Michael Hamilton’s 5 Keys to Succeed as an Airbnb and Vacation Rental Owner

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Summary of Michael Hamilton’s 5 Keys to Succeed as an Airbnb and Vacation Rental Owner

  • “Don’t Get Trapped by Dogma.”  – Steve Jobs
  • Invest in Your Companies’ Greatest Asset: YOU.  Who cares more about your results and business than you?
  • Control Your Emotional State. One of the hardest to achieve.
  • Be Resourceful! (The truth is it is not YOUR resources that matter but how resourceful you are!)
  • Apply The “E” Myth Principle to Short Term Rentals.  It is a lot more fun to work “on” a business than get stuck working “in” a business

Rad News & Opportunities!

  1.  Updated & New Content: Vacation Rental Dojo, Mike & Maria’s Free online vacation rental learning center 
  2. Vacation Rental Confidential, Our Book:  VRC is a quick showcase of the Live Swell Story & Proven Biz Model Download Chapters 1 & 2 Free, Our Gift to You 
  3. Exclusive NEW Release:   Live Swell’s Sparkling Clean Training & Certification Program

Have you ever thought about growing your Airbnb or Vacation Rental Business?  Imagined if you could live off your rental income and be your own boss?  What would be the keys to succeed?

Most owners, unfortunately, tend to endure the typical challenges of vacation rental ownership.   They can feel stressed, overwhelmed and soon thereafter they may get “stuck” working in the rental business. When the owner is stuck they will likely fail to grow or decide to quit and sell.  For other to-be owners, however, the dream of owning an Airbnb or Vacation Rental can remains just that, what a bummer!  What if they had the confidence to get started?

Like you, I’m not immune, I have gotten the negative review, I have had to fire and re-hire cleaning staff, I’ve gotten the maintenance call to pull a sweet potato out of the clogged toilet bowl and I have felt what it feels like to deal with a complaining guest – our customers.  Like all professionally run businesses, this one is not easy, but it is a simple business.

After hosting 1000’s of guests in multiple properties and markets, our Vacation Rental Business Model continues to produce high level results and grow.  Seeing how active our vacation rentals are, many people, including guests, friends, investors and other vacation rental owners have asked me, “What are your keys to Airbnb success?” My response is typically, “Thats a great question, but its a pretty loaded one, unfortunately, I don’t have a simple answer.”

What I have found is that success is in the eye of the beholder;

  • Many owners are satisfied with one vacation rental
  • Few build multimillion dollar income machines
  • Some earn enough to cover their mortgage or just get by
  • Others could care less

Getting started, I did not know much but I knew no one was going to get rich from one lonely vacation rental property, I did not want a business that consumed all my time and “just covering the mortgage” was not going to cut it. My goals were in alignment with building a multimillion dollar portfolio of income producing cash machines aka vacation rentals.

In 2018 I decided to get our ideas, guiding principles and “playbook” on paper. So, as you may know, I wrote a book, Vacation Rental Confidential.  The goal of VRC was simple, make a contribution to the vacation rental space, so that others, whether, ahead or coming behind, can use our experience as a resource.

In this short post I have put together my 5 Keys to Succeed as an Airbnb or Vacation Rental Owner.

Disclaimer:  My keys to succeed are based off of my goals (yours may be different and that is OK).  I wanted to build a “system dependent” and scalable business that could be run from anywhere.   I wanted it to produce enough income to have the option to leave a 6 figure+ full time job. What I did NOT desire was getting “stuck” working in the business as a landlord.  I wanted to build wealth, have retirement security for myself and the ones I love.  I wanted MORE OPTIONS in life! 

#5 Key to Succeed as an Airbnb + Vacation Rental Owner

Apply the “E” Myth Principle to Short Term Rentals

What is the “E” Myth?  The “E” Myth, is a hit business book by business consultant, Michael Gerber, which means the “Entrepreneurs Myth.” Gerber coined the term the “E” Myth as he observed a disappointing phenomena:  most who strive to start businesses or build income producing assets, like vacation rentals, unfortunately get “stuck” working in the business and fail.  

E Myth Vacation Rental Dojo

I, like Gerber,  believe that the entrepreneurs’ and business owners’ responsibility is (1) to create the platform and systems for technicians and managers to be the most effective in their role and (2) to provide training and development.  In this way our business and team has the highest probability for success.

Gerber stresses the importance of documenting everything. In fact, he states, “build you’r business as if one day you were going to sell it.” Documenting everything in your business creates magic! If someone desires a consistent predictable result, let’s say five-star reviews, the best choice is to document the process of getting consistent 5 star reviews so it is executed the same way over and over.

Reproducible Systems = Predicable Results 

To ultimately move from a technician to a manager to an entrepreneur, one has to get comfortable with “letting go of the vine” or, said differently, “firing oneself.” In extreme cases, some business owners just have to let go of their egos. The reality is that well-trained people can do things just as well or better. Once the right individual is empowered, a business owner will have effectively off-loaded a significant chunk of labor in exchange for TIME—a fair trade for the entrepreneur that wants to grow and not get stuck in the business.  Do you know how may hours there are in one whole week? If not get to “know thy time,” the most successful entrepreneurs are extremely intentional about their TIME – your only non-renewable resource.

Lastly, it’s important to mention that a person can be both a technician and an entrepreneur. For example, they may be the entrepreneur in their vacation rental business and a technician working in as a civil servant or manager. It’s not an either or, and most successful business people transition smoothly out of technician roles if that is the direction in which they desire to go. That’s what we did.

#4 Key to Succeed as an Airbnb + Vacation Rental Owner

Be Resourceful!

I’m going to be honest, not gentle:  For every person with a lame excuse regarding why they “can’t” do something, I have met ten other people with a tougher story that is achieving their goals and getting shit done!

Many people fall victim to self-sabotage and will find any reason as to why they can’t achieve a goal or result.  “I don’t have enough time,” “I don’t have the money,” “What if X happens?”

Entrepreneurs will always experience a “lack” of something, but this is what they do, they become resourceful and figure out solutions, that is their job and responsibility.

How can an Airbnb and VR Owner be more resourceful?  You are right now, reading these words, leveraging (and learning) from my experience.  Modeling success is key.  Follow and engage people who have results you like or desire.  Work toward a Growth Mindset — they kind that seeks solutions and does not take things for granted or as they are .  I recommend Carol Dweck’s Book, Mindset.

#3 Key to Succeed as an Airbnb + Vacation Rental Owner

Control Your Emotional State

Ever, “fly off the handle?” If not, you probably know someone who does from time to time.  This is normal, we are human and there are triggers and stimulus that can put a person into a high emotional state, both good and bad.

This is important in this business as there is a lot of excitement and sometimes disappointment!  There is rejection, fear, disagreement, big wins, large direct deposits and decisions that ultimately need to be made. For example, I work with my partner Maria, we are basically married — but not officially, yet, but will be soon.  We frequently discuss many topics around our vacation rental business to improve it.  Sometimes, I hear Maria’s idea and have a negative trigger — its not the solution I had in mind — the trigger is often times for the wrong reason or due to my personal selective hearing.  I’m not perfect and I’m still learning yet getting this wrong has tough consequences.

Being raised as a New Yorker, it was common to witness road rage daily.  I remember, my grandfather being cut off by a driver on a country highway, grabbing a Charleston Chew candy out of my mouth mid-bite, pulling up to the driver side of the other car and throwing the remaining bar at the driver, while spewing off some strong profanity, heavy with F-bombs.  Everything turned out OK and I got though the situation unscathed, however, emotional states like this can lead to unnecessary accidents, for example.

Looking back, the inability to control my emotional state earlier in life may have impacted my promising athletics career.  The point here is don’t let little petty nonsense become a distraction in the bigger picture.

There are many ways to learn to control the emotional state.  First is to become mindful of when negative emotional states pop up.

Many people have found great success in different ways including, Tony Robbins Trainings, Meditation, Yoga and Anger Management programs (Charlie Sheen seem to have a reputable group!).  Personally, I have found, though Meditation and Yoga, “detachment” to be effective in helping me control my emotional state better.  I still have a lot of work to do but have found that stoicism can be a competitive advantage.

#2 Key to Succeed as an Airbnb + Vacation Rental Owner

Invest In Your Company’s Greatest Asset: YOU!

As a vacation rental or short term rental owner and host, you are your company’s greatest asset.  Ultimately, you make the calls on which direction the ship is headed.

The sharper your axe and the more tools you have at your disposal the stronger you can pursue your mission.  Get educated, be resourceful and lead well because there is no one that cares about the success and longevity of your company more than you.  Though the first 4 years of operating Live Swell Beach Bungalows we had never taken a dollar of our profit out of our businesses. Why? we have reinvested all these funds into our business and education to make it better and better, for ourselves, our people and our guests.

My feeling is that the top performing hosts — the ones with the opportunity to scale and continually increase income — are perpetual students of the business.  Industry leaders realize that rarely does any top performer pop out of the womb with essential skill sets,  business acumen and financial literacy.  

If a person desires more, they must become more.  I would recommend strengthening skill sets in the following areas specifically:

Evaluation; as an entrepreneur we are constantly evaluating things — much more frequently than most people are — we are evaluating, people, business opportunities, products and your next vacation rental.  Make sure you know your OPEX!  Thats short for Operating Expenses and the ugly side of the vacation rental business.

Marketing; Marketing is the lifeblood of any business – non-effective marketing simply means lost opportunity and more work.  Your ability to influence, create desire, lower walls of “booking resistance,” and manage expectations are a few of the key areas to master.  For our internal team we created a “Booking Conversion Blueprint,” our easy to use system that has resulted in top ranked Airbnb’s in our marketplace.

Financing Options; Without financing, Airbnb and vacation rental ownership is sadly a pipe dream.  The world of financing short term rentals is evolving, yet slowly.  Nevertheless, there are many strategies to acquire a short term rental property with both traditional and “creative financing.”  Know your financing options and realize that an individual with a financial education has more options that the person who does not!

Ultimately, lack of CONFIDENCE is what holds most people back form participating or from getting the next deal.  The stronger a person’s business and financial education, the more CONFIDENCE and OPPORTUNITY they will have.  

#1 Key to Succeed as an Airbnb + Vacation Rental Owner

Don’t Get Trapped by Dogma” – Steve Jobs

In his memorable commencement speech at Stanford Steve Jobs,  boldly stated to the audience, Don’t get trapped by dogma…”  Jobs was communicating the idea of being very cautious in accepting traditional beliefs that are taught as “undeniable truths.” He was encouraging us all to challenge the so-called normal, widely held beliefs and traditional thinking (a.k.a. the status quo). Apple’s motto is Think Different.

What is Dogma? A principle or set of principles laid down by an authority as incontrovertibly true.

Enjoy this short story:

On a beautiful sunny Thanksgiving Day, the women of a family of four generations strong are preparing a juicy ham. As things are moving along, the youngest daughter of nine years old observes her mom cut off the end of the ham and throw it in the trash. The daughter curiously asks, “Mom, why did you cut off the end of the ham?” Her mother replies, “It’s a tradition. Your grandmother taught me to cut off the end of the ham because it allows the juices to flow and it tastes better.” So the young girl proceeds to ask her grandma, “Grandma, why does cutting off the end of the ham makes it taste better?” Her grandma replies, “I’m not really sure. It’s what my mother taught me to do and how we have prepared the ham every year. It’s a family tradition.” So the girl finds her great-grandmother taking a nap in the den, shakes her to wake and asks, “Great-Grandma, why does cutting off the end of the ham make it taste better?” Startled and a bit confused as to the question, Great-Grandma replies, “I cut off the end of the ham because it was too big to fit my square pan. That’s the reason; it doesn’t make it taste better.” The young girl looks dumbfounded and says, “Really?”

Be careful of confusing “tradition” with “truth.”  Just because we are taught something does not mean it is true.  True intelligence lies in the ability to observe multiple perspectives and choose which is right for yourself.  Choose wisely.

If you have enjoyed this post, please share it with someone who may benefit.  

Related Content:

Owning a Vacation Rental 101: Biggest Lessons Learned (Toilet Bowls?)

How to Build Wealth With Vacation Rental Homes

Podcasts Featuring Live Swell Founders Mike and Maria

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