028: $200M Raised, 50x Growth: Johannes Siebers of Holidu on Local Trust, Agentic Workflows and the Supply Nobody Else Was Counting
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How did Holidu achieve 50× growth between 2020‑2025?
We scaled a lot, uh fifty times from
twenty twenty to twenty twenty-five. How did you actually make that work, building a business together as brothers? We had to put all the
expansion to a stall. While outside of Holy Doo everything was growing through the roof in terms of software and valuations and and and other companies
hiring like crazy and we couldn't do so. But that's In a way, not sexy at all. One thing that you wanna see. is that you bring supply that has never been rented before. And if we crack that then we have a huge market in front of us. Seeing at all these closed windows just hurts my STR heart all the time. You can use technology in all the aspects of this journey.
But I think still th this initial moment is
crucial. You are listening to STR Global Unlocked, brought to you by AJL Atelier, the show where I speak with the leaders shaping short-term rentals worldwide. I am Simon Lehman and after two decades buying, selling, advising and investing, I've built a network that spans continents and categories. This podcast brings that network to you guys. Real conversations, global insight, no PR fluff. Let's get started. OTS shares drop nearly twenty percent. Three hundred billion dollars in SaaS market cap evaporates. AI is beginning to reshape how guests discover, compare book travel. In the middle of this volatility, European marketplace companies like Holy Doo continue to scale. So the question is not whether the market is changing.
The question is who will control distribution in the next decade? Today I'm joined by Johannes Sievers, co-founder and CEO of Holydew. Holydew has grown into one of Europe's most significant vacation rental marketplaces, raising substantial capital, expanding internationally, and navigating multiple market cycles from hypergrowth to capital discipline. Йоанс, і це грай пляжі то війну шоу.
Hi Simon. Thanks a lot for having me.
Absolutely great. Uh we get so many occasion to speak together. Um but one thing we can say you're the first as an individual is that you're a torchbearer uh from the Olympic Games, and that's the first one that has ever attended STR Global unlocked. When I saw your post on LinkedIn, I was like, Oh my god, uh Johannes Siebers is carrying the Olympic torch for Milan um Cortina and And we've just figured out that Germany won two medals more than Switzerland, so we'll leave that aside of the conversation. But I would love to learn more. How do you get to carrying the Olympic torch? That's pretty significant.
Thanks a lot for bring for bringing it up. It was a beautiful experience, I have to say. It was a great honor. Um I got lucky. I got introduced to the opportunity by Ibn B, who's one of our longstanding partners and also sponsor of the Olympics and Look, I I love the spirit of the Olympic competition, aiming for excellence, aiming to win, but also the respect and friendship uh between athletes there. And I think there's a lot we can take from this. So it was a real honor for me to to carry that flame and and I also have very deep respect for the athletes competing there. Um they are the best of the best in the world and in what they do and that's very tough to reach. You only get there if you d train for many many years, if you really discipline, if you take sacrifice, take the needle investment.
You work with amazing teams, so also there there's a lot to learn from them and uh I think there's also parallels between that and anyone building something. Uh so overall it was for me a great a great moment and a and a beautiful experience and I was very thankful. for Fred.
Yeah, great analogy, especially to startups and many to our listeners as well, to think about that. It needs an enormous amount of discipline and control, and obviously an experience that will be lifelasting also for you. Um to make that happen and uh that's very significant and and we know how hard it is because you only have a chance once in four years. It's a little bit different to what we're experiencing on a daily basis.
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Chapters
8 chapters
1
How did Holidu achieve 50× growth between 2020‑2025?
0:00–6:10
2
Why does Johannes say every company must become an AI company?
6:10–12:40
3
What was the strategic pivot from a pure marketplace to a software‑plus‑service model?
12:40–18:55
4
How did COVID‑19 become a ‘gift’ that helped Holidu build stronger product discipline?
18:55–25:14
5
Why does removing friction rather than adding distribution unlock new supply?
25:14–32:24
6
How do Johannes and his brother divide responsibilities and sustain their partnership?
32:24–37:30
7
What do investors look for in 2026 versus 2016 and why is capital discipline crucial?
37:30–42:56
8
Will brand matter more than ever as AI reshapes search and discovery?
42:56–49:22
Speakers
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