Bootstrapping to Unicorn: The Cost of Discipline

1. Hostaway became the first STR PMS unicorn in October 2025, reaching a $1 billion valuation after bootstrapping the company for nearly a decade before taking outside capital. Looking back, what was the hardest moment where you could have taken funding earlier but chose not to, and what did that discipline ultimately cost you?

“Great question! There were too many compromises to list them all, but I think we should have invested in ourselves as founders earlier, paying ourselves a proper salary. At some points, we were among the lowest-paid employees. When you found a company, it’s hard to justify spending money on yourself rather than your employees, but you can’t lead well if you don’t take care of yourself too.”

2. You built Hostaway as a fully remote organisation operating across 44 countries. At 325 people, remote work is no longer an experiment, it’s the operating model. What has been the hardest thing to scale in that structure?

“Scaling as a remote company has been the best decision we’ve made from a company culture perspective. We’re able to get the best talent in the right markets, and our staff is happy working from wherever they want. The biggest challenge was communication, but it’s a challenge we were happy to take on. With teams in different time zones and taking informal in-person conversations out of the equation, we had to create intentional forums for teams to work together. By combining structured communication, organized workflows and productive in-person time, our teams work better together than they ever did in person.”

3. Hostaway has invested heavily in AI over the past year, launching tools across messaging, pricing, and workflow automation. With $365M raised and unicorn status to defend, how do you decide which AI features are genuinely worth building versus which ones risk adding complexity without adding value for property managers?

“The best way to build tools your customers genuinely need is to ask them. We’re always in communication with our Hostaway users. Our customer success team constantly provides feedback to our product team about where our customers are really seeing value and what would help them improve. The same is true for Hostaway’s AI tools. We don’t assume what property managers want, we actively ask them and only build the tools that really make sense.

“When we first started Hostaway, Saber and I became property managers ourselves to truly live the experience. We were in the trenches, sometimes even scrubbing toilets when cleaning services didn’t show up. There’s really no other way to fully understand what property managers face every day. That’s the customer-obsessed mentality we’ve carried through to Hostaway.

“Hostaway is at a great advantage in the AI race because we have more data than our competitors. More data means better-trained AI, custom-built with industry expertise and deep insights for property managers’ businesses.”

4. You started your first company at 11. What is the one thing you understand about building a business today that you wish you had known at the very beginning of Hostaway?

“I’ve thought about this a lot, but honestly, I don’t think I would have liked to have learnt anything earlier on. For example, had I known how hard it was going to be, and how personal it gets, or how many sacrifices I’d have to make, I think I would have given up a lot earlier, and never gotten to where we are today.

“There is only one thing I regret. As we were starting Hostaway, my wife recommended that I read The Hard Thing About Hard Things. It actually took me 6 years to pick up the book – and I wish I had done it earlier. It was a massive relief was taken off my shoulders, I actually got tears in my eyes as I read that book, as I realized I wasn’t alone. It was an invaluable lesson.”