Slack’s Stewart Butterfield: Collaboration Means Leadership From Everywhere

Spencer Rascoff

Spencer Rascoff serves as executive chairman of dot.LA. He is an entrepreneur and company leader who co-founded Zillow, Hotwire, dot.LA, Pacaso and Supernova, and who served as Zillow's CEO for a decade. During Spencer's time as CEO, Zillow won dozens of "best places to work" awards as it grew to over 4,500 employees, $3 billion in revenue, and $10 billion in market capitalization. Prior to Zillow, Spencer co-founded and was VP Corporate Development of Hotwire, which was sold to Expedia for $685 million in 2003. Through his startup studio and venture capital firm, 75 & Sunny, Spencer is an active angel investor in over 100 companies and is incubating several more.

Slack’s Stewart Butterfield: Collaboration Means Leadership From Everywhere

Stewart Butterfield is the co-founder and chief executive officer of Slack, a collaboration hub beloved by more than eight million daily active users. In this episode, Spencer joins Stewart at Slack's San Francisco headquarters to discuss their recent partnership with Atlassian, Slack's unique origin story, managing through growth and adversity, and how Slack is fundamentally changing communication at work.


Press Play to hear the full conversation or check out the transcript below. You can also subscribe to Office Hours on Apple Podcasts and PodcastOne.

Spencer Rascoff: Today I'm in San Francisco in the offices of Slack, and I'm with Butterfield. Stewart, thanks a lot for having me. It's great to have you here.

Stewart Butterfield: My pleasure.

Rascoff: So, congratulations, first of all. The timing of this worked out great. There was some huge news that came out about Slack and HipChat. Why don't you just share the news, and we can talk about it.

Butterfield: Sure.

Rascoff: What did you announce?

Butterfield: We've been working with Atlassian for a couple of years now on general partnerships. So, we make Slack the hub for collaboration or messaging for work or however you want to characterize it, and they make Jira, which is a really popular bug and issue tracker ticketing system used for all kinds of things. They make Confluence, which is like a Wiki/knowledge management tool, Bitbucket, source code control kind of like GitHub, and a whole bunch of other products.
And they also had a product called HipChat traditionally, and then about a year ago they introduced a new product called Stride which was their replacement for HipChat, and both HipChat and Stride were competitive with Slack. We still worked with them really well because we collectively had, at this point, hundreds of thousands of organizations who were using Slack with at least one Atlassian tool, like — I forgot to mention — Trello, task management application.
And we had no problem competing with them and cooperating, and they didn't either, but I think they came to the realization that the resources that they were investing in those products was probably better invested in their core products, which are, you know — in terms of market share, in terms of revenue — are much, much larger and go deeper on the partnership. And I think that was a really smart move, you know, very well-rewarded by the market and analysts. I got a lot of congratulatory emails saying that was brilliant, and I said, “We executed well, but I've got to give them credit for the idea." And I think it was a really unusual move for someone to make.

Rascoff: Yeah. I've never seen — so, what they basically did was they said they were gonna wind down HipChat and sell you the customer list and the IP —

Butterfield: Mm-hmm. Not even the customer list.

Rascoff: OK.

Butterfield: We're working together with them. So, we built a whole migration tool. They're messaging all of their customers, and definitely no one is being forced to migrate, but we wanted to extend the same pricing that they had to all those customers and just make it as easy as possible for people to move over.

I think there's a long history — if you go back to, like, what Microsoft looked like to IBM in 1982, or what Google looked like to Microsoft in 2001, or what Facebook looked like to Google in 2006-2007 — of a smaller, focused start-up with traction versus a larger incumbent that has multiple lines of business, and there's just a real advantage, I think, that you get in terms of the experience you can provide to customers and the kinda clarity and focus. So, I think there's — that's not always true, sometimes the big company squashes the smaller one, and in fact maybe that's more often true — but there's definitely a handful that make it out. So, I mean it feels good, but it doesn't feel good because that came at the expense of someone else, you know.

Rascoff: Right.

Butterfield: That feels good because we have thousands — tens of thousands of customers tweeting stuff, like, every day, posting to Facebook, telling their friends, insisting at their new employer that they evaluate Slack 'cause they used it at their old employer because they really like it.

Rascoff: I get the sense that the culture is not a competitor-focused culture, it's more of a persona-focused culture, customer-focused.

Butterfield: Yeah.

Rascoff: Employees come here every day trying to do the right thing by your users, and sort of whatever happens in the competitive landscape happens. Is that fair to say?

Butterfield: Yeah. No one will ever get fired because they were too good to a customer.

Rascoff: Right.

Butterfield: Including “good" in the sense of lost revenue opportunities or deferred revenue for us. We really believe in the long run — and I want to be doing this for the next 20 or 30 years, and, you know, it'd be great if the company existed for a couple hundred thousand years, couple hundred million years, who knows. In the long run, the measure of our success will be how much value we created for our customers. 'Cause you can always be the exploiter, you know, you can always be extracting more value than you can create but not for long. That just doesn't work for the universe for very long.

Customers are not gonna consistently choose Slack every year, every year, no matter what happens in the marketplace, no matter what other products arise, what other systems, if we're just trying to suck more money out of them and not make it actually something that's worth their while. I mean, the ideal case is for every dollar they spend with us they're getting back $10 or $100 or who knows in value. So yeah, we're definitely not focused on what competitors are doing, we're aware — we actually have a saying inside, “Competitor aware, customer obsessed."

Rascoff: I like that.

Butterfield: Yeah.

Rascoff: So, my first start-up, Hotwire, was very competitor focused. We were really focused on Priceline, and Zillow, my next start-up, is not so competitor focused. We're really consumer focused and persona focused. And it's a much more inspiring place to work when you're persona focused and not competitor focused. It's a little bit — I don't know, it's a little bit hollow, almost, to be overly competitor focused.

Butterfield: Yeah. I think it's easier for us to take that position than many other companies. If you're one of, I don't even know, let's say 1,200 restaurants in SoHo, in New York.

Rascoff: Right.

Butterfield: People have a lot of choice, and they're also not gonna go to your restaurant every time. And for Hotwire and most other travel sites, it's like it's a purchase-by-purchase decision, and people might have three tabs open —

Rascoff: It's much more zero-sum, yeah.

Butterfield: Yeah, and they're looking all over the place. Whereas — and certainly people can evaluate all kinds of software that they might use in the enterprise, but the commitment to actually make a purchase or invest is, like, something that happens over the course of months, you know.

Rascoff: Right.

Butterfield: And it's a much bigger just in terms of, like, literally the calories, like the glucose burned in their frontal cortex of the human beings who are doing this — is, like, a million times greater 'cause you have to shift the behavior of, you know, depending on the size of the company, dozens of people, hundreds of people, thousands of people, against habits they had formed over, like, the last decade or two.

Rascoff: So today, Slack is incredibly successful, of course, riding high from this recent announcement, but that's just a proof point. You know, so we don't need to dwell on it. It wasn't always that way. So, Slack rose from another company that was not as successful, so can you describe the founding story and sort of the early days of how Slack got started?

Butterfield: Sure. Here is the fastest possible version. Back in 2002, in, like, the really dark days — post-9/11, post-WorldCom and Enron, post-dot-com crash, NASDAQ down 80 percent, S&P 500 down 65 percent — we started a web-based massively multiplayer game company, which was not very well-timed. That ended up turning into Flickr through other means. Flickr got bought by Yahoo. A group of us went to go work for Yahoo.

Nine years — or sorry, seven years — later, 2009, we decided to try it again. We started another web-based massively multiplayer game company, which also failed. After about three and a half years, we had 45 people working on it and a pretty eclectic group because there's, like, some really serious, hardcore back-end engineering challenges, but there's also writers and artists and animators and musicians, and there is, of course, a business operations team and customer support.

And over the course of those three and a half years, we had started using a pretty ancient Internet technology called Internet Relay Chat, or IRC, which predates the web by a couple of years. And over the course of that three and a half years, just, like, one at a time and a pretty jury-rigged, hacky fashion, fixed the things that we thought were really annoying, like the kind of — the most irritating problems and challenges we had around internal communication or, conversely, the opportunities for improvements that seemed most obvious.

And then over the course of these years, we had this system for internal communications where it was a real virtuous circle; the more people paid attention to it, the more information we would route into it.

Rascoff: What did you call it internally?

Butterfield: It didn't even have a name. I think this is one of the reasons it had such incredible product market fit is there was, like, no ego involved in this. There was no speculation about what a user might want or like. This was just, like, how can we spend the minimum number of minutes to fix or improve this and then go back to what we were supposed to be doing and —

Rascoff: And it was just used for employees, the 45 employees that were working on this game that was not finding traction in the marketplace.

Butterfield: Yeah. Like, I don't even know if you — or if I did an interview at that time and someone said, like, “How do you all work?" I probably would have mentioned it, but it wouldn't have seemed very significant. At the end of the process, though, when we decided to shut down the game, we realized, “Hey, we would never work without something like this again, and probably other people would like it."

So, we had this blueprint which we executed against, and as soon as we put it in the hands — I mean not as soon as, 'cause the first couple customers are almost impossible to get. We had to beg our friends to please try it, please try it. 'Cause one of the challenges for Slack and things like it is you can't unilaterally decide — I mean, you maybe can 'cause you're the CEO — but one can't typically unilaterally decide that they're gonna use Slack to communicate with their team; everyone has to agree. Whereas somebody like, say, Dropbox — I've been paying for Dropbox for seven years or something like that. I'm a very, very happy customer — I didn't want to have to back anything up. I have multiple computers, seemed like a great solution. I just did it, but you can't do that with Slack, right? You need to get at least two people —

Rascoff: Right, you need buy-in from the rest of your —

Butterfield: Yeah, yeah.

Rascoff: Right.

Butterfield: And that needs to happen not, like, sequentially over the course of a year but more or less around the same time, and it's disruptive 'cause it's a change to how you communicate internally. So, I don't want to underplay that as a challenge. But once we did get groups using it, we found they just kept on using it, and the usage inside those companies grew, and people were very happy. And the same thing happened for them as happened for us: the more information you routed into it the more attention people paid, and the more attention people paid the more information you added into it, until, like, finally there was one kind of focal point for where work happens across the whole organization.

Rascoff: So, when you pivoted this gaming start-up to an office collaboration technology start-up, were there some people that either said, “Hey, I'm not in on that next mission," or people that weren't a good fit for what you needed?

Butterfield: Oh no, I mean — the actual shutdown — I'm glossing over the trauma.

Rascoff: OK.

Butterfield: It's pretty brutal. I mean, there was 45 people, we laid off 37 of them.

Rascoff: OK.

Butterfield: And, you know, for entrepreneurs in the audience who have been doing it for a while I'm sure they'll recognize the ups and downs. But I mean, first of all, it's humiliating personally 'cause, you know, I put a lot of my own credibility on the line, and I talked to press and investors and saying we're gonna do this and that, and then it doesn't work. And that feels bad for me individually. But much worse is the fact that I convinced most of these people to come work at the company and to give up some other opportunity that they had.

Rascoff: Right.

Butterfield: In some cases, to move to a different city. I mean there was a moment when I was announcing it internally where I kinda was just looking around the room while I was talking. First of all, I started crying almost immediately, before I got the first sentence out, but then I, like, locked eyes with one guy who, just a couple months ago had moved from a different city, away from his in-laws who were helping take care of his at that point, I think 18-month-old daughter and buy a house in this new city. And then I was telling him, “Sorry, you don't have a job anymore."

So, happy ending on that one because we hired him back about six or nine months later and he was a very early Slack employee and happy. But yeah, I mean, we don't have a big need for musicians at Slack or animators or level designers or a lot of the disciplines. So, that was, like, a — it was a pretty dark time for a while and took us a few months to — because we had money left, we were able to do it in a relatively elegant way, so a couple months to kinda clean it up.

Rascoff: Right.

Butterfield: So, offer our customers their money back, or we could donate it to a charity on their behalf, or we could keep it, to put a lot of effort into making sure that people got other jobs. We built, like, this whole website with everyone's resume and portfolio, and we did some interview coaching and wrote reference letters and got everyone else a job.

Rascoff: This was in Vancouver mostly.

Butterfield: This was, yeah, Vancouver and San Francisco, but Vancouver was the larger office at that time, and then — so, that's the end of 2012, beginning of 2013, and we start making Slack middle of 2013. We had started using it ourselves and we tried to get some friends to use it. August of 2013, we did private beta, which we called a “preview release" 'cause we didn't want people to think it was flaky. February of 2014, so four and a half years ago, we officially launched it and started charging and stuff like that. So, it was really fast, like 14 months.

Rascoff: Right.

Butterfield: And by the time we launched it, there was about 15,000 daily active users, and the teams were really sticking and there was just — like I said, this incredible product market fit out of the gate, which, to be honest, I think has propelled us to where we are today, four and a half years later.

Rascoff: I mean, managing through adversity for a leader but also for the whole company frequently makes the company all that much stronger and better. Probably somewhere in the Slack DNA, and definitely in your management DNA, are lessons learned from that period.

Butterfield: Yeah.

Rascoff: As the company has scaled to today — to 1,000 employees, eight offices — what are some lessons that you've learned as a leader through that growth period? How have you changed as a leader and as a manager? You know, what are some things that other listeners can learn from having managed through that growth?

Butterfield: It's more like what hasn't changed? I mean, I have been making software for about 25 years, like professionally, and I'm 45 now, and I'm good at product design, good at software development. I'm probably not gonna get any better at this point, not because I'm so great at it but just because, like, now I'm relatively old, and I've been doing it for so long that if I was gonna get better it would have happened in the last 25 years. And I'm sure I have other significant skills as well, but I feel like that was the strength in my career that got me to where I am, and now that's largely irrelevant. How good — I mean, I'm sure —

Rascoff: Because you have a team that's doing the —

Butterfield: Yeah, 'cause there's 1,200 employees.

Rascoff: Right.

Butterfield: And I'm not gonna make any — you know, like, I could make 10 basis points and, like, one-tenth of a percent worth of the significant decisions on the product development side, and hopefully I make a contribution on strategy, but my job is just completely different, and it took me a long time to figure it out. And I'm sure I wouldn't have said this to you at the time, but if you asked me two years ago what my job was, I would have thought inside my head, very secretly, only to myself, that my job is to be smarter than everyone else and to make all of the really important decisions.

And I didn't mean that, like, coming from an egotistical place, I just felt the pressure of, like, I need to be able to approve anything that's happening. I need to be able to, like — when there was an irreversible, very significant decision for the company, I had to be the one to make it, which, you know, I think actually is still a little bit true today. But when there was irreversible-but-unimportant decisions or reversible-but-important decisions, I didn't need to be the one making those.

So, it took me a long time to figure out what the job actually was, and to me there's three components. So, one, set the strategy and vision for the company, which sounds very lofty, but it isn't super time consuming. We had a great vision out of the gate. We had a great strategy out of the gate. Like, we haven't changed our pricing. In fact, we have set the — the pricing was proposed before we even started developing Slack, and we haven't changed it, and maybe there's better pricing, but it must have been pretty close 'cause it's working.

And the kind of — the positioning we put ourselves in, which is we want to build up to the edges of other software but not necessarily compete with them. We don't want to make document-editing tools, we're not gonna make calendaring tools, we're not gonna make, like, a bug or issue tracker, but we want to make your experience at each of those tools which you already use better because you use Slack.

The second thing is kind of a basket of governance, administrative, supervisory duties, and we have a great GC, we have a great CFO, so that actually doesn't take that much of my time either.

Which leaves a third bucket, which should be almost all of my time, which is ensuring that the performance of the organization, as a whole, is as high as possible. And I didn't think about that as my job, and because I didn't I also didn't delegate that. So, I think we were in a position a year ago, and I think we're still working out of this, where most of the executive team was making most of the decisions, you know. We would spend time, collectively, looking at spreadsheets where each row was a thing that someone was working on and saying, “Is this thing higher or lower priority than that thing? Is it the right team working on it?" And that actually would be fine at 100 or 200 people — it doesn't work at the scale that we're at now, and it's certainly not gonna work at the scale that we're gonna be at at a year and a half or two years from now.

Rascoff: So, setting the vision, but most importantly up-leveling the organization. A lot of that is around motivation, communication, employee comms.

Butterfield: Yeah.

Rascoff: So, the culture at Slack is — it seems very similar to ours. I mean, you have this phrase, “Work hard and go home." What does that mean, and how would you describe the culture here?

Butterfield: So, yesterday I did a new hire welcomes — I do, like, every two weeks — it's like the batch of people who started, and I tell them about that. I don't really actually know if we have it up at our new office, but we will at some point — we definitely had it up at our old office. And I say we had this thing up on the wall that says, “Work hard, go home." Pause, beat, beat. Everyone understood the “go home" part, and everyone laughs.

The work hard part — the point of the whole thing was we want to be able to hire all kinds of people.

Rascoff: Yes.

Butterfield: And some people got kids, and they can't stay till 8 p.m. or 9 p.m. or 10 p.m. Some people have other stuff. They're active volunteers in their community. Their church is important to them. They have hobbies that are significant. And if we can be disciplined, professional focused while we're at the office and really take the best advantage of those, I don't know, four to maybe six hours of really creative, kind of focused intelligent work, then we could all just go home earlier and do other things and rest up and kind of be prepared to do this for years and years — as opposed to play foosball for 45 minutes in the middle and then have a two-hour lunch and spend a lot of time talking about TV shows or going to karaoke that night or whatever it is. That was really important to us.

It took me awhile, until really recently, to think, “You know, we have mission and vision, strategy — we have values," but the thing that became most significant for me in thinking about what kind of culture we wanted to build were these four attributes that someone else mentioned to me, a guy named Suresh Khanna, who last I heard was the CRO at AdRoll, a retargeting company. And I was going for a walk with him once, and he mentioned just in an offhand way that he looks to hire people who are smart, humble, hard-working and collaborative. And for some reason that combination, that phrase really stuck with me.

So, like, a year or maybe two years later, I'm not even — I guess probably two years later, I realized, “Wow, that's, like, a really magical combination." And it's not that those are four important attributes and hopefully you have at least one of them as a strength but those in combination. So, you have probably worked with people who are smart and hard-working but neither humble nor collaborative, and there's certainly an archetype that comes to mind when I say that. Conversely, people who are collaborative and humble but neither smart nor hard-working — another different archetype that comes to mind.

Rascoff: Right.

Butterfield: And that's the thing that we want to cultivate. So, smart in the sense of being not high IQ, although that's a bonus if you have it, but oriented towards learning.

Rascoff: Growth mindset.

Butterfield: Yeah, and realizing that your intelligence and creativity are relatively precious things, and if you're going to be spending mental energy on something it shouldn't be something that is routine, that could be made into a checklist, that is kind of — like, there's no point trying to remember that stuff. Computers are relative to humans, perfect at remembering things. And humans are relative to computers; basically, we don't remember anything. Like, we don't — literally nothing. I don't know who I am, where I am, why we're in this room, like, just no memory. Computers can do arithmetic 100 trillion times faster than human beings — and by the way, with perfect accuracy — whereas no matter how good you are at doing math in your head, you're gonna get things wrong once in a while. So, I mean, those are kind of obvious ones. But how quickly can you improve the way that you work, and how steadily can you improve the efficacies? That's smart.

Humble is pretty obvious. Hard-working is pretty obvious. Although I have to point out that humility is kind of a fundamental one in the sense that being smart like that — understanding when you make a mistake and figuring out how to improve it — requires an element of humility. But the one that I think is gonna be least well understood is collaborative 'cause it's a pretty open word. It has a lot of connotations. It's kind of — it's difficult to know what someone means when they say that this person is collaborative, and here we mean something really specific.

Rascoff: That's very hard to evaluate in an interview as well.

Butterfield: Yeah, yeah, it is. So here, we don't mean like meek or submissive or deferential. We don't mean like you have a tendency to go along with what other people want, which I think is what comes to mind when people say “collaborative," at least sometimes. It's kinda the opposite.

But the difference between the best and the worst performing teams, I think, is much, much wider. Like 100 times wider than the difference between the best and the worst performing individuals. So, as long as you're hiring people who are basically competent, you're not hiring, like, completely incompetent people or, like, a bunch of thieves or something like that. You're gonna have better and worse employees, and better typically means not so much they have more talent at fulfilling the tasks — like their role-specific function, like they're better at Excel than the other people in finance — but that they elevate the people around them.

Rascoff: Right.

Butterfield: That they're an important contributor. They're kind of glue for the team. They drive more clarity and alignment. They give good feedback, and they're receptive to feedback and a bunch of other stuff. You think about, like, people that you've had to fire over the course of your career, or people you know of got fired — people do get fired for incompetence sometimes. The overwhelming majority is they didn't work well with other people.

Rascoff: Right, personal issues, yep.

Butterfield: Yeah.

Rascoff: In their relationships.

Butterfield: So, going back, the collaborative sense here is the opposite of those meek, deferential, submissive — it's leadership from everywhere. It's that you take individual responsibility for the health and performance of this team. So, when there are problems you help clear them up. When there is, like, low trust you help drive up trust. When there is a lack of accountability, when there's a lack of clarity around goals or objectives, you take responsibility for driving those up, regardless of who you are. So, I don't even mean just, like, the manager — I mean everyone.

And if there's a real, deep commitment across the organization to improve the performance of the team, everyone as an individual is better off, 'cause would you rather work on a high performing team or a low performing team? And obviously the whole company is much more successful as well.

Rascoff: I feel like I am a much better CEO today in my mid-40s than I was 15 or 20 years ago, because I agree with everything you just said, and I think it's super important, and when I was in my mid-20s I did not.

Butterfield: Yeah.

Rascoff: I didn't understand any of that.

Butterfield: Yeah. Well, I'm — good news, I'm mid-40s as well and would say exactly the same thing. Yeah, 'cause there's a real tendency to believe that it is, like, the heroic contributions of one genius software engineer or, like, one amazing marketer or something like that, and obviously individual contribution matters a lot, but —

Rascoff: Well, you know, it's nice. I mean, your product also speaks to this, right? Your product is about team collaboration, so it's obviously embedded in the culture of the DNA. As is sort of, like, you know, LinkedIn takes really seriously all these issues because the product is about that — it's about working well with others and collaboration and kind of being your best self at work, and Slack likewise has, you know, the product is that vision. But that's your philosophy background coming through, huh?

Butterfield: Yeah, it definitely is. There's actually one more kind of higher level thing that's going on, and that's over the last 30 years the tools for people to get their individual work done have improved dramatically. So, you imagine, like, how a recruiter gets stuff done in 2018 with LinkedIn, with an applicant-tracking system, you know, with tools to check their — well, resume scoring but also job description, language checkers and all this kind of stuff. Compared to walking into an office building and, like, with a pad of paper and writing down the names of all the companies and then going back to your desk and start making phone calls. Or a salesperson who has a CRM and has marketing automation tools and has lead scoring and has LinkedIn sales navigator, software engineer, you just go through the whole list.

Rascoff: And so, because they have more software to help them be more effective at work, what? Collaboration is more important?

Butterfield: Yeah. I think collaboration becomes the limiting factor.

Rascoff: Why? Oh, I see.

Butterfield: So, you think about it from your perspective, as CEO, if you could hire a magic consultant who would come in and through, like, GTD, time management, life hacks, whatever, would make everyone 10 percent more effective at the completion of their individual tasks, which is a significant component of their work, obviously. But people spend at the low end 30 percent of their time and at the high end 100 percent of their time on communication.

So, if you could have that 10 percent improvement in individual worker productivity, or the same magic consultant would drive a 10 percent increase in shared consciousness, like, knowledge of what people across the organization are doing, or 10 percent better understanding of goals, 10 percent more alignment. I mean, those things are harder to measure perhaps, but obviously more significant 'cause more incremental improvements in individual worker productivity are probably not gonna result in as much of a net change because nothing has happened over the last 50 years, with one exception: to improve the way that we communicate and the way we collaborate and the way that we share knowledge and the way that we get to that point where the team is working really well, and that's email.

And mail was a very, very significant step compared to, you know, mimeograph machines and taking paper and rolling it up into a little tube and sticking it into a cubby or interoffice mail or any of those kinds of things. But I think there is a second really significant change that we're part of — and by the way, if this was the industrial revolution, it's like 1870 —

Rascoff: And that change is improving communications in the office.

Butterfield: Yeah.

Rascoff: Email is — you think email is pretty outdated and not interactive, but messaging communication has —

Butterfield: It's a layer of communication that will be around for tens of thousands of years, probably. Like, it'll outlive most of us. And I mean this in a complimentary way, as the lowest common denominator form of communication.

Rascoff: Right.

Butterfield: Like, you can more or less guarantee that every other human being has an email address. But for internal communication, I think it's a pretty terrible choice, and the Outlook window for most people at most companies is that window they have into the workflows across the organization. It's, like, how budgets get approved, how job offers get made, how contracts go back and forth between legal teams, how decisions are communicated and memorialized. Like, it's just — it's almost everything. Your awareness of what's going on happens through that email window, and email is an individual-first mode of communication.

Rascoff: Stewart, thank you so much for the discussion, I really appreciate it. Congratulations on all Slack's success, and I am a happy user, and I look forward to continuing to be for many decades to come.

Butterfield: Yeah, thank you so much.

The post Slack's Stewart Butterfield: Collaboration Means Leadership From Everywhere appeared first on Office Hours.

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Venice-based Locket, the viral photo sharing app that made homescreen widgets cool, is now leaning into what LA does best: celebrity. Its new feature, Celebrity Lockets, allows artists to send exclusive photos directly to fans’ home screens. Early adopters include Suki Waterhouse and JVKE, with creators curating limited fan access to maintain intimacy and exclusivity. As Locket evolves from a casual social tool into a direct fan engagement platform, it’s becoming an increasingly relevant player in LA’s creator tech ecosystem.

🏈 Disney’s ESPN Plays Offense

Disney made a trio of bold moves this week that solidify ESPN’s future and its dominance in sports media. It’s buying out the NFL’s stake in ESPN, securing exclusive NFL Draft and behind the scenes content through 2033, and finally giving its standalone ESPN streaming service a launch date: August 21, 2025. That’s a power play straight out of Burbank. At the same time, Disney announced it will no longer report individual subscriber numbers for Disney Plus and Hulu, signaling a shift in how it wants investors and maybe consumers to measure success.

🗞️ The New York Post Bets on LA

In a sign of LA’s growing national influence not just in entertainment, but in news, the New York Post is launching a West Coast vertical called The California Post. With an editorial mission to cover the state’s cultural and political pulse, this move reflects a broader trend of major media brands planting roots in LA to chase both readers and relevance. For local media startups, content creators, and civic tech players, it’s yet another sign that the competition and the opportunity is growing.

Image Source: Meta

📱 Instagram Wants Your Inner Circle

Instagram rolled out a new set of features this week that prioritize connection with close friends. Users can now share what they’re doing, watching, or feeling with a smaller group, clearly borrowing from the intimacy playbooks of apps like BeReal, Snapchat, and yes, Locket. As social platforms shift from mass broadcast to curated circles, LA-based creators and consumer startups should take note: the next frontier might not be going viral, it might be going personal.

From star-powered lockets to streaming shakeups and platform reinventions, this week’s stories highlight how LA’s tech and media companies are rewriting the rules on connection and control.

Now onto this week’s venture deals 👇

🤝 Venture Deals

LA Venture Funds

    • Starburst co-invested in Madrid-based SpaceTech startup Orbital Paradigm’s €470,000 raise, part of an ongoing €2M funding round led by Akka. The company is developing reusable orbital re-entry capsules aimed at reducing costs and increasing sustainability for space missions. Starburst’s participation underscores its focus on backing innovative aerospace technologies with commercial and defense applications. - learn more
    • Rebel Fund participated in Orbital Operations’ $8.8M seed round, which came shortly after the company graduated from Y Combinator. The funding will support development of the company’s high-thrust orbital transfer vehicle, designed to maneuver satellites and other payloads in space more efficiently. - learn more
    • Fourth Revolution Capital participated in SuperGaming’s $15M Series B round, which valued the company at $100M, five times its previous valuation. The funds will help expand titles like Indus Battle Royale internationally and scale SuperGaming’s tools for developers in emerging markets. - learn more
    • Cedars-Sinai Health Ventures participated in Elion’s $9.3M seed round, joining NEA and others in backing the AI-powered healthcare research and intelligence platform. Elion helps over 60% of U.S. health systems evaluate emerging technologies through its structured vendor marketplace. The funds will support platform development, new product launches, market expansion, and team growth. - learn more
    • M13 led the $10M seed round for Kontext, an AI-powered contextual advertising startup emerging from stealth mode. Kontext’s platform enables real-time ads inside chatbot responses using large language models, and the funding will help expand its engineering team and develop image-based ad formats. - learn more
    • STORY3 Capital Partners made a significant minority investment in U.K.-based activewear brand Adanola, valuing the company at approximately $530 million. This strategic partnership brings STORY3’s deep experience in consumer brand scaling to support Adanola’s global expansion, particularly across the U.K. and U.S. markets. - learn more
    • Walkabout Ventures participated in OLarry’s $10M Series A round, which was led by TTV Capital and included Marin Sonoma Impact Ventures. The funding brings OLarry’s total capital raised to $14.5M and will be used to scale its AI-powered tax advisory platform for high-net-worth individuals and to acquire regional CPA firms as part of its growth strategy. - learn more
    • Glendon Capital Management participated in Grasshopper’s $46.6M funding round, which was led by Patriot Financial Partners, to support the bank’s merger with Auto Club Trust in April 2025. Their investment reflects confidence in Grasshopper’s ability to scale its digital banking platform and expand its suite of business and consumer financial products. Growth metrics as of June 30, 2025 showed a 53% increase in assets, an 81% surge in deposits, and a 49% rise in loans, all backed by this strategic capital infusion. - learn more
    • Mucker Capital participated in beatBread’s $124M capital raise, alongside Citi’s SPRINT team, Deciens Capital, and Advantage Capital. Their involvement supports beatBread’s strategy to expand sales, marketing, and technology operations, while enabling greater funding flexibility for independent artists, songwriters, and labels through its AI-powered platform. - learn more
    • B Capital co-led Positive Development’s $51.5M Series C funding round alongside aMoon and Flare Capital Partners, helping to fuel expansion of its developmental therapy model for autistic children. Their involvement underscores confidence in the company’s family-centered, play-based approach—which lowers costs by about 50% compared to traditional ABA therapy—and supports growth through new Medicaid partnerships and technology enhancements. - learn more
    • Clocktower Ventures participated in Creditop’s latest $3.7M funding round, which was led by Collide Capital and also included Alaya Capital, Amador Holdings, Newtopia, and Driven VC. Their involvement supports Creditop’s mission to enable credit access at the point of sale, without a credit card, and will help fintech deepen its footprint in Colombia while exploring expansion across Central America and Peru. - learn more
    • Thiel Capital participated in Pilgrim’s $4.3 million seed funding round, backing the biotech startup founded by 21-year-old Jake Adler after he demonstrated its hemostatic dressing, Kingsfoil, on himself. Their support underscores confidence in Pilgrim’s aggressive R&D and dual-use medical platform targeting both military and civilian emergency care. - learn more
    LA Exits
    • ElectroMagnetic Systems, Inc., a California-based specialist in AI and machine learning-powered target recognition software for space-based radar, has been acquired by Voyager. The deal strengthens Voyager’s AI-native surveillance and intelligence capabilities, enabling real-time monitoring across ground, air, and space domains to meet evolving defense and commercial demands. - learn more
    • Daring Foods is being acquired by Australia’s leading plant-based meat company, v2food, in a move that strengthens v2food’s push into the U.S. market. Daring will continue operating under its own brand and will serve as a platform to introduce v2food’s own products across the States. The deal, paired with a strategic partnership with Japanese food giant Ajinomoto, aims to accelerate innovation in clean-label protein and expand global reach. - learn more
    • Irwin Naturals is being acquired by FitLife Brands in an all-cash transaction valued at $42.5M, which includes approximately $16M in net working capital. The deal, expected to close around August 8, 2025, will nearly double FitLife’s scale, with projected combined annual revenue of over $120M and adjusted EBITDA between $20–25M. It will be funded with cash on hand, a new term loan, and a revolving credit facility, and is expected to generate synergies through complementary product lines, broader mass-market distribution, and improved operational efficiencies. - learn more
    • Solsniper, a Solana-focused trading and analytics platform known for high-speed memecoin execution, has been acquired by Phantom as part of its strategy to expand beyond wallets into full-service on-chain finance. The Solsniper team will join Phantom to enhance its advanced trading features, while the platform will continue operating independently. The move underscores Phantom’s ambition to offer seamless, integrated trading tools within the Solana ecosystem. - learn more
    • Cinelease is being acquired by Zello, a private investment platform dedicated to scaling businesses across the entertainment industry, in a strategic move to bolster production infrastructure and amplify its presence across North America. Under Zello’s ownership, Cinelease will continue operating as a standalone company led by its veteran team, enhancing its lighting, grip, and studio offerings for film, TV, and commercial productions. This acquisition sets the stage for disciplined growth and stronger relationships within the film and television production ecosystem. - learn more

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            Smart Shoes for Kids? Skechers Thinks So 👟

            🔦 Spotlight

            Happy Friday, LA!

            This week, Skechers may have just kicked off a new trend that’s bound to have parents and tech lovers talking. They've unveiled the "Find My Skechers" line, kids’ sneakers that come with a hidden compartment to securely hold an Apple AirTag. For $52 to $58, parents can now track their child’s shoes in real-time using the Find My app, giving a whole new meaning to "keeping an eye on things." While these tech-savvy kicks are already gaining attention, will they become the new norm in kids' footwear? And who’s next? Will Nike or Adidas be jumping on the AirTag bandwagon, or is Skechers setting the stage for a whole new wave of tech-integrated fashion?

            But it’s not all smooth sailing. This innovation raises some interesting questions about privacy and surveillance. Are we crossing a line when we start tracking our kids’ every move through their shoes? While Apple’s anti-stalking features are in place to prevent misuse, it will be intriguing to see how other brands and parents respond to this new blend of fashion and tech.

            What do you think? Could this become a must-have feature in the next generation of kids' gear, or is it a step too far? Let us know your thoughts!

            🤝 Venture Deals

            LA Companies

            • LakeFS, a provider of Git-like version control for data lakes, has secured $20M in a growth funding round led by Maor Investments. The funds will support the company's expansion efforts and product development aimed at enhancing data engineering and AI initiatives within enterprise and public sector environments. - learn more

            LA Venture Funds

              • Sound Ventures co-led the $16.1M Series A funding round for Knit, an AI-powered consumer research platform. The funds will be used to accelerate product development, enhance AI capabilities, and expand global research operations. This investment underscores the growing trend of combining AI with human expertise to deliver faster, cost-effective, and high-quality insights for enterprise research. - learn more
              • Anthos Capital co-led a $60M Series A funding round for Good Job Games, a mobile game developer known for creating casual and hyper-casual games. The investment, co-led by Menlo Ventures, will support the company's growth, enabling the expansion of its game portfolio and enhancing user engagement through innovative gameplay features. This funding marks a significant step in scaling Good Job Games’ operations and solidifying its position in the competitive mobile gaming market. - learn more
              • Pinegrove Capital Partners participated in Ramp's $500M Series E-2 funding round, which values the company at $22.5 billion. The funds will be used to accelerate Ramp's AI-driven financial tools, aiming to enhance automation and efficiency in corporate finance operations. - learn more
              • Riot Ventures participated in Oxide Computer Company's $100M Series B funding round, led by the U.S. Innovative Technology Fund (USIT). This investment will enable Oxide to scale its manufacturing capabilities, enhance customer support, and accelerate product delivery to meet the growing demand for on-premises cloud computing solutions. - learn more
              • Rebel Fund participated in a $3.2M seed funding round for Caseflood.ai, a San Francisco-based legal tech startup offering AI-powered client intake solutions for law firms. The funds will support the development of Caseflood's advanced voice agent, Luna, which autonomously handles client interactions, including consultations and retainer signings, aiming to enhance conversion rates and operational efficiency for law firms. - learn more
              • Smash Capital participated in Ambience Healthcare's $243M Series C funding round, co-led by Oak HC/FT and Andreessen Horowitz (a16z). The investment will support Ambience's expansion of its ambient AI platform, which automates clinical documentation, coding, and workflow tasks across over 200 specialties. The platform integrates directly with electronic health records, enhancing efficiency and compliance in healthcare settings. - learn more
              • ARTBIO, a clinical-stage radiopharmaceutical company developing alpha radioligand therapies for cancer treatment, has secured $132M in a Series B funding round. The round was co-led by Sofinnova Investments and B Capital, with participation from Alexandria Venture Investments and other investors. The funds will support the advancement of ARTBIO's lead program, AB001, through Phase II clinical trials, and facilitate the expansion of its manufacturing and supply chain infrastructure. - learn more
              • Rebel Fund participated in OffDeal's $12M Series A funding round, led by Radical Ventures, to support the company's mission of building the world's first AI-native investment bank. OffDeal aims to democratize access to high-quality M&A advisory services for small and mid-sized businesses by automating analyst tasks with AI, enabling efficient sell-side transactions. The funds will help scale OffDeal's technology-driven, advisor-led approach to facilitate successful exits for entrepreneurs. - learn more
              • Sandbox Studios participated in a $3M seed funding round for Sarelly Sarelly, a Mexican cosmetics brand, with backing from U.S. investors like Wollef, Morgan Creek Capital Management, and Hyve Ventures. The funds will support Sarelly Sarelly's expansion into the U.S. market, including retail launches at Ulta Beauty and growth on digital platforms like TikTok Shop. - learn more

              LA Exits
              • NEOGOV, an El Segundo-based provider of HR and compliance software for U.S. public sector agencies, has been acquired by EQT and CPP Investments in a deal valued at over $3 billion. The acquisition will help NEOGOV expand its product offerings and grow its presence across North America. - learn more

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                    From Retro Cool to AI Convenience: LA’s New Tech Normal

                    🔦 Spotlight

                    Hello LA,

                    What do you get when you cross a 1950s diner, robot-powered retail, and apps trying to do the right thing? A very Hollywood week in LA tech.

                    Image Source: Tesla

                    Let’s start with the most literal: Tesla’s long-awaited retro-futuristic diner just opened on Sunset, complete with drive-in movie screens, EV charging bays, and a neon glow that practically begs to be Instagrammed. It’s a mashup of Elon-style nostalgia and innovation, where your burger might take longer to arrive than your Model 3 finishes charging. While the menu sticks to diner classics (yes, there's a milkshake bar), the real flex is how Tesla is rebranding waiting as an “experience.” In a city where parking is currency, Tesla has turned it into a destination.

                    Image Source: VenHub

                    Just down the street, VenHub’s smart convenience store quietly opened its doors, but this is no 7-Eleven. The Pasadena-based startup is betting on AI-powered, cashier-free retail hubs that can be dropped anywhere, anytime. Think vending machine meets Apple Store. Investors are buying in on the promise of 24/7 access to snacks, essentials, and even meds. No human required. In a city of hustle, VenHub wants to make “convenient” even more convenient. Check out their locations here.

                    Uber also rolled out new "Women Rider Preferences" in LA, letting women and nonbinary drivers opt to pick up women riders. It's a long-requested feature aimed at improving safety and comfort, especially for those driving at night. And while it’s opt-in for now, it’s a significant move toward rethinking trust and transparency in ride-hailing, starting with the people behind the wheel.

                    Image Source: Snap

                    And finally, Snap launched "Home Safe Alerts" to quietly keep you safer on the move. You can now send automatic updates to trusted friends when you're heading out or getting home. It’s a subtle yet powerful shift toward making tech feel more protective and less performative. Snap’s way of saying, "Text me when you get home," but without the follow-up guilt.

                    So whether you're grabbing a burger under the glow of a Tesla screen, scanning a QR code at a robot-run bodega, or just getting home a little safer, this week reminded us that LA doesn’t just build the future. It makes it weird, wonderful, and just a little more user-friendly.

                    Catch you next week ✌️

                    🤝 Venture Deals

                    LA Companies

                    • Nevoya has raised $9.3M in seed funding, led by Lowercarbon Capital, to transform the American trucking industry with its advanced freight platform. The company aims to modernize logistics by optimizing routes, improving efficiency, and better connecting shippers and carriers. The funding will help Nevoya expand its technology and scale operations to redefine how goods move across the country. - learn more

                    LA Venture Funds

                    • Pinegrove Capital Partners joined Armada’s $131M Series B round to support the San Francisco-based edge computing startup in its mission to bring secure, modular data centers to remote and infrastructure-poor environments. Armada builds rugged, containerized units like its flagship Galleon and newly unveiled Leviathan, designed to enable real-time AI and compute at the edge. The funding will accelerate the deployment of these solutions globally and scale development for critical defense, energy, and industrial use cases. - learn more
                    • Rebel Fund joined Lyra’s $6M seed round, supporting the San Francisco startup that’s redefining video conferencing with its AI-native platform. Lyra transforms traditional meetings into interactive workspaces with real-time collaboration and auto-generated summary notes. The capital will bolster infrastructure and support rapid growth as the company scales its go-to-market operations. - learn more
                    • Plassa Capital participated in Bloom’s $1.6M pre-seed round to support the startup’s mission of building an all-in-one hub for the crypto trading community. Based in Miami, Bloom offers a social platform that combines trading tools, real-time news, and community-driven insights for crypto traders. The funding will help the company grow its team, enhance its product, and expand its user base. - learn more
                    • Embark Ventures participated in TRIC Robotics’ seed funding round to support its development of autonomous robots that help farmers manage pests and plant diseases without chemicals. Based in Delaware, TRIC uses ultraviolet light and computer vision to treat crops like strawberries in a sustainable, labor-efficient way. The funding will help the company expand deployments, grow its team, and scale its technology to more farms across the U.S. - learn more
                    • Alexandria Venture Investments participated in Dispatch Bio’s $11.2M seed funding round. Based in San Diego, Dispatch Bio is developing a novel immunotherapy platform that aims to deliver a universal treatment for solid tumors by reprogramming immune cells at the tumor site. The funds will support further development of its platform and expansion of preclinical studies. - learn more
                    • Mucker Capital led Vaudit’s $7.3M seed round, reinforcing its belief in the San Francisco Bay Area-based startup. Vaudit delivers an AI-powered media audit platform that automates real-time validation of ad spend, detecting discrepancies before payments are processed. The funding will enable Vaudit to enhance its platform, expand its team, and scale its global reach across web and mobile channels. - learn more
                    • Morpheus Ventures participated in xLight’s $40M Series B funding round to support its mission of transforming semiconductor manufacturing. The Palo Alto-based company develops advanced laser-based lithography technology designed to make chip production faster, more precise, and more cost-effective. The new funding will be used to accelerate product development, expand the team, and scale operations to meet growing demand. - learn more
                    • Magnify Ventures participated in Alix’s $20M Series A funding round to help the company modernize the estate settlement process. Based in New York, Alix offers a digital platform that simplifies and streamlines estate administration for families and professionals. The funds will be used to enhance the platform, grow the team, and expand its reach to meet increasing demand. - learn more
                    • Untapped Ventures participated in Nexxa AI’s $4.4M seed round to support the company’s mission of bringing specialized AI solutions to heavy industries like manufacturing, logistics, and energy. Based in Sunnyvale, Nexxa’s platform enables domain-specific AI deployment tailored to industrial operations. The funding will help the company expand its engineering team, accelerate product development, and onboard new enterprise customers. - learn more

                    LA Exits
                    • Exverus Media, a Los Angeles-based media agency known for its data-driven approach to brand growth, has been acquired by global marketing firm Brainlabs. The acquisition strengthens Brainlabs’ U.S. presence and adds strategic media planning and measurement capabilities to its portfolio. Exverus will continue operating under its brand while gaining access to Brainlabs’ global resources and infrastructure. - learn more
                    • Generous Brands is set to acquire Health-Ade Kombucha, the Los Angeles-based beverage company known for its premium, gut-healthy drinks. The deal marks Generous Brands’ push into the fast-growing functional beverage market and adds a high-profile name to its portfolio. Health-Ade will continue operating with its existing team while benefiting from expanded resources and distribution capabilities. - learn more
                    • Launch Potato has acquired OnlyInYourState, a travel discovery platform known for spotlighting hidden gems across the U.S. The acquisition expands Launch Potato’s portfolio of digital brands and supports its goal of using AI to personalize trip planning experiences. OnlyInYourState will continue to operate while integrating with Launch Potato’s performance marketing and content strategy capabilities. -learn more
                    • Vilore Foods has acquired Tia Lupita Foods, a better-for-you Mexican food brand known for its hot sauces, chips, and tortillas made with simple, sustainable ingredients. The acquisition expands Vilore’s portfolio into the health-conscious and culturally authentic food space. Tia Lupita will continue to operate under its brand while gaining access to Vilore’s distribution network and resources. - learn more

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