Grow STR is the podcast for short-term rental operators who want to escape the W-2 grind and build a real STR business, not another stressful job.
Each week, we dig deep into what it actually takes to grow and scale: owner acquisition, operations, systems, sales, and the mindset to stop chasing shiny objects and start building freedom.
Learn how to find and sign profitable STR clients, build repeatable sales systems, create SOPs so the business runs without you, and turn your STRs into a stable, scalable asset that can replace your W-2.
No fluff, no get-rich-quick fantasy—just real talk for
From Failed Pitch to Startup Winner: Jeff Smith on Scaling, Networking, and Building Home Tours Pro
Jeff Smith’s first startup pitch went so badly that the organizers asked him to stop talking. At his next competition, he finished on time—and won first place.
In this episode of the Grow STR Podcast, Jeff shares his path from banking and real estate photography into accelerators, pitch competitions, proptech, and the venture-backed startup world. He explains the major difference between building a steady lifestyle company and pursuing a high-risk, scalable startup.
Jeff also shares the networking lessons that shaped his career, including how a bag of ramen taught him to create win-win transactions, why successful leaders often want to mentor the next generation, and how intentional relationships can open doors that cold outreach cannot.
You’ll also hear how Home Tours Pro evolved from a local photography business into a technology platform designed to improve and scale real estate media.
Connect with Jeff:
Website: hometourspro.io
LinkedIn: Jeff Smith, Home Tours Pro
Jeff is currently seeking a technical co-founder, angel investors, and strategic partners within real estate, short-term rentals, construction, and property media.
18 Jun 2026
From 40 Rentals to 20: Bernie Cesario on STR Profit, Midterm Rentals, and Investor Partnerships
Bernie Cesario built Eagle Stays by learning that more properties do not always mean a better business.
In this episode of the Grow STR Podcast, Bernie shares how he transitioned from a W2 career in mortgage banking and IT into short-term rentals, midterm rentals, and investor-backed property management. He explains why he cut his portfolio from 40 units to around 20, how revenue stayed strong, and why smaller units were taking too much time for too little return.
Bernie also breaks down how insurance relocation stays and construction crews became powerful midterm rental opportunities, how large homes perform in urban markets, and why investor partnerships work best when trust, sweat equity, and clear agreements are in place.
This episode is for short-term rental hosts, midterm rental operators, Airbnb co-hosts, property managers, and real estate investors who want to grow smarter instead of simply adding more doors.
Connect with Bernie:
Eagle Stays is an accomplished Airbnb Superhost and VRBO Premier Host, as well as co-host a portfolio of properties under their own platform, (http://eaglestays.com/)EagleStays.com (http://eaglestays.com/). In addition to short-term rentals, they also rent the portfolio as mid-term rentals. They work closely with investors to host properties, identify and acquire homes for STR and MTR use, and create opportunities designed to fill sustainable, long-term financial goals and passive income through professionally managed rentals.
Socials: https://www.facebook.com/bernie.cesareo (https://www.facebook.com/bernie.cesareo)
https://www.instagram.com/the_str_bnb_guy (https://www.instagram.com/the_str_bnb_guy)
https://www.linkedin.com/in/bernie-cesareo-6979647/ (https://www.linkedin.com/in/bernie-cesareo-6979647/)
https://EagleStays.com/ (https://eaglestays.com/)
11 Jun 2026
From Healthcare to STR Co-Host: Kelsey Johnson on Networking, Design, and Growing a Rental Management Business
Kelsey Johnson traded her healthcare career for short-term rental co-hosting and property management, and built her business through referrals, networking, guest experience, and better owner support.
In this episode of the Grow STR Podcast, Kelsey shares how she discovered short-term rentals, learned through mentorship, landed her first co-hosting client through BNI, and eventually stepped away from healthcare to focus on her property management business full-time.
She also talks about the real work behind growing a co-hosting business: networking consistently, onboarding owners, setting expectations, improving design, using professional STR photography, avoiding unnecessary tech tools, and knowing when to hire help.
This episode is for short-term rental hosts, co-hosts, Airbnb operators, and property managers who want to grow through relationships, referrals, better systems, and unforgettable guest experiences.
Connect with Kelsey:
Instagram/Facebook: @embarkpropertymanagementllc
Email: info@embarkpropertymanagementllc.com
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