Jack of Oil Trades

The Entrepreneurial Mindset of Kristen Chandler

n this episode of Jack of Oil Trades, Stephen sits down with serial entrepreneur Kristen Chandler, whose career spans wellness clinics, Subway franchising, occupational drug testing, and supporting oil and gas companies nationwide.Kristen’s story is a masterclass in figuring it out as you go. From opening the first Subway in Greenwood after realizing the community had literally nowhere to eat, to running drug testing services across the U.S., to managing wellness spas inspired by her sister’s cancer journey — Kristen has built every business by solving real problems as they appeared.This is an episode full of entrepreneurial wisdom, wild stories, and genuine inspiration for anyone building something from nothing.

Control, Faith, and the Business of Loyalty

In this new episode of Jack of Oil Trades, host Stephen Wilson sits down again with Dakotah Klein of LOC for a candid and wide-ranging conversation on business, faith, and the mindset it takes to thrive in uncertain times.Dakotah opens up about learning to surrender control — in life, leadership, and the oilfield — and how blending faith with business transformed his outlook. He shares real-world lessons from managing downturns, balancing humility with confidence, and investing in relationships that last longer than any company name.From oil prices and loyalty to pride, mentorship, and Midland life, this is a grounded, hard-won conversation about staying centered when everything else shifts.Chapters00:00 – Cold Open00:31 – Introduction01:12 – Controlling Costs in a Downturn03:59 – Faith in Business07:34 – Perspective on Influence09:01 – The Illusion of Control13:45 – Humility and Mentorship17:20 – People Over Companies20:12 – Character in Business23:54 – Wisdom and Acceptance27:39 – Hearing vs. Listening31:26 – The Real Market36:27 – Small Bank Relationships40:32 – Life Updates44:57 – New Ventures47:05 – Closing Reflections

Amanda Wilson on Books, Business & Community in West Texas

In this episode of the Jack of Oil Trades Podcast, host Stephen Wilson sits down with a very special guest—his wife, Amanda Wilson, co-owner of Paper & Vine in Midland, Texas.Amanda shares the journey of opening a bookstore and bar with her mom and sister, from an idea sparked on TikTok to a reality in just 45 days. She opens up about the challenges of choosing the right books for her shelves, managing a team, and balancing life as a nurse practitioner, mom of four, and business owner.She also talks about why building community matters so much to her, the joy of hosting events like fantasy nights and trivia, and how Paper & Vine is more than a bookstore—it’s a space for connection, creativity, and belonging.Chapters00:00 – Meet Amanda Wilson, Co-Owner of Paper & Vine02:00 – From Meet Cute to Paper & Vine: The Naming Journey04:30 – Inspiration Behind Starting a Bookstore07:45 – Launching a Business in 45 Days10:15 – Learning the Publishing & Ordering Process12:20 – Family Roles in Running the Store15:20 – Building Community Through Books & Events18:00 – The Challenges of Bookstore Ownership21:30 – Leadership & Management Styles23:45 – Creating a Happy Space for Women in Midland26:00 – Amanda’s Favorite Genres (Thrillers & Dark Romance!)29:00 – Balancing Motherhood, Work & Passion32:00 – Looking Ahead: Events, Community & Expansion34:30 – Closing Thoughts with Amanda & Stephen

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

From West Texas Oilfields to Wall Street Fallout

Step into the world of rural finance, oil fields, and unforgettable stories with Stephen Wilson and his guest, Michael Eisenwine — a fifth-generation banker with deep West Texas roots. In this episode of Jack of Oil Trades, Michael takes us through a career shaped by the highs and lows of community banking, the chaos of the 2008 financial crisis, and the colorful history of cattle rustling and oil booms.From regulatory battles and economic shifts to eyebrow-raising tales of conspiracy and small-town intrigue, this conversation unpacks the complexities of modern banking through a lens only someone with Michael’s legacy could provide.Whether you're in the industry or just love a good story, this episode brings sharp insight and Texas-sized personality to topics often hidden behind boardroom doors.👉 Don’t forget to like, comment, and subscribe for more stories at the intersection of oil, money, and the people who keep both moving.