The Moonlight Real Estate Side Hustles and Syndications Show
We show working professionals and busy people how to invest in real estate as a side hustle or a full-time business. We interview guests who have successfully started real estate businesses part-time and have turned them into full-time enterprises, or have generated passive income for themselves. This show will also demonstrate how to invest in real estate with low or no money. You will learn how to achieve success in various niches within real estate, including wholesaling, fix and flip, BRRR (Buy, Rehab, Rent, Refinance), and syndicating commercial real estate.
The Moonlight Real Estate Side Hustles and Syndications Show
From Fear to Freedom: Andrew Freed’s Honest Take on Exiting the W-2 and Leveling Up
Most people think you must quit your job to succeed in real estate, but Andrew Freed proves otherwise. From using a HELOC on his Boston condo to scaling 240+ units, he shows how W-2 professionals can balance careers while building wealth through multifamily, syndications, and creative financing.
📘 From W-2 to 240+ Units
Andrew started as a project manager on the W-2 path. During COVID, Rich Dad Poor Dad sparked a mindset shift. Realizing his net worth was tied to one condo, he tapped a $200K HELOC, house-hacked, JV’d into small multifamily, and expanded into syndications—growing from 30 to 240+ units in 3.5 years.
⏳ Investing While Keeping a W-2
Andrew focused on time management with 7 Habits, prioritizing urgent/important tasks and cutting wasted hours. He used his W-2 income to qualify for loans and house hacks, building bank credibility. His advice: don’t rush to quit—use your job as leverage.
🏘️ A 39-Unit Deal
In Worcester, a 39-unit portfolio projected $1.5M equity but hit turbulence when a bank changed terms, demanding a full year of reserves in escrow. Andrew pivoted to private lending, closed in weeks, and is stabilizing for a $7M refinance. Lesson: even “perfect” deals need flexibility, creativity, and strong partnerships.
💡 Rules Before Quitting Your Job
- Target ~2× monthly overhead—cash flow is lumpy.
- Keep active income—flips, brokerage, lending, side hustles.
- Don’t rush—Andrew delayed leaving his W-2; opportunities grew after, but the transition was tough.
- 🎯 Key Takeaways
- Start with house hacks, duplexes, or small multifamily.
- Use your W-2 to qualify—banks value steady income.
- Build systems early—processes save time and allow scale.
- Delegate low-value tasks to focus on high-dollar activities.
- Partnerships accelerate growth—bring time, money, or expertise.
- 🧭 Coaching Round
- For New Investors: Define goals—active (finding deals, raising capital) vs. passive (providing capital).
- Balancing Career & Family: Double down on strengths—analysis, networking, or ops. Passion sustains energy.
- If Starting Small: Network nonstop, join masterminds, add value via underwriting, sourcing, or raising capital.
- Why Passive Investing Works: Steady cash flow, diversification, and tax benefits like cost segregation (consult a CPA).
- 📚 Books
- Mindset — Carol Dweck
- The Hands-Off Investor — Brian Burke
- 10x Is Easier Than 2x — Hardy & Sullivan
- 📚 Final Thoughts
Andrew Freed proves you don’t need to quit your W-2 to thrive in real estate. By leveraging time, systems, and partnerships, he turned a condo HELOC into 240+ units. His journey—both wins and setbacks—offers a roadmap: don’t chase job security, chase financial security.
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