From one founder to another; Rahul Vohra shares his leadership lessons

Oh, my gosh. I think there are as many ways to fail at building a company as there are seconds in a day.

Welcome to Tech Talks, the podcast brought to you by NASH Squared and hosted by myself, David Savage, that's been bringing you the latest thinking from technology leaders for over eight years. On today's show, we're talking to Rahul, the founder and CEO of Superhuman, a startup building the fastest engine email experience in the world. And then we're having a quick chat about the fact that Netflix is touting $900,000 AI jobs amid the Hollywood strikes. And a nod to the fact that this week it was Startup Day across America to get into all of that. Izakesakesh, how are you?

I'm good, thank you. I'm very, very well. How are you?

Yeah, not too bad, not too bad. As I said, Startup Day on America, I think it was actually on Tuesday. So, you know, it's a lovely opportunity to kind of bask in the reflective glory of all of the founders and startup CEOs that we've had on the podcast over time. Our American colleagues in particular gave a shout out to Core 10 leaders Joe Legg and Jeff Galloway. But, yeah, we've had a few recently, so it's worth kind of giving them a shout out. Christine Yen, Paul Roberts, Jeff Grass, Mike Lazaro. Mike Lazaro's from Velvet Sea Ventures. So supporting that ecosystem, what would you say to all those startup founders? Akish?

I'd say, firstly, happy National Startup Day, you know, for Tuesday. Sorry we're a bit late to the party. But also, it's time for travel, to.

Cross information, to travel across the Atlantic, doesn't it?

It does, it does, I think. Yeah. Do you know what? It's. Yeah, it's great that things like this are celebrated about, you know, 10 years ago, there was no such thing, I don't think. And, you know, the fact that these people trailblazers in their own right, industry leaders and almost, you know, I would guess, role models for those that are either venturing or trying to get into the startup game, have an idea, have a product, have a service that they think they, you know, have something that they can really launch for the greater good of the world, for technology, for finance and everything else. Yeah, I think it's great. And keep going. And us as a platform, we're more than happy to have you on again. And for any other budding, I guess, startup leaders reach out to us.

I mean, you do say that 10 years ago, we probably didn't have this day I mean, today is also Northern Territory picnic day. There has been an explosion of days. I don't think we're gonna give a shout out to everyone in the Northern Territory having a picnic. Maybe we should. If you are Northern Territory, that's got like spiders and shit, hasn't it? And snakes.

Yeah. If you, if you're listening, if you're listening to us whilst having a picnic in the Northern Territory. Yeah. Then shout out to you as well. As well as all the other startup.

Leaders, make sure you've got some antiven. Anyway, run back to. Back to something sensible. Today we have got Rahul, the CEO founder of Superhuman. Another fantastic example of a founder in the States, but he's actually British. Went out there almost 15 years ago, actually might be 16 years ago. He's double checked that, but he'll tell us in the interview. So we'll hand over to that. He'll give you the right information and we'll be back afterwards. So today I'm joined by Rahul. Rahul, I was lucky enough to meet you in both Lisbon and in Toronto at Collision. You're the founder and CEO of Superhuman. How are you?

I'm doing great. How are you doing?

Yeah, not too bad, not too bad. And you are a Brit who has found yourself for a large part of your time on the west coast of the U.S. right?

Yeah, it's been 13 years at this point, which is maybe a little bit longer than I intended to stay. I moved out here for my last company, Rapportiv, and here I still am.

As I mentioned, we found each other and started chatting on the conference circuit. Before we dive into a little bit about your background and Superhuman, what have you been talking about? Why have you been going to the conferences in recent months? What topics have you been speaking to people about?

I've covered quite a few different topics. The perennial one, just because it's so hugely important for any startup founder, is how to find and improve product market market fit. For those who aren't familiar, products market fit is the number one reason why startups succeed. The lack of it is of course the number one reason why startups fail. And historically it's always been treated as like this mythical thing that either you have it or you don't. And if you don't, it's a kind of binary miracle between where you are and having it. But actually it doesn't have to be that way. There is an algorithmic way to improve products market fit and there's a very simple metric you can use to measure it that's actually been benchmarked against now thousands of startups, which is a thing that I've spent a lot of time working on, especially coming up with the algorithm or the engine to improve it. And so a lot of my talks cover that. But in addition, it's, you know, really, I've been an entrepreneur my entire adult life and also some of my childhood life, so it's covering the lessons learned along the way.

So look, it stands to reason then that Superhuman has a very clear product market fit. Let's ask what Superhuman do?

Well, Superhuman is the fastest email experience ever made. Our customers get through their inbox about twice as fast as before. They reply to their important emails one to two days sooner, and they save four hours or more every single week. Many of them actually see Inbox zero for the first time in years. It works with your existing Gmail or Office365 account. And as you can imagine, we have customers from every industry and every walk of life.

So look, why this particular problem? Because everyone in the world complains about the tyranny of the inbox, but what led you to being the person thinking, hang on a minute, I can come up with a solution that helps people?

Well, in 2010, I started a company called Rapportiv. We actually built the first Gmail plugin to scale to millions of users. When people emailed you, we showed you what they looked like, where they worked, their recent tweets and links to their social profiles. We grew rapidly and two years later we were acquired by LinkedIn, probably part of why I hung around in California. But 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, and still not working properly offline. On top of this, people were installing plugins like ours reported, but also Boomerang, Mixmax, Clearbit, you name it, they had it. And each plugin took these problems of clutter, memory, CPU performance offline and made all of them dramatically worse. So we decided it is time for change. We imagined an email experience that is blazingly fast, where searches are instantaneous, where every interaction is 100 milliseconds or less. An email experience where you never actually have to touch the mouse, where you could do everything from the keyboard and fly through your inbox. An email experience that just worked offline so you could be productive anywhere. And then an email experience that had the best Gmail plugins but built in natively and which was still somehow subtle, minimal, and Visually gorgeous. And so it's a tall order given all of that. But with that we built Superhuman.

And who's it aimed at? Primarily because it sounds like it would be something that would be a perfect fit for enterprise. But look, and this is probably just my naivety, but I think of Gmail and I think of personal, so I kind of wonder, hey, is it B2C? As a consequence, it's one of those.

Interesting companies that the, you know, the startup or the tech insider would say, is B2C to be. And I think the earliest example of this that folks will remember is Dropbox. People usually started using Dropbox for their own personal need. It's kind of hard to remember this time, but remember when you couldn't just sync files and it was a pain to get things from your one device to another or to your phone and back. People would adopt Dropbox and then what they would find is actually they'd like to share a folder with somebody and it became sort of a small team thing. And of course today Dropbox and many of the companies have a very large enterprise business. And so we're actually following in exactly the same footsteps with the following twist. Superhuman is $30 a month. And so we explicitly have not designed it for the personal use case. It is designed for work. And in terms of who it's designed for, well, very broadly, the people for whom email is work and work is email. And that is a very wide set of people. It's everyone from the freelancer or the entrepreneur who works for themselves, the consultant, through people who work in small companies, through people who work in mid market companies, all the way up to the founders, CEOs and leaders of some of the biggest public technology companies in the world, let's say. So we have, for example, Daniel Ek from Spotify is a user, Max Levchim from a firm and people of that ilk. So it really boils down to this notion that historically email has been regarded as a one size fits all solution. It didn't matter whether you're like the average Gmail user and you receive five emails a day that matter or you're a power user, let's say, and you receive hundreds of emails a day that matter and you send perhaps dozens or maybe a hundred of emails a day that matter. Historically you had to use the same product. And this is obviously absurd. So we looked at that and we understood why it had happened. It happened because historically it was super expensive to build an email client and very scary. You need tens, if not 100 plus million dollars and an extremely talented team. But if you could pull all those ingredients together, you could just about pull it off. And that's what we've done.

Now, according to LinkedIn, Superhuman's been around since 2014. Is that accurate?

Yes, we incorporated in Q1 of 2014, but I didn't really start working on it in earnest until about Q3 or Q4.

So if we come back to your product market fit piece and how to find. I mean, it stands to reason that that's evolved slightly over the years, right? I mean certainly 2020 comes along and the way that we all use our email kind of certainly within our MY organization it rapidly evolved because everyone started using Zoom initially and then teams and then our ways of working have evolved. So I suppose that algorithmic way to find the product market fit and then measure that, you've had to be quite adaptive and I suppose to a degree fluid over the last couple of years as working practices have changed.

Absolutely. But this is true, I think, for any startup, regardless of a worldwide pandemic or not. The thing I point out in all the things I've learned about products market fit, and by the way, if folks listening would love to get into that algorithm, if they just Google how Superhuman built an engine for product market Fit, it's on first round review. You can step through the algorithm there. I point out that it is not a static concept. You don't suddenly achieve products market fit and then you have it, it constantly changes. And I like to quote Andrew Chen, who's a partner at Andreessen Horowitz on this topic. He has a thing called, and pardon my language, the law of shitty metrics or the law of gravity, which is that metrics just go down over time. And you might, that might be depressing. You might think, well, gosh, all this work and everything just gets worse over time. But my point is that is actually a sign of success if tomorrow's users aren't quite as excited perhaps as today's users. Yes, something may be going wrong, but the positive interpretation of that is that you're expanding your audience, that you're tapping into new chasms or caverns of people that you previously didn't have access to. As has famously been said, perhaps you're crossing the chasm. So it actually is normal for your product market fit score, or perhaps even your MPS score to want to come down over time, and it is incumbent upon us as founders to keep those numbers up.

Now you've got a reasonably new feature, Superhuman AI, looking on your blog, on the Website, you were thrilled to announce a whole new suite of AI features, helping you save time, move faster, taking your productivity to a new level. What is that offering the customers that you've got at the moment.

You can now write entire messages, I kid you not, effortlessly, in your own voice and tone. And we think it's the first email AI that is capable of doing it to the degree which it does. You can also reply instantly to any thread, you can summarize long conversations, you can translate languages, and quite a bit more.

And what were the challenges for your team in integrating that technology and making sure that it actually works? Because I suppose lots of people are getting very, very excited about AI at the moment, but implementing it, rolling it out. There are still some challenges for organizations, right? And certainly where they maybe don't have enough data or their own data to do that sufficiently.

So let's wind the clock back to February. I think it was clear at that time you probably felt this as well, that the way we work was probably on the cusp of a huge transformation. We saw that large language models, GPT had stolen all of the limelights. But LLMs more generally could write articles, they could edit text, they could research any topic, they could summarize long documents, they could translate between all languages. And so we were wondering, could LLMs be useful when reading and writing email? And of course, it wasn't just us wondering that. Our customers wrote in in droves. And LLM features rapidly became our top user request, I think eclipsing the next most requested features by several orders of magnitude. So it was clear that the demand was there. It was also clear that the opportunity was here. But we had a ton of questions. How, for example, should we get started? As weird as this may sound, none of us in the company were familiar with the technology and what should we build first? We had so many options to choose from. Our customers had given us so many ideas as well. And even given those two things, how should we prioritize it? I mean, we're a startup, we've been around for a while, but we're still a startup and we still have way more to build than can fit on our roadmap. So those were the key challenges going in, and they weren't easy, but we muscled our way through them.

And if you don't mind me asking them, because I suppose there you own up to an element of ignorance is entirely the wrong word. But, you know, you're stepping into something that's fairly new as a leadership team and you're questioning how you Take use of this technology. As a founder, how do you ensure the business is making the right decisions, has the right leadership? Is that always you? How do you kind of trust those people around you, especially when it's something that is so personal.

On the first point, which is really about disruptive innovation. I remember growing up as a young adult, the transition, I mean, it's so famous. It's the subject of countless business school case studies to the point where we were actually taught it in our computer science degree of Netflix shifting business model from mailing DVDs to streaming and how all encompassing that was at the same time as Blockbuster's demise. And they literally had to cannibalize one business to build the next. Those examples sit heavily with me. Not in kind of a weighty, dreary way, but in kind of a yeah, I have the responsibility to pull that trigger kind of way. It's really hard, I think, for anyone other than the CEO or the founder to make those kind of all in bets or flip the table bets, as it were. And I think that remains. You can delegate a lot and in fact you should delegate as much as you can. But that remains one of the core things the CEO has to be able to pull the trigger on. More generally, how do I ensure that the business has right leadership? Like I said, I think it's all about becoming a lot more comfortable with letting go of the things that maybe you're less good at and then actually using that freedom time to lean into the areas where you can execute at a world class level. For example, I recently hired a world class president, Paul Tessier, and Paul is frankly amazing and has a very wide span of control. So I've now gone from roughly eight direct reports down to two. This is Paul and Kristen, who is our head of people. And together they run the entire business, meaning every person rolls up in one fashion or another to either Paul or Kristen. And so Paul and Kristen are operationally running the business day to day. What that frees me up to do is really lean into product design, certain parts of marketing, making stuff that people want and then helping them realize they want it. I'm a founder at heart. That's what I do best. And it's really freed me up to be founder again, which sounds wholly positive.

But if you don't mind me asking, has it been an easy transition? Has it been easy to go from that many direct reports down to fewer? Obviously you've got time to lean into areas of the business that you're passionate about, but I suppose there Must be some insight there for people who are nervous about doing that. And I suppose that's only a human reaction when you've built something, oh my.

Gosh, it's been tremendously positive and it doesn't always work out that way. You're asking the right questions. I've made my fair share of executive mishires and the failure rate most people don't realize on executive hiring is really high. 30 to 40% of execs don't make it 30% are actually asked to leave or they leave on their own volition within the first 90 days of joining a company. You compare that to a normal hire and it is a shockingly high rate of, I don't want to say failure because it cuts both ways. Let's just call it mismatch. But this time around, I feel like we're onto something special. Paul and I have a very clear chemistry and I think one of the things that I looked for this time and that I very much feel is he like Kristen, they are missionaries, not mercenaries. Meaning, yes, they're motivated by great compensation. But more important than that is the actual mission that Superhuman has to help professionals all around their world essentially self actualize to become more productive, to be more successful, to save those hours a week to free up time to do more and be a better human being. So because they're driven by the mission, we're all so tightly aligned and I think that's been key in helping us achieve the results that we've achieved over the last six months. And they've been great. For example, we've just had over the last few weeks, the best weeks ever.

At the company you mentioned disruptive innovation five minutes or so ago. What advice would you have for those companies who are going through a period of transition or change and they're trying to innovate? What are the missteps? What are the pitfalls to watch out for, to make sure that you don't get derailed and that unfortunately fails?

Oh my gosh. I think there are as many ways to fail at building a company as there are seconds in a day. So off the top of my head, and in no particular order, the classic one is head in the sand, right? That's, oh, streaming is never going to work. Or another famous example is how Steve Ballmer would talk about the iPhone. And I mean, what can I say except don't do that? I mean, treat every competitor with respect, treat every new technology with curiosity. Remember that what got you here might not get you there. And some empires crumble slowly. Some products are extremely sticky. Take a look at Craigslist, for example. Still a massive multi billion dollar business, but some crumble real fast. And you don't want to be that company. You don't want to be RIM, the creators of BlackBerry. So that's one possibly less useful for small startups. If we're talking about small startups that, you know, they don't really have the problem of agility and momentum. It's things like co founder conflict. Make sure that if it's starting to happen, you address it. Make sure that you have clear decision makers within the company. Make sure it's abundantly clear who the CEO is. I often see startups where they haven't made that decision. Make sure you have vesting schedules in place. Sounds obvious, but very occasionally I still see startups that don't bother to do that. And then, you know, somebody leaves in a huffle that has to leave. And now you have a whole bunch of deadweight equity in the company. You definitely don't want that. Make sure you, if you are raising money that you raise from reputable investors and you don't give out worse than market terms because those things can come back to bite you. If you have the luxury of this, make sure you have a lead investor. I would actually say give up that board seat. Make sure that someone has skin in the game so that their career is also, I wouldn't say on the line, but at the very least aligned with the success of your company. Make sure you don't run out of money. That one sounds trite, of course, but we're in a very difficult period for startups. Fundraising beyond the seed or the series A stage is basically impossible. Growth stage rounds aren't happening unless you're an AI company. And so what are the implications of that? Well, assume the last round you raised was the last round you'll ever raise. That means you need to be on a path to break even. And if that's not possible, well, you've probably got to look at doing a layoff or having some really hard discussions internally at the very least, positioning yourself for acquisition. So those are again, in no particular order, both strategic and also tactical bits of advice on how to survive and thrive.

Look, I've got one more question to ask you and I always like trying to kind of get under the hood of someone who's successful. You talk there about fundraising and how difficult it is. You've raised over $100 million several series rounds. You know you've got a huge impact in terms of your customer base. You have been a success, and yet you are still someone who is in this industry. And you must go to these conferences where we meet and go with. With questions. I always think it's interesting to know what questions a successful founder has, what they're looking at, at the world around them.

And clearly, I think for me, most recently, it has been about AI. I mean, I wasn't joking. In February, I had no idea what was going on. I mean, I had. I knew that ChatGPT was huge, right? We were. Everyone had seen it grow to 100 million plus users, but I didn't know how the technology worked, and very few people at Superhuman did. And no one really knew how to integrate it. I just knew that we had to do something. And so I went to a conference. This is a smaller one, 200 or 300 founders, a few VCs, and that was all I was obsessed with. That's all I spoke to people about. And fortunately, there were people at that conference who were experts, who'd been in the field for six months or a year or maybe even longer, and who had launched products or features that integrated large language models. And I would just sit them down and I'd be like, hey, listen, I have no idea what we're doing, and that's okay. Actually, it's kind of fun. It's been a while since, you know, a technology wave swept our company and we didn't know what to do. So talk to me. Let me ask you questions. Let me ask you really basic questions. What would you do if you were in my shoes? What is the first thing that we should build? How? You know, for the scaled companies, sometimes it's like turning the Titanic. What did you do to make the organization actually agile and have momentum? And so I would ask all these questions, and this particular conference lasted about four or five days. It was in a lovely setting. It was in Hawaii. So for as much tension as I was feeling on the business side of things, at least I was sort of relaxed environmentally. And, you know, I left feeling energized and inspired and like, well, yeah, we can do this. And the first thing I did when I got back was like, all right, folks, we're doing this. And here is how.

Look, thank you for spending some time today. Thank you for sharing a little bit about Superhuman with me. And thank you for being so open to the questions around, kind of insight from a founder's piece. Superhuman are building the fastest email experience in the world. And it's interesting because there's a load of articles online that Rahul's written. And he's been very honest about the fact that it's difficult sometimes. And this relates back to our National Startup Day in the States earlier in the week chat before the interview. He was kind of there in the summer of 2017 when waist deep in trying to find a product market fit for his startup, and was doing a load of kind of research around classic blog posts and seminal thought pieces. And I think this is quite interesting because he references the most cited description, Mark Anderson, in 2007. You can always feel when product market fit is not happening, customers aren't quite getting value out the products. Word of mouth isn't spreading, usage isn't growing that fast. Press reviews are kind of blah, sales cycles take too long. I think that piece is really interesting because word of mouth when it comes to startups in particular, that's got to be. So it is so important, isn't it? Because they don't have the marketing budgets, they don't have the clouts to go up against the big kind of players in the space. And if we think back to the pandemic, they're not a startup. But Zoom spread through word of mouth. When you consider that we've all got like teams and hangouts and everything else, it was, it was word of mouth and everyone going, oh, well, I'm using this, that really accelerated that growth.

Yeah, it was. And I think, I think just going back on that point, you know, about sort of usability and experience and, you know, customers feeling it, like if you were to use Zoom, I mean, yeah, if you go back to the pandemic, God, it feels ages ago. But, you know, it wasn't just being used for professional or business usage. You know, I was using Zoom to speak to my parents, speak to my family, you know, running quiz nights, all that sort of malarkey. But I think also at the same time, if you look at the word of mouthpiece, especially within the kind of startup community, I mean, most, you know, FTSE companies, their marketing teams are the size of a startup organization, right? You know, they might have 40, 50, you know, some of the bigger players, you know, more than that, just within their global marketing. And they'll be spread out across digital channels, written stuff, you know, articles, social media, you know, that sort of thing. So I think word of mouth is key, not just for a customer base, but also, I think from when it comes to funding, you know, kind of round, or when it comes to, you know, kind of actually backing financially, if people are, I mean, you Hear about stories and read about stories all the time. Right. Like people, you know, or bankers or something like that, investing into companies and organizations because they have reaped the kind of rewards or reaped the benefits of the organization themselves personally and then they've gone. Actually, you know what, I'm going to, you know, back this company because I had a good experience and I'm sure others like me will as well. So yeah, massive.

There's a couple of really great articles that Rahul's written. We'll share them in the podcast Show Notes. Go have a listen. Obviously in the podcast itself, loads of tips for startups which. Or startup founders rather, which is appropriate given national startup date earlier in the week. There should be some interest around those. I think it's really great that he talks about the fact that you need to let go of what you're less good at and learn to learn what areas you can lean into where you can deliver. And that piece around building a leadership team and trusting them being absolutely key. We've said it for years on this podcast, but it's always worth kind of reminding that that really is something that is a skill and an art to learn that when it's your baby that you've got to realize what you're less good at and letting go.

Yeah, absolutely.

Now, Akish, you work in a talent spotting organization, a recruitment consultancy. Have you picked up the phone yet to Netflix about their 900K? Hang on. Make sure I get this right. Yeah, 900K $AI job listing for myself.

No.

$700,000 per year.

£700,000 pounds sounds good. And I thought a lot of.

That's a lot of money.

I thought it was just the Saudis that were paying crazy money, but obviously not, you know, the Netflix organization is as well. No, I haven't. But also, I mean, wow. I had read of the article. Are we going to put it down in the show notes?

We will.

Yeah, yeah, yeah, yeah, yeah.

It's on the BBC. It's about a week old now actually, if we're being honest. But it's. You might have missed it because it was in the US and Canada section of BBC News.

Yeah, but I mean, unbelievable, right? Like you know what they're paying in order to improve algorithms. I think if you sort of get past the, you know, the stonking salary and sort of what they're looking to do and actually what they're looking to produce. I mean, they're using AI for people like me and you who are Netflix users to, you know, kind of develop better algorithms, show people, you know, programs, films that they're more likely to watch, you know, things like that. So I get it. That's. That's, that's all well and good and very, very, you know, kind of decent to have. Yeah, they're putting a stock load of money in there, aren't they?

I think it's really interesting that, you know, this is in the public eye because actors are in the public eye and there is the Hollywood strike at the moment, and they're talking about the fact that, you know, actors must earn in the US more than $26,470 a year to be eligible for health and insurance benefits. And that might not seem. Seem like a lot because you've obviously got Hollywood stars out on the picket line, many of whom. And millions of dollars for a film or a series. But the reality is the vast majority of actors actually scrape by on very meager earnings per year and they're concerned that algorithms are going to diminish the opportunities for them and devalue their work. And this might feel quite removed from our everyday experience, but actually it's. It's a really good testing ground for policy and for legislation with regards to workers. Right. More generally. And that concern of what automation might do to the workforce at large.

Yeah, no, absolutely. And I think. I think it's away from the sort of the benefit side of things. It's also what it's. I mean, at the moment, yeah, you know, people are kind of out and protesting and sort of, you know, on strike because of that one factor. But what's next, right? Like where. How else is AI going to be used? I mean, you talk about the film industry and that sort of thing, but, you know, where else could it be used? More and more you see things around generative AI, the benefits, you know, how it can improve organizations, how it can improve, you know, people's jobs, work, make things easier, make things more efficient. But also at the same time, acting is. Yeah, it's one of those human things, right. I mean, I don't know, like, we enjoy so many things on screen and it's like, well, you know, what's going to happen? What is the future of that?

So, yeah, so, you know, original ideas, compelling. Television and films are original and they're funny. And I think Brian Cox is at the bottom of that article making exactly that point. Succession, amazing series like, look, AI itself in itself is an incredible transformative technology. I think it was in the news yesterday that the AI has now been approved as successful in screening for breast cancer, like, incredible. But how we use it and being intentional about how we use it and what the knock on effects might be for everyday people is also really important.

Yeah, yeah. I feel like we just need to write some sort of charter to only use it for its good and benefit. Yeah, that ain't gonna happen though, is it? Because apparently, you know, there's all kinds of.

We don't need it to create TV for. No, we do need to stop cancer.

We don't need the ending of succession to be, you know, kind of drafted out and written out by AI and you know, that sort of thing. We need it to, yeah, fight cancer, fight diseases, you know, help better the world, help increase sustainability. But yeah, leave the acting to the the names in Hollywood that know how to do it.

Thank you for joining us on today's show, Rahul. Thank you for being our guest. To all American founders out there, as we say, or as we said rather have a lovely. Or have. We hope you had a lovely national Startup Day. And if you're having a picnic in the Northern Territory today, maybe wear some long socks.