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.

https://twitter.com/spencerrascoff
https://www.linkedin.com/in/spencerrascoff/
admin@dot.la
$160M Tugboats and Undersea Drones: LA Startups Are Raising the Stakes

🔦 Spotlight

Happy Friday LA,

This week’s headlines take us from the ocean floor to the docks of Long Beach, with LA companies leading the charge.

Image Source: Anduril

Let’s start with Anduril Industries, which rolled out three major announcements that underline just how quickly it is expanding its footprint across defense tech. The biggest milestone came from Ghost Shark, an extra large undersea drone developed in partnership with the Australian Navy. After just three years, it has moved from prototype to an official program of record, an unusually fast turnaround in an industry where procurement often takes decades. It marks a significant step for autonomous systems under the sea, an area where defense agencies have long struggled to innovate.

Image Source: Anduril

The company also revealed Menace I, a ruggedized system designed to bring petabyte scale processing power directly to the battlefield. Think of it as cloud computing without the cloud, giving troops the ability to process massive amounts of sensor data and video on site rather than relying on faraway servers. And finally, Anduril landed a contract to create mixed reality training tools, using immersive simulations to prepare service members for missions more effectively. Training has always been one of the costliest and most logistically challenging aspects of defense, and bringing advanced MR into the mix could transform how quickly and safely soldiers can get mission ready. Together, these updates show an LA company moving fast across land, sea and even into the training ground.

Image Source: Arc

Meanwhile, Arc is proving that electrification is not just for cars and yachts, it is now heading into some of the hardest working vessels on the water. The Venice based startup announced a $160 million deal with Long Beach’s Curtin Maritime to deliver eight hybrid electric tugboats. Tugboats are the muscle of the harbor, guiding massive cargo ships in and out of ports, and they usually burn through enormous amounts of diesel. Arc’s push into this space signals more than just a big contract. It is a pivot from building high performance electric speedboats for early adopters to tackling one of the most carbon heavy corners of maritime work.

The scale of this deal shows how far Arc has come since launching just a few years ago. Building hybrid electric tugboats is not a side project, it is a sign that the company wants to play a role in reshaping the future of port operations. And if LA’s own clean tech boat builder can make a dent in one of the dirtiest industries on the water, the ripple effects could stretch far beyond the coastline.

🤝 Venture Deals

      LA Companies

      • Apex Space closed a $200M Series D round led by Interlagos, with participation from existing investors including Andreessen Horowitz, Point72 Ventures and 8VC, pushing its valuation past $1 billion. The Los Angeles based company builds satellite buses, the standardized spacecraft platforms that carry and power payloads ranging from Earth imaging sensors to missile early warning systems. With the new funding, Apex plans to increase production capacity by 50 percent and more than double its manufacturing facility as demand for space defense systems continues to grow. - learn more
      • Sapphire Technologies has raised an $18M Series C round, including investment from Mitsubishi Heavy Industries along with existing backers such as Equinor Ventures, Cooper and Company and Energy Capital Ventures. The funds will be used to scale up production at Sapphire’s manufacturing facility in Cypress, California, expand global deployments of its FreeSpin In-line Turboexpanders in regions like Japan and enter new markets. Sapphire’s technology converts otherwise wasted pressure energy, often from natural gas, into clean and emissions free electricity, playing a growing role in the global energy transition. - learn more
      • LocalExpress has raised $6.2M in a venture round led by OXZ Capital to expand its AI data capabilities into the grocery industry. The Glendale based platform, already serving independent grocery and food retailers across the US, Canada and Latin America, is transitioning from supporting internal operations to becoming a premier data syndication hub in the sector. This round will fuel further development of its unified commerce solutions and help scale its AI-powered systems for harmonizing transaction and inventory data. - learn more
      • ProRata.AI closed a $40M Series B financing round led by Touring Capital with participation from Bold Capital Partners and others, to launch Gist Answers, a new AI-as-a-service tool for publishers. Gist Answers lets publishers embed custom AI search, summarization, and recommendation features directly on their sites while maintaining control over their content. The move is designed to help publishers increase engagement, protect their content, and unlock new revenue streams in the AI era. - learn more

      LA Venture Funds

      • Upfront Ventures joined a group of investors in backing Sophont’s $9.22M seed round, led by Kindred Ventures. Sophont is building multimodal medical foundation models that combine data from pathology slides, brain scans, clinical notes, and lab results to enable functionalities like symptom triage, biomarker discovery, and clinical trial cohort selection. The funding will go toward increasing compute capacity, expanding data partnerships, and recruiting researchers to accelerate the development and release of model backbones and open science infrastructure. - learn more
      • Presight Capital participated in the $24M Series A round raised by TERN Group, which was led by Notion Capital. The funding will help TERN scale its AI powered infrastructure for global healthcare worker recruitment, credentialing and mobility, especially helping caregivers and nurses in places like India gain access to international job opportunities. TERN plans to use the investment to expand into new geographies, deepen training programs, and further build tools that make migration, compliance and placement faster, fairer and more transparent. - learn more
      • Emmeline Ventures joined a strong syndicate in Lōvu Health’s $8M Series A round, led by SJF Ventures. The funding will support Lōvu in scaling its AI-powered maternal health platform, enhancing remote monitoring, curated specialist services, and ongoing care from pre-conception through the first two years postpartum. With this investment, Lōvu aims to close gaps in maternal healthcare access and outcomes, especially for underserved populations. - learn more
      • Integrity Growth Partners led a $28M Series A round in Pest Share, joined by existing investors including MetaProp, Capital Eleven and RE Angels. Pest Share is an on-demand pest control platform tailored for residential property managers, operating in all 48 states and serving 300,000 residential units. The capital will fuel expansion in single-family and multifamily rental markets, enhance product innovation, and deepen integrations with property management systems. - learn more
      • Mantis VC joined Forerunner Ventures, Neo, Abstract and several angel investors in backing Hero Assistant’s $3.5M seed round at a $30M valuation. Hero Assistant is building a “Daily Assistant” super-app that consolidates things like calendars, weather, tasks, habits, goals, grocery ordering, notes and news, already replacing up to eight separate apps for its more than 300,000 users. The funds will help the company enhance features, scale growth, and deepen its reach in productivity. - learn more
      • Wedbush Healthcare Partners took part in Odyssey Therapeutics’ oversubscribed $213M Series D financing round alongside both new and existing investors. The funding will be used to push forward Odyssey’s pipeline of clinical and preclinical therapies focused on treating complex autoimmune diseases. With this capital raise, Odyssey aims to make progress toward key clinical milestones and bring precision immunomodulation treatments closer to patients in need. - learn more
      • BroadLight Capital participated in Higgsfield’s $50M Series A round, which was led by GFT Ventures and also backed by firms like Menlo Ventures and NextEquity Partners. Higgsfield is pushing its “click-to-video” AI platform, which lets users turn curated presets into cinematic clips with a single click rather than wrestling with complex prompts. In only five months since launch, the company has already drawn over 11 million users and more than 1.2 billion social media impressions, signaling strong momentum in the creator video space. - learn more
      • Impatient VC participated in Sphinx’s $9.5M Seed round, which was led by Lightspeed and also included investors like Bessemer Venture Partners, Box Group, and K5. Sphinx is launching an AI copilot built especially for data scientists, one that thinks in statistics and patterns to turn raw data into actionable insights without skipping rigor. The funds will go toward refining tools that integrate into workflows like Jupyter notebooks and VSCode so data teams can explore, model, and make decisions faster. - learn more
      • WME Group led a $20M Series B round in Palm Tree Crew, valuing the company at $215 million. The funding will power expansion across its hospitality venues, live events, and lifestyle ventures while leaning into WME’s entertainment, licensing, and brand network. Palm Tree Crew plans to scale its properties, deepen its festival footprint globally, and continue growing its portfolio of consumer brands as part of the next chapter. - learn more
      • Blue Bear Capital participated in Nuclearn’s $10.5M Series A round that helps the company deepen its AI-capabilities for nuclear operations. Nuclearn, founded by engineers who've worked inside power plants, builds specialized tools like CAP AI to automate safety-critical, documentation-heavy tasks and ensure regulatory compliance. The funding will support product expansion, talent hiring, and scaling its platform to more reactors worldwide. - learn more
      • Amplify was one of the investors joining Endurance28 and others in Cascade Bio’s $6M raise, which includes $2.8M in equity and $3.2M in nondilutive funding. Cascade Bio is advancing its enzyme-immobilization technology to help industrial partners transition from petrochemical processes to greener, biomanufacturing workflows. The funding will enable Cascade to scale its high-stability biocatalysts for use across chemicals, food ingredients, fragrances, and pharmaceuticals. - learn more

      LA Exits

      • Northstar has been acquired by Nayya, combining Northstar’s financial wellness tools with Nayya’s health, compensation and actuarial data platform. The unified offering introduces a “SuperAgent,” an AI adviser that not only helps employees understand benefits but, with their permission, can take actions like auto enrolling in wellness programs or appealing denied claims. The goal is to make health and wealth benefits simpler, more transparent and more useful year round rather than just during open enrollment. - learn more
      • Integrated Rental Systems has been acquired by VitalEdge Technologies, a major provider of dealer management software for heavy equipment. Integrated Rental’s platform is considered one of the most advanced in its field, and this deal allows VitalEdge to offer more fully integrated solutions covering rental, parts, and service revenue streams for equipment dealers. Alise Moncure, CEO of Integrated Rental, will join VitalEdge’s leadership team as President of Expansion Markets, leading rental and other high-growth segments. - learn more
      • VideoVerse has been acquired by Minute Media, bringing its AI-powered sports video platform Magnifi into the company’s portfolio. Magnifi helps leagues, teams and publishers automatically detect key moments, create instant highlights and distribute short-form video content more efficiently. With the acquisition, Minute Media is expanding beyond publishing to offer a more complete solution for video creation, distribution and monetization. - learn more
      • Bespoke Treatment has been acquired by Stella Mental Health, expanding the company’s services in Los Angeles. Known for its integrative approach, Bespoke offers treatments such as stellate ganglion block for trauma, IV ketamine, Spravato® and intensive outpatient programming. Through the acquisition, Stella is broadening its footprint and strengthening its ability to deliver personalized behavioral health care. - learn more

      Download the dot.LA App

      Snap’s AI, Paramount’s RTO, and NeueHouse’s Exit: LA’s Wild Week

      🔦 Spotlight

      Good Morning LA,

      If you blinked this week, you might’ve missed Snap unveiling new AI-powered Lenses, NeueHouse announcing its closure, and Paramount rolling out a five-day return to office mandate. Let’s get into it.

      First up: Snap. The company introduced its new “Imagine” Lenses powered by generative AI. Instead of the playful filters we all know, these tools feel closer to an on-demand art studio, letting people turn imagination into visuals instantly. It shows Snap leaning into what it does best: pushing the boundaries of how we express ourselves through the camera.

      Meanwhile, NeueHouse announced it will be closing. Known for blending hospitality, community and high-design workspaces, it attracted a mix of entertainment, design and tech professionals who wanted something beyond the typical co-working setup. Its exit comes as Paramount is moving in the opposite direction, requiring employees to return to the office full time starting in January. Together, these moves highlight the different paths workplaces are taking in a post-hybrid world, from phasing out to doubling down.

      On the global stage, the world’s eyes are on Berlin, where IFA 2025 is underway. The trade show is buzzing with foldable devices, wearables and AI-powered appliances that are blurring the line between tool and companion. The innovations debuting there are setting the tone for what consumers and startups everywhere will soon be building with, competing against and dreaming beyond. For those following along, The Verge is running live coverage with updates on the biggest reveals.

      And finally, OpenAI announced a new jobs platform, aimed at connecting workers with opportunities in an AI-driven economy. It is positioned as a way to broaden access and help talent navigate shifting industries. For engineers, creatives and founders alike, it is another signal that collaborating with AI is not a future skill, it is a present-day requirement.

      🤝 Venture Deals

          LA Venture Funds

          • FirstLook Partners participated in Hello Patient’s $22.5M Series A round, which backs the Austin based conversational AI platform transforming patient intake and communications. Hello Patient’s technology, handling voice, text, and chat conversations, helps healthcare providers streamline appointments, reduce missed calls, and improve patient access. The fresh funding will accelerate enhancements to its AI driven platform and support expansion to healthcare organizations nationwide. - learn more
          • Hyperlink Ventures joined Mojo Vision’s $75M Series B Prime funding round to support the expansion of its high performance micro LED platform. Mojo Vision plans to leverage the investment to accelerate commercialization of its wafers in, wafers out micro LED technology, which merges advanced silicon architecture, GaN on silicon emitters, quantum dots, and micro lens arrays to power next generation AI devices and infrastructure. - learn more
          • Fika Ventures joined Dispatch’s $18M Series A round, helping to bring its total funding to $30M. Dispatch provides AI powered, automated data orchestration for wealth management firms, eliminating repetitive tasks, streamlining client onboarding, and ensuring real time, connected client data. The new capital will fuel the expansion of its agentic workflows and further development of its AI ready infrastructure for advisors. - learn more
          • TenOneTen Ventures participated in Elysian’s $6M seed round to support the company’s AI native third party administration platform for commercial insurance claims. Elysian’s technology automates the complex, document heavy middle of claim handling by surfacing coverage insights and drafting communications so adjusters can focus on making strategic decisions. The funding will help accelerate go to market efforts, enhance customer onboarding, and scale both delivery operations and the underlying AI platform. - learn more
          • M13 participated in Allocate’s $30.5M Series B round, backing the company’s platform that helps wealth advisors and family offices access and manage private market investments. The new funding will support expansion of its AI-powered infrastructure and workflow automation, as well as broaden its reach beyond venture capital into private equity and credit. - learn more
          • Walkabout Ventures took the lead in Advisor.com’s $9M seed round. Advisor.com operates an AI-powered platform that pairs investors, especially those with under $500,000 in investable assets, with vetted fiduciary financial advisors. The funds will be used to accelerate customer acquisition, enhance its advisor matching technology, and expand its network of top-tier advisors. - learn more
          • Ares Management participated in ID.me’s latest funding, where the company raised a total of $340M in a Series E round combined with a credit facility, pushing its valuation above $2 billion. ID.me, a digital identity wallet trusted by more than 152 million users, will use the capital to scale access to secure, reusable digital identities and bolster its defenses against increasingly AI-driven fraud. - learn more
          • Core Innovation Capital participated in Flex’s $15M Series A funding round. Flex is a payments infrastructure platform that enables health and wellness retailers to accept Health Savings Account (HSA) and Flexible Spending Account (FSA) funds at checkout. With this investment, Flex plans to scale its enterprise reach, enhance its core technology, and grow its team to help merchants tap into more than $150 billion in underutilized pre‑tax health spending. - learn more
          • F4 Fund joined Camera Intelligence’s $2M seed funding round. The company is developing an AI-powered camera system that embeds a large language model (LLM) directly into a Micro Four Thirds mirrorless camera, simplifying content creation through voice-activated controls and in-camera editing. The new capital will accelerate the build-out of this integrated AI-native camera and content editing solution, with an LLM feature set to launch on iOS in fall 2025. - learn more

          LA Exits

          • Air Lease Corporation has entered into a merger agreement to be acquired by a consortium including Sumitomo Corporation, SMBC Aviation Capital, Apollo-managed funds, and Brookfield in an all cash deal expected to close in the first half of 2026. Shareholders will receive $65 per share, valuing the company at about $7.4 billion or $28.2 billion including debt, and the company will be rebranded as Sumisho Air Lease with SMBC set to manage its fleet and order book. - learn more

          Download the dot.LA App

          LA Startup Powering Immigrant Workforce Secures $7.5M

          🔦 Spotlight

          Happy Friday, Los Angeles,

          It’s Labor Day weekend, which means most of us are thinking about a little time off. But one LA startup is laser focused on work, specifically on the millions of immigrant workers who keep the U.S. economy running.

          This week, Welcome Tech raised $7.5 million to expand its AI powered platform that connects immigrant communities with U.S. employers. If you’re not familiar, Welcome Tech has quietly become one of the most important bridges between immigrant workers and the American labor market. The company offers a suite of services, from job matching and financial tools to healthcare and education, built specifically for immigrant families navigating systems that weren’t designed with them in mind.

          The scale is staggering. Welcome Tech already supports more than 4.5 million registered members, and its enterprise partnerships have tripled in the last year. Revenue is up more than 200 percent year over year. With this new funding, the company plans to double down on AI, personalizing onboarding, automating job matching, and expanding multilingual support so workers can find opportunities faster and employers can access a motivated workforce with fewer barriers.

          Welcome Tech’s growth also underscores something very LA: this city runs on immigrant talent, and the systems that support them often lag behind. By building infrastructure tailored to this workforce, Welcome Tech isn’t just scaling a business, it’s tackling a gap that traditional employers and institutions have ignored for decades.

          As Labor Day weekend rolls in, it’s a reminder that the real labor story isn’t just about time off, it’s about how companies like Welcome Tech are reshaping access to opportunity in one of the country’s most essential workforces.

          And with that, let’s get into this week’s venture deals across LA.

          🤝 Venture Deals

          LA Companies

          • Payment Labs, a Los Angeles based fintech specializing in seamless payment workflows for industries like sports, esports, and the creator economy, has closed an oversubscribed $3.25M seed funding round led by Aperture Venture Capital. The company’s API powered SaaS platform, already trusted by Microsoft, SEGA, X Games, and more, simplifies complex global pay ins and payouts across 150+ currencies and 180+ countries while integrating tax compliance, royalty distributions, and reporting. This new capital will accelerate expansion of tailored payment solutions and bolster operations to support high growth verticals. - learn more

            LA Venture Funds

            • Clocktower Technology Ventures, participated in Momento Seguros’ $10.25M Series A round. The Mexico City based digital auto insurer is leveraging the capital to expand its full-stack platform, offering flexible, mobile-first coverage tailored to underserved drivers. By modernizing payments, underwriting, and claims processing, Momento aims to disrupt a traditionally rigid insurance market with transparent, user-centric solutions. - learn more
            • Dangerous Ventures participated in Copper’s $28M funding round aimed at scaling the world’s first battery equipped induction range. The Berkeley based company builds plug and play induction stoves with built in batteries that run on standard 120 volt outlets, simplifying electrification of cooking while offering backup power during outages. Copper plans to use the new funds to expand production, develop new appliances, and leverage its grid friendly design, already under contract to deliver 10,000 units to public housing, to drive broader adoption of clean, efficient cooking solutions. - learn more
            • Alexandria Venture Investments participated in Leal Therapeutics’ $30M Series A round, joining a syndicate that includes SV Health Investors’ Dementia Discovery Fund, OrbiMed, Newpath Partners, Chugai Venture Fund, Euclidean Capital, and PhiFund. Leal is advancing its neuro metabolic pipeline with lead programs LTX 001 moving into clinical trials for schizophrenia and LTX 002 progressing toward initial clinical data in ALS. This funding will also support the advancement of additional pipeline candidates and technologies aimed at delivering transformative treatments for CNS disorders. - learn more
            • Impatient Ventures and Riot Ventures participated in Blue Water Autonomy’s $50M Series A funding round to accelerate development of autonomous, long range ships designed for the U.S. Navy. The capital will be used to build and deploy the firm's first full sized autonomous ship by next year and support rapid scaling, as the team has already quadrupled since its seed round while completing engineering tests and securing materials from over 50 suppliers. This funding brings the company’s total raised to $64 million and underscores growing momentum around U.S. maritime innovation. - learn more
            • TenOneTen Ventures joined a $3.5M seed round in Loman AI, supporting the Austin based startup’s efforts to transform restaurant operations using voice AI. Loman’s AI phone agent handles call volume by taking orders, booking reservations, answering FAQs, and integrating smoothly with POS systems, helping restaurants boost revenue by up to 22% while cutting labor costs by as much as 17%. This new funding will accelerate product development and team expansion as demand for Loman’s platform grows nationwide. - learn more
            • CIV participated in AiGent’s $6M seed round, backing the AI driven startup’s mission to transform idle backup generators into a powerful decentralized grid resource. AiGent’s platform aggregates and orchestrates distributed generation assets including those at commercial, industrial, and mission critical facilities like AI data centers, turning them into rapidly dispatchable “distributed power plants.” This innovative approach not only enhances grid reliability and reduces costs but also opens up new revenue streams for asset owners without the time, cost, or disruption of building additional infrastructure. - learn more
            • Blue Bear Capital led a $12.4M SAFE funding round in Splight, supporting the San Francisco-based grid technology company’s mission to dramatically expand transmission capacity using machine-learning. The new capital will fuel deployment of Splight’s flagship Dynamic Congestion Management™ across U.S. and European grids—helping alleviate long interconnection delays and renewables curtailment by intelligently leveraging existing infrastructure. This round also secures Splight’s ability to scale both its commercial and technical teams amid surging demand from AI data centers and utilities. - learn more
            • Amboy Street Ventures participated in Nest Health’s $12.5M Series A round to support the expansion of its whole family, in home care model for Medicaid populations. Nest Health leverages AI powered clinical services, from medical to behavioral and social support, to deliver care at home while cutting churn and improving outcomes, including reduced ER visits and higher vaccination rates. The company will use the funding to scale its AI enabled care offerings into new regions and enhance partnerships with payors. - learn more
            • VamosVentures participated in Kira’s $6.7M seed funding round, supporting the AI driven fintech infrastructure platform as it emerges from stealth. The capital will enable Kira to expand across Latin America, especially South America, scale its technical team, and accelerate development of new embedded financial products powered by stablecoins, AI agents, and enterprise grade APIs. Kira aims to streamline financial services in markets with large underbanked populations and has already generated $3 million in revenue in its first year. - learn more

                        Download the dot.LA App

                        RELATEDEDITOR'S PICKS
                        Trending