Caleb Pearson: Active vs. Passive Income & Why You Can’t Skip Steps in Real Estate Investing

In this episode of Burning the Ships, I sit down with my friend Caleb Pearson, a Charleston-based real estate investor who’s built an impressive empire through brokerage, fix-and-flip, multifamily, and hard money lending.

Caleb shares his journey from selling 100 homes in his first 18 months, to flipping 75–100 properties a year, to building a diversified portfolio of multifamily and mobile home parks. We also dive into how he structures his lending fund, why mentorship has been the backbone of his growth, and how he’s learned to build small but powerful teams that drive results.

If you’re an entrepreneur or investor looking for inspiration on scaling smart, leveraging mentors, and keeping resilience at the core of your business, this conversation is packed with strategies and real talk.

Key Talking Points of the Episode

00:00 Introduction

01:28 JJ’s Joke of the Week

03:15 Caleb’s roots in Virginia and move to Charleston

04:00 Breaking into real estate sales: 100 homes in 18 months

05:08 Discovering flipping and wholesaling through a chance call

06:11 Entering multifamily and mobile home parks: mentorship from Tim Bratz and Corey Peterson

07:19 The launch of his hard money lending fund that’s now at $10M+

09:14 Why mentorship is the shortcut to scaling faster

11:47 Balancing entrepreneurial curiosity with focus

13:33 Building small, high-performing teams vs. managing large ones

15:14 Creating culture, casting vision, and using incentives

18:10 Why golf and country clubs are underrated networking tools

20:00 The ROI of social media and brand awareness

23:24 Market insights: Charleston’s boom, current stabilization, and future outlook

26:51 Why his lending fund may be the most scalable business arm

29:42 Property management headaches and why he outsources

31:15 The vision for the future and why he’ll never fully “retire”

33:06 Managing chaos: the importance of team members who balance you out

37:08 Harnessing entrepreneurial energy and finding gold in the chaos

38:23 Practical advice for newbies: start small, find mentors, keep your W2

39:14 Active income vs. passive income—why you can’t skip steps

42:11 Structuring and scaling a lending fund with automation

47:17 Growing capital commitments and scaling past $20M

50:50 Legacy, resilience, and what Caleb wants to be remembered for

Quotables

“I would just highly encourage somebody to go spend two days with someone you look up to in the business. Don’t just dive in blindly.”

“We spend at least a hundred grand a year on education and masterminds. But it means nothing if you’re not implementing.”

“If you’re not getting kicked in the teeth every week, you’re probably not pushing hard enough.”

Links

Caleb Pearson

https://www.facebook.com/caleb.pearson.583

https://www.instagram.com/calebpearsonre

608B Capital

https://608bcapital.com