Why We Cap Growth at 100 Properties with Michael Steinkirchner of Uncharted Vacations

Michael Steinkirchener, founder of Uncharted Vacations, joins Lynell Gordon on The Vacation Rental Show to share his unconventional approach to building a vacation rental management company. Unlike competitors chasing unlimited growth, Michael deliberately caps his portfolio at 100 properties to maintain personal relationships with every owner and guest. He reveals his innovative "Redesign on Our Dime" program that finances property updates for cash-strapped owners while boosting retention and revenue. Michael discusses critical startup advice including choosing the right tech stack from day one, the importance of negotiating with vendors, and why cleaners deserve far more recognition than they receive. He shares insights on ancillary revenue streams, the surprising low uptake of travel insurance (currently 10-15% when it should be 30-40%), and how showing owners the monetary value of included services strengthens partnerships. This episode is sponsored by Streamline.

Most vacation rental managers chase unlimited growth, but Michael Steinkirchener is doing something radically different. In this episode of The Vacation Rental Show, host Lynell Gordon speaks with Michael, founder of Uncharted Vacations, about why he's deliberately capping his portfolio at 100 properties and how strategic limitations have become his competitive advantage. Michael reveals the innovative programs and partnership approaches that allow boutique operations to thrive in an industry obsessed with scale.

What you'll learn:

Why capping growth at 100 properties creates a competitive advantage through personalized service
How to finance property renovations for owners through an innovative retention program
Critical tech stack decisions that prevent costly migrations down the road
Negotiation strategies with vendors that can fund entire staff positions
Why travel insurance uptake should be 30-40% instead of the current 10-15%
How to demonstrate monetary value to owners through transparent accounting practices

Michael Steinkirchener brings a refreshingly different perspective to vacation rental management. As founder of Uncharted Vacations and the consulting firm Stream Advisors, he's built his business around a provocative idea: sometimes the best growth strategy is knowing when to stop growing. Michael has deliberately capped his portfolio at 100 properties, arguing that beyond this threshold, companies lose the intimate knowledge of owners and guests that defines exceptional service.

His "Redesign on Our Dime" program exemplifies this innovative thinking. When owners lack cash for necessary property updates, Uncharted finances the improvements and recoups costs through a slightly higher management fee over time. The result? Higher ADRs, improved retention, and owners who feel genuinely partnered with rather than simply managed. Michael also reveals how he demonstrates value by listing all included services on owner statements, then showing them discounted to zero, creating a powerful year-end tally that combats competitor poaching.

From startup advice about choosing scalable tech stacks before you have 600 reservations to migrate, to practical tips on negotiating credit card processing fees that could fund another employee, Michael offers actionable insights for managers at every stage. He's particularly passionate about recognizing cleaners as the backbone of the industry, sharing stories of providing emergency housing during hurricanes and surprising team members with new equipment.

This episode is sponsored by Streamline

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Previous guests include: Jim DeVos of Best Beach Getaways, Stacy Wesson of Cascara Vacation Rentals, Michael Friedman of The Simple Life Hospitality, Steve Caron of Inhabit, John An of TechTape, Jessica Gillingham of Abode Worldwide, Justin Ford of Breezeway, Mahwussh Alam of One Perfect Stay, Lisa Stinnett of Inhabit, and many more.

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