Part 2: Tips for working with out of state contractors

Dec 4, 2025

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Hiring contractors is hard enough… hiring them out of state can feel terrifying.

In this value-packed episode of Cashflow Positive, Kenny sits down with Jen Josey, real estate investor, coach, mastermind leader, and construction expert, to break down exactly how to find, vet, manage, and protect yourself when working with contractors in markets where you don’t live.

Jen shares the six critical documents every investor should use, the insider process for finding investor-friendly contractors (hint: it’s not Google), how to structure payment schedules that protect your budget, and the legal tools that saved her from a lawsuit.

If you plan to renovate a property outside your local market, this conversation may literally save you thousands.

Timestamped Highlights

[00:00] Meet guest Jen Josey and her path from teacher → corporate → real estate

[00:01:20] How Jen replaced her corporate income in 8 months

[00:01:55] What Jen is working on today: coaching, STRs, investing, and running multiple companies

[00:03:00] Current STR portfolio: beach condo, Boone cabin, and plans for a micro-resort

[00:05:00] What Jen looks for: smaller STRs, pet-friendly, waterfront, couples-focused

[00:06:25] How she evaluates markets in NC, VA, and SC

[00:08:10] Kenny’s lead-in to contractor horror stories and out-of-state projects

[00:09:00] Jen’s #1 starting point: investor Facebook groups (and how to post correctly)

[00:09:45] Step 2: local REIAs (why they matter and what quality they attract)

[00:10:40] Window replacement sticker shock: a real example ($7K for three windows)

[00:12:00] Never pay large deposits upfront—and what to do instead

[00:12:45] The exact six critical documents every investor should use

[00:13:35] The “lien waiver” that saved Jen from being sued

[00:14:10] The contract: deadlines, penalties, warranties, and holding contractors accountable

[00:15:40] Insurance + indemnification: adding yourself to a contractor’s policy

[00:16:20] Building your scope of work from the inspection report

[00:16:55] Paying your inspector to verify contractor work

[00:17:40] The proper way to structure a payment schedule (why the final payment is the largest)

[00:18:55] W-9 requirements for anyone paid over $600

[00:19:20] Contractors who refuse to sign contracts—why you should walk away

[00:20:05] Kenny’s theater room story and how a missing change order cost him

[00:21:55] How to prevent “death by $500 change orders”

[00:23:15] How hard money lenders help enforce accountability

[00:24:00] What makes someone an investor-friendly contractor

[00:27:00] Jen’s secret weapon: “pimping out” contractors to keep prices low

[00:29:00] Code of Conduct on job sites (English + Spanish)

[00:33:00] The two most important people on your STR team: cleaners + handyman

[00:34:25] Paying your handyman well to secure long-term loyalty

[00:35:00] Jen’s final tip for cash flowing positive: deliver unforgettable guest experiences

[00:37:00] Why theme ≠ experience (Kenny’s Taylor Swift pillow story)

[00:39:20] Where to follow Jen and how to get her contractor documents

About the Guest

Jen Josey is a real estate investor, coach, podcaster, and founder of the Real Estate Investor Growth Network (REIGN). After leaving her corporate job, Jen built a diverse portfolio across long-term rentals, short-term rentals, flips, and new construction. She runs multiple companies under the Joli brand, including construction, brokerage, and investment arms, and coaches investors nationwide on buying and renovating out of state.

She is also the host of the Real Estate Investor Growth Network Podcast and leads a mastermind for active investors.

🔗 LinkedIn | Podcast | Website

Resources Mentioned

REIA (Real Estate Investor Association)
The Real Estate Investor Growth Network YouTube Channel (REIGN)

Mentioned Resources

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