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. Brought to you by Rapido and Bitfreighter.

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. Brought to you by Rapido and Bitfreighter.

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. Brought to you by Rapido and Bitfreighter.

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. Brought to you by Rapido and...

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 ...

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 m...

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 lig...

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! Brought to you by Rapido and Bitfreighter.

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 ...

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 insigh...

In an industry often dominated by venture-backed startups and high-risk entrepreneurship, Blake Collins - Founder of Armada - offers an alternative perspective on building a business the thoughtful way. As the co-founder and managing director of Armada, a specialized recruiting firm focused on supply chain talent, Blake shares his journey from CH Robinson executive to entrepreneur without sacrificing financial stability or family priorities. Rather than following the conventional "quit your ...

This week on the show we hear an update from Andy Shiels, Founder of SiLo two years after we shared his original episode. Listen in as he shares how running a 'boring' business can lead to ongoing success and how he would encourage others to focus on the fundamentals. Brought to you by Rapido and Bitfreighter.

This week we hear an update from Brad Forester who first shared his story with us in 2022. In this update he shares what he has learned as a leader and entrepreneur over the last 2 years including his most difficult challenge yet - leaving the country (and his business) for over a month. Brought to you by Rapido and Bitfreighter.

This week we hear an update from Charlie Saffro on the time warp that the last 2 years have been in the supply chain talent industry. Charlie opens up about one of the biggest challenges she has faced yet...burnout. Listen in as she shares what she's learned about business and herself. Brought to you by Rapido and Bitfreighter.

Two and half years have passed since Kara Smith Brown first shared her Founder journey. This week we get to hear what she has been up to since then and how she has grown as an entrepreneur (and as an author!), including her advice for first-time supply chain founders. Brought to you by Rapido and Bitfreighter.

This week on The Bootstrapper's Guide to Logistics we hear from Michael Malakhov, Founder of Carpool Logistics on what he has learned about his business and himself since airing his original story in 2022. Listen in as he discusses the importance of having the right team and how constantly reaching for new milestones is essential to driving progress. Brought to you by Rapido and Bitfreighter.

This week on The Bootstrapper's Guide to Logistics we hear Tristan Bordallo's backstory on how he started iamFr8 and Freightopia; two companies making it happen in transportation. Listen in to his personal journey of why he does it and how he shows up with good vibes wherever he goes. Brought to you by Rapido and Bitfreighter.

This week on The Bootstrapper's Guide to Logistics we explore the background of Manifest: The Future of Supply chain with Courtney Muller who was there at the beginning. Listen in as we discuss community-building and supply chain entrepreneurship for the fastest-growing industry event. Brought to you by Rapido and Bitfreighter.

This week on the show we hear from Tate Mason, Founder & CEO of Pallet. Tate shares his approach to why building with Legos or software have a lot in common and how not following the instructions can lead to innovation. Listen in as he shares the origin story of his company while offering a masterclass on technology strategy. Brought to you by Rapido and Bitfreighter.

This week we hear the backstory of Ship Smarter LLC with Founder, Cody Branham. From discovering the joys of solving puzzles and building things as a child to overcoming ADHD and buckling down, Cody shares how his personal experiences have shaped him into an entrepreneur that doesn't follow anyone else's mold. Brought to you by Rapido and Bitfreighter.