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If I’ve said this once, I’ve said it a million times. You can’t run an STR business successfully on your own. You need a lot of support from a lot of different directions.

Finding support is what will take you from an STR hobby to an STR business.

And, by support, I don’t just mean the people you hire for your team. I mean the people who are there for YOU, helping you see your potential, sharing their wisdom, giving you encouragement, inspiring you, teaching you, and helping you be the absolute best you can be.

In a nutshell, you need:

  • A community.
  • A mentor.
  • Experts.


Let’s break that down.

#1: Surround yourself with a supportive community.


This community can look like a lot of different things, based on what you feel you need most.

Maybe it’s a group of other STR business owners. A place where you all gather—in real life or virtually—to help each other, learn from each other, share your experiences, and grow your businesses.

Maybe it’s a group of business people from all industries, and you network and help each other out. You point your clients to them, and they point their clients to you.

We’ve built a great community on the Cashflow Diary Facebook page. It’s a great way to interact with like-minded people, bounce ideas off of each other, watch videos together, and get your questions answered.

I’m really proud of our community. We’ve learned from each other, rallied around each other, celebrated each other’s successes, and helped people achieve their biggest dreams.


#2: Find a wise and experienced mentor.


I know what you’re thinking. Do I reeeeally need a mentor?

YES, you do. You need a mentor. You need someone who has already been there, done that.

The perfect mentor is someone who has achieved a level of success that you can only dream of. They are already at the spot that you want to be.

And they’re willing to share their advice and wisdom with you to help you get there, too.

You can bet that, if they’ve achieved a high level of success, then they’ve made a lot of mistakes. They can help you avoid making those same mistakes. You can learn from how they messed up without taking the field trip yourself.

But a good mentor doesn’t just hand you all the answers. They don’t just give you a cheat sheet, so you don’t have to put any work in. They’re also going to encourage you to solve problems on your own (with them by your side).

Your mentor needs to be someone you can trust. You trust their personal character, and you trust that they’re going to give you sound advice.

This person is someone you can bounce ideas off of, someone you can call with questions and concerns. Someone who will help you know you’re not alone.

What kind of traits should you look for in a mentor?

Someone who is always learning and growing. Someone who is patient and a good teacher. Someone who is available and willing to help.

So, is this a working relationship, a paid position? Does someone just volunteer to be your mentor for free, or do you pay them?

I’d say that, most of the time, this is someone you pay for their help and service to you. They took a lot of time (and probably invested a lot of money) to become an expert. They deserve to be paid for their expertise, knowledge, advice, and time.

An exception to this would be if part of their giving-back initiative is paying it forward, offering mentoring services pro bono. But don’t ask for or expect that.

Another exception would be if you barter something for their mentoring services. What do you have that they need or want that you could offer them in exchange? Do you have a skill that could be useful to them?

Or maybe an STR they could use for free as a vacation rental?

Be creative. Think outside the box. But compensating someone for their emotional labor is really important.


#3: Learn from the experts.


You don’t need an actual in-real-life human person to teach you everything you should know. A world of knowledge is right there, literally at your fingertips.

You can hop on your laptop, type something in the Google search bar, and learn and learn until your brain feels fried. Then take a break and learn some more.

Believe me, knowledge acquisition can be addicting.

In the best kind of way.

And there you have it. Find a community. Find a mentor. And learn from a whole host of experts who know what you need to succeed.

The version of the person who is here today needs an upgrade in order to receive, experience, and witness the things you say you want.

And you can’t do it alone. These people will help you get there.

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