Marcus Rader moved from Finland to Toronto in 2015 because his wife was offered a job there. He was not. By his own telling he sat one job interview, failed the IQ test on it because every measurement was in imperial units, and decided he would rather use what he knew about startups, including the ones that had gone badly, to start his own.

What he noticed in Toronto was Airbnb, and specifically the layer of people behind the listings. Not weekend hosts renting out a spare room, but professional property managers running dozens or hundreds of units each, stitching together bookings from Airbnb, Booking.com and everything else by hand. The software those managers needed either did not exist or was being built by people who came out of real estate rather than out of technology.

Investors were not impressed. Rader says they told him the niche was too small and he would never find enough users. His answer was a t-shirt. He printed one that read "Free Beer for Airbnb Hosts" and stood on the corner of King Street West for an hour. An hour of conversations settled it for him. "The investors were wrong, I was right, this was gonna be big," he wrote about that afternoon ten years later.

That is the origin story. The ten years in between were slower than the anniversary post makes them sound, and Rader has been unusually specific about the numbers.

In a keynote he gave at Slush in November 2025, he laid out the early curve against a 2015 start. Two years to go from three founders to six employees. Almost three and a half years to land a million dollar round from a venture fund, which lines up with his own November 2018 post announcing $1.4 million from Vendep Capital and Business Finland, at which point Hostaway was about thirty people. And four years to reach $100,000 in monthly recurring revenue, roughly $1.2 million annualized. That four year mark, counted from the 2015 start he states in the same talk, is the milestone recorded here. His own comment on it: today you see companies do $100,000 MRR in two days, but it was not like that back then.

The first money in was not from any of those funds. On the night the three of them decided to found the company, the third co-founder put in 50,000 so the others could pay themselves a basic salary and buy food. A friends and family round followed, then venture capital, then private equity. Rader says it took him seven years to work out that by the definition private equity firms use, a company that reaches $10 million in ARR on less than two or three million of investment still counts as bootstrapped.

The go to market was cheap and unglamorous. Rader wrote the first ad himself, put it on Facebook, targeted people interested in Airbnb, and ran the line "Free Airbnb management software". Free was easy to promise because there were no customers to lose. There was also no product. Hundreds of people signed up anyway, and he called every one of them. When somebody got annoyed at being called by a company with nothing to sell, he apologised and kept the conversation going. Ten percent of them wanted something simple, so the team built that, and it turned out people wanted it but would not pay for it. So he asked what it would take. They named a feature, the team built the feature, and eventually one of them said enough with the feedback already, I want to pay you.

Two other decisions from that period matter. The founders ran a couple of vacation rentals themselves, deliberately at a distance, with Rader managing a property in Finland from Toronto while his co-founder managed a Toronto property from Finland, just to feel the problem from the customer's side. And they described the product as Airbnb management software rather than inventing a category name, because that was the phrase property managers were already typing into Google.

Then it nearly ended. Hostaway spent the second half of 2019 building a proper sales and marketing engine, and in January 2020 the executive team decided to go all in and hire hard behind it. That lasted about a month. When covid hit, revenue fell roughly forty percent, the new sales and marketing hires were let go along with about a third of the staff, and the company was short of cash again, which Rader points out was not new since they had been running out of money for five years by then.

What followed was eighteen months of not knowing. Every month the team added around $10,000 in new monthly revenue and every month covid took about $10,000 back out. It felt like treading water. The answer arrived at a trade show in September 2021, where Rader worked out that very few people in the world were buying vacation rental software at that moment, but Hostaway was winning nearly all of them, while competitors were winning none. The same month, Airbnb named Hostaway a preferred software partner.

After that the numbers move fast: $1 million ARR, $3 million, $10 million, $30 million. A private equity firm came to them rather than the other way round, which turned into a $175 million investment from PSG in May 2023. About eighteen months later came a $365 million round at a $925 million valuation, and in October 2025, ten years after the street corner, a $1 billion valuation and the first unicorn in short term rental software. Three hundred people, fully remote, in more than fifty countries.