The Exchanges

Q What was interesting about working with Andy Radcliffe on the business?

A Andy, of course, has a long history as an investor. And by the way, not a, not a small one. I mean, Benchmark is a relatively new firm in some ways. I mean, now it's been decades. But I mean, it was, you know, born in the nineties. So the fact that he had been there at the beginning of benchmark, his dedication to understanding why the venture model works and about the entire venture ecosystem was really quite deep. And so we immediately got along on all those fronts. Cause I also, I, I didn't have the experience that he had, but I had the same passion for the industry, et cetera, a little bit, probably more biased on the operator side, right? I'd come up as an engineer, right? As an engineer, I was a designer. I was a product manager. Very often he was someone who had the frameworks and also the patterns of this is what success looks like. These are the problems we have to sign next. And I love coming up with solutions to problems. And so we, we worked really well together. I think framing and, and, you know, on those different pieces, most of my memories, when I think of analogies now, I, I even teach a class at Stanford, personal finance for engineers in my spare time. There's always a request from the students to talk about venture capital and private equity. And inevitably I always end up Having some quotes or insights from Andy in there.

AI assessment note: “he was someone who had the frameworks and also the patterns of this is what success looks like”

Q In contrast, what did they think of themselves as?

A They thought of themselves more as applications. And so they thought of themselves as like, no, no, it's an app, right? Even the original website guys was very much like, oh, I'm going to build an app, but instead of it rendering windows on an OS, right? In a GUI metaphor, it's going to render web pages, but it'll have buttons and you can click and you can do things and actions and it'll have data store. And there was some debate, is the data local? Is the data in the cloud? We have fights about everything. You can always, Debate different architectures and things. But, um, I do think that the web one O companies, some of it was because they absorbed some culture from the media industry. So this idea of a producer, I mean, some of the original idea of a product manager in the web was a little bit of fusing historically what a product manager had been or a program manager had been in client-based software with a little bit of the media world, right? You had this advertising business model. People are talking about eyeballs. So a lot of the energy comes in about producing Why are we producing content here? Is it an application? Even that was a fight, right? Some people thought of the web as content. Some of them thought it as an application. But my epiphany eBay was at least for a marketplace, it's really a platform. And what that means is that when you build new functionality an…

AI assessment note: “They thought of themselves more as applications.”

Q And did you have times where they were highly overlapping or most of the time they actually weren't?

A Oh, it's so rare. There are exceptions, right? Because actually some great product insight comes from customer requests and they'll report to you the problem. Your team comes up with a solution and sometimes you go, oh, if they want that, I mean, some of the best features of Daffy, my current company, all based on customer requests and interpreting them and figuring out how they fit into our strategy. But then I discovered at LinkedIn that even if you have a queue for metrics movers and customer requests, that's insufficient because you'll end up building a product that does move the metrics. Teams will do that. And your customers will like you, but they won't love you. You won't have this irrational attachment from them. And as I dug into that problem, I went back to actually my earlier Apple experience and this framing. It's now become very fashionable to talk about delight. Everyone talks about delight. No one defines it the same way. But one of the great things about the Apple experience is that Apple has a core belief at some level, almost genetic memory, that delight isn't rational. And a lot of it comes from surprise. Actually, Tim Cook gave an interview once with Kara Swisher. I remember this. Kara was bugging him about, what are you gonna release next? I think everyone was talking about the TV at the time. I don't know if they were talking about the car or whatever. An…

AI assessment note: “Oh, it's so rare. There are exceptions, right?”

Q How would you articulate what the company strategy was, and then maybe the product strategy, or some of the product strategies in the areas that you were spending time?

A Well, to see the product strategy in LinkedIn, to be very clear, was Invariably read. And even as a fact, even when he stepped out of the CEO role and was chairman, he kept his hand pretty directly in product. He might even argue too much at some times. And then once he actually stepped out of that, he still was giving guidance on the product strategy piece. So I would never claim to have had the seat of that for LinkedIn, but it was very important that same process for the parts that I did run and control. Like I said, I was running core product and that was not just for product. It was also, you know, when I was running the user experience and design team, why does LinkedIn You need user experience in design. Strategically, how does that fit into the company strategy? How does it fit into the product we're building the people? And what does that tell us about what we, who we need to hire and how we prioritize? Every function that I ended up running ran that way. But, you know, for example, LinkedIn mobile. So in 2009, I was handed LinkedIn mobile. It had been literally a fun, innovative thing that one of the engineers had built. We had an intern over the summer work on actually keeping it up, but we did not have a heavy focus on mobile. And it was because when I took it over, I realized that there was no product strategy for mobile. Other than, like, the iPhone is cool.

AI assessment note: “I realized that there was no product strategy for mobile.”

Q Can you explain this idea of shifting the perspective that you're not building an app, you're building a platform? Can you kind of share a story or a big product that you worked on that's like a direct consequence of seeing the world in that way? It could be at LinkedIn. You were talking about the, the listings project at eBay.

A eBay, um, I got that realization late, that mapping to the web. Although some people had it much earlier, and I probably was influenced by a number of folks who had always had the technical underpinnings of thinking of the web as an operating system. I mean, going back to even, you know, I know Mark Andreessen has some great quotes about this in the very, very early days of the web. But actually, I got it even before I worked on a product, even as a consumer, right? You know, this is probably one of the first clues that I was destined for products some way is that, you know, you think about these things, right? So what was one of the first applications on the personal computer that I thought was new and And amazing to me. It actually was a spreadsheet. And actually there's a story at some point. There was a point where I think I was nine or 10 years old where actually, um, my father was renting out an office and he asked me to make a table to plan out a mortgage of like what the payments would be. And I did not know what a mortgage was. I might have been 11. I don't want to over sell the case, but he explained to me the basic rules, right? The payment has to stay the same. There's an interest rate, all these things. The one thing I knew about spreadsheet is that let me organize Mathematical functions, and they could be dependent on each other. In a way, it's like a lightweight …

AI assessment note: “one of the reasons Excel was so sticky was it wasn't just an application”

Q What's so interesting is that he had a long career as an investor and then went and started what became Wealthfront and ran that sort of on again, off again. In the realm of company building, are there specific perspectives that he had that kind of stuck with you or updated any of your priors?

A This is actually some of the advice I give founders as well in building companies. There are some founders who believe that their investors are like this This is necessary evil. This problem. I need capital. They have the money. I need the money. What do I need to tell them? By the way, more unsuccessful salespeople also have this philosophy. They think selling is about somehow it's a trick, right? Like there's some pattern to get you to pull out your wallet. The best salespeople actually understand the customer's problem and understand how they can solve it. And so that's a much better process. I feel the same way about investors and board members, right? I always tell founders that financing is actually a hiring decision. The investors you have, the board you have, Incredibly path dependent. A lot of your opportunity depends on having the right people with the right motivations involved. You don't want to sell an investor on something you're not because then when it inevitably comes out that you're not the thing that they want to back, they're going to focus elsewhere, right? They're not going to support you or worse. They might push you to do things that are unnatural or not right for your business. And so having Andy there was always having that frequent access to a board member so that you didn't forget. It's so easy within a company to start focusing on purely operational…

AI assessment note: “having Andy there was always having that frequent access to a board member”