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#427 How Raymond Plank Built a $50 Billion Oil Company

August 1, 2026

AI Summary

5 min read

A 90-Year-Old Entrepreneur's Operating Manual

Raymond Plank founded Apache Corporation in 1954 with $250,000. By the mid-2000s, that company was worth $50 billion. But the most interesting thing about his memoir, A Small Difference, is not the company history—it's that Plank kept a daily diary for 60 years and wrote the book at age 90, essentially distilling seven decades of entrepreneurial experience into a collection of maxims, beliefs, and hard-won principles. The book reads like a diary, and what emerges is a clear operating system for building a long-term business in a cyclical, capital-intensive industry.

The Relentless Mindset

Plank's entrepreneurial instincts showed up early. Growing up on a farm near Minneapolis, he sold eggs as a child, then moved into sawing down trees, stacking and selling firewood, and eventually extracting sap to boil into maple syrup—all before high school. He sold to local grocery stores and meat markets. His father praised his entrepreneurial endeavors and grounded him in values of integrity and a strong work ethic.

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What you'll learn

  • 1 Timestamped Outline
  • 2 (00:00) **Opening: Raymond Plank's Life Philosophy** - Introduction to Plank's memoir and the two cornerstones that shaped his life
  • 3 (03:02) **Why This Book Is Unusual** - Plank kept a daily diary for 60 years, and the book reads as a philosophy collection from a 90-year-old entrepreneur
  • 4 (05:36) **Mother's Death and the War** - The trauma of losing his mother at 15 and serving as a fighter pilot in World War II
  • 5 (08:01) **Relentlessness: Comparing Plank to Rockefeller** - Both men share a low-key but relentless approach to getting what they want
  • 6 (10:53) **Post-War Decision: Self-Employment** - Plank chooses a riskier path and identifies the post-war opportunity
  • 7 (13:14) **The Insight That Led to Apache Corporation** - Discovering the oil and gas investment opportunity through his accounting work

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Show Notes

Raymond Plank founded Apache Corporation with just $250,000 in 1954. 50 years later his company was worth $50 billion. This episode examines the life and entrepreneurial philosophy of Raymond Plank through his memoir A Small Difference Rather than presenting a conventional history of Apache, this episode focuses on the lessons, maxims, and beliefs Plank accumulated over seven decades in business. Written when he was nearly 90, the memoir reads like a lifelong diary of how to think about opportunity, courage, cost control, resourcefulness, and adaptation. Lots of wild stories in this one. Made possible by: Ramp: ⁠⁠⁠https://ramp.com⁠⁠⁠ Applovin: ⁠⁠⁠https://www.applovin.com⁠ Vanta: ⁠⁠⁠https://vanta.com/founders⁠ ⁠Add your email here⁠ and I will send you my top 10 quotes from every episode: https://davidsenra.substack.com

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