$200M+ in Deals, 5 Business Arms, and 1 Game-Changing MLS Tool featuring Caleb Pearson

In this episode of the Collective Genius Podcast, I had the pleasure of catching up with Caleb Pearson—real estate investor, software creator, and master delegator from Charleston, South Carolina. From closing short sales at the bottom of the market to building a diversified real estate empire, Caleb walks us through his entrepreneurial evolution. We explore his early success in retail, his bold leap into flipping and multifamily investing, and how mentorship and community shaped each step of his path.

 

We also dive into his latest ventures: creating a software tool that automates thousands of MLS offers and launching a lending fund that fills a crucial gap for local flippers. If you’re a wholesaler navigating new legislation, a retail agent looking to pivot into investing, or an operator trying to scale, Caleb’s story is filled with actionable wisdom you won’t want to miss.

 

Episode Highlights:

[0:00] - Introduction

[2:22] - From college basketball to Charleston real estate: Caleb’s unexpected career start

[5:19] - The mentor who saw potential and the lessons Caleb absorbed early

[9:58] - The $3,000 commission that revealed he was sitting on the wrong side of the table

[11:02] - Visiting top producers and joining CG: how Caleb fast-tracked his investment knowledge

[15:35] - The napkin math that made multifamily underwriting click

[20:44] - Buying the wrong type of properties: lessons learned the hard way

[24:00] - Why mobile home parks are now Caleb’s preferred asset class

[30:04] - Building a tool to automate 3,000 MLS offers—chaos and opportunity

[36:30] - Getting creative and softening lowball offers to build relationships with agents

[41:30] - Starting a private lending fund: where the idea came from and how it works

[44:00] - South Carolina wholesaling legislation and its ripple effect on the market

[47:01] - The cashflow lag from losing wholesale income—and how to prepare for it

[50:09] - Sticking to the numbers, no matter how tempting the deal looks

[51:05] - Delegation as a superpower: how 80% effort beats burnout every time

 

5 Key Takeaways:

 

1. Mentorship and execution matter more than innovation. Caleb credits his success to following a seasoned mentor’s guidance to the letter—and it paid off quickly.

2. Wholesaling and flipping require different cash flow strategies. With new legislation in SC, Caleb shares how losing wholesale income impacted his business and how he adapted.

3. Buy boxes are non-negotiable. Stretching beyond proven deal criteria almost always leads to problems—discipline protects your team and your bottom line.

4. Automation opens doors. The MLS offer tool Caleb built now helps investors uncover motivated sellers with less manual effort and greater reach.

5. Capital is raised through relationships. By joining country clubs and attending charity events, Caleb put himself in the right rooms—and raised millions by being consistent and trustworthy.

 

Links & Resources:

• Join the CG community: theCGPodcast.com

 

If you enjoyed this episode, be sure to rate, follow, and leave a review—and share it with a friend who’s ready to level up in real estate!