Simon Lehmann

Founding Circle

The people who built this industry
stand behind the Academy.

Operators, founders and dealmakers who have lived every stage of short-term rentals. In their own words.

Graham Donoghue Heather Bayer Robin Craigen Carl Shepherd Antonio Bortolotti David Angotti Pete Smith

Ambassadors

In their own words

Carl Shepherd
“Every company we acquired at HomeAway was what I call a bicycle spoke organization: the owner made every decision, and the company stalled because of its structure, not the market. Adding structure early is the only real path forward, and this Academy teaches exactly that.”

Carl Shepherd

Pete Smith
“I spent close to twenty years running short-term rentals in Australia, through every cycle this industry can throw at you, the booms, the platform shifts, the regulation scares, a pandemic. What strikes me about the Academy is that it teaches the things that stayed true through all of it: know your numbers per property, build the business so it runs without you, and treat your owners as customers, not landlords. I learned those lessons the slow way, over two decades and on the other side of the world. The fact that they hold from Australia to America tells you this is not theory, it is how the business actually works. I am glad to put my name to it.”

Pete Smith

Heather Bayer
“When Simon walked through his five levels on my podcast, I recognized my own company at every stage, including the point where it stalled. I ran Cottage Link right up to the wall he describes and chose to sell rather than push through, and I have never regretted that, but I know the business would have been worth more, and my life a good deal easier, if I had made the structural changes he teaches ten years before I finally did. That is what this Academy does. It does not tell you that you are doing fine; it shows you what has to change before the next stage is possible, and it does it with the numbers and the structure I never had.”

Heather Bayer

Robin Craigen
“This program is an inspiring opportunity for vacation rental managers to fast track their learning and build a path to a stable and profitable future. Every piece of content I reviewed resonates with lessons I learned the hard way over 30 years. We found our solutions and worked through the challenges that come with growth, often by making the wrong choices first and paying for them in time and money. I have no doubt that if I had access to this program 10, 15, or 20 years ago, our business would have thrived faster and run more efficiently at a much earlier stage. I would recommend this to any founder or business owner serious about long term success in our industry.”

Robin Craigen

Graham Donoghue
“I am excited to work with Simon and the other advisory members. The Academy clearly reflects Simon’s experience, and I have no doubt it will quickly become an essential industry training resource, providing practical, authentic education that drives better outcomes and more effective delivery for all.”

Graham Donoghue

Forge Holidays

Antonio Bortolotti
“What stands out to me about the Simon Lehmann Academy is the connection between learning and doing. From identifying the barriers to growth to understanding profitability property by property, its focus is on helping operators make clearer decisions and build businesses less dependent on their constant involvement. That practical approach to education is something I strongly believe in, and I’m glad to support it.”

Antonio Bortolotti

VRWS

David Angotti
“I have spent more than twenty years bringing this industry together, and the pattern never changes: operators do not fail for lack of passion or lack of tools, they fail because nobody ever taught them how to run the business behind the properties. Simon is one of the very few people who has actually done it at every level, from the single unit to the boardroom, and the Academy is that experience made teachable. This is the education our industry should have built years ago. I am endorsing it because our attendees, and operators everywhere, deserve it.”

David Angotti