Navigating Startup Challenges: From MVP to Market

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!