men to discover and enjoy high-quality goods.

SmarterTravel

Series B in 2021
SmarterTravel, a subsidiary of TripAdvisor, operates a portfolio of high-traffic online travel sites designed to assist travelers in finding suitable trips at competitive prices. The company offers a platform that features personalized travel recommendations and facilitates instant booking. Additionally, SmarterTravel provides a subscription service that grants members access to discounted hotel rates and other benefits, enhancing the travel planning experience. Alongside expert travel tips, inspiring destination stories, and timely news, SmarterTravel is committed to innovation and improvement, fostering a collaborative environment that empowers its team to challenge conventional approaches.

HealthCare.com

Series B in 2019
HealthCare.com operates an online platform designed to educate consumers about healthcare and Medicare insurance options. Founded in 2006 and based in Miami, Florida, the company enables users to search for and compare various health plans, access healthcare resources, and utilize tools for understanding coverage options. As an independent, advertising-supported website, HealthCare.com generates revenue through leads, clicks, calls, and applications, and may receive compensation from advertisers for sponsored products and services. It is important to note that HealthCare.com does not act as a broker or agent in the sale of insurance products and does not provide a comprehensive listing of all available companies or products. The company also has additional offices in New York City, Indianapolis, and Guatemala City.

EverQuote

Series B in 2017
EverQuote is an independent online insurance marketplace that enables consumers to compare quotes for various types of insurance, including auto, home, and life insurance. The company connects consumers with a network of insurance providers through its data-driven platform, streamlining the process of finding suitable coverage at competitive prices. By leveraging technology and data science, EverQuote aims to simplify insurance shopping, saving time and money for both consumers and providers. The company's services are offered free of charge to users, fostering an accessible environment for individuals seeking personalized insurance options.
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