Part 2: You MUST Innovate in the STR space

Nov 13, 2025

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Innovation isn’t just about building something new; it’s about building something better.

In this episode of Cash Flow Positive, host Kenny Bedwell sits down with Juliano Silva, a full-time short-term rental investor and designer who’s built a portfolio of standout “signature properties” across multiple U.S. markets. From his early beginnings renting out a spare bedroom in Minnesota to creating high-performing STRs in Florida, Juliano shares how data, creativity, and intention fuel his approach to innovation.

They discuss the art of designing properties that can’t be copied, why standing out takes more than adding a pickleball court, and how to create guest experiences that drive both profitability and longevity. Juliano also opens up about building his own construction and design team, the value of experimentation, and how he protects his creative work while staying one step ahead of imitators.

If you’ve ever wondered how to make your STR truly unforgettable, this conversation is your blueprint.

Timestamped Highlights

[00:00] Meet Juliano Silva – From web developer to full-time STR investor

[00:01:30] The accidental first Airbnb: renting a bedroom in Minneapolis

[00:03:40] Early lessons in regulation and risk

[00:05:00] Transitioning from long-term rentals to short-term opportunities

[00:07:00] How COVID opened the door to their first real STR in Sarasota

[00:09:00] Turning a distressed property into a six-figure rental

[00:10:00] Building an in-house design and renovation team from scratch

[00:11:30] From experimentation to intentionality – creating “signature properties”

[00:14:20] The first pickleball court in Sarasota-Bradenton

[00:15:30] Using Google Trends and data to innovate amenities

[00:17:30] Why copycats will never win and how to stay ahead through originality

[00:19:00] Innovation as a mindset, not just a feature

[00:21:00] Designing for brand identity and guest retention

[00:23:00] Balancing appreciation and cash flow in every investment

[00:24:20] How Juliano protects his designs (and his energy)

[00:27:00] Drawing inspiration from international design and hospitality

[00:29:30] Innovating the guest experience with continuity and theme

[00:32:00] The E.R.O. Formula: Acquisition, Experience, Revenue, Operations

[00:37:00] Innovation as problem-solving like early check-in strategies

[00:39:30] Competing through service, not just price

[00:43:00] Juliano’s top advice: “When they zig, you zag.”

[00:45:00] Staying true to your fundamentals and cash flowing positive

About the Guest

Juliano Silva is a full-time real estate investor, designer, and founder of Behind Every Stay, a newsletter and consulting platform that helps investors create profitable, guest-loved short-term rentals. Based in California with properties across Florida, Minnesota, and North Carolina, Juliano has spent more than a decade in real estate, transitioning from long-term rentals to building data-driven, experience-focused STRs he calls “signature properties.” His approach blends creativity, analytics, and brand identity, helping investors think beyond amenities and build lasting value through intentional design and innovation.

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Cash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights and Podcast Your Brand. Production and editing by Podcast Your Brand.