The Fearless Investor

Friend of the podcast, Mark Simpson, is back with a big announcement! Mark is the Founder and CEO of Boostly, your go-to guy for all things direct booking.  Get a first look into this exciting announcement dropping on December 26th by listening to our conversation. Then, head over to YouTube, search for “Boostly” and click the “notify me” button you’ll see on the first video to be the first to hea...

When Jon and Bethany started on their short-term rental journey, their goal was for Bethany to hit retirement from her job within 12 months.  Well, they did it within 12 weeks! Mainly through arbitrage and co-hosting eight properties.  Hear their strategy on this episode of the podcast. Learn more about the 6-Figure Formula Jon and Bethany follow here: fearlesskyle.com/6ff Want more tools, tricks,...

This is a very honest letter that I wrote in hopes that it will reach Brian Chesky. Airbnb has gone through many changes in the last few years. Some of those changes have caused a lot of frustration among hosts and guests. Sometimes, when you are at the top of a company, you are detached from your customers. My hope is that this letter nudges Brian to reconnect on a deeper level with Airbnb hosts....

Powerhouse STR host, Hailame Kinikini, returns to the podcast to share how he’s purchased over 100 properties with creative financing.  This conversation was one from our private 6FF Community that I didn’t plan to share. But - the information is just too good and I wanted the full Fearless Investor Podcast community to have access.   Many of you have said that you want to move from arbitrage and...

Short-Term Rentals converting to Mid-Term Rentals. This is a big deal right now when it comes to regulations, changes at Airbnb and uncertainty in the market.  Today’s podcast guest, Ruben Kanya of Experimental Real Estate, is converting many of his properties and networking with other owners as an exit strategy. Listen in now to hear Ruben’s tips. Learn how to price your properties like an STR Pr...

What do you really need to get started in STR? The options can be overwhelming.  Will your property make money? What should you price it at? How do you know? My recommendation: PriceLabs and AirDNA are the two softwares you need when starting in short-term rentals.  I’ll explain why in this week’s podcast. Ready to take the next step? Get your Market Eval Kit here: https://bit.ly/marketevalkit Sta...

Today’s podcast is packed with helpful information for you, Airbnb host!  Former Airbnb employee, Danny Rusteen, weighs in on everything from Brian Chesky’s interview on Diary of a CEO to the recent changes at Airbnb and more. We also discuss Danny’s newest book, “Profitable Properties: Airbnb Insider Secrets for Short-Term Rentals.”  Plus, Fearless Investor Podcast listeners get 50% off LIFETIME...

Is the checklist running through your mind each night keeping you awake, costing you precious sleep?  Today we have Madison Romeli of Breezeway on the podcast and get this - before Madison ever worked for Breezeway, she was working with this platform in her 50-unit short-term rentals business.  Listen in for her tips to streamline those STR operations and run your business more efficiently.  Get 1...

Offer experiences without lifting a finger and get paid to do it. Mount brings experiences direct to your guests, from stay enhancements to local gems.  These offerings help your STR properties be memorable to travelers, making you stand out among the rest.  CEO Madi Rifkin returns to the podcast to explain and share an update from Mount, launching October 22. (But you can get early access by clic...

$7 millon over the next 5 years. Nothing worth having is ever easy to obtain, but MTRs certainly have their benefits! Today on the podcast, Jeremy Nixon joins as we break down the numbers and learn how he secured his first multi-million dollar government contract.  www.fearlesskyle.com/pathwayfinancial Ready to learn about government contracts from the master just like Jeremy? Get connected with J...

Get all the benefits of arbitrage without any of the upfront costs. Sounds too good to be true? In this week’s podcast episode with guest, Brian Hatcher, we’re talking all about Timeshare Arbitrage. Brian has over 300 units. There’s no furnishing and no maintenance work. Brian just focuses on marketing the properties (via Airbnb, VRBO, etc.) and guest communication. Ready to learn the ins and outs...

We’re back with another feature from my recent Cabo Mastermind, today with Amanda Williams, real estate professional and Owner of Carolina Furnished Rentals. Amanda only rents long-term, but this business has afforded her many benefits including early retirement and much-needed support when her father was in the hospital undergoing cancer treatment. Listen in to hear how Amanda runs her company. w...

We’re talking hotels and multi-family, live at our hotel in Cabo direct from my recent mastermind with TJ Tijani on this episode of the podcast.  This area of real estate has evolved quite a lot over the last several years and TJ is right in the middle of it! I know you’ll hear at least one key takeaway you can start to utilize in your own STR business.  www.fearlesskyle.com/easieraccounting Did...

If you own STRs, this is the one podcast you cannot miss.  I’ve got Rhett Gagon, Executive Vice President of Cost Segregation Authority with me to discuss the STR loophole and cost segregation. We use my actual properties to show a live example of how you can save $10,000s.  www.fearlesskyle.com/pathwayfinancial Fill out this form and mention the Fearless Investor Podcast to get started with a no-...

If making cold calls and networking your face off just isn’t appealing, then today’s podcast is for you!  SEO expert, Tristan Petricca, joins me to talk digital marketing, how to 10X your STR business and grow leads with Google. www.fearlesskyle.com/easieraccounting Ready to learn SEO for your own STR business? Save 15% with code fearlesskyle on Tristan's site: seoforstr.com/kyle/ Want more tools...

Short-term rentals. Still viable? Something you should get into and keep building? Or is it time to plan your exit?  On today’s episode, we’re talking unique properties, regulations and more with Alex Jarbo. Alex is the primary writer on short-term rentals for BiggerPockets and founder of Open Atlas, an investment and management firm dedicated to developing and acquiring distinctive short-term ren...

Syed built his STR business to 180 units. Then - COVID happened.  But Syed Lateef’s story does not end there. He rebounded back and doubled his business. Now he has 300+ AirBnBs with 100+ employees. During our conversation, Syed will share how he went from $10,000,000+ AirBnB revenue in 2022 to $1,000,000 per month in 2023. Connect with Syed directly at syedbnb.com and on Instagram @syedbnb. www....

Is REI worth the risk? My company manages 50+ properties and we grossed $2.5M+ of revenue in 2022. If you’re not sure where to begin in real estate investing but you’re anxious to jump in, I’m sharing the seven steps to get you started on today's episode.  www.fearlesskyle.com/pathwayfinancial Want more tools, tricks, and resources? We have you covered! You can check out everything on www.fearless...

If you’re serious about supercharging your business and streamlining operations, you need one of the best channel managers on the market.  In my opinion, that’s Hostaway!  Marcus Rader, CEO and Co-Founder of 6FF preferred partner, Hostaway, joins me on the podcast to share more about their platform including their recent investment (hint: it's the largest single capital raise in the vacation renta...

Henry Washington has over 100 long-term rental properties, but he keeps a small number as short-term rentals.  Today, this BiggerPockets podcast co-host shares why on the Fearless Investor Podcast. Get connected and DM Henry on Instagram (@TheHenryWashington) with "FearlessKyle" to get more information on his coaching program: https://www.instagram.com/thehenrywashington/ www.fearlesskyle.com/path...

What’s the best pricing strategy for your AirBnB listing? Today I’m talking with TechTape’s John An. He uncovers the facts and data to get you to the right answer. John shares how he took a two-bedroom, two-bath property to $200K/year and how you too can blow the competition out of the water.  Ready to get started? Book a free call with John here: promo.gettechtape.com/rm?prefill_Code=FEARLESS2023...

Ready to take your STR business from side hustle to seven figures? Want to learn how from someone who’s built three, eight-figure businesses?  Bill Faeth is a #1 Best-Selling Author and Founder of Build Short Term Rental Wealth. He has been involved in real estate for almost 25 years with both commercial and residential investing. Today, he’s sharing secrets to his success on the podcast.  Connect...

Mark Simpson is a wealth of STR knowledge, from direct bookings to AI tools. Today, he joins me on the podcast to discuss both automating and elevating your business with AI.  We discuss different tools, get an update on Guest Guru (why did it shut down… and is it coming back?) and how to streamline operations by combining tech with your company manual. Think AI is just a phase? Mark challenges bu...

Avoiding short-term pain leads to long-term dysfunction. This is certainly true when it comes to leading your team. I run an AirBnB business with 52 priorities and 20 people on our team from vendors to managers and VAs. Today on the show, I’m adding my thoughts regarding Leila Hormozi’s recent podcast release and sharing ways to get ahead of those difficult conversations! www.fearlesskyle.com/path...

The City Council in Dallas, TX has voted, banning STRs from neighborhoods with single-family homes. Join the fight for a common resolution as Theron Lewis, The STR Hero, joins me on this important podcast to share how.  Take action:  Donate to the Dallas cause: https://bit.ly/dallasstrdonation Join the Dallas STR Alliance: https://www.dallasstra.org/ Connect with Theron at www.strhero.com www.fear...