Learnings From Starting & Scaling Convoy As A B2B Marketplace With Dan Lewis | EM Group Chat #194

Recording of the Everything Marketplaces Group Chat #194 (7/1) with Dan Lewis. Dan previously started Convoy, which scaled to become one of the largest digital freight marketplaces. Convoy was often referred to as the "Uber for trucking" and raised over $1B+ in capital from investors like Y Combinator, Greylock, and Jeff Bezos. It was eventually acquired by Flexport in a technology acquisition and Dan has since joined Microsoft to lead their Copilot and AI Business initiatives. 0:05 Intro 1:11 Dan's background 2:15 The founding story for Convoy 4:14 How Convoy solved the cold start problem 8:52 How Convoy initially constrained markets 11:12 How Convoy evolved & scaled 15:47 Managing risk 18:49 Team building & hiring tips 22:53 Key fundraising learnings after raising $1B+ in capital 24:48 How Dan would leverage AI if starting Convoy today 27:10 Tips for selling AI solutions in legacy markets 28:33 Tips for early-stage marketplace founders 29:51 Group Q&A on how Convoy vetted supply 32:29 Group Q&A on the new market launch & expansion playbook for Convoy 35:00 Group Q&A on team building & hiring with AI 37:26 Group Q&A on evaluating risk as a founder 40:59 Parting marketplace advice Dan on Twitter/X: https://www.x.com/daniellewis Dan on LinkedIn: https://www.linkedin.com/in/danlewis4545 Mike (Yoroomie) on Twitter/X: ⁠⁠⁠⁠⁠⁠https://www.x.com/yoroomie⁠⁠⁠⁠⁠⁠ Mike (Yoroomie) on LinkedIn: ⁠⁠⁠⁠⁠⁠https://www.linkedin.com/in/yoroomie⁠⁠⁠⁠⁠⁠ Join other marketplace founders & all of our group chats: https://www.everythingmarketplaces.com