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He grew to millions in ARR in 18 months—by fighting with his co-founders on purpose. | Ross McNairn, Co-Founder of Wordsmith AI.
Manage episode 500206599 series 3298391
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
Chapters
1. Intro (00:00:00)
2. From Lawyer to CTO (00:01:31)
3. Starting Wordsmith AI (00:03:45)
4. Testing Co-Founder Relationships (00:06:41)
5. Building the MVP (00:14:42)
6. First Product Iterations (00:20:44)
7. Finding Product Market Fit Through Slack (00:26:39)
8. Go-to-Market Using Webinars and Influencers (00:37:42)
9. Balancing Startup Life with a 10-Month-Old Baby (00:47:00)
216 episodes
Manage episode 500206599 series 3298391
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
Chapters
1. Intro (00:00:00)
2. From Lawyer to CTO (00:01:31)
3. Starting Wordsmith AI (00:03:45)
4. Testing Co-Founder Relationships (00:06:41)
5. Building the MVP (00:14:42)
6. First Product Iterations (00:20:44)
7. Finding Product Market Fit Through Slack (00:26:39)
8. Go-to-Market Using Webinars and Influencers (00:37:42)
9. Balancing Startup Life with a 10-Month-Old Baby (00:47:00)
216 episodes
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