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Startup Deep Dive : Headout — the 0M raise that came in the middle of a pandemic wave

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The Invincible India Startup Deep Dive featured graphic for Headout.

In 2024, Headout’s revenue crossed $130 million, eight times what it was making in its post-Covid trough — a real comeback for a company whose own co-founder says its bookings went from “$250 million plus to negligible scale in a matter of weeks” when the pandemic hit in March 2020. Headout is not a household name the way Viator or GetYourGuide are, yet this India-built, New York-headquartered marketplace for tours and attractions has now outlasted two separate collapses in travel demand.

What makes the story worth reading closely is not the recovery itself but how it happened: no mass layoffs, a pivot to a market (domestic travel) the company had never prioritised, and a decision to keep raising money from the same small set of backers through the worst months for travel-tech funding on record. This piece pulls together what is publicly verifiable about Headout’s founding, its financial shape, its 2020 near-death, and the risks that still sit under a business that, by its own account, only became profitable in the last few years.

Quick facts

Company Headout Inc. (US parent); Indian arm Tourlandish Online Ventures Private Limited, Bengaluru
Founded 2014 as Headout (predecessor Tourlandish founded 2013)
Founder(s) Varun Khona (CEO), with Suren Sultania (now COO) and Vikramjit Singh, who co-founded the original Tourlandish venture in 2013
Businesses Managed marketplace for tours, attractions and local experiences; AI trip-planning layer built on the 2024 Dabble acquisition
Latest FY revenue $130 million globally for calendar year 2024, roughly ₹1,248 crore converted at $1 ≈ ₹96 (company-stated, unaudited)
Latest FY profit/loss Company says it was overall profitable in CY2024 with contribution margin above 30%, and describes double-digit EBITDA margin as “in sight” rather than achieved (company-stated)
Listed Private — no IPO
Market value / last valuation Contested: CEO described it as “high hundreds of millions” of dollars in February 2022; private-market tracker Caplight estimates roughly $224.8 million, range $132.6 million to $318.1 million
Key shareholders / CEO CEO and co-founder Varun Khona; lead institutional backers Nexus Venture Partners, Glade Brook Capital and 500 Global (500 Startups)

What they do

Headout runs a booking marketplace for things to do once a traveller has already landed somewhere — skip-the-line museum tickets, city tours, day trips, theatre and live shows, and local attractions — sold through its own app and website rather than through a traditional travel agent. Its pitch to travellers is same-day and next-day booking in cities such as New York, London, Paris, Rome, Barcelona, Dubai and Las Vegas, and its pitch to the tour operators and attractions on the other side of the marketplace is distribution and demand they would otherwise have to generate themselves.

The origin

The company’s roots go back to 2013, when Varun Khona, Vikramjit Singh and Suren Sultania set up a venture called Tourlandish after getting frustrated planning a European trip that meant Googling, emailing and calling a dozen separate local operators just to book a few afternoons of sightseeing. Khona had already tried one earlier startup, and had spent time travelling on a tight budget through countries including Kenya, Egypt and Sri Lanka before that. Tourlandish itself did not take off. Rather than shutting down, the same founding team rebuilt the idea in the United States in late 2014 and relaunched it as Headout, narrowing the focus to instant, on-demand booking of tours and attractions rather than trip planning in general.

The struggle years

The first near-death is easy to miss because it happened before the company had the name it trades under today: Tourlandish, founded in 2013, did not find traction and was effectively wound down and re-founded as Headout in 2014 — a full identity change rather than a simple rebrand.

The second, much bigger one, arrived in March 2020. Khona has described Headout’s business going from more than $250 million in scale to “negligible” within weeks as international travel shut down almost overnight; bookings fell by more than 90 percent. Unlike a number of other travel-tech companies that cut headcount hard in 2020, Headout chose not to lay off staff, and instead spent the last quarter of 2020 rebuilding around domestic travel — people exploring their own city or region rather than crossing a border. That single change in focus, made under pressure with no guarantee it would work, is what the recovery was built on.

The turning point

The clearest before-and-after moment sits across late 2021 and early 2022. By September 2021, roughly 18 months after bookings had collapsed, Headout said it had reached EBITDA profitability and raised a $12 million round to hire more than 150 people as domestic travel rebounded — domestic bookings had gone from a small share of the business before the pandemic to about 80 percent of it. Two months later, the company said bookings were running at ten times where they had started the year. Then, in February 2022, in the middle of the Omicron wave when much of the travel industry was pulling back again, Headout closed a further $30 million round led by Glade Brook Capital. Going from “negligible scale” in mid-2020 to a fresh $30 million raise during a second pandemic wave, on the back of a domestic-travel pivot nobody had asked for, is the hinge the rest of the company’s growth sits on.

The money behind it

Headout has stayed with a small, repeat set of backers rather than chasing a large number of new investors each round. Reported figures on lifetime funding differ slightly by tracker — Skift and PhocusWire put it at “more than $60 million” as of May 2024, Inc42’s funding tracker lists $64.2 million, and Tracxn’s investor page lists $70.5 million — so the safest read is a lifetime total in the $60–70 million range, not a single precise figure.

Three backers stand out for what they specifically changed, not just how much they wrote:

Valuation is genuinely contested. At the time of the February 2022 round, Khona described Headout’s valuation only as being in the “high hundreds of millions” of dollars, without a number (TechCrunch, February 2022). Private-market data provider Caplight separately models Headout’s valuation at roughly $224.8 million, with a range of $132.6 million to $318.1 million. Absent a newer priced round or IPO, neither figure should be read as confirmed — this is a range, not a fact.

How it makes money

Headout is a commission marketplace, not a tour operator: it does not generally own the attractions, buses or guides it sells, it sells access to other operators’ inventory and keeps a cut.

On margin, the company says its contribution margin (CM2, meaning revenue after direct variable costs of serving a booking) rose above 30 percent in 2024, and that it is overall profitable with double-digit EBITDA margins “in sight” rather than already banked (Headout newsroom and CEO Varun Khona, February 2025). What people tend to get wrong is treating Headout’s headline growth numbers as revenue when several of the company’s own past statements were about gross booking value, the total value of tickets sold, not what Headout itself keeps — Khona made a point of clarifying in 2025 that the $130 million 2024 figure was “revenue, not GBV.”

The numbers

Headout is privately held and has not published a multi-year, audited profit-and-loss statement, so a clean three-to-four-year revenue and profit table of the kind available for a listed company or an Indian entity that files full accounts does not exist here. What follows are the dated, sourced figures that are actually available, rather than an invented series:

Period Metric Figure Source
Pre-March 2020 Business scale (bookings-linked, not confirmed as revenue) “$250 million-plus” per Khona; fell to “negligible” within weeks of Covid-19 onset TechCrunch, February 2022
September 2021 Profitability milestone Company says it reached EBITDA profitability TechCrunch, September 2021
November 2021 Booking volume growth 10x versus the start of calendar 2021 TechCrunch, February 2022
FY2023 (year to March 2023) Revenue of the Indian engineering entity, Tourlandish Online Ventures Pvt Ltd (not consolidated global revenue) ₹75–100 crore, up roughly 190% year-on-year per the filing summary Tofler company filing summary, accessed September 2026
Calendar year 2024 Consolidated global revenue $130 million (~₹1,248 crore), up 8x from the post-Covid baseline; contribution margin above 30%; company describes itself as profitable Headout newsroom and CEO Varun Khona, February 2025

Two things worth flagging rather than smoothing over: the Indian entity’s RoC-sourced revenue is for a Bengaluru-based technology/engineering subsidiary that appears to bill the US parent for services, not the group’s consolidated top line, so it should not be read against the $130 million global figure directly. And the $130 million figure itself is company-stated and unaudited, since Headout is a private company with no public exchange filings — there is no independent auditor’s report backing it up as of September 2026.

Where the money comes from

The risks

The takeaway

The lesson in Headout’s story is not “pivot to survive” in the abstract — most companies say that and few show the receipts. It is that Headout refused the two easiest responses to a demand collapse, shutting down or cutting the team to the bone, and instead spent a full quarter rebuilding around a market segment (domestic travellers) it had never prioritised, while keeping the people who could execute that rebuild. The capital that followed, including a raise made in the middle of a second pandemic wave, came after the pivot had already started working, not before. For a founder facing a demand shock, the order of operations here — protect the team, change the market you are serving, then raise on evidence — is the transferable part, more than any single number in this piece.

Frequently asked questions

What does Headout actually sell?

Headout runs an online marketplace for tours, attractions, and local experiences — things like skip-the-line museum entry, city tours, and day trips — bookable same-day or next-day through its app and website, mostly in major tourist cities such as New York, Paris, London, Rome and Dubai.

Who founded Headout and when?

Varun Khona, Vikramjit Singh and Suren Sultania founded an earlier venture called Tourlandish in 2013; when that did not take off, the same team relaunched the idea in the United States in late 2014 as Headout, with Khona as CEO and Sultania later becoming COO.

How much funding has Headout raised, and who backs it?

Public trackers put Headout’s lifetime funding at roughly $60–70 million, with lead investors including Nexus Venture Partners, Glade Brook Capital and 500 Global (500 Startups); the most recent disclosed round was a $30 million Series B extension in February 2022.

Is Headout profitable?

Headout says it was overall profitable in calendar year 2024, with contribution margin above 30 percent, and describes double-digit EBITDA margins as “in sight” rather than already achieved. These are company-stated figures; Headout is private and does not publish audited financial statements.

Is Headout listed on any stock exchange?

No. Headout is a privately held company with no public listing or disclosed IPO plans as of September 2026; its most recent valuation estimates — ranging from a company-described “high hundreds of millions” to a third-party model of roughly $224.8 million — are unconfirmed by any recent priced round.

Sources

Figures are as of September 2026. Currency converted at $1 ≈ ₹96.0 as of 18 September 2026 (Trading Economics).

Found an error? Write to us and we’ll correct it in the open, dated, on the piece.

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