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 faster
- The accidental fundraising playbook that made VCs go crazy
- How having a baby forces you to be 10x more productive as a founder
Keywords:
Wordsmith AI, Ross McNairn, AI legal tech, product market fit, co-founder selection, Series A, Index Ventures, Slack integration, startup pivots, legal AI
00:00:00 - Intro
00:01:31 - From Lawyer to CTO
00:03:45 - Starting Wordsmith AI
00:06:41 - Testing Co-Founder Relationships
00:14:42 - Building the MVP
00:20:44 - First Product Iterations
00:26:39 - Finding Product Market Fit Through Slack
00:37:42 - Go-to-Market Using Webinars and Influencers
00:47:00 - Balancing Startup Life with a 10-Month-Old Baby
Send me a message to let me know what you think!
