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The Road Less Chosen - Podcast

The Road Less Chosen

A fascinating AirBnB and Short Term Rental podcast that dives into the stories of industry leaders who took the path LESS CHOSEN in their business and life. We're talking about the decisions they made that are too uncomfortable for most people to make...
When was a time you went left when everyone else went right?
How do you deal with being out of your comfort zone?
What benefits (or mistakes) do you see in your life that propel you forward?

We cover it ALL. Tune in and maybe you'll hear something that changes the trajectory of YOUR business or life.

Business Real Estate Entrepreneurship Mindset
Update frequency
every 7 days
Average duration
37 minutes
Episodes
19
Years Active
2025
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Corporate Comfort to Airbnb Empire: How Mark Palmiere Used Faith & Mindset to Change Everything

Corporate Comfort to Airbnb Empire: How Mark Palmiere Used Faith & Mindset to Change Everything

"Most people focus on the worst-case scenario, but that's putting too much attention on the wrong thing"

Today we sit down with Mark Palmiere, seven-figure STR co-host and mindset coach.

We talk about:

00:36:29  |   Wed 20 Aug 2025
Freight Chaos to Property Management Trailblazer: Quinn Foster’s Partnership Strategy

Freight Chaos to Property Management Trailblazer: Quinn Foster’s Partnership Strategy

"I knew if I followed everyone else, I’d know exactly what my future looked like and that didn’t sit well with me."

 

Today we sit down with Quinn Foster, CEO of Feather PMS and CRO of Stay Duvet. We t…

00:34:06  |   Thu 17 Jul 2025
Pro Soccer to Virtual Assistant Agency: How Danny Reynolds Embraces the

Pro Soccer to Virtual Assistant Agency: How Danny Reynolds Embraces the "What If"

"You know that saying - Build the plane while you fly it? It's true."
 

Today we sit down with Danny Reynolds, Part Owner and Chief Strategy Officer at Valor Pro Virtual Assistance. We talk about:

• How…

00:36:00  |   Tue 24 Jun 2025
Overhearing Dad's Sales Calls to Managing Large Portfolio: How Joe Prillaman Masters

Overhearing Dad's Sales Calls to Managing Large Portfolio: How Joe Prillaman Masters "The Pivot"

Today we sit down with Joe Prillaman, Short-Term Rental Investor with 25 owned doors and 70 managed listings. 
We talk about:

  1. How surviving a hurricane forced a game-changing pivot in his STR business
  2. T…
00:39:52  |   Tue 10 Jun 2025
9-5 Engineering Job to AirBnB: How Jay Ullrich Assesses Risk

9-5 Engineering Job to AirBnB: How Jay Ullrich Assesses Risk

Today we sit down with Jay Ullrich, CEO of Hostbuddy AI and Co-Founder of SelectStays.

We talk about:

  1.  How to assess risk when evaluating a new opportunity
  2.  How to boost your AirBnB listing in the algor…
00:40:04  |   Tue 03 Jun 2025
Risk-Adverse CPA to Rental Portfolio Entrepreneur: Daniel Roger's Journey (and Andrea's Client)

Risk-Adverse CPA to Rental Portfolio Entrepreneur: Daniel Roger's Journey (and Andrea's Client)

"Put me in a room full of entrepreneurs and I'll likely be the most risk-adverse one in there, but put me in a room full of CPAs and I'll be the riskiest one." Daniel Rogers, founder of Furnished By …

00:42:15  |   Tue 27 May 2025
Eiffel Tower Spark to STR Star: Overcoming Depression & Trusting God

Eiffel Tower Spark to STR Star: Overcoming Depression & Trusting God

Today we meet Tiffanie Jensen, co-founder of Premium Rentals with her husband, whose passion and dedication to growth has led to a portfolio of over 100 STR properties - all while raising 6 kids. How…

00:36:57  |   Tue 20 May 2025
OBGYN to AirBNB Arbitrage: Dr. Jessica's Freedom Formula

OBGYN to AirBNB Arbitrage: Dr. Jessica's Freedom Formula

Join us as we dive into the extraordinary journey of Dr. Jessica Katz – AirBnB arbitrage expert, real estate investor, and mom of four, who turned 77 rejections into a 30-property STR empire that out…

00:31:32  |   Tue 13 May 2025
How a Mural Mishap Turned Into a Win For This AirBnB Home Designer

How a Mural Mishap Turned Into a Win For This AirBnB Home Designer

Today we sit down with Brianna Amigo, founder of Brianna Michelle Interiors, an STR design pioneer whose stunning, bespoke properties have elevated over 300 rentals, driving client revenues up by as …

00:33:44  |   Tue 06 May 2025
From Rejecting a NYC Job to Taking the Risk of STR Designer & Muralist

From Rejecting a NYC Job to Taking the Risk of STR Designer & Muralist

Join us as we dive into the vibrant world of Bella Linchenko, co-founder of Let’s Go Design Co., renowned muralist, and short-term rental designer who’s transformed properties into guest magnets with…

00:40:19  |   Tue 29 Apr 2025
Why a Cop Quit His Badge to Master STR (and How Spotify Inspires Him?)

Why a Cop Quit His Badge to Master STR (and How Spotify Inspires Him?)

Meet Luke Kolk, the former police officer turned CEO of Kolk Homes, who with his wife scaled 120+ STR deals in four years, fueled by relentless innovation. Why does Spotify hold the key to his client…

00:40:49  |   Tue 22 Apr 2025
From Firing Your Spouse to Massive Growth: One Couple's Path to STR Success

From Firing Your Spouse to Massive Growth: One Couple's Path to STR Success

Join us as we sit down with Aaron Kirkham to have an incredibly honest conversation about his path to STR success. From Idaho farm kid to college mascot to STR leader. Ever wonder how shaking off env…

00:36:49  |   Tue 15 Apr 2025
2.0 to 4.0 GPA: But Was He On The Right Path?

2.0 to 4.0 GPA: But Was He On The Right Path?

Join us as we dive into the wild journey of Patryk Swietek, a short-term rental titan who’s scaled to 100 properties and an 7-figure empire, all starting from a scrappy 12-year-old snow-plowing hustl…

00:34:55  |   Tue 08 Apr 2025
Why the Airbnb Data Guy Gave Away His Secrets – For Free (And How to Access Them!)

Why the Airbnb Data Guy Gave Away His Secrets – For Free (And How to Access Them!)

Join us as we sit down with John Bianchi, the legendary Airbnb Data Guy, founder of STR Search, and head of data at TechVester—the largest short-term rental investment fund in America—who’s helped se…

00:45:37  |   Tue 01 Apr 2025
What's More Important Than Honesty? The Strategy to Upgrade Your STR Online Presence

What's More Important Than Honesty? The Strategy to Upgrade Your STR Online Presence

Mercedes Sanchez, a hospitality natural who turned a Vegas high school gig into a Four Seasons career before founding MBX Homes, now manages 80 luxury properties with a refreshingly honest approach. …

00:30:18  |   Tue 25 Mar 2025
From Hospital Halls to Creating an AirBnB VA Revolution

From Hospital Halls to Creating an AirBnB VA Revolution

What drives someone to abandon a stable gig to create a rockstar Virtual Assistant Agency for STR owners? Stephanie Fageros, once a nurse tethered to an eight-year career, catapulted into entrepreneu…

00:33:44  |   Tue 18 Mar 2025
He Uses ChatGPT For What?? Discover This Genius Use Case For Success

He Uses ChatGPT For What?? Discover This Genius Use Case For Success

Daniel Johnson, currently a founding member of Crew Home with 4 startup exits under his belt, joins us to share his unconventional rise in tech, real estate, and startups. Wait—did he really use Chat…

00:51:29  |   Tue 11 Mar 2025
From Dolly's Stage to Mortgage Mogul: The Inside Scoop

From Dolly's Stage to Mortgage Mogul: The Inside Scoop

From Dolly Parton’s stage to the top 1% of lenders, Brenna Carles now helps Airbnb owners with financing as the founder of The Mortgage Shop. What wild twist turned a Smoky Mountain songbird into a s…

00:36:55  |   Wed 05 Mar 2025
Quitting University to... Full Time Sky Dive?? James Svetec

Quitting University to... Full Time Sky Dive?? James Svetec

Have you ever thought about doing something a little crazy? James Svetec has. As the author of AirBnB For Dummies and the founder of BNB Mastery and BNB Tribe, James is a living example of taking the…

00:34:01  |   Fri 28 Feb 2025
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