This week on the show we hear from Justin McKessy, Founder of First Choice Freight on his journey as a logistics entrepreneur. From taking apart electronics as a kid to selling underglow kits for cars on eBay, Justin's curiosity had led him on some unique adventures. His latest adventure is running his own freight brokerage so take a listen to hear how he approaches building something as a Founder.

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This week we hear from Mark Cleveland, Founder and leader of multiple companies spanning trucking, logistics and an elite brand of socks. Listen in as he shares how running multiple businesses simultaneously isn't a distraction but an advantage.

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This week on the show we hear from Rachel Hayden, Founder of Confidential Career Solutions on her journey from being a waitress to working for Fortune 500 companies to launching her own business. Listen in to learn why doubt is part of the journey, but so is owning your own success. 

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What happens when everything you've built crumbles beneath you? For Tyson Lawrence, founder and CEO of Diablo Freight Ventures, bankruptcy wasn't the end—it was just the beginning. During his most difficult moments, Tyson recognized his greatest perceived weakness—empathy—was actually his superpower. He leveraged those learnings to launch his next two ventures and on this week's episode he unpacks all of it to help other entrepreneurs learn from his experience.

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This week on the show we hear from Liz Wayne, founder of Able Transport, as she shares her journey in the freight brokerage industry, discussing the evolution of her company, the challenges of entrepreneurship, and the importance of leadership. She reflects on her experiences in the industry, the need to reinvent the freight broker reputation, and the personal growth she has undergone as a leader. The discussion also touches on the significance of adaptability, hard work, and the values that drive success in business.

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In this candid and insightful episode, host Nate Shutes welcomes Casey Winans, founder of Full Stride WMS, to share his entrepreneurial journey from building a high-growth consulting firm to starting over with a mission-driven focus on helping mid-sized 3PLs and distributors implement smarter warehouse management systems. Casey opens up about the emotional highs and lows of founding, exiting, and rebooting — with lessons on equity, partnership challenges, and staying mission-aligned. It’s a masterclass in resilience, reinvention, and the unglamorous truth behind logistics entrepreneurship. 

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Nate sits down with Josh Klebanoff, Co-Founder and COO of Yolk Transport, to dive into the high-pressure, behind-the-scenes world of Event Logistics. Josh shares his journey from temp worker to entrepreneur, the adrenaline-fueled realities of moving major concerts and events, and what it takes to keep the show on the road — from late-night trucking disasters to delivering stages for world-famous artists. Full of real talk about entrepreneurship, grit, and the magic that happens before the lights come up, this episode is a must-listen for anyone curious about what really keeps the entertainment world moving. 

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Jim Bramlett's 42-year journey through the logistics landscape offers a masterclass in entrepreneurship, leadership, and finding purpose beyond business success. From building businesses to authoring books and now leading peer groups for entrepreneur, Jim has done and seen it all. He's found renewed purpose in helping others avoid the mistakes he made so listen in if you'd like to avoid a few yourself!

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On this episode of The Bootstrapper's Guide to Logistics, Khaki shares his journey from corporate operations to founding ShiftSwap, a labor sharing and planning tool for warehouse operations.

Khaki shares how his approach is built on a commitment to simplicity. "To actually create something simple is extremely complex," he explains. 

With ambitious goals to impact one million hourly workers' lives, Hisham goes deep on what it means to be a bootstrapper – finding elegant (and sometimes scrappy) solutions to overlooked problems.

Whether you manage warehouse operations or dream of building a purpose-driven business, this conversation offers invaluable insights on creating dignity through workplace flexibility.

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What happens when you combine Philadelphia grit, Chicago hustle, and cutting-edge AI technology? You get Chris Agnew's journey to founding Freight IQ.

Growing up in a blue-collar Philadelphia neighborhood where "everything was a competition" and working in his mother's restaurant (where he nearly got fired) Chris developed resilience and people skills. After 8 years at Coyote Logistics he spent the next six at Molo. This long-term approach to understanding the business gave him unique insights into complete market cycles and the operational challenges facing brokerages during both bull and bear markets. 

The entrepreneurial spark ignited when Chris recognized how advanced AI and machine learning technology could transform these operational bottlenecks. Freight IQ was born from his vision to create software solutions that enable logistics companies to operate more efficiently while preserving what matters most - the human relationships at the heart of the industry.

What makes Chris's approach distinctive is his unwavering belief that despite technological advancement, logistics remains fundamentally a "people game." His philosophy combines domain expertise with innovative technology to address not just surface-level challenges but the complex exception management scenarios that often derail operations.

Ready to see how combining old-school values with cutting-edge technology is reshaping the logistics landscape? Listen now and discover why sometimes the most revolutionary ideas come from those willing to do the unglamorous work of fully understanding an industry before trying to transform it.

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