
39 segments available
Gokul Rajaram joins Patrick to discuss the seismic shift in product building driven by AI. As a legendary operator (Google, Facebook, Square, DoorDash) and prolific investor, Gokul breaks down how tools like Claude are merging design and engineering roles and why human "judgment" is the only future-proof skill. They explore the durability of software companies in an agentic world, the mechanics of building massive ad businesses, and lessons learned from working directly with leaders like Larry Page, Mark Zuckerberg, and Jack Dorsey. Finally, Gokul shares a framework for career growth and hiring "builders" in the AI era. Timestamps: 0:00 Intro 0:35 The Changing Nature of Product Development 4:09 The Merger of Product and Design 4:54 Managing Non-Deterministic Software 9:06 Judgment: The Future-Proof Human Skill 10:41 Building Durable AI Applications 16:43 The Risk to Legacy Software Companies 21:20 Sources of Stickiness in the Age of AI 23:43 Leadership Lessons from Google 27:41 Learning from Mark Zuckerberg 31:16 Jack Dorsey and the Philosophy of Great Design 35:48 The Product Manager as Editor 40:44 Three Pillars of a Successful Ads Business 49:03 Selecting North Star and Check Metrics 56:04 Hiring Functional Experts for the AI Era 1:00:06 Advice for Managing a Career 1:01:33 Evaluating Founder Authenticity 1:05:20 Best Practices for Board Management 1:11:15 The Kindest Thing #investing #business #productmanagement #ai #tech #startups #software #leadership #career #siliconvalley Presented by Ramp: https://ramp.com/invest Sponsored by WorkOS, Rogo, Vanta and Ridgeline: https://workos.com/ https://rogo.ai/invest https://www.vanta.com/invest https://www.ridgelineapps.com/ ****** Patrick O'Shaughnessy is the CEO of Positive Sum. All opinions expressed by Patrick and podcast guests are solely their own and do not reflect the opinion of Positive Sum. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of Positive Sum may maintain positions in the securities discussed in this podcast. To learn more, visit psum.vc
A discussion on how AI is transforming the roles and processes in product development.
"The one thing I think that's going to be truly future proof is judgment. Why? Because you have the big challenge of AI slop. Every product leader I've talked to is extremely worried that because you h..."
An exploration of how product management roles and collaboration methods are evolving with AI capabilities.
"And what that thing is is the notion of a long horizon, a longunning agent. I've experienced it myself about 6 months ago. I tried to use clot code in the early days to build something. I call it a vi..."
Insights into the evolving responsibilities of product managers and designers in the era of AI.
"So capabilities and models are changing very fast. If whatever you think of 6 months ago, if you continue thinking on that dimension, you have fallen behind. So it's very very important for the produc..."
A dive into how the rise in non-deterministic software is changing the evaluation processes in companies.
"And then I think the other very very important thing that's happened which is fundamentally different is when I was growing up products were deterministic. There was a workflow you knew if X happened ..."
Reflections on the core philosophy driving successful product management in today’s landscape.
"If you think about uh my friend Zach has this great way of thinking about AI which is we had the industrial revolution for goods and that basically this kicks off an industrial revolution for services..."
Exploring the delicate balance product managers must maintain to ensure value for both users and the company.
"You can build something amazing that adds a tremendous amount of value to the customer but doesn't build any value to the business. And you can do something that is awesome for the business by raising..."
Insights into the importance of customer behavior as a key indicator for defining product success.
"So there are all these different product states or if you do a poor job they can go from becoming a loyal customer to becoming a churned customer. So these are all behaviors. Everything you do or buil..."
Discussion on the need for ongoing evaluation of AI tools and products to ensure relevance and effectiveness.
"You mentioned at the start the difference between the video transcription tool six months ago versus you know more recently and how quickly that changed. It's just such a hard future to uh reason abou..."
Advice on effectively approaching the development of AI applications amid rapid technological advancements.
"As you evaluate companies today, build things yourself and just think about this problem and the trajectory of these tools. Maybe walk through how someone should think about building an AI application..."
Insights on understanding industry needs and targeting valuable workflows for AI applications.
"So the the question you have to ask is where are what industry are there roles of people that are highly paid that are doing somewhat of a repetitive job and that can be done by software. Every 3 mont..."
Strategies for ensuring that AI applications have longevity and relevance in a competitive landscape.
"You want to target a workflow uh a way of working that is deep that is complex and that is u that is basically uh that that requires custom data. I met with the CIO of a fortune 500 company a few week..."
Exploring the need for ownership and control in developing effective AI applications amidst competition.
"So I'm just going to put them using these horizontal tools to build my AI agents. Why do you need any startups? And so that's the kind of thing you're going to face that if the CIO of a company of you..."
Discussing the shifting landscape for software companies as AI capabilities expand.
"So what that means is you've got to have durability because ultimately as venture capitalists are or even as an entrepreneur your time horizon can't be building something that lasts for one year and t..."
Analyzing the uncertainties facing existing software companies as AI disrupts traditional models.
"A control point is a thing that controls how people interact with money or with data. So if you you want to own that. Third, you want to maybe have hardware which is hard to replace. Fourth, maybe you..."
Forecasting the future landscape of software development in light of AI technologies and their implications.
"For example, in legal there's a company called Filevine or another company called Cleo. There's a few of these companies in sales at Salesforce. In in healthcare it's Epic. Now for many years these co..."
Insights into how traditional software businesses are changing or adapting to maintain relevance.
"So you started seeing last year that these companies are cutting off access to APIs. Slack has done it most publicly. Slack is owned by Salesforce. They cut off access to Glean where Glean can no long..."
Analyzing the implications of new AI features and capabilities for traditional software firms.
"And I'm hearing from other verticals that they're doing one of three things. They're blocking access to APIs. They're offering their own agents for free bundled or they're charging these AI agent comp..."
A discussion about the challenges in customer migration between different software systems and applications.
"So the agent companies have no option but to also start building and offering a system of record. So every company I know is now trying to figure out how do I build the entire platform and not just a ..."
Exploring the broader implications of adapting software development strategies in an AI-driven landscape.
"I think last year everyone was like, "Oh, we can do workflows. We can build what is called the system of action uh and live on top of the system of record." I don't think that's an option anymore."
Gathering insights on software entrepreneurship from experienced founders and their strategies.
"The Slack example is a good one of uh a sort of last generation software company which was very big and very successful. One of the most interesting investor questions and I'm curious for your answer ..."
Examining the transitions and challenges faced by software companies amidst AI advancements.
"How do you think about that question of like obviously public markets seem to think software is in a lot of trouble. The multiples are really really low. How much would you be worried if you ran like ..."
Discussing how companies should adapt pricing strategies in light of AI-driven competition and customer needs.
"There are two or three kinds of software companies. I think the the software companies that are should be the most worried right now is where they are pricing the product based on utility. Zenesk is a..."
Exploring the necessary changes software companies need to make in response to emerging AI technologies.
"So that company should be worried. Why? Because I can have an AI agent sit right next to Zenesk and you can slowly siphon off. You can use instead of paying for 50 Zenesk seats, you can pay for 20 and..."
Understanding the need for software companies to innovate their business model amidst competitive pressures.
"You need to change your pricing model to be based on outcome and you need to actually build the product to be based on outcome. It's easier said than done because literally you're going from a 20 or $..."
Strategies for existing companies to adapt and compete against emerging AI-driven firms.
"That's why I think many of them probably need to go private because they have to make this business model transformation in private. I think it's going to be hard for them to stay public."
Discussing the types of software companies and their varying degrees of vulnerability to AI disruption.
"The companies that are less exposed are ones where the utility is not based on seats but it's based on data that has been collected and captured over a period of time and the the more uh timeless the ..."
Understanding what makes software applications sustainable amidst rapid innovation and competition.
"Slack for example I would say might be in a little bit more precarious state because the data in Slack is half time halfife is very short that's a great way of putting it but if you have ERP is a grea..."
Evaluating the role of data protection in sustaining software companies against AI competition.
"There are legacy or somewhat new what is called a system of record which is a system where most of the data is stored for that system. For example, in legal there's a company called Filevine or anothe..."
Understanding the complexities of migrating customers from legacy systems to modern solutions.
"Now for many years these companies all had APIs that if you enter that industry you could build an agent company on top of these APIs. In 2025 things changed. These companies started seeing that these..."
Exploring the shift towards autonomous AI solutions and their implications for software development.
"So you started seeing last year that these companies are cutting off access to APIs. Slack has done it most publicly. Slack is owned by Salesforce. They cut off access to Glean where Glean can no long..."
Implications of evolving software landscapes driven by AI and market competitiveness.
"I think it's going to be very hard for a end customer to use multiple companies where you have a system of record and then you have this agent that sometimes doesn't work with it properly."
Exploring the pitfalls and failures within advertising business models and strategies.
"What business ideas don't work in in advertising? Like what are the business models that just are doomed to fail? >> Trying to be a middleman on top of these large platforms from my understanding work..."
Exploring the fears of executives within monopolistic ad networks regarding platform dependency.
"What would you be worried about if you were one of these fairly monopolistic owners of a massive ad network like the ones we've discussed? There Uber and Amazon in the mix, Door Dash, Facebook, Google..."
Analyzing the implications of being a second mover in the ad network space and the importance of engagement.
"There's a new battle happening for that first category which is a new interface to be owned. We know chat GBT is sort of does I'm curious if you think being the first mover matters to build a new ad n..."
The evolving job landscape and skills needed to manage AI agents effectively in the workplace.
"So like fully fully self-serve. Love to hear you talk about that. And a related idea was that's sort of on the builder side. On the investor side, you mentioned to me that all the great investments th..."
Effective methods for assessing candidate capabilities through practical demonstrations.
"And so I think that's what you want. You want somebody who is essentially acting as a manager but not of humans but of AI agents. And management has to be a full-time job. What I mean by that is if yo..."
Examining the importance of advisory boards and relationships to support a company's growth.
"I think good example is the Collisons I think bought a book on payments and they studied exactly why all the payments companies did what they did and how they failed and how they succeeded and I think..."
Transitioning from traditional selling models towards those focused on collaborative outcomes.
"I think one of the best practices I've seen done and I've I've now tried to push other companies to do it is a notion of a board buddy. So everyone on the board should become a buddy to manage team me..."
Harnessing influencer power to enhance brand visibility and guide consumer decisions.
"I think influencers have become much more every year they become much more powerful in how people especially younger people consume products and and even choose products."