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.
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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
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You can also find this group chat in audio format as an episode on our Everything Marketplaces podcast on Apple Podcasts and Spotify. You can also connect with marketplace founders & leaders from our group chats in the Everything Marketplaces community.