This is Rick. Today's teacher is Rich Wells, managing director of Insight Partners, which celebrates its 30th anniversary this month. I've known Rich for 20 years since our time as section mates in business school, where he was consistently recognized as the smartest person in the room. Rich is universally regarded as one of the preeminent private market software investors of the last 20 years, helping drive Insight's success through agility and excellence. While achieving the highest heights in his career, Rich has also faced profound personal challenges, including the tragic loss of his wife Rachael.

This vulnerable conversation offers critical wisdom about resilience and moving forward through life's darkest moments. No matter what life throws at you remember that you've got to find a way to keep going. Please enjoy class with my dear friend and software savant, Rich Wells.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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Joys of Compounding is a property of Pine Grove Studios in collaboration with Colossus, LLC. For more episodes of Joys of Compounding, visit joincolossus.com/episodes.

Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com).

Show Notes

(00:00:00) Learn about EightSleep

(00:02:57) Meet Today's Teacher: Rich Wells

(00:10:04) Early Career Challenges and Lessons

(00:14:59) Joining Insight Partners

(00:17:20) Reflecting on TCV and Moving to Business School

(00:19:11) Experience at Business School and Joining Insight

(00:26:05) Insight's Growth and Strategy

(00:30:38) Evolution of Software and Investment Strategies

(00:34:48) Impact of SaaS and Cloud on Software Development

(00:36:41) Investment Philosophy and Market Insights

(00:39:01) Empowerment and Team Dynamics

(00:43:05) Majority Stakes and Mindset Shifts

(00:45:14) Evolution from Value to Growth Investing

(00:47:49) Shopify: A Generational Company

(00:51:39) Expanding TAM: The Role of Payments

(00:55:02) Personal Struggles and Triumphs

(00:59:25) Rachel's Legacy and Life Lessons

(01:10:06) Future of Software

Hour 4: Toronto Police score generous deal, Marilyn Denis talks entertainment, and Doug Ford denies Therme Spa duped Ontario.