Entrepreneur turning ideas into reality. Started 30 companies. $1 Billion + in sales. Sold last company to KKR. Currently building one of a kind luxury Airbnbs.
Quick Intro:
- grew up homeless
- dropped out of high school
- founded more than 30 companies doing $1B+ in sales cumulatively
- last company founded was RVshare (sold to KKR)
- currently building unique luxury short term rentals
Here are a few of my favorite STR projects👇
Is flying private worth it?
Apparently studies show that private planes are 200 times more deadly than commercial.
I didn’t know this until doing research after a frightening experience last week.
My family boarded a private jet and I took this video when we were taking off.
Comment from a realtor we talked to in Arizona this week:
“I’ve never seen this many vacation rentals come on the market for sale. Every day someone is asking us to list their Airbnb for sale.”
We have 2 Airbnb bookings for the super bowl next year that add up to more than $250,000. This is crazy!!! These bookings pay for the mortgage plus all operating expenses for the entire year.
I recently got a beach house to use as my “office”.
It’s the best investment I’ve ever made.
I had no idea how much I would enjoy being at the beach everyday.
Taking a daily walk down the beach, looking up from my laptop and seeing surfers and dolphins.
I am so grateful 🙏
I’m planning a one year trip around the world with my family.
The goal is to experience different cultures, live like a local, and do something philanthropic in each location.
12 months. 12 different cities.
Where should we go?
Has anyone done something like this before?
Thank you
@ClintFiore
for sharing some additional data that provides further insight. The 200X number I shared while it might be technically accurate. There’s nuance to it. This is good to know.
It's finally complete. This is the coolest Airbnb we've created yet. See 100+ photos here:
Leave a comment and post the photo you think we should use as our main cover photo. It doesn't need to be one of the 3 that I posted, there are 100+ to choose from.
Holly shit. I just experienced the scariest moment of my life.
A few minutes ago I was walking down the beach with my son collecting seashells.
When out of the blue a rouge wave came in and submerged him and smashed him into the rocks.
I immediately dove into the rocks after
Want to turn your kid into an entrepreneur? Here’s a great tip👇
My friend told me about something he does with his daughter and I thought it was genius. I loved the concept so much I’m now doing it with my kids. If you have kids you may want to consider doing this too. 🧵
I sacrificed years of my life working 7 days a week building different companies I started.
Lots of failures and a couple big successes.
The payoff was worth it.
Its Wednesday and I spent all day on the beach with my kids. We collected driftwood and built a fort.
In 24 hours I’m giving away a FREE 2 night stay at this one of a kind family friendly Airbnb.
To win post a comment, like or retweet.
Happy Thanksgiving 🦃
Own an Airbnb?
Get 20X to 500X return on investment with this “Airbnb hack”
Split test your Airbnb cover photo by running ads on Facebook/Instagram.
Here’s a test I just ran for $50. This test should yield higher search results and an extra $20,000+ a year in bookings for us.
What's better than a private jet?
A tour bus.
I had to go visit one of our properties in Paso Robles.
Last time I visited this property I chartered a jet, this time I chartered a tour bus.
The bus was a fraction of the cost and a better experience.
Door to door pick up
This was the best $200 I ever spent.
The kids were sleeping in their beds and they heard the sound of bells jingling in the living room.
We go see what was making the noise and look who we found climbing out of the fireplace.
Santa made a visit to our house on Christmas Eve.
I’m looking for someone in the insurance industry who can underwrite an insurance policy for a go-kart track at a short term vacation rental.
If you can do this let me know.
I had lunch with a friend today who purchased 100 single family homes in Michigan for $100 in 2008.
This was at auction. He bid $1 each and there were no other bidders.
Some of the homes were worth very little and others he sold for more than $50,000 each.
Twitter friends I’m inviting you to stay at one of my Airbnbs on me (at cost, no markup)
Stay in a $1500 a night Airbnb for $235/night.
Stay in a $6000/night Airbnb for $600/night.
Normally I only share these deals with friends and family.
👇
Haven't been on Twitter much recently because I'm working on a new startup.
I came up with the idea a month ago. Last week I launched the website. Today I launched paid ads.
Not sharing what the company is yet. If it gets traction, I will be recruiting a small founding team.
Flying to the east coast to work on one of our Airbnbs. I’m extremely grateful to be able to fly private with the family. It makes traveling with kids 100x easier.
We have a property with a small vineyard that produces 3000+ bottles of organic wine per year. I need to come up with a name and label for the wine. Any ideas?
We are overjoyed to add this little guy to our family. Our son Hayes was born on Nov 28.
To celebrate I want to pay it forward.
In 24 hours I’m going to send $1,000 to someone who needs a little help right now.
Like, share or post a comment on what you would do with the money.
I had a couple big YouTubers over to the house the other day.
One has 1.6M subscribers and the other 22M.
They told me the difference between TikTok ad revenue and YouTube ad revenue.
5 million views on TikTok = they earn $150
5 million views on YouTube = they earn $40,000
I’m hiring a remote part time chief of staff/executive assistant, comp starts at $100/hr +
Requirements:
- Honest
- Ethical
- Smart
- Problem solver
- Self starter
- Resourceful
- Track record of success
DM me if interested.
White collar jobs are more at risk with advances in technology than jobs in the trades like ironworkers, plumbers, electricians, HVAC.
AI isn't going to automate the installation of a new air conditioner. But it will automate your accounting job.
When I was a young my idea of financial success was earning $100k a year and living in a $200k house.
Now it’s owning Gulfstream, having a family office and charitable foundation.
Just because you grow up on the wrong side of the tracks doesn’t mean you need to stay there.
One of the best pieces of business advice I ever received was this question:
“Are there any old happy rich guys doing what you do?”
If the answer is no you may want to seriously consider doing something else.
Giving our Airbnb guests a world class experience is our true north.
We have created a 332 point checklist we use to ensure the property is perfect when our guests arrive.
After our cleaners clean and before our guests arrive we have an inspector go through with this list.
The same new home builder is selling both of these homes. (LENNAR)
Home
#1
near Indianapolis is 2799 square feet, and you can buy it for $370k
Home
#2
near Los Angeles is 2173 square feet, and you can buy it for $1.9M
If the super bowl comes to your town, you may want to consider renting your house.
We have 2 Airbnb bookings for the super bowl next year that add up to more than $250,000.
This pays for both mortgages and all annual expenses, utilities, taxes, etc.
I grew up homeless and this is the garage I lived in. I dropped out of high school and my teacher said I would be a loser. But that didn’t stop me because I was motivated to build a better life. I went on to start more than 30 companies which have done $1B+ in sales cumulatively.
Hire people who are lucky.
How do you know if someone consistently gets lucky in life?
Ask them: Are you lucky?
This will give you good insight into how someone views the world.
Let your competitors hire the people who consistently have bad luck.
Shipping container swimming pool.
I didn’t even know this was a thing until
@thesamparr
sent me this the other day.
Now I’m thinking about installing one of these at our Sedona project.
Has anyone installed one of these? Would love to hear pros and cons.
Holy cow 🐄
I just had dinner with a friend. He’s running an affiliate program and his top affiliate generated more than $55 million in sales last month for his business. His affiliates are on pace to generate $800+ million in sales this year.
Absolutely insane!
$100 million in profit from direct mail.
In 2007 Ben Suarez started selling infrared heaters via direct mail.
It was a huge success. At its peak, his company was doing $500M a year in revenue.
He was making so much ($100M/yr in profit) that he owned a Boeing 717 Private Jet.
Will the recession impact high end STRs?
YES
Last weeks new STR booking revenue is the lowest I’ve seen in several years.
Year over year booking numbers for last week.
Last week: $38,767
Same week last year: $196,848
I can’t recall a week that’s been this low in years.
Are there any photographers who would like a free vacation?
You will get to stay at some of the coolest Airbnbs in the U.S.
I will pay for your airfare, rental car and host you at one of our world class Airbnb properties in exchange for you taking photos of the property.
This is one of the best things I’ve done with my kids.
I created a ticket they can give me anytime they want me to stop working and play with them.
When I get this I’ll drop whatever I’m doing and go play with them for 10 minutes.
Yesterday I was on a small group Zoom call with Billionaire investor
@StevenACohen2
Steve was the inspiration for the hit TV show "Billions".
4 takeaways:
1. Quote from Steve: "When I'm with someone I respect, I try not to talk a lot. I focus on listening".
I think removing cleaning fees on Airbnb is all smoke and mirrors.
Hosts will need to charge the same amount regardless.
The issue is with Airbnb and the way they display pricing.
They chose not to display additional fees upfront because it hurt conversions.
End of story.
I have a good friend who makes videos on YouTube. Every day for the last three years he’s made a video. In his first two years he made less than $5,000. In his third year he made almost $3,000,000. Most people aren’t this dedicated which is why they never achieve outlier results.
Airbnb earnings call is bad news for hosts.
Airbnb wants hosts to have a race to the bottom with pricing.
This is good for Airbnb because conversions and bookings will increase.
This is bad for hosts because additional yield STR provides over LTR will disappear.
My mom gave me a beautiful gift when she died and she didn’t even know she was giving it to me.
It’s something that you can give to your loved ones when your time is up.
My mom‘s final resting place on earth is in Santa Barbara on a cliff overlooking the Pacific Ocean. It’s
Here's an idea for a business:
A website where you enter a room type (bedroom, living room, etc.) along with room dimensions, and it shows you different pre-designed rooms.
Then with one click, you can buy everything in the room (furniture, art, rugs, wallpaper, etc.)
Anything is possible.
Years ago I lived in a garage behind a tire shop.
Now this is my office.
Blessed and grateful. A lot of hard work and a little luck.
Yesterday I met someone from Cuba who was smuggled into the US by a coyote a few months ago.
He and his brother both fled Cuba and snuck into the US.
It was surreal to hear their story.
They are talented film makers with a promising future to do big things.
Here are two
Observation from traveling: the more expensive the hotel, the friendlier other guests are.
I don’t think this is because people who have more money are inherently nicer. I think it’s because they have less stress.
Money doesn’t buy happiness but it can eliminate some stresses.
Which one of these will be worth more in 10 years?
This 4 bed 3 bath 2720 sq ft home in Belleville, IL that is currently for sale for $237,500
or
This 43 sq ft parking spot in Vail, CO that is currently for sale for $239,500
This new year…
Don’t compare yourself to others.
No one else on earth was given the exact same advantages, disadvantages, and raw talent as you.
Compare yourself to yourself:
1 year ago
5 years ago
10 years ago
Never compare yourself to others because they aren’t you.
Made a very strong offer on this house today. I should be finding out tomorrow if we get it or not. 7 bedrooms, 2 guest homes, 2 swimming pools, tennis court, large koi pond, on 5 acres. Needs some interior updates but tons of potential. Fingers crossed 🤞 we will get this one.
We got a quote to build a standard pool (nothing special) in Sedona for $250k. I remember when you could build a new 2500 sq ft home for $250k. Today all it buys you is a pool. Called 5 contractors, only 2 came out to bid the job, only 1 actually submitted a bid. CRAZY!
I hate to say this, but I think everyone would be happier if we didn't have cell phones. The dopamine hits coming from your phone are stealing your time that you could be using to enjoy real people in the real world.
We will pay our Airbnb cleaners more than $600,000 this year.
14 active properties = $43k per property.
I’m happy for them, they are hard working and deserve to earn a good living.
It shouldn’t just be the people at the top reaping all the rewards.
If you have the desire to get rich, you need to constantly be around rich people.
Offer to help them however you can and always go the extra mile above and beyond what's being asked.
Do this, and life-changing opportunities will appear in front of you.
I’m hiring a remote chief of staff/executive assistant. Comp starts at $100/hr +
If you refer someone to me and I hire them I’ll fly you first class to San Diego and host you for 3 nights at my Airbnb below.
DM me if you know the perfect candidate.
Insights from a private meeting with 11 high net worth business owners/investors today.
Here’s the consensus amongst the group:
- everyone is currently very cautious
- no one is deploying capital right now
- building up cash reserves
- expecting further drop in asset prices
STR owner's Photos are EVERYTHING when it comes to marketing your property. We almost always hire two different photographers to shoot the property. Here's a good example of why. Both of these photos were shot by top-rated photographers. One is obviously far superior to the other
There needs to be a podcast with this one premise:
Interview people in the top 1% of their field and have them walk the audience through a step-by-step roadmap for what they would do if they had to start over again from scratch with no knowledge, connections, or money.
I like Twitter however when I don’t use the app for long periods of time I find myself happier, more present, and less distracted.
The dopamine hits from Twitter are real.
I’m still trying to figure out how to regulate Twitter usage in a good way.
I can’t let the dopamine
Hi friends 👋 I just read what I believe to be the best book on achieving success ever written.
" The Wisdom of Success" by Andrew Carnegie and Napoleon Hill
I wanted to share some of the biggest takeaways from the book.
These principles have helped me enormously in achieving
This is such a cool property! I would love to buy this and turn it into an Airbnb but the financials don't make sense. Complete privacy on 21 acres in beautiful northern Michigan.
I know what it’s like to be poor. It sucks. I used to live in this garage below. For everyone out there busting their ass to build a better life for themselves and their family, keep pushing forward. The rewards are worth the sacrifice.
When I was young and broke, on weekends I would drive around and go to open houses in the nicest parts of town. I would walk through the homes and think to myself one day I will live in a house like this.
I’m going to do an STR that focuses on health/working out. I’m planning on adding all of these:
Peloton, Tonal, Treadmill, Free Weights, Barre/Yoga, Sauna, Cold Plunge, Hot Tub, Massage Table
What else am I missing…
Sunday night at the Jenney house.
I’m feeling so much gratitude for an amazing family, awesome friends and a life I could only dream about when I was a poor kid on the wrong side of the tracks.
If you are in the process of making your dreams a reality I’m cheering for you!
I’m taking a break from the bird app for a little while. Twitter is great, but it can be addictive. I’m doing a digital detox this next month. Focusing on family and enjoying nature without distractions.
Orlando has an over supply of STRs which makes it a bad market for investors.
Phoenix/Scottsdale is now facing this same issue.
Good for guests. Bad for hosts.
One thing I would like to see come out of this recession is: less startups celebrating funding rounds and more startups celebrating actually being profitable
In 2019 I almost bought this house for $4M.
It just came back on the market for $20M.
Sure they did a nice remodel but 5X the price 🤯
Every time I see Paradise Valley, AZ price appreciation it blows my mind.
This property is a masterclass in how to achieve outsized returns by creating a theme with your Airbnb.
Airdna shows this 1 bedroom is making $104,700 a year.
I’m thinking about installing a commercial golf simulator in one of our new Airbnb’s. My only concern is ongoing maintenance and tech support. Should I do it yes or no?
I sent a cold email to someone I’ve never talked to before.
Their assistant connects me and here’s the response.
Them: “Do you own the Airbnb with a ball field in Poway?”
Me: Yes
Them: I’m staying there next week.
Now we are meeting in person. How serendipitous.