$200,000 used to feel like a powerhouse investing budget… but in today’s short-term rental landscape, it doesn’t go nearly as far as it used to.

In this solo episode, Kenny Bedwell breaks down the hard truth: $200K is the new $100K.

Competitive STR markets have leveled up, amenities have escalated, and investor expectations have shifted. Kenny walks through why $200K no longer guarantees entry into the big-boy markets (Smokies, Bradenton, Asheville, Bourbon Trail), what buyers consistently misunderstand about down payments vs. true budget, and how to think like a strategic investor rather than a pre-approval chaser.

He also unpacks the 20% Rule, the reality of amenity wars, why your biggest moat is future thinking, and the path newer investors should take when they have less than $200K to deploy.

If you want to make your money actually work and stop getting crushed by competition, this episode is your roadmap.

[00:00] Why $200K doesn’t stretch like it used to

[00:01:20] The psychological trap of buying based on pre-approval

[00:02:10] The 20% Rule: what your true budget actually is

[00:03:20] Why a $500K home can require $200K to do it right

[00:04:40] Competitive markets and the real cost of keeping up

[00:06:00] When big brokerage agents start pushing a market… it’s already too late

[00:07:20] Why chasing what worked last year won’t work now

[00:08:10] Downsizing: why a killer 2–3 bedroom beats an underfunded 6-bedroom

[00:09:20] The amenity war: pickleball courts, splash pads, heated pools, full design

[00:10:50] Real estate finance lesson: why abnormal returns disappear

[00:11:40] Today ≠ 2021: why $200K no longer buys performance

[00:12:25] How to pick markets with lower barriers of entry

[00:13:10] What “drivable markets” really are and why they outperform

[00:14:35] How to read metropolitan travel patterns for hidden gems

[00:15:40] Why most investors are psychologically wired to overleverage

[00:16:20] The only way to compete with bigger players

[00:17:50] Planning for future competition, not past comps

[00:18:30] Kenny’s Walkins Glen example: $350K → $144K gross

[00:19:30] Why futuristic thinking builds moats

[00:20:10] The Autopilot app story (Nancy Pelosi portfolio tracking)

[00:22:15] Understanding how investor flood-ins flatten returns

[00:23:20] How to pick properties that will hold up against new competition

[00:24:30] If you want a moat, you must create it

[00:25:10] Kenny’s offer to break down “moat categories” in a future episode

[00:25:50] How to message Kenny directly with questions

• Autopilot App (stock trading tool tracking politician trades)

• Want us to find the deals for you? https://strinsights.com
• Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df
• Instagram – @kenny_bedwell
• YouTube – Cash Flow Positive
• LinkedIn – Kenneth Bedwell

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

Most people get into real estate for freedom, but what happens when the money isn’t enough?

In this powerful episode of Cashflow Positive, host Kenny Bedwell sits down with Caleb David, a commercial real estate broker, investor, and longtime nonprofit leader whose story goes far beyond deals, commissions, and spreadsheets.

Caleb opens up about his early years growing up in a strict environment, his burnout in the nonprofit world, and the leap of faith that brought him into commercial real estate. He also shares candidly about nearly going bankrupt, rebuilding from scratch twice in the same year, and discovering what it really means to live a life of purpose.

The deeper theme of this episode: Real estate might bring wealth… But purpose and service bring fulfillment.

Caleb’s work with Crazy Love Africa, his time in Ethiopia, his worldview shaped by humanitarian work, and his approach to “creating space and building community” give listeners a new way to think about success, impact, and the life they’re building.

This conversation is grounding, challenging, and wildly inspiring.

[00:00] Meet Caleb, from conservative upbringing to nonprofit burnout

[00:01:50] The leap into commercial real estate and surviving on commission

[00:03:00] Becoming Rookie of the Year during a recovering market

[00:04:20] Why Caleb doesn’t specialize and how sectors overlap (retail, industrial, STR + commercial combos)

[00:05:10] COVID’s impact on the industrial + retail markets

[00:06:20] How STR investors can begin learning commercial real estate

[00:07:00] The value of curious brokers, not “know-it-alls”

[00:09:20] Why empathy belongs in real estate

[00:10:30] The theme of “creating space, building community”

[00:11:00] Looking beyond money — purpose, faith, and fulfillment

[00:12:10] Caleb’s global nonprofit work in Ethiopia and the Middle East

[00:14:15] The dangers of “savior mentality” when giving

[00:15:40] Introducing When Helping Hurts (book)

[00:16:25] Supporting women with HIV in Uganda through Crazy Love Africa

[00:17:25] Microgrants: $500 that changes a family’s future

[00:18:10] Fair-trade crafts made by women artisans

[00:19:00] How giving time can matter more than giving money

[00:20:00] Letting go of ego + redefining impact

[00:21:30] How to find nonprofits that align with your values

[00:23:45] Using 990 forms to evaluate nonprofit transparency

[00:25:50] How Caleb balances business, service, and personal well-being

[00:27:00] Why rest makes you more productive

[00:28:20] Healing from trauma and overcoming near-bankruptcy

[00:30:10] Taking “the next right step” in real estate and life

[00:33:15] Caleb’s final advice to ambitious professionals

[00:34:20] How to connect with Caleb + where to learn more

Caleb David is a commercial real estate broker, investor, podcaster, and humanitarian based in Colorado. With a background that spans 20+ years in the nonprofit sector, global humanitarian work in Ethiopia and the Middle East, and nearly a decade in commercial brokerage, Caleb brings a rare blend of business expertise and deep-purpose leadership.

Today, he serves clients across the Colorado market through Keller Williams Commercial while also serving on the board of Crazy Love Africa, an organization supporting women and children impacted by HIV in Uganda. His mission: create space, build community, and leave a meaningful impact both locally and globally.

🔗 LinkedIn | Instagram |

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.

[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

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.

🔗 LinkedIn | Website | Facebook | Instagram | X | Behind Every Stay...