TJ Mahony
CEO & CO-FOUNDER @ FlipKey
Boston, United States
TJ Mahony is a seed investor at FlipKey in Boston focused on E-Commerce and Software. TJ was renting his vacation home in 2007 and decided to list his Boston condo on VRB-something dot com. After several months wrestling with the site and constantly having "trust" conversations with guests he thought to himself, "this experience could be so much better - someone needs to build a useable and trusted vacation rentalsite"….. and FlipKey was born.As a strategy consultant for Accenture, ZEFER and Compete, TJ provided analysis and recommendations to Fortune 500 companies and start-ups alike, developing a solid spider sense of all things internet. TJ's biggest accomplishment was creating Compete.com, which is now the most cited online audience measurement service in the United States. He can't code. He refuses to use a Mac and his finance skills are barely adequate, but he knows a megaton about the vacation rental industry and is often featured as an industry keynote speaker, quoted in WSJ, New York Times, etc. and is an active member of several industry organizations.Top 5 FlipKey Rentals TJ's Stayed At: Antigua, St. Andrews, Scotland, Pawley's Island, South Carolina, Breckenridge, Colorado and Buenos Aires, Argentina.
- Total investments:
- 24
- Last investment:
- Lead investor:
- 29%
Last updated:
For AI agents: llms.txt
Industries TJ Mahony invests in
Stages TJ Mahony invests in
Countries TJ Mahony invests in
Round sizes
Round size
- Seed
- $1.1M–$4.5M
- Series A
- $3.1M–$30M
Investment Focus
Industry
- E-Commerce 7 (29%)
- Software 4 (17%)
- Analytics 4 (17%)
- Advertising 3 (13%)
- Financial Services 3 (13%)
Stage
- Seed 14 (58%)
- Series A 6 (25%)
- Funding Round 1 (4%)
Country
- United States 14 (58%)
- India 1 (4%)
Investments
| Company | Description | Round | Links |
|---|---|---|---|
Drivepoint
|
Drivepoint (formerly Bainbridge) is the strategic finance platform for scaling consumer brands. | $7M / Series A / Aug 13, 2025 | |
Two Boxes
|
The future of sustainable e-commerce returns. | $5.3M / Series A / Sep 16, 2024 | |
|
Two Boxes
|
The future of sustainable e-commerce returns. | $4.5M / Seed / Mar 28, 2023 | |
Bainbridge Growth
|
Bainbridge Growth helps eCommerce founders achieve the outcomes they desire. They help DTC eComm brands including peloton, warby parker, casper, and glossier. They also provide data and financial solutions for eCommerce. | $4M / Seed / Aug 31, 2022 | |
|
Drivepoint
|
Drivepoint (formerly Bainbridge) is the strategic finance platform for scaling consumer brands. | $4M / Seed / Aug 31, 2022 | |
Gordian Software
|
Gordian Software builds APIs that enable the world's leading travel organizations to increase revenue. Gordian’s customers include Priceline, Hopper, Trip.com, and many more leading global travel agencies and management companies. Gordian supports over 100 airlines including partnerships with Lufthansa Group, United Airlines, and SingaporeAirlines. Gordian has grown rapidly, including 3.5x revenue growth in H1 2022 and serves more than 60 million passengers per month. Launched in 2017, Gordian is backed by Y Combinator, Accomplice, Vinyl, Kinnevik, DST Global Partners, Latitude, and Naval Ravikant.Gordian’s growth is powered by its core values of Freedom, Impact, and Ownership. From 3 day sprints to our remote-friendly 7+1 onsites, each of our 30+ teammates are empowered to do their best work. Gordian is headquartered in Bellevue, WA.For more information, visit gordiansoftware.com | $25M / Series A / Jul 19, 2022 | |
Xeno
|
Brands use Xeno to send 1 to 1 campaigns to their existing customers. For example, we help a brand with 3 million existing customers send 3 million unique campaigns. | $1.6M / Seed / Mar 14, 2022 | |
Flume Health
|
Flume Health makes self-insured health plans affordable and easy to use. They do this by combining the incredible best customer support that they would never expect from their health plan administrator, along with a new payments technology that allows its members to see the same providers for 20-40% less than traditional network rates.The companywas founded in 2018 and is headquartered in New York. | $30M / Series A / Mar 04, 2022 | |
Peel
|
Peel is a SaaS product automating analysis and reporting of the most popular metrics for consumer businesses. | $5.3M / Seed / Sep 30, 2021 | |
Givz
|
Givz is the leading purpose-driven marketing technology designed to optimize growth, promote meaningful engagement, and drive repeat (profitable) customer action.Having built the first frictionless donor-focused platform that allows anyone to donate to any of the 1.6M+ U.S. charities in 15 seconds or less, we now work with brands to earn,strengthen, and protect consumer-brand relationships in a way that serves all stakeholders; the brands, their customers, and the community at large.Its Shop-to-Givz model enables brands to serve customers with revenue-generating, high-converting incentives that leverage the power of emotional connection to drive quantifiable growth. This MarTech innovation puts individual purpose behind each customer’s purchase while driving success as defined by the brand’s respective goals.Givz was founded in 2017 and based in New York, New York. | $3M / Seed / Aug 23, 2021 | |
| See all 24 investments → | |||
Co-Investors
About FlipKey
FlipKey is a community driven travel site that helps consumers find trusted vacation rental homes throughout the world, by providing real reviews of verified vacation rental properties. FlipKey organizes the reputation of vacation rental properties throughout the world, by verifying that homes are represented by legitimate managers/ownersand then collecting detailed reviews from real guests. FlipKey employs the industry's only closed review system that limits reviews to confirmed past guests. FlipKey's Reputation Management tools then allow for vacation rental managers to post public responses to both positive and negative reviews to facilitate a constructive dialog concerning the quality of individual properties and services provided. Vacationers can use FlipKey.com to evaluate over 50,000 verified vacation rental properties and then book their accommodations directly online or call/email the manager for more information.
FlipKey Contacts
| Name | Phone | Socials | |
|---|---|---|---|
Beth Giudicessi
Marketing Manager
|
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Mehmet Ali Elicin
Sr. Product Manager
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TJ Mahony
CEO & CO-FOUNDER
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2 more contacts available
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FAQ
What does TJ Mahony invest in?
TJ Mahony invests primarily in E-Commerce, Software and Analytics startups, most often at Seed and Series A stage. Most of the 24 investments tracked by Shizune back companies in United States. The Investment Focus section breaks down every industry, stage and country in the portfolio.
What is TJ Mahony's check size?
TJ Mahony typically joins rounds of $1.1M–$4.5M at Seed and $3.1M–$30M at Series A. These ranges are 10th–90th percentile round sizes calculated from confirmed public funding rounds, so they are a realistic guide to the rounds TJ Mahony participates in.
When did TJ Mahony last invest?
The most recent investment recorded for TJ Mahony closed in Aug 2025. Shizune tracks 24 investments in total for this profile, including round sizes, stages and portfolio companies, all sourced from confirmed public funding rounds and refreshed monthly.
Is Shizune's investor data accurate?
Yes — every stat on this profile is calculated from confirmed public funding rounds monitored across hundreds of sources since 2020. This profile was last refreshed in Aug 2026 and is updated monthly. Spotted something off? Use the “Suggest an edit” link near the top of the page.
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