155. Rahul Vohra (Superhuman) shares his Playbook for finding Product-market fit, Fundraising lessons from $125M raised & Why taking on incumbents is a great startup strategy

And I would ask thank you so much for signing up for Superhuman. I have two quick questions. Number one, what do you use for email today? And number two, what do you hate about it? I like to classify product projects as either market widening or solution deepening. Market widening makes your product available to more people, but it doesn't make the product better for the people who already have it. Whereas solution deepening makes your products better for the people who already have it, but it doesn't make it available to more people. The authors Gabrielle Weinberg and Justin Mez have a great rule for this spend about half your resources on solution deepening and half your resources on market widening. I think email and for that matter, our entire digital world is heading to what we call an agentic future. In the so called agentic future, we'll all have AI agents. In fact, we'll probably each have multiple AI agents. The actual structure doesn't matter. What matters is that you're telling a big billion dollar story and that it's rooted in things that make you believable. Entering a market dominated by incumbents is really great for lots of reasons. It's one of the best possible startup strategies. I'll give you four reasons.

Hello friends. Welcome to another episode of Pursuit of Scrappiness Podcast. Whether you're building a business, running a team, or just starting out in your career, we're here to bring you scrappy and actionable insights to help you become more productive. My name is Yanis Epso as always, and I'm here with my co host, Mr. Oldest Hour Accounts.

Hey hi sir.

Before we dive into today's episode, quick reminder. Follow us on Spotify and Apple Podcasts Helps more than you know. In exchange for that, you'll find over 150 episodes there covering all sorts of topics. You need to become scrappier and better version of yourself in life and business. So plenty to explore. If it's your first episode, scroll back the feed and you'll be the first one to know. Every Tuesday when we come out Spotify Apple Podcasts, click that follow button right. If you are following us, you will have noticed one thing we like to ask our guests about their productivity habits at the end of the to many of our guests we have asked that and you know, we sometimes ask about their daily routines or some things they Wish they knew 10 years earlier and sometimes just about the tools they use. What makes your day faster, more efficient? Interestingly, one tool that came up in multiple episodes is a tool called Superhuman that helps to manage users emails faster. I know a lot of you are familiar with the tool. For those who are not maybe familiar, it's a startup that offers well world's fastest email experience as they state. It's been backed by over 125 million in venture capital from investors such as Dropbox founders JSON Calcanis, Ashton Kutcher, Will Smith, Tiger Global and many more. And we're very happy today to have CEO and founder of Superhuman, Rahul Vohra here with us.

Hey. Hello. Hello. Thank you for having me.

Awesome. And just a few words. Rahul is an experienced entrepreneur. He has sold his first startup actually to LinkedIn over a decade ago and then he started Superhuman which has grown into quite well known and well established and well liked product as we found out in email and productivity space. Growing very fast, adding a lot of cool features. Rahul is also angel investor, frequently appearing in also a lot of media publications such as Forbes, Fortune and you might have heard him on quite a few podcasts that I know our listeners also listen to like acquired this week in Startups or My first million. Our goal today is to dive into product market fit. This is a subject Raoul has contributed a lot and published a lot of resources in it. I will leave links in description as well and then we'll cover also some of the fundraising lessons from Raoul's experiences both as an entrepreneur as he raised for example 125 million for his latest startup, but he's also active angel investor so knows both sides of the table and you know, maybe some advice for other, other founders there. So yeah, with that being said, I think let's, let's dive in and we'll start with like I mentioned, product market fit. So for example, in cases of when there's totally lack of product market fit, founders clearly will see that something's wrong, right? And then if there's a great fit and everybody's buying your product, it's flying off the shelves. Also you probably know you're on the right track and I was interested in just starting discussion and thinking like there's a large space in the middle probably when you know you're getting some traction and month on month growth is there, does it mean that you have achieved the product market fit? If you just see good growth numbers.

Having some traction and growing month over month is great. But I think we know that those things alone don't mean you have products market fit. We have to zoom out and ask ourselves what is products market fit? Well, I think we all also know that product market fit is the number one reason why startups succeed and the lack of products market fit is the number one reason why startups fail. And I think it's helpful to turn to what some of the luminaries, founding figures, if you will, in our industry have said about it. So Paul Graham, the founder of Y Combinator, would say it's when you made something that people want. Sam Altman would say it's when users spontaneously tell other people to use your product. But I think it's Marc Andreessen who has the most vivid definition. He would say you can always feel it when product market fit is not happening. Customers aren't quite getting value, users aren't growing that fast, word of mouth isn't spreading, the press reviews are kind of blah, and the sales cycle is too damn long. But you can always feel it when products market fit is happening. Customers buying as fast as you can, add servers, you're hiring sales and support as fast as you can, reporters are calling you about your hot new thing, investors are staking out your house, and money is piling up in your checking account. And this is indeed a vivid definition and one that I was staring at through tears in the summer of 2017 because it seems so subjective, so unactionable. What do you do if by this definition, you don't have products market fit? Indeed. Can you measure products market fit? Because if you can, then maybe you can optimize it, maybe you can systematically, even numerically, increase products market fit. And as it turns out, the answer is yes, you can measure products market fit and you can optimize it in.

Order to even get there. I would say probably, you know, you could walk us through the process you have, but I would assume one thing is like, you need to go through a lot of iterations, for example, and there's also a lot of things that you need to learn and failing to learn would mean that you're not making progress. So maybe to start with that. So, for example, if you're doing this iterations and testing, what have you observed, what helps you to retain learnings and you know, not to do the just empty cycles, but actually make progress with every cycle in terms of, you know, how to structure the team, what to tell the team, what to pay attention to?

Gosh, well, that's a very human journey. How do you make sure that you're iterating whilst you're learning, whilst you're structuring the team? And for folks who want the full process, which we probably don't have time to get into, it's available online. If you Search on the web. If you Google for Superhuman products market fit engine, there's actually an algorithmic process that I describe that will get you to product market fit, with also tips on how to structure your team. But there's a human journey behind this that I think everyone would find interesting. And this isn't really written in the article. This is the process by which we got to the products market fit engine, and we need to understand where Superhuman came from. So all the way back in 2010, as you noted at the top of the episode, I started a company, and it was called Rapportive. We built the first Gmail plugin to scale to millions of users. When people emailed you, we showed you what they look like, where they work, their recent tweets, links to their social profiles, and we grew rapidly. And two years later, we were acquired by LinkedIn. Now, during those four years, I developed a very intimate view of email. I could see Gmail getting worse every single year, becoming more cluttered, using more memory, consuming more cpu, slowing down, your machine, still not working properly offline. And on top of this, people were installing plugins like ours reported. But you'll remember Boomerang and Mixmax and yesware, and you name it, people had these things. And each plugin took those problems of clutter, memory, CPU performance offline and made all of them dramatically worse. So we decided it was time for change. We imagined an email experience that is blazingly fast, where searches are instant, where every interaction is 100 milliseconds or less. An experience where you could do everything from your keyboard, I should say, so you could fly through your inbox. An experience triaged by AI so you could respond faster to what matters most. An experience that helps you follow up on time every time you would never drop the ball again. An experience that just worked offline so you could be productive anywhere. An experience that had all the features of the best Gmail plugins but built in natively. And an email experience that was subtle, minimal, and visually gorgeous. So with that, we built Superhuman. And today, as you said, Superhuman is the fastest email experience ever made. Our customers are getting to their inbox twice as fast as before. They're replying to important emails 8 to 13 hours sooner, and they're saving four hours or more, more every single week. Many of them actually see Inbox zero for the first time in years. That was the beginning, and that's where we are today. And there's a very messy middle. So let's go back to the summer of 2015, because we started much like any other software company by writing code. And in the summer of 2016, we were still coding. And in the summer of 2017, we were still coding. I felt this incredible intense pressure to launch, both from the team and also from within myself. After all, my last company reported had launched, scaled and been acquired in less time. And yet here we were two years in and we still had not launched. But deep down inside, I knew no matter how intensely I felt this pressure, a launch would go very badly. I didn't believe we had products market fit. And although I knew it, I couldn't just say that to the team, because these are super ambitious, hyper intelligent engineers. They poured their hearts and souls into the product. I needed a plan. And so in 2017, two years in, I started my search for the holy grail. For a way to define products market fit, for a metric to measure products market fit, and for a methodology to systematically increase products market fit. I searched high and low, I read everything I could find, I spoke with all the experts and I came across this guy, Sean Ellis, and you might know the name. Sean ran growth in the early days at Dropbox, LogMeIn and Eventsprint. He coins the term growth hacker and he found a leading indicator of products market fits, one that is benchmarked and predictive. So you just ask your users, how would you feel if you could no longer use the product and measure the percent? That answer very disappointed. You give them three not disappointed, somewhat and very. And after benchmarking hundreds of startups, dawn found that the companies that struggled to grow almost always got less than 40% very disappointed. Whereas the companies that grew most easily almost always got more than 40% very disappointed. In other words, if more than 40% of your users were would be very disappointed without your product, you have initial products market fit. And this metric is more objective than a feeling. It predicts success better than net promoter score. It's not only the best way to measure products market fit, you can actually use it to develop your very own products market fit engine. And it's with that engine that you now have a methodology for systematically increasing the metric. And the engine actually even automatically generates your roadmap for you. A roadmap that is guaranteed to increase product market fit.

You mentioned that you spent several years before launching feeling that you don't have product market fit. And the method that you describe is very user centric and feedback kind of centric. So is there a way how you can also work towards that product market fit while you haven't launched yet? Besides, whatever feelings you have in your head and in your heart?

Oh, absolutely. But let's not kid ourselves. It really does start with the feelings in our head and in our heart. In those first two years, it began with a vision, and that vision began with a hunch. And that hunch came from my experience being a CEO, running Rapportive and being what I call a prosumer, a professional who isn't quite a power user. But work is extremely important to me. Email is extremely important to me. And I was doing it for many hours every single day. And I realized during that time at Rapportive and that time at LinkedIn, looking at Gmail, that it wasn't just me, that millions of other professionals were installing these plugins and having the same issues, those issues that I just outlined. Now, you can validate the idea in those early years before you're running the products market fit engine. And of course I did. In that first year, in fact, I interviewed well over 700 people. And if you do the math, that's more than twice a day. And you might be thinking, well, that's crazy. How do you do that? Well, we had a landing page and we had means of driving people to that landing page, which I can circle back to if you're interested in. But the landing page was very simple. It was perhaps 100 words of pitch about Superhuman, the fastest email experience in the world. You'll feel like you have superpowers and a box where people could leave their email and sign up. And when they signed up, they would get an email from me. Now, this was automated, but there was no HTML. It didn't have images or colors or fancy graphics. It really did look like an email from me. And I would ask or I would say, thank you so much for signing up for Superhuman. We're building the best possible products for you that we can imagine. I have two quick questions. Number one, what do you use for email today? And number two, what do you hate about it? And that's it. People would answer in, almost invariably, I use Gmail. Some people would use third party email clients, but typically our early signups were all Gmail. And they would say things like, I hate how long I spend in it, I hate how slow it is, I hate how I have to install all these plugins on top. I hate how it doesn't work properly offline. But the key things were, I hate how long I spend in it, and I hate how slow it is. Because we were early adopters, those users were leaning a little bit more towards speed. Most consumers wouldn't tell you that Gmail is slow, but many of our early adopters were also products people and they realized that if you could make the thing faster, if you could make it more integrated, if you could give it more powerful features, then you'd feel like you have superpowers and you'd be saving hours every week.

Actually interesting resonates with learning. We had we spoke with one of the people who built product original product for wise transferwise used to be known like also huge fintech and they said that pretty much Discover there are three things I remember 2 3rd 1 unfortunately I forgot but if you optimize for speed, cheaper price for users, everything you do in that direction would bring you improvement. So they've kind of used it and kind of worked for them for several years.

It reminds me of something that my business school not business school, my business studies professor, I studied computer science but we had a business studies stream at Cambridge would say which is better, faster, cheaper, choose two. And what I like about the transferwise approach is actually they chose all three.

So now your product is obviously used by a lot of people. How often do you do you still measure product market fit the score? Do you still send out a survey? Can you walk us through some kind of practical routine you do now? Meaning like I don't know, for example, when you add a bunch of features, you try to measure that 50% of users didn't want to lose us and now we added these Things and now 60% of users no longer can live without us. Can you walk us through what you do now with the already more mature company?

We absolutely keep measuring product market fit and it's important to keep doing so. Products market fit isn't a binary. You can have it and you can lose it. And actually the default is that you lose it over time. Because the default if you're a startup, especially if you're venture backed, is that you aim to grow. And so what happens when you aim to grow is that you increase the size of your audience, you increase the top of funnel, you relax qualification on who you accept into the product, which means that over time your audience is less and less targeted and they have lower and lower intent. They are more and more not the early adopter but the middle of the market and you have to cross the chasm to use that phrase. So your product market fit metric will come down over time, which means that this isn't a problem. This is to be expected. Our job as founders and as startup leaders and as startups is to keep that number going up. So we run the survey every single week, just as we have for the last gosh, six or seven years. People sign up for Superhuman, they start using it, and once they've experienced the core value proposition, we typically wait for about two weeks and until they've sent about 20, 25 emails, we then email them the survey. And the survey has four questions. But the idea is to wait until people have experienced the core value proposition. If it was Uber or Lyft, you would wait until folks have taken their first ride. If it was Airbnb, you'd wait until folks have done their first stay. In our case, it's a week or two and you've sent 20 or 25 emails. We still do it on the product as a whole. We don't do it on specific features every now and then when the feature is very large. For example, we talked about Superhuman for sales. It's actually closer to a new product than it is a new feature because it's a collection of features. We're doing it for Superhuman for sales, but otherwise we keep doing it on the level of the product itself.

It's a good point that actually your audience, when you mature, people who buy your product on the second year of your lifespan are totally different. You kind of need to almost adapt. It's like in a relationship, if you're in a relationship long enough, 10 years, let's say, or five years, you're a different person. You both are different people than 10 years ago. So you start still need to keep the fit going. Right.

So like also send out that survey.

Yeah, a good idea for relationships. We're now only not productivity podcasts, but relationship podcasts.

But especially with those same questions, you know, how disappointed would you be if.

You didn't have me in terms of features? Yeah, we briefly pre discussed. You said there are a lot of good stuff coming. In terms of AI, you mentioned sales as well. One thing a lot of every company struggles with is prioritizing and figuring out like product roadmap. So many tickets and features and what to do next and what to roll out. Maybe you can walk us through what methods you have found to figure out. Like out of million ideas, which ones will make it in the roadmap for Q2 2024, for example, I like to.

Classify product projects as either market widening or solution deepening. Market widening makes your product available to more people, but it doesn't make the products better for the people who already have it. An example for us is adding support for Outlook or Android when we already support Gmail or iPhone. Whereas solution deepening makes your products better for the people who already have it, but it doesn't make it available to more people. An example for us again is all of the work that we've been doing with generative AI like Auto Summarize and Instant Reply. And in the book Traction, which is really, really great, the authors Gabrielle Weinberg and Justin Mez have a great rule for this. Spend about half your resources on solution deepening and half your resources on market widening. And we actually codify this in our products market fit engine. If you follow the engine, you'll pretty quickly deeply understand why users love your product. And you'll deeply understand what holds users back from loving your product. And to increase your product market fit score, you should spend half your time doubling down on what users love. In Superhuman's case, that means even more speed, even better shortcuts, even more efficient workflows, even more powerful AI, even better design. But just as importantly, you should spend half your time systematically addressing what holds users back. Again, in our case, that means more integration, better calendaring and admin features for the enterprise. Now, if you only double down on what users love, as vision driven teams tend to do, you won't increase your product market fit score. In fact, it will go down over time as your audience widens. But your product doesn't become more applicable if you only address objections. However, as data driven teams tend to do, a competitor will eventually overtake you by doing your magic, your secret sauce better than you do it. So this is your new roadmap. It automatically writes itself and every single time I've run this, it increases products market score.

Yeah, it's actually another learning we've had. In the podcast a few episodes back, one of guests quoted, I think it was learning from Shopify where they defined that they need to do the most important things super easy. People need to be able to do most important things super easy. But everything else needs to be possible. Meaning some kind of weird integration for E Commerce store. You need to, you know, if it's crucial for a business, you need to be able to add it. And also in that way, sort of simple rules kind of helps you to, to grow and prioritize. So it's kind of love the 5050 split because that's always a thinking like is it 30 70, 10 90?

And by the way, it's a debate. We go into a planning cycle with the assumption that it's 50 50, but it depends on the, it depends on the priorities for that planning cycle, that quarter that month that year. If you're doing 90, 10 or 80, 20 though, I'd ask some really hard questions. Even 70, 30 gets me worried because it means you're probably focusing too hard on growth or too hard on core products. And the reality is we have to do both at the same time.

Another thing you did when you started Superhuman, you took on GMA and Google. And there are a lot of entrepreneurs I think, you know, with ideas and things that, you know, they want to get off the ground. But there's a huge incumbent in the industry and Maybe even the VCs are telling them, you know, guys, what are you doing? Are you really trying to. Are you serious?

Right.

And can you walk us through your thinking through that with a sort of aim to inspire maybe other people who want to take on the big, big players?

Absolutely. And this is easy because entering a market dominated by incumbents is really great for lots of reasons. It's one of the best possible startup strategies. I'll give you four reasons. So first of all, incumbents tend to build one size fits all solutions. Office365 has hundreds of millions of paid seats. Gmail has well over a billion users. Any which way you slice it, these are one size fits all products. You can take their markets and pick a highly valuable but chronically underserved segment and then build the best possible products for them. We did that for prosumers. Secondly, incumbents struggle with building fast experiences. And part of what makes Superhuman fast is actually that it's entirely a client side application. Our web app looks like a website, but it is not. It was actually the first email client ever written entirely in JavaScript. Now imagine if an incumbent wanted to do that. It would be incredibly hard because they are already at massive scale and so the architecture of their products becomes highly entrenched. Thirdly, incumbents really struggle with design. And part of what makes Superhuman so effective is that it has a coherent product and design leadership that I've shepherded personally from day one for, at this point, nearly 10 years. But incumbents products change hands every two to three years as product and design leaders move on with their own careers and then a new set of people move in and now it's a slightly different vision or sometimes a very different vision. And lastly, a lot of founders do find the idea of going up against an incumbent to be very scary. And in a way they're right to be scared. Because if you're looking to build something with that kind of complexity, that kind of surface area, you will need more capital. You'll need more patience and you'll need a bigger team than most startups. And the fact that it is so scary means that way fewer founders will even attempt it, which in practice means less competition for you.

Yeah, especially, especially. I think the first thing that you mentioned, that going up against Google doesn't actually mean having to go up against Google. You don't need to compete with the same product. You can just attack a different segment or one of the segments and make it much deeper. And probably the expectation is you don't have to create a trillion dollar company right away.

Step by step.

Absolutely.

Also another thing you mentioned is this product leadership that stays on doesn't change. It's like almost a government. You know, one government comes in four years, then another one comes in like there's no sort of continuity. It's interesting really. Point Superhuman users are super passionate about the product and can you give us like the secret? So meaning like do you think it's because you really obsessively and pragmatically step by step focus to build the product for them?

Well, in large part the hard productivity results speak for themselves. We analyze 30 days prior to using Superhuman and compare it to the 30 days after. And we consistently see across the entire user base the same few things. Number one, that our users are responding to twice as much email in any given period of time. Number two, they're responding one to two business days sooner. And number three, they're saving four hours or more every single week. And I think this is the main reason why the number of teams using Superhuman has more than doubled over the last two years. And a huge part of why our customers are so passionate. But it's also the little things. It's the attention to detail in our design, it's the delightful and blazingly fast customer support. It's the rapid adoption of AI when you put these things all together, that's the recipe for passionate customers.

Are we heading towards like, you know, with advance of AI, could I in a few months or a year be able to sort of just set some kind of prompt and say like answer all these emails. I don't even look at them. You know, emails coming from this property or group tag. Are we heading there in terms of just envisioning product feature? You don't need to of course disclose something secret you're doing, but what do you think? Where's email heading over?

I think email and for that matter our entire digital world is heading to what we call an agentic future. In the so called agentic future, we'll all have AI agents. In fact, we'll probably each have multiple AI agents. And these agents will be mostly autonomous. You'll be able to give them goals, not tasks. They'll be able to break those goals down into subtasks. They'll be able to work on those subtasks independently and handle ambiguity. If they don't know something, they can ask you or they can go away and research information. They can even interrogate other agents. So if you think about your email in the next few years, it is totally conceivable that you'll have an AI email agent that has deep context about you, that can draft and triage in your inbox. It can take all the emails that are incoming. It can file them as ones that you don't need to read, ones that you do need to read, ones where actually it can handle. And it already goes ahead and writes draft messages on your behalf. Imagine an AI agent that can triage, that can schedule, that can write and even send emails on your behalf. May sound like science fiction today, but I don't think we're that far away.

By the way, you work mostly and exclusively with email, and there have been, I think, times when people have declared email dead and the rise of instant Messaging, Slack teams, WhatsApp, you name it, all kinds of different communication methods. How prevalent is email still today? And what outlook do you see for email as such?

Well, one of the reasons that we do Superhuman is because it is the biggest possible problem that I can find. And it's easy to forget this because we all take it for granted. Email is just sort of wrapped up in our daily lives, but it is everywhere and fundamental to the fabric of business. There are roughly 1 billion professionals in the world, and on average, we spend three hours a day reading and writing email. That's 3 billion hours per day, or north of 1 trillion hours every single year. So yes, of course, perennially, people will say, oh, email is dead. Here's what's going to replace it. But it doesn't die. In fact, it keeps growing every single year and at a healthy, or some might say an unhealthy clip. So the other half of the question is it's about chat, it's about teams, it's about Slack. And obviously I've spent a ton of time thinking about that future and how does email and how does team chat fit together? But I would say that despite their simplicity or perhaps because of their synchronicity, tools like Slack and Teams actually decrease our productivity. They slow our companies down, they erode at our well being. If I were to show you my slack this morning, you would see multiple pages of unread channels, and each one of these channels would contain dozens of topics, all jumbled and interspersed with each other. And as the morning would continue, I would receive multiple synchronous messages of many kinds. Some would be important, some would be urgent, and some would be neither, arguably unnecessary. And yet it would be impossible for me to tell which is which. And even if I could somehow focus on those messages which were important or urgent, they alone would be overwhelming. I would reply to some, I would drop the ball in others, and when I dropped the ball, I would be missing opportunities, I'd be slowing down my team, I'd be living in an increasingly anxious state. Now, I've been in Silicon Valley long enough, and I've been a products person for long enough to know that that's all kind of by design. It's to keep you addicted to the hamster wheel of continuously checking slack or teams. So in the next few years, I believe that we're going to see a massive reinvestment in email, in task management, and in the core fundamentals of productivity and collaboration.

You heard it here first, the phrase.

About email that it's like, I remember when I started my career more than 10 years ago, I was in email marketing. I heard the phrase then, you know, in conferences, block email is gone to be dead because of social media. It's still there, it's still selling, It's.

Yeah, there are parts of it which are remarkably well designed. That's why it pervades the fact that you have subject lines, the fact that conversations are ordered not by when the first person happens to start them, but by when the last person happens to reply. The fact that you can mark things as done, that you can snooze, that you can star, and when you use next generation products like, like Superhuman, we've got things to come. Soon you'll be able to share threads with people so you don't have to constantly forward or BCC conversations with vendors or investors or candidates that you're trying to hire or customers. You'll be able to leave comments and you don't have to worry that those comments will leak externally. I'm sure we've all experienced that. It's mortifying whenever it happens. And so there is this deep stream of innovation that companies like Superhuman are pursuing.

Want to talk a bit about fundraising as well. So we established that Superhuman has raised a lot of capital, so you've been on that side of the table. You're also active investor and angel investor, so you're also on the other side of the table. Maybe one question in terms of when you go in to present your product and it's not your first company, can you tell us how you. For example, I would like to structure the pitch. Is there some kind of flow that you follow? Some kind of rules? We always talk, I don't know, start with problem and then solve it. Or is there any kind of structure that maybe others can get inspired by?

Early in my founder journey, I struggled with pitches. I compared us to small companies, not to big companies. I was cautious and balanced, not confident and bullish. I spoke too much about the present, not enough about the future. And it took watching many great pitches and imbibing Silicon Valley culture for many years to fix this, to strongly pitch a future, to make success seem inevitable, and to truly think big. In terms of the actual structure of the pitch, I think I sort of build it from scratch every single time. And I don't worry too much about the structure. In my case, I set the stage with the market that there are a billion professionals in the world, 3 billion hours a day, north of a trillion hours a year. I bring this back into email. I then describe what we built, which is the fastest email experience of all time. I then explain the core value propositions you're going to get through your email twice as fast, respond faster to the things that matter, save four hours or more every single week. And then I jump into the metrics. This is for more recent raises where we have a product and we have metrics. Metrics like what is our daunt to MAU ratio? How many hours a day do people spend in the product? What's our retention? What's our churn, what's our product market fit score? How viral are the users? What are our activation and engagement rates? And then of course, what is the growth rate of revenue? Ultimately businesses have to grow in order to survive. And then I talk about vision. I talk about what it means to build the productivity and communication suite for high performing companies. What it means to build the AI powered workplace of the future. And then I like to break that down into three acts. And for email, for us there's just Act 1, but there's an Act 2 and there's an Act 3. And then I like to talk about what Act 2 and Act 3 actually are and how they take us from being a $1 billion company to a $10 billion company to a several hundred billion dollar company. Now that's My structure. But the actual structure doesn't matter. What matters is that you're telling a big billion dollar story and that it's rooted in things that make you believable and that you're confident and bullish and that you're comparing yourselves to big companies and that you're in the future, not too much in the present.

In terms of climate now, in terms of rising funds, obviously you're in, I think series C was the latest. Right. You raised, so you're quite an advanced company already. But what do for next few years and for other founders, Is fundraising going to be difficult or if you have a good story, good vision, billion dollar idea and you can still do it?

Well, it depends on your frame of reference. Is fundraising today as easy as it was for the last three or four years? Definitely not. I mean, there was this period from 2019 to the middle of 2022, or I would say probably towards the end of 2021, where fundraising was as easy as it had ever been. And I think we all know the reasons why. I'm not going to get into that, but it's certainly not difficult. I first was raising funding in 2010, 14 years ago now for my company Rapportiv, and I tell you, that was hard. That makes today's climate look easy. Round sizes are bigger, VCs are way more numerous, fund sizes are larger. And actually it's also easier to build companies. You need fewer people. There's so much more infrastructure, there are so many more services that you can build on. Open source is way more prevalent and you have new enabling technologies like AI, which not only help you build better products, but they just help you run companies better. You need fewer customer support people. You at some point will probably need smaller sales teams and it's going to be a rising tide for all boats. So I would say today is middle of the road. It also depends on your industry. If you are a AI founder with a great resume, with a great track record, sure there's money being thrown at those founders. But I would caution any founder who raises too much money because it starts to cut off options, raising money is a up until a certain amount, I would, let's say up until 1 or 10 million, you're probably fine. But once you've raised more than $10 million, you need to be very, very careful and you need to make sure that you know what you're doing.

Yeah, it's an uncommon piece of advice. What about some other advice like on the fundraising? You know, we usually focus on things you should do. Is there any kind of advice going around that you think it's like over emphasize or maybe not really a good advice, that some founders fall with less experience, can fall into some traps? It's like kind of any kind of bad advice to steer away from? Not really.

There are many, many ways to screw a pitch up and to be bad at fundraising, so that's not particularly interesting. But the ways that people succeed, they usually look the same. When I'm investing, I look for three very specific things. Number one, founders who have the magic combination of a they know how to make something people want and B they know how to make people realize they want it. If a startup only has one of these, it won't be able to succeed. Number two, I look for founders that demonstrate exceptionally high levels of grit. And I think of grit as the combination of passion and perseverance. Passion means the founder will not easily get distracted with new interests or goals. And perseverance means the founder will follow through with hard things despite challenges. And number three, I look for a clear narrative to a billion dollar outcome. Not one that I invent. It's very easy as an investor to do that, but one that the founder clearly articulates. When we end up passing on great founders with good businesses, it's because we were not able to get conviction that the business could support a huge outcome. So those are the three things.

Awesome. Well, being in productivity space, we cannot skip this question for you yourself. In your daily work, what are some of the tenets of your productivity? Could be tools can be routines, something that you found after years and years of trial and error that you think works. Obviously can be different for different people. But just can you share something that you found helps you to boost your productivity?

Maybe some good way to manage your email?

Of course. Well, I was going to say, actually my biggest productivity gains come from one of the most powerful superhuman features and that is split Inbox. So think about your own inbox. If you're like most people, you get way too much email. The urgent buries the importance. We don't reply to our team or VIPs, we miss notifications from tools like Notion or Google Docs, and as a result, we lose opportunities, we damage our reputation, we let down the people who count on us. But with split Inbox, you can respond faster to what matters most. So let's take my inbox where I receive more than 1,000 emails a day. It's an infeasibly high volume to process directly. How do we make sense of this? Well, I want to be hyper attentive to our engineers. If somebody mentions me on Linear, they probably want me to finesse a color, write some copy or test a feature. If I delay or miss these requests, I slow the entire company down. So to focus on these mentions, I've made a Linear split inbox. This pulls all emails from Linear out into their own stream. I can then star, snooze and marketer and I can get through them one after another and not be distracted by other types of email, but that's just linear. I also want to be very attentive to work that's happening elsewhere. We literally run our company on tools like Notion and Figma and Google Docs and in Gmail. I would miss these all the time. We've all been in a conversation that goes something like, hey, did you send me the doc? Yeah, I shared it to you two days ago. Oh, I didn't see it. Let me go and find it now. I want to be the best teammate, the best leader that I can possibly be and a big part of that is rapid response. So to get to these notifications quickly, I've created splits for Notion and Figma and Google Docs and now I can quickly unblock my team. I can increase our overall pace of execution. And those are just tool based splits. You can also create custom splits for specific mailing lists or launch campaigns, whatever else is going on at your company. And that's my most powerful tool for focusing on what matters most.

So when your boss is writing you, you can put it in a separate split where you definitely don't miss that.

One in the last place.

Exactly. We have a VIP split. I use it for certain customers, for certain investors, board members and it's a pretty popular one.

Awesome, awesome insights, awesome conversation. Thank you very much Raul for joining. I think we learned a ton. We need to process it now for the. For the listeners. There's some really good material Raul has worked on on product market fit. We'll do it. Plug it in the description of the episode as well. I'll read through it. It's. It's a very detailed instructions of how also you can. Any company, any field I think can benefit from. So yeah, check that out as well. Check out Superhuman for sure as well. Thank you once more.

Thanks Rahul.

Bye bye. If you like this show, remember to leave us a rating or review. It helps other people to discover the pursuit of scrappiness.