In this interview clip, Varun, co‑founder of Headout, recounts how the company was launched as a marketplace for last‑minute experiences in the United States despite the founders having no prior residence, education, or network in the country. He describes the initial, intense effort to build a supply side: cold‑calling, emailing, and LinkedIn outreach to 60‑65 potential partners each day for three months, while also handling customer calls for up to 18 hours a day. The key obstacle was that small experience providers lacked technical capability to expose real‑time inventory. To solve this, Headout built a custom scraper that pulled data from Excel, Google Sheets, and local ERPs, converting it into live inventory for the platform. This “scrape‑instead‑of‑API” approach allowed immediate bookings for last‑minute slots. Varun emphasizes that solving supply‑side problems first—getting partners’ inventory online—was the decisive factor that later enabled demand growth. The takeaway is that a strong, accessible supply base drives consumer demand in a marketplace.
Chapters
You know, what were like the first steps that you took to start Headout as a marketplace, and then maybe some of the kind of initial challenges that you faced?
That's a long story. Okay, let me try and talk about the ones that were really interesting. So I think what's extremely unconventional about our story is that we decided to sort of launch Headout in the US, even though both my co-founder and I don't come from the States. We have not lived there, we've not studied there. literally, like, I came to the States for the first time after we had incorporated Headout, right? So, uh, we did something that was batshit crazy, and, and, uh, I don't recommend it to most of the people, but we just felt like there was a huge market for last-minute experiences, and it was in the West, not in India where we were, and we just felt like we had to sort of go West and try and figure it out from there. So The first sort of crazy thing that happened was going to a new country and trying to sort of launch something from scratch there, uh, sealing the supply side of the equation. How do you get suppliers? Um, we didn't have a network, etc. So I think, I think that entire process of how we got ourselves embedded into the ecosystem, uh, was a really interesting one. It was just a ton of cold calling, persistent emailing, sending notes with invites on LinkedIn. Uh, I used to sort of sit down and reach out to on an average about 60 to 65 potential supply-side partners every single day, and I did that for almost 3 months every single day of the week including weekends. And then I also sort of be the guy that was also sort of on customer calls, and that's kind of like my routine for about 18 hours a day for the first 3 months. So I think what was really interesting for us in the very beginning was that we realized that when we were chatting with these mom-and-pop shop owners who were selling experiences, um, they didn't care so much about the fact that we aren't from here or that we don't know America as a market. What they really sort of cared about is that they have a ton of unsold inventory that's lying with them, which is going, uh, you know, which is, which is going for waste. And they would love to be able to figure out a way to get as many people through the door and increase their occupancy rate. But they don't have a technical bent of mind. They don't know how to sell this well online, especially sort of real time at the last minute for today, tomorrow. And they didn't know how to do this on mobile. And so they wanted us to figure it out for them, but they just could not for the love of their life sort of figure out a way to give us live access to inventory. And so I think the, the most interesting thing that we did in the early days of Headout, which to some extent even continues to this date, is we actually wrote a custom piece of software to be able to scrape the Excel sheets and Google Sheets and whatever other local systems that these guys were using to be able to have access to their real-time inventory status so that we can then pass that information to our systems and then allow consumers to be able to see what's available and then be able to book them for the next half an hour, the next couple of hours, and so on and so forth. So I think just the sheer amount of hustle in being able to say that, listen, the primary problem statement is that they want to do this, but they just don't have the technical sophistication or the bandwidth or the money to be able to pay for a service, you know, where they have APIs that can talk to the world, um, and so on and so forth. Instead of waiting for them to, to get there, why don't we just work with the solutions that they have? They use Excel, they use Sheets, they use some local ERP, we're just going to write software that will scrape their front end, they'll scrape their screens and get that information into our systems, process them and have that available. I think was a huge move in the right direction which we kind of stumbled upon in the first few weeks of trying after having like incessant conversations with some of these guys and trying to sort of fix them. So interesting days, it was a lot of hard work but I guess we wouldn't have it any other way because it sort of really gave us a good insight into always solving for supply-side problem statements first, and that almost always leads to whatever solutions that you want on the demand side. If you have a great sort of product, if you have a great supply, then demand will come to you, but that's kind of where the meat of the action lies, and that's kind of the big takeaway that we had from the first, I would say, 9 to 12 months of Headout.
