Ross went from lawyer to self-taught engineer to CTO at a 1,600-person unicorn—then quit to build Wordsmith AI. In 18 months, he's raised $30M and grown to mid-single-digit millions in ARR by doing everything differently. He tested co-founders by starting fights. Built in Slack for 10 months before adding a web interface. Kept his team at 8 people while competitors hired dozens. This episode breaks down his exact playbook: how to test co-founders before committing, why attacking someone's core job kills your sales cycle, and how he accidentally created the hottest seed round by ghosting every VC. Plus the reality of building a rocket ship with a newborn at home.Why You Should Listen:Why starting fights with co-founders can be a great way to test conflict.Why keeping your team at 8 people until PMF lets you move fasterThe accidental fundraising playbook that made VCs go crazyHow having a baby forces you to be 10x more productive as a founderKeywords:Wordsmith AI, Ross McNairn, AI legal tech, product market fit, co-founder selection, Series A, Index Ventures, Slack integration, startup pivots, legal AI00:00:00 - Intro00:01:31 - From Lawyer to CTO00:03:45 - Starting Wordsmith AI00:06:41 - Testing Co-Founder Relationships00:14:42 - Building the MVP00:20:44 - First Product Iterations00:26:39 - Finding Product Market Fit Through Slack00:37:42 - Go-to-Market Using Webinars and Influencers00:47:00 - Balancing Startup Life with a 10-Month-Old BabySend me a message to let me know what you think!

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