Side Hustle Strategist – Deep Dive Playbook

Identity Snapshot
A cautious tester. The Side Hustle Strategist wants to dip a toe in, not cannonball. They measure success by “is this working without taking over my life?”

🔎 SWOT

• Strengths: Practical, flexible, grounded in reality.

• Weaknesses: Easily distracted, may never scale.

• Opportunities: Can leverage simplicity to build a foundation others overcomplicate.

• Threats: Giving up too early, or never leaving “side hustle mode.”

👥 Team Needs

• Property Manager (Keck & Co.) → so they don’t drown in tenant calls.

• Bookkeeper / VA (Keck VA) → to track cashflow, expenses, and make this feel “hands-off.”

• Local Realtor/Wholesaler → to feed them safe, beginner-friendly deals.

💰 Financial Priorities

• Keep 3–6 months of reserves for peace of mind.

• Focus on net cashflow after management — if it isn’t positive with systems in place, it isn’t worth it.

• Track return on time: how much effort = how much reward?

🧠 Mindset Shift

Move from “I don’t want this to take over” → “I can build freedom without losing balance.”

🚀 Scaling Strategy

1. First Property → safe, simple rental or turnkey.

2. Next 2–3 → duplicate model, no “exotic” plays.

3. 5+ → start looking at Strategy-First archetype strategies (BRRRR, JV, tax plays).

⚠️ Risk Watchlist

• Overpaying for convenience (bad turnkey deals).

• Staying too small — inflation will eat tiny returns.

• DIY’ing to save money → burns time, erodes confidence.

🏡 Ideal Deal Types

• Small turnkey single-family rentals.

• Condos or townhomes in stable neighborhoods.

• JV-lite deals where partner handles heavy lifting.

🔗 Investor Engine Integration

• Foundation Package → clarity and roadmapping.

• Property Management (Keck & Co.) → stress-free ownership.

• VA/Admin Support → to systemize early, so it feels like a real portfolio, not a burden.

👉 That feels like a blueprint someone could actually use, not just a personality profile.