Simon Lehmann has spent 21 years in this industry, running one of the largest vacation rental companies in Europe, co-founding Vacasa Europe, sitting on the boards of HomeAway and Breezeway, and now advising more than 50 property management companies across 20 countries. Over the past decade he has been mapping how those companies are structured, and he has identified five levels every property management business moves through, along with one transition where more than 80% of them get stuck.

I invited Simon on this podcast because his video, The Five Levels of STR Companies Explained, made me wince. He describes, almost line by line, the way I ran CottageLink Rental Management for the best part of 15 years: every contract in my head, every standard different, every decision routed through me. I got right up to that wall at 200 properties and never went through it. I sold instead.

This conversation is honest about what that costs, and specific about what has to change before you can climb. Whether you are at five properties or 150, you are somewhere on this ladder.

About the guest

Simon Lehmann is one of the most recognized figures in professional short-term rental. He was CEO of Interhome, co-founder and chairman of Vacasa Europe, chairman of MadeComfy in Australia, and a board member at HomeAway and Breezeway. Through AJL Atelier he advises property management companies worldwide, with most of his one-to-one work in the 50 to 200 unit bracket. He hosts the STR Global Unlocked podcast and is launching the Simon Lehmann Academy, a self-serve curriculum built from 21 years of domain knowledge. Some people in this industry call him the Godfather.

Key takeaways

• Below 50 units you are the system. Every standard, every owner agreement, and every exception lives in your head, and that is exactly what stops you growing past it.
• The first real hire is not a junior assistant or a VA. It is an operations person who can take 50% of the work off your hands so you can start being strategic.
• Saying yes to every property will cost you later. When operators finally analyze owner lifetime value and margin contribution per property, they typically find 20 to 25% of the portfolio is dragging the whole business down.
• Tier your owners internally, into three tiers, no later than 100 units. This is an internal exercise, not an owner-facing one, and it is the first step toward a single standard contract.
• The number worth building your reporting around is net margin contribution per unit. Most managers know how profitable the business is. Very few can tell you how profitable one property is.
• You have to fire yourself from the position that creates the biggest bottleneck in your company. Selling while you are still the operator means the buyer discounts the price by the cost of replacing you.
• Simon replaced 4,500 Swiss francs a month of software with tools he built himself, having described himself as technically illiterate six months earlier. The AI wall works the same way as the 50 unit wall. Once you break through it, it gets easier.

Resources and links mentioned

• Simon Lehmann Academy and consulting: simonlehmann.net (registration open now, full site live at launch)
• AJL Atelier: ajlatelier.com
• Simon's podcast: STR Global Unlocked
• Simon's video: The Five Levels of STR Companies Explained
• Simon's LinkedIn: linkedin.com/in/simonlehmann
• The Academy launches at VRMA International in the United States, and a day later at Vacation Rental World Summit in Lyon
• Heather's session on this topic: Scale Fest, Barcelona, October 2026
• Book a discovery call with Heather
• This episode is sponsored by StayFi. Use the code VRSUCCESS at stayfi.com for 50% off three months.

Connect with Simon

Simon works one-to-one with property management companies, most often in the 50 to 200 unit bracket, and is the person a lot of operators call when they know something structural has to change. If this conversation described your business more closely than you would like, he is worth talking to.

• Website: simonlehmann.net
• LinkedIn: linkedin.com/in/simonlehmann
• Podcast: STR Global Unlocked

‍