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No founder should be all-consumed with work, and that is why Head of Bloomberg Beta Roy Bahat is no longer a founder. This week Roy joins Gina Trapani and Michael Shane to discuss how workplace boundaries are becoming normalized and why providing VC support in a company’s irrational phase excites him more than a later, safer bet. He also stresses the importance of language in a large and diverse workforce and questions whether metaphors and analogies are useful or alienating.

 

Transcript

Gina Trapani It’s funny, right before you hopped on Roy, Michael said to me, Roy is like Yoda. And it’s true because I remember the conversations that we actually had. You were basically saying like, search your heart. What do you want, what do you want to do here? And then we’re going to find the path forward. Like I remember having a really deep conversation like that very early in our relationship. And I don’t get that close to people that quickly.

Roy Bahat You were productivity hacking me. You had a little bit of a star thing from Lifehacker too. Sorry, I didn’t mean interrupt. [Gina laughs.] Actually I probably on some level did mean to interrupt you because I deflect compliments. [Gina laughs.] And so that was me just deflecting that compliment. And thank you very much for saying that. 

[Intro music fades in, ramps up, plays 10 seconds.]

[0:51]

GT Hi, I’m Gina Trapani and this is the Postlight podcast and I’m psyched. I’m going to let the 1980s child out and say the word psyched—I’m psyched about this.

Michael Shane Are you super pumped? I hear that’s going to be a show.

GT Super pumped. Stoked. Very excited. Very excited about this episode today because we’ve got a really, really special guest. First I want to introduce my co-host, head of digital strategy at Postlight, Michael Shane. Hey Michael.

MS Hey Gina. It’s great to be here. I agree. This is going to be a bodacious episode for sure.

GT [Laughs.] Before we get started, how’s your day going today, Michael?

MS It hasn’t been boring, so—

GT It hasn’t. It hasn’t.

MS What do I have to complain about really? My day’s going great.

[1:31]

GT [Laughs.] I think it’s fair to share with our listeners that Michael and I, we are at a growing professional services firm here in New York City. We’ve got amazing clients. We’ve got an amazing team and we have been in the stuff today. And so solidarity with everyone in the world who’s listening who’s been in the stuff. We’ve been in the stuff, the good stuff.

MS Meaning a crisis exploded for you. And this is your moment to pause and smile.

GT Not even a crisis—just the sort of normal course of business people stuff that comes up. You’d think that we were all kind of with our headphones on quietly making software, but that’s not how software works. It involves people. It’s messy. It’s real messy.

MS These computer things tend to make people very emotional.

GT Exactly.

RB Yes, people get upset when I talk about champagne problems, but we’re lucky to have these problems, so.

GT [Laughs.] We really are. It’s true. Well, I’m really super excited to introduce our special guest today: Roy Bahat from Bloomberg Beta. Hey Roy.

MS Hey Roy. 

RB Hi.

GT So glad to have you here on the show. It’s funny, Michael and I both have separate but different relationships with you at different times in our career and we were both like, oh, we get to talk to Roy today! This is going to be awesome.

RB Love discovering that. Well, Gina, you made me definitely have a moment of passage of time awareness. It’s like the last time we walked, your baby was in a stroller and we were in Southern California in the sun. And it’s like, oh my gosh, it’s another lifetime.

GT Yes. It’s true. It was another lifetime ago. And I should say—full disclosure—so Roy was one of the investors in my former company with my business partner Anil Dash. I’ve gotten to work with you in that capacity. Bloomberg Beta is incredible, an incredible firm and group.

MS It’s a special firm, yeah. 

RB Thank you.

GT It really is special, really unique. And I was so lucky to have that opportunity to work with you. But I wanted to put that out there as we talk about what you’re doing and what you’re saying.

[3:10]

RB First, thank you for the disclosure. And you know, the way I saw it is you were my customer because that’s how we think of these things. So hashtag proud investor kind of thing. [Gina laughs.] But also, I didn’t know how to pronounce your last name until you just introduced yourself. 

MS That’s life on the internet!

GT [Laughs.] Everybody says my name Tri-pi-ni—it’s all good. Well, I have to say, you said that you felt like I was your customer. I mean, this is, I think really distinguishes Bloomberg Beta. And I want you to talk about it, but, you know, you were just so generous with your support and friendship and just open and were as an advisor and always had like those resources, that pep talk. And I think that that whole spirit really infuses everything you do with all of the companies you have relationships with.

[3:50]

RB Thank you. 

MS I’ve always felt that way about Roy and I’ve never been Roy’s customer. At best, I was lucky enough to be a sometimes collaborator. [Gina laughs.

RB One day, Michael. You don’t realize this is all part of the long con. 

MS Ah, I see. 

RB I’m doing customer development right now as we speak. [Gina laughs.

MS Amazing. 

RB Like, I’ll just say, I really appreciate that you saw that Gina. And we take very seriously that responsibility, because my way of thinking about it is I’ve done a lot of different kinds of things in life, not always successfully, but I’ve worked in government and nonprofits and big companies. I started a company investing, academia, blah, blah, blah. And I just realized that the trade I love more than any other is the trade of making new things. And I don’t practice that trade directly myself because doing it in a startup, I found so emotionally grueling that I kind of think of myself as like, I’m like one of those people who like, works in the music industry who tried to make it as a musician, but couldn’t quite cut it, but therefore really looks up to musicians. [Gina laughs.] And the way I think about it is my job is to help extraordinary founders do something extraordinary. And it always expresses through service, like trying to be useful to people, blah, blah, blah, as VCs say, but it doesn’t always express this friendship. And the goal is not friendship. 

GT Right. 

RB Friendship can be an amazing byproduct of it, but my wife has this thing. She says, she’s like, well, is that person really your friend? Or is it like, I don’t know, some other word for a business contact. And I kind of feel like people who are in a people occupation, which VC is, or sales people, whatever, need a hundred different words for friend. Yeah, it’s like, well, is that a, you know, whatever— 

MS Yeah. 

GT So true. 

[5:35]

RB And that means sometimes tough talk and real talk and all that stuff, because I don’t want—as a founder myself, I resented two kinds of VC support. One was the critic. I was like, I don’t need a fucking critic. Pardon my French. I don’t need somebody to tell me we missed our numbers. Yeah, I know we missed our numbers. Believe me more of my life is on the line here than yours. So thank you for your very helpful observation, you know? [Gina laughs.] And then the other kind though is the cheerleader. Who’s like, yeah, man, this is so great, dude. Everything’s so great. I was like, that doesn’t help me either. It’s all nonsense. And so I’m just trying to do the thing that I wished when I was in the seat, somebody on the other end was doing. And we were blessed in the startup that I co-founded by having some magnificently helpful investors and by having some complete dopes. I got a lot of data. At the risk of sounding like it’s all rational, because it isn’t, like a lot of this, like making anything is affairs of the heart as much as anything else.

But I detect often when people are trying to make things, whether it’s making a piece of software or building a company or whatever that we have learned that if we have logic, we’ll be fine. And so we try to back into these decisions. So many of them through logic. Should we sell to this kind of customer or that kind of customer? 

GT Yes. 

RB And the reality in making something new is it depends on irrational levels of devotion from the person making it. And so if they convince themselves something is logical, but like their body is telling them that that’s not what they should do, or then they have the worst kind of thing, which is the thing works. But then all of a sudden they’re a person who just wants to make software running a company that is driven by enterprise sales. And they realize their job is to manage a workforce whose job it is to take other people out for steak dinners, then it doesn’t work. And so like the critical data point is where is your kind of like, where is your irrational wind from within? [Gina laughs.] Because that’s the source of energy that we’re like holding up a sail and trying to harness. And it doesn’t mean you could do whatever you want, but like it kind of has to all work together in a system.

[7:36]

GT It’s so, so true. The spreadsheet isn’t going to tell you what to do, right? It’s where your heart is and where the love is. How do you work with founders and recognize in leaders that passion and love and that belief and that ability to just to make it happen, even if it feels like the irrational path?

RB Real talk. I don’t think I’m that good at that. And I don’t think it’s possible to be that good at that. So you’ll talk to a lot of investors about what they do and say, well, what’s the number of—oh it’s the people. Well, obviously after the fact, it’s the people because they did something extraordinary. So they’re extraordinary. So I have a simpler way of thinking about it, which is, do I want to work for this person? Do I believe that the next time they call me I’ll want to have the conversation. And that has served me really well. One, because I think it models what the relationship actually should be. And I learned it from my partner, James Cham, who I remember we came out of a meeting in our first year as investors. And he’s like, you seem like, you really like that guy, right?And I was like, yeah, I thought he was great. And he’s like, so he’s the kind of person you would hire as a CEO? I was like, exactly. He’s like, wrong! [Everyone laughs.] If the person’s successful, you want to work for them. And it’s like, ohhhh [makes mind exploding sound.]

GT Interesting. 

RB That just kind of expanded my mind and what it means is the people have some things in common, like values. Like I can trust them. I like how their mind works. And then it also is a natural way to include difference because I don’t want to work for all people who are all the same. 

GT Yes. 

RB I want my day to be full of people of different backgrounds and different ways of thinking about things. And so that ends up being roughly it. But it does also mean that the vibe I get deep in my heart is like not in and of itself enough of a reason to invest. The same way that you’ve got to be informed by the spreadsheet in what you’re building. You can’t just go with like, well, my heart tells me that what I need to do is build an anti-gravity beam because it’s just not possible. And so these things have to meet. And in that meeting of the kind of irrational and the rational, I think is a lot of where the magic happens. 

GT Yes. 

MS Are you looking for founders or leaders that come to the table already armed and ready to understand the spreadsheet, balance it with what’s in their heart? Do you look for opportunities to mentor people through that process, seeing perhaps potential in themselves as a leader that maybe they don’t even see yet? 

RB It depends. It’s a bit of a timing and dosage thing in the sense that it’s always gratifying to support somebody in the journey, but the very best founders don’t need that much of your help. And so it’s a just right kind of a thing. Like sure is it satisfying when I believe I’m the missing ingredient? You know, like we invested in Replit and the founders tweeted that without me and Bloomberg Beta support, they wouldn’t be where they are today. Because we took a bet before anybody else would take a bet. And, you know, whatever other support we provided. And that’s been an extremely gratifying relationship. And at the same time, there are definitely people who I think like peace out the money was nice. You know, you’re not gonna bug us. And those are less satisfying for me. I don’t want those relationships, but they can be just as successful. And then one other thing that I’d say that I end up paying a lot of attention to is word choice and language. So I’m going to pick on something Michael unfairly that you said, just because it’s a thing that’s not about you. It’s about something all of us do, which is one way in which I think the working world, you know, we were the first venture fund to focus on the future of work. And so we spent a lot of time thinking about how to improve the working world, not just for people like us who have office jobs, where we get to talk to each other through fancy microphones and call it work. But for everybody, to the extent we can figure it out. And one pattern that I’ve noticed from the modern business world is the modern business world loves to use the language of war. 

MS Yes. 

GT Yes. 

RB And especially now. And so you said, and by the way, I do it all the time. 

MS Armed. Yeah. 

RB Shoot you an email, you know, I say, and you described being armed. And I think that that language has been extremely helpful in certain ways it’s motivated people. It has given stakes to the battle quote unquote. But I also think it’s been really harmful and I don’t mean that—I hope you understand. I don’t mean that as any form of personal anything because I noticed it in my own language—but that’s a way in which we’re trying to support the ecosystem of work is just by saying like, Hey, I noticed this thing. 

I’ll give you an example of one that I’ve picked up within the last two years is we talk a lot about different occupations. And I was in a meeting, I was a commissioner in a public setting for this California Governor’s Commission on the future of work and I, or somebody else, it doesn’t matter who, said something about low-skilled work versus high-skilled work. And there was a woman there who runs an organization now called One Fair Wage, Saru Jayaraman, and she said, I just want stop you there for a second because she organizes restaurant workers and she’s like, go try to be a restaurant worker for a day and then tell me it’s low-skill work. And so now I’d refer to it as low-wage work or high-wage work at any event. And it’s one of the reasons I love doing podcasts and I love audio as a medium is it just allows us to really explore this. What does this all mean to us? And you know, anyway, end of rant. 

MS Yeah. Words matter.

[13:00]

GT Absolutely.

RB And actually I’m curious for both of you about this, because you run a workforce that includes people of many different backgrounds. You have clients who have many different backgrounds. One way I’ve struggled with this is weighing what words mean in one setting versus another. So I’ll give you an example of one is we talk about pipelines a lot in investing, you know, we talk about pipelines of talent and all kinds of pipelines. And I was presenting to this group of emerging investors and one of them said, I work with the Native American community investing in Native American founders and—that may have not have been her description of the community. But she said, the word pipeline we can’t use, because it really bothers us because in our—and I was just like [mind exploding sound]. 

GT Yeah. 

RB And I find myself especially, like real talk as a white man in tech, thinking about what are the words that I do and don’t use, how does that create space for others? And I mean, you know, as challenging as it is, it’s way less challenging than what many, many other people have gone through for hundreds, if not thousands of years, but it’s another reason this language issue. And I’m curious, you know, like we had a whole discussion in our team meeting of when should we, or shouldn’t we include pronouns in our Zoom now that Zoom has the turn on and off pronouns feature.

 GT Yes. 

MS Mhm. 

RB And I’m just curious since you run a larger organization than I run, how you handle these questions of like language around difference and who shows up in what way with what words?

[14:36]

GT I mean, it’s such a great question. And it’s something that we’re constantly thinking about and learning about. I mean, part of our job, we’re a professional services firm. We work with clients and the way that we’re successful is building trust and credibility with those clients, right? And part of building trust and credibility is showing up in the room and being able to speak the language and make the client feel like we are on your team. We are with you. We are not your vendor. We’re not someone you’re paying. We’re on your team. And ideally if it’s not the pandemic we’re sitting in the room with them. And that means understanding the lingo, putting on the jersey, and fully internalizing the client’s problems. And so, we’ve had this debate, Michael and I have talked about this: when the pronouns? And to me, my view is always like, you want to think about the best context, you know, like where is this going to be meaningful? Where is this going to be confusing? When culturally is this going to be confusing, alienating versus like, like a signal that we’re all kind of here on the same page together. And that’s a very nuanced, I mean, those are debatable questions—we have templates that we use for decks and, and it’s like, do we do this by default, do we show it on the website? Where? Does it rank as high as your titles?

[15:47]

RB I’m just curious to probe on the details. Because I often think the details are where these things happen. 

MS Yeah. 

RB You know, this may be an innovation from after Gina you were a company in which we invested. We now do these monthly talks where founders talk to other founders about the tips and tricks of the trade. And we call them “turpentine talks” after this Picasso quote. That is, you know, I think I saw it first from maybe Chris Dixon or somebody like that. The quote is some something like, it’s the art critics who, when they get together, talk about the big ideas: form structure, meaning. When real artists get together, we talk about: where do you buy the cheap turpentine? [Everyone laughs.] And I really believe that, like a lot of trades—you know, my dad was an architect. He had a trade. And a lot of it was like, what kind of pencil did he use for what kind of drafting, you know, those sorts of things. And I see this with software developers too, right? Like software developers who love talking about what their IDE environment is or what keyboard they use. You really do become devoted to your tools. And so I’m curious as you lead an organization, are there specific kinds of techniques or words that you’re like, I started doing this in the last year or I stopped doing that, that you think I slash we could learn from? 

MS Well, I can give you an example. 

RB Yes, please. 

MS That’s very contextual and specifically related to pronouns. Because like Gina said, we send a lot of decks in our line of work. Postlight’s decks include the people who contributed to the work. That said, when we’re throwing something over the fence and we’re not going to be presenting it live right away on those artifacts for now, we don’t include pronouns. When we come together and we’re live and there are real humans speaking to each other face to face like we are now. Then when there’s an introduction slide or a section, we very often include pronouns, again, tuning for the culture of the people that we’re meeting with, the composition of our team. So we try to calibrate for the context that we’re in. And the point that you made about pipeline for example is really interesting to me because when I think about the work that we do, which I would describe as very comfortable knowledge work, we’re constantly looking for efficiency and trying to be faster and quote unquote more productive. And without realizing it, we start to rely so heavily on metaphor in our language because metaphor is a shortcut, it’s a shorthand, it’s a proxy, but we forget that shared shorthand among people can reflect bubbles or privilege or lack of privilege or experiences or lack of exposure to experiences. It’s so easy to use metaphor when you’re trying to go super fast.And it becomes very habitual and it’s important to be mindful. 

[18:28]

RB Well, I mean, I’ll also just say, so many of these things are greatest strength and greatest weaknesses—the same thing. I love metaphor. I love storytelling. I love analogies. 

MS It’s a powerful tool. 

RB If there was a world championship of analogies, I would try to learn and win and try to compete in such a thing. But that power can also be sloppy and misused. So I think it’s a great example of the way in which we ought to be just paying close attention. 

GT It’s true. 

MS Yeah. And it’s, it’s something that is much more apparent to me. For example, you notice that I used the war metaphor. It’s much more obvious to me in writing when I’m looking at the words on the screen. 

GT Yes. 

MS I’m often working with my team on storytelling and when you do it on screen, in writing, it’s clear that it’s a shortcut that you’re taking. And I’ll often give comments in documents: this feels like a placeholder. Like this is the right idea. You’ve solved it, but this is placeholder text because you were going really fast. So that’s awesome. Just go back and put in the real words later. 

RB Yes. 

MS But it’s much harder to do that when you’re speaking live.

[19:29]

RB When you’re speaking.

GT Yeah. It’s true. The thing that I worry about a lot, particularly in our business, professional services business, where you’re solving a problem for a client, which necessitates allocating a team and them spending time. There’s this phrase, that I cringe inside: billable resources. That’s a phrase that’s very commonly used in our business: billable resources. But it feels—it’s very dehumanizing, right? 

MS It’s gross, yeah. 

GT Especially with the pandemic, it’s gross, right? The pandemic we’re all remote. And we’re not as connected as we used to be. And I think it’s just going to be so easy to start to think about people like Lego pieces and not like human beings with like goals and aspirations.

RB I think actually the entire—the entire idea of calling it a human resource is that as well.

GT Yes. The human capital. Yes.

[20:12]

MS I want to come back to something you said a couple of minutes ago, which is important I think for—maybe we have some listeners who are not as familiar with Bloomberg Beta and may not realize that you like to be the first money in. You focus on investing in founders and companies in the earliest possible stage. 

RB Yes.

MS Why is that? 

RB We don’t want a business relationship to be merely a transaction. It does need to be a transaction on some level because that is what a business relationship is—you are explicitly or implicitly exchanging something. That to me is sort of the definition in some ways of what constitutes a business relationship as opposed to other kinds of relationships. But the earlier you are in a company’s journey, the more you are focused on, well, we talked about the irrational and the rational. The rational becomes more legible the further you go. It’s obvious what market they’re in. It’s obvious how much money they need. And we like to be involved at the irrational phase. We like to be involved at the phase where you can’t quite justify to somebody why you would do this. And that produces a feeling for us, which I think is true for many people in many occupations, but almost always true for company founders, of it’s more than just work. Work is more than just work. It’s a thing we spend a lot of our days doing. It can be too much of a thing, right? It can be, you know, when somebody says—back to metaphor and analogy—founders will often say like, oh, this startup is my baby. And I’m like, woah, time out, time out! Like nobody dies if the startup doesn’t work out. Like let’s not, you know—[Gina laughs.] But that metaphor has a lot of power for that reason. 

MS Right.

[21:54]

RB And in that is a recognition that when you are invested in your work, it is more meaningful than being a human resource, right? You’re not just a Lego building block. You are more than that. You are this indescribably unique thing, which is a human being. 

GT Yep. 

MS It’s interesting, you know, how these things all happen at the same time. A reporter that I used to work with at Bloomberg, Aki Ito—a phenomenal reporter. She’s no longer at Bloomberg, she’s at Insider now. She published a story today about trends in the workforce where essentially employees are actually looking to create more boundaries between work and the rest of their life. And they’re quote unquote strategically dialing back at work. They’re not lazy or unambitious or burned out. They’re just done letting companies squeeze free labor out of them.

[22:51]

RB Aki’s so smart. So smart! 

MS She’s a phenomenal reporter. Everybody should read this reporting. So the question is, given these trends, which are not disconnected from what you mentioned earlier, is that changing what you’re seeing in founders? Can founders come to the table during the irrational phase with more balance and boundaries or do they have to be temporarily all in? That’s a poker metaphor. 

RB Great question. Haha. I like that. We have from the very beginning believed that it is possible to be an extraordinary founder without it being all-consuming in your life. Because if you believe it has to be all-consuming, what you’re effectively saying is no parent should be a founder. Nobody who’s falling in love should be a founder. You know, there’s got to be room for the experience beyond. And one of the reasons I am not a founder now is it was so emotionally all consuming for me. I mean, my wife said—and I don’t think this was a threat I think it was more of a prediction—she was like, if you start another company we’re going to end up divorced. And she didn’t mean it. I didn’t take it as a threat. I took it as an honest, almost anthropological observation of what was happening to her husband, who— 

MS That’s very generous of you. 

GT Spousal real talk. That will really pull you up short. [Laughs.]

[24:10]

RB I mean, look, I didn’t have the skills and at some point in the distant future, might I build up more skills and be able to do it? Sure. It’s one of the reasons by the way that I think sociopaths have advantages as founders is, if you don’t feel empathy, I mean, it’s horrible because we don’t want sociopathic founders. But if you don’t feel empathy, all that stuff is a lot easier. And I think that the conversation about drawing boundaries has now entered the acceptable parlance. I mean, you know, one of the investors in my company when I co-founded a company, I remember he said to me and my co-founder, he was quoting somebody else. But he said something like if you don’t come into the office on Saturday, don’t bother coming in on Sunday. 

GT Sunday—I’ve heard this yes.

MS And I was like, ha ha. That’s funny. And at the same time, let’s acknowledge the reality that in every wildly successful startup that I know of, there are periods where the intensity and duration of the work breaks the ordinary frame. But I mean, I’ll give you two other observations on it. One is sustainability. And here’s what I mean by that. If I go to a founder of a company and I say, Hey, founder, what’s the most precious resource in your company? What’s the most precious asset in your company? I’m intentionally using a kind of anodyne word. Whatever they’ll think of they’ll think of. And they’ll be like, okay, how do you protect that resource? How do you make sure it doesn’t get overused? How do you make sure you can use it for the long term? You know, whatever you would need to do. And now imagine that resource is you, because that is the truth, and turning it back on yourself and saying like, if this company’s gonna thrive, I need to thrive, is important for success. And then the other thing I’d say, and this is, I’m gonna get a bit more meta, but lowercase M meta, not uppercase M Meta.

GT Okay good. We’ll take the lowercase.

[25:55]

MS There is this weird yin/yang kind of relationship between the capacities we have and the choices we make pushing an opposite direction. So let me explain what I mean by that. I used to work with MySpace when MySpace was a thing. News Corp acquired it. We worked closely together when they bought, I sort of stopped working with them as closely, but they bought Photobucket. And I remember Photobucket has real costs around storing photos. At roughly the moment when storing content becomes roughly free, approximately, is the moment when Snapchat becomes popular and people specifically seek out ephemerality. I have a theory that if we ever discovered immortality we would have elective death for sure in society. [Gina laughs.] 

MS Oh, a hundred percent, a hundred percent. Because we always want what we can’t have. 

RB Yeah. By that weirdo same token line of thought that same, you know, philosophical belief. It is the technological fact for many of us who work in office or information-based businesses, work-from-home-based businesses—not office-based businesses—that the moment it became possible for us to have 24/7 connection—which of course was already happening with mobile phones and email, it started early for many people, gradually increased from Blackberry and then the pandemic made it everywhere—is the moment we get good at drawing boundaries. 

MS Right. I mean, I’ve said this in many contexts recently, especially at work: the pandemic dramatically accelerated a whole lot of trends that were already sort of creeping along, whether it was grocery delivery or e-commerce or whatever might it be, but also how we boundaries our relationship to work, and in many ways, speeding towards whatever the future of work is. I think the pandemic accelerated all of it.

[27:51]

RB Yeah. Yeah. I mean, I think what’s interesting about it is I agree with that for certain kinds of work, for other kinds of work, of course, you know, I don’t know what the pandemic accelerated. If you are—were working in food service for example—10% of the economy. 

GT Right. 

RB But it may have accelerated things. For sure one of the things it accelerated was willingness to try software. 

GT Oh for sure. 

RB So there’s a magical piece of data that I wish I had, which is the average number of new logins that a professional created over the course of a year per year, pre-pandemic and post-pandemic. My guess is it went from one or two for the median person to 10 to 15, something like that. That’s my totally unsubstantiated guess.

GT And I mean, older relatives of mine suddenly became very interested in how to video call. 

RB Yeah. 

GT Right? Because they were like, well, how do I do this? 

RB Totally. 

GT So I had my, you know, my mom sending me emojis and hearts over Slack because she missed me.

[28:50]

RB And I think that was for sure an acceleration. Other things I think were just honestly distorted in weird ways. And I think work from home is one that, you know, I don’t think we would’ve ever had something. It’s not like we were on some trajectory to everybody working from home. It may be that we overshot what the natural equilibria are. And I think that what we’re gonna end up with is instead of a monoculture or monoculture with exceptions of office culture, like the monoculture was five days a week in a physical office. And there were exceptions, there was that organization here and there and you could call it a trend, but it didn’t seem statistically—we studied this a lot, you know—big enough to be a trend. Before GitLab, I used to say to people like, what’s the most successful company you know that’s fully distributed? 

And the two examples you would hear were MySQL, which is a great example but open source software is a special case, and Automatic, which while Automatic—very important company—is not in the scheme of capitalism all that statistically significant. So I think we got pushed into experimentation. And as a result right now, it’s like the roulette—uh, metaphor—the roulette wheel spinning and dozens of balls are bouncing around and they’re going to settle into different pockets on the wheel. Some will settle into fully distributed. Some will settle into five days a week in the office. Some will settle into four days a week in the office. Some will settle into some partially in the office, some will do hub and spoke. Some will be some roles this way, some roles that way. And we’re only now developing the nomenclature for that. 

We invest in a company called Range that does software that helps teams perform better. And they came up with this tracker of work from home during COVID. And one of the cool things about the tracker was just that they had to develop names for all these different Rubik’s cube variations of what we were doing, where before we would say like in-person or distributed or hybrid, which just seems like a pretty weak—you know, that’s like having two words for weather of like wet and dry. It’s like, no— 

MS Right. Now we need a whole new schema for work.

RB Yeah, exactly. We need a schema. That’s the perfect analogy for it. 

MS Yeah.

[30:49]

GT Yeah. Roy, you, you seem incredibly calm and centered for a person who was working in venture capital in 2022, when things are really wild. Frothy. I saw you quoted in a New York Times article and I was like, oh, that’s my man Roy. 

RB You and my mother. [Everyone laughs.

GT And I mean, things are—the bubble and Web3 and the money and the economy and all the things that are happening. It just all feels super intense, reverse pitching. What’s going on? What’s Bloomberg Beta’s approach or like, what is your posture in this environment? 

RB Thank you for noticing all of that. And you know, the reverse pitch is when the fund pitches itself to founders, which we actually did our first public reverse pitch earlier this year, which was a lot of fun. It was a difficult and important exercise for us to go through because we thought of ourselves as people who were pitching constantly, but it’s different when you’re like, okay, is my deck and I’m going to do the thing.

GT Yeah. [Laughs.]

[31:47]

RB I feel like I go through bursts of complete overwhelm. I used to feel very confident that I could find the communities where the best founders were emerging from. Now I think there are so many more of them that it’s like, I don’t know which way to look. And that’s good, but it’s also challenging. And you know, look any VC who hasn’t had one or two of the best years in their life in terms of financial performance, the last one or two years should quit immediately because—yeah, it’s been like a gale force wind behind us. And at the same time, I think calm is an attitude, not a personality trait, meaning like it’s a thing you choose and work on. 

I remember one of my early experiences, working experiences, was when I was in grad school, I was an intern for a summer at NBC news. And it was the summer when—I’m going to date myself here but fine—when JFK Jr.’s plane crashed, which in the scheme of news is like a day-of news emergency, you know, nothing like what everybody covering Ukraine is going through now, but still a pretty big event for that summer. And my boss who went on to be the president of ABC, a great guy, Ben Sherwood, he kind of like beckoned me over as everything’s just frantic and everybody’s running around and he’s like, you see the three of us who are, I forget what their titles were, senior producers, something like that on the show—you see how our heart rates barely seem to be moving. He’s like, that’s what we learn. And I was like, damn that’s cool. And that was really inspirational to me of trying to cultivate a sense of presence and calm. I didn’t have those words for it at the time. I think I had to go a little new-agey Northern California, you know, for that to arrive. But there is something powerful there. 

And at the same time, the fun thing about this line of work is a) it gets constantly reinvented. So I get to kind of keep doing things. And b) it’s way easier than starting companies. It’s way easier than lots of other things. And so if I’m stressed out by doing it, how can I possibly expect a founder to keep their shit together? [Gina laughs.] And so part of it is we want to be a little bit of a pain sink for the pain that founders feel. That’s what I always say—

GT Aw.

MS A pain sink, yeah.

RB My co-founder Julie Uhrman at OUYA, the company we co-founded—she was the pain sink. And it’s like, God, if only the investors could have been part of the pain sink, it would’ve been a lot easier for her and for all of us. [Gina laughs.

MS I want to repeat something that you said, because I think it’s that important. You said being calm is an attitude. It is not a personality trait, right? Which means it’s something that you can practice. You can learn. What’s your practice? Everybody has their things that they like to do. What’s your practice? 

RB I have been a Guinea pig in my own experiment on myself in this way for a long time. My basic attitude is if it doesn’t cause me lasting damage and doesn’t hurt somebody I love then if it might help, I’ll try it. And so in no particular order—actually that’s not true—in the order of the order they’re coming to mind, I’ll say sleeping seven hours at least per night. 

MS So important. 

GT Big fan. 

[35:00}

RB Yeah. And I’m privileged that I have the kind of life that I get to do that. I mean, sleep is a privilege. Therapy has been extremely important for me. Medication as part of that  has been extremely important to me. Meditation has also—meditation, medication, I don’t know what the third one is, perspiration? I’m trying to get into exercise and I find it so boring. [Everyone laughs.] And I did one of these tests that my doctor did that apparently I have some elevated level of some enzyme that breaks down dopamine. So like I can’t get runner’s high as easily as another person. 

GT So sorry. 

RB Apparently. Yeah. And it’s like, well, you know, that’s my cross to bear. I’ve gotten into some things that are a little more like intellectually stimulating forms of exercise like boxing. And then the one that has been probably the single best return on time, if you will, is I did one of these week-long group programs. It’s called the Hoffman process. It’s run by a  nonprofit called the Hoffman Institute. I swear to God, it’s not a cult, but it’s a thing that a bunch of people in tech media have done. And I learned about it from them. And then I learned lots of folks have done it. And that was just like, taking a week where they like, literally put your phone in a box and it’s like, now you’re going to work on you. It’s like, when do you ever get to do that in your life? 

GT Never. 

RB And that was a great privilege to get to do it to the point where I told my team, I was like, if any of you want to do it, you don’t have to take vacation and the company will pay for it. Because it’s that valuable professionally. 

GT Wow. 

RB So those are a few of mine that have been useful. Plus, you know, getting the shit kicked out of you by people all day long every day, you know, meaning—okay not all day long every day, but like, you know, talking to somebody and being like, oh my god, I stressed that person out. Or I said something offensive by accident. I mean, it’s what my coach and actually my coach has been essential in this too, is, you know, she calls it AFOG—another fucking opportunity for growth. 

MS That’s amazing.

[36:54]

GT That’s wonderful. And such an exec coach thing to say.

RB She’s great, Carole Robin, she’s amazing. And it’s been like a decade-long relationship and it’s like every week I’ve got another one of these opportunities for growth. 

MS I feel like I run into AFOGs every week, all the time.

GT Multiple times a day for me at this point. For sure.

RB That’s a good sign, too. I mean, if you weren’t running into that, you’d be bored.

GT I’d be bored. Yes. And I don’t wanna be bored. Yeah.

RB Bored or a sociopath. And maybe that’s a good title for a life’s biography, Bored or A Sociopath. Avoid both if you can. [Gina laughs.

MS Well, Roy, next time you come to the East Coast, you have to let me know. I will bring you to my dojo and teach you some Japanese swordsmanship, which I think you would really enjoy as a very cerebral form of exercise. It sounds like it’s right up your alley. I have to be honest. 

RB I would love that. That would be so, so fun. And I’ll also just say gratitude, you know, just to add in, we invest in a company called Jam that does short form audio, like minute-long audio, just a minute jam.ai. And you can get like a minute-long, little gratitude thing as part of your news playlist. And even like those little tweaks have been very helpful to me. And then the last thing is focusing on things beyond myself. We do get drawn into a lot of work around how we make work better. My wife and I are very politically active trying, you know—we get out the vote and organize a community of tech people who wanna engage in the fight by using the tool of their skill and their money through philanthropy. That’s called First Principles. It’s a thing we do with Stanford. And so those things I can get to justify both as being part of my occupation because they deepen my understanding of how people build things in tech and introduce me to people we can work with and get to keep me sane by trying to do something constructive out there.

[38:40]

GT This is all great advice. You’re actually—I’m like quietly recommitting to my own self-care here as you’re talking Roy.

RB Well, except as you know, just to say, I don’t believe in advice and you know—you are welcome as a guest anytime on This Is Not Advice, which is this like once every, so often, twice a week, something like that, short form  tips about work thing that I do. 

MS That’s great.

RB  It was my pandemic project. And now we’ve got a website at, thisisnotadvice.work people can look up. It’s like, oh, I’ve never fired anybody. What do I do? Like those kinds of things.

[39:10]

GT I’m so glad you brought it up because This Is Not Advice—I spent just like delightful hours reading through it and enjoying it and looking at the social posts that had kind of been the seeds of it. And I really, really enjoyed it. It’s community-edited. It’s kind of a Wiki ituation?

MS Yeah, that’s the idea. At one point I was like, why is there not a What To Expect When You’re Expecting about work? There totally should be.

GT Yeah. 

MS But the difference should be, it shouldn’t be written by a single person and it shouldn’t be static, which I know that any book published annually isn’t quite static, but I was like, hmm. It turns out we have a technology for long strings of text communally edited and kept updated. And that’s open source, like all the ways—the mechanism of open source. So it’s hosted, you know, on GitHub, we use GitBook as the renderer for it, but you can go edit GitHub. And I would love for people to come in and add their own and make changes and that kind of thing. And I’m also aware that for any open source project to succeed, it usually needs a very strong first draft and an author who is, or I think of myself kind of as the editor of it, who’s willing to be the person to drive it forward and that it takes time. 

MS That’s a great point.

[40:14]

GT Yeah. I mean, it’s really true. And, this is so in the spirit of Bloomberg Beta, just that sharing what you’ve learned and what you know. I love is that the first sort of menu item on thisisnotadvice.work is managing yourself because this was the hard lesson that I had to learn as a leader is that is a huge part of the job. Almost all of the job is managing my own emotions and reactions and like having self-awareness around my own and the things that I’m most afraid of in situations, because that’s where the reactions come from and the stuff that I regret later on comes from. And so, I really, really enjoyed it. I recommend it. And we’ll link this in the show notes, along with some of the other companies and articles we’ve talked about during the episode. Roy, I’ve just absolutely loved catching up with you. It’s been way too long. I so appreciate you coming on the show today. This was wonderful.

MS It’s been great.

RB Honestly I could keep going and talking with both of you for hours and I’m grateful. 

MS I think we could. 

RB Yeah, no, I’m grateful for the chance to do it.

GT Roy, if our listeners wanted to learn more about you or Bloomberg Beta, what’s the best place for them to go and and check it out? 

RB Well, bloombergbeta.com is where we try to be as transparent as possible by publishing our formal internal operating manual. My social media poison of choice is Twitter. And I’m @roybahat on Twitter. And I’m grateful that you both do this podcast and built Postlight and here’s to many more collaborations to come.

[Outro music fades in, ramps up.]

GT Yes. Thank you so much. 

MS Thanks, Roy. Great to see you. 

GT For those of you who are listening, get in touch with Postlight: hello@postlight.com. We’d love to hear from you. We’re a strategy, engineering, design firm based in New York City. Numbers are getting better. Stop by the office. We’re at 5th Avenue, 17th Street. We’re not there right now, but we’ll be back in soon, I think Michael, more regularly.

MS In the meantime, new episode out every week. Thanks for listening. 

MS Bye everybody. 

GT Talk soon. Let’s get back to work.