In this special reunion-style conversation, John sits down with long-time coaching client, elite agent, and real estate investor Caleb Pearson to unpack his journey from being broke to building a multi-pronged real estate enterprise — including a top-producing real estate team, a house-flipping machine, and a growing portfolio of cash-flowing rental properties and multifamily assets.

• Learn how to build multiple streams of income in real estate

• Transition from transactional income to long-term wealth

• Leverage listings, fix-and-flips, and buy-and-hold strategies

• Structure your business for profitability and lifestyle

• Use systems, accountability, and mindset to outperform the market

Caleb reflects on how he and his brother and cousin shared a two-bedroom apartment, furnished it with items from Goodwill, and used pure grit to build their real estate careers from scratch — cold-calling expireds and FSBOs with military-level discipline and zero excuses.

Hear how Caleb applied The Miracle Morning routine, daily sales training, and 7 AM prospecting blocks to build a scalable, productive real estate business rooted in structure and consistency.

A pivotal story where Caleb brought an off-market deal to a local flipper, made $3K in commission — and watched the investor net six figures. That moment flipped the switch: “I’m sitting on the wrong side of the table.”

Learn why Caleb believes the best wealth is built by owning assets, not just flipping them. He breaks down how to transition from active income (commissions and flips) to passive income through rental properties, cost segregation studies, and leveraging tax strategy.

Find out how Caleb structures his flipping business to buy 5–10 homes per month, what roles you need to hire (construction manager, acquisitions, closing coordinator), and how to gradually increase your marketing budget while tracking every dollar and metric.

After a decade at RE/MAX, Caleb reveals why he made the switch to eXp — not for the splits, but for the community, collaboration, stock incentives, and proximity to elite minds like John Kitchens, Jay Kinder, and Al Stasek. Learn how he's using rev share as a retention tool for his team and aligning with top producers for ongoing growth.

• The ONE rental property strategy any six-figure agent can follow

• How to partner with seasoned investors (even on your first deal)

• Direct mail tips, cost-per-lead expectations, and conversion math

• Why control, not commissions, equals true financial freedom

• The psychology of sellers choosing a “cash as-is” offer over a traditional listing — and how to ethically and profitably serve both
  
  

• How Caleb keeps top team members for 10+ years

• Transitioning to a team brand (CP Team) instead of a personal one

• Empowering agents to build wealth, not just sell homes

• What he’s most excited about in 2025 — new construction, brand refresh, and legacy-building

• Realtors earning $100K+ who want to build wealth

• Team leaders looking to add investing as a profit center

• New or experienced real estate investors

• Entrepreneurs who value time, systems, and leverage

• Anyone tired of the transactional treadmill

“Track every dollar. Know your cost per deal. Marketing without metrics is just a guess.” - Caleb Pearson

• Instagram: @johnkitchenscoach
• LinkedIn: @johnkitchenscoach
• Facebook: @johnkitchenscoach

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