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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From Metro Rails to Blended Wings: LA’s Transportation Era

🔦 Spotlight

Hello Los Angeles,

Move over Coachella, hello Stagecoach. With crowds headed east, LA might feel a little quieter this weekend, but beneath the surface, the city is busy making moves that could shape the future of travel.

Image Source: Metro

First up: a major milestone at LAX.

This June, the new LAX/Metro Transit Center Station will officially open, finally linking Metro's C and K Lines to a new ground hub near the airport.

It marks the first real rail connection to LAX in the airport’s history, a major step for a city that has long been synonymous with gridlock.

While the fully Automated People Mover system connecting the station to the terminals is still under construction and expected to open in 2026, the launch of the transit center is a critical piece of LA’s broader infrastructure upgrade ahead of the 2028 Olympics.

Even if most travelers will still rely on cars or rideshares for now, it is a sign that even the most car-centric corners of the city are starting to shift.

Image Source: JetZero

Meanwhile, in Long Beach, a local aerospace startup is aiming to transform air travel altogether and just got a major boost.

JetZero, a stealthy aviation company based in Long Beach, announced a new investment from United Airlines to advance its radical new aircraft design: the blended wing body.

Unlike traditional tube-and-wing planes, JetZero’s blended design integrates the wings and fuselage into a single structure, reducing aerodynamic drag and dramatically improving fuel efficiency.

United's investment is more than just financial support. It is a strategic bet on JetZero’s vision for cutting long-haul flight emissions in half, a critical goal as the aviation industry faces mounting pressure to decarbonize.

JetZero plans to have its first full-scale prototype flying by 2027, and if successful, it could set a new blueprint for the next generation of commercial aircraft.

For Los Angeles, it is another reminder that some of the boldest ideas shaping the future of mobility are being built right here in our own backyard.

Planes, trains, and a city learning to move a little differently. Just another week in LA.

🤝 Venture Deals

LA Companies

  • Durin, an El-Segundo startup aiming to automate drilling for critical minerals exploration, has secured $3.4M in a pre-seed funding round led by 8090 Industries. The company is developing a sensor-equipped drilling rig capable of drilling 300 meters deep, gathering data to build an automation model. The funding will support the development of this technology, with the goal of enabling unattended drill rigs within two to three years. - learn more
  • Altruist, a Los Angeles-based custodian and software platform for registered investment advisors (RIAs), raised $152M in a Series F round led by GIC, bringing its valuation to $1.9 billion. The platform streamlines account opening, trading, reporting, and billing for over 4,700 advisors. The new funding will be used to accelerate product development, expand the team, and scale enterprise capabilities. - learn more
  • Sesh, a superfan engagement platform that connects artists with fans through interactive experiences, exclusive content, and live events, has raised $7M in funding led by Miura Global. The funds will be used to expand platform capabilities, onboard more artists, and enhance technology for deeper insights and engagement opportunities. - learn more
  • Khloud, a new consumer brand founded by Khloé Kardashian, has raised $12M in an oversubscribed funding round with participation from Jessica Bixby, Serena Ventures, William Morris Endeavor (WME), and Shrug Capital. The Los Angeles-based company is debuting with a protein-rich popcorn made from whole-grain corn and its proprietary “Khloud Dust” seasoning, delivering 7 grams of protein per serving. The funds will be used to expand into additional snack categories and scale retail distribution, beginning with a Target launch on April 29. - learn more

LA Venture Funds

  • Anthos Capital co-led a $20M funding round for Theo, a New York-based crypto trading infrastructure startup. Theo enables retail investors to access institutional-grade trading strategies—such as high-frequency arbitrage and cross-chain funding rate optimization—through strategy-specific vaults, eliminating the need for technical expertise. The platform operates on a custom validator network that facilitates real-time execution across centralized and decentralized exchanges, enforcing margin requirements and system-wide overcollateralization. The funds will be used to expand Theo's validator infrastructure, integrate with additional financial platforms, and grow its user base. - learn more
  • Pinegrove Capital Partners participated in a $70M Series B funding round for Nourish, a New York-based startup offering AI-powered, insurance-covered virtual nutrition counseling. Nourish connects patients with registered dietitians to manage chronic conditions like obesity and diabetes, boasting a network of over 3,000 dietitians across all 50 states. The funds will be used to expand its provider network, enhance AI tools, and deepen partnerships with healthcare organizations. - learn more
  • Mantis VC participated in Chainguard's $356M Series D funding round. Based in Kirkland, Washington, Chainguard secures software supply chains by offering tools like secure containers, virtual machines, and libraries for open-source development. The funding will be used to expand product offerings, grow the go-to-market team, and support its expanding customer base. - learn more
  • Clocktower Technology Ventures participated in a $30M Series C funding round for Steadily, a landlord insurance provider based in Austin, Texas, and Overland Park, Kansas. Steadily offers tailored insurance solutions for rental property owners, serving policyholders across all 50 U.S. states. The funds will be used to expand operations, enhance technology, and grow the team, aiming to streamline the insurance process for landlords. - learn more
  • Blue Bear Capital participated in Ocient's recent $42.1M Series B extension, bringing the Chicago-based data analytics company's total funding to $159.4M. Ocient specializes in high-performance, energy-efficient analytics solutions for large-scale, complex data and AI workloads, leveraging its proprietary Compute Adjacent Storage Architecture® and Megalane™ technology. The new capital will be used to advance the development and delivery of energy-efficient solutions for costly, complex, and operationally burdensome data and AI workloads. - learn more
  • Group11 participated in Healthee's $50M Series B funding round, supporting the New York-based company's mission to simplify health benefits through AI. Healthee offers an AI-powered platform that helps employees and employers navigate complex healthcare systems, enhancing user experience, reducing costs, and improving care outcomes. The funds will be used to expand Healthee's product suite, scale go-to-market operations, and accelerate the development of its AI-powered tools. - learn more
  • Sum Ventures participated in Irrigreen's $19M Series A funding round. Headquartered in Edina, Minnesota, with operations in San Francisco, Irrigreen develops robotic irrigation systems that utilize digital mapping and AI to optimize water usage for residential lawns. The funds will be used to advance product development, expand manufacturing in the U.S., and enhance the company's smart lawn care solutions. - learn more
  • Ventek Ventures participated in Recce's $4M funding round. Based in San Francisco, Recce offers data-native code review tools designed to enhance data validation in AI and software development workflows. The funds will be used to advance Recce's open-source toolkit and launch its collaborative SaaS platform, Recce Cloud, aiming to streamline data validation processes across the software lifecycle. - learn more
  • B Capital led an $87M Series C funding round for Omnidian, a Seattle-based provider of performance assurance services for residential and commercial solar and energy storage systems. Omnidian offers comprehensive protection and performance plans, ensuring optimal operation and maintenance of clean energy assets. The funds will be used to scale core operations, expand into high-potential markets like Australia and Europe, and explore new product lines such as electric vehicle (EV) charging infrastructure and commercial energy storage solutions. - learn more
  • Overture VC participated in PHNX Materials' $2.5M seed funding round. Based in the U.S., PHNX Materials has developed a process to purify coal fly ash by removing impurities like sulfur and carbon, making it suitable for use in concrete production. This approach not only repurposes industrial waste but also reduces the carbon footprint of concrete by replacing a portion of cement. The funds will be used to scale PHNX's purification technology and expand its operations to meet the growing demand for sustainable construction materials. - learn more

LA Exits

  • Maza, a fintech startup catering to Spanish-speaking consumers in the U.S., has been acquired by Flex for $40M. Originally focused on helping immigrants open bank accounts and obtain ITINs, Maza shifted its services toward small business owners, such as landscapers and construction subcontractors. This pivot aligned with Flex's mission to provide comprehensive financial tools for business owners. Post-acquisition, Maza will rebrand as Flex Consumer, with its founders assuming executive roles within the combined company. The merger aims to accelerate their shared roadmap in delivering integrated financial solutions. - learn more
  • Moondust Management, a talent agency known for representing creators in travel, lifestyle, wellness, and purpose-driven content, has been acquired by Fixated, a digital entertainment platform. This acquisition aims to enhance Fixated's capabilities in content creation and brand partnerships by integrating Moondust's expertise and creator network. - learn more
  • ClaimShark, a provider of payment integrity solutions, has been acquired by Lyric, a leader in healthcare payment accuracy and integrity solutions. ClaimShark's innovative tools, including the Virtuoso command center and Replay audit platform, will be integrated into Lyric's AI-driven Lyric42 platform. This acquisition aims to enhance payment accuracy, transparency, and efficiency across the healthcare ecosystem by streamlining and simplifying healthcare transactions to eliminate waste. - learn more

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This Week in LA: Robotaxis, Reels & a $100K Challenge

🔦 Spotlight

Happy Friday, LA,

It’s Coachella Weekend 2, which means fewer cars on the road, easier restaurant reservations, and just enough quiet to hear the next wave of innovation humming through the city. This week, we’re watching more driverless cars roll in, Instagram remix your Reels feed, and a $100K climate challenge call for startups. Let’s get into it.

🚕 Zoox Is Bringing Its Robotaxis to LA

Image Source: Zoox

Amazon-owned Zoox just announced that its futuristic, steering wheel–less robotaxis are heading to Los Angeles. The company has begun mapping the city as it gears up to launch a fully autonomous ride-hailing service. These aren’t retrofitted Teslas; they’re bidirectional vehicles built specifically for autonomy, with no front, no back, and no driver seat.

It’s Zoox’s first major push beyond Northern California and Las Vegas, and it's a signal that LA is being positioned as a proving ground for next-gen transportation. As the city preps for the 2028 Olympics, Zoox is hoping to help LA reimagine what mobility looks like without a human behind the wheel.

👀 More on that here:Zoox’s LA Expansion

💬 Instagram’s New “Blend” Feature

Image Source: Instagram

Instagram just announced “Blend,” a new feature that creates a private Reels feed curated for you and a friend based on your shared interests. It’s like a personalized explore page, but just for two. Think Spotify Blend, but with more memes and fewer breakup ballads.

It’s currently in testing, but if rolled out broadly, Blend could change how creators build community and how content spreads in smaller, more intimate algorithmic circles.

🔥 LACI Launches the LA Resilient Rebuilding Cup

100 days after the Palisades and Eaton fires swept through parts of LA, the Los Angeles Cleantech Incubator (LACI) is launching a new initiative: the LA Resilient Rebuilding Cup. It’s a pitch competition aimed at finding startup solutions to help LA rebuild stronger and greener.

Up to $100,000 in prizes and piloting funds are up for grabs. Finalists will pitch live on July 10 in Downtown LA, and selected winners will get the opportunity to bring their technologies to fire-affected communities. Focus areas include fire detection, renewable energy, air quality, mental health tools, resilient construction, and more.

Startups have until May 30 to apply.
📍 Apply here


🤝 Venture Deals

LA Companies

  • Parallel Systems, a Los Angeles-based company developing autonomous battery-electric railcars, has raised $38M in a Series B funding round led by Anthos Capital, with participation from Riot Ventures and others. The funding will support the commercialization of its technology, including the launch of its first commercial pilot in Georgia. This pilot, approved by the Federal Railroad Administration, will test self-propelled intermodal flatcars over a 160-mile stretch, aiming to offer a more efficient and sustainable alternative to short-haul trucking. Parallel Systems plans to use the funds to scale production of its Generation 3 vehicles and expand operations in the U.S. and Australia. - learn more

LA Venture Funds

  • Bonfire Ventures led a $7.5M seed funding round for 1Fort, a New York-based startup that automates commercial insurance workflows for brokers using AI. Village Global and others participated in the round. 1Fort's platform streamlines the insurance process by automating tasks such as application completion, quote retrieval, and policy binding, helping brokers secure better coverage for clients more efficiently. The funds will be used to enhance the platform's AI capabilities, expand the team, and grow partnerships with carriers and brokers across the U.S. - learn more
  • Strong Ventures led an ₩800 million pre-Series A funding round for LunchLab, a Seoul-based B2B startup offering corporate lunch subscription services. LunchLab provides daily lunchbox deliveries and post-meal dish collection for companies, streamlining office meal logistics. The funds will be used to expand production capacity, enhance delivery operations across Seoul, and improve their proprietary ordering app. - learn more
  • CIV participated in Crux's recent $50M Series B funding round, supporting the company's mission to streamline financing for clean energy and manufacturing projects. Crux, based in New York, operates a capital markets platform that facilitates transactions such as transferable tax credits and debt financing, aiming to enhance liquidity and efficiency in the clean economy sector. The newly acquired funds will be utilized to expand Crux's network of market participants, enhance its software infrastructure, and scale its operations to meet the growing demand for clean energy financing solutions. - learn more
  • Finality Capital Partners participated in the $11M seed funding round for Optimum, a startup incubated at MIT and based in Cambridge, Massachusetts. Optimum is developing a decentralized memory layer for Web3, utilizing Random Linear Network Coding (RLNC) to enhance data storage and propagation across blockchain networks. The funds will be used to advance Optimum's technology and expand its team to address scalability challenges in decentralized systems. - learn more
  • TIME BioVentures participated in Phantom Neuro's recent $19M Series A funding round. Based in Austin, Texas, Phantom Neuro is developing a minimally invasive neural interface called Phantom X, designed to enable intuitive control of prosthetic limbs and robotic exoskeletons. The new funding will support the company's first human trials, preclinical testing, regulatory submissions, and expanded research and development for broader applications of its technology beyond prosthetic limbs. - learn more
  • Veridical Ventures participated in a $2M seed funding round for SlashExperts, a San Francisco-based B2B platform that connects prospective buyers with existing customers to facilitate authentic peer conversations. This approach aims to build trust and expedite sales processes. The funds will be used to enhance the platform's features, ensuring seamless and effective connections between buyers and users. - learn more
  • F4 Fund participated in Boby.ai's $1.25M seed funding round, supporting the Istanbul-based startup's mission to develop AI-powered mobile applications. Boby.ai, founded by Gökçe Nur Oğuz, Onur Olgun, and Berat Oğuz, focuses on creating user-friendly AI tools for end-users, such as their flagship app Mozart.ai, which enables users to generate personalized music using AI. The funding will be used to expand the team and develop new AI-based mobile products. - learn more
  • Riot Ventures and Impatient Ventures participated in Blue Water Autonomy's recent $14M seed funding round. Based in Boston, Massachusetts, Blue Water Autonomy is developing fully autonomous, unmanned ships designed to operate on the open ocean for extended periods. The company plans to use the funds to expand its engineering team, accelerate ship testing, and integrate various payloads onto its platform. - learn more
  • Aliavia Ventures led a $1M pre-seed funding round for InsightWise, an AI-powered platform based in Sydney, Australia, designed to streamline the consulting process by automating tasks such as proposal development and strategy creation. The funding will be used to enhance the platform's capabilities and support expansion into the U.S. market. - learn more

LA Exits

  • Pex, a leading provider of digital rights technology, has been acquired by Vobile, a global leader in digital content protection and transaction services. This acquisition enhances Vobile's services for the music industry and strengthens its position as a global solution provider for digital audio content. - learn more

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Rain's Latest Funding Fuels the Future of Financial Wellness

🔦 Spotlight

Happy Friday,

This week, the LA tech scene buzzed with news that Rain, a leader in financial wellness, hassecured $75 million in Series B equity funding, spearheaded by Prosus. This isn't just another funding round; it's a pivotal chapter in Rain's mission to transform how American workers interact with their earnings.

Since its inception, Rain has been at the forefront of innovation in financial technology, particularly with its earned wage access solutions. The concept was simple yet revolutionary: allow workers to access their earned wages instantly, mitigating financial stress and dependency on high-interest payday loans. This vision quickly gained traction, propelling Rain from a promising startup to a key player in the fintech space.

What makes this Series B funding particularly noteworthy is what it represents on a larger scale. It's not just an influx of capital but a strong endorsement of Rain's potential to expand even further. With previous rounds fueling their initial growth and strategic partnerships, such as their notablecollaboration with Marqeta to enhance payment technologies, Rain has steadily built a foundation not just for success but for significant impact.

As Rain secures this significant new funding, their initiative to reshape financial wellness is set to expand dramatically, showcasing the profound impact tech can have on everyday financial challenges.

Looking forward to seeing how their innovations will drive change in the financial landscape.

🤝 Venture Deals

LA Companies

  • Dosen, a Los Angeles-based HRtech startup founded by Ronan Wall, Victor Burke, and Cian McCarthy, has secured $2.3M in an oversubscribed pre-seed funding round led by Affinity Ventures. The company offers an AI-powered platform that aligns employee-led learning with business goals through personalized, gamified development programs. The funds will be used to scale the platform, enhance AI-driven personalized learning, and improve employee engagement and productivity. - learn more
  • Plug, a Santa Monica-based company operating an EV-exclusive wholesale online auction platform, has secured $6.7M in an oversubscribed seed funding round led by Floodgate, Autotech Ventures, and A*. The company has also launched Plug Trade Desk™, the first EV-focused service designed to help dealers confidently price, move, and monetize trade-ins. The newly acquired funds will be used to enhance Plug's technology and expand its services, aiming to support dealers in navigating the growing used EV market. - learn more
  • Gallatin AI, a defense tech startup, has raised $15M in seed funding led by 8VC to scale its AI-powered logistics platform, Navigator. The tool helps military logisticians predict, plan, and execute operations more efficiently in contested environments. Funds will be used to expand the team and deploy the platform across military services. - learn more
  • BLNG AI, a generative AI platform based in Los Angeles and Paris, raised $3M in seed funding led by Speedinvest to streamline jewelry design by turning sketches into photorealistic renderings and animations. The funding will support commercialization, team expansion in Europe and the U.S., and the launch of a subscription-based app for luxury brands and independent jewelers. - learn more
  • Amca, a newly launched aerospace company focused on modernizing the industrial supply chain, has raised $76M in funding from investors including Caffeinated Capital, Founders Fund, Lux Capital, Andreessen Horowitz, and others. The company plans to acquire specialized suppliers and develop new aerospace products, aiming to strengthen and future-proof the sector’s manufacturing and innovation capabilities. - learn more
  • Turbine Finance Corp., a Santa Monica, California-based data science-driven liquidity platform, has raised a total of $21.75M in equity funding, comprising a $13M Series A round co-led by Alpha Edison and TTV Capital, and a previously unannounced $8.75M seed round with participation from Fin Capital, B Capital, and Sozo Ventures. Additionally, the company secured up to a $100M warehouse facility from Silicon Valley Bank to provide credit facilities to venture investors. The combined funding of $121.75M will be used to deploy the warehouse line and expand Turbine's data science team. Turbine's platform enables private equity and venture firms to offer limited partners access to the value of their portfolio investments without reducing exposure, leveraging machine learning to expedite underwriting processes. - learn more
  • Gente Beauty, an innovative Brazilian body care brand, has received a lead investment from Webster Capital, a private equity firm specializing in consumer and healthcare sectors. This partnership aims to support Gente Beauty's growth and expansion in the beauty industry. - learn more
            LA Venture Funds
            • Alexandria Investment Partners participated in a $41M Series A round for Solu Therapeutics, a Boston-based biotech company developing targeted protein degradation therapies. The funding will advance its lead candidate, STX-0712, which recently entered a Phase 1 clinical trial for CMML and other advanced blood cancers. - learn more
            • Calibrate Ventures participated in SigIQ.ai's $9.5M seed funding round. SigIQ.ai, based in Berkeley, California, is an AI tutoring startup focused on providing personalized education through advanced AI models. The funds will be used to hire top talent, enhance their AI models, and scale their platforms to educational systems worldwide. - learn more
            • Rusheen Capital Management participated in Zero Industrial's $10M Series A funding round, aiming to accelerate the development of thermal energy storage solutions in North America. Zero Industrial focuses on deploying large-scale thermal energy storage projects to enhance energy efficiency and support decarbonization efforts. The funding will be used to expand their project pipeline and advance the commercialization of their technology. - learn more

            LA Exits

            • Bread Beauty Supply has been acquired by Cost of Doing Business (CODB), a holding company founded in 2024 by Topicals founder and CEO Olamide Olowe and president Sochi Mbadugha. The acquisition aims to expand Bread's retail presence in the U.S., starting with an increased footprint in Sephora stores. Founder Maeva Heim will continue as Chief Creative Officer, focusing on the brand's creative direction, while CODB will manage strategic operations. This move reflects CODB's commitment to supporting Black-owned businesses and fostering diversity in the beauty industry. - learn more

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