Superhuman 2.0: The AI edge, top productivity hacks, and the future of email | E2002

4 Sep 2024 · 1 h 14 min

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Podcast Episode Summary: Superhuman 2.0: The AI Edge, Top Productivity Hacks, and the Future of Email | E2002

Podcast Information

  • Title: This Week in Startups
  • Host: Jason Calacanis
  • Guest: Rahul Vohra, Founder of Superhuman
  • Description: Jason Calacanis discusses startups, technology, markets, and interviews notable entrepreneurs and investors.

Episode Overview In this episode, Jason Calacanis interviews Rahul Vohra from Superhuman, focusing on the evolution of Superhuman, its innovative onboarding strategy, and the application of AI in improving productivity and email management. They explore new features in Superhuman 2.0, including AI integrations and collaborative functionalities.

Key Discussions

Guest Introduction

  • Rahul Vohra discusses his background and previous startup, Reportive, which focused on enhancing Gmail's user experience by integrating social profiles.

Evolution and Challenges of Superhuman (Timestamps: 2:00 - 6:33)

  • Superhuman was born from a realization that existing email systems were becoming slower and more cluttered.
  • The original vision was to create a fast, user-friendly email experience that appealed particularly to power users who value their time.
  • Early challenges included skepticism from investors about building a paid email service competing with free offerings like Gmail.

Onboarding Strategy (Timestamp

11:17)

  • Superhuman’s unique onboarding process involves a 30-minute interview to filter potential users and ensure they understand how to leverage the product effectively.
  • This approach helps in identifying serious users who will benefit from the product, avoiding "tire kickers."

New Features in Superhuman 2.0 (Timestamps: 20:55 - 27:37)

  • Introduction of multiplayer email, allowing teams to collaborate on email threads in real-time, enhancing communication and efficiency.
  • Demonstration of Superhuman's live AI features, which assist users in drafting, summarizing, and managing emails.

AI's Role in Team Management and Productivity (Timestamps: 52:07 - 58:27)

  • Discussion on the impact of AI on workflow and team productivity, emphasizing the significance of AI tools in reducing time spent on repetitive tasks.
  • Superhuman's Ask AI feature enables users to ask specific questions about their emails, providing quick and relevant responses.

Future of Email and AI Integration (Timestamps: 1:07:26)

  • Predictions on the future role of AI in email management, hinting at capabilities like auto-scheduling meetings and drafting replies tailored to the user's unique voice.
  • Emphasis on the necessity for companies to adapt to AI to maintain productivity and efficiency in the workplace.

Key Takeaways

  • User-Centric Design: Superhuman's success lies in understanding its ideal customer profile and tailoring its services to meet the needs of power users.
  • Innovative Onboarding: The human onboarding approach effectively enhances user engagement and product understanding, ensuring that users maximize their experience with Superhuman.
  • AI Integration: AI features are pivotal in transforming email management, offering capabilities that streamline tasks and increase productivity.
  • Future Outlook: Continued investment in AI technology is essential for the evolution of email tools, making them more collaborative and efficient.

Additional Resources

  • Superhuman Website: [superhuman.com](https://superhuman.com)
  • NetSuite Guide to AI and Machine Learning: [netsuite.com/twist](https://www.netsuite.com/twist)
  • Lemon.io for Hiring Developers: [lemon.io/twist](https://lemon.io/twist)
  • AssemblyAI for Voice Data Services: [assemblyai.com/twist](https://www.assemblyai.com/twist)

Conclusion This episode highlights how Superhuman is not just enhancing email but redefining productivity through innovative use of AI and user-centric design. The discussions serve as a valuable insight for founders and startups looking to leverage technology for improved team management and operational efficiency.

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Transcript

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0:00okay so i'm just gonna go ahead and hit question mark and i'm gonna say find me the top 10 most positive customer responses to the best customer responses to the best Haystack combination information synthesis stuff. All I have to do is hit copy, come here, hit paste. The formatting is perfect. It is done. It is done. This Week in Startups is brought to you by NetSuite. The number one cloud financial system that unifies accounting, financial management, inventory, and HR into a single platform. Giving you one source of truth. Download the CFO's Guide to AI and Machine Learning today. Visit netsuite.com slash twist.

1:02Lemon.io Hire pre-vetted remote developers. Get 15 % off your first four weeks of developer time at lemon.io slash twist. And Assembly AI. Get maximum value from voice data with Assembly AI. Build powerful products and features for your end users on the industry's leading speech-to-text models. get 100 free hours to start building at assemblyai.com slash twist hey everybody welcome back to this week in startups one of the great joys of my life uh having been an angel investor now a seed investor is that i get to meet um entrepreneurs at the start of their careers and one of the great entrepreneurs i've been lucky enough to work with over two startups is raul he started a company called reportive and i was a fan of this little toolbar that helped people using their gmail uh figure out who's emailing them by clicking on a link and seeing their twitter and their linkedin profiles easy peasy lemon squeezy was the you know simplest most elegant piece of software i had used at the time but man was it a time saver and it grew like a wildfire was sold to linkedin and i told my pal raul i'm absolutely in favor of you selling this i think he maybe he wanted to keep going his founders didn't a lot of stories there uh they said just promise me when you leave linkedin i get to be the first investor in your next startup and uh i think i'm one of the first you know i don't think he's it's a little controversial because there's another uh super fan of raul's who also likes to be considered the first and he's a friend of mine darmesh from hubspot uh welcome back to this week in startups roe vora from superhuman how are you doing pal doing great excited to be back i think this is my third time third time on the show when you hit five we give you a jacket and uh but people don't know that you've also done at least i don't know five or ten times for me talks with our founders and we're also very thankful for that um the reason i wanted to have on the pod is you know i'm a super fan of superhuman which is an email product that you pitched to me on a sunday at my house over bagels and i always recount the story to people uh to you know when i talk about uber and Robinhood and Calm amongst the greatest hits we've had.

3:21And I think Superhuman will be right there with it in terms of returns for RLPs, but also in terms of just greatness of a product. Your pitch made no sense. And when a pitch makes no sense, that's when I get excited. When I'm confused after having invested in 400 companies and taken 10 ,000 million of founders, I know there's something there. Do you remember the original pitch and that Sunday? I probably said something along the lines of, Jason, I'm going to build the fastest email experience in the world, and then we're going to charge people$30 a month for it. And you probably did a spit take with your bagel and were like, Rahul, that's not going to work.

3:59No one's going to pay for this thing that historically has been free. And I probably said something brash along the lines of, Jason, trust me, they will. Yeah. And it was exactly like that. and i the the heat check i gave you was okay so you want to take on um gmail which is free and you want to make it faster than the company who makes gmail google which has an obsession with speed and the largest at that time computer network in the world and the largest number of engineers focused on speed in the world and you think you can beat them uh and uh you were like yeah and then you explained to me what and it was a really good explanation which is gmail is servicing billions of users they need to build it to the average user and because it's free like they're not gonna you know hemorrhage money making it faster um and that you only needed to get one percent of email users who care about and this is where ideal customer profile comes in you know for anybody uh like darmesh from hubspot who i think just recently tweeted a you know um a great testimonial of superhuman anybody who's in their email box for more than an hour to a day which would be a power user which is probably the top 10 of users and whose time is worth more but worth a lot of money on a per hour basis would pay any amount of money to get through that goddamn inbox faster that was the key insight and that's why a dollar a day is farcical to a ceo a management team and anybody making over a hundred thousand dollars a year a dollar a day is nothing if they can gain back but 10 minutes per day and that's when i fell in love with your concept when you deployed that concept into the real world and you had this concept about the ideal customer profile and we'll talk about superhuman 2.0 and all these new features powered by ai but i just want to go back in history when you brought it to market what did you learn and how did your vision manifest itself when it faced the reality of users?

6:04Yeah, gosh, well, that's kind of quite an evolution. I think like most founders, I started with a gut sense that something was wrong with Gmail. And I lived it myself. I mean, you mentioned Reportive at the top of the show. I was a CEO back then before I was selling the company to LinkedIn. in. And I remember managing my email with Reportive, but also with Boomerang, with other similar browser extensions that we had at the time. And bizarrely, Gmail was just getting worse every single year. It was becoming slower, more cluttered. It still wasn't working properly offline. It turns out that at the time, this is probably still the case, that Gmail inside of Chrome was the single biggest reason your laptop would run out of battery.

6:45It's so energy inefficient. And on top of this, people were installing plugins. And I thought, how ridiculous, but also in a weird way, how fortuitous we'd created the perfect conditions to go and build an even bigger company. That's because Reported was the first Gmail extension to scale to millions of users. Before then, it was insane. I mean, nowadays, we take it for granted. Grammarly and Honey, two major browser extension success stories. But back then, this is 2010, no one believed you could build a business with a browser extension. So we showed people that you could, and there were lots of products, and the whole ecosystem was falling apart.

7:23So I thought to myself, okay, there has to be a better way. What would email look like if it was, in a sense, vertically integrated, like if Apple were to build it? If you didn't have to add a bunch of browser extensions, if it was blazingly fast, searches were instantaneous, everything happened immediately. and if all of that just worked offline. So that was the original idea for Superhuman, and it was really a gut sense that I had. But then I did something that I think too few founders do, which I know you'll appreciate. In that first year, I spoke to about 700 people, that's roughly two per day.

7:58And you might think, well, that's kind of a lot. How did you do that efficiently? Actually, very easily. I put up superhuman.com. It sucked, like a bit of blurb, really not great design, whatever, just stating the vision. And whenever anybody emailed in, they got an automated response back from me. Now, it didn't look automatic, but it went something along the lines of thank you for signing up. We're busy building the best email experience we can possibly imagine. Two questions. What do you use for email today? And what do you hate about it? Two very powerful questions. I think you can use this for any product, any service, any market.

8:32And invariably, people would get back and say, I use Gmail. Some of them were using third-party products, but they would all say email takes too long. And when I would dig in, they'd be like, it takes too long. It's too slow. I'm frustrated. I don't like how long I spend in it. So there was like this mix of ideas here. At the same time, I read this amazing book. I think it's called Positioning the Battle for Your Mind. And I realized that because this is a market dominated by incumbents. I needed to find a positioning that everyone would remember. It might be weird, it might be kooky, but speed is something that everybody can remember.

9:10And that was the first time where I was like, okay, there might be something here. And then finally, I knew we had it when I did the cocktail party test. You may have heard of this. Ed Sim, a dear friend of ours at both starts shared the name with me. The idea is go to a cocktail party, kind of look, watch people pitching your product to other people and see what they say. And time after time again, I'd hear people, founders and managers, but also salespeople and folks in BD and whatnot say, superhuman, it's really fucking fast. And at that point, I knew I had it. It had become like this viral idea.

9:50It was so easy to remember, so hard to dislodge, so easy to own because no other product was owning that space, that we just ran straight after it. Okay, are you worried that your startup is the only company out there that's not building with AI features? Well, if your company records or collects any voice data, I've got a secret weapon for you. Assembly AI has the AI models you need to turn that data into new features that your users are going to love. So don't fall behind. Put this incredible technology you to work for you. Whether it's podcasting, audiobooks, meetings, especially the virtual ones, and all the videos that people are constantly uploading, we're producing and consuming more voice data than ever before.

10:33If your startup is building a product that uses voice data, you'd need to check out Assembly AI. Assembly AI builds speech to text AI models that can turn your voice data into new product capabilities. All you need is voice data and a few lines of code. For example, VEAT.io makes video editing tools that generate captions. That's what you see on all the This Week in Startups clips. That wouldn't be possible without Assembly AI crunching the audio data. Assembly AI's speech-to-text models are simple, accurate, and fast, and they've got the industry's lowest word error rate, 30 % fewer hallucinations.

11:10If you want to put your audio data to work and build powerful AI experiences for your customers, head to assemblyai.com slash twist and get 100 hours for free. and join over 200 ,000 developers who are building amazing apps with voice data. Go to assemblyai.com slash twist today. It is amazing how this focus on a certain set of users, not all users, but a certain set of users can unlock features that maybe the masses just don't care about and are unwilling to pay for, but that a certain group of people covet. And so, you know, when you get the product out there, it's gorgeous. I think two things led me to believe that this would be a fantastic investment.

11:54And in fact, the fund you're in, I think we invested$500 ,000. The biggest bet we had made to date in that fund, this was a$10 million fund. And you have your own fund and you understand when you have a$10 million fund, 5 % of the fund going into one startup is a big bet. And two things occurred to me watching your story over the years. One, people have copied your design and your concept. So I have been pitched no less than 50 times on we're superhuman for calendar, superhuman for CRM, superhuman for Slack, whatever it is. And it's actually what they mean by that. When you say superhuman for, in a human's mind, what that means is, or in our industry, it's going to be elegant powerful and for power users it's actually like an aesthetic now um which i think is like a very big compliment now that alone doesn't mean you're going to be successful but it does mean something that the the the founding community is so enamored by what you built the second piece that i thought is very interesting is when i talked to founders and again we have 20 000 people apply for funding from launch now and we do 100 per year so since we invested in you 10 years ago or so i don't know maybe nine years ago i think it was like yeah 2015 or something 2015 yeah yeah um you know since then um many folks have come to us and said i say okay yeah you know what's your go-to market strategy they say oh we're gonna do super we're gonna superhuman it and we're just gonna do what superhuman does we do what raul does his playbook and what they mean by that is we're only going to uh onboard people with a 30 minute interview So let's pause there and talk about that innovation.

13:44How did you come up with that? And then how have you altered, evolved, or not that strategy? And founders who are listening, this is a super profound one. Right. So this was way back when. I believe we started onboarding people in 20, let me see if I get this right, probably the end of 2017, maybe the end of 2018, more likely 17. In fact, I think the very first paying customer might be our good friend, both of ours, Austin Peter Smith. He was, yes. Austin Smith, now Peter Smith, was your first interview, correct? Yeah, yeah. So why did we do it in person? Okay. There is this rule of thumb. And I read this first in a really great book, Traction by Gabrielle Weinberg, Justin Mez, where they say that as a startup, you should aim to spend roughly 50 % of your resources on product but 50 % of your resources on growth.

14:42And I think in general, that's pretty good advice, because most founders forget the latter, and they just obsess about product all day long. However, the size of the problem that we were taking on was too large to do that. Today, it's relatively easy for us to hire excellent engineers, we have a phenomenal team. But back then, in the sort of 2014 to 2017 era, I mean, Jason, it was tough. People were like, Like, wait, you're building what? Okay, you have all these great investors, but you're building what? That kind of doesn't make sense. There was some skepticism, as one might expect. So it was difficult to build a large engineering team.

15:19And in any case, we didn't want to spend too much money. I therefore always have to choose for each marginal engineering hour, do I put that into making the product better and into unlocking products market fits more? Or do I put that into things like activation and building a first-time user experience? And I just remember thinking to myself, well, what if the product is wrong? What if we have to change something? Every engineering hour we spend on growth, we're not spending on products, and boy, do we have a lot of product to build. Now, of course, this was a pretty Zerpy era, so it was relatively easy to raise dollars, but it was hard to get engineering hours.

15:55What does a good entrepreneur do? They spark an arbitrage. and i was like okay i'm going to raise dollars i'm going to hire an onboarding team and i'm going to put the meager engineering hours i have into improving the product what we're going to do is we're going to substitute the software onboarding with a human onboarding so that's where the idea initially came out of now when we started doing it of course we look at the metrics we are not data driven but we're data informed and we were looking at things like bug rates and virality and net promoter score and the product market fit score which i've spoken about a lot and all of those were through the route and initially i was like okay is it just because i'm doing the onboarding or is it because my brother then head of growth garb is doing the onboarding or it's because the onboarders are super charismatic and we started disproving these negative theories one by one until we were just like wow the onboarding really does work now the other aspect of why founders might want to consider this, perhaps the most important aspect, is you get rid of the tire kickers.

17:02Especially if your product is something like superhuman, where it's designed to make you more productive. It's designed to save you time. There's a very real ROI. Most of our customers save four hours or more every single week. They're applying to emails 12 hours sooner. They're getting through their inbox prices fast. What you don't want are people who don't value that thing and it's very very easy with email to just get like tens of thousands of people signing up because everybody has an email address so the the pool of potential customers is everybody but the ideal customer profile is somebody who is going to learn the product who knows quick keys and who's going to leverage it and if you're a casual email user you You know, my mom uses email.

17:47She, you know, gets a couple a day. She's not taking the time in all likelihood to learn the quickies. Once you're getting a hundred emails a day, you're learning the quickies. You want to get through stuff fast. And this was, I think, you know, a very big unlock for me in evaluating products as an investor, which is like, who is this for exactly? And does the founder understand who their actual customer is? And I think this was just such a great unlock for you in terms of your career trajectory. Again, we are so lucky to have invested in some great founders across two companies. I was the first investor in Thumbtack, and I'm the first investor in Athena.

18:27Wow. First investor in LinkedIn. I'm sorry, purportive. First, I'm going to say I'm first, but I know Darmesh is going to get upset. But amongst the first, in the first group that got into Superhuman. and what the founder learns across companies is so critical. Reportive was, you know, ostensibly for everybody, but the people who actually got value from it were salespeople or executives or hiring people. Like those two or three people who are going to look up the LinkedIn, look up the Twitter handle of 100 % of people who email them, right? Like that's not everybody, am I correct? I'll share something that's going to blow your mind and we should have sold this company for a lot more.

19:09it's been so long i don't think anyone will care it turns out which is what i told you i was so heartbroken i tell everybody when you made me four times my money or five times my money it was the worst day of my life well okay okay it was a precarious situation as the classic example of you know leaning on one api which go away at any any point in time we had 10 percent of linkedin's daily active users on reported imagine that a billion dollar company that had just gone multi-billion dollar company that had just gone public we had 10 of their daily active users and i had no idea it's crazy here's the thing it people tell me also like i sold weblogs inc which we sold for 30 million dollars 18 20 months after we started oh my god you're an idiot you sold it too early to people don't remember the industry was very different at that time 20 years maybe yeah almost 20 years ago when we sold which was you know there was no such thing as secondary I was negative$20 ,000 when Brian Alvey and I sold and Ryan and Peter from Engadget, like when we sold that company, like I was broke, broke.

20:17There was no secondary opportunity. When you sold, you know, this idea that like there was a sword that's going to come down on your head and just kill the business because an API is going to go bing. And then there's, it's not like you had a war chest like you do now and the reputation. And you had co-founders, people want to get off the train, so many different things. But that's such a great fire. It's such a great regret to put in a founder's head. Because then when you do the next one, you're like, you know what? This time we're going for gold. We're not taking the bronze. We're not taking a silver.

20:51We're going to go for the gold. Now, if we happen to go for the gold and hit silver or bronze, it's not the end of the world. but you know and back in that day you know sometimes somebody offers you a bronze medal a silver medal and you're like i gotta take it for my family etc um let's talk about superhuman 2.0 you've been at this for a long time people don't know the numbers i do but you know let's just say this is a significant business now um it's you know it's got real revenue real customer base and there were a couple things i kept hounding you on and you are methodical i'm not gonna say slow but methodical in releasing products so you you really try to get it right the first time i very much appreciate that but i was just like i need multiplayer mode i need team snippets i'm like gosh almighty you know i got these you know um people on my team i'm writing snippets for people who don't know i have to send the same email over and over and over again which is thanks for emailing me we don't take pictures from the podcast thanks for emailing me i wish you great success in your startup however we don't invest in your category we wish you tremendous success here's some resources for you and then i need to give those snippets and i want crystal clear communication from our organization as it grew to 21 people that they use the same language because you know you don't want to say things you want to say things consistently so i really need to group snippets and then i was like you know i'm taking screenshots of superhuman putting it into slack and having conversations around threads and then some person on my team responds i literally just had this happen somebody responded and said hey you know i think this founder has ugly baby syndrome oh gosh i mean this happened to me this month bro and i was like the founder left the founder on the cc list and you know i really like this founder and they were referring to ugly and i i was like oh my god this is like this is literally a researcher in their first year and by ugly baby he meant his product right and so yeah i get it still i had asked like one question or two questions that were you know a little challenging on the call hey how do you think about this how do you think about the design you know and then this researcher worked for me in year one and i'm like do i have to fire this guy or not and he was so smart my researcher he called the founder on the phone he said i'm probably going to get fired for sending an email i just want to let you know i'm incredibly sorry that was a terrible way to phrase it i know that it's year one for your startup i respect you and i know that design was maybe something you're working on so he smoothed it over with the founder and then it got to me and he's like just you know i called the founder but this could have easily been avoided had this person been on superhuman who had not yet installed it or not yet used it and that might have been on my team's fault with the new features so can we go over those multiplayer mode features and then the ai features and just talk about how you think about launching new features.

23:48Absolutely. And I'll do the craziest of things, and I'll attempt a live demo. Let's hope. Well, I can. Open AI and fireworks this afternoon. Go down. Yeah, so we, you know, it's funny. I was actually just looking at the notes. For the first time I was on the pod, this was October 23, 2018. It's kind of insane. and you asked me, what does the future of email look like? And I said three things, or I said a lot of things, but including, you'll see a lot more AI and machine learning. You'll see your emails automatically written for you. I'm reading this out now. Number two, you'll see a lot more tooling around collaboration, multiplayer, shared conversations, assignment, shared draft, and so on.

24:33And number three, you'll see emails themselves get shorter and shorter. Email clients will themselves turn into messaging apps. That was 2018. And so I had this a very happy moment this morning when i was preparing for this call where i was like oh wow that was true it took a while but like that's actually what's happening right now which is kind of cool okay i mean it is did you run it through did you run that episode through a an ai to get the summary or did you just listen to it no no i as you know i fastidiously prepare for everything so i was just looking at the notes from how many years ago it's really interesting you know claude does a really nice job with summarizing i think youtube videos or videos So I've gotten my, you just start thinking about the power of AI.

25:15One of the great powers of AI, if you look at podcast production, we have a new company we invested in, Podcast AI. And the founder, Edward, reminds me a lot of you because he's customer obsessed. He figured out a way to not only do transcripts, which is kind of table stakes now, but it understands the context of the conversation and then writes show notes for us of all the moments in the show. and then you can highlight it and make a clip and make an audio or video clip putting that all aside he then was like you know what would be good for us to know what's happening in the news and then write a docket which is you know what i call our um you know our our prepared document for what we're going to talk about if you could actually have it tell it what sources of news you cover you know if you're a biotech company here's a 10 biotechs and it actually suggested stories and made the docket so essentially ai is taking what producers do in podcasting and basically starting them on second base maybe even third base so you just have to run home steal home um and it just means either you can make better production or lower your costs by having less so it's really actually happening in text audio and knowledge work it's actually happening now right now startups have to do more with less.

26:29We all know that. And founders have to be smart with how they deploy capital. Investors are very tuned in to being capital efficient. So if you need great tech talent, but you don't have the time to interview dozens and dozens and dozens of candidates, you need to check out Lemon.io. They have thousands of on-demand developers to choose from, and these devs are vetted and their experience. And most of all, they're results oriented. They're going to get you the result you're looking for, they're not going to leave you hanging. And guess what? They charge competitive rates. Great developers can be incredibly hard to find.

27:03We all know that. And when you do find them, it can be hard to integrate them into your team. But Lemon.io will handle all of that for you. Startups choose Lemon.io because they only offer handpicked developers with three or more years of experience and strong portfolios. In fact, only 1 % of candidates who apply get in. And if something ever goes wrong, Lemon.io will get you a replacement ASAP. A couple of launch founders have worked with lemon.io and they've had great experiences. So here's your call to action. Go to lemon.io slash twist to find your perfect developer or tech team in 48 hours or less.

27:38And twist listeners get 15 % off their first four weeks. Stop burning money, hire developers smarter, visit lemon.io slash twist. So yeah, let's do the live demo. I just I love a good demo. Let's have a back and forth discussion here. A show don't tell always one of my favorite rules of podcasting if you can't if you're listening right now go to youtube.com and just search for this week in startups and you can find the video or use spotify which has video the context here is we had a major inflection over the course of the last year and as you know as an investor we are being pulled up market into the enterprise we recently closed a a very large tier one strategy consulting firm i can't say which one uh our largest deployments have grown from small startups to teams of several thousand and we're now serving industries that go well beyond just technology which is the largest number of users or ballpark users with one installation one domain name you know as it were one organization have you gotten past a thousand in anybody yeah in the region of two to three thousand i had no idea that's so extraordinary to be that far up i didn't i thought you were going to be sub 1000 for a while that's great We were just until a few months ago, but over the last year, enterprises really just started clicking, and we've more than doubled the rate at which we welcome these new users.

28:58Now, as we grew and as we've grown to serve these larger companies, we noticed this fundamental problem with email, the one that you just outlined, which is that basically every other piece of software that we use, think Slack, Figma, Notion, Loom, that's now all collaborative by default. And even though more people use email than any other tool, for folks who don't know, a billion professionals use email for three hours every single day. Email is not yet collaborative. And the problem is so ingrained that we take it for granted. So for example, if you want to share that email with your team, you could have a meeting, but your team probably isn't free.

29:32You could paste a screenshot into Slack or Microsoft Teams, but now the conversation is in two separate places. And you could forward or BCC, but now you have to remember to do that for every single email that you send or receive. And there's always the risk, that somebody does what your analyst did and says something regrettable externally. So what do we do? Well, three things. We imagined the core email experience to be multiplayer by default. Number one, you can now share a live view of any email conversation with your team. There's no need to ask for meetings. There's no need to pay screenshots.

30:02There's no need to repeatedly forward in BCC. Number two, your team can then follow along either in Superhuman or via a link. They don't even need to be using Superhuman. I'll share an example of this with you in a minute. And number three, you and your team can then comment directly on the conversation. And there's no risk that those conversations actually leak. Let's take a look. I'm going to go ahead and share my screen. Okay. So here we are bravado plus superhuman for sales. And you're having a conversation here. I see that. And I love this new feature, by the way, under the subject line, there is a little summary in bullet points.

30:36This, I didn't know you were going to do this, but this has saved me when I have to catch up on some crazy thread. And here, in the summary, it says, Sahil and Superhuman discuss podcast details and scheduling. Sahil offers 20 % discount on sponsorship. Superhuman requests further re-education reduction. Superhuman signs and returns sponsorship paperwork. Podcast recording set for 7, 23, 10 a.m. Sahil requests expedited paperwork return. And it has a thumbs up, thumbs down. These summaries are pretty accurate, huh? Super accurate. And I love these. And you'll notice that I'm just going to quickly scroll up and down.

31:11this is a long ass email there is a lot going on here about 20 emails back and forth yeah imagine you suddenly got added to this and boom that's all you need to know so genius should point out uh we love sahil i checked with him this morning i have his full permission and his blessing to share this if you haven't seen bravado they're an amazing community of sales people go check them out we recently launched superhuman for sales uh let me just show you what that is it's a version of superhuman that is designed for sales people it does all kinds of incredible things and we need to design extra for that or is it just included in my dollar a month uh it is let's we also just launched new pricing plans so if you're paying monthly it's 40 a month this comes with superhuman for sales uh yearly it's still very similar to three dollars a month so 400 bucks a year and if i save one hour per person per month on an average salary you know that would be 40 an hour times 2 000 hours a year 80 000 so anybody making above 80 000 a year who saves one hour your break even already and less mistakes costly mistakes so you know on a team of 20 400 a year you start doing the math 8 000 no brainer for our organization but you know you have to do your own back of the envelope math for your organization or or what many of our customers do is we help you do the math right like it is a a very classic motion what will come in will help you figure out the roi calculation most customers are actually saving four hours per user per week or more so the roi of buying superhuman is well north of 20x per year okay back to this example we had to come up with a go-to-market for superhuman for sales I thought of Bravado as an amazing community that we could advertise to, so I ping Sahil, and we start to get the conversation going.

33:02Now, this is just between me and Seyon, or Se, who is our head of marketing. We've got some back and forth going on here, and you can see here, he's like, okay, we have 80 ,000 people, which plenty of VPs, CROs, 300 ,000 account executives, is like such a great opportunity and he says fifty thousand dollars okay now it's the time where we have to have the conversation internally what you might do historically at this point is paste it into slack that's what i would know no one else can yeah and which has its problems right like people can't see previous emails they won't be able to see future emails the conversation is now in two separate places or what many organizations do is they start repeatedly forwarding and bcc but what we do here is say starts sharing the thread this shares all the previous emails and all future emails with the people he is going to share it with he says is this something you'd be up for it seems like a good idea it's going to drive mqls and he adds my ea megan he adds the head of products marketing for superhuman for sales spencer and the head of products management for superhuman for sales chris which is amazing because they now get to see not only all the previous emails as opposed to one weird forwarded reverse chronological mail but also all future emails as well uh sahil bless his heart then pings because you know we we sort of sat on this for two days uh we buy some more time and now we start having an internal conversation about scheduling it's like okay you know rahul's going to be pretty busy he's going to be out of country i opine i'm like look this is the first time i'm talking about this let's get this really really great how are we thinking about roi how are we thinking about timing should we do one big launch or should we do two multiple launches spencer recommends we do it i'm still pushing on the roi so he'll it's like yo what's going on let's get this done so there's like these two parallel conversations here there's the internal conversation there's the external one and it's really nice on a design basis for those of you not watching is it visually looks different the email looks like one thread and then the square boxes although i'd like to see them with a little background color maybe like if i could if you tinted them a little yellow or something i don't you know this is a very 1.0 product here but even for me visually i'm so concerned it's like this little fear going on is there's two threads and never the two shall meet because we might say something like hey this founder just doesn't seem driven enough or whatever if somebody says hey i don't think this founder is going to figure it out or i don't think they can compete with you know superhuman or something oh my god this could be a disaster so how do you think about the design there when you were designing this it was exactly that this is a different um i know not everyone can see but the comments are a different width to the emails they look very different and that is to drive home the point that uh unfortunately the very honest mistake that your analyst made is not going to be made again happens every day happens every day it's so embarrassing and people shouldn't we should not be let down by our software in that way so that was a core part behind this and you can see here there's a very happy ending we get the schedule uh we get the discounts or we get it done it then turns into a classic scheduling email we want to spare uh our good friend sahil all of all of the nonsense with my out of office and going to europe and back and forth and it just gets done and this is something that now is in the hands of our customers we're getting feedback like we're closing deals that we want to close before we're closing deals faster than we've closed than before everyone is way more comfortable and here's something really cool you don't even have to be in superhuman so i could click up here or i hit command s this is the share conversation uh dialogue i'm just going to hit copy link and then come over to a text message that jason this is our text message back and forth i'm just going to text this to you you can now tap this on your phone if you were so inclined and you would get that whole full conversation you'd see what emails see what of comments you could then input on the conversation yeah and uh that would then appear here and if i'm not on your team it would not do it so if somebody got that url and they're not part of the team space doesn't work right so it actually does so this is designed for the use case where you maybe want to collaborate with your first investor like yourself or you want to collaborate with a vendor or you want to collaborate with your pr agency or whatever it may be uh and then in the future we're going to be building controls on turning off those links turning on those links and so on got it yeah that's so you know it's kind of like when you share a document in google docs you could make a public link you could make a organization link etc i do think just to punch up here uh so investor giving unsolicited feedback you can throw it in the garbage um making it a different font or a slightly different background color would make this really interesting.

37:53And then the next piece I'm trying to figure out, and I'm sure you have this on the roadmap is, I want to be able to pull up all the internal conversation. So I have an inbox. But I want an internal inbox, which would be just show me all the threads that are going on in the organization. You know, outside of my inbox, does that make sense? I don't know what this call. We actually, we do have something very close to that already. What you want to do is hit command a split inbox settings and you can go here the split i've got loads as you can see here yeah the one that you want is team so go ahead and turn on team that'll be from launch.co to me or whatever url you're using it on yeah and it's not all the email internally because that turns out to be way too much but it's all the email internally addressed to you which as a leader you want to respond to very quickly because ultimately we're the folks who hold our organizations back when we don't reply quickly.

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40:07Yeah, for me, you know, one of the things I've been thinking about a lot is, as AI grows, I need to know where these conversations are, how to address them. So on an API basis, as an example, we have a slack room for deliberating follow on investments, we have a slack room for deliberating primary investments, making that first investment. So the example would be, hey, you know, making that first investment, we have one slack room for that, then we have another room for oh superhumans doing their next round should we take our prorata should we go super prorata should we be selling in secondary or whatever um and i'm obsessed with having on notion some information and then in slack having one and we're just it's these conversations are so valuable also we are recording um some of our deliberations and discussions on zoom taking the transcript putting the transcript and the original video onto zoom why i don't have the original deliberation for uh reportive uber robin hood com um anywhere it occurred in a conference room with three people when the firm was just two or three people me ashley and jackie just like i'm like hey i'm thinking about investing in this company and they asked me a couple questions and then it's over now you know i i in some ways i hate remote work because you know we miss the collisions and the in-person stuff but having the digital trail of everything man i would love to have that conversation some of those conversations to pull it up and say what can we learn here on passing on twitter and saying yes to uber you know like just and and now we are doing that and so So that was one of the big discussions we had was, how do we get this, these conversations out of superhuman and have them in some repository?

42:00So tell me how you think about that APIs. And I'm sure with enterprises, they're like, I need to know what our employees are talking about. If you're in finance, as an example, like we are, we have to tell our employees, any conversations you have, we have access to, we are storing forever. Don't ever say anything. you know in zoom slack superhuman email anywhere that is inappropriate it's all you know in a finance company not your content it's our content for all time we could be subpoenaed all that kind of stuff whereas other organizations might be like yeah your dms are not looked at you know whatever we have to look at people's dms in an organization we have to look at this side conversation if they were to say something or god forbid you know share information they're not supposed to finance organizations held to a much higher standard obviously so how do you think about that yeah uh well i mean first of all just my my psa uh you should just assume that when you work for a company your company communications belong to the company even if the company says we're not going to look at your dms they may not want to but they may be asked by the government to yeah and they can't say well we don't want it like they then have to do it so um just don't don't say anything stupid folks like keep it real um we don't really play in that space i mean there are tools i think this is why uber deletes everything after was it six months something like that right yeah i think a lot of organizations are moving to don't keep stuff yeah it's just a liability yet your data is our liability we don't want it here exactly smart move yeah yeah so we don't play in that space but it is a good segue to the flip side which is email truly is this treasure trove of information so how do we get all of the stuff out of email and this is the latest feature that we launched actually just last week this is the thing that dharmesh tweeted about this morning which is ask ai if you think about what's in email it's things like project statuses customer communication meeting summaries deal execution so much more you name it email has it and for over 40 years we've had to rely on i hate to say this search you have to remember senders guess keywords scan subject lines but with superhuman ai and with ask ai you can just ask where is the q2 offsite or when is my flight and uh i'd love to show you should we do another let's do it yeah no i mean ai on an inbox is just such an unlock obviously and i want to be able to do this across the whole organization so back to like enterprise and and ceos and compliance man to be able this will come up at some point with these thousand plus installs you have there there's a compliance person who will want to do this not just on their inbox but for the whole organization has anybody talked to customer x you know blah blah blah but let's put that aside and let's give an example here here we are we're in the search box and uh yeah and i know that there's a an upcoming superhuman off site but uh right now i don't remember the details of it so i'm just gonna type in here where is the upcoming superhuman off site where is the upcoming superhuman offsite.

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44:57Probably don't need to fix this, but let's just go ahead and do that. And you'll notice I now have this option to ask AI. If I just typed that in, or if I just did a search, I wouldn't get any search results. What we've done here is we've indexed and put in the vector database the last year's worth of email. We've also indexed all of your calendar and it says based on your calendar, the upcoming offsite is in San Diego. Actually turns out to be next week. I'm very much looking forward to this. We've also generated follow-up questions, by the way you know i'm available for offsets dude you should come it's going to be amazing uh we are going to have some customers there i'd love to have investors there as well let's say i want to say what do i want to do to prepare i can just go ahead and click this and what we're doing here is we're simulating a conversation you might have with an in-person or an online assistant who just has all the information for you based on your emails this is what you should consider i have a session that i need to prepare for there are all these documents and if i wanted to learn more here are sources this is where we're generating the information from now one of my favorite things about superhuman off sites are the hack days as a fellow entrepreneur you'll know that hack days are the best days yeah that's when you see all the fun stuff um will there be a hack day let's find out now this is so dope this honestly is life-changing this is so hard to do with regular search and of course there will be a hack day because of course it wouldn't be an offsite without one and i can open this and click through and just get more information okay now we just have to pause here for people who are not watching the the elegance of this conversation is just so brilliant because you ask a simple question then it gave you what it perceives as your next three follow-on questions but it also cites sources in this case the sources are those threads so this is a problem we all face constantly which is you have a question you go to slack you ask it somebody searches their inbox they cut and paste it back to you and say hey dummy it's in your inbox and then you say well i'm the ceo i get 400 emails sorry we'll bleep that out but i am the ceo i get 400 emails a day do you not understand have any empathy for what my life is like or you know anybody who's a super router and so here it's just so great that you somebody on your team had the presence of mind to say well let's just cite the sources because then i can jump into that thread and actually comment on it but you know what happens is when you have so much friction to find that answer to find those email threads because your email box has a hundred thousand or a million emails in it you just don't do it and then you don't want to bother people in here it's like you're not bothering anybody and this is just saves everybody on the organization if you just do one of these a week i think each one of these is like a 20 minute thing totally yeah you know and you take 20 minutes you know in 10 weeks that's 200 you know every three weeks it's an hour basically so you know you're talking about another 15 hours and this is i love about your product and your team is so thoughtful because the fact that there's somebody in the world obsessing about saving 20 minutes a week for a large base of users now building spending 500 developer hours to build something or 5 000 in this this is probably 5 000 hours of developer or 10 000 hours of developer nobody's going to do that but if you can do that and distribute that cost across you know tens of thousands hundreds of thousands of users it's like well why wouldn't you do it and it's just this is so dope man what a game changer it's really fun to build as well and by By the way, I haven't even shown you the most impressive version of this that I found yet.

48:30So this is really great. Like this takes the load off my EA. It takes the load off the organization in general. Like I work weird hours. I don't want to, you know, ping them at two in the morning. Yo, what should I prepare for the off sites? Oh, here it is. Like they've already put it in email. It's fantastic. Let me show you this though. Okay. So we launched this not too long ago. And like any good CEO, I wanted to do a cheerleading moment. What do I mean by that? I mean, I wanted to read through all the responses we got. We probably got like 500 ,000 responses via a two-hour launch email on this.

49:04Pick the 10 best quotes, put them in an email, put them in a Google Slides, go to the company all hands that week, Friday wins, and present them, right? That's a lot of work. And I did it manually just to see how long it would take, because that's what I've always done. And it took about 20 to 30 minutes to read through all those responses, to do the copy and paste to like futz around with um all of that it's just a lot of time and then for shits and giggles i was like okay let's see how fast it is with superhuman ai with ask ai so i'm gonna do it over here in the sidebar you can also click this little item down here we have used the question mark shortcut so i'm just going to go ahead and hit question mark and i'm going to say find me the top 10 most positive customer responses to the SAI launch make sure each one is at least two sentences I want to get substantial responses here think about the craziness at this point it's going through millions of emails I've received over the last year it's synthesizing information this is true needle in a haystack combination information synthesis stuff all i have to do is hit copy come here hit paste the formatting's perfect it is done it is done dude this is half an hour it's half an hour i mean come on you would this you know this could be multiple hours and then you have to let somebody into your inbox to hunt and pack it and you know this is it goes to the podcasting you know um you know uh anecdotes i was saying before there's there's a lot of things that you just wouldn't do if you had to throw a human at it right you're just not going to do it um and you know or you'll never get to it and you'll and then you ask your team hey can somebody do this and they're like everybody's too busy we need to hire a new person who'll be the director of research of reviews and you're like I don't want to add headcount.

51:07And when we look, let's step back here. You and I as both investors, and you've done really well as an investor, as your side hustle. As investors and as entrepreneurs, how you run a company has changed so dramatically in our time in this industry. You, 20 years in, me 30. Like it is insane how different it is to start a company now than 30 years ago, then 20 years ago, then 10 and even two. maybe you could talk about just um what we call on this program static team size where people are keeping the same number of people but then investing in tools and technology for those people because it's just better to not increase team size and invest you know whatever low thousands of dollars into each employee with each product with each amount of training and then just keep the team size the same, but get, let's call it 30 % out of each person extra per year.

52:11If you get but 31 % out of each person per year, you're doubling your team size every two years. That's called the rule of 72. People can look it up in terms of compounding interest. If you were to get but 23 % out of every user, I'm sorry, every employee, you would double your team size every three years. Maybe you can talk a little bit about running a company, how you think about team size and also you know as part of this you were one of the very smart founders who made hay when the sun was shining and raised you know i'm going to just say you know a war chest um at peak zirp during those eras and then been very thoughtful about how you're deploying it and sitting on that war chest take either of those and dovetail them how you want sure um okay let's take the second first i have a uh a relatively unusual method of managing burn let me see if i actually have it i'm just gonna do a quick question to superhuman ai and i love it i could do that i'm actually gonna do this you don't want to go too live in your database i don't want weird stuff to come up yeah crazy okay here we go so um anyone can look look uh this up if you're listening via audio, Google, how to run your startup in a recession.

53:30And it's in multiple places. This one is on AngelList. Now, there's all kinds of ways you can do this, right? You can do whatever it takes to get to profitability. There are some obvious problems with that, namely that you start to constrict things. Marketing is usually the first to go, then sales, and then you start cutting into engineering products and design. And if you're in a market worth fighting for, somebody else will overtake you. Or you can aim to get to a certain amount of runway. Some people aim for 24, which by the way, why 24? Guys, that's not enough. You need more than 24 months of runway, whether it's a recession or not.

54:05But the point is aiming at any fixed static number doesn't have a margin for error built into it. So we do something pretty unusual. I've never seen any other company do this. We pick the amount of runway that we want to maintain, in our case, we actually are very conservative, 48 months. And every single period of time, I've written here, we do it yearly, we actually do it quarterly. Every single quarter, we make sure that at that moment in time, we have 48 months of runway left. Got it. Which actually makes really fun conversations with investors or potential acquirers or even candidates who are interested in joining the company.

54:42Everyone says, how much runway do you have left? And I said, well, Bob, we always have 48 months runway. Every single time we have this conversation this time next year it'll be 48 so if you're planning to wait me out that's not gonna work right it's always 48 months of runway yeah if you're looking to lowball with four weeks not gonna happen you gotta pay gotta pay to play love it so um and in this article i go through the details of how you can do this and i think this is just a really powerful technique that more founders should consider okay so as we think about uh team size i totally hear you and i actually more sort of uh what's the word not experimentally but sort of i came across this idea that you just mentioned more in practice uh we got up to about 120 people um at sort of peak days um so to say and you know unfortunately like many other companies we we had to do a layoff we we got a little bit ahead of our skis uh what i am happy about if happy is not the right word what i what i feel at the very least not terrible about is back when we did it we were one of the very first companies to do this and you know i think if uh the economy is pretty frothy right now i don't think we're in any imminent danger um but if we were to head into another recession my advice founders would be if you are considering the layoff do it sooner than later because you want to release your people into a job market that is still hot, where they can still easily get that next role.

56:13And the sooner you do it, the more money you'll save, the more severance you can afford to pay. It's just better off for everybody. So we did this relatively early in the cycle. It was well before most of our contemporaries. And that brought us down from around 120 people down to around 70 or 80 people or so. We've recently climbed back up to the 100 to 110 mark. And to your point, we've actually stayed there for, I think, the last year and a half, maybe even two years. It is a really, really nice size of company to run. There's just something magical about that size where communication doesn't break down.

56:49You don't have too many silos. You do have some management in the middle of the organization, but it's not so much that things get lost or people start to build kingdoms or fiefdoms. I was about to say, the tribalism can't happen because you can bring the leaders to the offsite and you have enough of the people at the offsite. I don't know if you're bringing everybody, but... We're bringing everybody. Well, incredible. And it's enough that you as the CEO and the founder essentially know everybody. And you can maintain, I believe, as a founder, you kind of get to 20, 30 core people in your team that you can maintain a very deep relationship with, know their families, know where they're at, talk to them every month.

57:29um in are you seeing gains in productivity each year because of ai internally so let's put aside superhumans ai efforts but just broadly you're using a lot of different tools i'm sure you've got tools in sales i'm sure you've got tools whether you use notion or coda which are very ai powered now uh you got slack getting ai you got developers using co-pilots so talk to me about how you're thinking when you're running the organization investing in your people to make them more efficient and what kind of gains do you see from ai you know and personal development yeah i mean in short we are i think the most important thing that a founder or a ceo has to do is make it clear to the organization that's what they expect hey folks i expect you to get more productive every single year with ai and then the thing that i'm going to do is release the budget to make that happen and also the expectation that not every piece of software is going to work.

58:23We've, I don't know, trialed probably 10, 15 different bits of AI software. Maybe a third of them have really stuck and have had a high hit rate. Personally, my favorite outside of Superhuman and outside of ChatGPT is Loom AI. A lot of what I do as a product and design-oriented founder is I sweat the tiny little details, and I'm constantly recording Looms. I'm like, hey, when I click this thing or I do this thing, this shifts by a pixel, oh, this isn't quite right. And here, let me open the console in Chrome. Let me show you what's going on. Let's fix the CSS, whatever it is. You're basically sportscasting with Loom.

58:58And, you know, they say a picture's worth a thousand words. A video's worth a billion pictures. Because when you're watching the product demo and saying like, hey, you know, this, this, and this, boom. And what I've gotten now is smart founders will, they know I love a good Loom and they will make a custom Loom. So just think about that as like, an unlock you're you got some seed stage company you're or you're trying to get into our accelerator or y combinator and you just send a little loom to us two minutes hey jay cow i wanted to show you my product i know you invested in superhuman we're superhuman for blah blah blah here's how it works we got this we got this we haven't built this and i'm hearing from the founder in their own voice what essentially would be an elevator pitch at a party where it's too noisy and now i got visuals and people were like i'm too busy to send that you're you're too busy not to send right and then folks that don't know that where loom ai comes in and hopefully your founders are doing this when they pitch you is it will automatically title the video it'll automatically create a transcript and as i'm thinking about my loom activity i probably record 30 40 a day imagine if the recipients had to actually watch the video in detail every single time even at 1.2 or 1.5x that's a lot of time what they can now do though is they can pre-arch they can read the title they can read the transcripts no wait is loom ai different than just the standard loom by atlassian is this two different companies or the same one uh it is the uh it is the same company i'm just going to throw it up on the screen for our video viewers i'm not going to play this because it's it's me uh giving feedback on the bug but i did not create this title uh i did not write this summary i did not make chapters oh my god so genius what a great unlock from our friends at loom atlassian they're not sponsors of the show but uh we both give it five stars great product and what a great punch up here um and look on this right hand side pre-suggest suggested tasks for viewers you can read through the transcripts if you're in an environment where you can't listen to audio sometimes reading is faster i mean this is just such a phenomenally well executed ai tool it's just such an incredible moment in time i was talking to one of the top 20 most legendary founders billionaires on the planet we had dinner the other night and we're just just bashing things out and talking he said uh have you ever seen anything like this we've both been in the industry the same amount of time he said no and uh it's super motivating to me he says i can't wait to get to work every day and uh you know i'm i'm you know taking meetings at eight o 'clock at night seven o 'clock at night nine o 'clock at night because somebody's got something so amazing i can't wait to see it it's just like everything we've worked on in the last 20 30 40 years of computing has led to this moment where ai takes what happened in desktop software cloud computing storage bandwidth machine learning big data mobile video and then it's like yeah you know what boom everything is like these ingredients now to this super dish which is human beings are getting i think the human beings who are embracing this are getting 10 20 better per month you know and i have 21 people in the in the investment firm now it's a lot of people for you know a 50 million dollar fund uh you know we have very profitable um events business and and podcast business that you're listening to right now everybody so i kind of spend that on you increasing this but man the top third of my team that embraces this they are like the difference between the top third and the bottom third of people people who like hard embrace ai and people who are not embracing it and then there's everybody in between who are kind of dabbling if you just break those three cohorts up i think the difference between group one and two hard embrace and dabbling in terms of value to a company is like 10x and then you go to people who are not embracing it versus dabblers and people who are embracing it the people who are embracing it i think are becoming a hundred times more valuable to an organization if you were to look at this what are you what are you seeing in this regard uh that that's absolutely what i see what i hear as well uh speaking of ed sim we mentioned him earlier in the episode he noted uh he's an investor he noted that when he talks to founders who are in the early 20s maybe they've just come out of college the way that they code and the way they build is entirely different to people who've been coding for 5-10 years plus and like it's just a different expectation a different workflow not only is it faster it's also faster to iterate and yeah i mean is it 100x i don't know but certainly in the region of 5 to 10x for certain things, an area that I use AI a lot, apart from just Loom AI, is for writing copy.

1:04:01And I mean, you're a great marketer as well, but sometimes we just can't think of the headline. And what I do, and this is the simplest use case, but it's so powerful, is I just go to ChatGPT and go, yo, can you give me 10 more versions of this headline, please? Make it pithier, make it funnier, find a joke, you know? And that's all I need to actually make it pop. Well, what happens when you do it, and we have a company, Saga, that's making a um a tool for kind of like final draft for writing screenplays and it also makes um storyboards which i push them hard on like you're a screenplay writer and it automatically starts making storyboards for you while you're typing holy cow or if you're a storyboard artist and it makes copy based on what you drew like that's kind of wild because those moments happen when the people get together and they share their work but it requires uh i'm a writer i need a storyboard artist or i'm a storyboard artist i need a writer like the brainstorming process writing jokes writing copy making images creating characters creating business plans it's it's like having somebody just bounce ideas off of available to you 24 7 and i would say when i do this same thing like i do it when i'm branding companies or products i'll be like here's what i want in a brand what do you think you know and it kind of starts giving me feedback whatever it's sparking in my brain connections that i would not have thought of because the if the ai gives me 90 garbage and 10 good it might spark the garbage might spark like that's garbage this would be better or that's brilliant how do i punch it up and so i am not precious about this anymore where i'm like oh artists you know people writing lyrics and i think people in hollywood who are like trying to i don't know if you saw when they had their strike role they were like trying to ban ai in the writer's room i'm like these people are going to the bathroom and using chat gpt if you ban it in the thing they're going to come back after pretending they're taking a leak with new ideas that they brainstorm with chat gpt let's not be precious i mean people sit there who are writers with a thesaurus or like they all go to a website filled with idioms and catchphrases and they'll do their searches there for ideas yeah um it's just so powerful for copywriting i think right now yeah i'm feeling like when we get the agent technology going um and you know the the the guide on the side who you proactively ask for stuff becomes like here's what you should focus on you know that's going to be the big unlock and i know that you're probably thinking that as well if i'm sitting here in my email box i really want a sidebar uh you know with scarlett johansson or gwyneth paltrow or you know whoever it is tom petty whatever person i like most you know in celebrity world saying hey man uh have you thought about giving raul a call and checking in on your investment and it's like in a bob dylan voice like it should be and i asked you for this feature like tell me who like 10 years ago i was talking to a whole bunch but that i i'm out of touch with and just yeah go find out what the hell they're doing in the world and maybe i should catch up with them so have you thought about your email box becoming you know your chief of staff and feeding you ideas of what to do next i don't want to i don't want to spoil the roadmap but i get the sense that you're thinking about this yeah absolutely that ask ai feature i demonstrated we consider as a proto agent and we have this framework internally that folks may find useful the evolution of ai features three phases phase one was on demand and these are features that uh work only when you ask them to work all of the you know right with ai features were like that they're very cheap to build they're very cheap to maintain generally speaking they're out of the way because they're not always there that's what we all started with and superhuman made a big splash for our right with ai feature when we when that came out early last year that then gave us the confidence to move on to phase two, which is always on AI.

1:08:01And you noted this in our demo with auto summarize, which is the one liner and the bullet points at the top of the email, a lot harder to build. Because for that kind of a feature, for every single email you receive, and boy, do our users receive a lot of emails, we're resummarizing the entire thread. And we've done that for probably north of 10 billion emails to date. That then gave us the confidence to build Ask AI, which like I said, is sort of a proto-agent. It can do some agent-like things today. For example, it's capable of multi-step conversations. We had a look at that. It's capable of resolving ambiguity.

1:08:36If I'm like, hey, what did Jason last email me about? It would probably say, do you mean Jason Calacanis or Jason XYZ? And once we've resolved the ambiguity, it's then going to give me the answer. But it's not too long before we can imagine an AR agent that is sitting in your inbox, drafting emails on your behalf, scheduling meetings on your behalf, maybe even sending fully written emails one day on your behalf. Are the auto replies that you're doing now, because I just used it for the first time, I always look at them, but I consider my voice very unique and I want it in my voice. I'm not kind of the guy who wants to one click, use one of those things.

1:09:15Is it studying my voice yet to give me ones that are different than yours you might be a little formal english and you know blimey or whatever and i might be brooklyn be like what this is you know inappropriate exploitive here is it actually using my replies to craft my auto reply one clicks yet it is but not in the way yet that i'd like it to so we we do study the emails that you've sent and we sort of condense that into a voice signature if you will we apply that to the emails that we right but i'm not yet satisfied and there's some pretty obvious improvements that we will be making over the course of the next i think six months or so i'm pretty hopeful uh that will get a lot more like you uh because that is the feedback that we hear the most which is hey this feature is amazing and i use it on my personal email where stakes are fairly low right i'm you know i'm interacting with my my dentist or or this contractor or whatever it is whatever yeah boom who cares but with a work colleague you do want it to sound like you with a founder you want to sound like you so uh that will happen over the course of the next six months yeah i i linkedin is uh your alma mater is like doing these at the bottom and i noticed you know we we do a little thing with our athena um uh support staff go to athenalow.com get a free month off or something like that um I have my own domain to track all my referrals as an investor.

1:10:39And we gave them a list of all of our companies, all of our founders. It was probably of the 400, maybe 250 are still active in the last 12 years. And they look at yours and they look at superhumans, corporate stuff, and they will give us every day 20 updates that they think are interesting. We open them up. And then I just ask people on the teams, 21 of us, engage in four a day. but meaningfully engaged because people were using the linkedin thing like impressive exclamation point or awesome and i'm just like less is more write something more thoughtful there should be like a slider of like more verbose and i love grammarly do you use grammarly at all um i'm in and out of grammarly just to see what they're up to yeah i mean they remind me of you in terms of their product velocity and thoughtfulness and as a writer i think they're doing just a great job and they they have a really cool tool i force everybody in the team to use it because i'm like um they have like business clarity concise verbose you know it really gets granular there so built-in ios android whatever you know grammar correction will get you you know to phase one but to get to phase two or three where you're really being thoughtful about is this a concise conversation verbose one you know that's what i need in in these um auto replies because right now i'm looking at one on my mobile and it's like great potential any updates impressive work and i would like a full sentence right so i could just set that full sentence shorten or maybe just shows me three levels concise verbose spicy whatever you know um but such great potential listen bro you're amazing thank you for letting me invest in your company i'm so glad that when all the secondary people came and tried to buy me out i said no because i think you're going to build uh a legendary company you already have but i think it's a legendary company that will be here 10 20 years from now because you're not like you're really thinking about these problems in a deep way and i encourage all founders to watch this episode with your teams uh so that you can catch up to some of the best practices that we see out there if you want to make your organization um literally you know two three four times more efficient get them all on superhuman easiest uh this is the easiest spend you can do superhuman.com superhuman.com superhuman.com you got to have like your top three or four people on it learn it do the training and then decide for yourself if you want to bring the other 10 people uh but you know that's your assignment everybody over the next 48 hours if you're listening to my voice you gotta you gotta take it seriously and invest in tools like superhuman uh anything else i can plug for you you're hiring you got a position you you can't you got some sticky position that's hard to fill that you need uh nothing that's particularly sticky we just opened up a product manager role i know a lot of product folks into watch the pod yeah if that's interesting this is uh going to focus on core products products for the enterprise uh calendar we just wanted to share availability feature which people really love it is a lot of people's dreams to work on productivity tools because usually they're not very good businesses usually it's like it's my you know my every engineer has built an email client but we've actually cracked the nuts here we found the formula and so if that's the kind of thing that you want to work on then come work with us hey listen if you're an elite product manager you know superhuman is one of the great places you could be because you'll be amongst other elite product designers and a great product leader in a product-led organization and we will see you all next time on this week in startups bye bye bye

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Todays show:

Superhuman’s Rahul Vohra joins Jason to discuss the evolution of Superhuman. They delve into Superhuman's onboarding strategy (11:17), live demos of Superhuman's AI features (27:37), explore AI's impact on team management (52:07), and more!

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Timestamps:

(0:00) Superhuman’s Rahul Vohra joins Jason

(2:02) Rahul Vohra's background and Superhuman's pitch

(6:33) Evolution and early challenges of Superhuman

(9:59) NetSuite - Download the CFO’s Guide to AI and Machine Learning today! Visit https://netsuite.com/twist

(11:17) Superhuman's onboarding strategy and customer feedback importance

(20:55) New features in Superhuman 2.0 and multiplayer email

(26:00) AI's impact on podcast production

(26:16) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist

(27:37) Live demo of Superhuman 2.0

(38:38) AssemblyAI - Get 100 free hours to start building at https://www.assemblyai.com/twist

(40:08) Importance of documenting conversations and Superhuman for Sales

(44:17) Live demo of Superhuman's “Ask AI” feature

(52:07) AI's impact on productivity and team management

(58:27) AI tools for productivity

(1:07:26) AI's future as a chief of staff and email management

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