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 Bitfr...
Jun 23, 2025•42 min•Season 3Ep. 8
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 dri...
Jun 09, 2025•30 min
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 mast...
May 26, 2025•53 min•Season 3Ep. 6
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...
May 12, 2025•49 min•Season 3Ep. 5
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 ....
Apr 28, 2025•46 min•Season 3Ep. 4
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) so...
Apr 21, 2025•43 min•Season 3Ep. 3
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 i...
Apr 07, 2025•44 min•Season 3Ep. 2
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 job ...
Apr 01, 2025•37 min•Season 3Ep. 1
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 .
Dec 05, 2024•19 min•Season 2Ep. 53
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 .
Nov 21, 2024•25 min•Season 2Ep. 52
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 .
Oct 31, 2024•35 min•Season 2Ep. 51
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 .
Oct 17, 2024•28 min•Season 2Ep. 50
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 ....
Oct 10, 2024•21 min•Season 2Ep. 49
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 .
Oct 10, 2024•41 min•Season 2Ep. 48
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 .
Oct 03, 2024•42 min•Season 2Ep. 47
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 .
Sep 19, 2024•46 min•Season 2Ep. 46
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 .
Sep 12, 2024•39 min•Season 2Ep. 45
This week we hear the backstory of HighlanderTek with Founder Dyrc McCleod. From his days as a ski bum to working in finance to making the leap into logistics entrepreneurship, Dyrc has seen a thing or two. Listen in as he shares his personal story and why getting the last few feet of the final mile is essential. Brought to you by Rapido and Bitfreighter .
Sep 05, 2024•37 min•Season 2Ep. 44
This week on the show we hear from Benjamin Kowalski, the Founder of Freight 360 and President of Forza Logistics Group. We go deep on peak mental performance, understanding human psychology and the value of having to struggle for success. Brought to you by Rapido and Bitfreighter .
Aug 22, 2024•43 min•Season 2Ep. 43
This week on the show we uncover the journey of Joe DiLeo, Founder & CEO of Chariot Logistics. Listen in as he shares how he moved back in with family and worked for 3 straight months before he landed his first customer shipment. Joe shares how bootstrapping has kept them focused on organic growth and retaining key talent by playing the long game. Brought to you by Rapido and Bitfreighter ....
Aug 08, 2024•36 min•Season 2Ep. 42
This week we hear from Nate Johnson, Founder of GLCS on his journey from trucking to technology and the shift to entrepreneurship. Listen in as he describes his mindset around failure and mistakes and how a simple change in perspective can set you up for long-term success. Brought to you by Rapido and Bitfreighter .
Jul 25, 2024•47 min•Season 2Ep. 41
This week we hear the backstory of how Tim Judge built a supply chain consulting firm powerhouse with just $2,500 to start. Listen in as he describes how he balances leadership, values and relationships while staying true to his humble bootstrapped beginnings. Brought to you by Rapido and Bitfreighter .
Jul 18, 2024•39 min•Season 2Ep. 40
This week on the show we hear from Curtis Garrett, Founder of Rate Hero and Understand LTL. Listen in as he shares how the best bet he ever made was on himself and that when it's time to take the leap into entrepreneurship, you'll just know. Levity AI Streamline your freight email operations Rapido Solutions Group How freight companies find freight talent. Disclaimer: This post contains affiliate links. If you make a purchase, I may receive a commission at no extra cost to you. Brought to you by...
Jul 11, 2024•39 min•Season 2Ep. 39
This week we hear from Jennie Malafarina, Founder of Virago Marketing. Listen in to her backstory of how very humble beginnings and personal adversity prepared her for the challenges of supply chain entrepreneurship. Brought to you by Rapido and Bitfreighter .
Jun 27, 2024•40 min•Season 2Ep. 38
This week on The Bootstrapper's Guide to Logistics we hear from Dan Lindsey, Founder of Linkage Logistics and The Broker Carrier Summit. Listen in on how history has proven time and time again that in person relationships will always be necessary. Hear his approach to positive accountability and how capitalizing on failure can make all the difference. Brought to you by Rapido and Bitfreighter ....
Jun 20, 2024•37 min•Season 2Ep. 37
This week on The Bootstrapper's Guide to Logistics we hear from Spencer Tenney of The Tenney Group . Spencer opens up about being a second-generation business owner, what it takes to be successful in the logistics M&A space and how a chicken sandwich led to an unexpected hit in the music industry. Rapido Solutions Group How freight companies find freight talent. Levity AI Streamline your freight email operations Bitfreighter Scale your shipper integrations 10x with unlimited messaging. No Tr...
Jun 13, 2024•48 min•Season 2Ep. 36
This week on the Bootstrapper's Guide to Logistics we hear from Thilo Huellmann, co-Founder of Levity . Thilo shares how lifelong curiosity and a thirst for new knowledge and experiences have shaped his approach to life and business. Listen in for insights on how AI is changing logistics communication for the better. Brought to you by Rapido and Bitfreighter ....
Jun 06, 2024•48 min•Season 2Ep. 35
This week we hear from Jacky Zhao and Anthony Chen on the backstory behind FreightStack and how a near-death moment inspired them to take the leap. Listen in on what it's like working with your best friend, how to blend generalists and specialists and avoiding shiny object syndrome. Brought to you by Rapido and Bitfreighter .
May 30, 2024•36 min•Season 2Ep. 34
Welcome back to another episode of The Bootstrapper’s Guide to Logistics. Today's guest is John Sanford, the founder and CEO of CNT Logistics. John discusses the early days of the company, his sales philosophy and gives advice to entrepreneurs. Brought to you by Rapido and Bitfreighter .
May 23, 2024•35 min•Season 2Ep. 33
Welcome back to another episode of The Bootstrapper’s Guide to Logistics. Today's guest is Sarah Barnes-Humphrey, Founder and Host of Let's Talk Supply Chain. From her start working for her father's company to launching her own podcast, “Let’s Talk Supply Chain,” Sarah discusses the challenges of entrepreneurship and the importance of community support. Brought to you by Rapido and Bitfreighter ....
May 09, 2024•37 min•Season 2Ep. 32
