Operators Ep 34 Transcript

Delian:

Hi everyone. My name is Delian and I'm a principal at Founders Fund, a venture capital firm based in San Francisco. This is Operators, where I interview non-VC, non-CEO, non-founder operators that make the startup world go round. Today I'm interviewing Anand Chandrasekaran, an EVP at Five9, which was recently acquired by Zoom.

Delian:

Prior to joining Five9, Anand worked at Facebook, Snapdeal, Yahoo, and Aeroprise. He has a master of science in electrical engineering from Stanford and is currently on the board of Future Group India. I hope you enjoy the show. Well, Anand, thanks so much for coming on the podcast. I'm really excited to have you on today.

Anand:

Yeah, absolutely. Thanks for having me Delian.

Delian:

You guys have gone through some interesting news. I'm sure we can't necessarily talk about all of it between the Five9 Zoom deal, et cetera. And we'll get to that. But I typically like starting these conversations by sort of going all the way back to the beginning of folk's careers.

Delian:

You actually grew up in India, so obviously outside of the United States, and always had sort of like a lifetime goal, it sounds like, of eventually ending up at Stanford. And so you did achieve that goal. You did electric engineering at Sanford. I'm just curious, what was the sort of like motivation? How did you even hear about Stanford? Why was that sort of the ultimate goal? Did Stanford sort of live up to the experience?

Anand:

Yeah. That's a great place to start. So I actually grew up in a small town in India. I heard about Stanford for the first time when I read Only the Paranoid Survive by Andrew Grove. Still one of my favorite books. He was a guest lecturer, if I remember correctly, at Stanford. I was pretty blown by how people who are practitioners are coming to college and teaching a business course as the story is unfolding when he was running Intel.

Anand:

I was like, that sounds like a pretty cool place. I was also really kind of blown away by meritocracy trumping everything. This is probably true of like many other countries. But in India, like many other countries, your destiny was kind of determined by kind of the entitlement, like if you're born in the right family, in the right city, and so on. And this idea that meritocracy trumped everything was also kind of like pretty cool for me.

Anand:

There was one problem, which is no one from my college in the last 70 years had ever gone to Stanford. So there was no small group of people who are dissuading me from having that kind of ambition. But really, I think the theme there was if you shoot for the stars and you really miss, at least you get to a skyscraper. I'm going to be no worse off if I try to shoot for the stars and then fail. And I think that theme has stuck with me through the last couple of decades or so.

Delian:

And then right after graduate school, you decided to co-found this company, Aeroprise, where you were alleged folks sensor and product marketing. Can you talk to us a bit about how you already took the risk of obviously moving across the world, how you decided to take the risk of actually building a company? And how did you end up sort of landing on sort of what you were sort of core focusing skillset given that it's obviously different than the sort of Stanford degree?

Anand:

Yeah, absolutely. So when I landed at Stanford, it really felt like a place where everything or anything was like one step away, whether you want to develop breadth or depth, or what have you. And like most people in 1999 at Stanford, I was bitten by the entrepreneurial bug fairly early and was working on a class project, honestly, by professor Armando Fox, where we had built this prototype that stored data independent of mobile device and the source app.

Anand:

And we would show it to a bunch of industry and academic advisors. And with most other teams, the advice was, why don't you go read this paper or talk to this team and universities? And when people saw our prototype, it was really like, "Talk to this company. See if this company would want to acquire this." And so we saw that there was like a bunch of commercial appeal in what we were building and ended up sort of using the momentum there to incorporate a company and start off and call it Aeroprise.

Anand:

We were just students at the time. No one told us that it was the worst time in like 25 to 30 years in corporate America to start a business. It was like the bottom of the dot-com burst and all that. The honeymoon was a very short honeymoon before we realized it was a very tough general environment.

Delian:

And then you actually ended up having an acquisition outcome for the company of BMC Software. And then you took some time off before joining Yahoo, where you joined it, I think, I was unfortunately in high school at the time. But I feel like it must have been a very interesting time in Yahoo's history. A combination of obviously this market that you previously had a stranglehold on now having this sort of up and comer, Google coming to the market.

Delian:

And also at the same time, maybe like massive disruption in terms of new platform, I.e mobile. An iPhone really becoming quite popular, which is where you focused some of your efforts on. Can you talk a bit about the early days of mobile, that partnership that you built with Apple, growing that to actually have a pretty significant revenue line for Yahoo. What was even the process for sort of landing it and what was it like sort of navigating a very, I guess, tumultuous time, I'm almost sure, just so many fundamental things changing about how that business was running.

Anand:

So this was actually kind of a big transition for me. I was in "enterprise software" before was even SaaS during that time. And there were a couple of things that I really didn't like about it, the big things being that you were not talking to users that much. You were talking to all these powers that were buying the software that often were more powerful than the end user. And so you were not in this like empathy loop, user feedback loop in the enterprise software world that I was in at the time.

Anand:

And also the development cycles were like pretty long. The rollout cycles were often quarters, not even months, after the decision was made to buy a certain piece of software. I was sort of looking... The grass is always green, I guess, on the other side. But in consumer it felt like the cycles were really fast. You were getting user empathy, user feedback cycles going really quickly and everything was instrumented so you were seeing sort of the forest for the trees rather than just talking to individual users.

Anand:

The thesis was you could compound on top of that fairly fast, and you were seeing companies like Facebook, et cetera, and Yahoo at the time benefit from those cycles. And so I found myself sort of transitioning from B2B to B2C on the back of the iPhone that had just launched. And so it was clean as a day that this was going to be the preeminent development platform. I also really liked the consumer scale that Yahoo had at the time. So even though it was sort of probably not the best years for Yahoo when I was joining the company, I was like a kid in a candy store.

Anand:

My products were used by tens of millions of users. I was developing great products on the back of the iPhone iOS partnership. If you recall, Jerry and Steve had signed this handshake deal when the iPhone came out that they would mutually sort of compete against Google. And so this ended up being a great source of traffic as iPhone was growing in the US and abroad for Yahoo. I think the big insight there was we didn't know what to do with that traffic.

Anand:

It took us a while to realize, hey, this is really a search page. Because people are clicking on the white bang on whether a page or a sports page or entertainment and they're landing on a page where they're looking for more information. And so there's really a search page. You got to give them more information, try to disambiguate their intent. And then if we're lucky, keep them on that page for a really long time and monetize through search advertising.

Anand:

It was also interesting because I also realized that in B2B, the product and the business model are the same. All the engineers, all the product people work on building features and you sell it to the customer and the business model is baked in. If you build the right features, they pay you and that's the economic relationship. Whereas in consumer, particularly in search and advertising driven products, there was a chunk of your product team that was not building product per se. They were building the monetization layer.

Anand:

So that was pretty new to me. It was quite eye-opening that you had to make that deliberate choice to take a bunch of people off of building consumer features that would benefit the consumer directly so that you monetize, which allows you to build more consumer features. So you're actually making a pretty deliberate call to focus sometimes on monetization.

Anand:

One of the things that people don't probably know or recall is that Yahoo actually had about 15% of mobile search market share, which is really hard to believe if you think about it now, because Google launched Android and combined search and Android, and of course the rest is history. But Yahoo at the time was quite a bit of market share leader.

Anand:

The other big takeaway from that time is owning the whole stack does matter. So Yahoo did the relationship with Bing, where the algorithm for search was actually coming from Bing. But what happened as a result was that we were not getting the search feedback. If the first link or the first result was not the best link for something, that feedback was going to a partner and not to Yahoo directly.

Anand:

And so sometimes the extra investment that you make to own the whole stack actually really matters. And then the other thing you were asking is, what happened when you moved to mobile? The big change there was people were very frustrated about clicking on links. You were seeing the shift from wanting to click on a link on a desktop, on a PC screen and PC bandwidth to wanting an answer. So one of the things that we tried to do was bring the best content right to the first results, that people got answers, not links.

Delian:

Makes a lot of sense. Yeah. Can you talk through a bit of both, as you're sort of spinning up sort of net new revenue line, product line, sort of how the company sort of resourced that back and then how do you sort of prove it out and then how do you start to build out the team? I'd love to talk about the dynamics of just like, yeah, in some ways, building that monetization layer is very necessary to be able to continue to build up a team.

Delian:

But I'm sure also there's some level of bias in there, like the best engineers don't necessarily want to work on that. They want to work on things that are sort of like purely user-facing. And just like how you even manage a culture around that, where there's sort of this like necessary evil that's required to sort of keep the shop running.

Anand:

Yeah, absolutely. I think the biggest thing I learned was in enterprise software, in B2B, in general, there's this phrase called maintenance mode. If something is in maintenance mode, you're just milking the asset and you're making a lot of revenue, but you're not investing in new development. On the internet, there's no maintenance mode. If you're not growing, you're declining.

Anand:

And there's no in-between state. You either are investing in new product and leveraging the momentum of user traction and growing or you're declining. There's no flat, and flat is the declining. And so what we were doing was sort of do this combination of we've made some money from the search deal. We're not building search anymore. Why don't we redeploy it in other areas?

Anand:

So I was involved in a lot of the mobile app reboots that Marissa did after she joined the company. One of stories that I recall is, are we actually building on this answers not links idea? We said, look, there've been a bunch of battles that have happened on the internet and there are now winners. So in local, for instance, Yelp is the winner. We're going to bring Yelp data into Yahoo local search.

Anand:

And of course everybody went, "No, you're not. We're big competitors. We're not going to get our deathly competitors content into our search pages." What sort of my battle was, was to convince everybody that the only people who thought that the battle was still happening was inside Yahoo. Everybody else already believed Yelp was the winner. And so I had to kind of move some folks into accepting that if you had to grow, you had to bring the best in breed.

Anand:

And you were sort of the tasteful curator, that you were bringing the best of breed content. So that was actually a big reboot. we grew local search quite a bit on the back of the Yelp relationship, for instance, which a great example of, sometimes ideas that were accepted as reality have to be questioned when the world changes. There's new information and you have to adapt, even in large companies.

Anand:

I think the other really interesting thing was this notion of generalists vs experts. So one of the things that Yahoo had done was brought in a lot of "experts" who were really good at middle management, who were really good at processes, were really good at systems, but they were not good at zero to one products. So if you had to get into wartime more and build something from zero to one, that was not the strength that they had built in other companies, but they had learned to build teams and process and all of that stuff.

Anand:

And then also in my team, for instance, separating out the product skillset to build zero to one from the skillset to do one to one, which is, look, you've launched a product in the US. It's really successful. Now roll it out in like 30 different countries and then start to monetize it. There are certain PMs who get really frustrated when you put them in the one-to-one roles and you've got to find the next zero to one role for them.

Anand:

And then the opposite. There are certain people who get very chaffed and they don't have any resources. And it's like a four engineer team where they have to build a prototype in like six weeks. They want the larger team, the portfolio. And so part of it is also the talent management around, which is the skillset that you want each product leader in your team to be in?

Delian:

Yeah. I guess, did you have ways of sort of clearly assessing this as you were sort of upfront interviewing and you've sort of taken a long view from your companies as well, where you sort of in the up-front process, try to assess whether this sort of product manager role or product manager candidate is more of a zero to one versus a sort of like one to one? How do you assess that out in the upfront, or is it only really possible once you sort of place somebody in that situation, they kind of recognize that on their own best?

Anand:

Yeah. I think some of it you do see in their proclivity to like work nights and weekends on certain projects, whereas some they're not that deeply involved. And so it's just like the level of passion. But also I found that if it's a former engineer turned PM or a former designer turned PM, they naturally gravitate towards the zero to one things. They like to just make things and keep tweaking. It's just naturally why they decided to move from engineering or design to product. So that was sort of one prototype.

Anand:

The other one is there are some folks who know how to manage things like optics within a large company. I think you'd be naive if you said that wasn't important, and that's more a one-to-one skillset. Whereas someone who manages outcomes and who has no patience or no proclivity for optics and things like that is probably more zero to one, or hopefully they are zero to one, because they're no good in the other side.

Anand:

I think it's also there are people who naturally because of their previous life experiences or work experiences gravitate towards risk minimization and they're better in the one to one stage. Whereas there are people who are in the outcome maximization focus who are probably better off in, what's in the initial MVP? How do you compete against the incumbents? Are they better in the zero to one focus areas?

Delian:

And given we are talking about product, let's dive into maybe the most controversial aspect of product, which is what exactly is a product manager? There are some people that even prefer to call them project managers versus others that require that the product manager actually has product sense design skills and actually sort of take that on entirely themselves. I'm curious, what has been your philosophy on that for most of your career? Does it actually vary back and forth depending on the company culture or depending on the exact product and what's best there for it? How do you typically think about sort of what are the skillsets and sort of responsibilities for a product manager?

Anand:

Yeah. I mean, overall, I feel like other than the CEO, the product manager is probably one of the few people who's looking 360 degrees at like every aspect of the company's product. So in that sense, you're the steward of every part of it and you're hopefully doing some systems thinking around every part of it: the economics, the psychology, the motivation, as well as the actual execution and delivery, in addition to the overall problem statement that you're solving and things like that.

Anand:

It's probably no surprise that a lot of product people end up becoming founders and CEOs and a lot of CEOs are so product-minded because the two frameworks and systems are like fairly similar, because you're thinking about the whole system. That being said, I think the difference is everybody does at some level report to the CEO, whereas almost nobody reports to the product manager, especially if you're junior to mid-level.

Anand:

So you're sort of turning on first principles based and more systemic arguments are an influence to win arguments rather than command and control, or like, "It's my company. I told you to do that." Which very rarely works. If it works in the short-term, it very rarely works in the long-term as a product manager. I think it's also you're building the empathy and the relationships inside and outside the company.

Anand:

And you're building sort of, what is the battle that you're picking off right now? And deliberately allowing some other battles to fester, some other fires to fester, so that you're bringing the entire focus of the company and of the product teams onto fewer and fewer battles. And you're defining the battle in a way that the focus can actually happen as opposed to chaos and indecision and multiple battles and so on.

Anand:

But it's also a function of what stage the company is in. If the company has no product market fit, one of the things I do as like... I've done a bunch of investing and advising and sometimes you start to play operator before you have product market fit. And that's one of the biggest temptations is that you're exhibiting and demonstrating skills that are not that much of a fit for the stage.

Anand:

So to also kind of unfurl your product management skills based on the stage of the company. But I actually think done well, it's actually someone who's demonstrating taste, demonstrating judgment, demonstrating focus, demonstrating the ability to rally a bunch of people. But it's a hard skillset. And you see people from different backgrounds also come into this because so many starting instincts can be relevant to be a great product manager.

Delian:

And so after your at Yahoo, you ended up deciding to go back to the homeland and join Snapdeal, which has obviously been a runaway success. I believe it's one of the largest sort of private companies in India. I'm curious, how did you end up deciding to make that transition? How did you think about sort of the geographic switch, and then also sort of technical architecture switch at that point, staff deals, platform was largely Android, and so a different sort of mobile platform than you'd been operating in for the prior sort of four or five years.

Anand:

Yeah. So that was, again, a big sort of zero to one shift for me career wise and in terms of what I had learned and instincts. Like most situations, it's like opportunity meeting preparedness in some sense. So I had been seeing traffic from India and China grow significantly when I was at Yahoo across every property. And in many other countries, we were spending some money or partnerships in traffic acquisition, whereas in India and China, it was just completely organic.

Anand:

And so I knew something was going there, new users coming on board, people leapfrogging PC into mobile usage, et cetera, going back six or seven years. And my question was if the internet is actually happening outside of the US and in a culture that I understood reasonably well, do I want to be a bystander or do I want to be kind of a player in what was going on? And in terms of marketplaces, the metaphors were already there.

Anand:

We saw early examples of like eBay and PayPal. In the end, it ended up being unsuccessful, but the concept was very powerful. That you would create this flywheel of something that people used every day, like PayPal for payments, and something that people used infrequently, but there was deep emotional connect, like eBay, to create a very powerful flywheel. And in China, the same thing had happened with like Alibaba and Alipay.

Anand:

And so I saw the parallel between that and Snapdeal and FreeCharge, for instance, where you could bring the eBay, PayPal, Alibaba, Alipay metaphor to India. And so it was kind of insane. I showed up and realized that like 5% of our users were coming from iPhone. And I'm like, "Holy shit, this skill that I built my entire career," where you'd launch a product, you'd take it to Apple, it would be featured on the first weekend, you get your first million users, and then you go from there.

Anand:

That play doesn't work because there's no concept of Android featuring leading to all of those users. And so it was like classic unlearning and realizing from first principles what would work. And so the big thing that I did in terms of personal change was picked up a trick from what Marissa did at Google, where apparently she would use AOL until 51% of US subscribers started using DSL.

Anand:

So she wanted to mirror her internet access. I had to mirror her 51% of her consumers internet access. So I'm like, well, one way to develop empathy is that I'll give up my iPhone and use an Android Jelly Bean phone, which was like two generations old. And sometimes the green key would barely work on the screen. A lot of people would be like, "Look, you're making good money. Why wouldn't you buy a new phone?"

Anand:

But I wanted to kind of empathize with the largest percentage was at that point using Android Jelly Bean. And so I'm like if my products work on my phone, it probably works for like 51% of subscribers. And started doing these rigorous product reviews, because what I realized is some of the things transfer from the US to India and from iOS to Android, which is people are bored, frustrated. They're not going to give you a second choice if the first impression isn't great and the user onboarding, the next onboarding isn't great.

Anand:

And so we just built these incredible products. And sort of the proud moment for me was being in an Indian company for the first time. I had I think three apps, which were like number one in the top three apps on Android within a space of like three or four years. It was just purely through first principles. But it's also this hunger towards market access. So if you're in India and you're not in one of the four or five big cities, you don't have access to malls.

Anand:

You don't have access to high quality merchandise. And so e-commerce was really bringing market access to the next 100 to 200 towns. And so there was obviously huge kind of appetite for that. And so we really grew on the back of solving a huge problem for, I think at the time we had like 65 million monthly users.

Delian:

And speaking of things, translating from Yahoo/America to Snapdeal/India, I'm curious if there were sort of cultural differences in terms of just like how companies operated or how product decisions were made that maybe took you some time to adapt since you had sort of, despite obviously growing up as a child in India, you grew up as a sort of product manager and product focus executive within the United States. What were some of the things that didn't maybe immediately translate? There were just aspects of companies just being differently culturally run on a different continent.

Anand:

I'll give you two things, both a little funny, but they were not funny to me back then. One was that I was communicating with a lot of folks who didn't have a technology background, but they understood business really, really well. What I realized was that my job was really taking business challenges and translating them into computer science problems. And then solving the computer science problem that then solved the business problem.

Anand:

But I had to find a language where we were communicating the same way. I had some incredible friends, still lifelong friends that I made in like working side by side. One thing I realized is while they didn't speak the technology lingo, they understood first principles. So a great example of this is you know when a product is designed well and it's just a high quality product.

Anand:

So while a lot of folks that I worked with on the business side didn't understand engineering and coding and high quality versus low quality and bug fixes and all of that stuff, when I had to delay a product launch, all I had to tell them was the difference between high quality soap and low quality soap, because they'd all sold soap their entire careers. And they could understand high-quality soap with like a high quality brand ambassador commanded 80% margins and low quality soap with a low quality brand ambassador commanded only 25% margins.

Anand:

So they understood that with a very different metaphor. But as long as you were talking first principles, you actually got through to people who didn't have the same skillset that you did. So culturally, that was actually a huge enabler for me, because it allowed me to not be seen as like only someone that they could partner on a limited set of problems. Now we were talking about business strategy and marketing strategy and what were the real strengths of the product that had to be amplified when a TV commercial came out?

Anand:

Because TV advertising is like in Vogue in India, unlike in the US, for instance, where only when you've crossed a hundred million consumers you do a TV ad in the US for instance. So it allowed me to really communicate with people who didn't start from the same technology background that I did. The other thing, and it's probably true of many other countries, is the existence of this really deep gossip mill.

Anand:

So when I joined, I actually realized that there was a top product manager on my team who was paid in the lower bracket of pay in my company. And so I very quietly fixed it and moved him to the higher bracket. And he showed up and he said, "Thank you so much for doing that. I know I was getting paid less than A, B and C." I was like, "Wait, how do you do that? How do you know that? You're not supposed to know people's salary?"

Anand:

And he's like, "Oh, don't worry about it. Your HR business partner is my wife. And we talk about this stuff all the time." After having to pick my job from the ground, I realized that there is a gossip middle that's there in India which you can't run away from. So you might as well lean in and embrace it and try to place the things that you believe to be important and you believe to be critical into the gossip mill.

Anand:

So we started promoting people who are like really collaborative and then placing that into the gossip mill. And soon people got the sense that people who collaborated well got promoted. And literally within a few weeks, people just started collaborating, not because that was the right thing to do, but because the people that did that got ahead. And so it's just funny how much of that that gossip mill is still there, that you could actually choose to lead in an embrace or choose to run away from.

Delian:

It's kind of just like the career equivalent of the strict Indian parents all gossiping about who has the best grades. That same gossip exists in the professional world, basically.

Anand:

Exactly. You hear that the level of hustle that these founders have outside of the US is just insane. We see them in the form of immigrants who come here and bring that hustle. But imagine that in like every single product manager on your team and that's sort of the basic level. So oftentimes I had to manage the deadlines and how hard I wanted to push people, because they would literally walk through fire if I asked them to, but it may not be the right thing for the product. And so it was actually kind of an interesting internalization of like, how do you have that level of hustle by default?

Delian:

And so after two years at Snapdeal, you ended up deciding to come back to state side and joining Facebook, I guess. What was the sort of decision making around that, given that Snapdeal was on quite a trajectory? And then sort of as you were debating as in coming back to opportunities, why did you end up deciding to join Facebook?

Anand:

Yeah. So I would say the experience at Snapdeal was phenomenal, but also mixed. At the time when I left Snapdeal, there was also this well-publicized disconnect within the board. And the founders actually were asked to merge with another large e-commerce company, Flipkart, to form like a single entity that would take on Amazon in India. And the founders sort of decided to pair down the company significantly, but ended up not merging. And so the entire management team pretty much churned out at the time.

Anand:

And so for me, the thinking was, well, I don't want to sort of give up all the learning and the instincts that I picked up working in India. We also had Alibaba and others as investors. So we were traveling to China every six weeks or thereabouts to learn from their experience building in the China ecosystem. And so the opportunity sort of came to join Facebook. Facebook was about 7,000 employees when I joined and my initial instinct was, well, this is a little bit too big for me.

Anand:

But Messenger was still the set of features within the Facebook app. But it was being spun out as a separate app. There was really no leadership team or no product leadership that was there at the time. And so the job for me was like, do you want to go build Messenger for Business as a platform? And the thesis was in China, messaging was really used as a path to doing almost everything.

Anand:

Could we bring some of those same instincts to a global messaging app? And Facebook was one of the few people that had that scale. And so the thesis was, hey, if you are meeting Delian and you're late, you can message Delian and say, "I'm 10 minutes late." But why can't you do that to the coffee shop where you're meeting him and why can't the coffee shop use some AI to change the appointment or move the reservation or do all these automated actions on the other side?

Anand:

And so Facebook at the time had I think about 60 million pages. And so the thought was, why don't we convert all the 60 million pages into bots, apply a layer of AI so that they can take intelligent actions, and then have like a meta bot that has intelligence and can direct the user to the right bot based on intent and time of day and user's past behaviors and things like that?

Anand:

So that was sort of the huge lofty messenger vision, which sort of was going through the hype cycle when I joined. People thought bots could do your laundry and drive you around and things like that. And you realize that the AI was just not there at the time to automate all of those things. And so my job was really to bring some quality in addition to the quantity and start to bring these incredibly high quality product experiences.

Anand:

So it's really to bring a product mindset to building a platform. And so I loved that. I ended up realizing that when you're operating at the scale of Facebook and Messenger, a lot of ideas just don't work because they have to work out of the box in like 60 to 70 countries. It can't be like something that's cute, but works in like two countries. And so it's a very special challenge to try to do that at global scale.

Anand:

And so we started with like content commerce and customer care. And content of course we stopped very quickly after Cambridge Analytica. And that may be one of the smart decisions that Facebook made to not move all the content stuff that was going on in the blue Facebook app to Messenger. So Messenger sort of got left out of all the other fallout of CA.

Anand:

And then commerce we realized it was harder than we thought to build it across 60 to 70 countries while taking care of fraud and all of the heavy lifting that has to happen on the backend. It works in all the Western markets, but the payments infrastructure were not as sophisticated in every country to roll out globally. And so we really doubled down on customer care as a way.

Anand:

It was the use case that I told you, which is, can we automate all of these two-way communication between brands and consumers, consumers and brands? And on the back of that, I think we grew from zero to about 350,000 developers, about 8 billion messages per day between people and businesses, which is like a 100 million when I joined. So insane amount of scale. And really had this agent called M recommend bots that were really high quality.

Anand:

I don't know if you've heard this story, but in about 14 years, Facebook would always build on top of Apple's platforms, but Apple had never built on a Facebook platform. And so for the first time we got apple to build a music bot on the back of our messenger APIs. And that was one of the highlights of the 2016 and 2017 F8 that we joined. So it was pretty fun times to go from a sort of, hey, this is an interesting idea to this is now how people use the Messenger app.

Delian:

If you had to point to sort of the most impactful initiative during your time at Facebook, where you pointed towards that sort of like increasing the B2B communications or while you're there, the app reached a sort of user mark. What were the things that you feel like you sort of had the most impact on that helped achieve that milestone?

Anand:

Yeah. I would say it's probably just making it one of those. People don't think about it as like a uncommon occurrence anymore. It's fairly normal to buy from Instagram and get your order status on messenger at this point. That's almost 20% to 25% of all the communication that happens on messenger from a B2B perspective, people to business perspective. So that was pretty huge, trying to get brands like Apple and Spotify and T-Mobile and Sephora.

Anand:

So Sephora actually, a funny story was they have all these girls waiting on Friday nights to get a makeover and they build an appointment bot where you can get an appointment and get the value of your make-over in free stuff if you went to Sephora. So it's actually also going back to the China inspiration, where some of the online meets offline use cases.

Anand:

So they actually cleaned up the crowds outside the Sephora store by building an online experience that worked when they went to the store. So that was, again, fairly interesting. And then that business is like a multi-billion dollar business. We talked about how when the consumer experience starts to grow, you have to dedicate a bunch of engineers to build a monetization experience. And so once we started growing the B2B communication, we were actually able to build the ads that worked on messenger and start to grow that business quite a bit.

Delian:

And then after about three years of Facebook, you ended up leaving for a an EVP role at Five9, which was sort of your first foray back into B2B in quite some time. How did that sort of role come about? How did you decide to sort of step away from consumer land? And obviously some interesting news, which I'm sure we can't talk too much about around sort of an acquisition offer from Zoom. When we actually first put together the questions, that has since changed.

Anand:

That's right. Yeah. So like I said, we leaned in quite heavily on customer care when I was at messenger and I saw a lot of those use cases take shape in terms of what large businesses would want out of an omni-channel experience like messenger. The exercise for me was if this is the demand from one platform in one country, how big could this be if you could roll out these experiences across all your channels, but also unified those experiences in a single platform?

Anand:

So if let's say I was talking on messenger, and then my next chat was on WhatsApp, and then I did a call, and then I worked with one of your bots on your website, I don't want to repeat anything across all of those channels. And my question was, are people already doing this, or is this a new business idea? And as it turned out, there were a couple of companies that were doing it not natively on the cloud.

Anand:

But my sort of thesis was people wouldn't want to bet on a last generation platform. They would want a native cloud platform. So in B2B, if you now are buying Salesforce automation software, when you talk about older generation apps, people will laugh you out of the room. You're talking HubSpot and all these modern experiences, or even salesforce.com. And so my question was, why isn't that happening in customer care?

Anand:

There's no native cloud platform. Well, as it turned out, there was one that had recently gone public called Five9 and they had hired this leader from Cisco who, by the way, had also bet on some of the same things that I was sort of seeing from Facebook. I think that's probably a big thing that's worked for me, which is to kind of independently have these TCs for what would happen in the space, particularly if you've got some operating experience and looking around the corner.

Anand:

As they say, you want to be right either before everyone is right or when everyone is wrong. Those are really the big wins, where you either saw something way before everyone else or you saw the opposite of what everyone was seeing. And so in this case, I would say when I joined Five9, it was about $2 billion. I thought if we doubled or tripled the market cap in like three to five years, that would be pretty awesome.

Anand:

And then COVID happened. So all the trends that were already the case, they all accelerated because of COVID. And so whether it was digital transformation, remote work, customers not showing up in retail locations. So imagine this: if you take Lululemon, which is one of our biggest customers, or many others, these are all modern brands. They have a really compelling in-store experience. And literally overnight their employees were gone.

Anand:

They were not coming to work anymore. They were remote. And then their customers were not coming to their stores. In fact, their stores are closed. And so it ended up that all these things that we were telling our customers, our customers were now telling us, which is, "Look, cloud is really critical. I got to move to a very flexible platform. I got to support all of these channels because some people are going to use text and some people are going to call and I can't be good at one thing and not good at the other."

Anand:

And so it ended up really being our moment. And even though technically COVID didn't have as much of an impact, we were certainly tagged in the public markets as a COVID stock and ended up sort of becoming a decacorn in like a year and a half, two years, and growing till the Zoom acquisition earlier this year.

Delian:

Yeah. It sounds like a sort of incredible way to come across as sort of the next role, where just so much so fits into a thesis that you have and sort of a skill set of an area that you thought about a lot. I'm curious. You've done a great job of sort of scaling your own skill sets across a variety of different things, whether it's switching to completely different computing platforms, I.e to mobile, to switching even within mobile, from iPhone to Android.

Delian:

I'm curious, as somebody who's maybe listening to this podcast and is just getting started out in the world of technology, and obviously I'm sure over the next two decades will experience so many more platform shifts and even certainly more rapid technological change than we've seen over the past two years, do you have particular, I don't know, frameworks or pieces of advice that you give to people on just like how to stay at the tip of the field and continue to understand sort of where things are headed, as opposed to just being a sort of one shot wonder with one particular sort of flash in the pan and understanding one technological trend versus being able to continue to understand them?

Anand:

Yeah. I think a few things that have worked for me and a couple mistakes that I made is, one, I would say just getting 1% better every day I think is like one of the most underrated things. People sometimes want that I worked out for a week, why am I not looking better mindset. They go all in for a short amount of time, but they sort of underestimate the value of just getting 1% better every day for a very, very long period of time.

Anand:

And that's probably the biggest thing I would say, is that sometimes looking around the corner is just like having that 1% more curiosity when you talk to someone. Asking the same question to a hundred different people, for instance, is totally underrated. So I think it's really the 1% better every day. The other one is there's a book called Mindset by Carol Dweck, which really changed how I think.

Anand:

I think what I had in my twenties would very kindly be described as the fixed mindset. And I wish I had read a book like that sooner in my life just to have like a growth mindset, taking feedback a little bit better, having sort of this you're never done. You're even framing your successes as like part of a big climb or part of a big marathon rather than like you've now "made it."

Anand:

We've all heard the story of how Satya has sort of reinvented Microsoft around the growth mindset, which is probably like the best indication of someone who was dodgy and thought they had "made it" now have reinvented themselves because they can still grow and they can still get better. So that's something I would highly recommend, both the book and that kind of mindset.

Anand:

The other thing that someone told me is if you've got ambition around something, as they say, don't dream in silence. Just talk about your ambition. Talk about what is it that you like to do. And usually if you're thinking about starting a business, for instance, and that's really important to you, oftentimes if you're a good product manager or something, you'll always create offers.

Anand:

So unless you talk about it publicly that you want to start a company someday, sometimes it's the commitment and consistency thing that works out if you publicly commit to something or if you talk about it. So the flip side of that is don't dream about your ambition in silence. And then the other thing I would say, this is a mistake that I made a couple times in my career, is when you realize that something is a rocket ship, don't worry about the title.

Anand:

Sometimes when you are midway in your career and you've held a certain level of seniority, you could think of it as like a damage to your ego to take a title that's like a couple steps down. And when you're really successful and it's like an incredibly defining company off your career, no one will ask you or even care what title you had in that company. And so that's, again, part of the growth mindset. You will eventually get to the title that you deserve if you just start off with the rocket ship and take the role that's important at that time.

Anand:

So those are probably three or four things that I've learned over a period of time. The other thing that I'd say, which is probably like... Again, I've learned that from failure, is you make a lot of your money and your fame through your success, but you probably make your reputation from all your failures. So a lot of times just failing in a dignified way, but looking around you and helping the people who are with you when you're going through a really tough period, that's again very underrated.

Anand:

People think that no one's watching them when they're failing. Because when you're successful, everyone's watching you and it's easy to be on your best behavior and to do all the "right things." But you make a lot of your reputation, at least for me, from the moments where things were not going well and you make great friends and trust and reputation, things like that.

Delian:

Well, Anand, I truly appreciate you taking the time and giving such great advice to folks that have listened to the podcast. It was a really great conversation. Thanks so much for coming on.

Anand:

Yeah. Thanks, Delian. I don't know how you do this man with all the stuff that you've got going on, but thank you so much for having me.

Delian:

Yeah. No problem. It's tough. It's not easy. Thanks to Michelle.

Delian:

Thanks for listening, everyone. If you'd like to support the podcast, please sign up for a paid Substack subscription, which we use to pay for transcripts, mics, and other improvements. If you have any comments or feedback on what kinds of questions I should ask, who should come on the show, or anything else, please do let me know. Have a great rest of your day.