Short-term rental leaders unite behind new operator education as the industry professionalises
Simon Lehmann opens the STR Academy with Beyond, Guesty, Pikl and Breezeway as exclusive category partners and seven industry ambassadors, launched during VRMA week in Nashville
NASHVILLE, Tennessee, 5 October 2026 –The technology serving professional short-term rental operators has raced ahead. The education has not. Today that gap closes: the STR Academy, a structured online programme that takes property managers from operator to CEO, opens to the industry, backed by the category leaders in revenue management, property management software, insurance and operations, and endorsed by seven of the industry’s most respected independent voices.
The Academy is the work of Simon Lehmann, one of the industry’s longest-serving operators, who ran Interhome as CEO with 48,000 properties under management and served on the board of HomeAway through its sale to Expedia. It distils more than twenty years of operating decisions into nine sequential modules and more than ten hours of teaching, built for the professional operator managing 30 to 200 units, the segment where most growth stalls and most value is lost.
“This industry has spent a decade professionalising its tools and about ten minutes professionalising its people,” said Lehmann. “Operators can buy world-class software for every part of their business, and most still cannot say whether an individual property makes them money. The wall is not technology. It is the transition from running properties to running a company, and nobody teaches it. That is what the Academy is for.”
An industry closing ranks behind education
Rather than launching alone, the Academy opens with exclusive category partners who are putting their names, channels and customer relationships behind operator education: Beyond in revenue management, Guesty in property management software, Pikl in insurtech and Breezeway in operations. Each holds its category exclusively and will co-produce education with the Academy for its own customer base.
“Revenue management only works when the operator behind it understands their own economics. That is why we are backing the Academy: educated operators are better operators, and better operators grow,” said Julie Brinkman, CEO of Beyond.
“Getting from 30 units to 200 is a different job than getting to 30. The industry is maturing quickly, and the education around how to build and lead STR businesses as they scale needs to mature with it. The Academy is a chance to give more operators access to that knowledge, and that’s something we really want to support,” said Vered Raviv-Schwarz, President and COO, Guesty.
“Growth comes from understanding a business from every angle, and risk is an important part of that picture. The better operators understand their risk profile, the better equipped they are to see where there is opportunity to make informed decisions to grow with confidence. We’re supporting the launch of the STR Academy to give operators access to knowledge and insight to help them build stronger, more ambitious businesses.,” said Louise Birritteri, CEO of Pikl.
“Operational excellence is learned, not bought. We are proud to take the operations seat and to bring operations education to every professional operator,” said Jeremy Gall, founder and CEO, Breezeway.
The Founding Ambassadors
Seven industry figures have joined as Founding Ambassadors, endorsing the initiative of bringing structured education to the professional operator: Carl Shepherd, co-founder of HomeAway; Graham Donoghue, CEO of Sykes Holiday Cottages; Heather Bayer, author, podcast host and former operator; David Angotti, founder of SmokyMountains.com; Pete Smith, one of Australia’s longest-serving short-term rental operators; Antonio Bortolotti, host of the Vacation Rental World Summit; and Robin Craigen, co-founder of Moving Mountains.
“Most companies in this industry are built like a bicycle wheel, every spoke runs through the founder. The Academy teaches operators how to build a business that turns without them, and I have waited twenty years for someone with the operating record to teach it,” said Carl Shepherd, co-founder of HomeAway.
Open now, first places limited
The STR Academy is open for enrolment from today at simonlehmann.net. The programme is self-paced, taught by Lehmann throughout, and includes downloadable working tools with every module. The first twenty places carry Founding terms and are available until 13 October only. The Academy launches during the week of the VRMA International Conference in Nashville, where Lehmann moderates the session “True Cost to Scale” on Monday afternoon, and continues at the Vacation Rental World Summit in Lyon on 8 and 9 October.
About Simon Lehmann
Simon Lehmann is the founder and CEO of Simon Lehmann Advisory, the practice for professional short-term rental operators, investors and technology companies. Over more than twenty years in the sector he has led Interhome as CEO, served on the board of HomeAway through its sale to Expedia, chaired MadeComfy through to exit, and advised more than fifty companies at C-suite and board level. He hosts STR Global Unlocked, the industry podcast and newsletter.
About the partners
Beyond is the revenue management system that gives every operator, from the individual host to the enterprise property manager, the intelligence and control to run a more empowered, more profitable STR business. Guesty is the AI property management platform for short-term and vacation rental operators, with AI agents that work across revenue, accounting, guest communication, operations, distribution, owner relationships and finance. Pikl is the revenue growth partner for the travel market, backed by insurance. Breezeway is the AI-powered property operations platform for short-term rental and hospitality operators.
Media contact
Simon Lehmann
simon@simonlehmann.net