Work Ethic, Setbacks & Grit with Curtis Raymond

n this episode of Jack of Oil Trades, host Stephan Wilson sits down with Curtis Raymond — a former Ivy League and TCU football player turned heavy machinery sales rep. Curtis shares the raw, unfiltered story of how childhood lessons, athletic setbacks, and personal grit shaped the way he approaches business and life today.From tearing his labrum in high school, to flipping a beach cart in college, to eventually earning a spot at TCU and competing in the National Championship — Curtis talks about how doing one more has always been his secret weapon.Now in the oilfield equipment world, Curtis brings that same energy to service, partnerships, and pushing through adversity. Whether you’re in sales, sports, or just trying to grow as a man — this conversation delivers real insights, tough lessons, and practical takeaways.Filmed at Forty Wolves Podcast Studio in Midland, Texas.Chapters:00:00 – Intro & Curtis Raymond’s Background02:00 – Connecting Through Equipment Rentals05:15 – Childhood, Family Values, and Upbringing10:50 – Baseball Dreams vs Football Reality16:10 – Breaking Through in High School Football21:20 – The Injury That Changed Everything26:15 – Ivy League Life & Culture Shock at Cornell31:30 – Setbacks, Mental Growth & Mentorship37:50 – TCU Football, Transfer Portal & National Championship45:30 – What Makes a Great Team: The Max Duggan Effect50:45 – Lessons from Kaz Casati on Mental Toughness55:10 – Business Parallels: Grit, Teamwork & Focus1:00:00 – Jiu-Jitsu, Calm Under Pressure & Life Lessons1:05:00 – Final Thoughts: Competing with Integrity1:07:15 – Outro & Plans for Round Two