Helping Drivers Think Like Business Owners with Annique Lesage | Ep 56

In this episode of Miles and Mentors: A Trucking Podcast, Annique Lesage, founder of Small World Ventures, shares her unconventional journey into freight and the hard-earned wisdom that came with it. With a background in biology and no initial intention of entering logistics, Annique started on the shipper side handling customs and LTL shipments before transitioning into sales. When she moved into brokerage, she quickly realized that most large firms don’t actually teach the skills needed to succeed. Left to figure it out on her own, Annique faced early losses and hard lessons until a group of experienced women took notice and stepped in to mentor her. That mentorship, while direct and unsentimental, gave her the tools to truly understand the business and build something of her own.

Throughout the episode, Annique speaks with clarity about what it really takes to grow in this industry. She stresses that drivers looking to become owners must shift their mindset from simply doing a job to running a company. Professionalism, preparation, and understanding how to navigate both the business and relational sides of freight are key themes she returns to often. She explains why reputation matters at every level and how one poorly planned interaction can damage not only your own credibility but that of your partners as well. Annique also unpacks common misconceptions about brokers and explains how resentment between carriers and brokers often stems from misinformation rather than reality.

Her advice for new entrants is refreshingly honest. Know your numbers, pick a niche, protect your relationships, and don’t assume mentorship always looks like friendship. She also urges drivers to develop both entry and exit strategies, warning against the all-too-common trap of having no plan for life after trucking. This episode is packed with operational insight, real-world strategies, and the kind of mentorship-driven clarity that many in the industry are missing. Whether you’re launching a new operation or trying to course-correct an existing one, Annique’s story and perspective offer a valuable roadmap.