Phillip Cantrell shares how failing his way to success led to building Benchmark Realty and a 40-year career filled with lessons on mindset and leadership.

In this episode of RealDealChat, Jack Hoss interviews Phillip Cantrell, founder of Benchmark Realty and author of Failing My Way to Success, to uncover decades of wisdom from his entrepreneurial journey — from commercial printing to building one of the fastest-growing real estate brokerages in the U.S.

Phillip explains why treating real estate as a business, not a hobby, is key to lasting success. He shares his “4 Cornerstones of Business Success,” lessons from losing and rebuilding multiple companies, and the mindset shift that transforms failure into a foundation for growth.

You’ll learn:

• Why most entrepreneurs fail (and how to avoid it)
• The truth about treating real estate as a real business
• Phillip’s 4 Cornerstones of Success: Work Hard, Observe, Delegate, and Show Compassion
• Why “repeatable processes lead to repeatable outcomes”
• How cross-industry learning fuels innovation
• The dangers of comfort zones and fear-based decision-making
• How to overcome self-doubt and lead with authenticity
• The importance of writing goals and working on the business, not in it

📘 Grab Failing My Way to Success → PhillipCantrell.com

📗 Download a free chapter → PhillipCantrell.com

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⏱️ Timestamps

00:00 – Failing my way to success: lessons learned

01:00 – Why real estate must be treated like a business

02:20 – From commercial printing to real estate investing

04:00 – Building Benchmark Realty and growing to 2,000+ agents

05:10 – Writing the book to guide future entrepreneurs

06:00 – The 4-4-2 business record: wins, losses & ties

07:20 – Why businesses fail: lack of problem-solving scale

09:00 – How early failures shaped his leadership philosophy

10:45 – The Four Cornerstones of Success explained

12:10 – Working hard, delegating, observing, showing compassion

13:30 – Cross-pollinating business ideas from other industries

15:10 – Writing things down & documenting processes

17:00 – Getting out of your comfort zone to grow

18:30 – Fear, authenticity & the power of being real

20:10 – Social media, comparison & the “attack of the naysayers”

22:10 – Outgrowing your environment and handling criticism

23:30 – Overnight success myths and building strong foundations

24:20 – Goal-setting and the importance of writing things down

26:00 – Why most people don’t plan — and how to fix it

27:30 – The daily writing habit that grows income

29:00 – Rapid fire: biggest lies, lessons & books

31:00 – Why documenting processes frees you to lead

33:00 – Final advice & where to learn more

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