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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.

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Manage episode 500206599 series 3298391
Content provided by Mistral.vc. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Mistral.vc or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://podcastplayer.com/legal.

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!

  continue reading

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

Artwork
iconShare
 
Manage episode 500206599 series 3298391
Content provided by Mistral.vc. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Mistral.vc or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://podcastplayer.com/legal.

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!

  continue reading

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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