Over the last few years, I’ve had countless conversations with short-term rental founders.
Different markets.
Different company sizes.
Different business models.
But at some point, the same sentence keeps coming up:
“We’ve grown, but I’m still involved in everything.”
Every hiring decision.
Every operational fire.
Every guest issue that escalates.
Every new idea that somehow still needs the founder to push it forward.
And that is usually the moment when growth stops feeling like freedom and starts feeling like a more complex version of the same job.
That is why I started a new WhatsApp channel called From Operator to CEO.
It is for STR founders who are trying to make one of the hardest transitions in business:
moving out of the day-to-day and into the CEO seat.
This is not another place for industry noise, motivational quotes, or abstract leadership theory.
Every post will be one usable thing:
a system,
a decision framework,
a question worth asking,
or a mindset shift drawn from 20 years inside STR.
The kind of thinking that helps you build a company that no longer depends on you for every decision.
Because at a certain stage, the real bottleneck is no longer demand, distribution, or even operations.
Very often, it is the founder’s role inside the company.
So this is where I’ll share the thinking between episodes and emails - more direct, more often, and focused on what actually moves the needle when you are scaling an STR business.
Best,
Simon