Matt Landau
  • Founder, VRMB

Play it safe or take the chance?

I just finished Dan Pink's The Power of Regret -- all about turning negative emotions into positive actionable lessons -- and the book includes this, one of my favorite quotes:

By understanding what people regret the most, we can understand what they value the most.

The book explains how "boldness" regrets ("things I didn't do") were almost 2x as common as action regrets (things I did).

And I couldn't help but apply it to the vacation rental movement: where a once-in-a-lifetime alignment of stars is literally SCREAMING at us to take risks, follow our instincts, and try things that have never been done before. The instinct is that when times are good, there's less pressure to pull the trigger. But actually, when times are good is EXACTLY when you want to step on the gas and make calculated gambles.

REQUESTS
- Share one regret and what it suggests you value?
- Share one idea you'd like to try (at least once) using your vacation rental business as a lever to achieve it?

A confluence of your experience, market conditions, and other bold risk-takers here in the community may nudge you along!
 
Regret-not finishing college. I didn’t want to end up financially in debt for the rest of my life. I watched and experienced my parents go through bankruptcy and this formed in me a strong desire for financial stability. (something I value).

I’m already working on one idea I’ve had since opening our doors at one of our locations that draws a lot of bachelorettes. I’ve joined forces with a friend who is an event planner and we are hoping to create discount packages & itineraries for our bachelorette groups(we will also offer other packages for our non-bachelorettes). I’m considering baking her fees into the nightly rate and having this be a part of our listing. I have no idea if this will be well received but we are going to take the financial risk, try it out, and see what happens. If anyone has done something similar with success or has any thoughts on this idea I welcome your input:)
 
Regret-not finishing college. I didn’t want to end up financially in debt for the rest of my life. I watched and experienced my parents go through bankruptcy and this formed in me a strong desire for financial stability. (something I value).

I’m already working on one idea I’ve had since opening our doors at one of our locations that draws a lot of bachelorettes. I’ve joined forces with a friend who is an event planner and we are hoping to create discount packages & itineraries for our bachelorette groups(we will also offer other packages for our non-bachelorettes). I’m considering baking her fees into the nightly rate and having this be a part of our listing. I have no idea if this will be well received but we are going to take the financial risk, try it out, and see what happens. If anyone has done something similar with success or has any thoughts on this idea I welcome your input:)
Hey Trish!

We use the power of add-ons when building out packages, as not everyone is looking for the same experience. We set a small base fee for decorating or stocking the house with all the food and drinks they will need, they can even book in house spa treatments or a private chef with a deposit, and then we launch into the trip planning complimentary. (I do think there could be additional fees charged here) But guests go crazy adding on experiences! Especially this year, especially bachelorettes!

You're definitely on the right track to wow your guests and drive lots of word of mouth and repeat bookings! At least this is what we've seen! ;)
 
Regret; I used to be regretful that my passion for building my business was a major demise in my relationship, which I heavily believed in. Looking back it was all meant to be that we separated and both walked away stronger and I know I never would have taken the leap into business or believed in myself enough to do it without his encouragement in the first place. It was meant to be exactly as it was, sometimes we just can't see it in the moment.

Idea; I'd like to try to build a habitat home with my team from start to finish - homeowners, crew, and guest participation! Given back to someone who could use it and create a really cool way to come together. That could be an interesting local experience for guests, right? Haha
 
Idea; I'd like to try to build a habitat home with my team from start to finish - homeowners, crew, and guest participation!

Wow, this is an incredible idea! One of my biggest regrets from living in Panama was NOT taking everything we had achieved with the gang intervention program and creating the first former-gang-member-owned-and-operated vacation rental business in the world. I suppose what I valued (from that regret) was pursuing the boundaries of what is possible through hospitality to the point that I have no idea if it would have worked LOL
 
I was always encouraged by my family to be an entrepreneur (like they all were) but devoted my most of my working life to a health care career instead. While not necessarily a regret, I do wish I would have embarked on my second career sooner.

Laboratory science was an academic and interesting pursuit but extremely regimented around standards and best practice. There was zero opportunity to express creativity. In the vacation rental world, there is no box. No one tells us what is possible or impossible. And I love it.

I am consulting on an 18 room boutique hotel in Mexico with a trusted virtual team I have brought onto the project. The clients, colleagues and I have our flights book to meet face to face next month. It is joyous to interact with amazing people and do cool, innovative things in this industry.
 
Hey Trish!

We use the power of add-ons when building out packages, as not everyone is looking for the same experience. We set a small base fee for decorating or stocking the house with all the food and drinks they will need, they can even book in house spa treatments or a private chef with a deposit, and then we launch into the trip planning complimentary. (I do think there could be additional fees charged here) But guests go crazy adding on experiences! Especially this year, especially bachelorettes!

You're definitely on the right track to wow your guests and drive lots of word of mouth and repeat bookings! At least this is what we've seen! ;)
Have you ever thought about opening an OTA that targets bachelorettes? I see a space for this but it feels bigger than me. I’d need a team of people to make that happen.
 
Regret: Staying too long in corporate America. After spending 20yrs at a corporation with 100,000 employees it was easy to get complacent and not keep my foot on the gas. Life is too short and gets shorter by the day. Being an entrepreneur in this industry is the best move I ever made. Just wish it was 10yrs sooner. I value innovation, tech, and the ability to move quickly in a rapidly changing industry without having to run decisions by 20 other managers over a 3 month period.

Try at least once: Well... according to Brian Chesky in his latest podcast interview on PIVOT

apparently I need to add a "Treehouse Vacation Rental" to our 80 unit mix. He highlights that extremely "unique, one of kind" properties are performing the best... with some treehouses generating over 6 figures per year. Say what?? Ok Brian... you had me Treehouse.
 
Regret--not firing someone sooner. I delayed and delayed fearful I couldn't get a replacement, but once I pulled the trigger, it opened up the way for a much more positive addition to our team and we got along just fine. I was once told in the long process of not firing this person, that I would regret not doing it sooner. That was certainly true.

Idea--There is a new volunteer movement in our area that mobilizes people to clean up trash in the national park. Most of their volunteers are local residents but I think this would be a great opportunity for our guests to experience giving back to the community. Seems like our target audience (what we fondly call graduated tourists) would respond well to this opportunity. In the end we are taking care of our environment and promoting a positive message to guests to take care of our national park. Our employees could also sign up for a two hour slot (during work hours) and we will make it work for them to participate as well.
 
Regret-not finishing college. I didn’t want to end up financially in debt for the rest of my life. I watched and experienced my parents go through bankruptcy and this formed in me a strong desire for financial stability. (something I value).

I’m already working on one idea I’ve had since opening our doors at one of our locations that draws a lot of bachelorettes. I’ve joined forces with a friend who is an event planner and we are hoping to create discount packages & itineraries for our bachelorette groups(we will also offer other packages for our non-bachelorettes). I’m considering baking her fees into the nightly rate and having this be a part of our listing. I have no idea if this will be well received but we are going to take the financial risk, try it out, and see what happens. If anyone has done something similar with success or has any thoughts on this idea I welcome your input:)
TrishMixer TrishMixer I love this idea. You have to listen to this podcast with Susan Ho from Hopper Homes. She was an event planner at one time > https://thenobsshorttermrentalpodcast.com/episode/s2e10-with-susan-ho/
 
Have you ever thought about opening an OTA that targets bachelorettes? I see a space for this but it feels bigger than me. I’d need a team of people to make that happe

Have you ever thought about opening an OTA that targets bachelorettes? I see a space for this but it feels bigger than me. I’d need a team of people to make that happen.
Very interesting idea indeed. My housekeeping team would love it... 😂
 
Have you ever thought about opening an OTA that targets bachelorettes? I see a space for this but it feels bigger than me. I’d need a team of people to make that happen.
This is a great idea. Many hear the word "bachelorette" and automatically assume party animals but many just want to gather with their friends and celebrate the happy bride-to-be. My niece (earthy kind of gal) and her group made goddess head wreaths. This niche also has potential because it is very "Pinterest and IG-worthy" for marketing. Also, guests spring for more around special events like weddings.
 
Very interesting idea indeed. My housekeeping team would love it... 😂
Funny thing is I LOVE our bachelorette groups. I've banned the spawn of satan (confetti) but other than this they've been great!

My husband is a systems security guy and can do pretty much anything related to the tech space. We have been talking about this idea of a Bachelorette specific OTA on and off for a few months and we finally had the, "let's talk this through tonight" conversation so that I can finally put this idea to rest. Either we move forward or we stop talking about it:LOL: . If anyone else is interested in this idea feel free to reach out. I know it will take more than just the two of us to make this a reality.

I so appreciate everyone's input and suggestions. It was all VERY helpful. And Terry Terry that interview was just what I needed to hear to keep pushing these ideas of ours forward. Thank you for taking the time to share that with me!
 
This is a great idea. Many hear the word "bachelorette" and automatically assume party animals but many just want to gather with their friends and celebrate the happy bride-to-be. My niece (earthy kind of gal) and her group made goddess head wreaths. This niche also has potential because it is very "Pinterest and IG-worthy" for marketing. Also, guests spring for more around special events like weddings.
Exactly, they are willing to pay for a once in a lifetime experience. Just like the wedding space has exploded with different ways to celebrate, there's more room for growth and innovative ideas for bachelorette weekends and I'd love to be a part of making that happen. My experience as a hostess running multiple galas and large events and my love of design seems to suit the uniqueness of this space well.
 
Biggest Business Regret: Being too slow to act on things that didn’t work early in the development of our company. Unfortunately, if we are as successful as I hope we will be in being a positive influence on the STR market in San Antonio, “addition by subtraction” will be a major theme in what got us there. That’s mostly because when we would partner with someone or otherwise bring people I thought were potentially value added voices into our business or department in our business, it took me a long time to recognize to what extent their misalignment with my vision ended up changing so many things in that department that by the time the whole thing played out and they moved on, their exit made things got SO MUCH better. After reflecting, it has become clear how dumb it was of me to have kept the status quo sustaining for so long in certain circumstances regardless of the “why.” Point is, I have become less compromising in my vision these days knowing that there’s a difference between keeping an open mind and listening to the good ideas/insights of others and leading a company towards the future you believe in.



Idea: Creating a mixed use development where a luxury rental exists and the commercial space allocates most of its paces towards locally owned and operated pop up businesses for little to no rent cost but cater towards tourism synergized activities (anything from tours to small grocery), then push guests from that on site rental as well as other rentals in the area that we manage or other community members manage towards that retail space. Hopefully tourism dollars could then be funneled to the local community with the help of locally operated STRs pushing traffic to those locally owned businesses.
 
My regret is not going out on our own sooner. I wonder where we would be if our energy had been used building our business sooner rather than for someone else.

Idea- With the lack of employees and daycare we are looking at opening a daycare for our employees and their families. We have the building to do it in so now it is just figuring it out.
I am following this day care thing as it is very intriguing as a lot of our staff have the same issue! Government is giving a lot of grants and mula towards childcare, at least in Oregon so hopefully that will help in all your planning!
 
My biggest regret is self doubt so there are many things I wish I would have done because I feel like I would be farther along now had I taken some leaps.

Idea-Two things I have been mulling over is a dental program for staff (think big like helping staff get new teeth, we have a large area of poverty and recovering addicts who are sober but don't have the funds to fix their teeth) the other idea is how to give back to our community. We have full time residents that don't like vacation rentals so going to meet with our local chamber and see what we can do to help our area out so they can see the good in what we do!
 
I am consulting on an 18 room boutique hotel in Mexico with a trusted virtual team I have brought onto the project. The clients, colleagues and I have our flights book to meet face to face next month. It is joyous to interact with amazing people and do cool, innovative things in this industry.
Susanne Susanne , where in Mexico is the project? We have a vacation villa in Mexico, and I'd love to visit when it's completed!
 
Hey Kelley KSanchez KSanchez, it is in San Pancho north of PV. This is somewhere I could easily live for the winter; I will share the link when it's ready to go.
A little glimpse, I went on a 3-hour hike to a secluded beach for sunset yoga. The hike was so exhilarating, more rock climbing than hiking in places. It made the yoga that much more zen. There were the foodiest restaurants which take everyone by surprise. One of my tasks was to create a great destination guide. It was a good gig I must admit.
 

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Susanne Susanne, wow San Pancho! Our house is near Lo de Marcos (about 15-20 min. north). San Pancho has grown enormously popular in the last 5 years and is not much of a "secret" anymore. We really like it there :)
 
I was always encouraged by my family to be an entrepreneur (like they all were) but devoted my most of my working life to a health care career instead. While not necessarily a regret, I do wish I would have embarked on my second career sooner.

Laboratory science was an academic and interesting pursuit but extremely regimented around standards and best practice. There was zero opportunity to express creativity. In the vacation rental world, there is no box. No one tells us what is possible or impossible. And I love it.

I am consulting on an 18 room boutique hotel in Mexico with a trusted virtual team I have brought onto the project. The clients, colleagues and I have our flights book to meet face to face next month. It is joyous to interact with amazing people and do cool, innovative things in this industry.
Hola Susanne, we owned two casas in San Pancho for seven years. We lived in one for six months a year and rented the other. We sold it in July.
 

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