$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...

If your short-term rental looks the same as it did three years ago, you’re already falling behind.

In this episode of Cash Flow Positive, host Kenny Bedwell explains why innovation isn’t optional. It’s the only way to stay competitive in a rapidly evolving STR market. From hotel refresh cycles to new amenity trends, Kenny breaks down how to model what the pros do and apply it to your own properties.

He shares real examples of how top operators are staying ahead, from custom pickleball-court designs and splash pads to unique features like three-sided golf simulators and container pools, and why the hosts who think three to five years ahead always win.

Learn how to build your own “moat,” create long-term value, and keep your listings at the top of the market.

[00:00] Why every STR owner must think like a hotel brand

[00:01:00] The hotel renovation cycle and what it teaches hosts about innovation

[00:02:00] Sneak peek: Kenny’s live event in New Orleans (Feb 28 – Mar 1) on scaling beyond STRs

[00:04:30] The hidden power of staying ahead of your competition

[00:07:00] Thinking long-term three- to five-year reposition cycles

[00:08:30] Why copying others’ amenities is a race to the bottom

[00:09:40] The “Fab Five” amenities and how to make yours stand out

[00:12:45] How Kenny’s $40K three-sided golf simulator became a game-changer

[00:15:30] New trends: designer pickleball courts, splash pads, and beyond

[00:17:30] Building room for future upgrades into every property

[00:18:40] How one container pool added $60K in annual revenue

[00:20:35] When it’s smarter to innovate than to buy another property

[00:21:20] Lessons from hotel design and guest experience

[00:22:45] Practical ways to stay “top dog” in your market

• Attend Kenny’s Live Scaling Event (Feb 28–Mar 1, New Orleans)

• 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 and Podcast Your Brand. Production and editing by Podcast Your Brand.

You don’t have to stop at single-family short-term rentals. You can build the systems and businesses that help others scale, too.

In this episode of Cash Flow Positive, host Kenny Bedwell sits down with Tyler Gruskiewicz, a full-time real estate investor and entrepreneur from Louisville, Kentucky. Tyler shares his journey from leaving a W2 job to building a growing portfolio of STRs, boutique hotels, and vertically integrated businesses, including a cleaning company, renovation arm, and property management service, all designed to solve the pain points he faced as a host.

They dive into the mindset shifts needed to scale sustainably, the lessons learned from operational chaos, and the power of turning real problems into real opportunities. Tyler also reveals his latest project: transforming one of Kentucky’s oldest bed-and-breakfasts into a mission-driven property supporting veterans and children with speech challenges.

If you’ve ever felt “stuck” at the single-family level, this conversation will show you how to think and build bigger.

[00:00] Meet Tyler: From Ohio roots to full-time investor in Louisville

[01:00] Growing a 7-property STR portfolio + hotels in Florida and Missouri

[02:00] What vertical integration really looks like for real estate investors

[05:00] Faith Renovations and Signature Stays: turning problems into services

[07:00] How Tyler built cleaning, install, and property management teams

[08:30] The cleaning nightmare that pushed him to start his own company

[13:00] Why checks and balances matter in STR operations

[17:00] How one bad turnover led to a total systems overhaul

[21:00] Building culture, communication, and shared vision inside your team

[25:00] The importance of purpose-driven leadership

[29:00] Turning early check-ins into new revenue and guest satisfaction

[32:00] The story behind Kentucky’s oldest B&B—and how it became a mission

[36:00] Giving back to veterans and kids through real estate

[40:00] The takeaway: No one’s coming to save you—build the solution yourself

Tyler Gruskiewicz is a real estate investor known for owning several short-term rental properties in Kentucky with a proven track record in the short-term rental (STR) market. He has gained recognition through interviews and podcasts for his unique approach to growing wealth through STR investments, highlighting both the challenges and strategies for success in this niche real estate segment.​ In addition to his property investments, Gruskiewicz also owns and operates a renovation and cleaning company, leveraging his experience to support and scale his rental business. Recently, he expanded his real estate portfolio by purchasing a 29-door hotel in Branson, Missouri, indicating significant growth and diversification in his hospitality ventures.

🔗 LinkedIn | Website

• Want us to find the deals for you? https://strinsights.com
• Get Top Markers for STRs (2025) https://www.strinsights.com/top-investable-short-term-rental-markets-2025-report
• Instagram – @kenny_bedwell
• YouTube – Cash Flow Positive

What does “scaling” really mean for you?

In this episode of Cash Flow Positive, host Kenny Bedwell breaks down what it truly takes to grow beyond single-family short-term rentals and why the definition of “scaling” should be unique to every investor.

Kenny walks through his personal evolution from duplex house hacking to managing multi-unit portfolios, building a co-hosting business, and partnering with investors to acquire large-scale STRs and boutique hotels.

Along the way, he shares the mindset, strategies, and lessons that help hosts move from buying one property at a time to building a sustainable, scalable business model that fits their goals, not social media’s definition of success.

[00:00] Why “scaling” looks different for every STR owner

[00:01:00] Kenny’s early investing story, from house hacking to Airbnb

[00:04:45] How Buffalo, NY shaped his mindset on scaling and diversification

[00:06:30] Breaking through capital limitations with rental arbitrage

[00:09:00] The rise (and fall) of arbitrage and what works better now

[00:10:30] Scaling into co-hosting and property management

[00:11:45] The power of sharing your wins to attract partnerships

[00:13:40] How to start small but think like a business owner

[00:15:20] Diversifying across markets for long-term stability

[00:18:00] Leveraging other people’s money (OPM) to scale faster

[00:20:20] Building partnerships and equity deals with no capital invested

[00:22:00] Why hotels aren’t the only way to scale and how big STRs can outperform

[00:24:00] Choosing properties that match your goals, not trends

[00:25:15] The truth about hotel deals vs. high-performing STRs

[00:26:40] Redefining success and scaling on your own terms

[00:27:50] A look ahead: scaling through new business opportunities

• Launch Hosts by Kim Fitzpatrick - Example of scaling through services

• Want us to find the deals for you? https://strinsights.com
• Get Top Markers for STRs (2025) https://www.strinsights.com/top-investable-short-term-rental-markets-2025-report
• 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 and Podcast Your Brand. Production and editing by Podcast Your Brand.

What if your next short-term rental deal isn’t failing because of the numbers… but because of your reviews?

In this episode of Cash Flow Positive, Kenny Bedwell digs into the “curse” of review-driven real estate—how guest expectations, property condition, and first impressions can quietly make or break your returns. He breaks down the two sides of STR investing (real estate + hospitality), shares real-world examples from his own portfolio, and explains why operations and guest experience are just as critical as deal analysis.

You’ll learn what details guests really notice, how to find properties that support great reviews from day one, and the simple fixes that turn complaints into five-star ratings.

If you want your short-term rental to outperform the market, hit play and start thinking like a guest, not just an investor.

[00:00] Why Kenny “hates” reviews 4and how they shape investor behavior

[01:00] The two-headed monster of STR investing: real estate + hospitality

[02:30] Why being a great host directly impacts revenue

[04:00] How property age and updates influence guest satisfaction

[06:00] Lessons from a historic 1860s home that became a five-star stay

[09:00] The hidden cost of ignoring capital expenditures

[10:40] When old systems (like HVAC) destroy the guest experience

[12:00] How unfinished basements and outdated designs kill reviews

[15:20] External factors: neighbors, privacy, roads, and power lines

[20:00] Designing for privacy, accessibility, and comfort

[23:00] How to impress guests from the moment they arrive

[25:00] The power of small touches, like Kenny’s ice cream bar idea

[27:00] Why first impressions make or break your ratings

[30:20] The link between five-star reviews and long-term revenue

• 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 and Podcast Your Brand. Production and editing by Podcast Your Brand

If you’ve been chasing the next “get rich quick” shortcut in real estate… this episode is your reality check.

In this episode of Cash Flow Positive, Kenny Bedwell flips the script on fast money and exposes the truth about building real wealth through real estate. He shares insights from conversations with high-level investors: Those who buy $100M hotels and still play the long game and reveals why the biggest wins come from appreciation, tax strategy, and equity paydown, not just monthly cash flow.

You’ll learn the four true pillars of wealth in real estate, how to think like an investor instead of a speculator, and why repositioning your assets the right way can transform your portfolio faster than chasing short-term returns ever will.

Stop looking for overnight success. Press play now to learn how the smartest investors actually get rich with patience, data, and a long-term plan.

[00:00] Back from the flu and fired up about “get rich quick” myths

[01:30] The problem with chasing only cash flow

[03:35] Lessons from top-tier investors who buy $100M properties

[05:00] The four wealth pillars: cash flow, appreciation, tax savings, and equity paydown

[07:00] What “repositioning” really means and why it’s where wealth is built

[09:25] When cash flow should be your priority and when it shouldn’t

[10:30] Why high-income professionals invest differently (and what that means for you)

[12:30] How to calculate true ROI using total return, not just cash flow

[15:20] The mindset shift: stop chasing income, start building net worth

[18:30] Defining your investment goals before you buy your next STR

[21:15] How Kenny evaluates deals now and why forced appreciation beats “good enough”

• 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 and Podcast Your Brand. Production and editing by Podcast Your Brand