The Time Freedom Podcast

Tim Jenkins and Darran Littlefield Built Time Freedom Before It Had a Name

Episode Summary

Today on the podcast, Brian and Kirby welcome Tim Jenkins and Darran Littlefield. Tim is a co-founder of Point B, a national management consulting firm. He now splits his time between Leavenworth, Washington and Park City, Utah, where he runs Colchuck, a purposeful private investment company. Darran co-founded Point B alongside Tim. He recently relocated to Dallas to be closer to family and continues to work on projects with Tim. This is one of those rare episodes where Brian gets to thank two people who shaped who he is. In this episode... Tim and Darran didn't set out to build a consulting empire. They set out to coach their kids' sports teams, be home for dinner, and not spend their lives in airport lounges. In 1995, they walked away from the grind at Accenture, started Point B with $200 (technically $300, but Tim never paid his share), and built what became one of the most admired consulting cultures in the country. Brian worked for Point B for six formative years of his career. He gets to go back to the source to inquire how the partnership actually worked, what broke down and what held, how they built time freedom in from day one before anyone called it that, and what both men believe about work, retirement, and what a life well-spent looks like.

Episode Notes

Top 5 Takeaways:

1. Time freedom doesn't have to come at the end. Tim and Darran built it into Point B from the very beginning, designing work around their lives rather than the other way around.
2. Company culture is like a bank. If everyone makes deposits, it scales infinitely. If people only make withdrawals, it quietly collapses. The CEO isn't the keeper of culture, because everyone is.
3. Partnerships survive when you commit to them like a marriage. Tim, Darran, and their third co-founder Jim Hodge made a five-year no-exit pact and stayed unified through it all.
4. You have time capital and financial capital, and the ratio shifts throughout your life. Managing both intentionally is the real game.
5. Retirement is a myth. Work isn't the opposite of freedom. When you get the work right, it's what sustains you. The goal isn't to stop, but to find work worth doing until you can't anymore.

Chapters: 

• 00:00 Introduction and Everyday Leadership
• 07:35 The Origins and Vision Behind Point B
• 12:15 Building an Intentional Company Culture
• 16:23 Rethinking Consulting and Flexible Work
• 22:31 Time Freedom vs. Financial Freedom
• 30:07 The Power of Partnerships and Collaboration
• 38:13 Culture, Leadership, and Employee Well-Being
• 40:38 Redefining Retirement and Work-Life Balance
• 45:17 Career Transitions, Contribution, and Community
• 54:22 Introduction to Time Freedom Book Promotion

TIM JENKINS is the co-founder and former co-CEO of Point B, Inc., a national management consulting firm he built from three partners in 1995 to a 100% employee-owned firm with over a thousand professionals. In 2010 he was named Ernst and Young's Entrepreneur of the Year in Services for the Pacific Northwest. Today he is President of Colchuck, a purposeful private investment company based in Leavenworth, Washington, where he focuses on backing founders who are doing well and doing good at the same time. You can connect with Tim on LinkedIn.

DARRAN LITTLEFIELD is the co-founder and former co-CEO of Point B, Inc., where he helped build one of the most admired people-first cultures in the consulting industry. He served alongside Tim for nearly two decades before the founders transitioned full ownership to their employees through an ESOP. Darran now lives in Dallas, Texas, where he relocated to be closer to family, and continues to collaborate with Tim on new work. You can connect with Darran on LinkedIn.