Rebuilding After Losing $550K in His Real Estate Business with Caleb Luketic

What happens when your business loses over half a million dollars—and it’s your own fault? In this episode, I’m joined by my good friend and client Caleb Luketic, who shares how he climbed out of a $550K loss through strategy, grit, and knowing his numbers. We dive deep into the raw, behind-the-scenes reality of being on the brink—and how clarity, accountability, and CFO support helped him rebuild a thriving business in just 18 months.

Caleb doesn’t just talk about the comeback. He reveals the specific shifts in strategy that saved his business—like choosing assignments over flips, getting creative with owner financing, and radically narrowing his marketing focus to only what worked. If you’re in real estate and feeling overwhelmed, this episode will show you it’s not just possible to turn things around—it’s profitable.

Episode Timeline

[0:00] – Introduction

[2:05] – Caleb’s background in marketing and how it evolved into real estate investing

[5:50] – How poor decisions and bad hires led to $550K in losses

[8:30] – Facing the choice: bankruptcy or bounce back

[10:20] – The 18-month payoff plan and how data made all the difference

[12:00] – Why gut decisions nearly sank the business—and what saved it instead

[14:10] – Flipping vs. wholesaling: how choosing cash now won the long game

[16:00] – The $80K wholesale assignment that cleared the final debt

[18:15] – New challenges: when the market shifts mid-flip

[22:40] – Why Caleb is moving away from flips to owner financing and wholesale

[24:00] – The emotional difference between retail buyers and owner-financed buyers

[28:00] – Caleb’s marketing agency focus: SEO, PPC, and Meta ads

[30:20] – Real ROI breakdowns for marketing channels

[32:00] – Why you need someone to help you pivot—before it’s too late

5 Key Takeaways

1. Losing money isn’t the end—lack of strategy is. Caleb turned a $550K loss into a growth story by facing the numbers head-on.
2. Wholesaling brought the cash flow flipping couldn’t. Fast assignments became the engine for rebuilding his business.
3. Marketing without data is dangerous. Narrowing efforts to what worked (and ditching what didn’t) saved thousands.
4. You must pay off the emotional debt too. Caleb shares how personal shame nearly sidelined his comeback.
5. You don’t need more leads—you need more clarity. Profit First helped Caleb make smarter decisions and recover with purpose.

Links & Resources

• Connect with Caleb Luketic: www.calebluketic.com
• Learn more about Profit First implementation: www.simplecfo.com

If this episode inspired you, helped you, or made you rethink your strategy—don’t forget to rate, follow, and share the show. Your reviews help more real estate investors discover the Profit First for REI podcast. Let’s keep growing together!