Real Estate Rookie Escaping the 9-5 Grind with Just 2 Properties (in 2 Years!)
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Sep 29, 2025 Dylan Pettijohn, a savvy real estate investor, shares his inspiring journey from a W-2 job to owning 15 rental units in just two years. He details how he found off-market deals, successfully tackled DIY renovations, and used commercial financing to scale his portfolio. Dylan emphasizes the value of partnerships and innovative financing strategies, revealing how he negotiated a significant price drop on a 12-unit property. Gain insights on tenant management, strategic rent increases, and the importance of solid planning in real estate investment!
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How He Won A Pocket Listing
- Dylan got a pocket listing because he already had a relationship with the agent and clear buy criteria.
- The agent showed him a property before it hit the market and he put in an offer immediately.
Create A Precise Buy Box
- Build a concrete buy box by deciding strategy (house hack, STR, long-term) and expected return metrics.
- Underwrite dozens of deals to refine that buy box and know what a good deal looks like.
Offered Full Price Same Day
- After touring the triplex, Dylan offered full asking price that night because it fit his buy box and location goals.
- He prioritized getting the offer in immediately rather than waiting.
