Andrew sits down with Jin Stedge, CEO and cofounder of TrueNorth. Jin grew up in a family of owner-operators, including her dad, uncles, and grandparents, but didn’t see herself in the family business. Instead, she headed to MIT, earned an aeronautical engineering degree, and built her career in consulting, HR tech, and — autonomous trucking. But Jin knew truckers had more immediate needs and that's how the industry pulled her in. 

In this episode, Jin also talks about:

• The evolution of TrueNorth, which evolved from being a carrier to an AI load board with a virtual dispatcher named Loadie, and what she hopes the business looks like five years from now.
• The biggest challenges of building a load board, the necessary features and qualities of an AI load board, how TrueNorth approaches fraud, and what new solutions could improve load boards.
• How technology should enhance rather than replace the human connection to make freight relationships more successful.
• Raising a $50M Series B with Sam Altman as an early backer, how she made the decisions to use the money and what she may have done differently, and best practices for staying in touch with investors, including her “Weekly Reflection.”
• Running the business through maternity leave and early motherhood.