Connecting with your guest as a remote superhost with Tammi Sims

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This week we’re celebrating Thanksgiving here in the good old US of A… Many, many… I mean many, years ago, I hosted a Pre-Thanksgiving dinner… What? Is it a trial recipe run? Is it like a rehearsal dinner? Well, No, and No… Let me explain a little bit of the origin.

Here in the BIG apple, many of us are transplants, you know, from all over the place… Most of my dear friends would go back home during the holidays to be with their family and old town friends. Those of us who lived here had our own family dinners. Bottom line was, I wanted to have a special gathering with my friends, too. You know, to be together before everyone went off to their official family commitments.

So I decided, kind of on a whim, to host a Pre-Thanksgiving Dinner… I mean a real Thanksgiving dinner with all the trimmings… Pot-Luck Style! Don’t let the Pot-Luck fool you. This was an all out, sit-down with all trappings, dinner… Well, It was a hit! A huge hit!

I found out later it’s called Friendsgiving, yes other folks do it as well, I’m not that original. But suddenly, every year my friends would start asking about Pre-Thanksgiving dinner… And with that… a tradition was born.

15 Years Later…

Now 15 years later, every Saturday before official Turkey Day, my friends, and now even some of my family members, come over to enjoy the festivities… Each person makes one special dish. Usually, it’s a dish they love to make…. Or are good at making….and Believe me, these folks go all out. They take Pot-Luck to another level! It’s amazing and just so much fun!

The truth about this tradition and its appeal is … It’s mainly just us friends. We ALL can be ourselves without any of that family filter… You know. Is crazy Auntie Doris coming? Is Uncle John drinking again? Is Cousin Sara talking to me? It’s just let your hair down, and let loose! It’s very JFZ… No, not Jay-Z! I wish… But JFZ… Judgement Free Zone.

The good thing, I confess, is that most of my friends are foodies. One is even a chef. Another of my good friends owns the food company City Saucery. If you follow me on Instagram, you have seen me peddling their sauces at food fairs and special events. I confess I do get a bit intimidated cooking for them, but I do have a couple of dishes where I can hold my own. My flan always requested. Besides… JFZ, no judgment remember?

During dinner, we usually talk about what we are ALL grateful. We reflect on the past year and what’s been going on… and NO, I don’t let them cop out with, “I’m thankful for this gathering, the good food, and Evelyn for setting it up.” Oh, NOOO! You have to dig deep.

Deep, my friends!

Of course, they do the same to me… I know I have to talk about what I am truly grateful for, which is plenty. This year, I’ve even been thinking about my life as an Airbnb host… So it gets a bit quiet with everyone listening… and sometimes some tears… It’s the only time the dinner table is silent, and we just support each other. It’s great to have this group of friends every year…

Our tradition.

Living an Airbnb Life:

In the opening of this podcast, or on my website, blog, webinars, you always hear, or see in my intro, that I’ve been living an Airbnb life since 2010… and you might wonder, what does that mean?

On Episode 1, My Personal Hosting Journey, I shared my story of why I started Airbnbing and what it meant to me to find this business of the sharing economy and sharing my home with… for lack of a better word, strangers.

But NOW I want to talk about why I continue to host, how my life has changed, what’s good and not great about it, especially since I’ve been living with guests for over 7 years.

You might know from my other episodes or from reading my literature that I make six figures a year as a host, and that might give you some idea of a luxurious, glamorous life, jet-setting around the globe…

And I do travel to speak at conferences and an occasional vacation but there isn’t jet-setting like you’re thinking. For now, I’m still here in Brooklyn where I wake up, working and working hard to be successful.

If you are a host or thinking about Airbnbing, I want you to start with your eyes wide open because many people think it’s just hosting, 1,2,3 and cha-ching…

Those folks usually fail…

Hosting can, and has been, an amazing and successful ride for me… and with the right tools and guidance, you can find that success, too….

And that’s my goal, my purpose for doing all of this… This podcast, my website, the Facebook Group… Offering my House Manual…. It’s all geared to arm you guys with as many tools as possible to find that success… without all the trials and errors I’ve gone through. So, with all that being said… Let’s talk about…

“The Pros & Cons of Living an Airbnb Life since 2010”

The First Guest:

When my first Airbnb guest walked through my door in May of 2010, I never thought this would become my new life and career … But hey, here I am, and I’m doing well. Seven years and counting, with over 600 reviews under my belt and … I’m still living with strangers.

To be honest, I hesitated for many years before I realized and came to terms with the fact that this was my new full-time job. It was difficult because it was NEVER part of my plan… I did mention living with strangers!

Well, before we start with the cons, cause that sounds a bit negative…. let’s start with the positive. ALWAYS the positive… Let’s first talk about the pros of living an Airbnb life.



Freedom of time:

I don’t have a nine to five job. I don’t have to hear that amazing alarm go off at 6am, rush to shower, get dressed, dart out my door to make that train in order to be on-time… There is no boss! That one alone is the biggest PRO! There isn’t that pressure of time over me.

Yes, I need to have the space ready for guests to check-in. And yes, there have been sometimes when I’m wrapping up the vacuum cord as guests are ringing my front doorbell. For the most part, once my guests check in, I’m off and they’re on their own. There isn’t a lot of hand-holding or having to do things with them or for them.

The day is more about answering emails, inquiries, a maintenance issue… and perhaps that rare emergency. Guests get locked out, lost, etc.

Sometimes it can feel like you’re working 24 hours non-stop, not your nine to five gig…. but there is that imaginary freedom of time. Imaginary freedom… Wait, do I need to move this to a Con?

Nope, I’m keeping it PRO because I do believe I have the freedom of my OWN Time.

For example, this year I’ve had some health challenges, and I was able to set up my doctors appointments around my guests' check-in and booked dates. If I had a traditional job, I would’ve exhausted all of my vacation days, all of my sick days… and feared that I’d be let go. Or worse, have my colleagues think I was making excuses and being lazy… The horror!

Hosting allowed me to take care of myself. I was able to make my appointments without any worries.

Yes, freedom of time stays Pro.

Passive Income? Maybe, maybe not:

Some people can see Airbnb as passive income. What is Passive income? According to the Financial dictionary, you collect passive income from certain businesses in which you aren't an active participant.

This might include limited partnerships where you're a limited partner, rental real estate that you own but don't manage, and other operations in which you're an investor but have a hands-off relationship. Love me some passive income!

And you can do this with Airbnb. I just recorded an episode with Metro Butler property service company, which will manage the business for you, and we discussed how you can select one. You don’t need to do a thing, just collect the money. Totally passive income.

There are other hosts, like me, who are more hands-on, and we don’t have a fully passive income business. But I also see part of my income as passive, since the house is generating income and I’m not actively working on it. At least, not all the time.

Interesting People:

I have had some amazing guests. Very interesting people who I know I would never have had the luck or opportunity to encounter, if not for Airbnb. My first guest was a Professor of Innovation. So impressive and different. A Professor of Innovation and me chatting…. Some of my guests have even become friends. That’s a BIG PRO!

One of my guests became my primary physician. Yes, my doctor. How amazing is that? Her house had a gas leak this past winter, and she stayed in my home with her family. I have a gas leak to thank for my doctor… and I love her.

I actually know of hosts who are engaged to former guests. Hey, when it’s love, it’s love, right? Judgement Free Zone!

Have I loved every guest that has knocked on my door? No, of course not. There are guests that I love to see go. And I mean to go, go away, and please do NOT return…But for the most part, I have enjoyed my guests.

Using My Own Asset:

In my case, I already had my house. I didn’t buy or rent a new property to start Airbnb. I moved from my original bedroom to my second bedroom. And I have stayed there….. I like that no part of my home is wasted.

Financial Freedom:

I created an income where there wasn’t one. At least, I didn’t think there was… ‘til Airbnb.

And it created the next pro…

New Career:

Before Airbnb, I had never even stayed at a bed and breakfast. Never crossed my mind. Yes, I was a hotel snob… I mean, person. Hotel person. I worked in Advertising for over 20 years. I knew nothing about the sharing economy or hospitality.

Now, I have a whole new set of skills, from stain removal expert to marketing to human resources, and so much more. Hosting has expanded my world in more ways that I would never have anticipated.

In addition, I created the hosting journey, which is a totally different business. Hey, I even have a podcast, who knew. But again, a business I would have NEVER have thought of if not for becoming an Airbnb host.

I left the biggest pro for last.

Gratitude from Guests:

One of the things I noticed immediately was the gratitude some guests share the experience I provide. It’s not just for space but for the welcoming feeling of home. A feeling you don’t get when you check in at a hotel… Trust me, I know. Like I said, I was a Hotel… Person.

My guests are genuinely happy to be in my home. They appreciate the effort that I have put into making them feel comfortable and safe away in their home away home.

I just did a production job a couple of months ago…. Sometimes I dabble in my old career…, and I must say, I felt there was this lack of appreciation. Not just with me, but straight across the board… I’m sure I had felt it before, but it was my job then, and I had no other reference… It came down from the Director, no matter what was done, it just wasn’t enough. There wasn’t even a “Thank you.” Nothing! I get it, we’re doing our job and our paycheck is our thanks, but really? Not even a word of gratitude. Those 2 words ‘would have gone such a long way.

You know, when you’re working 20 hour days and you’re making miracles happen, yes, miracles happen…, a simple THANK YOU, would have gone such a long way. More than money. Well, maybe not more than money, but you know what I’m saying… It’s showing some appreciation in order for everyone to be truly productive.

Guests, you see, show it. They tell you how much they appreciate the unexpected breakfast items you’ve provided, the extra touches you’ve created, the well thought out House Manual that gets them to where they want to go. They know you’re going that extra mile, and they tell you… Sometimes, they even show you… With a note, a gift, or a glowing review.… Touching stuff that makes you want to do it again and again…

No matter how hard or unnecessary one might feel it is… It’s noticed. It’s appreciated.

Of course, not everything is a rose garden, and like always, I’m here to tell you the good, the bad, and yes, the ugly.

Let’s go to the CONS:

Freedom of time:

But not really. Unless you have that management company taking care of your business or a self-check-in process with lock-box or keyless locks, you’re going to spend a lot of time waiting for your guests. A lot of wasted time.

Not all guests communicate well… I used to spend many hours and even cancel plans waiting for guests to show up. I hesitated to purchase the lockbox… I wasn’t embracing the NEW way of hosting… I finally did purchase a the lockbox… and that lockbox gave me freedom. Like I mentioned in episode 19: Technology Made Easy For Your Airbnb to get your freedom back, my dears, sometimes we have to embrace the unknown.

Living with People:

If you’re living with guests, well, you’re living with people. Strangers. Sometimes they won’t understand boundaries or your boundaries… And they will eat your avocado. They’ll go to your designated food shelf and just eat your avocado… How I suffer.

All I can say is, you better have a good set of House Rules and Boundaries, if you want a way to start listen to episode 04 He Ate My Avocado: Setting up House Rules and Boundaries

because as much as I like my guests, sometimes they will SOMETIMES think that your House Rules don’t apply to them and push back…. but that doesn’t mean you have to give in to them. Just be firm but polite, and remember…

“No” is a complete sentence. Don’t you just love that?


Tied up with political policy differences, seasonal changes, or legalities from the City? There are a few cons about finance, so I’m dividing this one up.

Oversaturation of the market: Lots of people are doing Airbnb, which means prices are sometimes going down, down, down. You have to decide if hosting is still worth it. Only you will have that answer. If it costs you the same as a longterm tenant, you might reconsider your Airbnb status because you have to include your time in your cost calculation.

A ceiling of money: if you were to only have or stay with the one listing, you can only make so much money. I’m sorry to tell you, there are only so many days in a year, and you’ll need another resource or plan in order for it to grow… You’ll need to get another listing, increase your price per night, or upsell. By upselling, I mean to offer something extra like tours, cooking classes, etc.

Tied to political, weather, and legal issues: Yes, your business will be affected by politics, legal issues, and weather. The reality is that the city can change the law and change your business. Simple as that. Even worse, they can make it illegal to Airbnb. Period.. Right now in NY, the city has an aggressive campaign against hosts. In Vancouver, they just passed a new law with major restraints on hosts.

You also have the weather, which can destroy your business. You need to plan for it. You can listen to Episode 23: “Rebuilding an Island Paradise – The Crispin and Jennifer story” how two hosts are rebuilding their dreams after Hurricane Maria destroyed their two Airbnb cottages in Dominica.

So! There you have my PROS and CONS for living an Airbnb life.

I know some are the same side of the coin, but that’s how I see it. Life is not always black and white; there are different shades of grey. Not that kind of grey.

It’s also about gratitude. Like what we do at my Pre-Thanksgiving dinner… We take a moment… Just a moment. It’s about acknowledging that many of us have the ability to work, make some money, and enjoy our lives hosting… It’s the freedom to set our own rules….

I know Airbnb life is not perfect; that’s why I’ve called this episode “The PROS and CONS of Airbnb Life” rather than “The Utopian Experience of an Airbnb Life.”

The Facebook Group Opinion:

I asked the community of my Facebook Group The Hosting Journey their own Pros and Cons, and these are a few of their answers:

For Darlene who is a live-in host: a pro-is, never being alone. And a con: more and more stories of Airbnb siding with guests or canceling accounts. That’s a big one.

Jim mentioned: A pro-is able to travel in the low season or during long-term guest stays.

A con: he is also a live-in host and on a tourist route. he does one night stays in the high season, so he rarely gets days off as there is always laundry, change over, and waiting for guests.

Kathleen’s pro is to use her home to produce income and interacting with guests. A con is that her cell phone is like a beeper, which reminds her of her previous life.

Perhaps you have other pros or cons?

I know of some hosts in the Facebook group, who moved to long-term tenants. They didn’t want to bother with the cleaning, communication, and felt the money they were making wasn’t that much to be in the Airbnb business.

Remember, you need to decide what kind of life you want to create and live… and not just financially. You also need to consider your time and mental space. Two very important line items…

Your Future?

In a year from now, where do you see yourself?

What does 2018 have in store? I’m working on my plan. But as long as hosting is a financially viable business. I will continue Airbnbing and meeting amazing guests.

And continue to be grateful… Grateful to my family, friends, guests… and YOU, my dear listeners.

Your host,



Some of the links mentioned are affiliate links. if you choose to make a purchase, I may earn a commission. Commissions come at no additional cost to you.

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