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Headout has raised $54.0M across 4 funding rounds.
Key people at Headout.
Headout has raised $54.0M in total across 4 funding rounds.
Headout, based in New York, NY, operates a mobile-first managed marketplace for curated travel experiences, tours, activities, and events, specializing in last-minute bookings. The platform connects users worldwide with real-life experiences across over 30 cities, serving 9-10 million users from 190+ countries. Headout achieved a revenue run-rate exceeding $200 million in 2021, demonstrating 8x year-over-year growth by late 2021. The company secured a total of $42 million in its Series B funding round, with Glade Brook Capital leading a $12 million tranche in September 2021, alongside investors like Nexus Venture Partners and Version One Ventures. With a team of approximately 100 employees in 2018, Headout focuses on standardizing and upgrading partner offerings to enhance the user experience. It was founded in 2014 by Varun Khona, Suren Sultania, and Vikram Jit Singh.
Key people at Headout.
# Headout: High-Level Overview
Headout is an online marketplace platform that connects travelers with curated tours, activities, events, and local experiences across global destinations.[1][5] Founded in 2015 and based in New York, the company has built a profitable business serving over 35 million guests from 196 countries across 81 destinations.[2] Headout's core mission is to bridge the gap between people and real-world experiences by making it easy, delightful, and inspiring to discover and book exceptional activities that entertain, educate, and inspire.[5]
The company operates as a full-service marketplace that standardizes a highly fragmented experiences industry by working directly with small and medium experience providers to ensure consistent quality, pricing, and service levels.[3] With $200M+ in annual sales and profitability achieved, Headout has demonstrated strong unit economics while maintaining growth momentum in the post-pandemic travel recovery.[1]
# Origin Story
Headout was founded in 2015 by Varun Khona, Suren Sultania, and Vikramjit Singh, with Khona serving as co-founder and CEO.[1] Khona's entrepreneurial background includes early work in the travel sector and a stint at Goldman Sachs, which he left to pursue startup ventures.[1] The company was formerly known as Tourlandish before rebranding to Headout.[4]
The founding team identified a critical gap in the travel experiences market: while millions of travelers sought authentic, local activities, the industry remained highly fragmented with inconsistent quality and pricing. Rather than building yet another aggregator, the founders envisioned a curated platform that would standardize experiences through direct partnerships with local operators, creating a seamless booking experience for global travelers.
# Core Differentiators
# Role in the Broader Tech Landscape
Headout operates at the intersection of several powerful trends reshaping travel and consumer experiences. The post-pandemic "revenge travel" phenomenon—a rekindling of desire to experience the world after prolonged lockdowns—has created tailwinds for the experiences economy.[6] Simultaneously, the accelerated digitization of traditionally offline industries has created opportunities for platforms that can aggregate fragmented, local supply into seamless digital marketplaces.
The company exemplifies a broader shift toward experiential consumption over material goods, particularly among younger travelers prioritizing memories and authentic connections. By standardizing and scaling what was once a purely local, offline industry, Headout demonstrates how technology can unlock value in service-based marketplaces without commoditizing the human element of travel experiences.
The company's approach—selective curation over exhaustive listing—also reflects a maturing marketplace philosophy that prioritizes user experience and decision simplicity over maximizing inventory, a lesson increasingly adopted across consumer platforms.
# Quick Take & Future Outlook
Headout has positioned itself as the category leader in curated travel experiences by solving a fundamental problem: making it easy for billions of people to discover and book authentic, high-quality activities without overwhelming choice or inconsistent quality. The company's path to profitability while maintaining growth suggests sustainable competitive advantages in brand trust, operational efficiency, and local partnerships.
Looking ahead, Headout's expansion from 81 to 500 destinations (as of its $30M funding round) represents significant runway for geographic growth.[6] The company's focus on domestic short-haul travel and new verticals suggests diversification beyond international tourism. As remote work and flexible travel patterns persist, demand for spontaneous, last-minute experiences—Headout's core strength—will likely remain elevated.
The broader question for Headout is whether its curated model can scale globally while maintaining the local expertise and quality standards that differentiate it from pure aggregators. Success will depend on building a network of trusted local partners and maintaining operational discipline as the platform expands into less mature markets. In a world increasingly defined by experiences over possessions, Headout's mission to reconnect people with the real world positions it as a meaningful player in how travel and leisure evolve over the next decade.
Headout has raised $54.0M across 4 funding rounds. Most recently, it raised $30.0M Series B in February 2022.
Headout has raised $54.0M in total across 4 funding rounds.
Headout's investors include Linda Guo, Ankit Sobti, Oliver Hudson, Ranjeet Pratap Singh, Sriharsha Majety, 500 Startups, Espresso Capital, FJ Labs, Haystack, Ludlow Ventures, Nexus Venture Partners, Practical VC.
