
Second Alpha
276 Fifth Avenue, Suite 801, New York, NY, 10001, United States
Overview
Second Alpha Partners is a New York based private equity firm that makes secondary investments in private companies, purchasing shares from existing shareholders – founders, executives, angels, VCs or corporate investors. The firm buys shares and convertible securities on a secondary basis and also invests capital directly in private companies. The firm focuses its investments towards US and Canada based companies within telecommunications, media and technology sectors.
- Total investments
- 7
- Lead investments
- 2
- Investments · 12mo
- 0
- Active investors
- 4
Sector focus
- Finance
- Financial Services
- Venture Capital
Investment portfolio
- tvScientific
Participated · Series B · Feb 2025
tvScientific is a performance advertising platform for connected TV (CTV) that focuses on driving measurable outcomes for advertisers. Its core product is a patented suite of technologies around identity, outcome measurement, and ML/AI-driven TV outcome optimization. The company has been issued six patents to date and says it has helped hundreds of advertisers, including Foot Locker, Rare Beauty, EA, Scopely, Dream, Brightside, Earnin, Britbox, Gorjana, and Weight Watchers. The CTV market is growing rapidly by tens of billions of dollars compared to linear TV, and tvScientific aims to position CTV as a performance rival to search and social. With the new funding, tvScientific plans to scale its go-to-market teams and continue building its technology to make performance capabilities table stakes in CTV. The company raised $25.5 million in a Series B to support these plans and expand its customer base. Management targets a tenfold increase in customers within two years as part of its strategy to expand the Performance TV category. tvScientific is a Pasadena, CA–based performance advertising platform for connected TV that enables advertisers to buy and execute performance CTV campaigns with major inventory partners including Paramount+, Hulu, Discovery, ABC, CBS and NBC. The platform introduced the ability to buy CTV campaigns on a Cost-Per-Outcome basis, enabling advertisers to purchase media based on CPA, ROAS, sales and post-CTV campaign traffic rather than simple reach & frequency or MMM models. Customers include Experian, MoneyGram, Crocs, Groupon and Fender. Led by co-founder and CEO Jason Fairchild, the company raised $9.4M in convertible note financing in February 2024. Backers included S4S Ventures, BDMI, Progress Ventures, NBCU/Comcast, Norwest Capital Partners, Aperiam Ventures and Hearst Ventures. The company intends to use the funds to expand operations and accelerate development and product efforts. tvScientific provides a performance advertising platform built for connected TV (CTV) that aims to make TV advertising accessible and measurable for brands and apps of all sizes. Its self-managed solution is custom-built for performance marketers, simplifying and automating TV buying and optimization. The platform leverages large-scale data to prove the actual value of TV advertising. The company plans to use new funding to grow its customer base and continue innovating the product. It also intends to hire across engineering, product, data science, marketing, sales and other departments to support expansion. tvScientific was founded by Bill Gross, Jason Fairchild, Kent Wakeford and David Koye and is based in Pasadena, CA. tvScientific launched a Connected TV buying, measurement, and attribution platform designed to make TV advertising accessible and measurable for businesses of all sizes. The self-serve platform combines fully optimized buying with comprehensive measurement and proprietary deterministic ID technology to match CTV ad exposure to site visitations and performance. It offers advanced audience targeting (over 15K unique customer segments), direct access to more than 90% of premium CTV publishers, and real-time optimization based on direct attribution. tvScientific connects buyers to hundreds of premium CTV inventory sellers and data providers across partners such as SpotX, Magnite, OpenX and Samsung and runs on devices including Samsung, Vizio, and Roku. The company positions itself to capture a portion of the $72 billion TV advertising market and cites 200 million CTV viewers in the U.S. as part of its market opportunity. tvScientific is an Idealab company co-founded by Bill Gross and Jason Fairchild and has raised $1.5 million in seed funding.
- Healthcare.com
Participated · Series C · Feb 2022
HealthCare.com operates a digital, data-driven insurtech platform that matches individuals to a wide array of healthcare products using deep data assets and AI algorithms. The company develops and markets a portfolio of proprietary direct-to-consumer insurance and pharmacy plan products. It aims to simplify discovery, selection, purchase and use of health insurance and other healthcare-related products across every life stage. HealthCare.com has stated plans to expand its direct-to-consumer insurance and pharmacy initiatives and to accelerate development of its AI platform. The company was founded in 2014 and is headquartered in New York City and Miami, Florida. Recent financing activity reflects substantial capital support for its growth plans. HealthCare.com operates a digital healthcare platform that leverages deep data assets and AI algorithms to match individuals to a wide array of healthcare products, including proprietary insurance and pharmacy plans and customizable insurance bundles. The platform supports multi-product purchase options in a single transaction and emphasizes improving the end-to-end consumer healthcare experience. The company says it helped millions of people connect to a healthcare product and reported direct-to-consumer enrollments up 97% in 2021. HealthCare.com has grown its distributed workforce to more than 370 employees (a 130% increase since January 2021) and operates across more than 15 U.S. states plus Guatemala, Thailand, and the Netherlands. The company plans to accelerate investment in data science, product development, and engineering and to hire for several key roles as it scales. HealthCare.com operates a data-driven online shopping platform that enables American consumers to enroll in individual health insurance and Medicare plans. The company also develops and markets a portfolio of proprietary direct-to-consumer health and supplemental insurance products under the Pivot Health brand. It combines technology, engineering and data-science to streamline insurance shopping and product development. Founded in 2014 by Howard Yeh, Jeff Smedsrud and Jose Vargas, the business is focused on expanding its consumer experience solutions. HealthCare.com plans to use new capital to fund technology, engineering and data-science investments and to accelerate development and marketing of its proprietary insurance products. The company has raised over $27M in total capital to date. HealthCare.com is a Miami, FL-based search and comparison engine that helps consumers find and purchase personal health insurance plans. Led by CEO Jeff Smedsrud, the platform offers a selection including virtually all state-based exchange plans, federal exchange plans and many private, off-exchange plans. Consumers can compare costs and subsidies for free and buy insurance online, over the phone with a licensed advisor, or in person with a local agent. The company plans to use the Series A proceeds to continue building out its consumer interfaces and service offerings and to expand its reach in the online healthcare market. HealthCare.com completed a $7.5M Series A round in November 2014. HealthCare.com operates online tools that let consumers compare, customize and save money on health insurance plans. The company’s core product is a health insurance search and comparison platform that includes plan customization features. It plans to launch additional health insurance search and comparison tools and to offer private-label supplemental plans that fill coverage gaps caused by high deductibles. Management says the company will use new financing to expand operations and roll out these tools. The site also hosts a care provider directory with more than 1.2 million listing profiles. HealthCare.com is based in Miami, FL.
- Bespoke Post
Participated · Series B · Oct 2021
Bespoke Post is a NYC-based multi-category e-commerce retailer that delivers curated goods and guidance through a monthly membership and an e-commerce shop. The company was founded in 2011 by Steve Szaronos and Rishi Prabhu. It serves a membership base of more than 300,000 members. Bespoke Post combines curated product boxes with an online storefront. The company intends to use new funding to seek out small brands, launch retail partnerships, and invest in its data science capabilities. The recent fundraise is intended to support those strategic initiatives. Bespoke Post curates 10–20 themed boxes each month featuring artisanal products across categories like style, travel and cocktail-making, and recommends different boxes to members based on their interests. Members receive a new box suggestion monthly with no obligation to buy; boxes cost $45 while the contained products have a retail value north of $70. The company emphasizes curated selections from brands not typically found on mainstream shelves or large marketplaces. Bespoke Post launched in 2012 and grew to a team of nearly 40 people with more than 100,000 subscribers in the U.S. and Canada before raising its Series A; about 93% of subscribers are men. The startup plans more hiring, expanded product offerings and additional partnerships. Current operating metrics disclosed in the article are subscriber count, team size and the male-dominant customer mix. Bespoke Post offers themed monthly boxes (the "Box of Awesome") for about $45/month with shipping included, each box typically retailing for over $70. Customers receive an email about the current box and can opt out as often as they want, a modification of the traditional subscription model. Past boxes have included shave kits, travel themes, cocktail sets, shoeshine kits and weekender packs; the company works with large brands (including Diageo) and smaller designers, sometimes custom-making products. The service expanded into Canada, where prices increase by $15–$25 depending on location to cover shipping, duties and taxes. Though focused on men, 10–15% of subscribers are women. The company has grown its team from two to seven and is hiring; the founder previously hinted at an approaching $1M annualized run rate, said subscriber count has more than doubled since that time, and reported consistent double-digit growth. Bespoke Post plans to introduce a higher-price box option and eventually expand from subscription into a broader e-commerce offering where customers can buy individual products or experiences.
- SmarterTravel
Led · Series B · Sep 2021
SmarterTravel provides personalized travel recommendations and targeted travel content, leveraging proprietary artificial intelligence to surface information and discounts to consumers. The company operates an email-driven business with 7 million newsletter subscribers and publishes articles across travel topics to inform users about restrictions, deals and trip inspiration. Originally founded as HopJump in 2018 by CEO Jordan Staab, the company rebranded to SmarterTravel to reflect a renewed focus on an informative online travel experience. In 2020 the company acquired assets from TripAdvisor’s travel division, including Airfarewatchdog, Family Vacation Critic and Oyster, which helped it navigate the pandemic. The company has about 50 employees, plans to hire more, and will use the new funding to increase brand awareness and build new travel products. Financially, SmarterTravel reported revenue growth of eight times in the past 12 months, is profitable, and has fresh capital to lean into growth.
- EverQuote
Participated · Series B · Feb 2017
EverQuote operates an online data-and-technology insurance marketplace that connects drivers with agents and carriers using a scientific, data-driven approach to match consumers with suitable price and coverage. The platform applies big data and machine learning to drive down costs for insurance providers while helping consumers find individualized insurance options. The company intends to use the new funding to accelerate growth of its marketplace. Since the funding close it has grown its workforce to over 200 employees, opened a second office in Woburn, MA, and plans to hire another eighty employees by 2018. EverQuote also plans to expand its presence into home and life insurance. The company is led by CEO Seth Birnbaum and was founded in 2011. EverQuote operates an insurance marketplace that uses proprietary technology and data to match, advise and connect insurance shoppers with carriers and agents both online and offline. The company serves many of the largest U.S. underwriters and over 5,000 insurance agencies. Since inception it has grown to 5 million consumer visits per month and has made over 50 million referrals, which the company says result in over $3 billion of premiums for carriers and agents and an estimated $500 million in consumer savings. In 2016 EverQuote launched EverDrive, a free iOS and Android safe driving app to help consumers identify and correct driving habits. The company intends to use the new funds to accelerate sales expansion and product development. EverQuote was founded in 2011 by CEO Seth Birnbaum and is based in Cambridge, MA.