DDU Collapse, Hard Pivots, Real Leadership: The NOW Courier Story

Season 4 of the Last2First Podcast kicks off with Ryan Schwalbach, President at NOW Courier. Ryan’s journey as a second-generation owner is full of highs, lows, and tough decisions—including firing his largest customer just years after acquiring the company from his parents. In this conversation, Ryan shares raw insights on leadership, resilience, and navigating a courier business through change, growth, and eventual sale. Topics We Cover in This Episode: ✅Second-generation ownership in the final mile industry ✅Transitioning a family business to the next generation ✅Scaling operations with independent contractor drivers ✅Tough leadership calls and letting go of major accounts ✅Customer relationships, pricing power, and profitability ✅Navigating market shifts and industry pressures ✅The emotional side of acquisitions and ownership ✅Building resilience as a leader in uncertain times ✅Selling a courier business and what drives the decision ✅The future of the final mile: data, drivers, and leadership 🔥 Season 4 also introduces a brand-new segment: 🚛 Driving the Mile — ride-along with drivers for a ground-level perspective 👉 Don’t miss a single episode! Subscribe: YouTube: https://www.youtube.com/@Last2FirstPodcast Spotify: https://open.spotify.com/show/3gDS58wo6IWeLl48LHukdP?si=gmhv7Lh8QvyY5xxFS9ZpPA Apple Podcasts: https://podcasts.apple.com/hn/podcast/last2first-podcast/id1778491941 👉 Connect with our guest: Follow Ryan Schwalbach on LinkedIn: https://www.linkedin.com/in/ryanschwalbach/ Follow NOW Courier: https://www.nowcourier.com/ #Last2FirstPodcast #FinalMile #Season4 #NOWCourier