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Robert Smith: AI, Enterprise Software and the Future of Investing
Join Creative Planning President and CEO Peter Mallouk and Vista Equity Partners Founder, Chairman and CEO Robert Smith for a conversation on AI in enterprise software and what it means for investors. They explore how AI agents are reshaping SaaS business models, why mission-critical systems must be highly accurate and how enterprise AI is shifting value from seat-based pricing to measurable outcomes. They also discuss durable value creation, market volatility and how long-term investors can stay focused when headlines move faster than fundamentals.
(00:00) Introduction
(01:24) How early exposure to tech shaped Robert’s edge
(02:44) Lessons from Wall Street that still apply today
(03:50) Why enterprise software can be a durable investment
(04:29) “No finish line” — the mindset behind continuous improvement
(06:21) Davos takeaways that matter for markets
(07:03) Using AI without giving away enterprise value
(09:06) Enterprise software, explained in plain English (an insurance example)
(10:51) When “mostly right” can cost you money
(12:16) What investors are getting wrong about AI and subscription software
(14:00) From seats to agents: what this shift means for growth and pricing
(16:34) Why some software is so hard to replace
(19:03) The skills that still pay off as AI reshapes services
(22:40) A better way to trust your gut: test, learn, repeat
(24:56) Building teams that keep up with constant change
(27:00) Discipline and excellence — the advantage that compounds
(28:53) Where innovation is happening now (and how to keep up)
(31:43) The messy middle: what change looks like before it works
(36:25) Why no sector stays safe forever — and what to do instead
(39:16) The Morehouse moment — and a mindset you can use now
RESOURCES
Follow Peter on his social media accounts: X | LinkedIn | Instagram | Facebook
Follow Creative Planning’s social media accounts: X | LinkedIn | Instagram | Facebook
Browse through all our episodes here.
Like the Icons and Ideas podcast? Check out Peter’s other podcasts!
Signal or Noise
Down the Middle
View all episodes
By Peter Mallouk
4.9
1919 ratings
Join Creative Planning President and CEO Peter Mallouk and Vista Equity Partners Founder, Chairman and CEO Robert Smith for a conversation on AI in enterprise software and what it means for investors. They explore how AI agents are reshaping SaaS business models, why mission-critical systems must be highly accurate and how enterprise AI is shifting value from seat-based pricing to measurable outcomes. They also discuss durable value creation, market volatility and how long-term investors can stay focused when headlines move faster than fundamentals.
(00:00) Introduction
(01:24) How early exposure to tech shaped Robert’s edge
(02:44) Lessons from Wall Street that still apply today
(03:50) Why enterprise software can be a durable investment
(04:29) “No finish line” — the mindset behind continuous improvement
(06:21) Davos takeaways that matter for markets
(07:03) Using AI without giving away enterprise value
(09:06) Enterprise software, explained in plain English (an insurance example)
(10:51) When “mostly right” can cost you money
(12:16) What investors are getting wrong about AI and subscription software
(14:00) From seats to agents: what this shift means for growth and pricing
(16:34) Why some software is so hard to replace
(19:03) The skills that still pay off as AI reshapes services
(22:40) A better way to trust your gut: test, learn, repeat
(24:56) Building teams that keep up with constant change
(27:00) Discipline and excellence — the advantage that compounds
(28:53) Where innovation is happening now (and how to keep up)
(31:43) The messy middle: what change looks like before it works
(36:25) Why no sector stays safe forever — and what to do instead
(39:16) The Morehouse moment — and a mindset you can use now
RESOURCES
Follow Peter on his social media accounts: X | LinkedIn | Instagram | Facebook
Follow Creative Planning’s social media accounts: X | LinkedIn | Instagram | Facebook
Browse through all our episodes here.
Like the Icons and Ideas podcast? Check out Peter’s other podcasts!
Signal or Noise
Down the Middle
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