Investing in Enterprise Software

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[00:02:34] - [First question] - What the enterprise software market looks and feels like to him

[00:05:52] - Whether or not software is becoming a saturated market and what will drive demand over the coming decades

[00:09:42] - Bringing an engineering mindset to enterprise software investing and culture

[00:12:36] - A single change he made to a business that stands out most in memory

[00:14:33] - Qualities that are most critical in defining a good enterprise software company

[00:18:07] - How the profile of companies he’s bought has changed over the years

[00:20:33] - Categories of software he tends to gravitate towards 

[00:23:56] - Evolving his model for considering what multiple to pay for a business and thinking about price revenue growth multiples 

[00:27:17] - Lessons learned about customer churn over his twenty two year career

[00:29:44] - Capital cycles and how much they truly impact the software world 

[00:31:53] - What elements of building Vista have most appealed to him over the years  

[00:34:31] - Changing their investment strategy as the world continues to change

[00:38:06] - The war for talent and his senior team would debate most 

[00:40:01] - Biggest mistakes Vista has made and what they taught him

[00:41:09] - What has him most insecure or paranoid about the platform he’s built

[00:43:10] - The advice he’d give on having good relationships with LPs

[00:44:57] - The largest risk he or Vista has ever intentionally taken 

[00:46:15] - What he’s learned about having a winning negotiations and sales approach

[00:49:27] - Who he’d give all of his capital to that has nothing to do with Vista

[00:50:06] - How he arrived at the themes he tends to be philanthropic towards

[00:53:08] - The work he does in the foster world

[00:54:49] - The kindest thing anyone has ever done for him