He Sold His First Company at 28. Then Came Freight

Tim Higham, CEO & Founder of AscendTMS, shares his journey from building a fintech company, to launching a freight brokerage, to creating a cloud-based TMS platform, and more. This week's episode is sponsored by Epay Manager, Highway, Resolve Logistics and Bitfreighter. Interested in sponsoring our podcast? Send us an email at pbj@freightcaviar.com. CHAPTERS: 0:00 Intro 1:12 Meet Tim Higham 2:02 From Fintech Exit to Freight 3:10 Why Tim Built His Own TMS 5:40 The First AscendTMS Customer 9:15 How Tim Evaluates New Freight Tech 12:18 Hundreds of AI Experiments Later 14:27 The Economics of AI 18:38 Practical AI: Run Your TMS by Voice 23:16 If Tim Started a Freight Tech Company Today 25:19 Freight’s “Members-Only” Future 29:02 The SCOTUS Ruling and Carrier Vetting 34:18 Will AI Eliminate Freight Jobs? 38:22 A $40M Brokerage With Half the Staff 41:54 What Happens to the Jobs AI Replaces? 47:54 Where Tim Would Invest $1M 56:11 Autonomous Trucking: Not in My Lifetime 58:58 “Entrepreneurship Is a Disease” 1:05:07 Can Your Business Run Without You? 1:06:57 Every Entrepreneur Is Driven by Fear 1:08:07 Curiosity, Burnout, and Shiny Objects 1:12:16 Tim Consults Tom on His Sauna Podcast 1:23:01 Building a $1M Podcast Business 1:26:29 What Comes After Podcasts and Conferences?