Episode 758
Failing My Way to Success | Phillip Cantrell on Business, Mindset & Leadership
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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