The Moonlight Real Estate Side Hustles and Syndications Show

️ How to Build a Portfolio Slowly — One House at a Time — While Working a Demanding Job (With Jacob Carroll) 💼🏘

Eric Lindsey Season 1 Episode 157

Many investors feel pressure to scale fast — but Jacob Carroll proves the opposite. Despite a demanding full-time job, raising kids, relocating, and running a household, Jacob built his portfolio slowly and intentionally… one property at a time.

His philosophy: consistency beats speed, and you can build wealth without sacrificing your career, family, or peace of mind.

💼 How Jacob Invests While Working a Full-Time Job

Jacob still works a demanding W-2, so he relies on disciplined routines. He checks his buy box daily, runs numbers consistently, and targets just 1–2 properties per year — a pace that supports family life and financial stability.

He invests in Minneapolis/Twin Cities long-term rentals and is adding a short-term rental buy box for family visits. His strategy fits his life — not the other way around.

🏘️ A Recent Transaction: Minneapolis Long-Term Rental

After moving to San Diego, Jacob bought a Minneapolis rental through local agents, underwrote it remotely, and used a portfolio loan (25% down, 7.5% interest). His wife walked the property and filmed videos, and together they built a reno plan.

Jacob did two weeks of DIY work, then relied on his carpet installer, handyman, and local partners. The property was leased within a weekend.

📊 How Jacob Underwrites Rentals

Jacob’s top metric is payback time — not cash-on-cash. Inspired by Payback Time by Phil Town, he checks whether cash flow will repay his investment in 8–10 years.

His underwriting includes:
 • Purchase price
 • Down payment
 • Interest rate
 • Taxes, insurance, HOA
 • Utilities
 • Renovation budget + timeline

Higher rates may mean thin cash flow early on — and he’s okay with that if the fundamentals are strong.

🧹 Tenant Placement & Property Management Systems

Jacob’s “secret sauce” is property management. He:
 • Remodels units to B+/A- quality
 • Uses Zillow Rental Manager
 • Defines an ideal tenant profile
 • Sticks to clear criteria
 • Charges slightly higher rents to filter out poor leads

This results in low-maintenance tenants — especially important when managing remotely.

🧭 Moonlight Coaching Portion — Coaching Advice From Jacob Carroll

What Every New Investor Should Know
Real estate isn't passive. Get your financial house in order first: eliminate debt and build reserves.

How to Balance Business, Life, and Real Estate
Grow slowly. Start with a single-family home. Join local meetups to stay grounded when emotions run high.

If You Have Little Money or Time
House hack. Save 5–10% for your first place. Use your W-2 for momentum and partner with trusted people if needed.

Knowing Your Numbers
Keep clean bookkeeping, separate accounts, and get a mentor to review your numbers. “Measure twice, cut once.”

📚 Books Recommended for Active and Passive Investors

The ABCs of Property Management — Kim McElroy
A foundational guide to operations, customer service, and long-term management success.


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