Anand Chandrasekaran (EVP Five9, ex Director at Facebook, ex Chief Product Officer at Snapdeal)

Hey everyone, this is Erik Torenberg and you're listening to Execs by On Deck. Execs is a show for founders, operators, and leaders who want to understand the playbooks, frameworks, and tactics that leading tech companies today have used to scale. Our guests are tech execs in key roles at top tech companies who share their hard-won, earned secrets on how to scale faster.

Anand Chandra Sekaran is a full-time angel and advisor with extensive exec experience at some of the biggest names in tech. Prior to being EVP at Five9, Anand worked at Facebook, Yahoo, and started several of his own companies. In this episode, Anand shares incredible frameworks for product leadership. You can read his thoughts in more detail at Anand C on Twitter, A N A N D C on Twitter. Rishi Tripathi, Group Product Lead at On Deck, joined me in this episode as a guest co-host.

We hope you enjoy.

Anand, you've been at a bunch of amazing companies from Facebook to Yahoo.

to Five9 to starting your own company, you've had a lot of product leadership experience the past couple decades. What does product leadership mean to you? Or what kind of product leader are you? Or what is your framework for even thinking about such a broad question?

I would say it somewhat starts with defining what you want the product leader to be doing well in a company at any point in time. And then the question is, are you at any point in time doing that job well?

What's your style?

to do that. In a sense, I would say other than the CEO, the product leader is probably one of the few other people who think holistically about the company. The big difference obviously is that the entire company likely reports to the CEO in some way, but nobody reports to the product manager. And so I think the big difference is you're essentially getting most of what you're getting done through influence rather than any kind of command and control or any kind of direct reporting ability to influence. I think that's a big part of successful product leaders is that they're able to form these merit-driven arguments for what they'd like to frame or how they'd like to get something done. It's really convincing people to— not to get too Inception-like, but you want to make people— make it look like it was their idea to do something. drive through influence rather than through command and control. From that perspective, a great product leader is usually doing a good job of taste and structure prioritization, bringing some coherence to the whole roadmap. If there's a bunch of priorities, picking the few things that add up to form a thematic, okay, this makes sense kind of thing. Then the one other thing I would say is, A lot of product people sometimes start out trying to win popularity contests. If you're doing product management really well, especially at the leadership level, you're not winning any popularity contests. You're saying no most of the time. When you're saying most of the time, you aren't that popular. Maybe you can be respected because you say no in a very thoughtful way. Done well, this prioritization job is basically everyone's a little bit disappointed, but no one is surprised. About where the company is going.

There's something really interesting there. And I'd love to hear more specifically about how this showed up at Facebook, where you're thinking about a company that's so product-led across the board. In the space that you were at in Facebook, specifically around Messenger and Messenger platform. Platform is this word I think that gets used a lot, but I think a lot of people may not have as much insight, or maybe I'm still learning what that means at different places and how to think about what does it mean to build a platform? What are the trade-offs of those sorts of decisions? Could you share a little bit about what that meant at Facebook? And then as other people listening to this may be building their own companies and their own product teams, what does it mean to make the choice to build a platform?

Yeah. So a couple of context things, right? So one, from a platform definition perspective, you're essentially giving people the building blocks that you might be using internally, and they're building interesting, innovative things. And as Bill Gates famously said, If a platform is successful, the people building on top of the platform are making as much, if not more, money off of the platform than you are. You're building the empowering things that others can use to grow their businesses as much as you are. In the case of Facebook, think of it as Facebook is not a development platform in the very traditional sense. Android is or iPhone iOS is. It's more of a distribution platform. Essentially, the thought there was the same things that Facebook is doing internally to gather distribution, could we give that to third parties as well so that they could acquire this one-to-one communication through Messenger with their customers at scale? Let's take a few examples like Sephora has all these relationships with young girls who go to their store. Can they have a digital one-to-one relationship with the same users, the same consumers through Messenger, right? And if they wanna get an appointment at a store, can that happen digitally before they actually show up at a store, right? And so, I would say the Messenger or any platform story when it's really successful, you basically think it was such an inevitable idea once it's successful. Like today, the idea of purchasing a product on Facebook or Instagram and getting all your customer care messages on Messenger. It's just super normal. And that kind of inevitability, in one annual letter, Jeff Bezos sort of says, the best recognition that an innovator can get is people yawn at your innovation. It's so obvious that people just yawn when they think about it. And to the people that created it, it's actually like a badge of honor is that you made it so obvious that people don't think of it as innovative anymore. It's just default.

That's fascinating. One thing that I'd love adjacent to platform is sort of this concept of companies that are product-led, right? When you were talking about what makes great product leaders, you talked about the things that you're saying yes and no to should be so obvious because you've been communicating it the entire time. In kind of a similar way, companies that are product-led, you think of a lot of the things that Facebook has now pioneered are standard in how we communicate, how we do things in the consumer social space. Facebook is sort of in my head just this example of such a brilliantly led product-led company. What are the threads that either indicate that a company is trending towards being product-led or not, especially through this sort of phase of growth that lots of startups go through? How do you know if you're going to come out the other side successfully?

Yeah.

I mean, look, I actually think that it kind of depends on what space you're in, right? There are a lot of spaces where There is a huge amount of offline product. Your product touches the real world. You can take so many examples of that. You can't wish away the real-world part of your product. But that said, you can convert more of your business challenges into computer science problems. Then every time you can convert a business challenge into a computer science problem, PMs and engineers and designers can kick in. to try to automate away that problem statement. Usually what you want to have is something that ties together the why, what, and the how in the product journey. As important as choosing which problems to solve with product is which problems to not solve with product so that you can take 80% of your resources and focus them on 1 or 2 most important problems that you're going to use technology to solve for your users. I would actually say product-led primarily means that, at least in my mind, that people don't have an offline way to associate with your brand. The digital experience that they have is all they have to evaluate you or your brand. A lot of times if I use an iPhone, I have no idea how the org chart is, that built the iPhone. I just used the experience. There's one interesting law called Conway's Law, which is a lot of times people just ship their org chart. The joke that I would use is that if you go to the Yahoo homepage back in the day, you could tell how the org is structured because there would be little sections for every team. They would want their little sandbox and they'd want the traffic to go from there. What you want is ideally, as I really like how Apple calls it, we bring the hardware, software, services together so you don't see where the line blurs between one and the other. And so, I think product-led is largely that you don't have the offline experience like a set of retail stores or some such thing. In some cases, you don't even have a customer care line. You just have the product, and the product is really your entire brand.

You've been involved with companies at all stages, and I'm curious if you could sort of outline how founders should think about the different stages of product maturity and the different sort of resources that people need, maybe going from the beginning where maybe the CEO or one of the co-founders is leading product and then they scale and they need to hire their first PM. Maybe we could start there and then go from there.

Yeah, I mean, I think at that stage, Erik, I mean, as you know really well, you live or die because, you know, you got product-market fit, right? And so pretty much the only thing you could do wrong in that stage is do what I call playing operator, which is hire a lot of people, raise a lot of funding, and use all these kind of artificial signals to say that you have product market fit, because before your consumers or your business customers are actually paying for your product or spending time and the retention is growing and things like that. So there are some fairly well-documented metrics that indicate that you are trending towards product market fit. And then the other thing I would call out in that stage is there are people who get impatient when they're a little bit close to product market fit, and they don't differentiate the subtle differences between weak product market fit and strong product market fit. So sometimes you might have solved a part of the problem, but you didn't hit the bullseye and solve the most important part of that problem, right? So I would say however long it takes, like, In my experience, like as an angel, I've seen marketplace companies right from the beginning sometimes take 3 years where they are in like 1 city or 2 cities or 3 cities to the point where like if I have a monthly call and can we go 2 years later, 3 years later, sometimes I've had the, hey, like don't you guys have like, you know, that big of an ambition because you're only in like 2 cities, but they're perfecting their marketplace playbook in a very, very small number of cities. And they're even getting to contribution margin positive and milestones like that, in addition to just product-market fit and retention and that part of the playbook. And then when they're able to raise their Series A or Series B, for instance, sometimes even that round ends up being a large growth round because their playbook has been proven out and they can scale pretty rapidly. So I would say at that stage, the other thing I've seen in my experience is You want execution to be close to perfect in the pre-PMF stage, and you don't want people who are very half-heartedly committed to the company and things like that for the following reason, right? You're, you're defining a hypothesis and you're, you're seeing if the hypothesis works in the real world. And if it works really strongly, then you have product-market fit, right? Or you're trending towards product-market fit. What you don't want is this weird situation where something didn't work as a hypothesis And you don't know if it was because of sloppy execution, because your team wasn't all in, or the hypothesis didn't work, right? Because you want to rapidly abandon a hypothesis and move to the next thing. And you don't want this like, you know, sinking feeling in your stomach if like the hypothesis was actually true, but you didn't execute it perfectly, right? So in that pre-PMF stage, one of the non-obvious things is that you want a small team of like really committed people who are just like, you know, executing almost perfectly.

And so I want to sort of extend this story out into the future a little bit. If we press fast forward, you've hired a few product people. Now you have a little bit of an org, let's say maybe 2 to 4 people. And we can talk about hiring. That's a whole other topic we can dive into. But you now have a product org that's being built in this larger and increasingly complex organization, right? At that stage, how would you encourage both that product team and also founders and execs How do you figure out the signal and the noise? And what are the signs of a product team that's communicating effectively just in order to get stuff done and make sure that stakeholders are engaged, et cetera? Let's talk about this maybe at the mid-stage where you have a small but growing product team.

Yeah. So actually, that's a great segue from the product-market fit topic, which is if you have stayed super disciplined and you have strong product-market fit, that actually really helps you transition well into the next phase because whether it's B2B or B2C, let's take the B2B case for example. If all your customers have largely asked for the same set of features from you, as opposed to there are islands of customers who've asked for different sets of combinations of features, it makes the product team's job a little easier because there's one set of priorities that all the customers are clamoring for. And you have already exerted the discipline that has led to the sequencing and the prioritization becoming clear. And in the B2B case, you've got salespeople who are bringing this probably to the customer base as the company grows. Initially, there was probably purely product-led growth, or the founders were doing a lot of the sales, things like that. Now, as the product org has grown, you also have the sales org growing in B2B. And so what you want is sort of one set of customers asking for one set of capabilities to solve one set of problems, right? So if you've done the discipline during the strong PMF stage, then that really helps out in the next stage. If you have weak PMF, that's where that manifests for you, is that in the next stage, you've got a bunch of confused and disconnected teams where one set of sales teams is clamoring for one set of features, and one other sales team is clamoring for a second set of features. the product management job becomes a little bit kind of herding cats. And also you are disappointing your customers who may have paid you some revenue in the early stage where you thought you had product market fit, right? The same actually holds true in the consumer realm as well. It's probably a little bit less dramatic because there aren't salespeople yelling at you all the time. Consumers are just choosing to use your product less because you're not developing the same set of features that the initial cohort of customers who are sort of strong users, who, as Paul Graham or others would say, it's better to have a few people that love your product than, you know, a lot of people who like your product. And so I think you owe it to yourself to really stay in the strong PMF stage because it'll really solve a lot of the kind of people you hire and things like that later on. I would also say most of the communication, at least in my experience, I've had the cadence of team strategy operations. So like most of my updates are, there's updates on the team side, there's updates on the strategy side, there's updates on the operations side. So in the team side, you know, you're largely talking about who the new team members are who've joined, what their skill sets are, which companies they're coming from, what problem set they're here to solve for us as a company. And also you're communicating what, if anything, has changed in terms of reassignment of engineers or assignment of engineers period to begin with and so on. On the strategy side, that's where you're largely updating people on any changing priorities with respect to prioritization, because if the strategy of the company has changed, you don't want the product and engineering strategy to not reflect the broader changes in the company level. This is also where, as you raise more capital, you can walk and chew gum at the same time. Sometimes when you don't have a lot of capital, you have to force prioritize and sequence out, whereas sometimes you can raise capital to say, look, we're growing a new product in the US and we don't have full proof that that works, but we're also expanding a product that we know works in one market to 10 other markets. And for that, you can raise capital. It's a pretty deterministic thing. And actually, that's a big distinction I've seen in product management skill sets as well. So you've got the people who do 0 to 1 product, discipline-wise, they usually come from engineering backgrounds or deep technical backgrounds or design backgrounds. They usually like to make things constantly, and they have no patience for the optics or the politics or the herding cats and the program management and all of that stuff. Then you've got the 1-to-N people who like the large teams, who like the weekly cadence, who keep everybody in the loop. You'd be naive as you grow to say that one skill set is important and the other is not, right? It's a balancing of those 2. And largely you want the 0 to 1 people to be doing the newer capabilities and newer products that are unproven, but you're constantly iterating. And those people are very comfortable being in a windowless room for like 6 weeks, like just iterating on mocks and code and stuff like that, are usually incredibly hands-on. And then you want the people who are set up with revenue goals and scaling goals and things like that, who really are in some sense, like finding ways for the company to pay the bills to do the innovative stuff, right? So the two actually really coexist with each other, and good product leadership is largely like trying to see where the bets are in the scheme of things. And if done well, some companies use the 70-20-10 approach or any number of such approaches where you've got a constant number of irons in the fire, but you also don't have 70%, 80% of the resources doing unproven things, right? You have 70-80% of resources finding ways to pay the bills so that you're reducing your dependency on new capital and fundraising.

Yeah, that makes a lot of sense. Thanks for that overview. Let's talk a bit about the personnel in terms of both on the early product team, what maybe what kind of risks you're comfortable taking or not comfortable taking, or what to look for in those early hires. And then in terms of really bringing in more seasoned gray hairs, so to speak, or seasoned leadership, what to look for in, say, a VP of product and when you know you need to bring one in?

Yeah. So, Erik, on early stage, I would say one sort of recurring general principle that works is to have generalists, much like many other departments, and to have folks who come in with a deep understanding and appreciation of the problem statement and the value and the mission that they're a part of, and really be willing to take multiple approaches to solve the problem, particularly when there isn't product-market fit yet. One sort of common mistake I've seen is people who come with one set of expertise, they have that approach to solve the problem and their loyalty is more to the solution rather than to the problem. What you want is someone who's willing to abandon one approach to find other approaches to solve the problem. One thing I like that On Deck does is sort of before deploying a lot of engineers, you have a no-code approach sometimes to solve the problem, which is, I think, you know, a great example of using the tools that are available at any point in time, as opposed to coming in with one approach to solve the problem and sometimes taking 3 months more, 6 months more to solve the same problem that could be solved in a week by just taking a different approach, right? So in the early stage, I would say that's probably a key operating principle, is that there's a lot of value to mission alignment rather than to expertise. I think at some point you're going to realize, here are some DNAs that are important to the company. For instance, there are going to be product development cycles which are governed by high regulation where you don't want to be moving fast and breaking things, as they say. You want there to be compliance. You want there to be the checks and balances. You want the process to be there. If you're storing credit card information or payment cycles or products for investors and so on. That part of the product development cycle is probably way better off run by someone who has a deep understanding intuitively of those kinds of things. It's hard to learn that on the job. Sometimes the various, especially globally, what regulatory systems you need to be compliant with and so on. But over a period of time, I think you also get a sense of what the instincts are. What you want is, in some sense, who's the person in-house that has that instinct, that product instinct within the company? If you are doing a lot of people search, people-oriented products, you probably want someone who's built a social product from the ground up. For instance, social plus knowledge graph type products. It's really a question of having the instincts, whether the founder has it or the product leader has it or an individual tactical PM has it as the And continuing on the start of talent, there's one thing, just like with companies and technologies, you think about build versus buy.

There's also the same thing with talent. Do you do homegrown talent? Do you hire people junior, grow them over time? I know Google does the APM program. Yahoo also did theirs. Facebook does RPM. So one thing we've been playing around with internally is should On Deck do something, some generalist rotational program? So that's one class. Homegrown versus hiring in senior talent. And then adjacent to that, how do you know that a product manager is ready for more leadership? And what does that look like over time to promote or to have that homegrown talent grow over time?

So Rishi, on the APM part, I can take that first. I was actually at Yahoo and worked with Marissa while she introduced the APM program that she had co-created and led at Google. I think that's a great idea actually to pick unproven talent and give them large problems. One thing I've found that really works with that program is folks who are coming in largely don't have the level of industry experience. And while there are some obvious things that could go wrong with that, the big pro— the big positive is that they just don't know what they don't know. And sometimes they just solve a problem that no one told them couldn't be solved, right? So in terms of counterintuitive approaches, And just sort of people, you know, work just breaking through walls, getting to the other side and so on. It's actually a great way to find and nurture unproven talent. I also think that's a great way to build, you know, product leadership within the company who start young and, you know, take increasingly large sets of responsibilities and grow from there. I'm also a big fan in generally promoting from within, you know, largely because it takes a little while for folks to understand both what's required to win in a space, as well as the mission of a company and the approach to winning. And so, you know, folks who demonstrate that internally are in a really great place to grow just within the company. So I'm a huge fan of that, particularly with acqui-hiring. I think it's great to have almost like a hit list of folks that would be fantastic to have in the company. And You know, there's always folks that it's bad timing because they have another job or they have a startup or something like that. And if there's an opportunity to bring one of those people that's always been on your top sort of list of people to recruit for a very long time by actually, you know, acquihiring a company that they were part of, then that works probably the best in terms of an acquihire strategy or to bring a small group of people, particularly folks who've worked really closely together for a really long time. That often sort of minimizes the need to create chemistry between them. Because they've been already shipping products together for a long time, potentially.

Yeah, that's fascinating. This concept of like the dream hires is one that we definitely buy into at On Deck. We talk about, oh, I'd love to work with this person, that person. And sometimes you kind of, you hit the lottery and you are able to land like great talent. The second part of the question I think is one that I'd love to hear more about around how do you know, given a specific junior to mid-level Product person, what are the signs that that person is growing, that they're developing sort of the leadership muscle in order to make that investment in that talent worth it over the long run? And especially at scale, if you're able to systematize it in something like an APM program or even outside of product, just generally investing in talent.

2 things, right? One is, you know, so mostly, you know, I think of people's delivery on their job through the lens of talent and motivation. you know, do they have the talent, you know, the basic skills to do this job? And the best indication of this is that they are overdelivering on their current job, right? I think there's a— there's sort of a longstanding argument on potential versus results, and it's very hard to talk about potential in the absence of results, right? So I think the best indication is that they are doing really well against their current goals and constantly demonstrating, you know, a little bit of ability to look around the corner compared to what their current job demands. Talent and motivation are the obvious things to look for, but also sometimes what ends up happening is that they end up doing so well on their current job that they actually create the opportunity that leads to their next job. A friend of mine that I know really well was the first product manager on Android. And when Android started growing, literally this person's job responsibilities just started growing because they created the opportunity for themselves, for their job to grow. And so when Android became a global product, they ended up becoming global team. When Android started to have various integrations into the rest of Google, that became a big part of the product. When there was a hardware plus software component, that got added to the Android product lead's portfolio. And so I think in a way, The most successful PMs I've seen are the ones that take their own destiny in their own hands. And there's a little bit of luck involved in it, but they almost manifest the product organization that creates their next job and their next job and the one after that and so on.

Yeah, growth is everything, I think, in these sorts of roles and also in creating the opportunities that are around the corner from the current one. You talk about measuring roles and measuring people's growth through the lenses of talent and of motivation. How at different stages of companies have you seen teams measure their own output in aggregate? How do you measure product teams? In a product-led company where the only thing is the product, it's fairly clear. Is the product growing? Is everything going healthy? But maybe for companies that are either working towards that or where the company goal may not be as clear. How do you measure product teams and evaluate them? If maybe it's different at different stages, but curious to hear your thoughts.

Yeah, so, uh, you know, probably the best book, uh, that, that talks about, you know, how to evaluate leaders and how to evaluate people who are increasingly growing in their potential is High Output Management. You know, one of the things that is super interesting is as you become a leader, the right way to evaluate your success is actually not how well you're doing, but how well other people are doing under your leadership. Because you're responsible for the circle of influence that you're directly involved in, as well as the circle of influence of all the people that kind of report into you, who are part of your organization. One of the things that, for instance, sounds super tactical is that I think some of the most successful product execs and execs in general, operating execs, tend to be super responsive. Why is that super important? Because as your scope and team size expands, you can often become the bottleneck. in decision-making. The faster you can unblock things, the faster you can be a human router, the faster you can come up with an opinion on a couple of options that directly involves you, the more you can have other people move faster. I think the important thing is that folks who are great individual contributors but not empowering other people to succeed, and not creating a clear sense for what the North Star metric is, that their part of the product or their product, which is part of the portfolio, is seen as winning. We talked earlier about the zero-to-one versus one-to-N. Managing those 2 styles of product managers, for example, is also significantly different. Also hiring those 2 instincts and putting them in the right part of the portfolio, those kinds of things tend to be very important as well. In addition to hiring great talent in general, that usually ties with motivation as well. So sometimes what happens is you have a person who did 0 to 1 for a while, but then becomes curious to do 1 to N. And so recognizing those changes in people's desire and their own desire to go try something new is also important to retain people over the long term.

Definitely. There's a lot there. I think especially some of it hits home especially hard for On Deck right now because Our team is growing rapidly, we're looking to hire, we're seeing if there's people who are going to transfer or change roles and how those roles might change over time. So really insightful to hear some of this background and your experiences here.

Well, one of the things that again is a common thing that you make this mistake when you're young and then you recognize it as you do it repeatedly is when you know that something isn't working out, whether it's a new hire or someone you moved into a new role, et cetera, one of the things that folks do in a startup is they just give it more time. And then they just say, hey, you know, I don't have enough data. I'm going to give it a quarter more or a month more. I've found, at least in my experience, almost 99% of the time I don't get any new data and I've just delayed the decision by a month or a quarter. So I think like sometimes just shooting for this, what Keith Rabois calls 70% conviction on decision-making, right? Especially when you need to make hard decisions. And sometimes the delay that you cause in your organization by just waiting for 90% conviction, you know, especially when things aren't working out, you're never going to get perfect information. Like most decisions in a startup, you've got to make it with the information that you have. And so some of those hard decisions, you've got to make it based on incomplete information. But the important thing is that you make those decisions and move on, especially the the unpopular ones like letting people go.

Yeah, totally. Anand, you're dropping a lot of knowledge bombs here and really insightful frameworks. What do you think are non-obvious mistakes that you see founders making even though they might understand these frameworks intuitively or they might not? But what are things to watch out for that you're advising your founders as they're scaling their product organizations?

Yeah, I think, Erik, going back to our conversation, One of the most important things is that you're demonstrating a sense for what is important at that stage. You know, we talked about the most egregious example of that, which is folks pretending that they have product-market fit before they do, kind of doing the things that you would do in the next stage, assuming you had product-market fit, but when you don't, right? So that's probably one of the most egregious ones. Once you do have product-market fit, it's again this stage-focused demonstration of who you bring in, what the product priorities are, how you communicate that across the organization, how you encourage constructive criticism and debate of the roadmap and the priorities that have been picked up by the product leadership and the company. That's one area where there's a set of mistakes just around stage-focused decision-making. The other thing I would do is actually just kind of as the company grows, becoming too tactical and focusing on just the execution of the current roadmap and so on, rather than how the vision and the mission of the company can be unpacked, bringing the broader ambition into the product team. People can become very goal-focused and sometimes you can just be too focused on the trees for the forest, as they say. I think great founders know when to separate from that, And whether it's building new teams or increasing the ambition of the existing team, try to manifest more of the vision within product and so on. And we talked about product-led companies. In those cases, it's important that the priorities be redefined. And what happened with Messenger is a great example. Messenger was purely used only between people, person and person, P2P messaging as we called it. And with platform, There was now P2B messaging, person to business, where it was now possible for the billion plus users to communicate with the 60-70 million pages owned by businesses. So that's actually a huge example of manifesting your broader vision, even though the existing product is doing pretty well. You've got over a billion users, so obviously things are going great, but you're actually driving the broader ambition that you want manifested by the product team.

I really like that. You have experience sort of as a founder, in addition to all the operating roles that we've been talking about. What is it from each of the experiences and roles that you bring to the other? What are the parts of the founder journey that have helped you to be a product leader in other organizations? And what are the parts of the structure or the execution at places like Facebook, Yahoo, et cetera, that then translate into the founding experience in that journey?

Yeah, that's a great question. I would sort of caveat everything that I'm saying by sort of just saying that as an entrepreneur, I would probably give myself a 5 out of 10. I've met so many incredible entrepreneurs, including Erik, you, and so many others that I've been lucky to be part of the journey of. I would sort of say my views on scaling product and being an operator are probably far more relevant than my— maybe I can tell you the 25 things not to do as a founder, which would be more valuable. But I would say, I think the thing that's helped me the most as a founder, when I think of my operating role, is to sort of look around the corner. One of the things that founders do is they constantly think about how the world can be better because of what they're building. And they have one foot in the current universe and one foot in this future universe that they're building. And they, you know, when they're operating at the top of their game, they're able to figure out what needs to change in the present, but also what parts from the future they're going to bring into the present at the right time and in the right sequence, right? When you have been a founder before, you're able to put that mindset on yourself without constantly being dependent on the founders of any company that you're a part of. and sort of ask yourself how you can look around the corner, how you can look at that mission, that future manifestation of that mission, and what can you bring into the delivery today? What can you prioritize today? What is adjacent to what you're already building? I've seen this done really well in a lot of B2B companies where it's sort of in the industry, it's called TAM expansion, where there's a total addressable market that the company goes after today, but by building these constantly increasing incremental things. Atlassian is a great example of this, where they started out building a tactical product, but now they own so many large pieces of the developer cycle. It was constantly iterating, constantly building new capabilities, constantly building new products that are adjacent to existing products, make sure they work really well together. I think being a founder can really help you wear that hat internally of how would a founder think and how would they manifest that future and the trade-off of living in the present versus, you know, one foot in the future. I think that mindset is probably the biggest thing that being a founder helps you bring as an operator.

Totally. I want to segue into your investing practice and frameworks and learnings there. But before that, are there any core insights in product of yours that we haven't yet been able to You've given a lot of frameworks already, but just wanted to make sure we—

Yeah, I think one thing I would say, Erik, is there's a lot of product managers as well as founders who are going back and forth between B2C and B2B. Going back even 10 years, I think someone who started their career in B2C pretty much ended their career in B2C, and same of B2B founders and B2B product managers. I think lots of folks are making the switch back and forth. And I think there's some really interesting trends that are driving that. And I think more folks should lean in on their intuitions in B2C to develop B2B products and vice versa. Right. A lot of examples of this, right? Erik, you and I are both in Dive. If you take Dive or Slack or Zoom, the reason they're growing really fast in a very short period of time is because they're bringing a lot of B2C instincts to B2B products, or at least categories that were perceived as business-to-business products traditionally, right? And, you know, while they're building for this business persona, they're bringing great UI, they're building the kind of products that we would all build for our family and friends, especially if you can't go into the office and everything is remotely done, you know, it's remote first. And then the other side too is blurring quite a bit, right? If you take a lot of marketplace companies, consumer marketplace companies today, a lot of the supply chain aspects, a lot of the seller-focused product look and feel like B2B products, right? So I think product people, product leaders are bringing a lot of the insights from one into the other. And I think, you know, for the next 10 years or so, we'll see a lot more of that cross-pollination. Between B2B and B2C. And one of the things I think will happen more, you know, we're seeing that with Dive, for instance, is consumer-like network effects are showing up in a B2B product, right? So in the past, there aren't a lot of B2B products that have network effects, but now there are easily, you know, a few you can name that are at scale, which leverage network effects in B2B. Slack and, you know, Confluence and Jira are all great examples. where network effects are being leveraged inside of businesses. So, that's, I think, a big part, you know, and I've been very lucky to straddle the B2C side with, you know, Facebook and Snapdeal and Yahoo and so on, and B2B with, you know, Five9 and, you know, being an investor in a bunch of angel investing in a bunch of companies that have broken out in B2B as well.

Anand, you've basically done my segue for me, so I appreciate you for that. I was gonna— so, kind of moving into the talking about the investing side of things, You've talked a lot about how these trends are showing up across industries and how your product mind helps you to make those decisions. You've been pretty prolific with investing over the past couple of years and you've been sharing progress very publicly and transparently on Twitter. What is it about that experience, either whether you think it makes you a better product leader or if it's just fun to support founders throughout this process, why do you do it? And what are you excited about as you continue that practice?

So 2 reasons, I think, as I look back. One, I would say, when I was at Stanford and did AeroPrize, it was less than a year after I had moved from India to go to Stanford. And I was just very lucky to get the help from people in probably ways that I didn't even deserve, right? So the example that comes to mind most often for me is a Stanford professor called Rajeev Motwani. who's no longer with us but was a very, very well-known mentor investor back in the day. He was an angel in Google, for instance, and many other successful companies. So he would sort of spend a lot of time helping technical founders figure out a lot of non-technical topics like fundraising and hiring and building, you know, sales and other departments and so on. I remember chatting with him and going, why don't we officially make you an advisor and give you some equity to make it worth You spending all your time. You know, his response was, "Well, let's just focus on helping you now, and we'll figure out the transaction later." Right? And this is, of course, like you know, this idea is not new to anyone in On Deck, which is a spirit of generosity. And I think it's it's it's a bit of a lost thing today, where everything has become so transactional, both on the founder side and the investor side. And this almost feels like a blast from the past, where to have the spirit of generosity and more than a transaction. And sometimes, you know, build a founder relationship over a 10, 20-year period where you actually benefit monetarily, you know, way late in the long relationship that you have. And so for me, it's actually doing to other founders what a lot of people did to me, and in no small part influenced my, you know, the big steps that I went through in my career. I think the other piece is honestly, It's very hard for you to be in the trenches on several different industries, and being in cap tables and getting the investor updates, for instance, is a great way to actually stay in the trenches and keep your ear close to the ground. And so when I started investing, you know, it was actually to be a better operator. You know, I felt like it would help me hire people better. It would, you know, force me to be hungrier because I would understand, you know, how founders with far less capital than I did in my operating role how they were hiring, how they were closing candidates, how they were sort of convincing someone from a larger company to join, and so on. And that's largely, you know, I've been like more than grateful to get, you know, quite a bit of learning because of that. Even sometimes when the startup fails, right? Obviously when a bunch of them break out and succeed, that's sort of the icing on the cake. But, you know, even when the startup isn't successful, you learn a lot. And, you know, one thing that someone told me, which I look back often, is that, you know, you actually make a lot of money from your successes, But you make your reputation from your failures, right? So, uh, when someone is failing, uh, there are very few investors, there are very few friends, uh, who are actually with them, uh, and I try to go out of my way to make sure they're okay, their mental health is, uh, in a good place, are they able to land on their feet, uh, and, you know, sort of again going back to building a 20-year relationship with these founders, try to make sure they, uh, start their next chapter well.

Totally playing the long game for sure. And yeah, we're lucky to be the beneficiaries of that. You know, something that's really interesting is that you've Obviously you've been at Facebook. Facebook did the family of apps really well. Of course, they rebranded to Meta recently. Similarly, but obviously at a very different scale, On Deck itself has different offerings to different customers, founders and also tech employees and also investors. Obviously that's a much bigger topic, but what is some high-level framing of maybe what you learned from the Facebook experience or elsewhere that you think might apply to On Deck that is trying to have a cohesive brand while also having different products that appeal to, to, you know, all tech people ultimately, but slightly different customers?

Yeah, absolutely. Um, you know, so I think the, the one nuance I would say is that whenever you see a family of products, right, whether it's, uh, within Google/Alphabet or Facebook/Meta, uh, there's always a flywheel, right? Uh, uh, and, and one of the things that is probably, um, underestimated is how much products like Messenger and Instagram benefit from the Facebook graph. The reason Messenger has so much value on day one when you download the app is because the entire Facebook graph is on your Messenger app. You don't have to invite anyone, they're all right there, and you can start messaging without knowing their phone number. I would say the only app that probably built a social network from scratch and didn't have a lot of dependency on Facebook for the initial graph and the growth is WhatsApp, because WhatsApp leveraged the phone number graph as opposed to the Facebook graph, the social graph. The big insight there is that you do want a central flywheel that's feeding off the new businesses, and that's there with the non-dec in spades, because the talent that's joining the on-dec CBCs Uh, they, you know, form the basis for ODX and, uh, so much else that On Deck is doing, uh, now and in the future. Uh, and so I think the, the key is that, you know, you don't forget like what, what got you there in terms of the initial flywheel, and you keep feeding, uh, and keeping that flywheel, you know, extremely healthy, right? Um, so that's, I think, the biggest insight there in terms of even though there are a family of apps, uh, they're all related by the core flywheel that gets the, the company growing in terms of low-cost acquisition of either supply or demand, right, within, within the, the family. I would say other than that, uh, you know, uh, the fundamentals are still the same. Like, you still have the team strategy ops focus in each of the, each of the products. Um, I think one thing that I've seen is that when the company is growing really fast, right, like, uh, let's say you have one of these unfair advantages, and as a result, the second or third business that you're building is growing rapidly and is scaling really fast. The way I think about that is that it's a few things, right? One is it could either accelerate the current opportunity. In other words, like what you were looking to achieve in 2 or 3 years, you could achieve in 6 to 12 months. So it's an acceleration of the current opportunity. But what it could also do is present new opportunities way faster than you thought, right? So a great example of this is the Facebook Graph growth presenting the opportunity for people to communicate through an app like Messenger, which didn't exist when the original flywheel wasn't growing as fast. That's the second thing that really fast growth presents, which is it raises new opportunities that are uncovered because of the initial flywheel. Then the third is that your learning cycles and the insight cycles are accelerating as well. If done right, then you're developing a monopoly on insights and monopoly on learning that your competition or other folks going after after the same consumer or business is not able to get because they're not quite growing as fast, right? So those are in some sense very, very leverageable moats that companies could build to grow faster with the current opportunity, to create new opportunities, and to learn and have insights way quicker and way more leverageable than anyone else in the industry.

I want to be mindful of time. I think that's a great note to wrap on, Anand. We're very lucky to have your your advice and investment, be an investor at On Deck. And then of course, very lucky to have co-invested in a number of great deals with you. Anand, thanks so much for your support and for dropping a lot of insightful frameworks here today.

Yeah, thank you so much, Erik, Rishi. Really, really glad to have this conversation. Thank you.

Thanks for listening to today's episode. Execs is produced by On Deck, where top talent goes to start companies, find their next roles, or invest in their careers. If you're looking to start a company, uplevel your career, or navigate a career transition, I encourage you to visit beyonddeck.com.

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