The Incredible Double Interview: Superhuman and Robinhood | E2090

Today's show: Jason interviews Rahul Vohra, CEO and founder of Superhuman, and Vlad Tenev, CEO and co-founder of Robinhood. This is a packed episode featuring founder tips, fun stories about how Superhuman and Robinhood got their start and much more! Timestamps: (0:00) Episode teaser(2:13) Product market fit and founder journeys(3:25) Jason's investment in Superhuman and market positioning(5:14) AI's role and features in Superhuman(10:25) Lemon.io. Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist(14:37) Targeting users and competitive advantages(22:23) Evolution and new features of Superhuman (20:52) Northwest Registered Agent. Get more privacy, more options, and more done—visit northwestregisteredagent.com/twist today! (24:37) Tackling spam with Superhuman's AI (27:05) Custom auto labels and email classification (29:47) Vapi. Go to Vapi.ai and use code Twist200 to get $200 in credits (32:03) Superhuman's auto reminders and drafts (34:14) Vlad Tenev and the origins of Robinhood (39:31) Product design philosophies of Robinhood and Superhuman (49:29) Scaling design principles and investment decisions( 52:31) Subjectivity in product design (55:14) Customer feedback in product development (1:00:00) Superhuman's subscription model and customer acquisition (1:05:11) PR strategies and news hijacking (1:12:06) Investment experiences with Robinhood (1:13:35) Navigating company valuation fluctuations (1:15:03) Influences on Vlad Tenev and new Robinhood desktop product (1:22:02) Company resilience and employee reorganization (1:25:52) Crypto regulation and startup mentality (1:30:05) Investment trends among Robinhood users (1:31:12) Retail benefits for startups and capital raising challenges (1:34:04) Accreditation for private investing and solutions Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com Check out the TWIST500: https://www.twist500.com Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp Links from this episode: Check out Superhuman: https://superhuman.com/ Check out Superhuman's blog post that details all of the new features Rahul went over in the demo: https://blog.superhuman.com/the-next-superhuman-ai/. Check out Robinhood Legend: https://robinhood.com/us/en/legend/ Article "How Superhuman Built an Engine to Find Product Market Fit": https://review.firstround.com/how-superhuman-built-an-engine-to-find-product-market-fit/ Check out Rick Rubin's book: https://www.amazon.ca/Creative-Act-Way-Being/dp/0593652886 Article on Bezos and Washington Post: https://www.newsweek.com/bezos-makes-big-change-washington-post-opinion-focus-endorsed-musk-2036618 Media Bias Chart: https://www.allsides.com/media-bias/media-bias-chart Check out "Working Backwards" book about Amazon insights: https://www.amazon.ca/Working-Backwards-Insights-Stories-Secrets/dp/1250267595 Check out Rahul's article on acquisition: https://www.linkedin.com/pulse/rip-mailbox-founders-how-stop-worrying-love-being-acquired-vohra/ Follow Rahul: X: https://x.com/rahulvohra LinkedIn: https://www.linkedin.com/in/rahulvohra/ Follow Vlad: X: https://x.com/vladtenev LinkedIn: https://www.linkedin.com/in/vlad-tenev-7037591b/ Follow Jason: X: https://twitter.com/Jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis Thank you to our partners: (10:25) Lemon.io. Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist (20:52) Northwest Registered Agent. Get more privacy, more options, and more done—visit northwestregisteredagent.com/twist today! (29:47) Vapi. Go to Vapi.ai and use code Twist200 to get $200 in credits

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Jason Calacanis?

  Tell him the story. This is the, this was the, this is what I knew I invested in the right guy.

• 0:04Speaker 01

  We used to onboard every single person in person and I did the first several hundred myself, including Jason. The very first thing I did when I sat down with Jason and all these other folks was, uh, so, so as a reminder, this is a paid product and no one gets it for free, not especially not investors. That's how I'm going to keep us intellectually honest here on your feedback. It was like, what? And I was like, yep, time to pull out your credit card. Here's, here's a little Stripe payment form. Put it in, please. And I, I sat there watching him put in his credit card. I did that hundreds of times.

• 0:36Jason Calacanis?

  It was so great. What, um, can you imagine you're the first investor in the company? He's, it's a year later and he's finally ready to show it to me. Uh, so you, you log in and like I'm over the shoulder and he's like, okay, now you take out your credit, you put it in. I was like, yeah, okay. So yeah, how do I skip this? And he's like, no, you actually put your credit card in. It's a dollar a day. It's 365 days, you know, and I'm like,

• 0:55Speaker 01

  It's kind of expensive.

• 0:57Jason Calacanis?

  I was like, you know what? A moment of truth. This thing better save me a [bleep] hour a day on my email.

• 1:03Speaker 02

  This Week in Startups is brought to you by lemon.io. Get access to Lemon Hire, a platform with more than 80,000 pre-vetted engineers that you can interview within 48 hours. Get $2,000 off your first hire at lemon.io/hire today. Northwest Registered Agent. Starting your business should be simple. With Northwest Registered Agent, you can form your entire business identity in just 10 clicks and 10 minutes. From LLC to trademarks, domains to custom websites, they've got you covered. Get more privacy, more options and more done. Visit northwestregisteredagent.com/twist today. And Vapi. Add real-time AI-powered voice conversations to your apps or business in minutes, not months. Go to vapi.ai and use code TWIST200 to get $200 in credits. That's over 1,000 minutes in free calls.

• 1:47Jason Calacanis?

  Hey everybody, welcome back to This Week in Startups. I'm your host, Jason Calacanis, and today we have an exceptional episode. Two of my favorite investments, uh, Superhuman and Robinhood are run by Raul, Vora, and Vlad Tenev, and they are on the podcast today individually with an overlap in the middle. And this is an extraordinary episode because I can always tell when it's extraordinary. These are two of the smartest people I bet on. They've built two huge companies. You know, these brands and we talk a lot about products, product market fit, acquiring customers and their, their individual journeys. You're going to need to watch this with everybody on your team. You're going to need to take notes. You do not need to put this on a high speed because you're going to want to really take detailed notes or run it through an AI because

• 2:31Jason Calacanis?

  there's so many founder lessons in here. The density of knowledge and advice is crazy. This will be the number one episode of the year, I predict. Buckle up, everybody. I'm super excited to have my friend, entrepreneur Raoul Vora on the program. I met him because I emailed over a decade ago, [email protected] was a little tool I was using in my Gmail. They told me in my Gmail, "Hey, this person emailing you, this is their LinkedIn, this is their Twitter, this new service that had come out." And I could very quickly follow them on the other services and it grew into even more enrichment of the lead. I was just

• 3:10Jason Calacanis?

  a nascent angel investor writing 25 or 50K checks. And Raoul then did a tour of duty over at LinkedIn. And I said to him, "Hey, please, if you, when you come up with your next idea, promise me I'll be the first investor." He said, "Yeah, no, I would always contact you if I'm doing another project." I said, "No, I want a, I want a literal promise from you." He looked at me like I was crazy, which if you listen to this program more than 10 times, you know, is more accurate than not. And he agreed. One Sunday afternoon, he said, "Hey, Jake, are you around?" I said, "Can't wait to hear the new idea. I'm getting bagels. Meet me here in Calhalla." And he told me the story of wanting to take on Gmail with a product that was faster, better, and that he would charge a dollar a day for

• 3:54Jason Calacanis?

  or so, and that it would be a new category, a category referred to as luxury or power user software. And you always know a great entrepreneur when future entrepreneurs pitch themselves with the same playbook. So I've got no less than 500 people who've applied to our accelerators and our fund, which you can do at launch.co/apply and get a meeting with our team. No less than 500 people have said, "We're superhuman for X," which is now short in the city of San Francisco and the wider entrepreneurial community around the world, as I'm going to make something that is designed elegantly and for power users. With that, welcome my friend, Raoul.

• 4:38Speaker 01

  Amazing. What an intro. Thank you for having me back.

• 4:41Jason Calacanis?

  You know, that intro is off the top of my head because I just know the story so well. And, you know, when you have a great hit and you have, you know, a great relationship with the founder as an investor, you know, you cherish it because it's fun and it's been so fun to watch your career and get to, you know, play a minor role in it and be on the sidelines. And once in a while, you got to make a hard decision and we talk, which is, you know, it just makes me feel great to be on the other side of those phone calls. I wanted to have you on today to get the update on Superhuman. So many topics to talk about. And you did actually a nice private discussion with our syndicate, the Syndicate.com, and our angels last week. Thank you for doing that.

• 5:23Jason Calacanis?

  That was a private conversation. But let's start with how AI is impacting your business. Everybody knows Superhuman. It's elegant. It's fantastic. You have a large number of users. You've raised a large amount of capital and you're extremely, extremely focused. But you've made a bunch of AI announcements since you were last on and we've been talking about, hey, how is email going to get impacted? I've had no less than 50 different AI companies tell me that they're planning on building what you've already built. So let's go through what Superhuman has done in AI, how it's worked, and then we'll get into what you've been releasing recently.

• 6:03Speaker 01

  Absolutely. Okay. Wow. That's quite the tier. So let's split that then into two pieces. There's what we've done and what's coming. I think what we've done is even by itself pretty special. So for those that don't know, Superhuman is the most productive email app ever made. Our customers are getting to their email about twice as fast as before. They reply one to two days sooner. They save four hours per person every single week. Those customers are the latest startups coming out of amazing accelerators and incubators like Jason's, like my Combinator, all the way through up to some of the biggest companies in the world. We recently sold one of the big three management strategy consulting firms. I can't say which one. We have thousands of people there using Superhuman, which is incredible. And actually, even just a year ago,

• 6:47Speaker 01

  that would have been unthinkable. So very exciting to see all of that happening. What we've been doing over the last year or two is heavily investing in AI. We were one of the first to the game and started with what you might consider now to be surface level features, things like Write With AI. So you can just turn a few ideas or a phrase into a fully written email. The thing that differentiates Write With AI and Superhuman versus what you might be familiar with in, let's say Copilot or in Gemini, is it genuinely writes like you. We all talk differently to different people, you know, with some people were more structured and formal, with others were more casual and relaxed. And Superhuman knows the difference. It knows how you write to specific people. And we'll actually take a look at an example of that. So that's Write With AI.

• 7:33Speaker 01

  We also have Auto Summarize. You've probably seen this, Jason, at the top of your emails.

• 7:37Jason Calacanis?

  So great.

• 7:38Speaker 01

  Yeah, these one line summaries.

• 7:39Jason Calacanis?

  I love it.

• 7:40Speaker 01

  Your email really fast and instant reply. So imagine waking up to an inbox where every single email already had a draft reply. You would just hit edit and then send. And then the last thing that we released in the past, but this is actually of the four things I've mentioned, this is people's most favorite thing is Ask AI. This is what I demonstrated on the podcast last summer. You can basically come in and ask a question. Sam Altman talks a lot about how AI is taking increasingly large chunks of work and making it instantaneous, or at least asynchronous. And the example that I showed last time was a very real example, which is every time we launch a feature, I read through the thousands of emails that we get back and I pick the best ones and I put them on a slide and I present them to the company in all hands.

• 8:25Speaker 01

  It usually takes me 20 minutes, half an hour. It's kind of a lot of work and with Ask AI, I can do that instantly. So that's all by way of what we've already done. But last week, we launched our biggest evolution yet.

• 8:38Jason Calacanis?

  These features are awesome. I love the summaries because sometimes people feel when they're raising money, they need to send me not only their pitch, but their life story, including the last three startup ideas they had and what it was like growing up in their small town. When I'm a venture guy, I was like, what's the idea? Do I have a conflict in the portfolio? And let's get right to it. So some of them are obvious and but, you know, it's always about the execution, I find. And that's one thing that you have had a profound impact, I think, on my thinking and the industry's thinking, which is. How should this be executed? A lot of the ideas, listen, it's obvious that you should make a summary of emails, but how do you execute it? And having a point of view about that and understanding who is your customer?

• 9:23Jason Calacanis?

  I think before we go to what the new stuff, I want to just pause for a second and talk about your philosophy on features and executing them well versus executing them quickly. There's been this big debate in our industry, you know, ship fast, you know, break things if you're not embarrassed by it. You obviously don't take that. You want to have refined features. So give me your thoughts on and how it might have changed over time. When you feel something's ready to be launched and how much time you put into it? How much time do you spend, you know, in the laboratory? Maybe in a small beta test with a couple of users? What's the playbook for you now?

• 10:07Speaker 01

  Well, it's funny that you say playbook because, and you mentioned execution. I, one of the things folks like to know about this podcast is I'm very excited to share my screen. Let's do something I've never done before. I'm going to share a slide from the Series C deck, which I think is very relevant here.

• 10:24Jason Calacanis?

  Founders, let's be real, let's keep it a buck. Finding great developers is hard. It's like one of the hardest things you have to do in our industry, especially when you're trying to run and scale your startup. But here's the good news. I got a tip that's going to save you time, money and a ton of headaches. You need to check out lemon.io. Lemon.io has thousands of on-demand developers who can help you. They have done all the work to find and vet great developers who are experienced, who are results oriented and who charge competitive rate. Great developers we know are hard to find and integrate into your team. So lemon.io will handle all of that for you.

• 11:07Jason Calacanis?

  They're only going to offer you handpicked developers with at least three years of experience. And if something goes wrong, lemon.io will find you a replacement developer ASAP. A bunch of launch founders have worked with lemon.io and they have told me they've had a great experience. So here's Your call to action, go to lemon.io/twist and find your perfect developer or an entire tech team in 48 hours or less. And Twist listeners get 15% off the first four weeks. So stop burning money, hire developers smarter. Visit lemon.io/twist.

• 11:42Speaker 01

  So it's funny you mentioned execution and Jason, you haven't even seen this deck, but you somehow knit the nail on the head here. Which is we have this thing that we call our joy formula. And I need to be careful what slides I share because this is genuinely our series C deck. But basically, you know, we, we have this saying internally, which is that what we make people feel is just as important as what we make. And people have asked us for a long time, like what, what are you actually making? And what it really is, is joy in software form. And lots of the smartest folks in Silicon Valley, of course, from, from Stripe, one of the best in the business, said, well, Google has hundreds, thousands of people working on Gmail and yet you were quickly, in some sense, easily able to build something better.

• 12:25Speaker 01

  Why you just sat down and calmly built something better. It feels like that shouldn't work. So what's going on? And so I wrote him back and I said, we actually have a formula for joy. We figured out how to build joy and then massively distribute it and scale it to people. And it starts with product design and engineering, but it's also in everything else that we do onboarding, delight, marketing and community. And Jason, what you were really getting at here is, is this 10x execution. So to make this sort of real and concrete for our watchers and listeners here, let's actually take that auto summarize feature. Of course, every email client, every app has a summary feature. But if you are deep into these features, you'll know there's a tremendous spectrum in how well they work.

• 13:08Speaker 01

  For example, in Gemini, in Copilot, in both of those experiences, you have to ask.

• 13:15Speaker 01

  Gmail or Outlook to summarize the email that you're looking at. And of course, it takes some time. It can take a second, two seconds, three seconds, depending on the length of the email and your network connection. Which, let's be real, by that point, frankly, you could have just skimmed the message and have your eyes locked on to the most important piece. So what we do at Superhuman, and many people thought this was crazy, is we are precomputing the summaries for every single email that every single one of our users receives. We're precomputing the replies for all of those things in their own voice, in their own tone. And that's just a massive amount of computation. Now, we can do that because we actually charge for our products. And I'm a big believer in charging a good price for your product and delivering the best service as opposed to monetizing your users in other ways. But we can do that, and so that's what we do.

• 14:00Jason Calacanis?

  This is a really good point for founders to consider, which is, in a crowded space where there's many people going after the same users, which I guess Patrick is sort of noting there, like, how does this opportunity even exist? If everybody's making schlocky stuff and you elevate it, well, it will stand out even more. And the onboarding is another thing you get a lot of credit for. Everybody's stealing this, which is, you know, is this product right for somebody? So let's talk about that for a second before we go to the new features, because I really want to educate the new founders who are listening. You are pretty militant about not letting people use your product if it's not for them.

• 14:44Jason Calacanis?

  So if somebody comes in and they want a Porsche, or a Lamborghini, or a Prius, these are three very different products at different price points with different, you know, offerings. A Tesla Model Y is faster than a Porsche in many instances, but that's not why people are buying a Porsche. A Lamborghini is slightly different, as you might know, and you can really start to parse this. They all get you from point A to B, but with different criteria. So how did you figure out what the criteria was for this joyful, luxurious, you know, luxurious software that is massively productive? And who should have it and who shouldn't? Because, gosh, you know, somebody comes in, they're like, yeah, I'll buy the car anyway, I don't care. But you just say, yeah, you kind of do need to care. So what were the criteria and how do you think about it?

• 15:30Speaker 01

  This is what I call strategy on a slide. So everyone should try and do this. This is really, really old, by the way. I don't know if it's legible, but this was done in 2017. And I think what I love about this is it's still relevant today. Like, this is still basically the strategy. And these are the rules I always advise. Have your strategy, number one. Number two, whatever your competitive advantages are. And number three, what hypotheses or assumptions you're making, because you've got to make sense, right? So let's, let's take a look here. Number one, position superhuman founders and CEOs of tech companies with twenty five, five hundred people, so definitely SMB. And look how niche that is, founders and CEOs of technology companies. Number two, deliver the world's fastest and most beautiful email experience. And then number three, sell into those companies.

• 16:12Speaker 01

  And this has not changed today. We're on step three of this very long but robust plan. Now, why did I know it was going to work? Well, because of, first of all, these competitive advantages. Number one, I had high levels of access to founders and CEOs in Silicon Valley and then to the media, the investors and the employees who influence them. And so this is definitely a second time founder luxury, but having built a well-known company, having sold it to an even more well-known company, LinkedIn, and then spending my two years at LinkedIn wisely, working hard, but also building my relationships. Uh, I, I was able to, if I needed to,

• 16:52Speaker 01

  by force of will and connection, get some of the most important people in Silicon Valley loving the product, which was the kernel that turned into onboarding. I was like, well, I'm, I'm just going to go and sell the first five hundred of these people myself. Why not? It's, it's a grind, but most people are scared of grind. Let's, let's go do the grind. So that kind of created the foundation. And then this is where you start to need to look at your, uh, your competitors, in this case incumbents. I mentioned this, uh, last Friday to the syndicate, but I, I like going up against incumbents. I like investing in companies that go up against incumbents. Because by the time you matter, it's generally too late. And even today, we don't matter to Gmail or to Outlook. Like, we'd have to be ten times the size, maybe even a hundred times the size to truly matter competitively.

• 17:37Speaker 01

  And so, you know, we're, we're a microbe, uh, or we're a virus on a microbe on the back of a fly. Like, it's, it's, we're small. That said, it's important to have a strategy that works. And I always point to Conway's Law. If you're not familiar with Conway's Law, it's basically that you can see the structure of the organization in the products that they make. If you look at Gmail, you can basically see the organizational structure of Google. And that means that they struggle with certain specific things. So Microsoft and Google both struggle with creating fast products, not because they have bad engineers, actually the opposite, they have the world's best engineers, but simply because the products are already at scale and entrenched. And similarly, they struggle with design, again, not because they have bad designers,

• 18:20Speaker 01

  but because the leadership of these products changes every, excuse me, every two years. And they have to do a one-size-fits-all tool. So what if you just didn't do those things? What if you built it from scratch for speed? What if you had leadership like myself that isn't going to change for 10, 20 years? What if you don't build for a mass audience? Then you can do something special. And then you have your hypothesis, Row, and I have some examples down here. You can tell how old this slide is by how quaint these valuation numbers are. It's kind of funny. But this is the answer to your question, Jason. It's like, I sat down and I just wrote down this strategy that I knew would work.

• 18:57Jason Calacanis?

  And you know, writing, I always tell people this, is clarity of thought. If you stop talking and you stop doing meetings and you force yourself to write something down and then other people read it and you know they've read it and then you have a discussion, that is, you know, sort of the highest level of cognitive processing. And over time, you can have what you think, your mental model of the world, which is what you're building there, it's just like sort of mental model, you're building the chessboard, you picked a format, cleanly architected, and then everybody else can read and have a good discussion, as opposed to coming into a meeting and you're like, if you were looking at a chessboard and a bunch of pieces on the floor, you'd be like, I have a pawn, I

• 19:41Jason Calacanis?

  have a knight, and like, then your perspective is coming from those pieces, not from, you know, somebody sort of setting up the board for the discussion, right? You're setting up the board for the discussion here as the leader of the company. And then people can take each move you've done and say, you know what, why are we going here for CEOs and founders? Oh, you have access to them. Oh, they trust you already. Oh, you're a second-type founder. Oh, the product has virality in it. And if the CEO is using it, people look over the shoulder at what the CEO is doing. The CEO is the opinion leader of the company, whether they've earned it or not. You know, people are going to follow the leader. It's like literally why the term follow the leader exists. So let's take a look at what you built recently. And then I want to introduce you to a good friend of mine, Vlad from Robinhood,

• 20:25Jason Calacanis?

  who is another investment I made before the product's launch. That makes me look incredibly smart. Have you met Vlad before, by the way?

• 20:33Speaker 01

  No, but you know what? I come prepared. I have one of these with me.

• 20:38Jason Calacanis?

  Oh.

• 20:38Speaker 01

  And I have an ask. I'm going to have an ask for Vlad.

• 20:41Jason Calacanis?

  This is incredible. This is like bringing together Michael Jordan and like Steph Curry to like meet for the first time. This is going to be incredible moment on This Week in Startups.

• 20:53Jason Calacanis?

  All right, founders. Okay, digital nomads and my remote entrepreneurs, I need you to listen to me right now. I know you want to build that next great company. Well, you're going to need two things, right? You're going to need a great idea and you're going to need to properly set up your business. And that's where Northwest Registered Agent comes in. For just $39 plus state fees, here's what you're going to get. Privacy by default. Keep your personal info off public records with a business address, phone number and mail forwarding. And unlike other guys, they're never going to sell your data. And you're going to need to look super legit. That's important to customers, employees that you might hire, team members you're looking to hire, and of course investors.

• 21:36Jason Calacanis?

  So you want to have a professional online presence and you can get your domain, website and 10 business emails right at the start. So you're building the right way. And if you ever have questions, you won't be stuck talking to some chatbot. Nope. Northwest Registered Agent has expert corporate guides, not bots. So you're not going to get run around, just real people who know every single state's rules and will walk you through the process in 10 clicks and 10 minutes. Boom, your business is live. So join thousands of founders who trust Northwest. For just $39 plus state fees, you can launch your business fast, hassle-free and with total privacy.

• 22:17Jason Calacanis?

  So go to northwestregisteredagent.com/twist to start your business today. All right, show us what's coming. Show us what's new. Everybody is interested in seeing what's coming out of your brain at this moment.

• 22:32Speaker 01

  Okay, so as we know, we set out to build the most productive email app ever made. And we have done that, but just being ahead of the pack doesn't mean you stop. We always ask, why stop here? We want to be over there. So last week's launch is our biggest evolution yet. And now like truly great assistants, superhuman is going to be constantly helping you. Organizing your inbox, making sure you never drop the ball, drafting fully written emails on your behalf. And it can even execute complete workflows end to end, so you don't have to. And I feel like I'm making a habit of live demos here on Twist, which is always super risky because I'm going to demo this software. It might just break, but you know what?

• 23:10Jason Calacanis?

  Demo or die, as we would say in the business in the eighties, demo or die.

• 23:15Speaker 01

  We're going to do a number of things. First thing we're going to do is demonstrate built in auto labels, then custom auto labels, then split inbox using custom auto labels, then auto drafts and auto reminders. It's going to be a lot, but I think it's going to be very exciting. I'm going to kick us off with this message to you, Jason. So we've just had the best year yet at Superhuman. We more than doubled multiple revenue lines over 2024. Amazing, true. Shall we find some time to catch up next week? Just let me know. This is the inbox hero image for the day. Beautiful to see. One of the first things we wanted to deal with was how much nonsense lands in people's inboxes today.

• 23:57Speaker 01

  In fact, over the last year or two, increasingly many people would come to me and say, hey dude, what happened to, um, what happened to your spam filter? Because I'm just seeing all of these marketing emails, all of this unsolicited sales spam pitches I don't want to see. Uh, and most of them are really low quality. And I kind of blame you, superhuman. And I would have to explain. I hear you. It's not me. It's Gmail. It's Outlook. For some reason, they just seem to have stopped caring. They're starting to let all this stuff through. And it came to a head towards the end of last year where I'm like, you know, one of the Being the user interface cuts both ways. It lets you do everything.

• 24:37Jason Calacanis?

  Yeah.

• 24:38Speaker 01

  You also get blamed for all the crap that goes on in the platform underneath.

• 24:42Jason Calacanis?

  Yeah.

• 24:42Speaker 01

  And so I decided to take matters into our own hands and we have now completely rebuilt all of that. And so what I'm going to show you are our built in auto labels. So, once you're off the beta, we have this new section, superhuman AI over here.

• 24:56Jason Calacanis?

  Oh.

• 24:56Speaker 01

  And I'm going to go ahead and click on auto labels. Let's ignore the amazing stuff at the start, at the top for the moment. Focus on the bottom. We have four built in auto labels, news, marketing, pitch and social. And this stuff has been life changing. Let's actually take a look at why. Uh, let's go ahead and start with marketing. So this is real. Uh, this is my actual inbox. These timestamps are real. You see, I receive a marketing email every one to two minutes. And it just goes on and on and on. And this is all just today. And what we're doing now is if you have important other turned on, we're sweeping all of this marketing stuff up important into other. And we didn't stop there. We're also, because arguably Gmail and Outlook were theoretically doing that.

• 25:38Speaker 01

  What we're doing is what they weren't doing, which is if you're getting these pitches and as a CEO, as a founder, as an investor, you're getting 99% of low quality pitches all the time. It's the 1% that you really need to care about, especially when they come from people that you trust. But you're getting all these kinds of emails that you shouldn't need to see. Uh, in, in my case particularly, it's a lot of people trying to sell software. And I do want to hear from people whose tools we are using. What I don't want to hear from is the, the army of.

• 26:10Jason Calacanis?

  Yes.

• 26:10Speaker 01

  You, you know what I mean?

• 26:11Jason Calacanis?

  SDRs.

• 26:12Speaker 01

  Yeah.

• 26:13Jason Calacanis?

  Who are putting you in sequences. Hey, you didn't get back to my last one. Wondering if it's a good time. Please hit not interested. If you're not interested in your life, I see what you did there. It's a trap.

• 26:24Speaker 01

  All of these are swept out. Not to say that you don't want to look at them. We've put them in a place where you can very quickly just scan down this list and go, okay, that, that seems pretty interesting. Uh, but you don't actually have to go through it in your main inbox. Uh, there is now also a place for news and also a place for all of your social emails.

• 26:42Jason Calacanis?

  So great.

• 26:43Speaker 01

  Uh, so, so far so great. If you want to take it.

• 26:45Jason Calacanis?

  And you're training those across the corpus of users. So if, you know, I put the New York Times and Washington Post into news. You know, from the corpus of data that you have that this is a news source? Or how do you know it's news? Is that just an LLM is good at it?

• 27:05Speaker 01

  Yeah, this is one of the really interesting things, which is the way that we build quote unquote, intelligence or AI products, I think, has just changed. It used to be you would train a classifier and you can very easily do this with a simple classifier. But since we're processing every single email we receive anyway, for things like auto summarize and instant reply, we just also ask the LLM, hey, is this news? Is this, is it a pitch? You tell us and it doesn't cost anymore. It's just a few more topics.

• 27:35Jason Calacanis?

  It's so funny because you understand power users so well. As a power email user, a super router in the world, um, I create aliases. So when I sign up for something that's a shopping site or I sign up for a news site, I use a different email at calacanis.com. I will use different emails, um, like [email protected] is a group email when we send syndicate emails. You get the idea. So I built my own little hacks to build this, but man, I would, if somebody could have just done this for me, that was, you know, 10 hours of my life over the last 10 years is building my own system to organize this stuff. Uh, and, and you've actually now built it for every user. It's so brilliant.

• 28:18Speaker 01

  Yeah. Well, we'll hold that thought because on a perfect segue, it's almost as if you read my mind, you can make your own custom auto labels. Uh, so I have four that I've made here. This is exactly the kind of organization you're talking about. And this is just whatever you want. I think like many people, I'm kind of overloaded with social networks and I just don't really pay attention to them anymore. The, the one last social network I pay attention to is Twitter or X. DM me, I will see it. Uh, but if you LinkedIn message me, I got news for you. I ain't, I just ain't gonna see it. It's just too many. Now, the problem is, I sometimes receive really powerful messages via LinkedIn.

• 28:58Jason Calacanis?

  Yes.

• 28:59Speaker 01

  And you know, and I just don't know which of the ones to pay attention to. The problem is it's like less than a few percent. When people in mail me or when people send me a LinkedIn message saying they're interested in applying at Superhuman, I want to know, and you can see exactly that happened here. So this was actually marked social, a built in auto label and recruiting a custom auto label. So I was like, huh, that's interesting. I'm gonna go ahead and open that.

• 29:18Jason Calacanis?

  Two tags.

• 29:20Speaker 01

  Uh, Andy, I'm a CS major graduating from UC Berkeley this May. And I opened this door to make sure I wasn't revealing anything I shouldn't.

• 29:28Jason Calacanis?

  Yeah.

• 29:29Speaker 01

  I previously interned at Amazon and Microsoft. My senior thesis is on how long form emails on its way out. Would love to hear your ideas on this too. Let me know if you're open to a chat. Of course I'm open for a chat, and this is something I would simply have missed before. This is the power of, in this case, combining a built in auto label with a custom auto label.

• 29:48Jason Calacanis?

  2025 is going to be the year that voice AI really breaks out. Voice AI is going to change everything. And this technology is perfect for building a chatbot or automating customer calls and basically creating these next gen voice experiences. But building with these tools is so difficult. It's just a bear. It's going to take your developers months to build and test anything even basic unless you use VAPI. This is the fastest and easiest way to integrate voice into your products. It's just the most simple API you've ever used. It helps you build, test and deploy voice agents in just minutes. And you can create ultra realistic AI voices and customizable personalities. I like that part.

• 30:32Jason Calacanis?

  All with real time response speeds. You know what'd be great? Maybe I just demo it, okay? Listen to this.

• 30:39Speaker 03

  Hey, Jason, it's great to be on your podcast.

• 30:41Jason Calacanis?

  Oh, okay, great. Are you interested in being the co-host of the podcast?

• 30:45Speaker 03

  I mean, I'd love to. Just imagine the banter AI and humans, the ultimate duo. But I think I'll stick to helping out with Vapi for now.

• 30:53Jason Calacanis?

  All right.

• 30:53Speaker 03

  What's up in the startup world today?

• 30:55Jason Calacanis?

  You know, we have so many things going on in the startup world, including AI. So I'm wondering if you have any tips for founders on how to create great AI experiences?

• 31:05Speaker 03

  Totally. I mean, first off, keep it simple. Focus on solving real problems for users. Then make sure it feels natural. Good conversation dynamics are key. Oh, and don't forget to optimize for speed. Nobody likes waiting for a response. What do you think?

• 31:19Jason Calacanis?

  That sounds really good to me. Take care and chat soon. I say, these are ready for primetime. And if you want to give it a try, and you can see it works. Now you gotta give Vapi a try. V A P I dot A I. Vapi dot A I. Use the code TWIST200, T W I S T two hundred, to get $200 in free credits. That's over a thousand minutes in calls. Great job to the Vapi team.

• 31:46Speaker 01

  Andy, I will be in touch. Thank you for the message and for beautifully illustrating this point here. Let's talk about how you can actually turn this into a stream of work that you can then work on. Before I do that, I'm even gonna go back to your email and see if it worked. It did. Here's what I mean by worked. It has an auto reminder. So this, I did this really quickly. I should have probably slowed down. I did not set a reminder on this email. But I clearly expect a response from Jason. And reminders are very powerful in Superhuman. This is how most people use Superhuman. But what if you didn't need to send, set them? Well, in this case, I didn't, and yet it just worked. Jason, I see you open the email. Hello, hello.

• 32:28Speaker 01

  Uh, please don't reply because I'm gonna demonstrate.

• 32:32Jason Calacanis?

  Okay, sorry.

• 32:32Speaker 01

  Yeah, yeah, no, all good. I'm gonna demonstrate what happens if you don't reply. Uh, now normally this is gonna come back on Friday. That is using a feature that we call auto reminders. You can set the default reminder. This is in two days' time on all messages that need a follow-up. What I'm now gonna demonstrate is auto drafts. So let's actually say I want this email to come back in one minute. And in the meantime, I'm gonna go ahead and get back to my inbox over here.

• 33:02Jason Calacanis?

  Incredible. Um, if you haven't used Superhuman, I highly recommend it if you're a CEO, VC, or founder. If you spend, I would say, one hour or more a day in your email box, uh, then you qualify. If you spend three or four hours and you don't use this, well, you could gain back, at a minimum, I think, 25% of your time. At four hours a day, one hour per day is 365 hours. 365 hours is about 15 to 20% of the work year. Imagine what you could get back if you had an eighth day of the week. Superhuman is the eighth day of a week that founders and CEOs and investors get back.

• 33:48Jason Calacanis?

  How does that sound to you as a pitch if you're hearing my voice? Now, I'm not just saying this because I'm an investor in the company and it's going to return a multiple on my first fund. And if I cleared my position right now, it would. I'm not clearing my position. Stop asking me, everybody. I keep getting, this is, this is when I know the market's coming back is when everybody's asking me to clear my position. Speaking of never selling a share, let me bring in my good friend Vlad, the co-founder of Robinhood. Welcome. You've never met my good friend Raul from Superhero, have you?

• 34:18Speaker 04

  I have not, but I've been enjoying the demo. Good to meet you, Raul. Jason, always a pleasure.

• 34:24Jason Calacanis?

  You saw Raul hold up his gold card. I have the gold card as well.

• 34:30Speaker 04

  We gotta get you, we gotta get you solid gold, my man.

• 34:33Speaker 01

  That was gonna be my, my party ask. So, you know, let's just start with it. I have one ask for you, Vlad. Can I get a solid gold card?

• 34:41Speaker 04

  So.

• 34:42Jason Calacanis?

  Is my, first of all, is mine solid gold?

• 34:45Speaker 04

  Let's see it. Can we, can we?

• 34:46Jason Calacanis?

  Oh, God, I gotta get up from my desk. No, I don't have, I gotta get my desk.

• 34:49Speaker 04

  You would know if it's solid gold.

• 34:50Jason Calacanis?

  I mean, you sent it to me in the YSL envelope. Right, it was in a Saint Laurent envelope and I was one of the first ones. So I would assume you sent me solid gold. If you didn't, we're gonna have to have a conversation after this.

• 35:02Speaker 04

  No, no, we definitely, yeah. If you got, I think, I think I managed yours personally. Raul, you must have, you must have just gotten, gotten it via being a gold subscriber. Is that right? Or did we help you with that one too?

• 35:16Speaker 01

  That is right. And in fact, this is, if I may pitch your product for a second, this is my first Robinhood product. This is the thing that convinced me to sign up. I'm not the kind of person who trades day to day, but I am the kind of person who loves free money. And if folks don't know, this is 3% back on basically everything. So I was like, sign me the hell up.

• 35:38Jason Calacanis?

  It's a, it's a pretty great value proposition. Robin Hood, I was lucky enough to, I always like to tell the founder story. Vlad and I, we were both in Sequoia Circle or in the Silicon Valley Palo Alto Circle. I was at Antonio's Nut House, which I think is defunct now in Palo Alto. Somebody told me it shut down.

• 35:58Speaker 04

  It's defunct. Yeah.

• 36:00Jason Calacanis?

  Rest in peace.

• 36:00Speaker 04

  Very sad.

• 36:01Jason Calacanis?

  So I'm sitting there with my friend Adeo and Adeo's college roommate. His name is Elon Musk and the three of us are sitting there seeing. And Vlad walks in, he's like, hey, you know, J. Cal, blah, blah, blah. And he starts pitching me, Robin Hood. And I have to say, two of the stories I always tell people is how crazy both of your value propositions were. How non-consensus they were. Bro, how's this for a pitch? Vlad comes up, I'm a quad, blah, blah, blah. He's pitching me, I want to get young people to trade stocks. I said, Vlad, Vlad, young people? You know, like people who are on their parents Netflix account and live in the basement and won't buy a car? And like, they don't have a driver's license? And he's like, yeah, exactly, those people. I said, okay.

• 36:44Jason Calacanis?

  How are you going to get them to start trading for their future? He says, oh, that's the best part. It's going to be free to trade. I said, can I repeat back to you what you just told me? He said, yeah. I said, you want

• 36:58Jason Calacanis?

  a bunch of people who have no commitment toward their future to suddenly make a commitment and the way you're going to make money is by making it free. He says, yeah. And then I have this further conversation with them and I'm like, well, how do you get those people? He goes, oh, we're going to give them free stock in a company. You want to make it free, get people who are commitment phobic. And then you want to give them free shares in the company. That's your plan? He said, yes, that's my plan. And I said to him, I'm in. And Vlad said something to the effect of like, well, the way you said it back to me sounded like it was a stupid idea. I said, no. It costs E-Trade $400 to acquire a customer on CNBC. I remember this because they used to advertise on a gadget in my, in my magazine back in the

• 37:43Jason Calacanis?

  print magazine days. If you can get them for a $3 share, you just save $397. He's like, exactly. I said, you know, if you get this generation addicted to this product, they're going to grow up and they're going to get pregnant, they're going to get a 529, they're going to start buying mutual funds. They may YOLO into some crazy stock, but eventually it's going to happen. And you're both in the same fund. We distributed Robinhood at $14 a share, I think. And this is something with your fund, Raul, you're going to have to deal with, or you may have had to deal with when companies start going public. Have you had one go public yet and distributed a public yet?

• 38:21Speaker 01

  We're probably about two years away, but selling is so much harder than buying.

• 38:24Jason Calacanis?

  So I, you know, at the time, the, the concept was distribute immediately and let people make the decision. So I sent a note to everybody. I'm not selling a share in this company. Vlad's genius and his partner's brilliant too. Like they know what they're doing. Don't sell, because it was the bottom of the market, 22, I think, or something like that. You know, I said, don't sell. Then it goes up to $60. This would have been like a 5X in that fund. It was like a $50 million, it was a $10 million fund. This would have been a 4 or 5X on the fund. Instead, the fund's five on paper, but it would be like eight or something on paper. And then four realized instead of 1.5 realized or whatever it is. I don't have the exact number. So a lot of lessons there.

• 39:09Jason Calacanis?

  Never sell a share. If that founder is brilliant at product and you know, Vlad, welcome to the program. You're brilliant at product.

• 39:16Speaker 04

  Well, thank you. That means a lot. Yeah. And no, yeah, I'm glad, I'm glad, I'm glad to hear you say that and no worries about distributing, you know, even LeBron James misses an open dunk sometimes, you know?

• 39:30Jason Calacanis?

  I want to ask you, Vlad, you know, Raul's very considered and thoughtful and he is really focused on world-class design. You also world-class design. What's your philosophy on product design? If you could summarize it, because Raul's been telling us a bit of his, you know, this 10X philosophy and being really thoughtful about it.

• 39:52Speaker 04

  Yeah. I mean, what I'll tell you is. You know, we, Beijou and I, when we started the company, we had to learn this stuff from first principles. Right. And I actually learned a lot from him because in the early days, he did the design and I did the engineering. And neither of us, we weren't, we weren't designers or engineers. You know, we were both mathematicians. So we met at Stanford when we were in the physics department. And when we were studying physics, we both became math majors at around the same time. And so a lot of the skepticism in the early days was actually, you guys are two mathematicians.

• 40:34Speaker 04

  You're talking about building like an amazing consumer product. But we don't really have confidence that you know how to do that. Like, when's the last time you heard, you heard of two mathematicians building something?

• 40:49Speaker 04

  So that was, that was kind of the first round of skepticism before you get even into like the fact that it's a regulated industry. And the business model maybe was, was a little bit complex to understand how everyone else was charging $10. But we were gonna, gonna offer this stuff for free. There was just skepticism about the team and it was hard to hire as well because we were just, you know, starting from scratch. And so Beijou, what did he do? He, he bought a Wacom tablet and he was sketching user interfaces on Photoshop. And I was watching the Stanford iOS engineering courses on the Caltrain at 2X speed on my way down from San Francisco to Palo Alto.

• 41:30Speaker 04

  That's how we learned how to do design and, and how I learned to engineer consumer products. I think what was so differentiated about Robinhood at the time, Robinhood did two things well that, that hadn't been done before. One was introducing zero commissions and kind of proving that that could work. But the second was actually moving brokerage into mobile, which also hadn't been done. And I think we were, we made the right bets there because zero commission ended up being the industry standard and. And brokerage moved to mobile as as primary. And actually, every brokerage of consequence, every platform that lets you trade stuff

• 42:13Speaker 04

  had to resemble Robinhood in order to to stay relevant. So to some degree, I don't want to take too much credit over the design. I mean, we had a great team of people. Beijou obviously cared a lot about it. I think I think we had that culture set up from very early. But what I tell you is when I work with designers now, and you mentioned the gold card. I think the gold card is a product that hopefully, Raul, you can see there's a lot of intentionality in in the design of it, not just, you know, the physical card itself, but also the the credit card app with the way that we do virtual cards, family features, the way that like

• 42:57Speaker 04

  the app looks and feels, it's kind of got this monochromatic gold vibe where we tried to deliver the feeling of using a luxury kind of high net worth product, but but simultaneously make it accessible to the mass market. So we care a lot about this. And, you know, when I meet with our designers and creative folks, who I spend a lot of time with, I kind of tell them two things. The first thing is everyone should be a craftsman and like use the tools like the and the tools are so good now. I mean, you have mid journey. Design has been democratized and made accessible to a tremendous degree.

• 43:41Speaker 04

  And I think there can be a tendency, especially as organizations get bigger, to have like your VP, your senior director, your director, passing your feedback down in a big chain. And then there's like one designer at the end of it, an individual contributor who's doing the work. And what I tell people is everyone should be doing the work. There's no reason not to. Like, I love it when when my designers and creatives take out Figma or or take out mid journey in a meeting and just start start working on stuff. And I try to encourage that myself by doing it as much as possible. So so that's one thing. And then the second thing is I think I think one failure case is when you have big teams of people and multiple creatives,

• 44:24Speaker 04

  you end up getting these big meetings and you end up seeing designed by committee, right? And everyone kind of like throws in their two cents of how things should be changed. And you end up getting something that doesn't offend anyone, which I think is not the recipe for for getting the best design. I think the best design is opinionated. It's gonna it's gonna offend some people and there's gonna be like a lot of conflict around that. So another thing I tell people is it should be opinionated. You know, if everyone has consensus, then then we're not there. You should you should see it and have like an emotional reaction to it. And actually, we have to figure this out.

• 45:06Speaker 04

  If it if it if it involves kicking people out of meetings, if it involves being explicit about like, hey, this one, I'm running with the vision, maybe this other one you should. But but I think what kills great design is is sort of like large numbers of people designing things by committee. And you have to fight against the grain to make it feel like a consistent coherent vision, ideally from from one person. So those are kind of the two things that I that I think are hard and non-obvious that

• 45:42Speaker 04

  that I think are necessary and I emphasize as much as I can.

• 45:46Speaker 01

  So I'm just gonna jump in and riff on that a little bit. First of all, by the way, Jason said you are a genius and I didn't know that you went to Stanford. I didn't know that you started in physics. Folks, anyone who starts in physics and says, this is too easy. I'm gonna do math instead. Oh, my God. So I was I was at Cambridge and I was surrounded by very smart people, of course. I did computer science and then the physicists and the mathematicians, holy moly.

• 46:12Jason Calacanis?

  But then he decided, Raul, to do the ultimate boss, which is try to build a consumer product, which makes physics and computer science and everything else seem easy. Because now you're into just strict art and science and alchemy.

• 46:29Speaker 01

  Well, you know what it turns out? It's that that left brain, right brain thing, which which Vlad, I sense in you as well. I find that relatively easy. But and maybe if you have a physicist mind or a mathematician mind, it feels that way. But Vlad, my question was going to be, I mean, you've you had such a success, you've scaled your organization much further than Superhuman is right now, and we hope to be where you are at some point. How have you how have you scaled the teaching of design? So I think we've, you know, we've heard things like, don't design by committee. But the actual nuances of the craft and what makes Robin Hood, Robin Hood? How have you taught those pieces to people? It's something that honestly, I still struggle with sometimes, and I solve it by jumping in there myself.

• 47:15Speaker 01

  I hired a president last year. I've gone from eight direct reports, the normal VP structure down to two. So I'm in there pushing pixels and writing copy with everybody. How have you done it?

• 47:23Jason Calacanis?

  This is such a good question. Yeah, professional development.

• 47:26Speaker 04

  Yeah, I mean, I think I think it starts with great people, people that you trust, being in leadership positions where they have influence. We've gone through this as we've grown the company and the design team where, you know, the first go around, we hired some professional managers that, you know, were kind of further from the work. But I think the balance we've reached is the people that are the best at the work, whose taste we trust the most are in leadership positions. And then, you know, they're kind of, they're kind of pushing things forward. And you kind of supplement, I supplement that with being in meetings with them, being in jam sessions with them.

• 48:09Speaker 04

  And meetings are not just forums where we review the work, but we actually do design in meetings and actually change things.

• 48:18Speaker 04

  With remote, it's been difficult. I think I always prefer to have people in one place where we can,

• 48:25Speaker 04

  we can draw stuff and we can kind of go back and forth. And we've done some like multi-hour, half-day jams in the past. Um, well, yeah, it hard for me to, to, to compare against other companies. I've, I've never worked at another company, but um, it's not a clean process. It's, it's, it's messy. I think sometimes we end up taking too long to do stuff and we redo everything and start from scratch and everyone gets frustrated. So I'd always love for it to be cleaner, but um, I think, I think Rick Rubin's book, I don't know if you guys have read Rick Rubin's book. It's very good. Um,

• 49:03Speaker 04

  yeah, I think, um, I mean, we're, we're in the technology product business. So I don't think we're quite there in Rick Rubin land where I mean, his thesis is like, it's good if you like it. And the artist is kind of a singular individual. I think we have to juxtapose that with it actually has to drive business results. There's metrics, it has to perform.

• 49:23Jason Calacanis?

  Right.

• 49:25Speaker 04

  But uh, but I, I think, I think there's a, there's a lot of truth in that book.

• 49:29Jason Calacanis?

  You know, it, it takes slowing down too, Raul. So in our venture firm, I looked at how do we get my decision-making process that led to investing in both of your companies? And how do we scale it? Right? And at the time I met people through my network, uh, or I found a great product and I just emailed the person as in your case, Raul, I like to report if I emailed the info line. That was my original philosophy. Um, you know, I, I was the picker and people said, oh my God, you're such a great picker. And that's how I went from, you know, being the first scout at Sequoia with another kid named Sam Alkin. Uh, he did Shrip, I did Uber. Uh, it's pretty funny. Uh, and then having my own fund.

• 50:10Jason Calacanis?

  Then I went on, um, to really focus on building systems as opposed to just having the goal of like, I want people to pick as good as me. Like, what is the system for doing that? And the system for doing that is actually understanding the founder's vision, right? And how does that occur? It occurs in a meeting, it occurs with a demo. And then I broke down, what are the items that Superhuman, um, Uber, Robinhood, Wealthfront, what data stacks, Thumbtack, Athena? What were the things they had in common? And they were always world-class design was one of the 13 attributes. World-class design. So that's one of the 13 attributes we put into our database system when we're vetting 20,000 applications for funding per year.

• 50:56Jason Calacanis?

  Another one is product velocity. Another one is the team worked together before. Now, if you look at both of your companies, Superhuman, you had people from the previous team, right? So it was a serial team and it was a serial founder. Serial founder, another one. Robin Hood, not a serial founder. I don't know that you had a company before it, but you were a serial team because you hadn't worked together.

• 51:16Speaker 04

  We did, yeah. We had a company, but it wasn't venture-backed and it was like a moderate failure.

• 51:22Jason Calacanis?

  Great. So that counts, right? So you were a serial team, world-class design, and you had product velocity. And that last one, product velocity, if a person can release product on a regular cadence, they're going to learn so much more than other firms. And so we just slowed down and we've been working on this database and the system for, I don't know now, three years. And it went from like five attributes to 13 of why we would invest and then about 40 reasons of why not to invest. That could be minor things like there's a lawsuit, there's an accounting problem, there's a broken cap table. And those can be, you know, red flags or pink flags, as we say.

• 52:01Jason Calacanis?

  But I think, Raul, building systems to have knowledge trickle down into an organization that was three people when I started, me and Ashley and Jackie, to now 21, 22 people, processing previously, you know, 2,000 companies a year and now 20,000. That's the key is can you build a system? So I wonder if you've built systems to take the knowledge and philosophy you have, Raul, what is the system for getting it out of your head and into their hearts, you know, and into their instincts? Your instincts to their heart.

• 52:33Speaker 01

  We have. I think systems work well. I mean, this is me talking about what I know less about. Obviously, it seems easier to describe somebody else's job. But as an investor also, I, we have not 13 attributes. I think we have seven or eight that we run through in our fund. I think where it gets really different when designing a product is it's so subjective. And you're deliberately, in some cases, Vlad, like you said, trying to offend people, or at least make sure that you haven't created something dilute which everyone said yes to. And it's the subjective stuff that I sometimes find hard to translate. And I can always do it in retrospect.

• 53:13Speaker 01

  So for example, I see a design and I'm like, okay, we're going to tweak it in XYZ way.

• 53:21Speaker 01

  My internal thought process is, I just know. I just know why we have to make the change. And then when the team asks me why, I'm able to rationalize it. I'm able to say, well, this doesn't line up with that, or there's not enough white space here. Or, you know, we can't have transitions. Everything needs to be instant, which is one of the unusual choices we've made in our interaction design. And some of those are principles, but some of those are you just know, and I'm retroactively rationalizing it. And my hope was that after 10 years of doing that, you know, you come up with 100 or 200 rules, retroactively rationalized rules. But there always seems to be a few more, some that aren't missing. And maybe we just need to keep on doing this.

• 54:00Speaker 04

  I love the, I love the transitions thing. Yeah, I care a lot about that. The engineers and design folks all know that like, when I see a spinner in the app, I just lose my shit. I'm like, how did the spinner get here? I'd rather the app crash than to actually see it.

• 54:19Speaker 04

  But yeah, I think it's the small details. And one thing I'd add, we still do all hands weekly as a company where, you know, I talk, I talk in front of the company, answer questions. I don't think very many companies at our scale do it. We definitely push for that.

• 54:35Jason Calacanis?

  That's every Friday you do it, your little wrap up.

• 54:37Speaker 04

  Yes, and Jason has generously volunteered to emcee my all hands.

• 54:42Jason Calacanis?

  Cannot wait to come.

• 54:43Speaker 04

  You're emceeing my all hands in April, or possibly earlier.

• 54:47Jason Calacanis?

  Cannot wait to come and meet everybody and tell them some of the historical stories. Let's talk about feedback. Feedback to overindex on, feedback to ignore. When do you overindex? How do you collect information? How do you, let's start with, how do you collect information? What do you overindex on? What do you, what do you, you know, de-index? What do you, what do you, you know, what's the word here? Overindex on and maybe dismiss.

• 55:14Speaker 04

  So we really overindex on actual feedback from customers, both quantitative, like you're looking at the data of them using it and where they're dropping off, and qualitative, where, you know, we put prototypes or actual working product in front of customers. UX research we did and we continue to do very early.

• 55:40Speaker 04

  What do I underindex on? Focus group style settings where you're asking people if they would use a certain product, if only it existed, or if only it had some feature that you're kind of describing generally. I think there's so many times where someone will tell you they'll use a certain product, but they wouldn't actually do it if it came down to it. And what people say that they'll do doesn't always match up with what they do when you've got the product in front of them. So I think you have to be careful in some sense with focus groups and with people going over prototypes or value props.

• 56:22Jason Calacanis?

  Open-ended feedback can send you on a, you know, random side quest, and the person would actually never use the product. And it's almost better to just build a prototype and actually have somebody use it or look at the data. Yeah, I agree with that. What do you think of getting feedback, Rahul, and then overindexing and ignoring?

• 56:45Speaker 01

  Well, as you know, I'm very opinionated on this topic.

• 56:48Jason Calacanis?

  Yes.

• 56:48Speaker 01

  Have written and talked about it extensively. If folks want to see that, check out Superhuman: How We Built a Product Market Fit Engine. That's on First Round Review. I believe it is the most shared article of all time, which I'm very proud of. I'll do a very quick summary. It's quite detailed, but the quick summary is, this is really hard, especially when you're in the earliest stages of an application or a company, you're trying to find product market fits. The risk is that even if you listen to your users or your customers, that it will give you a... A very kind of muddy, dilute view of what they want because they all may want different things out of your product.

• 57:33Speaker 01

  A really old fashioned example, but this is the one that I originally read over a decade ago is, hopefully some folks remember that PayPal started as a mobile way to transfer money as opposed to a web way to transfer money. Imagine you're polling those two groups of users. They're just going to give you two completely different sets of feedback. And if you just start acting on it, let's say in in numerical order, you're going to end up building sort of a very messy, muddy product that lacks coherency and vision. So what do you do? Well, there's this guy called Sean Ellis, who actually coined the term growth hacker. And he found that if you ask people a very specific question, how would you feel if you could no longer use the product? Give them three choices, very disappointed, meaning they love it,

• 58:18Speaker 01

  somewhat disappointed or not disappointed, and measure the percentage that say very disappointed, meaning they love it. If you find that you get 40% or more people saying that you have early product market fit. And he found that those companies, this is benchmarked against hundreds of bench back startups. Those companies almost always find their way to at least some degree of success, hundreds of millions, if not billions of dollars of success. So what I did was I took that and built this algorithm or an engine around that to try and figure out, who do you listen to? Added a few more questions. Question next is, who do you think this is best for? How can we improve the product for you? And what do you think the main benefits of the product is? The main benefit is super important.

• 59:02Speaker 01

  So we asked this in the early days of Superhuman and obviously predictably we got all kinds of answers. But there was a contingent to people who were saying the main benefit is speed, keyboard shortcuts, focus, design, aesthetics. Ultimately, it's speed, like this thing that's just really, really fast. And if at the time I told you, yeah, I'm going to build an email app and the core value proposition is going to be speed. Then you, Jason, you were like, okay, fine, I invest. But most people were like, no, that's a crazy idea. Yet here we were with our customers, some of them validating that. Now, the key thing is, and this is hard to do, but. Discard, ignore the feedback from all the people who said the key value proposition, the key benefit of the product was not speed, or whatever the main one is in your case.

• 59:46Speaker 01

  And by doing that, you can focus on the people who really get your vision. Now, there's more nuance, there's more detail, and you can actually turn this into a metric that you can optimize over time, but that is my quick summary of the method.

• 1:00:00Speaker 04

  Can I, can I ask you a couple of questions? I tried, or I went through the process to attempt to onboard to Superhuman as, as I was on my way over here. And I noticed something, which I'm sure, based on what you just said, you have a very nuanced take on, and it's subscription gating, right? So, a lot of products, they put the subscription gate in different parts. Robinhood has a subscription element to Robinhood Gold, as you know. I noticed with Superhuman, the subscriptions like right out front, you basically can't even see your email unless you already sign up. Is that something you guys tested? Or was it that way from the beginning?

• 1:00:43Jason Calacanis?

  He tested it on me!

• 1:00:45Speaker 01

  Oh yeah, I did. I did, actually.

• 1:00:47Jason Calacanis?

  Tell him the story! This is the, this is what I knew I invested in the right guy.

• 1:00:51Speaker 01

  Yeah, okay, so, um, so a little bit of context and a little bit of history then to make the story make sense. We used to onboard every single person in person, and I did the first several hundred myself, including Jason. And the very first thing I did when I sat down with Jason and all these other folks was, so as a reminder, this is a paid product, and no one gets it for free, especially not investors. That's how I'm going to keep us intellectually honest here on your feedback. And he goes like, "What?" And I was like, "Yep, time to pull out your credit card. Here's a little Stripe payment form. Put it in, please." And I sat there watching him pick his credit card. I did that hundreds of times.

• 1:01:32Jason Calacanis?

  It was so great. What, can you imagine? You're the first investor in the company. He's, it's a year later and he's finally ready to show it to me, or whatever, six months later. Like, I think we were at Cycles getting espresso or something in San Francisco, and he's like, "Okay." So you log in and like, I'm over the shoulder, and he's like, "Okay, now you take out your credit, put it in." And I was like, "Yeah, okay, so yeah, how do I skip this?" And he's like, "No, you actually put your credit card in. It's a dollar a day. It's 365 days, you know, and I'm like..."

• 1:02:02Speaker 04

  It's kind of expensive.

• 1:02:03Jason Calacanis?

  I was like, you know what? A moment of truth. This thing better save me a [bleep] hour a day on my email. And it did. But this is such a great onboarding device. And now so many founders, Vlad, come to me and Raul. They come to me and say, we're doing the Raul onboarding. And this is when you know you've hit a product note. People will say, we're Robin Hood for X, we're superhuman for Y. And then if they can drill down and they know the product technique, like, we're doing the give to get from Dropbox or Uber, you know, or the, you know, what Vlad did with, with shares. Which by the way, I broke the give to get share thing. Did you know that?

• 1:02:43Speaker 04

  Vlad? You got to, you maxed it out?

• 1:02:45Jason Calacanis?

  I maxed it out because I would tweet, hey, if you haven't tried Robin Hood, it's [bleep] fantastic to whatever quarter million people, a half million people. And when that happened, I would get 100 shares. Now these were like, you know, $3, $10 share. When I hit, I think 250 or 500, I sent you a note. By the way, I broke the system. I guess there's a cap. And the cap was you could only get paid for 500, which I think was because people were hacking the give to get system. So let's shift the discussion to acquiring customers. What, Raul, have you done to acquire customers? What's been the most effective? What did you think was the most effective and didn't work? You know, and how do you think about customer acquisition costs broadly?

• 1:03:25Speaker 01

  Super important question. So in the early days, we had three pillars and I, I always believed these pillars would work for us. And number one is virality. Number two is PR. And then number three was thought leadership. So when it comes to virality, this is probably the least surprising, but with email, one of the most effective. Email is one of the last true.

• 1:03:52Speaker 01

  One of the last few truly viral places where you can build a product. And it's the obvious stuff, like for example, sent by a superhuman, which I think thirty, forty percent of our users actually have on. We've sent many, many hundreds of millions, maybe even billions of emails with that in it. And to this day, it still drives between thirty and fifty percent of site traffic, depending on the month. So that actually still works, surprisingly enough. But then there are some less obvious things. So like with Robin Hood, like with many companies, one of the biggest flywheels for driving new users is just users inviting other users, right? Whether it's to join their team or to be another individual subscriber.

• 1:04:33Speaker 01

  Here's the thing, as an email app, we get to literally send the email as the user. So we punch through privacy inbox, we punch through focused inbox and Outlook, we're right at the top of the other person's inbox.

• 1:04:45Jason Calacanis?

  That is so slick. Yeah, so slick. So it's because the from, just so founders who are listening, understand this. Because the from is not from Robin Hood or from superhuman, it's from that actual customer. You know, they are obviously friends with the person, so it goes straight through. It's so brilliant. Yeah.

• 1:05:06Speaker 01

  Yeah, yeah, exactly. So that was pillar number one. Pillar number two, I think I said was.

• 1:05:10Jason Calacanis?

  PR.

• 1:05:11Speaker 01

  PR. Yeah, so this is sort of generic advice, I think, for every founder that I give at the early stage, which is, depending on your industry, something will happen that is really news and noteworthy at some kind of a cadence. In the email industry, it's like, you know, maybe once a year, there's some interesting email thing that's going to happen. And I remember it happens relatively early in superhuman. Folks may remember the app Mailbox, and that was a hundred million dollar acquisition by Dropbox. And they popularized swipe to archive, like a really, really great innovation didn't exist before that, believe it or not. Now every single app has that, obviously. But Dropbox acquired them and predictably, but sadly, a year and a bit later, they were shut down.

• 1:05:55Speaker 01

  I'm not going to get into the reasons why, but they were shut down. But I could see it coming a million miles off. And I was like, aha, this is my moment. Everyone is going to cover this very, very sad outcome, burning of a hundred million dollars. And then that itself is going to start to trigger mainstream media to start writing about email all over again. And this happens once every few years. This is my, this is my time to shine. So I was like, okay, what do I have that is personally relevant to this story? Well, I sold an email company, but you know, I sold my last one for 15 million. So no one really cares. It's really tiny. That said, I worked at LinkedIn for two years and I think I have an extremely detailed and nuanced view of how to make an acquisition work really, really well. And even today, Reporter is still alive.

• 1:06:40Speaker 01

  It's part of LinkedIn Sales Navigator. And for an acquisition to have survived 15 years is just super rare. So I know how to do it. I, I, I sort of created the foundation and the framework for that to work. So what I did was I wrote what is to this day, still one of the most shared articles on how to survive an M and A transaction and not just how to survive it, but how to thrive in one and how to make a real impact at the acquirer. And so I just piggybacked my article on their news and that drove many tens of thousands of new signups to Superhuman.

• 1:07:15Jason Calacanis?

  Tens of thousands. See, this is interesting. There's actually a term for it. When I was a journalist, they called it news hijacking. And the PR industry now, it's kind of part of the playbook. You can get pulled into it as Vlad did inadvertently, you know, without doing it, or you can do it actively, you can do it passively as Vlad did. We'll get into that story in a moment. Or you can get, you can do it, you know, deliberately. And you see this now where people are like, oh, if you're talking about, you know, Doge, I have an expert at doing zero-based budgeting from the accounting firm of Lux Lux and Lux. And they can comment on it. And, you know, there's like helper reporter kind of services.

• 1:07:59Jason Calacanis?

  Vlad PR played a major role for Robinhood at various points, also for Uber. And sometimes even if it's, you know, the, the bad press is good press kind of situation. The number of signups for Uber, every time something went wrong in an Uber, you know, an Uber accident, you know, anything, even with the company, the.

• 1:08:24Jason Calacanis?

  I mean, I don't, I gotta say this judiciously, but it, no matter what happened, it moved Uber up in the app rankings. The number of people signing up for Uber on a bad news day, when everything was chaotic, were the record days. Vlad, do you have any experience in this regard?

• 1:08:43Speaker 04

  I do, several. And by the way, I just wanna, just wanna plus one mailbox. Mailbox, uh, maybe, maybe you guys know this, but inspired the initial Robin Hood waitlist. We had close to a million people pre-launch sign up for Robinhood. And we introduced a mechanic where, uh, if you invite someone that joins the waitlist and they accept, you get, you get priority. So it was, uh, it was a prioritized queue where if you invite successfully someone, you, you get bumped ahead.

• 1:09:16Jason Calacanis?

  Oh, right. I remember that. We talked about that when you were here, uh, in 2017, one of your first appearances. You talked about that waitlisting and somebody productized that, I think. There's like a product you can buy now instead of having-

• 1:09:27Speaker 04

  Branch metrics.

• 1:09:28Jason Calacanis?

  Yeah.

• 1:09:29Speaker 04

  Branch metrics.

• 1:09:30Jason Calacanis?

  There's been productized that pack, yeah.

• 1:09:31Speaker 04

  They, they came, uh, later and they told me, hey, the, the Robin Hood waitlist was a inspiration for, for our company, which, which I thought was amazing. I'm sorry, your question was PR. So I, plus one on virality. Um, yeah, PR, um, yeah, I mean, I, I think that just building the motion and knowing, um, how to do it, it's, it's earned media, right? So you don't have to pay. It's not like paid ads. Um, and I, I think that, I, I'm not sure how much it moves the needle, uh, quantitatively when you're at large scale, but, uh, and there might be some correlation where, you know, founders that go and get press just tend to be founders that hustle anyway.

• 1:10:16Speaker 04

  It's like, I gotta get users, get me users however I can. Virality, I'm gonna email everyone I know. I'm gonna email all the reporters I know. You just try everything and eventually by, by, by the nature of like trying a lot of things and being relentless, even if a small percentage of those things work, if you're just moving faster and iterating, um, it'll work quite well.

• 1:10:40Speaker 04

  We did, we did have a lot of learnings in, in PR. Maybe you're talking about the whole GameStop thing, but, but even before then, like 2019, I remember this crazy thing that happened. We, we went viral on Reddit because there was, uh, there was a trader on Wall Street Bets that discovered the, um, infinite money, the Robinhood infinite money glitch. I don't know if you guys remember hearing about this.

• 1:11:05Jason Calacanis?

  I remember this. Yeah. The money glitch. Yeah.

• 1:11:07Speaker 04

  Yeah. So, you know, he posted a, a video of, of him screencasting his, his infinite money glitch. And of course, you know, the team at Robinhood was like freaking out. It's like, how many people do we have exploiting this? We got into action immediately. We were, um, we were, we were like making plans to close the loophole, look at all other types of loopholes. And it was a trivial number of people that actually went through with it, right? Maybe like dozens or, or something. Um, so it didn't end up being a thing, but everyone saw on Reddit and the internet that Robinhood had an infinite money glitch and they were like, oh, I can make infinite money,

• 1:11:49Speaker 04

  uh, using this app. And, and so growth, uh, basically spiked up ju- just from that. So, you know, we, we were, we were, we were terrified of this thing and then it just ended up, you know, benefiting us in, in all sorts of strange ways.

• 1:12:06Jason Calacanis?

  Uh, let me drop you off, Raul. This has been amazing. What a, what a delight to have you both. And then Vlad, I'm just gonna say a couple of questions about, uh, Robinhood as we wrap here. Uh, thanks again.

• 1:12:15Speaker 04

  Great to meet you, Raul.

• 1:12:16Speaker 01

  Yeah, I'll hit you up about the gold card and, uh, Jason, thank you so much for having me again.

• 1:12:20Speaker 04

  I'm gonna finish my onboarding.

• 1:12:22Jason Calacanis?

  This is great. Uh, I'm gonna have, I'm taking you both out for a steak when I'm in San Francisco. I, I will, this will be to, to be continued, this little trio here. Hey Vlad, I wanted to talk to you just about the swings and the value of the company and running a, a public company that comes down to like, I think I bought more, I tweeted it the other day. You know, I'm, I'm just such a fan of the product. I make my decisions based on product, you know, founder and customer.

• 1:12:49Speaker 04

  And I love that you haven't sold a share.

• 1:12:51Jason Calacanis?

  I mean, why sell a share in something I think 10 years from now will be worth 10x? Like, I think that you will be a trillion-dollar company eventually. I'm talking my own book here, but it's a fraction of my overall, you know, net worth. So like, I don't want to make it into bigger than it is, and I don't like to pump stocks or anything like that. But when I make a decision to own a company like Berkshire Hathaway, you know, and Warren Buffett has a thesis. My thesis is the team, the product, the customer. Here you got a team that I've always believed in, that has executed at a high level since day one. You have a product that if you use it, you know it's delightful and best in class. And then you have, third, a customer base that is growing and loves it. You see that from the hood conference you're doing, but there is a reality.

• 1:13:35Jason Calacanis?

  When this company went public, I think it went $67 a share then during this down draft. And Silicon Valley Bank going down and went down to maybe nine or 10 bucks. I bought more shares in the company when it was at $10 on my Robin Hood account. And, you know, here we are, it goes back up 40, 50, 60. I don't look at it day to day. I look at the trend of, hey, the revenue is great, customers are great. But you have to run the company through those things. How do you, how do you stay even keeled? And what do you focus on every day? When the company has shifted in value by 6x in the last three years? I think it's 6x, try to peak.

• 1:14:11Speaker 04

  It's obviously much easier on the way up than the way down. Just psychologically for folks, right? Like, the volatility is not the same on the way up. Everyone's feeling good. And, you know, what I worry about there is complacency, right? It's like, you think you're winning because the number's going up. And then the conditions of being too complacent actually set up the scenario where if you're not careful, it could go back down again because you've got your foot off the gas. So I always try to temper. I mean, I think it's good to reflect and celebrate and actually see that we've been making progress

• 1:14:52Speaker 04

  or getting rewarded for the progress, but also temper that with an understanding that we've got a lot of work to do and the job's not finished. You know, the job's not finished, you got to keep going.

• 1:15:03Jason Calacanis?

  Yeah, that's the Kobe line, right? Job not finished.

• 1:15:05Speaker 04

  Yeah.

• 1:15:05Jason Calacanis?

  Why would I be happy? I love that quote. Um, and Kobe is just, is he, is he like an inspiration for you? You, you a Kobe guy?

• 1:15:12Speaker 04

  Hundred percent. Yeah. I was, I was fortunate enough to meet Kobe at a, an NEA event. When, uh, yeah, I think he, he came to Sausalito at the Cavalo Point and, you know, we were, we were, uh, I think maybe a series C stage company. This was back in 2017 and Bejor and I had a meeting with him, a business meeting. And of course I just wanted to talk about basketball. I was, I was a huge fan. And I was like, what's, what's gonna happen to LeBron? He said, LeBron's gonna go to the Lakers.

• 1:15:42Jason Calacanis?

  Oh, inside information. He had the trade ready to go. He knew.

• 1:15:46Speaker 04

  He knew it. He knew, he knew LeBron was going to the, the, the Lakers. So, um,

• 1:15:50Jason Calacanis?

  I mean, there's, Chris Saka had a meeting with him and he talked about it. He, and it, it's so sad that he passed away so young because he wanted to make his third act, being an investor in companies and technology and company formation. And he was around the basket, applying his same discipline, from what I understand, to learning our crap in the way that he, you know, approached basketball. And there are these amazing stories of people like, he would invite them to a workout at 6 a.m. So people would be like, oh shit, I gotta work out with Kobe. Let's get there at 5:30. They would get there at 5:30 and Kobe would be sitting there having breakfast and they'd be like, oh, you having breakfast? But he was like drenched in sweat and they're like, yeah, he had his first workout at 4 a.m.

• 1:16:33Speaker 04

  Yeah.

• 1:16:34Jason Calacanis?

  It's 5:30, he's having breakfast and you're coming to the second workout, mofo's. This is, and he saw people, there was this other one, they were coming back during the dream team. And they're coming back into the hotel. They went out to a club and it's 4 a.m. And they're coming back to the club. He didn't go to the club. He was leaving the hotel to go to the gym and they're crossing in the lobby. And this is in the off season. And the people wonder why this guy just was such an incredible winner. It just all had to do with that, Brett.

• 1:17:01Speaker 04

  Yeah.

• 1:17:02Jason Calacanis?

  Technique, effort, strategy, all of it, philosophy, and the systems he built, right? The system he built for success, you know, was studying the game, right? He studied it and he was hard, you know, like, and when you play with Dwight Howard, you ever see that where he calls Dwight Howard soft? He was super frustrated by Shaquille O'Neal's preparation for games. And he was super upset about Dwight's because sometimes the big guys in basketball, they fall back on their size, right? Their physical attribute is what they fall back on. He didn't have that. He was six, seven or something. So he had to actually go with technique not being seven, one. Tell me about the desktop product. This seems like you're like, I think most people who do desktop use Bloomberg or Interactive Brokers or something like that, right?

• 1:17:46Jason Calacanis?

  These are like the super pros. But you started mobile first and now you have the desktop up. How's it doing? What percentage of people use it? Why do this now in year 10? Tell me about the thinking and how it's going.

• 1:17:58Speaker 04

  Yeah, yeah, it's going well. We announced at our last earnings call, the Robin Hood Legend, which is our first desktop product built specifically for active traders, was already at 50 million in revenue run rate. And it's after basically two months, two months of being out.

• 1:18:15Jason Calacanis?

  What does it cost?

• 1:18:16Speaker 04

  It costs nothing. Yeah, no additional cost.

• 1:18:19Jason Calacanis?

  So 50 million has been generated in trades from it or revenue from it?

• 1:18:24Speaker 04

  Yeah, yeah. And that's, that's basically just the transaction revenue. We're not even, you know, counting what may be incremental margin revenue or interest, which so, so, um, yeah, we feel pretty good about that number. And obviously if it's that way after two months, it's on its way to being a hundred million business in and of itself. And I call them cylinders, you know, we, we went from each, each hundred million dollar business line, I like cars, so is a cylinder for us. So, so now we're a nine cylinder engine. When we went public back in 2021, we had, you know, maybe three cylinders, something like that, options, crypto, equities. So the business has gotten much more, much more diversified.

• 1:19:07Speaker 04

  In 2021, we look back at the initial euphoria after we went public. It was a little bit of a weird IPO. Our stock actually went down on IPO day. So it was kind of a stressful day for me and it went up. As you mentioned, you know, the seventies, the week after, yeah, it never felt real. I mean, I felt very fragile in a sense because I didn't feel like I had earned that valuation at the time and the business wasn't diversified. It was very much relying on a zero rate environment. And so you ask about, you know, the peaks and valleys. When we went through 2022, the higher rate environment, the business normalizing, us having to adapt to not having easy money,

• 1:19:50Speaker 04

  not relying on that. It was very painful at the time, but it actually planted the seeds for us diversifying the business, becoming a stronger company, getting the team in a much leaner, better shape. And it's sort of like set up the foundation for us to be, for us to be successful last year and, and you know, so far, so far this year.

• 1:20:11Jason Calacanis?

  If you think about it, you know, in this basketball analogy and as a player, you know, the big men, Shaquille O'Neal, you know, they rely on their dominance in the paint because of physicality. Okay, that's one dimension. But if Shaquille O'Neal became a decent free throw shooter, given the amount he had fouled, he would have been even more dominant. He never got that right. And now you watch today's game, you have somebody like Porzingis, Kevin Durant.

• 1:20:34Speaker 04

  Jokic.

• 1:20:35Jason Calacanis?

  Jokic and Karl-Anthony, SGA, Karl-Anthony Towns on the Knicks. Karl-Anthony Towns on the Knicks is a four or a five. He's playing a five right now. He's the greatest big man shooter ever. I mean, his shooting percentage from three was like over 40% for much of the year this year. And so when you have a big man, imagine if Shaquille O'Neal could hit a three. And then you start thinking about two way, if you can defend and they, you know, they call them what three and Ds, you know, people can hit threes and who can also defend on the other side. You're starting to get these players and then assists come in and you got big men like Jokic, uh, who can actually pass. And it's like, whoa, wait a second.

• 1:21:11Speaker 04

  Jokic averaging a triple double as a big man. I mean, I think I was reading somewhere that Jokic statistically is having the best season ever by any basketball player this year.

• 1:21:22Jason Calacanis?

  That's crazy. And then you look at the guy and his physicality compared to LeBron, compared to Kobe, you know, Maybe he's even got another card he can turn over, which is imagine if he had LeBron support staff with him and he physically.

• 1:21:37Speaker 04

  If he got jacked.

• 1:21:38Jason Calacanis?

  If he got jacked. I mean, I'm not saying he's a doughboy or anything like that, but people do say that like, my God, look at him. He doesn't look like a basketball player. I mean, if he, if he gets physically dominant, oh my God, he will be the best player in the history of the league. It would be absolutely crazy. So. And you know, it's interesting. I saw this as well with Uber, um, when they had the eats business and then COVID hit. You know, rides goes down, eats goes up.

• 1:22:02Speaker 04

  Totally. Yeah. Yeah.

• 1:22:04Jason Calacanis?

  And now you're resilient. What happened to Airbnb where Brian, you know, God, if we had Brian Chesky on this with me, you and Raul, can you imagine? I mean, he's another master of, you know, just this whole alchemy of like figuring out product and how to run and scale a company and how to do the finance part. What an amazing, um, you know, journey they've had because he overstaffed a little bit like you did probably. And then he cut and cut and got it really tight. He does his two cadenced product releases a year. And but man, when they hit COVID, he told me on this very program, like he wasn't sure about the future of that business. Like. They went to zero revenue. Can you imagine going to zero revenue? Now, the one thing they had in their favor was they were asset light.

• 1:22:48Jason Calacanis?

  They didn't own the properties and people have pushed him to start owning properties.

• 1:22:52Speaker 04

  Yeah, yeah.

• 1:22:53Jason Calacanis?

  You're having exclusives on properties and he never did it. So they didn't at least have the hard costs of those things. But what, what do you think of Airbnb as a business?

• 1:23:01Speaker 04

  I mean, like his headwind became a tailwind pretty quickly because I actually, I'd say, you know, back then, March 2020 hit. And everyone was freaking out. It was like shelter in place. Don't leave your house. But then by, you know, by May, everyone was like, I'm kinda. Tired of being in my house. I mean, we, we did this. We're like, can we shelter somewhere else? And then I think Airbnb became suddenly very, very attractive, right? So.

• 1:23:31Jason Calacanis?

  That's so interesting too. He turned the lemons into lemonade because we went from you can't leave your house to you can leave your house. You can get on a plane. But you can't, you can only have this many people. At the house, so you got to make a pod, right? What do you think of all this dough stuff? I'm curious because you had to, what was the peak employee count? And when you did your reorg, where did you get to? And then when you look at what's going on in Washington, what do you think?

• 1:23:52Speaker 04

  So I think our peak employee count was probably end of 2021. We were at about 4,000 people. And we got down to maybe a little bit over 2,000. So, yeah, it was, it was large.

• 1:24:05Jason Calacanis?

  What was the difference between the, the two staff sizes? If some people report that things are more efficient when you have less.

• 1:24:11Speaker 04

  Yeah, absolutely. Yeah, we, we saw that directly. And at that time, you know, we also reorganized the business. I went to GMs and business leaders who were, who were owning their P and Ls. But we, we moved much faster. We move much faster now. And I think, you know, the, the reality of it is it happened during COVID. End of 2019, I want to say we were under a thousand people. We quadrupled basically during COVID. These people hadn't met each other in person. They were just on these Zoom calls. So there were a lot of confounding variables that I think would force us to not work particularly well together. So we, we ended up reversing all of that. And, you know, you see the product velocity, the accountability, the, the performance of the company.

• 1:24:55Speaker 04

  We had to learn how to do this, but it's, it's true what they say. I mean, I think that the company was frankly overstaffed and we got ahead of ourselves. We got, we got too loose. We were always a very lean company and we, we, we, we always strive to do more with less when we were private. And we got a little bit away from that. So when, when I think about the federal government, and I've got a lot of friends that work at the federal government. You know, I'm, I'm in DC right now. I grew up here and, you know, they're very nervous right now as they should be because they, they see what's happening.

• 1:25:29Jason Calacanis?

  Yeah.

• 1:25:29Speaker 04

  But I, I think it's tough medicine. The country needs it. I think the deficit is the biggest problem that we have right now. And I'm glad that the, the administration recognizes that. And it seems like the people are behind it. I think that, you know, it's, it's, it's, the medicine is going to go down tough. But I think there's so much waste that.

• 1:25:48Jason Calacanis?

  Pretty clear, you know, anytime you have.

• 1:25:50Speaker 04

  Yeah, there's so much that needs to be.

• 1:25:51Jason Calacanis?

  You're a nimble startup and you had waste, you know? So if you can admit it, I think we can admit it in the government. Let's end on crypto. We went from a regulatory environment where, you know, Gary Gensler was like, we have a playbook here. We got rules here. Follow the rules. Seems reasonable in some ways, but the truth is, these things, when you say crypto, or a person says crypto, not you specifically, but when a person says crypto, that can mean a trading card in NFT, it could mean a DAO, a group of people investing money together, i.e. like a venture firm, it could mean a meme coin, it can mean a utility token that gets burnt as you do usage. Man, there are so many different ways, you know, that

• 1:26:33Jason Calacanis?

  you could be involved in this. So what should happen in crypto? What would you like to see? Because you have people trading on your platform. What would be a reasonable solution to what feels like to me, we had no rules, so it was too hot, then we had, you know, follow the existing rules, too cold, now we're back to too hot, in my opinion, with like the Malay coin, the Trump coin, whatever, you know, probably need a little more reg. What should David Sacks do? What should the future be? How should the SEC look at this? And what would you like to see? Because you're directly impacted by it.

• 1:27:06Speaker 04

  Yeah, absolutely. And I think what I'd love to see is there being a path to use crypto for securities, for real world productive assets that generate revenue. I wrote an op-ed that was in the Washington Post a couple of weeks ago. And my argument was, there's a lot of criticism, skepticism around crypto, because all people are seeing are Bitcoin and meme coins right now. The reason for that is we're not actually allowed in the US to connect crypto to things of value. So of course, the easy things that regulators pass through are meme coins. And you know, nothing wrong with meme coins. I think those

• 1:27:47Speaker 04

  are very, very interesting. But what I'd love to see is crypto technology being applied to making it easier to invest in startups, eventually public stocks as well. The traditional financial system should move onto crypto technology as the next layer of infrastructure beyond cloud. I think that's going to be a huge thing. We see the value of both, because we have a large scale crypto business and a large scale traditional assets business. Crypto business is Over an order of magnitude less expensive to run because a lot of the central intermediaries like clearinghouses, settlement, transfer agencies, those are all done by software on

• 1:28:28Speaker 04

  the blockchain. And it's simpler to operate and you can pass on the savings in the form of better prices and also better user experience for customers. Crypto runs 24/7 by default. There's fractionalization by default. I don't even want to begin to tell you how hard it is and how much we've had to work to get to 24/5 trading on equities with Robinhood 24-hour market and you know, how complex it is to make fractional shares for something like Berkshire Hathaway A shares happen. Like, these are some of the most difficult engineering challenges that just like happen for free in using crypto technology.

• 1:29:10Jason Calacanis?

  So you mentioned startups there. I'm a big fan, as you know. I invest in 100 startups a year. I have the largest syndicate in the world, 11,000 accredited and qualified purchasers.

• 1:29:21Speaker 04

  So I'm glad to be on your show because hopefully I'm assuming this means we're still a startup, which I believe we are.

• 1:29:26Jason Calacanis?

  You have the startup mentality and never lose it because that's how you succeed. Only the paranoid survive and you got to keep focusing on product, team, and customer. Those three things you make it work. Tell me what your vision is for Robinhood users doing what I do every day or maybe participating in my syndicate. If I had a great company like Superhuman and I wanted to share it with the Robinhood user base, is that, are you and I going to be collaborating on something like that eventually?

• 1:29:56Speaker 04

  Yeah, I mean, I would love that. I mean, I'll tell you this. You look at what our customers are investing in right now and what they're interested in investing in. It's very clear. We actually publish it. Tesla, I mean, I think back since 2019 Tesla was the most commonly invested in name on the Robinhood platform. It was number one. Before then, it was Apple because you know, Apple was the most innovative company back when we started Robinhood. It was sort of in the wake of the Steve Jobs era. So it was Apple for a long time, then it became Tesla. Recently, it's Nvidia. So. Robin users love Elon Musk companies. SolarCity was very, very popular on the platform before before it folded into Tesla.

• 1:30:34Speaker 04

  Nvidia is very popular now. They're investing in electric vehicles, quantum computing, AI, which, you know, the proxy is uh is Nvidia there because there's really not that much in the public markets that can give you AI exposure. SpaceX would clearly be very, very popular if available, right? I mean, our customers love Elon Musk. They love Tesla. It's hard for me to imagine that, you know, SpaceX would not do well. And there's not too many opportunities to invest in AI in the public markets. OpenAI is is still private. Anthropic is still private. I think those would those would do very well also. And I think I think it's interesting. So the the retail angle is is obvious for me.

• 1:31:18Speaker 04

  Why is it interesting on the other side for the startups and companies? So I think for late-stage companies, it's useful because the employees want the liquidity. Some of them have been around for a long time. The employees are actually motivated to to sell some of their stock and take some chips off the table.

• 1:31:34Jason Calacanis?

  Do that, you know, as programmatically already. SpaceX, I think, does it twice a year. Stripe does it once a year. And they have a very orderly process to, you know, let people cash in some chips. And I think they even do it on a certain percentage. So if retail wanted them, and and there's like some Destiny ETF or something that not popular because it owned some SpaceX. And I don't even, I had the founder on here. I don't think they even was in, it might have been their largest holding because of the valuation. But it's not like they, at time, I don't think they had a very cheap price on SpaceX. They had bought it, you know, at a very high price. And people want it so bad that they found a way because consumers are smart, like you're saying.

• 1:32:13Speaker 04

  ETF ran up, right? The ETF ran up that showed you some of the demand.

• 1:32:17Jason Calacanis?

  Yeah, that showed demand, yeah. Not logic, but demand.

• 1:32:20Speaker 04

  So I I do think like later-stage, post-IPO, uh, founders and management teams of startups aren't super motivated to do it because in a sense, you start competing with the the startup itself for primary capital. So. I think the employees at that stage are kind of the stronger pull for, for the other side of the market. On earlier stage, the entrepreneurs would love to have that product. You know, I, I remember when I started Robinhood, we had a hard time raising capital. I mean, you were an early backer, but we didn't have that many believers in the early days. And you could get Robinhood stock, you could invest in Robinhood on Angel List.

• 1:33:00Jason Calacanis?

  Yeah.

• 1:33:01Speaker 04

  At a 10 million valuation cap.

• 1:33:03Jason Calacanis?

  Crazy.

• 1:33:03Speaker 04

  And we pitched so many individual investors who were just, you know, normal people who'd worked the job, built up a nest egg, retired, they're, live in the Midwest. And we pitched them just like we pitched every VC. And everyone who was interested, we gave them their allocation because we just, we, we had to take what we can get in those days. So, you know.

• 1:33:23Jason Calacanis?

  You're passing the cup around, just trying to make enough to get the company off the ground. Yeah. And we had, um, I think Thumbtack was five million, Uber was five million and Superhuman might've been 10. Yeah. So, yeah.

• 1:33:34Speaker 04

  Yeah. And, you know, I imagine if we had an easier way to, you just tap a button, you get access to global liquidity. And, you know, retail gets access with appropriate guardrails and disclosure to early stage opportunities. As a, as an early stage entrepreneur, getting my venture off the ground, looking for capital, that, that would be a great, a great product offering.

• 1:33:55Jason Calacanis?

  I am super excited about it. My best piece of advice to the SEC, I've made it clear to a bunch of my friends over there. Create an accreditation test.

• 1:34:04Speaker 04

  Yeah.

• 1:34:04Jason Calacanis?

  You know, and I use the example, when you go into Robinhood, if you don't understand options and puts and these, you know, more elaborate, uh, devices, not just buying and selling a share, but shorting it and getting it, doing options trading. You do such an amazing job, walking people through an education. Now, you don't have to do that, but you do it. What if in the United States, just like you have to have a license to be a barber, or a license to own a gun, or a license to be a teacher, or even drive a car, and these tests are different.

• 1:34:34Speaker 04

  Yeah.

• 1:34:34Jason Calacanis?

  We should just have, and the SEC has been mandated this, they've just kind of slow rolled it and they're slow walking it. Just a three or four hour course on private company investing and, you know, interesting nuances to that diversification and preferred shares versus common shares, all that stuff. And you just take a 50 question test. The test could be 25 bucks. You could do, you could have the test in Robinhood. You could have it at the SEC's website. You could do it any number of ways. And you have to take a course that would be free online, or you could take it in person for a hundred bucks. And this would be so perfect, wouldn't it?

• 1:35:07Speaker 04

  My take on that is, I, I think it would be odd if the friction to investing in a company like SpaceX, for example, is significantly higher than investing in a meme coin. It's like you, you have to pay, you have to, you have to take it a accreditation test.

• 1:35:21Jason Calacanis?

  Yes.

• 1:35:22Speaker 04

  Because SpaceX is, is risky and you have to know what you're doing, but you know.

• 1:35:26Jason Calacanis?

  I would like to have it for both. Like, and I'm talking like, man, when I took a firearm test in California, it was like, what's the best way to hold a loaded gun? And it was like, point it in the air, point it at the ground, point it straight in front of you, or have it in the holster or on the lockbox. And it was like, hmm, it was like the silliest test ever.

• 1:35:47Speaker 04

  Yeah. I think there's a lot of solutions and, and I think we're, we're excited to be kind of deeper in that discussion. I think that platforms can do a lot here to put private companies in different tiers. For example, you know, some companies have audited financials that are public company quality and you know, those should be in a high tier where they provide a lot of disclosure. And then some don't do anything. And maybe you put like a skull and crossbones and big warnings and say, this is like incredibly risky.

• 1:36:17Jason Calacanis?

  And then you'd have meme coins under it.

• 1:36:20Speaker 04

  Right. I mean, it's kind of like you have pink sheets and penny stocks right now that really don't have the same type of reporting requirements. So yeah, I'm more in the favor of like self-certification and really accurate labeling of

• 1:36:34Jason Calacanis?

  Yes.

• 1:36:34Speaker 04

  of what type of disclosure the, the company.

• 1:36:37Jason Calacanis?

  If you're a freedom-loving person, you want people to do whatever they want with their money, whether it's Vegas, sports, crypto stocks, you know, because you get educated. And this is what I always told people who criticized Robinhood. Oh, people are gambling, whatever. It's like, people are gambling. Like a third of the country does sports betting. I bet on every Knicks game using prize picks. I love it. It's my right to do that. I know that I might lose money, but I enjoy putting a Hyundai or five Hyundai on the game. It makes me more engaged. It's fun for me. My choice.

• 1:37:05Speaker 04

  It's American.

• 1:37:07Jason Calacanis?

  It's American.

• 1:37:08Speaker 04

  That's what America is all about.

• 1:37:09Jason Calacanis?

  Yes. And the only thing we need to do is disclosures. That's all. Some simple disclosures, some simple education. Vlad, wonderful to have you on. Thanks for taking the time, my friend. I look forward to coming to your all hands and I will be there for the hood conference next year. Great job. All right, everybody. Thanks for tuning in to the greatest startup podcast in the world this week in startups. What an amazing episode. I think we got to release this one as a one parter dressed for Raul and Vlad. Man, this could be something. Having those two overlap was spectacular for me, you know, and as we were mentioning with Rick Rubin's book, you know, make the art for yourself. This is an example of art for me. That was so engaging. I didn't want to hang up the phone here. We're two and a

• 1:37:53Jason Calacanis?

  half hours into this program. So what an amazing episode, a long one and a great one. And if you're listening to the audio feed, please, please go to YouTube and watch Raul's demos and you can get a vibe for everything. Go to our YouTube channel. I think Spotify has videos as well. So you can get it there, but please go to YouTube and sign up. And if you wanted to, you could have watched this live. If you're hearing my voice in the podcast feed, you could have watched this live. Again, go to youtube.com and search for this week in startups, subscribe and put the bell on so you get all notifications and you get about 20% more show for free. And then finally, you can go to thisweekinstartups.com/docket and you'll see the docket and you can participate in that by putting in questions or comments and help us build the docket. We'll see you all next time on this week in startups.