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Guide to Sober Living Real estate Investing

How Do You Successfully Transition and Scale a Rental Portfolio with Short-Term Rentals, Sober Living, and Automation?

Podcast Episode: The Real Estate Investing Club with Gabe Petersen & Guest: Brian Tibbs (The Unexpected Investor)

Featured Snippet-Style Answer

To transition and scale a rental portfolio using short-term rentals, sober living homes, and automation, focus on evaluating your existing assets for alternative uses, leveraging technology for management, building specialized teams, and diversifying property functions—all while emphasizing market demand, operational efficiency, and strong support networks.

1. What Inspired a Rental Portfolio Shift Toward Short-Term Rentals and Sober Living?

Summary:
The shift began out of necessity when traditional rentals didn’t meet the owner’s evolving needs and new market opportunities like Airbnb presented higher profitability. For sober living, meeting both community needs and investor objectives inspired the transition.

“We decided to test out three of our units and within three months we’d flipped our entire portfolio over to short-term rentals … because it was performing so much better than long-term rent.” —Brian Tibbs

In-Depth:
Initially built on traditional rentals, Brian discovered the limits of long-term tenants—especially when overseas. Encountering a flooded house and a lack of suitable Airbnb options catalyzed testing short-term rentals, which soon far outperformed the old model. Years later, exposure to the unique needs and strong demand of sober living through his investor network led to diversification, adding both a social impact and a dependable income stream.

2. How Do You Transition from Long-Term Rentals to Short-Term Rentals or Sober Living?

Summary:
Begin by testing a few units, furnishing them for short-term guests, and updating management processes. For sober living, partner with experienced operators and ensure proper licensing and programming.

Actionable Steps:

  • Evaluate which properties perform poorly as long-term rentals.

  • Renovate and furnish selected units, create attractive listings, and leverage platforms like Airbnb.

  • Build relationships with experienced sober living operators for co-living style conversions.

  • Focus on compliance—ensure local zoning, fair housing, and program structure for special needs housing.

“In 2016, pretty much you could just get anything, take your iPhone, take a photo, and it would rent out … But we began to 1031 exchange into other properties that were better short-term rentals throughout the process.” —Brian Tibbs

3. What Does It Take to Scale and Automate Property Management Operations?

Summary:
Building a capable local and remote team, leveraging specialized property management and automation software, and creating standard operating procedures are critical to growth.

Key Points:

  • Remote management works best with strict systemization and the right hires: cleaning, handyman, remote virtual assistants/customer service.

  • Use tech for digital locks, pricing, agreements, and messaging.

  • Delegate routine functions; spend minimal weekly hours on oversight and high-level decisions.

“I built a business that would pay its own bills and I wasn’t giving my time away for free. … I spent maybe five hours a week, just kind of keeping an eye on things, answering the bigger questions …” —Brian Tibbs

4. What Unique Opportunities (and Challenges) Come with Sober Living Investments?

Summary:
Sober living investments blend social impact and cash flow, but success requires strong partners, tailored resident programs, and clear boundaries between real estate and service operations.

Principles:

  • Partner with operators with established reputations.

  • Properties should be large (2,500+ sq ft), adaptable for shared living.

  • Rules: no drugs/alcohol, accountability programs, peer leaders in each house.

  • Primary rent source is residents; some assistance from charity/government/Medicaid is possible.

“Over 90% of our rent is collected directly from our tenants … We’re investing in the real estate from the real estate side, but we’re also providing a service that’s just at break even for the residents.” —Brian Tibbs

5. What Strategies Help Real Estate Investors Find (and Fund) New Opportunities?

Summary:
Relationship-building with wholesalers, sticking to known markets and asset classes, and using creative partnerships or syndications to grow are key.

  • Wholesalers and trusted contacts generate the best, targeted leads.

  • Partnerships and syndications expand investing capacity across multifamily, short-term rentals, and sober living.

  • Stick to what you know; avoid unrelated development projects unless highly experienced.

“I’ve settled in. I’ve got several wholesalers here in the Phoenix area that know exactly what I’m looking for… I’m willing to pay them the $10,000 or $15,000, which I would have paid in marketing expenses anyway, to just get this stuff handed to me on a platter.” —Brian Tibbs

6. What Are the Biggest Lessons—and Mistakes to Avoid—When Scaling a Real Estate Portfolio?

Summary:
Start early, add new units consistently, and do not jump into unfamiliar asset classes or development without preparation.

“Stick to your goal of adding a unit or more every year… Make your money in the market that you understand and the asset class that you understand and then take that money and then go play with it. Don’t try to mix the two things together.”—Brian Tibbs

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7. What Market Trends and Best Practices Should Today’s Investors Watch?

Summary:
Favor landlord-friendly, high-growth markets (example: Texas and Phoenix). Embrace tech, community, and education—books like Rich Dad, Poor Dad remain foundational, but execution wins.

Expert Quote:

“If you have not completed your first deal yet, this is your kick in the pants, go out there, get it done. Every market is a challenge. But yeah, I would have told myself to stick to that one unit at least per year, if not more.” —Brian Tibbs / Gabe Petersen

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