20VC: Biggest Lessons From Scaling Houseparty To Millions of Users, Why Today's Metrics Are Insufficient To Determine Product Success & What Breaks with Scale From Team To Product with Ben Rubin, Co-Founder @ /talk & Houseparty

Ben Rubin is the Founder & CEO @ /talk, the anti-meeting tool for fast, decentralised conversations. Prior to co-founding /talk, Ben was the Co-Founder & CEO @ Houseparty, where he scaled the product to millions of users and raised over $70M in funding from the likes of Sequoia, Greylock and Entree Capital to name a few. In addition over the last few years Ben has enjoyed roles at Sequoia as a Scout and then also at Benchmark as an Entrepreneur-In-Residence. In Today’s Episode You Will Learn: 1.) How Ben made his way into the world of startups and came to found Life on Air, later turning into Meerkat and Houseparty? 2.) What were Ben's key learnings from the Houseparty scaling experience? Why are the traditional metrics we use to measure startup success (DAU, MAU etc) insufficient? What is the nuance to metrics? How does Ben think about being first to market vs being the best to market? 3.) How does Ben believe the product principles differ when comparing the 0-1 stage vs 10-100 stage? How does Ben think about where to be rigorous on product? How does Ben advise founders to discover the key guiding product principle? What was it for Ben with Meerkat? 4.) Meerkat pivoted to Houseparty 3 months after having raised $40M, how did Ben communicate that to the board? How did they respond? How does Ben believe the best boards operate? What does Ben most look for in his board members? Where do many go wrong with board management? 5.) From the team side, when in hypergrowth, when do things start to break? What profiles are usually the first to break? Does that mean one should not hire those profiles? What can the leader do to create that intimacy and trust amongst the team? Items Mentioned In Today’s Show: Ben’s Fave Book: Seneca: The Shortness of Life As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

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

• 0:00Harry Stebbings?

  Welcome back. This is a 20 minute VC with me, Harry Stebbings, and I don't know about you, but I love discussions with truly world-class product people. And today I'm joined by one of the best, Ben Rubin, founder and CEO at SlashTalk, the anti-meeting tool for the fast decentralized conversations that have to happen in successful workplaces. Prior to co-founding SlashTalk, Ben was the co-founder and CEO at House Party, where he scaled the product to millions of users and raised over $70 million in funding from the likes of Greylock, Sequoia, and Entree Capital, to name a few. In addition, over the last few years, Ben has enjoyed roles at Sequoia as a scout, and then also at Benchmark as an entrepreneur in residence. I'd also want to say a huge thank you to Avi at Entrez for some fantastic question suggestions before this episode. I so appreciate that. But before we move into the show today, digital hit a new gear in 2020, and companies

• 0:45Harry Stebbings?

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• 1:28Harry Stebbings?

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• 2:10Harry Stebbings?

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• 2:51Harry Stebbings?

  Check out hellosign.com/20vc to join the thousands of companies and founders who value fast, secure and simple e-signatures. But that is quite enough from me. So now I'm very excited to hand over to Ben Rubin, founder and CEO at SlashTalk.

• 3:11Speaker 01

  You have now arrived at your destination.

• 3:14Harry Stebbings?

  Ben, it is such a joy to have you on the show today. As we said before, I've wanted to do this one for a long, long time, but I'm thrilled that we can make it happen. So thank you so much for joining me today, Ben.

• 3:23Speaker 02

  No, you got it. Thank you so much for having me. I really enjoy the episodes you guys put out.

• 3:28Harry Stebbings?

  That is very, very kind of you and flattery will get you a long way, Ben. So thank you for that. But tell me, how did you make your way into the world of tech? Come to Found House Party and what was Life on Air before, and then come to make the most recent step with the founding of SlashTalk?

• 3:42Speaker 02

  So I studied architecture and what I really find interesting in architecture is the opportunity to create spaces that create new encounters and new opportunity for encounters between people. And these are the things that I got the most joy in school. Towards the end of year three of architecture school, I realized that physical space is a physical space, but if you want to push the boundaries more in architecture, you can either try to develop new materials or you can basically be a great marketer. So you can get really quirky or what other people say iconic buildings.

• 4:20Speaker 02

  That are not necessarily create a new statement beyond look at this cool thing that we did. And that got me into thinking the digital world or presence in the digital world is a really new space, pun intended, to craft as an architect. And I thought maybe that's the kind of spaces I should build. Maybe this is the kind of spaces I should plan for. And I wanted to start building spaces that are presence based, meaning people are in these buildings, in these spaces, which is a definition of a building, but just online. So we started a company called Life on Air. The whole premise was mobile first, live video experiences to bring people together in the most human way possible when they're physically apart.

• 5:04Speaker 02

  And in a way, I've been an architect since school. I just do different buildings. House Party is a building with hundreds of thousands of people every day. If not, eh, sorry, millions of people every day. It's it's kind of crazy.

• 5:18Harry Stebbings?

  I love that, especially kind of the correlation, alignment between architecture and kind of building digital spaces. You mentioned House Party there and it was such an incredible journey and I still love the product, by the way. So I have to say a huge thank you for keeping me company in COVID times. But when I spoke to Michael at Everly, he asked specifically, when you look at the process now with the benefit of hindsight, and it's a tough one to ask, but it was Michael, so I thought it was important. What were your key learnings from the House Party experience?

• 5:44Speaker 02

  One of the things that I think is very important for people to take from this, as a product company, you measure your success on traditional, what is called like growth accounting. So there is like pretty standardized way to understand your MAU, DAU, what are the cohorts, how different personas, different types of people behave over time, mapping user stories, understanding what are the levers in the story that makes those users successful and et cetera, et cetera, right? And it's kind of a playbook that, I don't know, sixty to eighty percent of that playbook is being played in different variation in most of the company and most of the tech company. With House Party, we had this really interesting problem where the high schoolers,

• 6:28Speaker 02

  they had two key things that are going for them that made House Party successful for them. One is the idea of code of conduct. If you're a high schooler that uses House Party, you know about eighty percent of the graph, you know them, you see them in school. And basically, when you walk into the school cafeteria, you know exactly what table you can see that. And that kind of code of conduct, that mental model of what conversations I can be part of and who I can sit next to, actually transferred very well into the product itself. So in House Party, you would open the product, you would see who talked to who, and you know exactly by reading quickly the names, what table you can sit next to or what room you can join. And then the other thing that went very well for high schoolers

• 7:11Speaker 02

  is that all of them start school and finish school at the same time. They go to vacation at the same time, they have summers, holidays. So in a presence product like House Party, the availability of the graph is really key for the successful of the use case. If people are busy when you're available, you can't match with them, you can't talk to them. So we knew that we have a lot of high schoolers using the product, but we didn't know exactly how much and we didn't know exactly who was at what class. Like, are you senior or you sophomore? Like, all of these, I don't know exactly the terminology, but what year you are in your school. And it was really hard when House Party reached some plateau. We had a terrific engagement and a great community,

• 7:54Speaker 02

  but it's kind of stopped growing at some point. We had to actually look through all the classic growth accounting metrics and try to understand the problem. And the problem with that was that we couldn't find it because everything averages out, it kind of looked like how bees disappear. You would not understand how clusters of users all of a sudden stopped using the product. And there was so many different hypotheses for people. But it's only until we went and we actually started talking to users after users and flying around, I remember flying with the team every week to different places in the country, interviewing users, that we start understand. Oh, this might be something that is micro seasonal to every school.

• 8:38Speaker 02

  And once we going to identify to tag every user, not based on the traditional way of how many weeks they are in the platform. But actually, like a new way, which is when are they about to change to a new step in their life? When are they moving to a new class? When are they moving to college? When did the period that they are in right now in their life is ending and they are starting something new? Only when we did that and rebase, then we started seeing, oh, that's the problem. People are moving from a different state in life, different mindset to a new type of environment. Either it's college or a different school. And then they have new circles, new social circles that they want to talk to.

• 9:21Speaker 02

  And they have also different calendars. And that was the problem. And this is a long way of saying that the tools that you have are probably good to inform eighty percent of your decision. But there's gonna be situation in which only you can actually come up with the infrastructure and the tooling to understand your problem. You're not going to be able to solve that problem because you're choosing the tools that Facebook use. And when I say tools, I mean like thought process tools that Facebook use to create their growth. You are going to be able to take advantage of them and pick and choose what you want. But they're not going to give you a holistic view of what's happening in your product.

• 10:03Harry Stebbings?

  What do you mean by thought process tools? Is that the customer discovery process? Is that how you think about product principles? Like, what do you mean by the thought process from that standpoint?

• 10:12Speaker 02

  Thought process are basically mental model tools in which to count and account the metrics or the data that your user have. And there's different way, there is like, what is the aha moment? How do people get to the aha moment? What are the steps that they are doing? Show me all these cohorts on this versions that are moving on this funnel versus this users. Or looking at likelihood of things, there is a set of tools in the thought process of how I get a customer to activate more or activate better and be better engaged. And there is also a set of tools that how do I get the customers that are not yet convinced

• 10:54Speaker 02

  that this is the right product for them to actually convert into a customer that falls in love with the product. And both of these approaches, and by the way, you should kinda try to figure out what are the things you want to do for the people that are very much engaged? And what are the things that you should do to convert people to engage users? But these together, there's a set of tools, thought process tools of how we actually thinking about the problem. Because it's not enough to just throw metrics on a dashboard. And this is one of my biggest feedback to analysts or young analysts or even professional analysts that has experienced in a two dimensional way of looking at metrics. Metrics unfortunately are in all our dashboards are two dimensional and there's something poetic about it

• 11:39Speaker 02

  because it also reminds you that the depth in which between that depth and the data there is the story of what's actually happening with the user. I'll give you a separate example from my personal life. I don't know if we have a minute for it, but I think that will illustrate my point. Love to. I had this problem. I went with friends to Baja California. They're all surfers. I'm not, but for some reason I decided I'm gonna go with them. And I came back with this irritating eye, like I'm telling you, I couldn't, there were some weekends I couldn't leave the house. It was really horrible. It doesn't look red, but it's just this itch that I didn't know. It was hard for me to sleep. I went to three different doctors, all prescribed different medicines. Some of them flipped like the eye to look inside.

• 12:23Speaker 02

  And you would think, you know, these are serious people. There is like, I think, I don't know, maybe 50 years of experience between all of them. And it didn't go away, Harry, for four months. It didn't go away. And then my wife sees me is on, in all this pain and she asked me, what are you putting on your face? Because usually I don't put, I don't put anything on my face, but I said, oh, I went to Baja, I put this cream on my face and these are other things that I use from time to time. And I'm telling you, she reads the ingredients. Of that SPF face thing and she's like, well, the first ingredient, the first thing on the label is a famous notorious eye irritator.

• 13:03Speaker 02

  And I'm like, fuck me, you got this thought process of how people should address and how people should deal with people with eye irritation. And you got very professional people, doctors, they go and they look and they look at your eyes and they look for the different things and they open it and they take samples and they do all of the work that they're supposed to do in the process, which for the house party example would be do everything that you can to map your hypotheses and put them into the different kind of instruments of growth accounting to understand where exactly people fall off, what exactly is the culprit of the growth.

• 13:42Speaker 02

  And in the eye example, it was so easy, it was just take a step back from the process that you know, and think about what is the story that is happening. And all of these doctors knew I went to Baja, I put this, that. The one question you wanted to ask is like, did this person maybe put something on his face that irritates his eye? And can you believe the three doctors couldn't do that? And it's not that they can't do that, there's nothing wrong, I'm just saying the system trains us. And in fact, it's really good for society that on average, on eight or nine out of times, we're going to do what the validated patterns taught us. And it's very good that there is some sort of stability or else when people will walk around, you know, with those square holes in their skull every time they had a headache.

• 14:25Speaker 02

  But all it is to say that the traditional way of looking things is only one dimension. There's always your story and your perspective in how to diagnose a problem. And it's only you, the founder and the team that will be able to access that third dimension that completes the picture of the metric.

• 14:44Harry Stebbings?

  I mean, speaking of kind of your own dimension story there, I am really interested because I obviously spoke to Scott Balsky before the show also, and he asked me one really interesting one. And obviously, Meerkat and House Party competed with Periscope. And his question was, how do you think about whether it's best to be first to market or best? How do you think about that?

• 15:02Speaker 02

  Yeah, I think it's incredible to be first to market because Life on Air released live video products to the market since 2013. So we were able, two years before the Periscope team or Facebook Live team, to understand what are the metrics that actually make a live video work. What we realized very quickly with our second failed product, that you know, nobody knows about it, Jammy's Air, is that it's all about the retention of the broadcasters. You can imagine that founders will say, "I have a real-time video platform, I'm optimizing for viewers' retention, I'm optimizing for time spent," all of these things. But what I can tell you from my experience is that the only thing that matters, the

• 15:46Speaker 02

  only thing that is sustainable, is broadcaster retention. Because if you can keep the broadcasters engaged, that means that whatever amount of watchers they have, they have perceived value from them that is enough for them to be sustained on the platform. Whereas if you only have watchers, they are dependent on the broadcasters, and the soon as the broadcaster is not happy, you lose the watcher. So we knew it from the get-go that this is the most important thing. And this is because we were first to market with different product two years before them. So what's interesting, in the example Scott brings, he's talking about Meerkat versus Periscope. But what he's not taking into consideration is Life on Air as a company that produces

• 16:30Speaker 02

  these products versus everyone else who's running after live video. And that helped us a lot, because obviously, we came to the market and then Twitter launched their product, Periscope, and then Facebook Live came in. And one of the things that we saw, that we had the privilege to see with millions of people using Meerkat, is that the retention for broadcasters only existed in the celebs, media, and use type of users. The use case of what makes the platform heartbeat pounce, the use case for the broadcasters is only celebs, media, and use. And in that moment, we were like, "Okay, there is no use case for the 99% because, for them to be broadcasters, because they only..."

• 17:12Speaker 02

  Come to watch and when they go live, the likelihood is after the four, the fifth stream, you see that the likelihood of them going to the next stream is actually dropping significantly and continue to drop. So the novelty actually exists between the one to four, one to five first streams. And then you ask yourself, okay, then I'm competing on the 1% that is celebs, media and news. And if I'm competing against this, I know that Twitter is going to be better reached to onboard them. And I know that Facebook is going to get better reached to onboard them. So now I'm left with the 99% or not celeb media news. And by the way, at that time, everybody thought that everybody's going to be broadcasters. And we know today that live

• 17:54Speaker 02

  video is not what we thought it's going to be three, five years ago. It's actually a great feature on top of existing platform that is being used by celebs media and use more often than the next person. So when we realized that, because we had that insight, because we were in market two years before that, since 2012, within three months after raising $14 million from Greylock and other investors, we were like, guys, there's no broadcaster attention in the average person, in the 99% who are not celebs media news. And because of this, we cannot build an independent company that is sustainable. This is over time, give it two or three years, this is going to become a feature on top of platform. There's not going to be any independent

• 18:38Speaker 02

  platform for live broadcasters unless they have focus on broadcaster attention. And guess what, Harry? There is one platform like this. It's called Twitch. Twitch from the get-go focused on broadcaster attention. And this is why I think there's a lot of things about the kind of media and what is the kind of modality of the engagement there. But at the end of the day, they're focused on broadcaster attention and they're a very successful product. So anyway, we went to the board and we're like, we have to pivot. And we don't know what we're going to pivot yet, but we're going to focus on the 99% that are not celebs media news. And the next metaphor and the exercise in the company was like, what about a house party? If Mirkadi, if live video is a stage and that's not for everyone, what is for everyone? And everybody likes a house

• 19:22Speaker 02

  party. And that became the motif or metaphor that we actually derive all the product decisions from.

• 19:28Harry Stebbings?

  I love that. I spoke to Josh Elman before and he mentioned the journey in terms of you telling the board about kind of the decision to try something new. He also like, and you touched on it there, but I'd love to hear more. How did you convince them that it was the right move? Cause he still had something that had a lot of buzz, had a lot of attention. And so trying a house party is a little bit out there, Ben. Like, how did you convince them that this was the right strategic move?

• 19:50Speaker 02

  It's funny, at that point, we didn't know that we're gonna do a house party. We just know that we're gonna go after what was our liability. We wanted to flip to be our strength, which is, okay, you have this inside, there's this ninety-nine percent who are not celebs media news. And we say, we're gonna build for them. Cause for the one percent Periscope and Facebook Live, people are gonna reach out to them. They're gonna try to have them and they're gonna have better chances on these platforms because those platforms have much better reach. The way I went about it with the board is showing them the amount of watchers that we have. And this was going up. It's like a beautiful graph that any CEO would love to vault into a board's room and show this graph of users going up.

• 20:32Speaker 02

  The watcher is going up. But then I flipped it and I showed, but here are the broadcasters, which was not going up. Not going up is like a curving up, but it was like, you know, not growing, not shrinking. And then I showed the broadcaster attention. And that's where they kind of see watcher go up, broadcaster steady. Broadcaster attention goes down. And then I also broke down type of broadcasters that we have, based on the amount of following followers that we can get from the Twitter API. So I was able to identify which of the retained broadcasters are considered influencers. I mean, have certain ratio between following and follower, and which of the broadcasters are actually the average Joe.

• 21:17Speaker 02

  And I was able to show those differences and I was able to detailly click the data and show them, we have cancer in our body. And I know the body feels great and I know that you feel healthy, but here's the cancer. And the reason I know it is because I've been in the market for two years. And I think obviously you don't wanna surprise your board. In stuff like this during the board meeting. I think board meetings are not for, rarely or really when she'd hit the fan art to make decision. Most of the time, board should be used as discussion platform. And so all of them had like one on one with me. I had one on one with Josh. Where I went to next to his house, we had dinner and I walked him through and explained to him and had an opportunity for him to react and digest it.

• 22:02Speaker 02

  To Eden as well. And when I walked into the board meeting, they already were briefed, they knew, they had their thought, they had the ability to digest. And that's kind of diffuse all the emotions that are associated with a founder coming and telling you that he wants to pivot the company. Three months after he raised forty millions dollars out of you. And to Josh's credit, he was terrified, but supported. And I really appreciate this about Josh. This is one of the things that I really appreciate about it.

• 22:28Harry Stebbings?

  I love that. And that does sound like Josh. So that's very funny to hear. I'm interested. You said about kind of the forty million there and you know, obviously funding allows you to scale team pretty significantly. And I'm a big people person. I think companies nothing without a team. And you've had multiple different companies now across different products. When you think about building a team from zero to one, what have been your biggest lessons? And I'm sure founders ask you for advice a lot in terms of this pre-seed stage and seed stage. What advice do you give them, kind of having seen all you have done?

• 22:55Speaker 02

  I've grown a lot and I got so much to grow more, but I used to be very aim like. And there is this framework that I like to think through, which is aim versus origin. If I may, I can give you another example from my life, if you have a minute.

• 23:10Harry Stebbings?

  Love to.

• 23:13Speaker 02

  So when I finished the idea, I got like a little bonus course. And that was about going into an ah, a military course for being a lifeguard. But I was in this unit and I was like about to just finish my service after three years. And they're like, oh, you've been great. How about you take this course that is fun course to learn how to be a lifeguard? And what they didn't know is that the army changed the guidelines for who can come there. And it's no longer can be like a little treat or a bonus that you can give someone. It's only for people that are actually going to be lifeguards. In the military. And the only people that are going to be lifeguards in the military are Olympic Israeli swimmer

• 23:55Speaker 02

  or people that swim with the Israeli national team that are eligible to actually participate in this course. But my unit didn't know that for some reason. It makes sense, actually. And there was me coming to this course. There's nineteen Olympic swimmers that instead of doing the IDF service, what they're doing is basically being a lifeguard in the IDF and me. And let me tell you, I'm not an Olympic swimmer. And then they have this pool, you know, Olympic pool. And they say, well, we're going to do benchmarks now because you start with a benchmark. And then we work towards the end of the course. We're gonna see if you can meet the criteria. And I go there, Harry, and I just swim with my entire body.

• 24:37Speaker 02

  And my hands are slapping into the water and water is going over where and I give a hundred and seventy percent of myself, like really, it's just incredible. Like water going all over place. I'm putting all of my energy into this. Then the Olympic swimmers go and you can barely hear them. You can barely hear them. They move with the water and it's almost looks super slow. And if you put my track, my video next to them, if you look at it separately, you think, oh, Ben was probably faster. Look, he's putting all this energy. He's moving his hand so quickly. Water is going everywhere. He's putting his all. When you look at my video, you'll be like, he's probably finished it first. But if you put me next to the Olympic swimmer,

• 25:19Speaker 02

  you will see I spent an order of magnitude more energy, but I'm moving slower. And the Olympic swimmers, they are focused on the technique to the such perfection that not only you don't hear anything, they're in flow with the water and they're moving two, three times faster than me. And you know, I always thought about it as funny bar joke. But when I look back at process and product development and actually any kind of relationship I have in life and where do I put my energy in? I think to myself, like, am I focused on getting there faster? Or am I focused on the right process, on the right movement? That when I Invest my energy, it goes with the flow.

• 26:01Speaker 02

  And I know it was a little bit of a roundabout example, but this is my way to tell you almost my emotional philosophy towards the early stage, the zero to one stage. Because honestly, there is no aim. Aim is a defined idea of what is the outcome exactly going to be, does not exist in that early stage. It's not like you can say, I'm going to be B and I'm going to get to be B immediately. And that's going to be B. You're going to say, I'm going to go from A to B and you're probably going to be at C. Or you're probably going to learn something on the way and you're going to be at D. It doesn't matter. But if you're going to force yourself to go to a defined outcome, you're going to be not only miserable, you're going to be slower because you're going to fight all the other flow and all the energy.

• 26:46Speaker 02

  You're going to put all the energy to kind of force the reality to whatever image you have that you need to get to in your head. And I think that's very limited. I think that's very limited. I think it's hard. And I think one of the things that is really emancipating to me is to release the idea of like a defined end result. And focus on the process. Focus on having the right hypothesis. Focus on having the right process on how to come about them. Focus on having the right team. Focus on giving instructions that are more like attitude and rhythm and vibe and help through example. And let the kind of the flow take you there. Because you're going to get to there faster and you're going to get to there happier.

• 27:31Speaker 02

  And you're going to be open and see different variations of success that you didn't think about from the beginning. And this is how my thoughts have changed over the past 10 years is the idea of letting go, whatever it is that you think it's going to look like two years from now exactly.

• 27:46Harry Stebbings?

  I I totally get that and I love that as a perspective. I guess my question to you is like, if we take the swimming example, which I love by the way, Ben, but if we take that as an example, and it's like, some people are just naturally good at swimming. They go with the flow naturally and sure, they've had practice and process and whatever, but it's not your strength. I guess my question is, how do you determine whether to spend time and get good at something versus appreciate that, you know what, I'm not going to be as fast as them at swimming or I'm not going to be as good as her on process or him on legal dogs or whatever. And I'm going to spend my energy elsewhere. How do you determine between the two?

• 28:20Speaker 02

  But that's what's great about the ability of having a team. If you are thoughtful, if you're self-aware, if you're reflective, you're probably gonna be able to understand with some sort of good directionality, what are the things that you're good at and what are the things that you need help? And what are the things that you're actually bad? And if you are honest with yourself and true with yourself, you write them down without being emotional and say, "Oh, I suck at this." And you actually double down on the things that you're great at and you hire for the people that you're not good at. And sometimes you even have conversations, depends on the kind of hire it is, like about what is the right fit for you and what is the right fit for them? And you use that as a way of building their relationship and building the trust together.

• 29:03Speaker 02

  So I think that the only thing that's worth perfecting is that process, is that process of self-reflection and thoughtfulness in yourself, in your product, in your product process, in your team, in coaching your team to have that, in your company, in your relationship with investors. How do you keep iterating those relationships? And how do you keep iterating the process that ultimately creates a product? And the idea that product is not something that is defined. I hate, hate the word V1 or V2 or V3 because the product will never be perfect. And it's always going to be an iterative thing. There's always something new to learn. There's always something to iterate.

• 29:47Speaker 02

  And I think from early on, it's important to tell people, this is not about getting to V1. This is not about getting to V2. This is about enjoying every single moment of the movement and making sure that we're doing the movement perfect, the process perfect. And we can trust that we will get over time to the directions that we need to go to. But it's not defined right now. What is defined is what is the right movement that we need to invest energy right now in this water? And I think that really for zero to one, that really frees up the collective thinking and diffuses a lot of the insecurity that the team has. Because as humans in this society, in Western society, we are trained...

• 30:30Speaker 02

  That things need to lead you to a next step and every step need to be perceived as is a moving forward for the next step and everything need to always go up for the audience I'm staying up with quotations but the truth is is if you're open you stop thinking about going up and you're thinking about what is the kind of work I'm doing that makes me feel fulfilled every day but it's also the correct way for my hypothesis around the water around me and the direction I need to go without being a slave for some defined outcome in the future.

• 31:04Harry Stebbings?

  Can I ask, I love the self-awareness around process, around vulnerabilities. I love it as a mindset. My question to you is like you have that in zero to one and we have that initial team that's incredible and we're very proud of them and then we raised forty million say uh as a as a nice number and now you've got to build a big team and you've got to build it fast. Where does things start to break in your experience and what goes wrong?

• 31:27Speaker 02

  Well, one thing is the intention of the people that you hire when you're on a rocket ship and you grow really, really fast and I've seen it twice. The intention of the people is different. These are people that usually come from some big company where they have a career and they decided that they're going to take a chance on you and come and join your team. It's really a different DNA. No matter how you try, it's really a different DNA and where I see it breaks is where things don't continue to grow and then the people who took a bet on you are looking around and say, well, Mr. Rubin, what's your plan? That was a hard thing in house party

• 32:09Speaker 02

  and this is a hard thing to answer, especially as you're working through product and growth problems that are not easy. Like it's really easy when things go up. It's really easy when things go down because it's really easy to understand what's happening. But when things are kind of like not growing, not shrinking, even some a little bit growing over time, it's really hard to understand because what you're dealing is not pure black or pure white and it doesn't matter what's good or bad. Gray, it's really hard to like, how do you decouple gray into different colors? How do you take this mash of things? And I think ultimately it's hard because half of the company,

• 32:52Speaker 02

  or at least the people that were from the start will say, I know we got from zero to one, but if we cannot grow one to one hundred, fuck it. Let's break shit up and be okay with losing some of the one that we gained in order to get to the one hundred. And then half of the company will say, wait, wait, wait, wait, wait. We have this one. We have to protect this one. We can't do things that will hinder that one. And I think bridging between those two cultures of the people you hire, as you're iterating and pivoting a lot and to the people you hired after you started the immense growth, it's hard culture to bridge. And I don't think I've done a good job there, but I think also I learned a lot from that. And I learned as I go into my next thing now, I take the intention of the people,

• 33:36Speaker 02

  I take very much into consideration and into how I communicate.

• 33:40Harry Stebbings?

  Last question, I'm too intrigued on that note. When you think about that then, and the intention of the people, and it's totally understandable for the people coming in from big companies to have that mindset and that intention. But then from your experience, do you just not hire them? They're not a fit for maybe your style of leadership and for the company that you want to build? And it's like, hey, I want these true blood believers who will break shit up when something goes wrong and be a lieutenant beside me in all cases. Or do you go, actually, these guys from Facebook or Google, or you name your big incumbent, are incredible at what they do and we just need to make sure that we stay within their kind of realms of comfort to make them happy?

• 34:16Speaker 02

  That's a great question. No, I totally don't think that the right answer is not to hire. I think that for every stage you have different hires and I think there's incredible people in big companies that know how to scale shit up. And given a product that they can market or they can grow, they will grow it. Ultimately, it's the job of the CEO, it's the job of me, for this example. It was my job to create the expectation setting and create the kind of conversations that actually lead for productive.

• 34:50Speaker 02

  Outcomes for the company and productive outcomes are not necessarily productive by money, not necessarily. Productive means a lot of things and I think that if you don't pay attention to the kind of different cultures that as your company growing size, if you don't pay attention to the different intentions and you don't create a structure of conversation and expectation setting early on. Then when your company stop growing, you're gonna have different people looking at this problem from different angles. And it's gonna bring a lot of contention because you didn't create the environment to address that early enough.

• 35:27Harry Stebbings?

  I do wanna move into a quick fire round, Ben. So I say a short statement and you give me your immediate thoughts. Are you ready to rock and roll?

• 35:33Speaker 02

  Yeah.

• 35:34Harry Stebbings?

  Okay, so let's start with the hailed favorite of mine, which I never fucking read any of the books anyone recommends, so it's an interesting favorite, but anyway. What is your favorite book, Ben, and why?

• 35:44Speaker 02

  Seneca on Shortness of Life, Life is Long as Long as You Know How to Use It.

• 35:49Harry Stebbings?

  Love it. I've constantly been referred to Seneca, and so I need to.

• 35:52Speaker 02

  Short, it's a short book that explains how life can be longer if you're more present. But the way it goes about it from, I think it was like right before counting like fifty, eighty or something like that. And the same problems that you think you have with society, he describes, and this is kind of beautiful.

• 36:12Harry Stebbings?

  Tell me, I hear from Michael at Avalan, you've been meditating for two years. What are the main benefits?

• 36:16Speaker 02

  I do TM, I go in and out in waves of clarity, like sometimes it's really hard for me to get into that transcendental state. I think essentially what I think it does for me, it trains me to be aware of my thoughts and my feeling almost as a bystander to them before I react. So I become a better observer and a better reactor, because I don't react.

• 36:43Speaker 02

  That fast. So that's kind of the benefit of this.

• 36:46Harry Stebbings?

  I love it. That's hilarious. Tell me, what are the pros and cons of being an entrepreneur in residence?

• 36:51Speaker 02

  Look, I had a really interesting experience with Benchmark, which was, you can call it an E I R, and I think that's the kind of a vehicle we used, but it wasn't really an E I R. Basically, Peter Fanton was, hire who you need to hire, start hacking around, the year's benchmark credit card, and I trust you. And like, obviously, this sounds a little bit unfair because it sounds super casual, but we had a plan of, this is the space we're going to go after, this is the problems that we believe we see, and we're going to use this time to explore and understand what is the kind of action we can do in the market, and what are the motivations around that? And we actually had it pretty detailed out. But what was nice about it, it was almost like incubating for free.

• 37:32Speaker 02

  And it was great because you get to enjoy, smart people in Benchmark to give you feedback, and you also enjoy the fact that they have a great network and they can put you in touch with, back then, this was before Covid, they put me with all the most successful remote companies, and I was able to interview a bunch of the engineers and I seized there and informed my hypothesis before starting this company.

• 37:54Harry Stebbings?

  Well, I mean, speaking of that, what do you believe is the biggest misconception about the future of work?

• 37:59Speaker 02

  There is a couple of things. I think people think that it's all going to be remote from now on. I actually, I'm a, I'm a big Hegelist, the philosopher, and one of the frameworks that I use is, evolution is always happened where in the union of opposing forces. So you've got the thesis, and then you've got the antithesis, and then the synthesis of them is actually where evolution always happened. And it happened, and you could look at it in, in music, you can actually look at it about the differences between Gen Z to millennials, how every time as humans we are reacting to something. It's poetic, it's almost like physics, right? We're always reacting to something, but actually the truth will be in what is the synthesis of things.

• 38:43Speaker 02

  And a lot of the time when I say this, people think, oh, synthesis is the average of both. But no, it's what are the right things that you pick from one side and the right things that you pick from the other side? And the evolution will come from the middle. So I think this is a misconception. I think another misconception is that from the world that we're at in our company is the idea that there's going to be pure presence, large scale product that are only based on presence. I think that's also a reaction to the culture of meeting, but I'm not sure that this is the evolution. I think that there is a synthesis that will be the evolution. So I don't know. I think these are two big ones.

• 39:20Harry Stebbings?

  Two very big misconceptions. Ben, I do want to finish on probably the most important of all. Tell me, paint the picture. What do the next five years hold for you and for SlashDoc?

• 39:29Speaker 02

  Well, for me, it's going to be building this and learning to better myself in all the other works that I do with myself. For SlashDoc, look, in SlashDoc, we're trying to understand what is the unit value of a conversation or a meeting in an organization. And then we actually map it as a funnel and we walk back from what is the value to what are the building blocks, the atomic building blocks that make that value. And then we try to separate them and reorganize them in a whole different way for conducting conversations. So we're focused on quick and scheduled calls. Anything that is a conversation, internal conversation that is not on the calendar. And the nice thing about it and the nice thing about what I talked to you about the swimming metaphor is that I don't know

• 40:13Speaker 02

  how the end result is going to be. The end result is always going to change and be better and we're constantly going to improve, but I don't know how it looks like. But what I can tell you is that right now, as we're swimming, we have strong conviction about what kind of movement and what kind of way to put the energy in the water and the flow to do. And we're rethinking how we get from A to B. And we also are okay that as we're iterating on our movement, we might find ourselves in a different air, in a different place. So I guess this is a long way of saying, I'm looking to continue to invest in the mo, in the movement every day and improve how I swim in this new kind of water that we're charting.

• 40:55Speaker 02

  And I have no idea where we're going to be in five years, but I know that wherever we're going to be, that's the right place for us to be.

• 41:01Harry Stebbings?

  It's not, my friend. I can't wait to see it. What a terrible question after the suggestion of plans being so inefficient, but I've so enjoyed this, Ben. And thank you so much for joining me.

• 41:11Speaker 02

  Thank you, man. I hope people like it.

• 41:16Harry Stebbings?

  I have to say, I do just love Ben. Some very exciting times ahead with Slash Talk and an incredible thinker and product mind. If you'd like to see more behind the scenes from us, you can on Instagram at H Stabbings 1996 with two Bs. I always love to see you there. But before we leave you today, digital hit a new gear in 2020 and companies need the tools that will allow them to flourish in our ever-changing world. That's where Amplitude comes in. Amplitude helps the top product and growth teams at companies like PayPal, Instacart, Peloton and Atlassian build product experiences that convert and retain customers. With their product intelligence platform, you and your team will better understand user behaviour, ship great product experiences faster and retain more customers. And they've become the gold standard in analytics for teams asking what is happening in their

• 41:58Harry Stebbings?

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• 42:42Harry Stebbings?

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• 43:24Harry Stebbings?

  ...e-signature solution used by millions to securely send and request legally valid digital signatures and agreements and they raised a total of $16 million in funding and recently got acquired by Dropbox for an impressive $230 million. Check out hellosign.com/20vc to join the thousands of companies and founders who value fast, secure and simple e-signatures. As always, I so appreciate all your support and I cannot wait to bring you an exceptional set of episodes next week.