Rahul Vohra of Superhuman

Founder Coffee episode 037

I’m Jeroen from Salesflare and this is Founder Coffee.

Every few weeks I have coffee with a different founder. We discuss life, passions, learnings, … in an intimate talk, getting to know the person behind the company.

For this thirty-seventh episode, I talked to Rahul Vohra, co-founder of Superhuman, the company behind the self-proclaimed fastest email client ever made.

After Rahul sold his previous company Rapportive to LinkedIn and spent a while there as a product manager, he decided to take on the challenge to rethink one of the most fundamental software programs of today’s knowledge worker: the email client.

Rahul’s dream as a kid was to be a game developer and he taught himself how to code starting from the age of eight, which he first did alone and then later as a professional game developer at Runescape. It’s this gaming background that he leverages at Superhuman to try create the best possible email experience in the world.

We talk about how Superhuman goes about prioritizing growth projects, his career detour starting a PhD in machine learning, how playing Dungeons and Dragons keeps him inspired, and why you need to aim for either growth of users or growth of revenue, but not both.

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Jeroen:

Hi Rahul, it’s great to have you on Founder Coffee.

Rahul:

Great. Thank you for having me.

Jeroen:

You are the co-founder of Superhuman. For those who don’t know yet what do you guys do at Superhuman?

Rahul:

Superhuman is the fastest email experience in the world. We help our customers get through their inbox about twice as fast as before reply, so they’re reporting to email sooner and see inbox zero for the first time in years.

Jeroen:

Cool. So do I have to see it as an email client?

Rahul:

You can see it as an email client. Yes.

Jeroen:

Yeah. So you are basically here to replace sort of outlook or Gmail or mail on Mac?

Rahul:

Kind of. You don’t stop using exchange behind outlook or Gmail. Those accounts still exist. Your email address stays exactly the same, but what you do get is an interface that lets you move about twice as fast through your email.

Jeroen:

Yeah. And thinking about why you started this, is this something you were experiencing yourself— that you didn’t like any of these programs. And you were like, there must be a better experience. How did that spark exactly happen for you to start Superhuman?

Rahul:

Well, to understand the founding moment behind Superhuman, we actually have to wind the clock back by around 10 years, because in 2010, I started a company called Rapportive, which you may remember we built to first scale to millions of users and when people emailed you, we showed you what they look like, where they worked their recent tweets and links to their social profiles. And we grew rapidly and two years later we were acquired by LinkedIn.

During those four years, I developed a very intimate view of the email. I could see Gmail getting worse every single year, becoming more cluttered, using more memory, consuming more CPU, slowing down your machine and still not working properly offline. And on top of that, people were installing plugins like ours, Rapportive, but also Boomerang, Mixmax, Clearbit, you name it, they had it.

Rahul:

And each plugin took those problems that I just listed of clutter, memory, CPU, performance offline, and made all of them dramatically worse.

So it was time for a change and we imagined an email experience that is blazingly fast where the search is instantaneous, where every interaction is a hundred milliseconds or less, an experience where you never have to touch the mouse, where you could do everything from the keyboard and fly through your inbox. And the experience of course that just worked offline so you could be productive anywhere and an experience that had the best Gmail plugins built-in natively and was yet somehow subtle, minimal and visually gorgeous.

And so with that, we built Superhuman.

Jeroen:

So I feel that your initial sort of pain is one performance, second sort of visual clutter. And third, maybe you add some sort of power user aspect to it.

Rahul:

Exactly. It’s power-user features that help you get through email faster, spot the important email faster. And then one of the things that people love the most about Superhuman is the ability to maintain their inbox at zero.

Jeroen:

Yeah. Cool. Is your user base mostly power users or is it more sort of channel?

Rahul:

It’s mostly for people for whom the email is work and work is email. Our average user spends three hours a day doing email.

Jeroen:

Well, that’s a lot of hours in your email.

Rahul:

That means a lot of work.

Jeroen:

Okay. You mentioned that previous to Superhuman you were at LinkedIn, I suppose?

Rahul:

That’s right.

Jeroen:

And previous to that you were working on Rapportive?

Rahul:

That’s correct.

Jeroen:

For those who don’t remember, Rapportive was a Gmail plugin that showed you the LinkedIn profiles of contacts within your emails, right?

Rahul:

Correct. Yeah, we did LinkedIn profiles. We also linked out to Facebook and we showed recent tweets and information from other sources. The idea was to give you everything that you could possibly need to know about your contacts right inside your inbox.

Jeroen:

Yeah. And previous to Rapportive, did you do anything else professionally or was this like your first thing?

Rahul:

Prior to Rapportive, I did have a number of companies that I attempted to start probably six or seven attempts, depending on how you count them. Somewhere in the video game space – somewhere in the space that is currently occupied by Kickstarter and Patreon. And for some of them, we even raised a small amount of money, but the first to actually get any level of success and traction was Rapportive.

Jeroen:

And did you also have, apart from that some quote-unquote real job as people would say or was your time fully on starting startups?

Rahul:

No, I’ve never actually had a real job. I think the closest I came to having a real job was when I was at LinkedIn. And I was a product manager there, which is usually what happens to a CEO when they get acquired.

Jeroen:

Yeah. Cool. So right after university, you basically decided you were going to startup. And that’s what you’ve been doing all along except for the little LinkedIn detour there.

Rahul:

Well kind of, so after university, I started a PhD in machine learning and computer vision and pattern recognition. And I did that for about one and a half years. But I realized in going into the PhD that my motivation had been wrong. You see, I started a PhD because I thought it would be a good way to start a company. I did some technology and then I would commercialize. Then I realized that the best way to start a company is in fact just to start the company.

So I dropped out of the PhD. I then briefly ran the POS of the university that helps staff and students create businesses. I would help staff and students write business plans, meet teammates, potential co-founders, and also raise their first bits of angel money. And then after that, I got into building my own companies full time.

Jeroen:

Cool. So I think you’re the first person on this podcast that actually went through a PhD to then start a company. But I do recognize the pattern from when I was at university. Basically you do a PhD and you hope that will spin-off, you’ll start up a company. Right?

Rahul:

That was the hope and I should clarify, I didn’t finish the PhD. Normally it would have taken four years or more. I only managed to do it for one and a half years.

Jeroen:

Yeah. Understandable. If your goal is to start a company.

Rahul:

Right.

Jeroen:

And previous to this PhD, were you already dreaming of starting companies or doing projects or is that something that started somewhere around there?

Rahul:

Absolutely. I knew I wanted to be an entrepreneur as early as 14 or 15 years old and I’d actually been programming computers since the age of eight.

Jeroen:

Eight. What were you doing in terms of projects then when you were, let’s say between eight and in your PhD?

Rahul:

Well, that’s quite a widespread of time, but at around the age of eight, the way that I got into programming is at the end of the school day, I was often hanging around waiting to be picked up by my parents, who would sometimes finish their work late. And so I would go to the school library and after I’d read all the fiction books, I started on the nonfiction books and came across a section on how to program computers. And I thought, well, this is so exciting because if I could learn how to program computers, I would be able to make my own video games. And so I read all of those books and around the age of eight or nine, I started to teach myself how to program with the intention that I would create my own video games. And then all the way through secondary school, I doubled down on that.

Rahul:

So I went from programming in basic through to visual basic, visual basic two. At the time it was very early all the way through to visual basic six, which became advanced enough to have things like pointers and other real programming language constructs.

Then I taught myself C, then I taught myself C++, made all kinds of things as I was growing up. Some of which actually got reasonable amounts of traction and distribution. But actually, by the time I’d gone to university at around the age of 18, I’d already done many hours of programming.

I’m not sure if you believe in Malcolm Gladwell’s 10,000-hour rule. It takes 10,000 hours to become sort of competent at a thing. But I was very fortunate to have had 10,000 hours of programming by the time I went to university. And that meant at university I could focus on the theory behind computer science and also all of the other things that have made me a successful entrepreneur over the last 10 years. Things like marketing and design and psychology.

Jeroen:

You mean you followed courses at the university about that?

Rahul:

Yeah. So one of the great things about Cambridge where I went to study is that students can turn up to any lecture.

Jeroen:

Nice.

Rahul:

Well, I would just turn up to lectures that I found interesting.

Jeroen:

That’s sort of a dream for people who are into entrepreneurship, I would say.

Rahul:

Exactly.

Jeroen:

Out of the games you developed while you were a kid or a teenager, what was the coolest one that you developed?

Rahul:

The coolest game. Excuse me. Yeah. So I was very into fighting games at the time, street fighter or mortal combat or smash brothers. And so I developed my own version of a fighting game called Stick Fighter.

And it was pretty interesting that it was based on a physics engine, I’d modelled out the limbs, the spine, the bones in the body. And the collision between the characters was actually based on the bones that your characters have moving and how fast they were moving and where they struck the other character. And so that was actually a pretty fascinating piece of code to write. I then also briefly did work as a professional video game designer. So I worked on a Runescape which for those that don’t remember was the largest online role-playing game at the time. And I developed quite a few quests for Runescape.

Jeroen:

Is there anything that you developed that we can still check out somewhere online?

Rahul:

Yeah, so the content I developed for Runescape is still very much online. The most famous quest and piece of content that I did inside of that game is called Monkey Madness. And people who’ve played the game will know exactly what I’m talking about. It’s one of the legendary quests, which is rather fun to go through.

Jeroen:

Cool. And I hear that you sort of felt this need to create stuff from when you were eight. Is this something influenced by your parents or what is the profession of your parents?

Rahul:

They’re both doctors.

Jeroen:

Both doctors. So they’re not really creative people?

Rahul:

Well, I would say actually they both are. They’re both doctors, but they’re both very prolific doctors, meaning they always have a stream of research going on. They always had entrepreneurial activities of their own going on. They were doing private practice as well as serving in public hospitals.

Sometimes there would be a collaboration with military endeavours when soldiers came back from war. So there was always something really interesting happening in the house. And they had their fingers in many pies, so to speak. And I really enjoyed the entrepreneurial way that they approached the profession of medicine. And I thought, well, okay, I want to be an entrepreneur.

Jeroen:

Yeah, that’s sort of unusual for doctors. There are doctors like that. I know a few, but they’re not like many. I mean the doctor normally works through patients but does not build anything, let’s say.

Rahul:

Exactly.

Jeroen:

So you mentioned you got into startups through the library. Or were there any sort of entrepreneurial role models you followed? Were there any people that particularly inspired you?

Rahul:

Entrepreneurial role models that’s a really great question. I don’t think I had entrepreneurial role models. There were certain people that definitely inspired me along the way, however. I can think of one off the top of my head.

So when I was here in California running Rapportive, there was a period in the company where we were running out of money and I had to go out and raise more money. And I’d put together a pitch deck and I was meeting with this person. His name is Jonathan Siegel.

At the time, he had acquired two era logging companies. Airbrake and Hoptoad, and had merged them together, had sold them to Rackspace and was busy being a full-time investor and incubator of other startups. I really love hanging out with Jonathan because he has such a unique way of seeing the world.

I went into his office, I presented my pitch deck and he was like, “Yeah, that’s fine, but it’s not very good. Here, let me show you how you can pitch it.”

Rahul:

And he took exactly the same size and just off the top of his head delivered a pitch back to me that was so full of confidence and energy and belief and I was like, “Wow, I want to invest in new students business.” And for my business, he made it sound incredible. And that was very inspirational for me.

I think that a lot of how I pitch businesses today stem from that moment, that level of confidence and energy and just sheer projection of will into the world.

Jeroen:

Cool. Is there anything from there that you can share with the listeners? Any tip you can distil from there?

Rahul:

Do you mean tips about how to pitch?

Jeroen:

Yeah, how you pitch because you said it’s full of energy and projecting a lot of confidence, but was there anything in there that is shareable with other people?

Rahul:

I don’t think there’s a specific tip. It’s more about the style and the vigour which he brought to that particular moment that was inspirational for me. I think the tip in order to make it actionable, what I would recommend to listeners is once you have a pitch, take it around various mentors and ask for that feedback.

Now, most of the time the feedback’s not going to be that great or it’ll be fairly hollow. Like yeah, I think this is fine, but every now and then you’ll find someone who’ll be like, “This isn’t very good.” And they’ll give you their version of the pitch and if you’re lucky, their version of the pitch will be fantastic and that will inspire you to make it even better.

Jeroen:

Yeah. Cool. You mentioned that both Rapportive and Superhuman are VC funded startups, right?

Rahul:

That’s right.

Jeroen:

Is that something you consciously choose for? And why did you?

Rahul:

Well, Rapportive was a venture-backed company because of a number of things. Number one that we knew we needed to build it here in California and when I started the company we were in the UK. So we needed to find some funding in order to make that transition.

Number two, we needed to hire a fair number of engineers to actually build a product.

And number three, we didn’t know when we started it, how we were going to monetize it. And so that’s the main reason that we raised money for Rapportive.

For Superhuman, it’s all of those things. Plus, in order to actually build an email experience that not only do people want to use over Gmail but does significantly better than Gmail. You need a big team, you need to raise tens of millions of dollars. And you need to work at it for a good period of time.

So we’ve so far raised $51 million and we have a team of about 40 plus people here at Superhuman working on what we do.

Jeroen:

What is exactly your ambition with Superhuman? Is it to replace all the email clients in the world or is it slightly more specific than that?

Rahul:

We definitely don’t want to replace all the email clients in the world. I think down the line we’ll become a multi-product company. You see for us, email is just a starting point. We potentially want to take on all of the things that professionals do that isn’t the direct meat of their work.

Whether it’s tasks, calendaring, scheduling. There’s lots of incredible things that we can pull together. And number two in the next few years, I love to see a Scrooge become a billion-dollar organization and I think we have a really great shot at doing that. And personally I’d love to become the kind of CEO that can facilitate and lead that kind of growth.

Jeroen:

Yeah, so it’s sort of, you want to become a leader in let’s say B2B productivity apps?

Rahul:

Almost. Superhuman is one of those interesting companies where the way that our users think about the product and the way that we go to markets and the brands that we have, is actually closer to a B2C company than a B2B company. However, the way that it’s paid for and the work that it’s used for is definitely B2B. We charge $30 a month and it’s used to make companies move faster and more effectively.

Jeroen:

Got it. Just a bit more about how this all evolves for you personally? And you mentioned you have a 40 plus person team right now. What role do you play in the company currently? I mean you’re the founder and CEO, but what does that role mean right now?

Rahul:

Right now, that boils down to a few different things. Number one, and this is the most important one, is building out the team. This can be anything from hiring executives and new leaders into the company.

For example, right now we’re building out how a marketing organization, even to this point, we don’t have anyone other than me and one or two other people in the company working on marketing. And so it’s time to actually build that organization from scratch. So I’m hiring for a head of marketing, a lead of demand generation and a lead of content.

Apart from hiring, the rest of my role falls into setting strategy and direction. So that’s one of the really big things that we’re going to do this year in order to inflect harder than we even are. And thirdly— and I think this is important for a product founder— retaining the head of product role to make sure that we keep on doing the things that made us successful in the beginning.

Rahul:

We keep on building a product that’s exceptional and over makeable quality and that creates delight for our users.

Jeroen:

Yeah. If I hear it well, you’re working on product marketing strategy and hiring.

Rahul:

Exactly.

Jeroen:

Yeah. Is that a bit overwhelming or is that something you can easily manage?

Rahul:

I think it becomes more and more manageable over time. So there is this period at the start of any company when it’s just you and maybe a handful of other people and everything is fine because very few people are asking for your time. You can only do what you can do in those hours and it’s actually a fairly relaxed period. And then if you’re lucky, you’ll find something that works. In other words, you’ll find product-market fit and now you’re on the other side of product-market fits. And to use a metaphor— in the early days, you’re sort of pushing this boulder up a Hill.

When you find your product’s market fit, you reach the top of the Hill and now you’re trying to chase the boulder down the Hill and it’s running away from you. And that’s when things can begin to feel overwhelming because you have to hire it as fast as possible. You have to scale as fast as possible and you have to do those things without sacrificing the usually non-scalable things that made the company special.

Rahul:

And so that’s the period where it can feel overwhelming. And what will happen is you will start to hire and scale and bring in more people, more individual contributors and great leaders. And ultimately you should be delegating as much as possible away from the day to day. So you can once again focus on strategy, direction and picking the next great thing.

Jeroen:

Yeah. So you’re actually ahead of hiring versus scaling right now?

Rahul:

I wouldn’t say ahead of hiring. I think we’re on pace with where we need to be. My goal is to get ahead of hiring versus where we need to be.

Jeroen:

Yeah. Well, what is it that you spend most of your time working on right now? Of all these things we just mentioned?

Rahul:

Well, currently we’re at the start of the year, so my big project is setting strategy. We’re looking to inflect the company even harder than we otherwise would. And so me and my staff – that’s the people that work directly with me, our big project currently is to figure out what those things are that are going to inflect the company.

Jeroen:

Yeah. For those who are doing the same thing right now, how do you exactly go about this?

Rahul:

Yeah, great question. So first of all, I think you want to start with a goal. Let’s say that, in this hypothetical startup, you started the year at zero revenue and you got to $1 million of ARR by the end of the year. And right now, your projections are telling you that by the end of this year you’ll get to $3 million of ARR. And that’s good, that’s nice and fast.

But if you want to raise venture funding, you really need to get to $4 million or $5 million. And how are you going to do that? Well, now we have framed the question. The question is how can we add $2 million of annual recurring revenue to this year’s plan? And what I would then do is have a brainstorm. And this can be done just with leadership or you can do it using everyone in the company.

Rahul:

The key is to leave the office and to go to some other new location. The location where it’s not familiar to anybody. Take the time, get relaxed, get settled in, have a coffee or have a Coke or whatever and then get brainstorming. And now the key thing with a brainstorm is that no idea is a bad idea, and everyone should have the opportunity to throw in whatever idea they want. You should be having fun, you can play music in the background. If the energy gets stale at some point anyone should be able to shout switch or some other keyword. And then everyone can swap seats just to keep the momentum flowing throughout the room.

Ideally, you want to get to hundreds of ideas and most of those ideas will be terrible and that’s fine. But getting to hundreds of ideas means that there will be a few gems in there. And then afterwards leadership, usually the CEO or the head of strategy should take those ideas and assign them scores.

Rahul:

And what I like to do is I assign each a cost and an impact, high, medium, low. And this allows you to stack rank the ideas. So you’d be able to say, well, this is a low cost, high impact idea. Well obviously we should do that and maybe we’ll save the high cost, high impact ideas for later when the team is larger. So then you have a list of stack ranked ideas.

Then later on in the company, maybe next week you can have people vote on those ideas. And there’s various ways you can do voting. You can one that we’re doing right now is give everyone a $100 of voting currency and you can split those hundred dollars of those concurrency up between the ideas, depending on how much you care about each of them. And then you’ll get a sense of how the company is feeling about all the ideas.

Rahul:

And then you probably need to do some analytics work. So previously you have estimated the costs, you’ve estimated the impact. You probably actually want to do some real analytics work to come up with not just an estimate of impact, but a real prediction of how many dollars each idea is likely to add to your end goal.

And you’re going to want to ask the engineering team to have a more detailed estimate of how expensive something will be to build beyond just high, medium, and low. And then once you have your estimates, both of the costs to build and also of the impact to revenue, you would then actually be able to make real trade-offs in terms of how much time you have and what impact those projects will add to the end of year revenue. And that’s the process that we run and it’s rather a good process and it’s what I would recommend to anybody else.

Jeroen:

Yeah. These are sort of additional projects, right?

Rahul:

Yes. So these are all projects that would be additional or instead, a part of certain aspects of our current plan.

Jeroen:

Yeah, it sounds like a really great process of going there. One question that came up in my mind when you were explaining it is the initial sort of scoping for the ideas. Like do you say to your people so we need two million in revenue, more gives ideas for that or does it go more specific than that?

Rahul:

Well, you can frame the question in multiple different ways. One way is how do we generate an extra $2 million of revenue. Another way would be what could we be doing that would make $5 million of revenue? And I think either framing is totally fine.

Jeroen:

Yeah. But that’s how you frame it.

Rahul:

Exactly.

Jeroen:

Yeah. I think what we do, instead of focusing fully on the end goal, we like to make the sessions more focused by choosing a specific part of the funnel within which we find ideas. Because otherwise, we find that we have this enormous amount of ideas and it’s very hard also for people to think without limits.

It’s very easy if you do set some sort of a framework in which people can think like if you limit something, then they will be more ideas within a certain area is what we found. And we then do sort of multiple sessions throughout the year and always around one of these that could get some improvements. That doesn’t necessarily go bad, but where we see room for improvements.

Rahul:

Right. I couldn’t agree more about the constraints. And that’s actually a technique that we use in our brainstorming every time. So we had constraints like, well, what if we have to achieve the goal in just one week? What would we do? Or what if we had to achieve the goal without spending any money at all? And then opposite constraints. What if we had 10 years to achieve the goal? Or what if we had infinite resources to achieve the goal?

So adding constraints and then rapidly taking them away, we have found that it flexes the creative muscle and just gets lots of new ideas coming out that otherwise would not.

Jeroen:

Right. So it’s one sort of brainstorming session, but within that session you do part sessions in which you say, “Now we’re thinking, what if you have to do it in a week?”

Rahul:

Yeah, exactly.

Jeroen:

That sounds like a good idea. Well, thank you for the idea. If I would be you and I would take over your job for a day, what would I be doing? We understood what your responsibilities are right now, but how would my day look like?

Rahul:

Yeah, so the vast majority of my time goes into, as I said, recruiting and scaling the team and that’s usually 30 to 40% of my week. So depending on which day you take over will determine how the time plays out.

A lot of this is internal work such as specifying roles or working on interview plans. And a lot of it is also external work such as selling, interviewing, and closing candidates. The next 30% goes into product and design. This is everything from commenting on product specs and high-fidelity designs through providing feedback on prototypes and works in progress to something like we just talked about – working on overall product strategy and company direction.

Rahul:

Then the last 30% goes into management and that’ll be one to ones with my direct reports. That’ll be my staff meetings. And anything ad hoc that I need to take care of. We also on top of that, have board meetings every six weeks that provide useful rhythm throughout the year and the remaining times such as it is, gets splits between a few other activities – being the face of the company on Twitter, doing the occasional support, email copy editing, blog posts and product updates and occasionally spending time in person with customers.

Jeroen:

Is there a sort of fixed structure to this or is it more of a complex schedule than what I would think?

Rahul:

Some of these things have a fixed structure. So the management aspects, the one to ones with my direct reports and the staff meetings, they’re pretty fixed. Other things such as the product strategy and the interviews get scheduled around those.

Jeroen:

Got it. Similar here. A bit of a different question perhaps. What do you think are the skills that you as a Founder bring to Superhuman? What is it exactly that you’re known for?

Rahul:

Got it. So a few different things. Over time I’ve developed, I think a fairly tuned intuitive sense of what people want. What consumers want out of their products, how they will feel when they’re using them, and how to choose and tweak those products to create positive emotions and ultimately delightful product experiences.

So products and design would be the first thing. How to make something people want.

The second thing would be marketing. Once you’ve made something people want, how do you help them realize they want it? And I knew to go into Superhuman that we would have to be half a marketing company and half a products company. Because you can build the best email experience in the world, but unless you get the story out there and help people realize they need it, the company isn’t going to be successful.

Rahul:

So telling a big story and marketing a company, helping users realize they need the product is another thing that I think we do on a world-class level.

And then the third thing, and this is really key for anyone building a company like Superhuman is fundraising. I’ve been doing venture back startups for quite some time now and have been an investor as well on the other side of the fence for quite some time now.

The combination of those two activities gives me a somewhat unfair advantage when it comes to raising funding because I understand the investor mindsets. I think that gives me a bit of a leg up when it comes to the fundraising conversation. And when it comes to sharing the story of Superhuman with venture investors who have been very excited to invest in the company.

Jeroen:

Yeah. So if I would have to summarize in very short, you sort of developed a high level of empathy for users both on a product and a marketing level and with investors as well being one as well.

Rahul:

Yeah, exactly. That’s a good summary. If you were to boil everything down to one word, it would just be empathy. Whether it’s for users of the products or potential customers or potential investors.

Jeroen:

Yeah, that sounds like something every Founder, well at least every CEO should definitely have as one of the main skills. Or do you think you could do without it?

Rahul:

There are different paths to success. I happen to be the classic product technology-oriented founder, but there are also sales-oriented founders who would probably outsell me a hundred to one in terms of their ability to go out and aggressively find and close revenue.

There are also management and execution-oriented founders, folks who can drive such high levels of products and efficiency through the company. That’s how they win. And then there are also relationship oriented founders, management who are just so and beloved by their company and that’s how they win. There are many ways to build a company and trying to do all of the above I think is impossible.

Rahul:

The key for a founder is to understand what they are world-class at and to double down on that and then to hire leadership around them to fill in the gaps.

Jeroen:

And if you understand your own basic skill let’s say, should you align the company that you’re trying to fund to that?

Rahul:

Yes, I think so. So in my case as product design, marketing and fundraising and the way that we’ve built Superhuman is very much aligned to take advantage of those unfair skill sets.

Jeroen:

Slightly different angle again. We talked about what skills you’re known for. What are actually the things that give you energy, when working on Superhuman, what is the thing that keeps you going, gets you in a flow state?

Rahul:

Working on the product for sure.

Reading product specs, thinking them through leaving commentary, designing workflows, reviewing designs, especially tweaking designs, making things look prettier. These are all things that provide me a great deal of flow.

But also working on press provides me with a great deal of flow. I was in New York earlier this week doing a TV interview with Yahoo Finance, a radio interview with Bloomberg. The opportunity to tell the story, to evangelize, to share with the world what we’re doing. That also provides me with a great deal of energy.

Finally it’s scaling the team. And there’s nothing more rewarding I think than the feeling that the company grows more and more effective and can do more and more every single month because all these fantastic people are joining the team and I can literally feel the velocity of the company pick up as we grow who we are.

Jeroen:

Yeah, definitely. We talked a bit about your day already and what you do. How do I need to imagine your work hours? Like from what time to what time do you work?

Rahul:

It really depends on what phase of the company we’re in and if I personally have a project that depends on hours versus depending on decision making and all being creative.

So for example, let’s say I’m fundraising. Well, that’s an hours driven activity. I might be working from nine in the morning till nine or 10 in the evening. On the days I’m pitching and I’m working on the deck, it could be mornings only and then in the evenings I’m having coffee or drinks with various investors.

But that’s an activity that probably takes a month in any given year. It’s not normal for me to be doing that.

More normal hours for me would be starting at nine or 10 in the morning and then rolling through to six or seven in the evening, taking a break for dinner and then maybe doing another hour on the other side. And that is a little bit less intensive, but it’s a lot more sustainable and that allows me to take higher quality creative and strategic decisions all the way throughout the rest of the year.

Jeroen:

Yeah. When you work fewer hours you mean?

Rahul:

Exactly. I think that us, Founders, can easily fall into the fallacy of – well all I have to do is work harder. And there is some truth to working harder, meaning that you’ll end up being luckier, but only if you can preserve the quality of your thinking and decision making throughout those hours. Most people actually can’t do that. And I’m included in that set of most people. I know that if I push myself to my limits, then after about three weeks or so, the quality of my thinking will start to deteriorate. And so I can only do it for short stretches at a time.

Jeroen:

Apart from limiting the amount of hours that you work in a day, are there other ways you try to preserve this?

Rahul:

Preserve energy?

Jeroen:

Yeah. Preserve this energy indeed.

Rahul:

Yeah. So the key thing here is to set up an efficient calendar. I batch all of my one-to-one meetings on Tuesday and I do my staff and group meetings on Wednesday and I advise my direct reports to do the same, or shift it one day earlier so they can get ahead of any issues. They batch all of that one and one’s on Monday and their staff and group meetings on Tuesday.

This way we’ve solved the most critical things by Wednesday and we all have as much unbroken focused time as possible. And I actually put blocks of focused time on my calendar, so that is time for high-quality deep work. So that’s the first thing.

Rahul:

The second thing of course is to use Superhuman and I use it to blaze through my email. I’ve never had to touch the mouse. I set up snippets to automate repetitive emailing and I use a feature in the product called ‘split inbox’.

That makes the inbox mirror the structure of my day. So for example, I have a split for GitHub so I can unblock all the engineers first thing in the morning. I have a split for Google docs that allows me to quickly get to any comments on documents that we’re collaborating on right now. And then I have a split for my tasks that allows me to process my tasks without being distracted by new incoming email.

Jeroen:

Okay. Is there anything you do next to work to preserve that? Let’s say, a few things that you could do. For instance, sleeping along doing yoga, sporting, I have no idea.

Rahul:

Sure. So in my free time, I love to do things that keep me a creative storyteller and keep me inspired. And so right now, I’m loving playing D and D or Dungeons and Dragons and I’m currently playing in one campaign and I’m also running another. And I find that D and D gives me a wonderful creative outlet. I can further skills, I already have so much for storytelling, but in an entirely new setting and I can work on skills that are much more nascent, such as acting and improvisation.

Jeroen:

You’re part of any acting and improvisation groups?

Rahul:

Not outside of the D and D campaigns. And I think that’s good enough for now, but I’ve toyed with the idea of taking some acting classes.

Jeroen:

Cool. What else do you like to spend your time on when you’re not working? Is there anything else or is mostly D and D right now?

Rahul:

It’s mostly D and D, which is a fairly time-consuming hobby. And long periods of vacation. For example, over the Christmas period, I will take time to catch up on whatever the biggest video game hits of the year were, especially the Indie Hits. I like to see how small scale developers are creating these amazing, delightful video game experiences. Because I think there’s a lot that we can learn as product designers from how the best video games are put together.

Jeroen:

Cool. Slowly wrapping up. What is the latest good book you’ve read and why did you choose to read it? We didn’t establish whether you read books but still!

Rahul:

So the latest good book I’ve read is The Art of Game Design by Jesse Schell. I think I mentioned earlier that I used to be a game designer, and that’s actually really important. Because at Superhuman, we built software like it’s a video game because when your product is a game, people don’t just use it, they play it, they find it fun, they tell their friends, they fall in love with it. And The Art Game Design is by far the best book I found on the topic.

Jeroen:

What exactly can you learn from that book you think?

Rahul:

So the book goes into a number of topics. First of all, defining what a game is, the difference between a game and a toy. The difference between game design and gamification, and then lots of different ways to think about the process of game design.

A game, for example, needs a goal. That’s one of the things that differentiates a game from a toy. And those goals have certain properties they need to be rewarding. They need to be actionable, they need to be concrete. Good games are made out of toys. And the book will explain how to construct toys.

Rahul:

For example, a toy should indulge in playful exploration. It should be fun even without the goal. The book will also go into what fun is. And it turns out that fun involves the elements of a pleasant surprise. It’s actually not possible to have fun without the element of a pleasant surprise.

The book will go into many, many other things like what is flow and how do you create it and what makes for good video game controls and what makes for a good video game narrative. And there were so many of these things that we can learn from and bring back into our business software.

Jeroen:

I’m just adding it to my good reads, want to read list. Is it The Art of Game Design, book of lenses by Jesse Schell?

Rahul:

Exactly.

Jeroen:

All right, cool. Then I’ve added it. Final two questions. If you were to start over with Superhuman, it sounds like you kind of got it together, but if there was one thing you could change, what would that be?

Rahul:

I think I would have scaled the team a little bit faster. The only thing that has slowed us down has been not having quite as large of a team as would’ve been ideal. And so that’s the only thing I would’ve changed.

Jeroen:

Is that from the moment you hit product-market fit or even before that?

Rahul:

Probably a year before that.

Jeroen:

A year before that. But how do you know you’re going to hit the product-market fit?

Rahul:

I mean that’s the million-dollar question quite literally in retrospect. It’s easy for me to say that we should have done that. I think the difference is we should have realized we hit it sooner than we did. So we should have scaled faster than we did.

Jeroen:

And if you would give advice to early founders on when you know you’ve hit it, what would you say then?

Rahul:

On how to know whether or not you’ve hit it?

Jeroen:

Yeah, when you’ve hit product-market fit because you say we should have known earlier that we’ve hit product-market fit. How would you see that?

Rahul:

Right. So I’ve written fairly extensively about this and the question that we use to measure this, is how would you feel if you could no longer use Superhuman?

This is a question that is benchmarked, it’s predictive. It predicts success better than the net promoter score. And it turns out that a 40% or more of your respondents would be very disappointed without the product, then you have initial product-market fit and you should put energy into scaling the team and scaling the customer base.

We definitely heard that in the past and we didn’t scale the team as fast enough after hitting that as we should have.

Jeroen:

Yeah. So you’re saying as soon as you see you hit that metric, you should start hiring?

Rahul:

Exactly.

Jeroen:

Cool. Final question. What is the best piece of business advice you ever got?

Rahul:

The best piece of business advice I ever got. Wow. I’ve received a lot of business advice over the years. I’m fortunate to have done so. So I’m sifting through my mind right now. Best business advice.

Jeroen:

The first thing that comes to mind.

Rahul:

So the first thing that comes to mind is from very early when I had landed in San Francisco in the earliest days of Rapportive. I met up with James Lindenbaum, who was the founder and CEO of Heroku at the time. And for those who don’t remember, Heroku was an on-demand hosting platform, specifically for Ruby on Rails.

He said to me, “Be clear in your own mind whether you are aiming for growth of users or growth or revenue because they will take you down two entirely different paths.” And it was excellent advice, which I then immediately ignored, which turned out to be the wrong decision on my part because at Rapportive, we vacillated between chasing growth of users and growth of revenue. And as a result, didn’t do either one of them particularly well. I think had we listened to Jame’s advice, we would have focused on one and then really crushed it.

Jeroen:

Yeah. Thank you again, Rahul, for being on Founder Coffee. It was really great to have you.

Rahul:

Likewise. Thank you for having me.


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Jeroen Corthout

Co-Founder at Salesflare
I'm Co-Founder of Salesflare, the simply powerful CRM for small businesses. I love growth, automating sales, and building beautiful products.