Invest Like the Best with Patrick O’Shaughnessy
Business:Investing
My guest today is Robert Smith, the founder, Chairman, and CEO of Vista Equity Partners. An engineer by training, Robert started Vista at the turn of the millennium and built it into one of the world's most successful software-focused investment firms. We discuss the white space left in enterprise software investing, the importance of capital cycles, and what he’s learned building an iconic investing franchise. Please enjoy my discussion with Robert Smith.
For the full show notes, transcript, and links to mentioned content, check out the episode page here.
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Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.
Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.
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Show Notes
[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 p/e 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 what 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 outside of 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
Gaurav Kapadia - Everything Compounds - [Invest Like the Best, EP. 269]
Marko Papic - A Multi-Polar World - [Invest Like the Best, EP. 268]
Garry Tan - Unwrapping the Gift - [Invest Like the Best, EP. 267]
Eric Mandelblatt - Investing in the Industrial Economy - [Invest Like the Best, EP. 266]
Sebastian Kanovich - Powering Emerging Markets Payments - [Founder’s Field Guide, EP. 56]
Frank Slootman - Narrow the Focus, Increase the Quality - [Invest Like the Best, EP. 265]
Tim Flannery - Simplifying Fund Closing - [Founder’s Field Guide, EP. 55]
Joey Levin - Building an Anti-Conglomerate - [Invest Like the Best, EP. 264]
Peter Chernin - Betting on Passion - [Invest Like the Best, EP. 263]
John Pfeffer - Adapt and Evolve - [Invest Like the Best, EP. 262]
Geoffrey Moore - Building Gorilla Businesses - [Invest Like the Best, EP. 261]
Gavin Baker - The Cyclone Under the Surface - [Invest Like the Best, EP. 260]
Sam Englebardt and Richard Kim - Investing in Immersive Worlds - [Invest Like the Best, EP. 259]
Ricky Sandler - Building an Investment Compass - [Invest Like the Best, EP. 258]
Orlando Bravo - The Art of Software Buyouts - [Invest Like the Best, EP. 257]
Nick Saltarelli - One Foot in Front of the Other - [Founder’s Field Guide, EP. 54]
Jenny Johnson - Seven Decades of Investing Expertise - [Invest Like the Best, EP. 256]
Doug Colkitt - The Evolution of Markets - [Invest Like the Best, EP. 255]
Bill Gurley and Philip Rosedale - Back to the Future - [Invest Like the Best, EP. 254]
Francis Davidson - Design-led Hospitality - [Invest Like the Best, EP.253]
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