Conferences and events are great, but unpredictable. Investing in predictable relationships yields predictable results — rather than waiting for an annual event with an uncertain crowd, you can count on exclusive, private monthly meetings with the same people, invested in your success.
Billionaire steel tycoon Andrew Carnegie credited his fortune to his MasterMind group — inspiring Napoleon Hill to coin the term in "Think and Grow Rich" in 1937.
A MasterMind cohort is a group of 8–11 peers who meet regularly to learn each other's businesses — supporting and sharing advice in the collective form of "what works for me." Unlike mentoring, it's mutual: you give as much as you receive. In the best groups, members hold each other accountable for their goals, driving each other to the highest levels of success.
Meetings are held monthly in a confidential online space, scheduled a year in advance. We're shooting for 100% attendance every time — missing a meeting doesn't just affect you, it affects every member who doesn't get your experience in the room.
Having surveyed many versions of masterminds across his career as a short-term rental property manager, board director, sales leader, consultant, and strategic advisor, Tristan Webb built a true MasterMind — created specifically for STR property manager entrepreneurs, industry vendors, and white-label services — to help them transform their companies well beyond their own vision. He grew his Park City, UT portfolio to 96 luxury ski homes, authored a short-term rental ordinance later adopted by his own city, served as a VRMA Board Member co-chairing Government and Public Relations, co-managed production of the 21-episode PBS & Amazon Prime series "Getting Away Together," and consulted cities and developers on purpose-built STR communities including Paradise Village at Zion. His company was later acquired by Vacasa, where he led new-home inventory sales. He now serves as Senior Strategic Advisor at Vintory while facilitating 10+ MasterMind groups and 200+ business owners monthly.
Every word below is unedited, from members and colleagues — presented in full.
"Having been in Tristan's monthly master mind for well over 3 years, I get a front row seat to a caring and thoughtful leader who knows how to masterfully facilitate learning and dreaming. He knows how to steer a group towards purposeful conversation and accomplish the objectives of our mastermind group. Tristan is someone whose opinion I value and seek out when confronting obstacles and challenges in business. He doesn't tell you what to do—he leads you to discovery. So thankful I landed in Tristan's group."
"Tristan is a master facilitator. From our days at Vintory, I knew him as a source of stoic wisdom, but seeing him run a mastermind is next-level. He knows exactly how to match personalities and hold a safe space for the group. He keeps things productive, focused, and genuinely impactful."
"Tristan is an excellent leader, communicator, source of knowledge and all around kind person. I have the utmost respect for his experience, knowledge and leadership, and am fortunate to have benefitted from this directly in my experiences in his Master Mind groups. I would highly recommend taking part in one of his Mastermind groups—and generally speaking recommend Tristan for his professionalism and expertise."
"I've been part of Tristen's vacation rental mastermind and can honestly say he's one of the best leaders I've learned from in this space. It's been a huge value add for my business. He also does a great job running the room. He knows when to push, when to challenge assumptions, and when to slow things down so people can actually absorb and apply what's being discussed. The conversations are focused, productive, and genuinely helpful. If you're serious about scaling a vacation rental business and want to learn from someone who's been in the trenches and done it, Tristen is the real deal. The mastermind is well run, high-value, and absolutely worth the time. 100% recommend."
"I really enjoy our Mastermind meetings with Tristan. Not only is he a past VRMA Board Member, he is a former vacation rental business owner, and been in this industry a long time, but his knowledge, expertise, and recommendations are top notch! I too have been in this industry a long time, but I write over a page of notes every time we meet. Tristan is also very likeable and is friendly, helpful, and an all around genuine guy. If you are looking to take your business to the next level or hear about the latest and greatest, contact Tristan! :)"
"Tristan's vast years of experience in the Vacation Rental Management industry enable him to think outside of the box with creative solutions and strategic insights as he guides similar professionals from across the county in his MasterMind thinktank group. I look forward to each session knowing I will have practical takeaways that I can immediately apply at my company."
"Tristan has been our mastermind facilitator for the past year or so, which made a valuable resource an invaluable part of our strategic plan. He does a great job of guiding the discussions and keeping us on track; while also allowing for the organic spread of intriguing topics that come in during the course of the meetings. He is always sure to seek input on how to improve and follows up with those recommendations in successive meetings. I look forward to all my interactions with Tristan, he is just a great guy!"
"Tristan has been a great friend and an incredible resource. Tristan's knowledge and experience of the vacation rental industry is immeasurable."
"Tristan has lead one of my mastermind groups for the past few years. He is always very professional and helps us stay on tasks. His communication is excellent and thorough. I highly recommend Tristan."
"When I was a property manager, I had the privilege to learn from Tristan as a MasterMinds facilitator. His industry expertise is top-notch and his facilitation style is inclusive, educational, and encouraging. Moreover, he took me aside to train me personally on micro-targeting tactics, something that has shaped my approach to sales even today now that I'm in the SaaS space. Whether one-on-one or in a group, I can't recommend his services enough!"
"Tristan is a stellar facilitator, community builder, and leader in our industry. He is a wealth of knowledge and humbly fosters growth for others. In his MasterMinds, he nurtures a cooperative and confidential space where vacation rental operators can come together to overcome challenges, share best practices, and all together elevate our industry. During my time as a property manager, I gained so much from Tristan's mentorship and from the community that was built in the MasterMinds. It truly helped move our business forward. Tristan has invaluable expertise, insights, and a teaching spirit that elevates others—making him a true leader."
"I have had the privilege of working alongside Tristan Webb in the vacation rental industry, and I can wholeheartedly attest to his exceptional professionalism and remarkable camaraderie. Tristan not only commands immense respect for his expertise within the field but has also become a valued friend. Tristan's prowess in the vacation rental industry is unparalleled. His ability to collaborate with fellow professionals is truly second to none, consistently elevating the collective achievement in any room he enters. Beyond his evident professional acumen, Tristan brings a genuine warmth and authenticity to his interactions, fostering a positive and collaborative work environment. In both a professional and personal capacity, Tristan Webb earns my highest regard. I consider myself fortunate to have collaborated with him and witnessed firsthand the positive impact he brings to any professional setting."
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