From Pepsi Routes to Real Estate Millions: Rob Weissman’s Journey | Real Estate Hacking Live

Rob Weissman shares his inspiring journey from selling Pepsi products to becoming a successful real estate investor, developer, and title partner. In this deep-dive conversation, he reveals how he got started with Carlton Sheets tapes, learned short sales during the mortgage crisis, and scaled into flipping, new construction, and eventually building to rent.

Learn how creative problem-solving, persistence, and building strong relationships fueled his success — and why he believes sustainability and long-term wealth come from staying in the game.

00:00 – Introduction & meeting real estate mentors
01:30 – Discovering Carlton Sheets and early inspiration
03:00 – First steps in mortgages & quitting Pepsi
05:00 – Learning the title side of real estate
06:30 – Boiler room training & building sales confidence
10:00 – Transition to mortgage brokering & relationships
12:00 – Mortgage crisis & learning short sales
15:00 – Creating a short sale niche and teaching classes
18:00 – First flips, moving houses, and creative deals
23:00 – Scaling into new construction
25:00 – Realization about wealth building & build-to-rent strategy
27:00 – Building duplexes and multifamily projects
30:00 – Lessons from challenges in development