September 01, 2026

#200 ​​​Episodes Later: The Biggest Lessons About Short-Term Rental Success with Stacey St. John

Episode 200 of the STR Sisterhood landed on my birthday, and I consider it a gift to have had 200 conversations about short-term rental success with women around the globe. When reflecting on what I’ve learned along the way, I’ve realized the biggest lessons haven’t actually been about short-term rentals at all. They’ve been about people.

Have you ever looked at someone else’s business and wondered if they know something you don’t?

I have. We see the beautiful properties, the sold-out retreats, the podcast rankings — and we assume there’s a blueprint everyone else got a copy of except us.

There’s No Secret Blueprint for Short-Term Rental Success

There isn’t one. When I started this podcast, I thought I was interviewing women to learn the secrets. I couldn’t have been more wrong.

I’ve interviewed teachers, nurses, military spouses, stay-at-home moms, and corporate executives. Some started with a beach condo like me. Some inherited a property. Some never owned property at all and built co-hosting businesses instead.

There wasn’t one personality type, one perfect market, or one financing strategy.

The only thing these women consistently had in common — the closest thing to a short-term rental success formula I’ve found — is that they stopped waiting for permission.

Here are the four lessons they’ve taught me.

Lesson 1: Extraordinary Women Stop Waiting for Permission

“Stacey, what’s the best way to get started?” If I had a dollar for every time someone asked me that, I’d probably have a few more beach houses. Buy? Co-host? Arbitrage? Manage for someone else?

Everybody wants the right path. But the women who build extraordinary businesses aren’t the ones who had everything figured out before they began. They’re the ones who decided to begin before they had everything figured out.

That isn’t a mindset difference. It’s an operating difference. Short-term rental success doesn’t start with certainty. It starts with a decision you own.

Confidence Is the Reward for Action, Not the Requirement

Most of us believe confidence comes first. One more podcast. One more book. One more free download, and then we’ll finally feel ready.

That isn’t how it works. Confidence is the reward for action, and the research agrees — Harvard Business School’s Teresa Amabile found that small, visible progress does more for motivation than anything else people experience at work.

Every woman I’ve interviewed has made mistakes. Wrong furniture, wrong cleaners, underpriced properties. The difference isn’t that successful women avoid mistakes. It’s that mistakes don’t convince them to stop.

So here’s the leadership question underneath it: what decision are you postponing while you collect information you already have?

In 200 episodes, I’ve never interviewed a woman who told me, “I’m so glad I waited until I felt perfectly ready.” Not one. But plenty have said, “I wish I would have started sooner.”

Lesson 2: Build the Right Business, Not the Biggest One

“How many properties should I have?” is the question I get asked most. After 200 conversations, I’ve realized it’s the wrong one.

The better question: what kind of life am I trying to build?

Somewhere along the way we got sold the idea that success always means more. More properties, more revenue, more team, more recognition.

But I’ve interviewed women who own one vacation rental and love their lives, and women who manage dozens. Some left six-figure corporate careers to co-host, because what they wanted wasn’t a portfolio — it was flexibility. Some wanted generational wealth. Some just wanted enough extra income to take their grandkids to Disney every year.

None of those dreams is more valuable than another. There isn’t one definition of short-term rental success. You get to decide.

Comparison quietly steals contentment. Someone scales to thirty doors, and suddenly the business you were proud of yesterday doesn’t seem big enough.

Here’s the truth: your business exists to serve your life. Your life doesn’t exist to serve your business.

If you can’t tell which direction yours is running, name that before you add another property. It’s the same clarity work I walked through in how to know when to pivot your STR business.

Lesson 3: Information Doesn’t Change Lives — People Do

This one surprised me most, and I know it sounds strange coming from a woman who hosts a podcast.

I’ve interviewed women who’d never listened to a podcast before buying their first property, and women who could teach a master class after years of consuming content. Neither succeeded because of how much she knew. They succeeded because they kept moving, and almost every one of them had people helping them move.

Why Proximity Drives Short-Term Rental Success More Than Information

Maybe it was a mentor, another host, or a mastermind. Maybe it was a group of women who simply reminded them, “You’ve got this.”

When you’re surrounded by people asking bigger questions, something shifts. Not because anyone hands you short-term rental success, but because they keep reminding you that you’re capable of creating it.

Community doesn’t just give you answers. It gives you courage, perspective, and accountability. On the days you doubt yourself, it gives you someone else’s belief to borrow until your own catches up.

The women who built extraordinary lives didn’t have extraordinary information. They had extraordinary support.

So maybe what you’ve been missing isn’t information. Maybe you’ve been trying to build this by yourself — exactly the gap the strategic power of an STR mastermind is built to close.

Lesson 4: Build a Business That Gives You Your Life Back

We get into short-term rentals chasing freedom. Nobody starts this dreaming about answering guest messages at midnight or checking the calendar on family vacation.

But something subtle happens. The business grows, responsibilities increase, and before long you’re serving the business more than it’s serving you. I’ve lived seasons of that.

That’s why I’ve become so passionate about systems. Not because I love checklists, but because systems create freedom. Every system is really a decision you’ve made once, so you don’t have to keep making it again.

Every responsibility you truly delegate — the decision, not just the task — creates room for something that matters more. That’s the same shift I broke down in Kendra Scott’s lessons for better Airbnb business systems.

Real short-term rental success isn’t a bigger calendar. It’s a business that keeps running when you step away.

What 200 Episodes Taught Me About Short-Term Rental Success

The women I admire most aren’t the ones with the biggest portfolios or the highest revenue. They’re the ones who never forgot why they started.

Short-term rental success isn’t measured by how much you’ve built. It’s measured by whether what you’ve built gives you the life you were hoping for.

My own definition changed, too. Ten years ago I’d have measured it in bigger numbers. Today, the greatest wealth is the freedom to decide how I spend a Tuesday afternoon.

So build the business. Learn, take risks, surround yourself with incredible people. Just never forget that the business is the vehicle. The life you’re creating is the destination.

You don’t have to have everything figured out before you begin. You simply have to take the next step.

Listen to episode 200 on the STR Sisterhood podcast, then name the one decision you’ve been postponing and make it this week. If you’d rather stop making that decision alone, the STR Sisterhood is where that changes.

Click here now to listen to the full podcast.

HIGHLIGHTS AND KEY POINTS:

Golden Nuggets:

• “Be a first-rate version of yourself instead of a second-rate version of somebody else.”
• “Extraordinary women stop waiting for permission.”
• “The women who build extraordinary lives aren’t the women who have everything figured out before they begin-they’re the women who decide to begin before they have everything figured out.” •“Confidence is the reward for action.”
• “Success isn’t about building the biggest business. It’s about building the right one.”
• “Information alone doesn’t change lives; other people do.”
• “Your business should support your life. It should never replace it.”
• “The women I admire most aren’t the women with the biggest portfolios. They aren’t the women making the most money. They’re the women who never forgot why they started.”
• “You don’t have to have everything figured out before you begin. You don’t have to become someone else before you deserve success. You don’t have to build the biggest business to build a beautiful life. You simply have to take the next step, because somewhere out there is a future version of you.”

Connect With Stacey:

Join the STR Sisterhood : https://strsisterhood.com/ 

Full Episode Transcript:

 

Welcome to another episode of the STR Sisterhood. I’m your host, Stacey St. John, and I am so stinking excited to spend some time with you today. Thanks for allowing me to join you today.

Now, before we jump into this episode, you know it, girl, I’m gonna share a quote with you that I recently read, and it says, “Be a first-rate version of yourself, instead of a second-rate version of somebody else.” Those beautiful words come to us from the one and only Judy Garland.

Have you ever looked at someone else’s life or business and thought, “Wow, they make that look so easy?” I know I have. We see the beautiful properties, the sold-out retreats, the successful businesses, the podcast rankings, the smiling family photos, and it’s so easy to assume that somehow everyone else figured something out that we didn’t. Like there’s a secret blueprint that everyone else got a copy of except us.

Today is a really special day for me. It’s my 200th podcast episode. It also happens to be my birthday, and it’s the beginning of an exciting new chapter for the STR Sisterhood community.

As I was thinking about what I wanted to share with you today, I realized I could talk about systems, revenue, marketing, guest experience, or business strategy. And while I love all of those things, none of them felt quite right. Because when I look back over the last 200 episodes, I don’t think the greatest lessons have actually been about short-term rentals. They’ve been about people.

For the last few years, I’ve had a front-row seat to hundreds of conversations with women who have built incredible businesses. Teachers, nurses, corporate executives, stay-at-home moms, military spouses, women who started with one property, women who built co-hosting businesses, women who own dozens of properties.

And if I’m honest, when I started this podcast, I thought I was interviewing them to learn the secrets of successful short-term rentals. Boy, I couldn’t have been more wrong.

What I was really witnessing was ordinary women becoming extraordinary, not because they were smarter than everyone else or because they had some unfair advantage, but because they made one decision after another that moved them toward the life they wanted.

And here’s what’s so interesting. The more women I’ve interviewed, the less I believed there was a secret formula. There wasn’t one personality type that succeeded. There wasn’t one perfect business model. There wasn’t one perfect market. There wasn’t one perfect financing strategy. There wasn’t one definition of success.

In fact, the only thing these women consistently had in common was that they stopped waiting for permission to build the life they wanted.

And I have to tell you, that realization changed me, because like so many of you listening today, there have been seasons in my own life where I wondered if I was ready, seasons where I questioned whether I was enough, whether I was making the right decision, or whether I should just wait a little longer until I felt more confident.

Maybe you’ve felt that way, too. Maybe you’ve spent months listening to podcasts, watching YouTube videos, reading books, saving posts on Instagram, filling notebooks with ideas. Maybe you know more about short-term rentals today than you did a year ago, but somehow you’re still standing in the same place.

If that’s you, I want you to know something before we go any further. This episode isn’t about celebrating 200 podcasts. It’s about celebrating what’s possible for you.

Because after 200 conversations, if there’s one thing I know for sure, it’s this: extraordinary lives aren’t reserved for extraordinary people. They’re built by ordinary women who decide to stop waiting, they start believing, and they take the next step.

So today, I wanna share the four biggest lessons these incredible women have taught me. Not just about building a short-term rental business, but about building a life you absolutely love, because I have a feeling that one of these lessons might be exactly what you need to hear today.

Lesson number one: extraordinary women stop waiting for permission.

One of the biggest lessons I’ve learned after 200 episodes is this: the women who build extraordinary lives aren’t the women who have everything figured out before they begin. They’re the women who decide to begin before they have everything figured out.

If I had a dollar for every time someone asked me, “Stacey, what’s the best way to get started in short-term rentals?” I’d probably have a few more beach houses. “Should I buy a property? Should I co-host? Should I arbitrage? Should I manage for someone else?”

Everyone wants to know the right path, and honestly, when I started this podcast, I thought that’s what I would eventually discover too. I thought that after enough interviews, I’d finally uncover a secret formula. I imagined the most successful women would all have similar backgrounds, similar personalities, maybe even similar businesses.

But after 200 conversations, that’s not what I found at all.

I’ve interviewed teachers, nurses, accountants, military spouses, stay-at-home moms, corporate executives, real estate agents, retirees, women from every imaginable background. Some started with a beach condo like me, others with a cabin. Some inherited a property. Others saved for years to buy their very first investment. Some had never owned a property at all, and they built incredible co-hosting businesses instead.

Their businesses couldn’t look more different. Their goals couldn’t look more different either. Even their personalities couldn’t look more different. Some are outgoing, others are incredibly quiet. Some love taking risks, others are analytical and cautious. Some wanted to replace a six-figure income. Others simply wanted enough extra income to take their family on vacation every year.

If you looked at these women on paper, you would never put them in the same category. But there was one thing every single one of them eventually did. They stopped waiting.

They stopped waiting until they knew everything. They stopped waiting until they felt completely confident. They stopped waiting until someone else told them they were ready. Instead, they made a decision, and then they figured out the next step.

You know, I think that’s where so many folks get stuck. We convince ourselves that confidence comes first. That one more podcast, one more YouTube video, one more book, one more free download that will finally make us feel ready.

But after talking with hundreds of women who’ve built incredible businesses, I don’t think confidence comes before action. I think confidence is the reward for action.

Every woman I’ve interviewed has made mistakes. Every single one. They’ve bought the wrong furniture, they’ve hired the wrong cleaners, they’ve underpriced their properties, they’ve had difficult guests, and they’ve questioned themselves.

The difference isn’t that successful women avoid mistakes. The difference is they don’t let mistakes convince them to stop. They keep moving, and that’s what builds confidence.

So if you’ve been listening today and you’re waiting to feel completely ready before you take your next step, let me lovingly challenge that belief. Maybe readiness isn’t a feeling. Maybe it’s a decision. Maybe the woman you’re hoping to become isn’t waiting for one more piece of information. Maybe she’s just waiting for you to trust yourself enough to begin.

Because after two hundred conversations, I can tell you this with complete confidence. I’ve never interviewed a woman who said, “I’m so glad I waited until I felt perfectly ready.” Nope, not one. But I have interviewed countless women who said, “I wish I would have started sooner.”

And maybe that’s the lesson you needed today.

Lesson number two: Success isn’t about building the biggest business. It’s about building the right one.

One of the questions I get asked all the time is, “Stacey, how many properties should I have in my portfolio?” And every time somebody asks me that, I smile, because after 200 conversations, I’ve realized that’s actually the wrong question.

The better question is, what kind of life do I want to build?

You see, somewhere along the way, we’ve been sold this idea that success always means more. More properties, more revenue, more team members, more followers, more recognition, more, more, more. And if we’re not careful, we can spend years chasing someone else’s definition of success instead of intentionally creating our own.

I’ve interviewed women who own one vacation rental and absolutely love their lives. I’ve interviewed women who manage dozens of properties. I’ve interviewed women who left six-figure corporate careers to start their co-hosting business because what they wanted wasn’t a massive portfolio, it was flexibility. I’ve interviewed women who just wanted enough extra money to take their grandkids to Disney every year. Others wanted generational wealth. Others wanted to retire their husbands. Others simply wanted to prove to themselves that they could build something meaningful.

And none of these dreams are more valuable than the others. They’re just different.

And I think that’s one of the greatest gifts this industry gives us. There is not one definition of success. You get to decide.

I think we spend far too much time looking sideways. We scroll social media, and suddenly we’re convinced we need another property. Someone launches a co-hosting business, and we wonder if we should do that too. Someone buys in a completely different market, and then we question our own. Someone scales to twenty or thirty properties, and suddenly the business we were proud of yesterday doesn’t seem big enough anymore.

Comparison has a way of quietly stealing contentment.

But after two hundred conversations, I can tell you something I’ve never forgotten. The women I admire most aren’t the ones with the biggest businesses. They’re the women whose businesses support the lives they truly wanna live.

Because at the end of the day, your business exists to serve your life. Your life doesn’t exist to serve your business.

That means your version of success might look completely different than mine, and that’s not only okay, it’s exactly how it should be.

Maybe success for you is replacing your teaching income. Maybe it’s creating enough financial freedom to work fewer hours. Maybe it’s being able to attend every one of your kids’ soccer games without worrying about asking for time off. Maybe it’s traveling more. Maybe it’s creating a legacy for your family. Maybe it’s finally believing that you can do something you never thought possible.

Whatever it is, own it, protect it, build toward it, because the goal isn’t to build the biggest business. The goal is to build a business that gives you the freedom to live the life you’ve been dreaming about.

And I think that’s what every one of these two hundred women have taught me. The happiest entrepreneurs aren’t chasing someone else’s finish line. They’re building lives that feel deeply aligned with their own values, priorities, and dreams.

And maybe that’s the lesson you needed today.

Lesson number three: information doesn’t change lives, people do.

If there’s one lesson that surprised me more than any other over the last 200 episodes, it’s this: success has very little to do with how much information you have.

Now, I know that probably sounds very strange coming from someone who hosts a podcast. Because let’s be honest, I love learning. I love books. I love podcasts. I love YouTube. I love interviewing incredible entrepreneurs and discovering how they think.

Learning matters. Information matters. But after 200 conversations, I’ve realized something: information alone doesn’t change lives, other people do.

You know what’s interesting? I’ve interviewed women who’ve never listened to a podcast before buying their first property, and I’ve interviewed women who could probably teach a master class on short-term rentals because they spent years consuming content.

Do you know what these two women had in common? Neither one succeeded because of how much they knew. They succeeded because they kept moving, and almost every single one of them had people helping them move.

Maybe it was a mentor, maybe it was another host, maybe it was a mastermind. Maybe it was a group of women who simply reminded them, “You’ve got this.” Whatever it looked like, they weren’t trying to build something meaningful completely alone.

And I think that’s where so many people quietly get stuck. We convince ourselves that if we just listen to one more podcast, watch one more YouTube video, read one more book, we’ll finally feel confident enough to begin.

But again, confidence rarely comes from consuming. Confidence comes from doing. And doing is so much easier when someone is walking beside you.

One of my favorite parts of hosting this podcast has never been recording the interviews. It’s what happens afterward. It’s the emails from listeners who tell me they finally made an offer on a property. It’s the messages that say, “I never thought I could do this until I heard her story.” It’s watching the women who once introduced themselves by saying, “I’m just thinking about getting started,” become women who say, “I just bought my second property,” or, “I left my corporate job,” or, “I hosted my first guest this weekend.”

Do you know what changed? It wasn’t that they suddenly discovered some magical strategy no one else knew. And it wasn’t that they became fearless all of a sudden. It wasn’t even that they became experts overnight. They simply stopped trying to become successful in isolation.

I’ve often said that proximity matters. When you’re surrounded by people who are asking bigger questions, solving bigger problems, celebrating each other’s wins, picking up each other after disappointments, something begins to change inside of you. You start believing bigger things are possible for your own life. Not because someone hands you success, but because they remind you that you’re capable of creating it.

I think that’s why community is so powerful. It doesn’t just give you answers, it gives you courage. It gives you perspective. It gives you accountability. It gives you the people who celebrate your victories because they know exactly how hard you worked to earn them. And on the days you start doubting yourself, it gives you someone else’s belief to borrow until your own confidence catches up.

Looking back on 200 episodes, I don’t think the women who built extraordinary lives had extraordinary amounts of information. I think they had extraordinary support. People who challenge them, people who encourage them, people who reminded them that they were capable of more than they believed.

And maybe that’s why you’re listening today. Maybe what you need isn’t another podcast. Maybe you’ve learned enough. Maybe what you’ve been missing isn’t information at all. Maybe you’ve simply been trying to build your dream by yourself.

And if that’s true, can I encourage you with something? You were never meant to. Because businesses grow faster, dreams grow bigger, and confidence grows stronger when women choose to grow together.

And maybe that’s the lesson you needed today.

Lesson number four: build a business that gives you your life back.

The last lesson I wanna leave you with today is probably the one that’s become the most important to me. Your business should support your life. It should never replace it.

It’s interesting because when most of us get into short-term rentals, we say we’re chasing freedom. We want more flexibility, more time with our families, more financial security, more choices.

We don’t start this journey because we dream of answering guest messages at midnight, and we don’t dream about spending every vacation checking our booking calendar. We don’t dream about feeling guilty every time we step away from our phones. We dream about creating a life with more margin, more presence, more possibility.

But somewhere along the way, something subtle happens. Without even realizing it, we stop building a business to create freedom, and we start building a business that quietly steals it.

I’ve experienced seasons of that in my own life. Maybe you have too. The business grows, the opportunities multiply, the responsibilities increase, and before long, you’re serving the business more than it’s serving you.

That’s one of the reasons I’ve become so passionate about systems over the years. Not because I love checklists and not because I enjoy organization, but because systems create freedom.

Every system is really a decision you’ve made once, so you don’t have to keep making it again. Every process, it removes a little bit of mental clutter. Every team member you empower creates a little more space. Every responsibility you delegate creates room for something that matters even more.

And after 200 conversations, I’ve realized something else. The women I admire most aren’t the women with the biggest portfolios. They aren’t the women making the most money. They’re the women who never forgot why they started.

Some built one incredible property that pays for family vacations every year. Some built businesses that allowed them to leave corporate jobs they no longer loved. Some created generational wealth. Some built companies that gave them the flexibility to be present for every school program, every soccer game, every family dinner.

Not one of those dreams look exactly alike, but every one of them is success, because success is not measured by how much you’ve built. It’s measured by whether what you’ve built gives you the life you were hoping for in the first place.

And as I’ve been reflecting on 200 episodes and another birthday, if I’m being honest, I’ve realized my own definition of success has changed too.

Ten years ago, I probably would have measured success by bigger numbers. Today, I still love building businesses. I still love short-term rentals. I still love dreaming big. I still get excited about new ideas.

But I’ve learned that the greatest wealth isn’t just financial, it’s having the freedom to decide how I spend a Tuesday afternoon. It’s being fully present with the people I love. It’s having margin to mentor women who are building something meaningful. It’s knowing that the businesses I’ve built support the life I want instead of competing with it.

And I hope that’s what you remember long after this episode is over. Not how many properties someone else owns, not how much revenue someone else makes, not how perfectly someone else’s business looks on Instagram. I hope you remember why you started.

Because maybe your dream isn’t really about short-term rentals. Maybe it never was. Maybe your dream has always been about freedom, about choices, about creating opportunities for your family, about proving to yourself that you’re capable of more than you once believed.

And if that’s true, then don’t lose sight of that dream. Build the business. Absolutely. Learn, grow, take risks. Surround yourself with incredible people. But never forget that the business is the vehicle. The life you’re creating is the destination.

Because after 200 conversations with ordinary women building extraordinary lives, this is what I know for sure. The women who inspire me most aren’t the ones who built the biggest businesses. They’re the women who had the courage to build businesses that honored the lives they wanted to live.

Thank you for spending these last 200 episodes with me. Whether you’ve been here since the beginning or this is your first episode you’ve ever listened to, thank you for trusting me with your time. Thank you for letting me be a part of your morning walks, your road trips, your turnovers, your dreams.

And if I could leave you with just one final thought, it would be this: You don’t have to have everything figured out before you begin. You don’t have to become someone else before you deserve success. You don’t have to build the biggest business to build a beautiful life. You simply have to take the next step, because somewhere out there is a future version of you.

She’s more confident. She’s more courageous. She’s surrounded by women who believe in her. She’s built something she’s incredibly proud of.

And here’s the beautiful part. She isn’t waiting for you to become someone different. She’s simply waiting for you to begin.

Here’s to the next 200 episodes. Here’s to the extraordinary women I’ll have the privilege of meeting. And most of all, here’s to the extraordinary life you’re capable of building.

I’ll see you next week.

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