[Heather Bayer]

In the 12 years I've been hosting this podcast, I've recorded over 600 episodes, and the majority of them have been with industry leaders, people who've influenced this business significantly in one way or another. And we've touched on the topic of leadership before, but we've not given any specific focus on it until now. And the leadership series we're currently running is enlightening, it's inspirational, and there's a lot more to come.

But in this episode you're just going to hear from me, because I don't think we can really talk about leadership without bringing in a little theory, and along with that I wanted to revisit some of the previous episodes where we heard some gems from some really great leaders. Listen in.

This is the Vacation Rental Success Podcast, keeping you up to date with news, views, information and resources on this rapidly changing short-term rental business. I'm your host, Heather Bayer, and with 25 years of experience in this industry, I'm making sure you know what's hot, what's not, what's new and what will help make your business a success.

Well, hello and welcome to another episode of the Vacation Rental Success Podcast, I'm your host, Heather Bayer, and as ever, I'm super delighted to be back with you once again.

So as I said in that introduction, we are into our series on leadership right now. We've heard from Matt Landau, we've heard from Ali Cammelletti, and we've got some really great people coming along to talk about their approach to leadership. But it just struck me that I should perhaps give a little bit more context to this, a bit more structure to it. And so maybe once I've recorded this, I'll put this one at the beginning of the series, because that's perhaps where it should be.

But anyway, it sort of stemmed from listening to Matt and Ali, and questioning myself a little bit. And it's a question I've found myself going back to time and time again, over the years of being a property manager, running vacation rentals, hosting this podcast. And now co-founding an education and training company. And that question is, what kind of leader am I? What kind do I want to be? Is it possible to change? Should I go back and look at the theory that I learned way, way, way back in business school many, many years ago? So I may not find the answer to that question through this, you know, is it this is some sort of naval gazing, perhaps. But I've noticed that there's some really unique leadership styles emerging in our short-term rental world. And I'm going to go into those and draw inspiration from some of those people I've talked to over the years.

But before that, I want to set the stage a little with something foundational. And that's the classic leadership styles that are often taught in business schools. And these are the ones I remember from my days in college. That's just a few years ago now, so I shouldn't really have forgotten it. But it's worth reminding ourselves of these to appreciate just how diverse and dynamic our approaches have become. So if you've ever cracked open a management textbook, I don't know if any of you have, but if you have, you've likely seen a variation of categories. And if you've been around a while, you've probably experienced most of them. And I'm going to go through these fairly quickly because I do want you to carry on listening. And I know when I was at business school this sort of thing sent me...., I say it wasn't very long ago, but I don't think I had a cell phone then. But it probably would have sent me scrolling if I'd spent too much time on this.

So firstly, autocratic leadership, the my way or the highway approach. This is where decisions are made from the top down with little input from others. Efficient, yes, but very stifling. And it was definitely the approach taken by my bosses in my early years of working.

Then there's democratic leadership. And this is the style that invites collaboration and team input. Leaders still make the final call, but they do welcome and consider ideas.

Then when I remember this one, laissez-faire leadership, which is French for let's do, and it's a hands-off approach and works really well when teams are self motivated and highly skilled. And I think when you've been working with people a long, long time, you can often see this laissez-faire leadership coming into play. And it's sort of thinking, you know what you're doing, go do it.

Then there is transactional leadership, which is built on a system of rewards and punishments. Usually in this type, there is clear structure, defined roles and performance based outcomes called transactional. To me, it's sort of traditional. That's what I remember mostly in my years of paid work, which actually wasn't many before I started starting my own companies. But anyway, I remember that.

Then there's transformational leadership. These are the visionary motivators and leaders who inspire, who challenge the status quo and lead change. And business schools today tend to gravitate towards transformational leadership as a gold standard. In many ways, it sort of aligns what we're seeing evolve in our space right now. But our industry isn't a classroom. It's not a corporate tower. It's human. It's messy. It's personal. And that's what we're going to go into in this session.

So it's worth noting our short-term rental world is filled with visionaries, innovators and deeply compassionate people. From those who build businesses grounded in spiritual purpose, to others who embrace creativity or operational excellence. These are the guiding stars. But leadership in this space is as varied as the properties we manage.

So what makes our industry unique from a leadership perspective? I have noted down here three key factors. Number one is the personal nature of our business. And that's, you know, we're welcoming literally welcoming people into homes, creating spaces for memories. And it's an intimate connection, which demands authentic leadership. And you're going to hear a bit from Matt Landau later on, who talks a lot about authentic leadership.

The second one is the rapid pace of change. And we see this all the time from regulatory shifts and certainly to technology disruptions. Leaders in our space have got to be exceptionally adaptable. And then finally, it's the blend of hospitality and real estate, you know, straddling two complex industries which require leaders who can think across disciplines.

And Jim Collins in Good to Great, which is a super book, introduces the concept of level five leadership. And that's leaders who blend personal humility with professional will. And he writes, level five leaders channel their ego needs away from themselves and into the larger goal of building a great company. It's not that level five leaders have no ego or self-interest; indeed, they're incredibly ambitious, but their ambition is first and foremost for the institution and not themselves. And I've seen this same sort of humble determination in so many short-term rental operators who put their properties and their guests and their teams before personal recognition.

So in this solo episode, I want to explore some of the leadership styles I've observed in the guests who've come on the podcast over the years. These are individuals whose insights have not only shaped their own companies, but they've helped inspire me as well as countless others to do better and be better. So we'll look at leadership through some different lenses, through spiritual, creative, transformational, cultural and joyful.

And I'm going to share some of the most resonant quotes and takeaways that have stuck with me through the years. So the first one I'm visiting is the spiritual leader. And if you've ever met Valerie Gangas from Juniper Holiday + Home, you will understand why I'm starting with Valerie. She joined me on episode VRS584 and that episode made such a lasting impact on me. She brought this unique blend of hospitality and experience and her own spiritual mindfulness to the table. She spoke of designing guest experiences as if they were sacred rituals. Every detail was infused with intention.

She said, I've always been about creating experiences for people, that's what lights me up. And when I found myself in vacation rentals, it just made sense. Every space is an opportunity to uplift, to connect, to bring people joy.

Valerie's approach aligns with spiritual leadership. It's not about religion, but it's about infusing our business with deeper purpose, creating meaningful experiences for everybody, for all our stakeholders. And she reminded me that leadership isn't just about systems and scalability. Sometimes it's about other things, presence, intuition and showing up in a way that leaves people better than we found them. And she also touched on how transcendental meditation shaped her perspective, how peace and purpose could live alongside profit. And I found that incredibly moving. In a world that so often chases scale and speed, her style of grounding leadership was a real breath of fresh air.

As this episode is published, if you're listening to it at that time, Valerie is heading to Costa Rica to go to the Here Goes Nothin' retreat that I believe she's helping Matt Landau with on this occasion. She will be joining me on the podcast when she gets back from Costa Rica, and we're going to be spending a lot more time talking about spiritual leadership and what her retreat down in Costa Rica has brought her in the way of inspiration and new thinking.

So going back to the old business books, leadership expert Robert Greenleaf termed this servant leadership back in the 1970s. And he said, the servant leader is servant first. It begins with the natural feeling that one wants to serve, to serve first, then conscious choice brings one to aspire to lead. But for Valerie, service isn't just to guests, it's to a higher purpose that infuses everything she does. She creates spaces that nourish the soul, both for those who stay in her properties and for those who work alongside her. So I asked her about balancing spirituality with business pragmatism and she shared in the episode:

"People think spirituality means you have to abandon practicality. That's not it at all. Being spiritually grounded actually makes me more effective. I make clearer decisions, I attract the right team members and honestly, I enjoy the journey so much more."

And her leadership reminds us that profit and purpose aren't at odds. They're actually better together.

So the second style I wanted to address is the creative facilitator. And of course, if you're listening to this series, you'll have heard Matt Landau two episodes ago talking about this. And I've lost count of how many times Matt Landau has appeared on this podcast. Every single time I walk away inspired. On that episode, episode VRS607, we delve into a theme that's been central to Matt's work recently. And he's called it breaking out of the bubble. He says, we get so caught up in the day-to-day that we forget to ask, what are we actually doing here? And the real breakthroughs happen when we step back and reimagine our purpose.

Matt has evolved, and I think he's always been this way as a creative leader, one who disrupts and questions and reconstructs not only his own way of working, but the entire ecosystem around him. Through retreats like Keystone and the Here Goes Nothin' retreats that are going on at the moment, he's championed a form of leadership that invites people to be introspective, to be vulnerable, leading to transformation. He's also shown that creativity doesn't mean chaos. It actually does in my world, and I need to really get to grips with this one. But his work is rooted in human connection and storytelling. And it's something that often gets lost in our increasingly automated world. We've talked about this a lot when we've talked about AI. But he reminds us that creativity isn't a bonus, it's a necessity, and that's powerful.

In our conversation about leadership within communities, he said:

"The best leaders I know don't create followers, they create more leaders."

And this echoes what leadership researcher Bernard Bass identified as a key component of transformational leadership, intellectual stimulation. Great leaders challenge assumptions and encourage creative thinking in others.

Matt's approach to leadership also embraces what psychologist Carol Dweck calls a growth mindset. The belief that abilities can be developed through dedication and hard work. And as Matt often says, we're all works in progress. The moment you think you've figured it all out is the moment you stop growing. And those Keystone retreats, and now the Here Goes Nothin' program just exemplifies this philosophy. In them, he was working with Steve Schwab on the Keystone retreats. And I've spoken to so many people that went to those retreats. And they created spaces where people could step away from operational life in the business to engage in really deep reflection and collaborative problem solving. And it's a form of leadership that values curiosity over certainty, which is a refreshing approach in an industry that's constantly evolving.

I've dived deeply! I mean, I've been deeply involved in the philosophy that Steve Schwab has created for Casago recently. And he is walking the talk in this in terms of creative leadership.

Talking of Steve Schwab, in our milestone 500th episode, I brought together Steve along with Robin Craigen for a conversation about the future of short-term rentals. What struck me most was their long-term thinking and their ability to evolve without losing sight of core values. So Steve's story from a startup in Mexico to franchising across the US and now the acquisition of Vacasa is a real lesson in scaling with integrity. He said:

"I realized that the people on the ground needed ownership. That's how we created real accountability and real success."

Robin, on the other hand, spoke of weathering the pandemic and growing his company methodically, always with people at the center. He said:

"We built this slowly over decades. You don't get to skip the hard parts. You just stay the course."

Both of these exemplify what I call transformational leadership, the kind that plays the long game. They adapt with grace and they bring others along for the ride. But they both also emphasize something that is critical and that's resilience. These are leaders who don't crumble when times get tough. They recalibrate, they refocus and they keep going, not by chance, but by choice. Steve exemplified this when he told me, during COVID, when everything shut down:

"We didn't just go into survival mode. We actually doubled down on our tech investment. It was scary, but we knew that when travel returned, the landscape would be different. The discipline paid off."

And Robin shared a similar philosophy, but with a different application:

"We've had opportunities to grow much faster. Investors have approached us repeatedly, but we've always chosen sustainable growth over explosive expansion. That's why we're still standing when others have come and gone."

This kind of disciplined leadership isn't flashy, but it's really effective. It's about making consistent progress while staying true to your core mission, which is a balance that both Steve and Robin have mastered.

Let's move on over to the ladies now. And I want to talk about Rachel Alday from Abode Luxury Rentals and Rebecca Cribben from Holiday Rental Specialists, because they're both standout examples of what I describe as value-based leaders. Their success is deeply intertwined with a culture of care for their teams, their guests and themselves. And Rachel in particular talked about nurturing a workplace where people feel safe to grow. And she said:

"If your team doesn't feel trusted or empowered, your business can't grow. Culture isn't a perk, it's the foundation."

Rebecca Cribben has been a powerful voice on building ethical sustainable businesses, from mentoring hosts to promoting responsible practices. Her leadership is rooted in responsibility and legacy. And these are the leaders who ask, what kind of a place are we creating for others, and then do the hard work of living the answers every day? I think their examples remind us that leadership isn't just about numbers and margins, it's about stewardship. It's about leading in a way that makes people feel that they belong.

Steve Schwab has this as the cornerstone of the Casagao culture. I was in Rocky Point, Mexico earlier this year, visiting the Casagao team, and it was a delight to see them proudly wearing badges with the Old English version of the word steward on them. It's spelled S-T-I-G-W-E-A-R-D, and he leaves that Old English spelling on there, because according to Steve, this invites conversation and questions, meaning his people, the people who are working for him who are wearing those badges, are sharing their vision of the culture widely as they explain what steward actually means.

So, organizational culture expert Edgar Schein defines culture as a pattern of shared basic assumptions that the group learned as it solved its problems of external adaptation and internal integration. In other words, much easier way of saying it, culture isn't accidental. It's cultivated through deliberate leadership. When I asked Rachel about how she builds culture in her business, she shared:

"We have rituals that matter. Every Monday we start with wins, personal and professional. We celebrate the small stuff. And when things go wrong, we have a no-blame policy. We ask what happened, not who messed up. These might seem like small things, but they add up to create psychological safety."

Then Rebecca's leadership particularly shines in how she approaches industry ethics. She said:

"In the early days of Airbnb, it was a Wild West. Everyone was just figuring it out. Now we know better, so we need to do better. That means respecting communities, being transparent with guests and creating sustainable business models."

Leadership isn't just about what's legal, it's about what's right. Her perspective echoes what Harvard Business School Professor Bill George calls authentic leadership, leading from your core values and purpose. As George puts it, authentic leaders are genuine, transparent and trustworthy. They have a clear sense of purpose and are guided by sound values. They lead with their hearts as well as their heads, building enduring relationships with people. Both Rachel and Rebecca demonstrate this heart-centered, values-driven approach to leadership that's particularly vital in an industry that touches people's homes and the communities that surround them so directly.

Moving on now to what I've called the Joyful Organizer, and if you've ever met Lauren Madewell from Auntie Belham’s Cabins of Gatlinburg, you will know that this title fits her perfectly. She brought such a delightful twist to leadership and she infuses it with an authentic sense of fun. She says:

"We embrace the weird. If you can't laugh about this industry, you're going to lose your mind!"

Her leadership style is one we don't talk about anywhere near enough. It's about resilience through light-heartedness, about uniting a team not just through KPIs but through shared smiles and inside jokes. Lauren proves that professionalism and playfulness aren't mutually exclusive. She also demonstrated to us that morale isn't just a nice to have, it's a productivity tool. A happy team delivers better service, period. I love it that she's created an environment where laughter and excellence can coexist. This approach finds support in positive psychology research.

In Barbara Fredrickson's Broaden and Build Theory, she suggests that positive emotions like joy don't just feel good, they expand our thinking and build resources that help us thrive. When I asked Lauren about maintaining team spirit during the chaotic summer season, she shared:

"We have a tradition called Fail Friday, where we share the week's funniest mistakes, including mine. Last week, I accidentally sent our maintenance guide to the wrong cabin, twice."

By laughing together, we normalise that perfect isn't possible, but improving is always the goal. And her approach resonates with what researcher Brené Brown discovered about vulnerability and leadership. Vulnerability is not winning or losing, it's having the courage to show up and be seen when we have no control over the outcome.

And I love that quote. Lauren's willingness to share her own mistakes creates a culture where learning is valued over perfectionism, a particularly important quality in our really unpredictable world of vacation rentals. She also shared a practical insight about joy as a leadership tool:

"We track the usual metrics, occupancy, revenue, guest satisfaction, but we also track team laughter. If we go a whole day without someone cracking up, something's wrong. Joy isn't frivolous, it's fundamental to surviving in this business."

I really connected with that, because joy is one of my five key values in life. And it's heartening to see that there are leaders out there that are adopting and embracing the value of joy within their business.

So another voice that stood out to me in past conversations is Valerie Hawkins. Valerie's from Perdido Realty Vacations down on the Gulf Coast, and she brings what I think of as harmonizing leadership, which is a blend of operational wisdom, people-first mindset, and intentional balance. Valerie's been in this business for over 30 years, and she doesn't lead from the spotlight. I've been down and sat in her office and seen how she leads her people. And she leads from the center. She brings people together. She makes space for others to thrive, and she knows when to step forward and when to step back. And she said:

"There's strength in stillness. When you create calm at the top, it cascades through the whole organization."

And that quote stayed with me. Valerie reminds us that leadership doesn't always need to be loud to be effective. Her quiet confidence and strategic humility are traits we should all consider cultivating. Valerie's philosophy on facing industry challenges is equally insightful:

"When regulations changed dramatically in our area, everyone panicked. But I knew that rushing to react would just create more chaos. So we took three days to fully understand the changes, created a clear plan and then communicated with absolute confidence. That calm approach kept our owners from fleeing and gave our team direction."

So her methodical approach echoes what the psychologist Albert Bandura termed self-efficacy. And that's the belief in your own ability to succeed in specific situations. Leaders with high self-efficacy stay calm under pressure, and they approach difficulties as challenges to be mastered rather than threats to be avoided. When I asked Valerie about developing future leaders in her organization, she said:

"I look for people who listen more than they speak. Technical skills can be taught, operational processes can be learned, but that quality of presence of truly being with people rather than just waiting for your turn to talk, that's the foundation of leadership in a people business like ours."

So as we reflect on these diverse leadership styles in the short-term rental space, it's worth connecting them to broader leadership research. And this field of leadership research has evolved a lot from trait-based theories, which just focused on the inherent qualities, to then behavioral approaches, examining what leaders do, and to contingency models, recognizing that effective leadership depends on the situation.

So some of the more recent theories you've already heard, as I've talked through some of our guests, so there's authentic leadership focused on transparency and ethical foundations and self-awareness, servant leadership prioritizing the growth and well-being of team members and communities, adaptive leadership emphasizing flexibility in facing complex challenges, and shared leadership where leadership responsibilities are distributed across a team rather than concentrating them in a single person. So what's fascinating is that our industry naturally incorporates elements of all these approaches. The best short-term rental leaders adapt their style to the situation while remaining true to their core values, whether those center on guest experience, team culture, or community impact, or business innovation.

And as leadership scholar Warren Bennis noted, leadership is the capacity to translate vision into reality. So in our world, that vision might be creating exceptional guest experiences, building sustainable business models, or transforming how people travel. And the translation happens through the unique leadership styles we've explored.

So back to the question, what kind of leader are you? Maybe you see yourself in one of these styles, or maybe you're a mix, but the truth is there's no single blueprint. Leadership in short-term rentals is much about who you are, as about what you do. It's about making choices with intention, it's about knowing your strengths and owning your blind spots, about growing not just your business, but yourself.

So here's what I've learned from years of conversation and mistakes of my own. Leadership is personal, it's cultural, it's constantly evolving, and perhaps most importantly, leadership is a reflection of what we value most. And you've probably heard this quote from management expert Peter Drucker, who said, management is doing things right, leadership is doing the right things. In the short-term rental industry, both matter enormously. We need operational excellence and visionary direction. We need systems and soul. We need to be both practical and purposeful. So one exercise I found helpful in my own leadership journey is called the leadership legacy reflection. And it's when you ask yourself, five years from now, when someone who worked with me describes my leadership, what three words do I hope they'll use? Try it yourself. The words that come to mind reveal a lot about what matters most to you as a leader.

Another practice is to identify your leadership mentors, both within and outside our industry. Who inspires you? Whose approach resonates with your values? What qualities do you admire and want to cultivate in yourself? I'm lucky, over the years of doing this podcast, I've had in-depth conversations with countless exceptional leaders and I've learned so much from them. I have the transcripts from every discussion. I can use AI to draw out the best parts. You can do that. You can download transcripts of podcasts, not just mine, but listen to the leaders that inspire you on podcasts, download the transcripts and then ask AI questions from those transcripts.

You could also reflect on who inspires you on LinkedIn. Think about who you're following the most. What are their leadership styles and what could you adopt for yourself? So as you reflect on your leadership style, remember that authenticity matters more than perfection.

Brené Brown says authenticity is the daily practice of letting go of who we think we're supposed to be and embracing who we are. This is not as easy as it sounds, but it is definitely something to have a go at. But the most effective leaders in our industry aren't trying to fit in some external mould. They're leaning into their unique strengths and also remaining open to growth. So wherever you are in this industry, the question is always worth asking because the clearer we get about who we are as leaders, the more impactful we can be. And that's for our teams, for our guests, our communities and everyone we come across.

So I'll leave you with this. Take some time this week to step back. Look at how you show up. Ask your team what kind of leader you are. Journal it. Meditate on it. Or just have a coffee and daydream about what kind of company you really want to build. And then go lead like it matters, because in this industry, it truly does. Leadership isn't just about reaching goals, those business goals, even though those matter, but it's about the lives we touch along the way. The team members, the people who work with us, who grow under our guidance. The guests who we come across every single day, who create memories and spaces that we curate. The communities we help thrive through responsible and sustainable tourism.

One more quote before I go, and this is from anthropologist Margaret Mead, who famously said:

"Never doubt that a small group of thoughtful committed citizens can change the world. Indeed, it's the only thing that ever has."

So in our own way, through thoughtful leadership in the short-term rental space, we're changing how people experience travel. We're changing how they experience their local communities and perhaps even we're changing how they are at home. And that's worth leading well.

Thank you for being with me on this journey. I hope this episode resonated with you. And if it did, I'd love to hear your thoughts. You know, you can share it. You can tag me, drop a comment. Conversations about leadership are ones we should be having more often. So I'd love to hear from you.

Until next time.

It's been a pleasure as ever being with you. If there's anything you'd like to comment on, then join the conversation on the Show Notes for the episode at vacationrentalformula.com. We'd love to hear from you and I look forward to being with you again next week.

‍