Gaingels

Gaingels is a venture capital investment firm founded in 2014 and based in Burlington, Vermont. It specializes in investing in companies led by LGBT+ founders and C-suite leaders across various stages of growth, as well as in established firms aiming to create more inclusive teams. With a global portfolio of over 130 companies and $70 million in investment capital deployed, Gaingels actively supports its portfolio by helping to identify and recruit diverse talent for leadership roles. The firm fosters a vibrant community of industry leaders, investors, operators, and entrepreneurs who are united in their mission to drive positive social change through business and successful investments.

Marc Baum

Investor

Jesse Curran

Principal

Ashley Flucas

Venture Partner

Max Frenkel

General Partner

Todd Havill

Research Operations and Principal, Investment

Surya Jayaweera

Angel Investor

Jennifer Jeronimo

CEO and General Partner

Jake Prigoff

General Partner

Peter Steinberg

General Partner

Alexandra Tanner

Investor

Lorenzo Thione

General Partner

Past deals in Ride Sharing

iRocket

Seed Round in 2022
iRocket is a manufacturer of fully autonomous reusable small launch vehicles designed for rapid landing and relaunch. The company emphasizes innovative design and reliability, aiming to provide low-cost access to space. By leveraging 3D printing and additive manufacturing technologies, iRocket addresses various inefficiencies within the space industry, facilitating advancements and innovations in space exploration.

Caribou

Series C in 2022
MotoRefi, Inc. operates an automotive refinance platform designed to help customers save on their car loans. By partnering with various local and community lenders, the company offers competitive loan rates and aims to reduce monthly payments, with customers typically saving an average of $100 each month. MotoRefi's secure digital platform allows users to assess potential savings and complete the refinancing process easily from home. The company handles all aspects of the transaction, including paying off the previous lender and retitling the vehicle, eliminating the need for customers to visit the DMV. Founded in 2016, MotoRefi is headquartered in Arlington, Virginia.

Flyp

Series A in 2022
Flyp is a company that operates an artificial intelligence platform focused on reselling used goods. It facilitates the sale of second-hand clothing by connecting individual resellers with a decentralized network. The platform provides automation software and supply chain management systems that empower these resellers to turn used items into cash. By enabling both enterprises and consumers to liquidate their items efficiently, Flyp aims to simplify the resale process and create a more sustainable marketplace for pre-owned goods.

WorkWhile

Series A in 2022
WorkWhile is a labor technology platform that helps workers find jobs that fit their skills, schedule, and location. The platform uses cognitive science, behavioral analysis, and peer feedback to help identify reliable hourly workers. WorkWhile was founded in 2017 by Amol Jain and Jarah Euston and is based in San Francisco, California.

point.me

Seed Round in 2022
point.me is the maker of an online search tool that makes it easy to discover real-time reward flight options.With point.me, you can not only compare all your points and miles options in the same simple format you’re used to seeing for paid flights, you can also see step-by-step guides and videos on exactly how to choose the best deal, transfer your points, and book your reward flight across dozens of frequent flyer programs.

Glue

Series A in 2022
Mystery creates a curated multi-destination night out based on the likes, dislikes, and interests of the user. They handle all services including planning, transportation, and reservations and have it a personalized experience that is a surprise.

Radian

Seed Round in 2022
Radian Aerospace is innovating the aerospace sector with its next-generation spaceplane, which is the first fully reusable vehicle designed for horizontal takeoff and landing. This single-stage to orbit spacecraft aims to facilitate the transportation of people and light cargo to low Earth orbit as well as various terrestrial locations, operating in a manner similar to conventional aircraft. Radian's vehicles are constructed from advanced materials that can endure extreme conditions and are equipped with propulsion technologies that enhance maneuverability and overall performance. Additionally, they incorporate satellite systems that improve communication capabilities, thereby supporting enhanced missions and operational efficiency within the space industry.

Frenter

Pre Seed Round in 2021
Online rental marketplace providing owners with all the tools they need to rent out items around their home and allows renters to rent out items in their city.

Spiffy

Venture Round in 2021
Spiffy, Inc. is a mobile service provider based in Durham, North Carolina, specializing in on-demand car washing, detailing, and oil change services. Founded in 2014, the company utilizes a smartphone application and website to allow customers to schedule appointments quickly and conveniently. Spiffy’s services are eco-friendly, employing methods that recycle water and eliminate runoff. The application facilitates seamless communication and payment, enhancing the overall customer experience. By offering a range of vehicle maintenance options, Spiffy aims to support vehicle owners in managing their automobiles efficiently, whether for individual use or fleet management.

Rares

Seed Round in 2021
Rares allows you to invest in the sneaker culture. We do this through fractional ownership of rare sneakers. Say goodbye to waiting in long lines for hype drops, or fighting bots online to get your hands on those desirable shoes you can flip for a profit. Rares makes it easy. You buy shares in the shoe instead of buying the shoe. Here is how it works: LEARN: You may already be savvy about sneaker culture and shoes, which is awesome. However, we feature shoes on our platform that have specific attributes and stories that make them valuable. We will educate you on these stories through our videos and other tools, so you can truly understand the value of what you are investing in. Investing not your thing? Don't worry we got you! We explain all the necessary investing terms so you only have to focus on your knowledge of shoe culture to make a smart investment. BUY: We release our shoes on our app through Initial Public Offerings (IPO). That means we make fractional shares of the shoe available for the first time for you to buy. You can buy this and hold it until we sell the shoe and cash in on the potential profits, or you can trade them with other users on our app after the IPO closes. TRADE: Once the IPO closes, you can always sell your shares to other buyers who missed out on the initial drop! No need to hold on to your shares forever! What is even better is that the shares may be worth more after the drop and you can choose to take your profits. You could also hold on to the shares until we decide to sell the shoe and then you potentially profit off the increase in price. Missed out on the drop, you can also buy shares from someone looking to sell theirs. Either way, it is up to you. Our platform makes it easier than ever to match buyers and sellers. ENGAGE: Whether you are actively trading or not, we welcome you to come on our platform to engage in a community of like-minded users. You can follow other investors, like comment, and react to relevant posts around sneakers. We think it is important to not feel like you are the only one in the room on a trading platform and we know sneakers and community go hand in hand. So please hang out and stay a while! So what are you waiting for? Stop watching from the sidelines! Invest in the culture! DISCLAIMER: This is not an offer, solicitation of an offer, or advice to buy or sell securities, or open a brokerage account on the Rares Platform. The Rares platform, 370 Legacy, inc and 370 Legacy Markets, does not recommend any securities. All investments involve risk and the past performance of a security or financial product does not guarantee future results or returns. Keep in mind that while diversification may help spread risk, it does not assure a profit, or protect against loss, in a down market. There is always the potential of losing money when you invest in securities or other financial products. Investors should consider their investment objectives and risks carefully before investing.

OneRail

Series A in 2021
OneRail is a final mile delivery orchestration platform designed to enhance the efficiency of same-day and on-demand deliveries for enterprise clients. By utilizing a cloud-based system, OneRail connects demand signals from various sources, such as point-of-sale systems, eCommerce platforms, and enterprise resource planning tools, to a network of delivery services and internal fleets in real-time. This integration provides clients with real-time visibility and actionable data, allowing for data-driven optimization of the delivery process. With a centralized view of disparate final mile data, OneRail improves the dependability, speed, and cost-effectiveness of fulfillment, making it a valuable solution for businesses seeking to streamline their delivery operations.

MealMe

Seed Round in 2021
Developer of a food delivery platform designed to find the various food options available through social media. The company's platform uses artificial intelligence to show various restaurants with recommendations based on preference, and at the same time, the delivery time of the different providers can be compared along with booking and reservation features, enabling users to save money and follow other foodies and restaurants.

RoadSync

Series B in 2021
RoadSync, Inc. designs and develops an online payment platform for various industries. It offers a payment portal that allows users to provide instant receipts to carriers, brokers, and drivers. The company’s platform also enables users to view all billing activities and recurring transaction emails. It serves warehouses, repair and tow services, drivers, and logistics industries. RoadSync, Inc. was formerly known as MyLumper Corp. and changed its name to RoadSync, Inc. in December 2017. The company was founded in 2015 and is based in Atlanta, Georgia.

Cabana

Series A in 2021
Cabana opens up the flexibility of travel plans so that travelers can book once and go anywhere. The company has built out a fleet of upscale custom-made mobile hotel rooms, using 2019 Ford Transit vans, to give travelers the freedom to travel and sleep where they want and when they want. Every element, from the bed to the storage, to the bathroom to the internet, is designed from the ground up for a tailored and premium experience. Simplified lodging often translates to lower quality, but Cabana has taken the luxurious amenities of a thoughtfully designed suite and outfitted it for a small space. Enabled through tech, Cabana brings travelers digital convenience and peace of mind through contact-free check-in. The app lets travelers reserve, check-in, pick-up, and check-out of their mobile hotel room without having to make a pit stop to the front desk.

Brightline

Series B in 2021
Brightline is a technology-enabled behavioral health home for children and their families. Brightline delivers integrated care through innovative technology, virtual behavioral health services, and a collaborative care team focused on supporting children across developmental stages and their families.

Shappi

Seed Round in 2021
Connecting Shoppers with verified Travelers to deliver products by renting the traveler’s unused luggage space.

Upaway

Pre Seed Round in 2021
Developer of a travel agency app designed to provide travel-based support. The company's platform combines travel organization tools with on-demand trip support to help find the right hotel, make the trip more eco-friendly and assist with lost luggage or a flight delay, enabling customers with a hassle-free experience regarding all their bookings.

CareRev

Series A in 2021
CareRev operates a healthcare staffing marketplace that connects healthcare facilities with flexible clinical professionals. It provides an online platform that allows hospitals and outpatient facilities to directly access per diem medical staff without the involvement of vendors or agencies. This model enables healthcare facilities to fill empty shifts more rapidly, reduce overall staffing costs, and enhance the quality of patient care by maintaining safe nurse-to-patient ratios. CareRev's platform facilitates direct communication between facilities and healthcare professionals, giving the latter the freedom to choose their working hours and locations. The company is backed by Y Combinator and a group of notable business angels, focusing on addressing the significant staffing challenges within the healthcare sector.

RippleMatch

Venture Round in 2021
RippleMatch Inc. is an online recruiting service founded in 2015 and based in New York, New York. The company aims to assist entry-level candidates in finding suitable job opportunities by automating early career recruiting and career coaching. By leveraging artificial intelligence, RippleMatch streamlines the job search process, allowing candidates to connect with employers more effectively while removing geographic barriers. The platform is designed to enhance the candidate experience and ensure that companies are matched with high-potential candidates, particularly from diverse backgrounds. RippleMatch has gained traction on college campuses and has attracted significant venture funding, enabling it to collaborate with a range of prominent companies across the country. Through its innovative approach, RippleMatch addresses the challenges faced by students and recent graduates in navigating the job market.

RippleMatch

Venture Round in 2021
RippleMatch Inc. is an online recruiting service founded in 2015 and based in New York, New York. The company aims to assist entry-level candidates in finding suitable job opportunities by automating early career recruiting and career coaching. By leveraging artificial intelligence, RippleMatch streamlines the job search process, allowing candidates to connect with employers more effectively while removing geographic barriers. The platform is designed to enhance the candidate experience and ensure that companies are matched with high-potential candidates, particularly from diverse backgrounds. RippleMatch has gained traction on college campuses and has attracted significant venture funding, enabling it to collaborate with a range of prominent companies across the country. Through its innovative approach, RippleMatch addresses the challenges faced by students and recent graduates in navigating the job market.

Phood

Funding Round in 2021
Phood’s payment API allows any existing delivery app to service college students no matter where they are. Phood opens the door for the student card to be used as a payment method on apps like Uber, Instacart, DoorDash, and Postmates.

Unagi, Inc.

Series A in 2021
Unagi, Inc. is a manufacturer based in Oakland, California, specializing in the design, production, and sale of electric scooters. Founded in 2018, the company aims to provide an eco-friendly transportation solution that addresses the challenges of urban commuting, including costs, inconveniences, and carbon emissions. Unagi's electric scooters are engineered for high performance, capable of traveling long distances on a single charge, handling hilly terrain, and ensuring a smooth ride over various road surfaces. The company sells its scooters through dealers and online platforms, focusing on enhancing mobility and offering a convenient alternative for urban dwellers.

Workchew

Seed Round in 2021
WorkChew Inc. operates a marketplace platform that connects mobile and remote workers with workspace options in restaurants and hotels across Chicago, Virginia, and Washington, D.C. Founded in 2018 and headquartered in Washington, D.C., the platform transforms dynamic restaurants into safe and affordable co-working spaces, offering food, drinks, and essential amenities such as high-speed wifi. By providing discounted dining options along with workspace access, WorkChew enables professionals to work efficiently while saving on both workspace and food expenses.

MealMe

Pre Seed Round in 2021
Developer of a food delivery platform designed to find the various food options available through social media. The company's platform uses artificial intelligence to show various restaurants with recommendations based on preference, and at the same time, the delivery time of the different providers can be compared along with booking and reservation features, enabling users to save money and follow other foodies and restaurants.

Revry

Seed Round in 2021
Revry, Inc. operates a digital media network that streams a diverse array of entertainment content specifically created for queer and allied audiences. Founded in 2016 and based in Glendale, California, the platform offers films, television series, podcasts, music albums, and original productions, all accessible via web and mobile devices. Revry highlights the best of queer culture and voices globally and is available in over 250 million homes and devices through various OTT, mobile, and online platforms, including Samsung TV Plus, The Roku Channel, and Comcast Xfinity X1. The company is led by a diverse founding team with extensive experience in technology, digital media, and LGBTQ+ advocacy, reflecting its commitment to representing queer perspectives in entertainment.

Sēkr

Seed Round in 2021
Sēkr develops an app called The Vanlife App, which helps every road traveler find their way to free camping, resources, and outdoor community. The Vanlife App guides travelers to their next best adventure with the its social features that allow them to find and connect with other travelers nearby and detailed user reviews.

Shiprocket

Series C in 2020
Shiprocket is a logistics aggregation platform designed to facilitate global and domestic shipping for micro, small, and medium enterprises (MSMEs) in the e-commerce sector. Launched in 2017, the platform serves around 1.5 lakh sellers, enabling shipping to approximately 220 countries and 26,000 PIN codes in India through partnerships with 18 courier services. Shiprocket stands out for its AI-driven recommendation engine, which helps businesses select appropriate courier services, and its cost-effective shipping rates. The platform provides a user-friendly integrated ecosystem, including tools like Shiprocket 360 and Shiprocket Social, enabling sellers to manage their shipping and returns efficiently from a single interface. With a remarkable year-over-year growth rate of 300%, Shiprocket has established itself as a key player in the logistics landscape for e-commerce in India.

Caribou

Series A in 2020
MotoRefi, Inc. operates an automotive refinance platform designed to help customers save on their car loans. By partnering with various local and community lenders, the company offers competitive loan rates and aims to reduce monthly payments, with customers typically saving an average of $100 each month. MotoRefi's secure digital platform allows users to assess potential savings and complete the refinancing process easily from home. The company handles all aspects of the transaction, including paying off the previous lender and retitling the vehicle, eliminating the need for customers to visit the DMV. Founded in 2016, MotoRefi is headquartered in Arlington, Virginia.

HopSkipDrive

Venture Round in 2020
HopSkipDrive, Inc. offers ridesharing services specifically designed for children aged five and older. Founded in 2014 and headquartered in Los Angeles, California, the company aims to provide safe and reliable transportation solutions for schools, districts, government agencies, and families. By focusing on the unique needs of children, HopSkipDrive facilitates transportation for various activities, helping to accommodate busy schedules and enhance accessibility for families in the Los Angeles area.

Bungalow

Series B in 2019
Bungalow is a residential real estate platform that offers flexible communal living solutions for early career professionals. Founded in 2016 and based in San Francisco, the company transforms unused spaces into rentable rooms by signing long-term leases with homeowners. Bungalow provides fully furnished multi-bedroom homes in desirable neighborhoods across major U.S. cities, including Baltimore, New York City, and Los Angeles. Each home features private bedrooms, shared living spaces, and amenities such as Wi-Fi, utilities, and housekeeping services. In addition, Bungalow facilitates roommate matching to create harmonious living arrangements and organizes monthly community events to foster social connections among residents. The company aims to enhance the rental experience by providing high-quality homes and a supportive community for its members.

EquipmentShare

Series B in 2019
EquipmentShare provides online construction equipment rental services, catering primarily to contractors. The company offers a wide range of equipment, including aerial work platforms, power tools, vehicles and trailers, and various specialized machinery for agriculture, landscaping, and construction tasks. Founded in 2014 and based in Columbia, Missouri, EquipmentShare has expanded its presence with additional locations in the United States and New Zealand. The company also develops proprietary technology to enhance productivity in the commercial construction sector, providing tools for fleet management that include insurance verification, background checks, and payment processing. This technology enables contractors to make informed decisions about equipment and fleet management, promoting a more connected and efficient job site.

SpotHero

Series D in 2019
SpotHero Inc. provides a digital platform for reserving off-street parking in North America, aiming to alleviate urban congestion by streamlining the parking process. Founded in 2011 and headquartered in Chicago, Illinois, with an additional office in Detroit and operations in Toronto, the company offers a mobile application and website that enable drivers to locate, compare, and book discounted parking spots. Users can easily access information about nearby parking facilities, facilitating a more efficient parking experience and reducing the time spent searching for parking. SpotHero also collaborates with mobility companies to integrate parking solutions into their services, enhancing overall convenience for users.

RoundTrip

Series A in 2019
RoundTrip, Inc. operates a digital marketplace that facilitates non-emergency medical transportation by connecting patients with a network of ride providers. Founded in 2014 and based in Philadelphia, Pennsylvania, the company offers a user-friendly software platform that allows healthcare organizations and transportation companies to schedule, dispatch, and monitor patient rides. RoundTrip serves hospitals and health plans in ten states, aiming to improve care coordination and reduce patient no-shows. The platform provides access to various transportation options, including medical cars, wheelchair vans, and stretcher vehicles. RoundTrip has established strategic partnerships with notable healthcare organizations, enhancing its service offerings. The team behind RoundTrip consists of professionals with experience as paramedics and in healthcare management, which informs their approach to addressing the challenges in medical transportation.

Hyr

Funding Round in 2018
Hyr Inc. is a mobile platform that links businesses, such as restaurants, hotels, and retailers, with independent workers to fulfill hourly shift work on demand. Established in 2015 and based in New York, the company facilitates a flexible working environment where individuals can select their own hours and quickly accept available shifts. This service caters to a younger workforce that prioritizes time and experiences over traditional employment models. Hyr also recognizes the need for benefits among gig workers and offers a portable benefits system tailored to independent contractors, enhancing their overall work experience.

Freebird

Series A in 2018
Freebird is a first-of-its-kind mobile rebooking tool that empowers travelers to skip the line and instantly book a new ticket – on any airline at no additional cost – in the event of a flight cancellation, four-hour delay, or missed connection. Freebird provides travelers with instant notifications in the event of a flight disruption, and offers the ability to rebook in less than 30 seconds with only three taps on their mobile device.

Freebird

Series A in 2018
Freebird is a first-of-its-kind mobile rebooking tool that empowers travelers to skip the line and instantly book a new ticket – on any airline at no additional cost – in the event of a flight cancellation, four-hour delay, or missed connection. Freebird provides travelers with instant notifications in the event of a flight disruption, and offers the ability to rebook in less than 30 seconds with only three taps on their mobile device.

EquipmentShare

Venture Round in 2018
EquipmentShare provides online construction equipment rental services, catering primarily to contractors. The company offers a wide range of equipment, including aerial work platforms, power tools, vehicles and trailers, and various specialized machinery for agriculture, landscaping, and construction tasks. Founded in 2014 and based in Columbia, Missouri, EquipmentShare has expanded its presence with additional locations in the United States and New Zealand. The company also develops proprietary technology to enhance productivity in the commercial construction sector, providing tools for fleet management that include insurance verification, background checks, and payment processing. This technology enables contractors to make informed decisions about equipment and fleet management, promoting a more connected and efficient job site.

Hyr

Seed Round in 2018
Hyr Inc. is a mobile platform that links businesses, such as restaurants, hotels, and retailers, with independent workers to fulfill hourly shift work on demand. Established in 2015 and based in New York, the company facilitates a flexible working environment where individuals can select their own hours and quickly accept available shifts. This service caters to a younger workforce that prioritizes time and experiences over traditional employment models. Hyr also recognizes the need for benefits among gig workers and offers a portable benefits system tailored to independent contractors, enhancing their overall work experience.

Hyr

Seed Round in 2016
Hyr Inc. is a mobile platform that links businesses, such as restaurants, hotels, and retailers, with independent workers to fulfill hourly shift work on demand. Established in 2015 and based in New York, the company facilitates a flexible working environment where individuals can select their own hours and quickly accept available shifts. This service caters to a younger workforce that prioritizes time and experiences over traditional employment models. Hyr also recognizes the need for benefits among gig workers and offers a portable benefits system tailored to independent contractors, enhancing their overall work experience.

Glamsquad

Series B in 2015
GLAMSQUAD, Inc., operating as GLAM Group, is a New York-based company that provides on-demand beauty services. Founded in 2013, it offers hair, makeup, and nail services in various cities including New York City, Los Angeles, Miami, Washington D.C., Boston, and the San Francisco Bay Area. GLAMSQUAD employs trained and vetted beauty professionals who deliver personalized services in clients' homes, at events, or in offices. The company utilizes a mobile app and website to facilitate easy booking, allowing clients to select services, dates, and locations. In addition to its service offerings, GLAMSQUAD has expanded into retail with a line of hair and makeup products, developed in response to customer feedback. The integration of technology helps match professionals with clients, ensuring a tailored experience.
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