Richard Brekka

Managing Partner, CEO and Co-Founder at Second Alpha Partners

📍 New York, New York, United States🔄 Updated September 2026💼 10 investments📅 20 years investing🗓 Last invested Oct 2019
VC🌍 United States
10
Total investments
1
Early stage
2
Mid stage
4
Late stage
20y
Years active

Portfolio

9 investments · sorted by recency
All investments
Early stage
Mid stage
Late stage
Shareholder
Oct 2019
Founded by industry experts in 2014, Healthcare.com is a data-driven, intelligence-informed marketplace where millions of consumers have explored, shopped for and enrolled in health insurance and Medicare plans. We put care, data, and a decade of experience into helping you choose the right plan. With us you can easily shop health plans for individuals, for families, for seniors. Trusted by 10 million customers a year, Healthcare.com is the data-driven choice that matches you to the right health insurance plan. We use proprietary data and machine learning technology to match consumers with distributors, ensuring each consumer gets enrolled in the right plan for them and their families. Healthcare.com also operates Pivot Health, an insurance marketing company and healthcare services provider that offers a variety of coverage options to consumers on behalf of top-ranked insurance carriers and healthcare organizations. We develop custom health insurance programs and coverage solutions in partnership with insurance carriers. In addition to our own solutions, we have put together a portfolio of non-proprietary health insurance and healthcare solutions that we believe meet the needs of our individual members. Our products range from short-term medical insurance, dental and vision, supplemental indemnity, and accident and illness products.
mid stageInsurance
Shareholder
Mar 2019
Coursera was launched in 2012 by Andrew Ng and Daphne Koller with a mission to provide universal access to world-class learning. Today, it is one of the largest online learning platforms in the world, with 197 million registered learners as of December 31, 2025. Coursera partners with over 375 leading university and industry partners to offer a broad catalog of content and credentials, including courses, Specializations, Professional Certificates, and degrees. Coursera’s platform innovations — including generative AI-powered features like Coach, Role Play, and Course Builder, and role-based solutions like Skills Tracks — enable instructors, partners, and companies to deliver scalable, personalized, and verified learning. Institutions worldwide rely on Coursera to upskill and reskill their employees, students, and citizens in high-demand fields such as GenAI, data science, technology, and business, while learners globally turn to Coursera to master the skills they need to advance their careers. Coursera is a Delaware public benefit corporation and a B Corp.
Shareholder
Jul 2017
We are the world’s leading ad exchange for data and identity. With industry-leading technology, premium service, and huge scale, we bring greater reach for buyers and higher revenue for publishers — across every format, from mobile to CTV. That's the power of OpenX.
Investor
Dec 2014
HotChalk, Inc.
Shareholder
2011
Everbridge empowers enterprises and government organizations to anticipate, mitigate, respond to, and recover stronger from critical events. In today’s unpredictable world, resilient organizations minimize impact to people and operations, absorb stress, and return to productivity faster when deploying critical event management (CEM) technology. Everbridge digitizes organizational resilience by combining intelligent automation with the industry’s most comprehensive risk data to Keep People Safe and Organizations Running™.
Board Member
Mar 2007
Comprehensive Data Encryption and Device Management The MOBILE ARMOR DATA ENCRYPTION & DEVICE MANAGEMENT SUITE is a comprehensive, easy-to-use, data encryption solution for all mobile computing devices including PCs, laptops, tablets, notebooks, smartphones, CDs and USB flash drives. Our centrally managed, policy driven solution was architected to help organizations meet today’s stringent regulatory compliance mandates for data protection. The Mobile Armor Solution uses fast AES 256 FIPs certified data encryption that is built on the Mobile Armor Common Development and Management Platform that has a unified data repository with a central management policy server and console. The Mobile Armor Suite is fully integrated and modularized, enabling customers to seamlessly implement and manage multiple types of encryption from a single management console and server. The Mobile Armor Suite provides: • FDE - hardware and software based encryption for PCs, and laptops • SED - management, authentication, and reporting of Seagate and OPAL drives • FFE - f iles, folders, email attachments, USBs and CD encryption • RME - USB drive encryption • Port and device control The Mobile Armor Suite contains more government certifications and approvals than any other data encryption solution, including FIPS 140-2 Level 2& Level 3, Common Criteriea EAL4+, and is on the DARTT list for approved encryption vendors to sell to the US Government.
Board Member
Jan 2007
Appia’s mission is to help our customers realize the many benefits of IP technology for far less than the cost of an in-house implementation. Our managed solutions simplify your operations and save capital and operating dollars. Our customers range in size from one to 60,000 employees and from one to over 200 locations. They represent all the major verticals, including construction, education, engineering, entertainment, government, healthcare, legal, manufacturing and nonprofit. Appia has been recognized as one of the fastest-growing private companies in America (Inc., 2007, 2008, 2009, 2010, 2011), one of the fastest-growing solution providers in the technology industry CRN, 2009, 2010, 2011), and one of the top managed service providers in the world (MSPmentor, 2009, 2010, 2011, 2012). Headquartered in beautiful Traverse City, Michigan, we have operations in multiple major cities across the United States.
Board Member
Jan 2006
June Media is a leading content provider for women as well an affiliate network that enables its advertising clients to generate high volumes of top-quality customer leads and sales on a pay-for-performance basis. June Media is a privately held company with offices in both New York and Chicago.
early stageOnline Media
Board Member
Jan 2006
TERAGO provides business customers and partners with secure, reliable and innovative wireless connectivity services with speed, flexibility and service levels that are unmatched by our competition.
Experience · 13 entries
All (13)
Investments (10)
Founder (1)
Board (5)
2019
Shareholder
Oct 2019
Founded by industry experts in 2014, Healthcare.com is a data-driven, intelligence-informed marketplace where millions of consumers have explored, shopped for and enrolled in health insurance and Medicare plans. We put care, data, and a decade of experience into helping you choose the right plan. With us you can easily shop health plans for individuals, for families, for seniors. Trusted by 10 million customers a year, Healthcare.com is the data-driven choice that matches you to the right health insurance plan. We use proprietary data and machine learning technology to match consumers with distributors, ensuring each consumer gets enrolled in the right plan for them and their families. Healthcare.com also operates Pivot Health, an insurance marketing company and healthcare services provider that offers a variety of coverage options to consumers on behalf of top-ranked insurance carriers and healthcare organizations. We develop custom health insurance programs and coverage solutions in partnership with insurance carriers. In addition to our own solutions, we have put together a portfolio of non-proprietary health insurance and healthcare solutions that we believe meet the needs of our individual members. Our products range from short-term medical insurance, dental and vision, supplemental indemnity, and accident and illness products.
mid stageInsurance
Shareholder
Mar 2019
Coursera was launched in 2012 by Andrew Ng and Daphne Koller with a mission to provide universal access to world-class learning. Today, it is one of the largest online learning platforms in the world, with 197 million registered learners as of December 31, 2025. Coursera partners with over 375 leading university and industry partners to offer a broad catalog of content and credentials, including courses, Specializations, Professional Certificates, and degrees. Coursera’s platform innovations — including generative AI-powered features like Coach, Role Play, and Course Builder, and role-based solutions like Skills Tracks — enable instructors, partners, and companies to deliver scalable, personalized, and verified learning. Institutions worldwide rely on Coursera to upskill and reskill their employees, students, and citizens in high-demand fields such as GenAI, data science, technology, and business, while learners globally turn to Coursera to master the skills they need to advance their careers. Coursera is a Delaware public benefit corporation and a B Corp.
2017
Shareholder
Jul 2017
We are the world’s leading ad exchange for data and identity. With industry-leading technology, premium service, and huge scale, we bring greater reach for buyers and higher revenue for publishers — across every format, from mobile to CTV. That's the power of OpenX.
2014
Investor
Dec 2014
HotChalk, Inc.
2012
Managing Partner and Founder
Dec 2012
Second Alpha Partners is a private equity firm focused on secondary investments, mainly purchases of direct interests in private companies from existing shareholders. The firm also invests capital directly in private companies that meet its investment criteria, usually in tandem with making secondary purchases of shares. Second Alpha Partners has offices in New York. For more information visit SecondAlpha.com.
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Investment activity
2006–2019 · 10 investments
20062200722010120111201412017120192
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