Alaska Airlines’ Brad Tilden: Competitors Make You Better

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.

Alaska Airlines’ Brad Tilden: Competitors Make You Better

This episode was originally released in April 2017. Press Play below to listen.

About this episode's guest:

  • CEO of Alaska Air Group since 2012
  • Has been with the company for 25 years in various leadership roles
  • Closed acquisition of Virgin America in December 2016 for $2.6 billion
  • Holds a commercial pilot's license
  • Learned to play the ukulele from YouTube


Topics covered in this episode:

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: Hey, Brad. Great to see you.

Brad Tilden: Great to see you, Spencer.

Rascoff: I'm a huge user of your product.

Tilden: Thank you.

Rascoff: I'm almost always on your planes, and I'm grateful for it, so thanks for being here.

Tilden: Well, thank you for saying that. I'm a huge user of your product as well. What you guys have built is just amazing, and it's a company that everybody in Seattle's very proud of.

Rascoff: Thank you. Thank you. So like we, you have engaged in transformative M&A.

Tilden: Yeah.

Rascoff: You acquired a huge company from Virgin America. Walk our listeners through the rationale for that acquisition. Tell us how the deal came together, and then we'll talk about the regulatory process around approval.

Tilden: Sure.

Rascoff: So how'd the deal come together and why?

Tilden: Yeah. You know, so some folks listening will know Alaska. Probably others will be less familiar, but we've been around for a long time. We're a high-growth airline. We've grown at 7 or 8 percent a year for 20 years. We've tripled in size in 20 years. But notwithstanding that, the industry structure is changing more rapidly than us with all the bankruptcies and all the consolidation. It used to take nine airlines to make up 80 or 85 percent of the pie. Today, it takes four.

And so we came to a couple of conclusions. One, we're proud of what we do. We think we bring value to our employees and our customers and our communities, and we thought we want to be around. And we just said with the change in the industry structure, it would be better for us if we were larger. So we have been growing organically a lot. We'll continue that relatively high rate of organic growth. But we decided that M&A would be good as well.

Rascoff: Alaska was frequently mentioned as a consolidation candidate for someone else to acquire, but you just decided –

Tilden: You know, other people mentioned that.

Rascoff: [Laughs]

Tilden: I'll just say we've been – as I said earlier, we're proud of the way we run the business, and I think we bring a lot of value to our customers and our employees. And we have never had any interest at all in being acquired. We want to stay Alaska and keep doing what we're doing for 20, 30, 40, 50 years and into the future.

Rascoff: And why Virgin America?

Tilden: I guess, here's the things you say about Virgin America. They're on the West Coast, which is usually attractive to us. When we look at Alaska, we fly to 35 states, 5 countries, but we have real concentrations of loyalty in Alaska, Washington, and Oregon. Virgin's got real strength in California. They've got a great presence in SFO and at LAX. So when you take Virgin America and Alaska, you take our strength in the Pacific Northwest and Alaska, theirs in California, and the whole idea here is that we become the go-to airline for anybody living anywhere on the West Coast.

Rascoff: So the route network was particularly –

Tilden: Super attractive.

Rascoff: OK.

Tilden: That's right.

Rascoff: Actually, let's talk about the regulatory process, first, before we get into the brands and the culture and the integration plans. It took about six months for your deal to get approved. Is that right?

Tilden: It took a bit more. We announced it on April 4 [2016]. I think we closed in mid-December, so a little bit more.

Rascoff: And who needs to approve an airline deal? Is this –

Tilden: The Justice Department.

Rascoff: DOJ and also FAA?

Tilden: No. The FAA doesn't. They will have to approve – we'll have to go to a single operating certificate, which the FAA will have to approve that, but that'll happen a year from now.

Rascoff: OK. And what was that DOJ process like? Was it touch and go, or you were pretty confident that it would get approved?

Tilden: You know, I will say that I think we were always pretty confident that it would get approved. You end up making concessions, and you make small adjustments to the deal to get it approved. But I think we were always confident that it would get approved. It's intensive. There were several trips back to Washington, DC, to talk with these folks. They look at every e-mail you've ever written and anything that's on your hard drive. I don't know. I think Alaska came out of that fine, and we learned something about how you do M&A in the process, and, ultimately, we got the deal done.

Rascoff: So I had my own grilling.

Tilden: [Laughs]

Rascoff: It took us around the same time, six to nine months, for the Zillow-Trulia merger to be approved by the Federal Trade Commission. I guess, in M&A, sometimes the DOJ reviews deals, sometimes FTC. We got FTC. And I made dozens of trips on Alaska, of course –

Tilden: Thank you.

Rascoff: – that Seattle to Dulles redeye many, many times. And we spent a God-awful amount of money on lawyers working through that process. It was very hard on the employees during that period. There was a lot of uncertainty, especially at Trulia, the company that we were acquiring. They didn't know would the deal get through, would they have a job after the deal got through, etc. So what was it like as an employee at Alaska or Virgin America during that waiting period?

Tilden: Spencer, I think you're making a really fair comment. I think I would guess it was harder on Virgin America employees than Alaska. It's a business combination, but Alaska's the acquirer. Probably Virgin employees had some of those anxieties and questions that you're mentioning. You do what you can. That time period's an awkward time period, because if you buy the – if you're successful, every decision the company has made is yours. You get whatever amount of money's in the bank account when you close. So any decision they make in that six or nine months, you inherit.

Rascoff: And you're sort of rooting for a company that might, if the deal doesn't go through, go back to being a competitor.

Tilden: That's right.

Rascoff: I mean, that was our situation between Zillow and Trulia. We were like, “OK. Do we root for them to do well during this period or not?"

Tilden: But because you might become competitors, the most important competitive information, you don't know. Route decisions, pricing decisions, marking decisions, you don't – loyalty, you don't see any of that during the period. And even Virgin America employees, we really had limited opportunity to work with Virgin America employees during the period –

[Crosstalk]

Rascoff: Yeah. I desperately wanted to go speak to Trulia employees in that period and tell them, you know, to hang in there and I know this must be hard, but this will end at some point, and then we'll all be on the same team. But I wasn't allowed to do that.

Tilden: We were able to do a few meetings, but it wasn't – it's nothing like it is now.

Rascoff: Right.

Tilden: Yeah.

Rascoff: So you said the route network was one of the major reasons that you were attracted. Let's talk about the product and the brand. I've flown Virgin America plenty. It's an amazing product, but it's very different, actually, from other airlines, including Alaska. So how would you describe that product, and, more importantly, for our listeners, how are you going to integrate that product, and what are you going to do with these two brands?

Tilden: Yeah. You know, I think the first thing we'd say is there are clear differences. There are also a lot of similarities. Two similarities between both companies – both companies really focus on customers. Both companies win awards – Virgin, Conde Nast Travel and Leisure for years in a row, Alaska, JD Power for nine years in a row. So both do well with customers, and both believe in doing well by customers by getting close with the employees, building alignment with employees, and encouraging our employees to go out and be their greatest. So that binds us.

Having said that, I would say Alaska's maybe a little bit more traditional. We're a little bit more Seattle. Virgin is, people would say, more hip, more, more flair. The mood lighting is big with them. The music is big with them. Uniform's a little bit different. Honestly, I think that's going to be good stuff.

As we move forward, I can tell you now the name of the company is going to be Alaska Airlines, but we're going to separate that from the brand decision. The brand is – we're actually going to incorporate some elements of Alaska but a lot of elements from Virgin America, so –

Rascoff: In the product.

Tilden: In the product.

Rascoff: So I'll get on an Alaska Airlines plane, but it'll be a little more hip than it used to be. It that what [ laughs] –

Tilden: I think you'll see music. I think you'll see mood lighting. I think you'll see satellite – we don't have satellite on our airplanes now –satellite connectivity, really top-notch entertainment system. We're going to adopt a lot of those features.

Rascoff: What about the cabin configuration, which is pretty different? I think Virgin America usually has a small first class, and Alaska has a little larger first class.

Tilden: That's right. So you're asking a great question. We're actually going to go to the Alaska standard there. So what that'll mean is Virgin has eight first-class seats. We're going to go to 12 on some of their airlines, 16 first-class seats on other airplanes. So it'd be a lot more first-class seats.

Everything comes with a price. So with Virgin, you know, they had that beautiful first class seat, but nobody ever upgraded. A Gold 75K never got upgraded into first class. So we'll move to the Alaska model. And one of the things we're really proud of at Alaska is we lead the industry in generosity. So if you're an MVP Gold 75K, even an MVP, you will upgrade into those seats a lot. I think we calculate that Gold 75Ks, 90 percent of the time, you'll be able to upgrade to either premium class or first class. If you're even a Gold, you'll upgrade 70 or 75 percent of the time.

Rascoff: And what about the aircraft selection? So Alaska is famously all Boeing, and I think every plane says, “All Boeing," on it. And Virgin America flies Airbus, I think, right? Have you made a decision about aircraft?

Tilden: No. I mean, I know you would know this from your Trulia/Zillow experience, but you just begin to trust – you put a process in place for everything. It's not a Boeing/Airbus decision. The decision we need to make is it one fleet type versus two. If it's one fleet type, it's definitely Boeing. If it's two, it just means we hang on to these Airbus airplanes Virgin America has. But we're going to take six or eight months in 2017 and make that decision. And you can imagine, there are – I mean, the Airbus airplanes we already own. They're already bought. To actually change them out requires a lot of capital in changeover. So that's an argument against changing. On the flipside, there are huge benefits in an industry like ours to a common fleet type.

Rascoff: So how much does it cost to take a Virgin America Airbus and repaint it and turn it into what will be a newly branded Alaska plane?

Tilden: Like, a lot of questions, it does depend, but it's millions. It's not –

Rascoff: Millions to change a plane?

Tilden: It is. It is. It is.

Rascoff: Wow.

Tilden: The paint is between one and two hundred thousand dollars, but the – it's millions. When you look at sidewalls and the overhead units, the seats, the entertainment, it's millions per airplane.

Rascoff: I was on an Alaska plane the other day that it said, “Employed powered," and it signatures of all the employees. Are there a lot of those, or that's _____ _____ –

[Crosstalk]

Tilden: No. That's the only one of those.

Rascoff: That's the only one. OK. And how many Disney planes are there – the Disneyland ones.

Tilden: You know, we've got three or four. There's Toy Story. There's Disneyland. There's Tinkerbell. There's Cars.

Rascoff: And do they pay you for that?

Tilden: [Laughs] We have a fantastic partnership with Disney. Yeah.

Rascoff: My kids love seeing those, and they feel lucky when they're on them. Let's talk about employee culture and engagement. This is something that you're very focused on, very proud of. And in particular, through the integration, did you change anything about your general approach to employee communication?

Tilden: You know, one of the things that we sort of – we did, Spencer, is the quick answer to your question. Airlines, there's two ways of looking at an airline. There's all these intricacies that need to happen for one flight to depart – when it gets fueled, how the flight plan gets done, when it gets catered, all the moving pieces, everything that needs to happen before departure for one flight a day, and we have 1,200 flights a day. And so I think in the old days, 15, 20 years ago, Alaska spent a lot of time on that stuff, on the process and the computer systems and how the airplane's routed, when pilots or flight attendants flew which trips.

There's another side of the business that I think a lot of airlines have spent less time on, and that's just working with the employees. And it's an MBA term, it's an overused term, but are you actually aligned? Is everybody in that company actually trying to do the same thing?

Rascoff: Now, why do you think the airline industry suffers from that uniquely, because not all industries – is it something about it being – is organized labor related to that?

Tilden: It's complicated. I think we started in a regulated era. Most of these airlines that you would recognize, they started like a utility company as a regulated industry, where you went to the government and said, “Hey, can I fly a new route?" The government said yes or no. And if you flew that route, your fare was calculated as your cost structure plus a certain margin on your costs to provide for –

Rascoff: So the impact of that is they didn't have to focus on building your employee culture, because their profit was kind of preordained by regulators.

Tilden: That's right. That's right. They also didn't have to focus on their cost structure. So 1978, 1979 came, and airlines like Southwest, JetBlue, Frontier, Spirit, Virgin America came onto the scene, and they put a lot of pressure on these old companies and the older airlines, and Alaska was one of them, but we all had to lower our costs. We had to utilize aircraft more. We had to restructure our companies. And the pensions were – and Alaska, we're really proud. We did not file for bankruptcy. But even at Alaska, we had to do some serious restructuring. And I think bottom line, those restructurings were hard on our people.

Rascoff: Because usually, frequently airlines go through bankruptcy so they can renegotiate their labor contracts and get out from under –

Tilden: Or leases.

Rascoff: – the debt or the pensions.

Tilden: Yeah.

Rascoff: And so Alaska never had to do that, but you've maintained good employee relations why? How?

Tilden: You know, I actually think – and I was chatting with one of our labor groups this morning. We had to restructure at Alaska as well. We had to change airplanes. We're slowly getting out of defined benefit pension plans. We did make wage adjustments for some of our groups, but we did it ourselves. If you go back to 2005, I think there are folks that would look at the Alaska Airlines story and say those weren't our greatest days. But when we look back now, we say we did it ourselves. We sat down across the table from our labor leaders. We respected them, and we actually – I personally believe through the process, we built a bond. We built trust, and we built respect for one another.

Rascoff: So isn't one of the issues on airline mergers how to deal with seniority when you're merging the two groups of employees? So how are you doing with that between Virgin America and Alaska?

Tilden: You know, that's actually an interesting thing. Seniority matters a lot. It's the trips you bid and what you get to fly. But interestingly, the airline management doesn't have a lot to do with that. We have a lot to do with the payment scenario and the work rules and the pensions and benefits.

Rascoff: So union leadership?

Tilden: It's between the two unions – seniority integration.

Rascoff: Let me explore the brand decision a little bit more. You acquired Virgin America, deal gets through, and at that point, did you start evaluating what to do with the brands, or you already knew going into the acquisition what you were going to do with the brands and the product?

Tilden: We started the process before we announced the acquisition, but we didn't complete it. Two or three months ago the process completed, I would say.

Rascoff: And to arrive at this decision, the decision of keeping the Alaska – if I understand correctly, you're going to use the Alaska brand, retire the Virgin America brand.

Tilden: That's correct.

Rascoff: But takes some elements of the Virgin America product –

Tilden: That's exactly right.

Rascoff: – and incorporate it into Alaska. Describe how you arrived at that decision. What research did you do? Who's involved in that?

Tilden: We did a ton of research. I can't remember the numbers, but we got insights from thousands of customers. We did maybe 70 or 80 focus groups. We brought lots of our employees into the conversation.

We actually looked at – we took the industry. The industry's basically $100 billion industry. And we took the industry. We broke it down into demand pools. We said, “You and I might be in one demand pool when we're traveling for work. We might be in a different demand pool when we travel to Palm Springs on the weekend." But we started to say what are these different demand pools.

And we said what brands are out there, what space does American have already or Southwest have already? Then we just started to correlate. Said what is the – if you look at the demand side of the equation, what is it that people want. And then if you looked at the supply side, what is it that airlines already providing. Then you look at your own capabilities. What is it that we think we're good at. And candidly, I would say what I think we're good at is we do good with business people, and we do good with higher-end leisure travelers. We have a low-cost, sort of low-fare position, but it's probably not the total no frills airline that you might see out there.

So there was a ton of research done. And as we looked at the research – and then you looked at, you know, what do people feel about the Alaska Airlines name? What do people feel about the Virgin America name, and how should you move forward?

Rascoff: So there were really only four choices available to you as I think through it. You could keep the Alaska brand. You could keep the Virgin America brand and switch Alaska over. You could operate them both simultaneously, which is what we've done at Zillow Group with Zillow and Trulia, or you could launch a brand-new brand.

Tilden: That's right.

Rascoff: Did you have a hypothesis going in, you personally, as to which of those four answers was the right answer before you did all the research and analysis?

Tilden: I think if you talked to folks at Alaska in our leadership team, there were several different hypotheses. I personally thought running two brands at first might be – I thought that might be the way we ended up going. The Alaska brand has an enormous amount of equity, and I also thought that might be a place we went.

As you get through the research, you just sort of – in the airline business, I think our space is different than yours. You look at people, whatever, they need to fly Anchorage to Seattle, and then they're going to fly to San Francisco. They might do Anchorage -Seattle on Alaska, and if you run two brands, do that next leg on Virgin. And there's a little friction there, or people showing up at an airport to pick somebody up or drop somebody off or duplicate costs for airport facilities.

As we looked at it more and more closely, there are people that love the Alaska brand more, and there are people that love Virgin more, but in – so there would be some benefit that you have to acknowledge of running two brands, but there's a cost. And what we concluded was the cost of running two brands is greater than the benefit.

Rascoff: Does the word Alaska in your brand hold you back because people in, you know, Florida or New York think it's, you know, an oddity?

Tilden: Yeah. You know, it's a good question, but I don't think so. I think if you look at Southwest Airlines, you know, nobody expects Southwest to fly in the southwestern part of the United States, even though they fly, they're don't expect them to fly exclusively there. One we talk about in Seattle is Amazon. You know, someone things about Amazon, nobody thinks about the river. And so I think it's a valid question, but there's a lot of historical goodness to Alaska. There's good things we've done for customers and communities and employees. The challenge we have is to go out and to folks that are less familiar with us, help them understand why this is a great company and a great name.

Rascoff: So how do you make decisions? Now that you have this brand of Alaska, and you're trying to decide what routes to invest in, to expand in, is that driven – I guess, I'm trying to understand how those decisions get made. Is it mostly driven by the economics of what the current airlines that fly those routes are charging, so there's potential there and you can get gates, or is it based on what your users tell about where they want to go? I mean, how do you decide what routes to add?

Tilden: I think in the old days, I mean, we would do a P&L forecast for any route that we'd want to fly. And in our business, we still share a lot of information with the Department of Transportation. So we know how many people fly between any two city pairs. We know exactly how many people fly. We know exactly what the average fare is. We actually know the connecting. If you're talking about Seattle – Denver as an example, we know the connections that come down from Anchorage. We know the connections beyond Denver. So you actually have great information about the market today. You don't how much bringing your service in is going to stimulate the market.

So that's one piece of it is being really good at doing a route forecast. And I would say folks at Alaska, this is something we're – we've got a lot – we've added 110, 120 cities in the last five or six years. We've got a lot of confidence in our ability to build a route forecast and sort of believe that our performance will be close to the forecast. That is only part of it.

It's got to mix with a strategy of going to market and building loyalty. And if you look at what we're trying to do now, part of it is the micro forecast, but we're trying to go into a market like San Francisco or San Jose and say, “Hey, we'd like you to consider flying with Alaska Airlines and Virgin America. Consider joining our loyalty program. Consider having our credit card in your wallet." And people won't – it's a little bit of a chicken and egg scenario. They won't get your credit card or get into your loyalty program into you fly them enough places. And then when you fly to more places, they'll get into your loyalty program. And then once they're in the loyalty program, you add a new route, and the route will be successful.

So I think if you look at what we're doing today, we are doing a lot of that micro forecast, but it's also – we're going down into California. We're getting involved in the communities. We're marketing. We're trying to build loyalty in the loyalty program. We're adding new cities. We're advertising like crazy. So it's all of it together.

Rascoff: So one of the pieces of the brand positioning of Alaska, at least here in Seattle, is the hometown aspect, that this is your hometown airline. And I'm sure in Alaska, it's probably tenfold. When Delta moved into Seattle, they tried to sort of usurp that positioning, right? I guess, talk through how you do national and local marketing and how you – you have this product, which is obviously national, international really. But all these decisions are actually made locally. So explain how your national brand and your local positioning interact with one another?

Tilden: You know, one of the things that we believe is a lot of our success is you've got to be effective locally. If you look at it – as I said earlier, we fly 118 cities or something like that. But a market like Anchorage is really important. A market like Seattle is really important. Portland's really important. The Bay Area – San Francisco, San Jose – is going to be important.

So a lot of our thinking is more local. We need to go into those communities, build loyalty, do the right – I mean, Seattle, we've been there for – our headquarters have been here since 1954, so we want to be involved. We want to be showing up, doing the right things and providing good utility, good value, low fares to our customers. And then I think you have a chance of earning people's trust and loyalty. So I don't know. We are doing more and more national things, but if I had to choose local or national, I would choose local for our business.

Rascoff: So for example, UW Stadium is Alaska Airlines –

Tilden: It's local.

Rascoff: – arena, and that's a form or your local marketing.

Tilden: That's right.

Rascoff: Probably pretty hard to calculate the ROI on the naming rights –

Tilden: It is.

Rascoff: – on a college stadium. Do you even try, I mean, or is it just, you know, your gut says that that raises your brand awareness locally and –

Tilden: You know, one of the things that people say about marketing is half the money's wasted. You just don't know which half. And I think you look at a relationship like University of Washington, we've been affiliated with those guys forever. We know that a lot of our Golds and Gold 75Ks are alum. We know that they're in the stands on the weekend. When you look at something like UW, you can say, “Well, you know, what are the economics of this and how does that compare to the next thing?" But getting to ROI, honestly, I think that's tougher. You go with some gut feel.

Rascoff: Let's shift topics and talk about leadership, something that I know you're passionate about. In your view, what's the role of a leader? What does it even mean to be a leader?

Tilden: I think the leader helps the company chart a future, develop a strategy, figure out where you're going, bring people together. But, like, in our space, I think one of the under-appreciated, one of the really important parts of the being a leader is building alignment with your team. We had a person on our board said, you know – it was a military analogy – said, you know, “A bad plan with a great army that's totally motivated to execute it will always beat a good plan with an army that's not motivated and there's no sense of teamwork."

So I think a real job of a leader in our space especially, is to build that sense alignment, build that sense of teamwork. Part of it is you've got to figure out where you want to go, what is the strategy, what are you trying to do with a loyalty program, a new market announcement, a fleet, whatever it might be. The bigger part of the job is bringing your team along, getting them to follow, getting them to go out there and be great and help your company move forward. So that's something that I think Alaska in the last five, six, seven years has spent a lot more energy on, and I think it's paying off.

Rascoff: I mean, you got high praise for this. Everything I read and hear about the way you lead and manage is fantastic. When you're hiring a leader or when you're thinking about whether one of your direct reports is a good leader, how do you assess that?

Tilden: Like, I'm sort of into my career now, and you try different things on at different points of your life. But now, I look for four things in people. You want someone that's smart. That's really important. If it's a CFO, they've got to be good CFO. They've got to be good at their job, know how to close the books, communicate with Wall Street, whatever it is. They've got to have that.

The next two are even more important. I want people that really identify with our company. I call it they're clipped in. It's personal for them. They are totally bought into what Alaska's trying to accomplish, and they are totally, personally convicted about us getting to where we want to go.

And then the final one is how they work with other people. And it's something I've really grown to appreciate the last four or five years at Alaska. There are people that are sort of sharp elbows, and, “I just want to be ahead of you. It doesn't matter if I get ahead or if you go down," or there's people that really want to – they generally want to see their peers do well. And that's the people that collaborate. They want to work together, and they want to see their – they want to enjoy success themselves, but they also want to see their peers enjoy success.

Rascoff: They celebrate teamwork.

Tilden: That's right.

Rascoff: I was on a flight the other day, and the captain of the plane's son was the head flight attendant –

Tilden: Oh, my gosh.

Rascoff: – which was super cool. So, you know, they were both super excited to be working together. So, I guess, that's teamwork, but, you know.

Tilden: Fantastic.

Rascoff: What's the best advice that you've ever received, and tell us that story?

Tilden: I don't know. Bill Ayer was the previous CEO at Alaska Airlines. He was a great mentor to me. And I don't remember him actually saying this, but his lesson was just keep at it. Whatever it is that you're doing, make sure you're doing it for the right reasons, that you're justified it's appropriate. It's a good strategy. It's a good place to go, but just persevere. Just keep going at it. And if you do, and if people sort of see the goodness of what you're trying to accomplish, they see the value of it, they'll come along. And that's something I learned from him that I think was really important.

Rascoff: How has technology impacted your company and your industry over the last 10 years?

Tilden: It's huge. I mean, I could ask you all of these questions _____ _____ Zillow –

Rascoff: You have to get your own podcast. Then you get to ask the questions.

Tilden: [Laughs] There's a suggestion. That's a good idea. But, no. People buy tickets from home. Alaska was the first airline in 1995 to let you buy a ticket over the internet. You can print your boarding pass at home. Alaska was the first to do that. You can go to an airport, use a kiosk. Alaska led there as well. You can check in with an iPhone now.

Rascoff: So how many – yeah. I mean, I use your app all the time. So approximately how many software engineers do you have?

Tilden: I think it's in the neighborhood of 400 people now, something like that. I will tell you. It's an area that where our spending is quadruple what it was maybe five years ago in that area.

Rascoff: It's a good reminder that really every company is technology company now.

Tilden: It is. It is.

Rascoff: I mean, there are more software engineers at Morgan Stanley than Facebook. It's like –

Tilden: Isn't that amazing?

Rascoff: – and many more than Zillow. So it's, I guess, airlines, which are thought of as a traditional industry, are technology companies.

Tilden: No. Even, like, in the old days, all the computer was either on the airplane itself in the avionics or it was Saber. We used Saber for the backend. And now, there's maybe – there's hundreds of systems that are critical to us and we rely on every day to get weather, plan a flight, know where the airplane is, know where to deice, know – there's systems for everything, and we're relying on them.

Rascoff: I spoke the other day at a business school, and someone asked me a question that no one had ever asked me, so I'm going to end by asking it of you. They said if you had one magic bullet that you could shoot any competitor of yours with and that competitor would just disappear, which competitor would you choose and why?

Tilden: Yeah. You know what? It's a great question. I think I might not answer.

Rascoff: [Laughs]

Tilden: I think a lot of people might actually guess how I would feel or how Alaska would feel. But what we've learned at Alaska in the last three or four years and Seattle especially is that competition's actually good. We've had somebody come into Seattle and sort of take us on big time, but the company's taken a lot of risk in that time. We've added all kinds of routes. We've reconfigured our airplanes.

Rascoff: It's made you better.

Tilden: It's made us a little bit better, made us way better than we were. There's a tempting answer to that question, but I think the better way to train yourself is you want to be with the best, whether you're running a marathon, competing in football, running an airline, you want to be competing against the best, because that will make you better.

Rascoff: Brad, thanks very much. I appreciate it.

Tilden: Thank you, sir. It was fun.

Rascoff: Thank you.

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Observable Space Raises $90M to Build Beyond Rockets

🔦 Spotlight

Hello Los Angeles,

Space infrastructure is having a week.

Los Angeles-based Observable Space closed a $90M Series A and announced a $94M U.S. Space Force contract to scale its optical sensing and laser communications platforms. The round was led by Lux Capital and co-led by Upfront Ventures, Detroit Venture Partners, Island Green Capital and RTX Ventures, with participation from BRV Capital, Fathom Fund and Venrex.

Observable Space is building advanced optical systems across three areas: laser communications ground stations, ground-based optical sensing and in-space payloads. In simpler terms, the company is working on the infrastructure that helps satellites and spacecraft see, track, navigate and communicate more effectively.

Image Source: Observable Space

The Space Force contract gives Observable Space an early $22M in task orders under a larger $94M award to deploy mobile, off-grid optical sensing stations for space domain awareness. These systems are designed to help track objects in orbit with more resilient, lower-cost and geographically distributed ground infrastructure.

That matters because space is getting more crowded, more commercial and more strategically important. Satellites are no longer just sitting quietly above us handling GPS, weather and communications. They are becoming part of a much larger network for national security, AI, connectivity and future space-based infrastructure.

Observable Space’s work sits in the less flashy, but increasingly critical layer of the space economy. Rockets may get the liftoff footage, but the next phase of space competition will also depend on who can track what is in orbit, move data quickly and keep communications reliable from space to ground.

The company says its platform has already executed 2.6M automated tasks, identified more than 20M targets and completed 84,000 hours of continuous orbital monitoring. It is also expanding manufacturing across Detroit and Los Angeles, with spacecraft, engineering and design labs based in LA.

For Southern California’s space ecosystem, Observable Space adds another signal that the region’s advantage is not just launch. It is the full stack around space: optics, software, sensing, communications, payloads and the infrastructure needed to make orbit more usable.

Now onto this week’s LA venture deals, fund announcements and acquisitions.

🤝 Venture Deals

    LA Companies

    • Fragrance brand ’Ôrəbella closed a Series A growth equity investment led by Silas Capital, with participation from existing investor Celebrands, which incubated the brand. The funding will support global expansion, product innovation and retail growth as ’Ôrəbella scales beyond its Ulta Beauty base into international markets including Douglas, Selfridges and Ulta Beauty Middle East. The company also named Anish Agarwal, formerly CEO of T3 Micro, as CEO. - learn more
    • Ember LifeSciences added new strategic investments from Amgen Ventures and TDF Ventures, bringing its total Series A funding to $27M. The company makes reusable, temperature-controlled cold chain technology for transporting medicines and vaccines, and recently announced full commercial availability of its Ember Cube 2, which provides real-time monitoring and cloud-based tracking for healthcare logistics. Financial terms of the new investments were not disclosed. - learn more
    • Iconic raised $6M to build its AI-enabled M&A advisory platform for small business owners. The company combines AI software with human advisors to help owners sell businesses that are often too small for traditional investment banks to support, especially those valued under $20M. Iconic is aiming to modernize the small-business sale process as millions of baby boomer-owned businesses prepare to change hands. - learn more

    LA Venture Funds
    • Capital Group participated in Anthropic’s $65B Series H, which was led by Altimeter Capital, Dragoneer, Greenoaks and Sequoia Capital, valuing the company at $965B post-money. Anthropic said the new funding will support continued AI safety research, expanded compute capacity and broader product development as demand for Claude grows across enterprise customers and developers. - learn more
    • WndrCo participated in Reactor’s $59M seed and Series A funding, which was led by Lightspeed Venture Partners with backing from Amplify Partners, Sky9 Capital, FPV Ventures and others. San Francisco-based Reactor is building a developer platform for real-time generative video and “world models,” giving developers SDK and API access to create interactive AI applications across media and entertainment, physical AI and robotics. The company was co-founded by former Apple Vision Pro technical leads Alberto Taiuti and Bryce Schmidtchen, and WndrCo founding partner Jeffrey Katzenberg will join as a board observer. - learn more
    • Upfront Ventures led Kubera Health’s $6.5M seed round, with participation from Company Ventures, Dria Ventures and SemperVirens. Kubera is building a contract-to-payment system of record for healthcare, helping providers translate complex payer contracts into auditable payment logic so they can better identify underpayments, reimbursement gaps and administrative inefficiencies. The funding will support product development and growth as the company works to modernize healthcare’s payment infrastructure. - learn more
    • Sound Ventures participated in Polsia’s $30M round, alongside True Ventures, Offline Ventures, Adjacent, Tekton Ventures, Drysdale Ventures, VaynerFund and angel investors. Polsia is building an AI operations platform designed to run company workflows across coding, research, sales, customer support, ads and investor diligence, with founder Ben Cera saying the company is approaching $10M in annual run rate with one founder and no employees. The round valued Polsia at $250M. - learn more
    • Blue Bear Capital participated in Lastwall’s $16M Series A extension, which was led by BDC Capital’s StrongNorth Fund, with additional backing from New Brunswick Innovation Foundation, Frostbite Capital, BlueWing Ventures and 18West. Fredericton-based Lastwall builds identity-first, quantum-resilient cybersecurity software for defense, government and critical infrastructure environments, with the funding going toward expanded deployment across North American municipal utilities, defense infrastructure and public sector cloud portals. - learn more
    • Upfront Ventures participated in Itera’s $12M seed round, alongside Costanoa Ventures and Colle Capital, as the deep tech company emerged from stealth with its real-time electronics prototyping platform. Itera has developed a fluid circuit board that uses glass and liquid metal to let engineers rewire and test real electronic designs in under a minute, aiming to cut traditional PCB prototyping cycles from weeks to days. The funding will support the launch and commercialization of its first product. - learn more
    • Rebel Fund participated in Didit’s $7.5M seed financing, alongside Y Combinator, Pioneer Fund, Orange Collective, Founders Future, Phosphor Capital, SaaSholic and angel investors including Tomer London and Taro Fukuyama. San Francisco-based Didit is building AI-native identity and fraud infrastructure for verifying people, businesses, wallets, transactions and AI agents, with the new funding going toward global go-to-market growth, product expansion and hiring across sales and customer success. - learn more
    • Fifth Wall participated in NavigateAI’s $25M seed round, which was led by Elad Gil and backed by investors including Khosla Ventures, Lennar, Tishman Speyer and Helix Electric. Founded by Opendoor co-founder Eric Wu, NavigateAI is building an AI coach for construction workers that helps answer job-site questions, troubleshoot issues and improve field productivity across construction teams. - learn more
    • Strong Ventures participated in K-Zone’s 6.3B won Series B, alongside TimeWorks Investment, BonAngels Venture Partners and Singapore-based Guardian Fund. K-Zone is building a global reverse logistics platform for returned, overstocked and obsolete inventory, using its REMEX platform and AI agents to automate buyer matching, deal proposals, sales workflows and market analysis as it expands further into the U.S. market. - learn more

    LA Exits

    • Comscore Movies, the box office data business used by studios and exhibitors to track theatrical performance, was acquired by Advaya Capital in a $70M cash deal. The business will be renamed Rentrak, reviving the brand Comscore acquired in 2016, and former Paramount domestic distribution chief Chris Aronson will join the board. - learn more

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      From Rocket Motors to Consumer AI

      🔦 Spotlight

      Happy Friday,

      This week, one company moved deeper into rocket propulsion while another pushed further into consumer AI. Different industries, different stakes, same underlying shift: technology is moving further into the infrastructure of defense and entertainment.

      In defense, Mach Industries acquired Exquadrum, a 24-year-old rocket and propulsion company based in Victorville. The deal was worth $50M in cash and equity and brings Exquadrum’s IP, facilities, business lines and 85 employees into Mach’s operation.

      Mach, based in Huntington Beach, has raised nearly $200M and is building autonomous aircraft and weapons systems. Exquadrum gives the company deeper control over solid rocket motors, propulsion testing and one of the more constrained parts of the defense supply chain. The company will now operate as Mach Energetics.

      For companies building unmanned systems, hypersonics and missile-defense technology, the hard parts are still very physical: propulsion, testing, manufacturing and production capacity. Mach’s deal shows how much of the defense tech race now depends on owning more of that stack.

      In entertainment, Paramount brought in former Google executive Barak Turovsky as EVP and Head of Consumer AI. In his LinkedIn post announcing the move, Turovsky said AI is beginning to reshape how consumers discover, engage with and experience content, especially across platforms like Paramount+ and Pluto TV.

      The hire comes as Paramount pushes deeper into AI, product and streaming technology under David Ellison. It also reflects a broader shift in Hollywood: studios are no longer just competing on content libraries. They are competing on discovery, personalization, engagement and the consumer experience around that content.

      The common thread is infrastructure. In defense, that means propulsion, testing and supply chain control. In entertainment, it means AI, product leadership and smarter consumer platforms. Both stories show how quickly traditional industries are becoming more technical, more integrated and more dependent on teams that can modernize the systems underneath them.

      Now onto this week’s LA venture deals, fund announcements and acquisitions.

      🤝 Venture Deals

        LA Companies

        • Clouted raised a $7M seed round led by Slow Ventures, with participation from Gold House Ventures, Weekend Fund, LINE-Yahoo’s Z VC, Gondor Capital, Iterative, AppWorks, Peak XV’s Surge and a16z Speedrun. The company is building a “Distribution Intelligence” platform that uses AI agents to help consumer and entertainment brands plan, execute and optimize viral marketing campaigns across UGC, clipping, fan pages, influencer seeding, paid ads and social platforms. Clouted says the new funding will support its AI infrastructure, creator network growth and expansion into gaming and streaming. - learn more
        • El Segundo-based Amca raised a $300M Series B led by Caffeinated Capital, with major participation from Lightspeed Venture Partners and continued backing from Andreessen Horowitz, Lux Capital, Construct Capital and House Capital, valuing the aerospace and defense manufacturer at more than $1B. The company builds critical aerospace and defense components by combining engineering, qualification testing, technical data and certified manufacturing into one platform, and plans to use the funding to expand its AI-powered RAPID system, acquire and build more factories nationwide and increase production capacity for major defense and aviation customers. - learn more
        • Kin Health raised a $9M seed round led by Maveron, with participation from Town Hall Ventures, Eniac Ventures, Flex Capital, Foundry Square Capital, Pear VC, The Family Fund and several individual investors, including GoodRx co-founders Doug Hirsch and Trevor Bezdek. The company is building a free AI-powered notetaker for healthcare visits that records appointments and turns them into plain-language summaries, next steps and shareable context for patients and caregivers. - learn more

        LA Venture Funds
        • Clocktower Technology Ventures participated in Robbin’s $8M seed round, which was co-led by Canary, Atlântico and Caravela, with additional backing from AB Seed, Norte Ventures and Tomorrow Capital. Brazil-based Robbin is building an AI-native B2B payments and credit platform that lets large industrial companies offer co-branded virtual cards and credit products to retailer networks, using Pix rails instead of traditional card networks. The company also structured a separate $100M FIDC credit facility with Augme, an XP Investimentos asset manager, to finance retailer purchases through the platform. - learn more
        • Upfront Ventures led CVRD Health’s $5M seed round, joined by Waterline Ventures and Distributed Ventures. CVRD helps government contractors manage employee benefits, fringe-dollar compliance and audit readiness under Service Contract Act and Davis-Bacon requirements, with the funding going toward platform development, compliance and member advocacy teams, and national expansion across federal contractors. - learn more
        • Sum VC participated in Hellbender’s $12.5M seed round, which was co-led by Magarac Venture Partners and Veredas Partners, with additional backing from Mana Ventures, Gaingels and the Active Angels Network. Pittsburgh-based Hellbender builds physical AI infrastructure and edge computer vision systems for autonomous and industrial applications, with the new funding going toward launching its on-edge AI camera line, expanding product and growth teams, and scaling domestic hardware manufacturing. - learn more
        • Rebel Ventures participated in Leadbay’s $4.2M seed round, alongside Y Combinator, Roosh Ventures, Inovexus Ventures, TS Ventures, Alumni Ventures, Bright Ventures, Transpose Platform, Deel Ventures and founders and executives from Deel, Gusto and Pennylane. San Francisco-based Leadbay is building an AI-powered sales intelligence platform that helps sales teams discover and qualify small and mid-sized businesses with little or no digital footprint, especially in data-scarce sectors like construction, hospitality, manufacturing, retail and B2B services. The funding will support its U.S. go-to-market expansion in San Francisco, AI research partnership with Sorbonne University and engineering growth. - learn more
        • Overture Ventures participated in Recheck’s $2M pre-seed round, alongside ReGen Ventures, Jetstream and MCJ. Recheck is a trust and compliance platform for residential solar that verifies sales reps, assigns portable Recheck IDs and has now launched Recheck Certified, a credential that combines ethical sales training, a code of conduct, background checks and ongoing monitoring to help installers and finance companies identify trustworthy sales professionals. Since launching, the company says it has verified more than 50,000 sales reps and 700 installers and dealers. - learn more
        • CIV co-led Calibre’s $3.3M pre-seed round alongside Vicus Ventures, with participation from I2BF Global Ventures, 9Yards Capital, Jigeum and angel investors including Nikesh Arora. London-based Calibre is building AI infrastructure for the testing, inspection and certification industry, helping automate certification workflows that still depend heavily on manual audits and document review across regulated sectors. - learn more

        LA Exits

        • 32 Flavors, the production company founded by Alex Baskin and known for unscripted franchises including Vanderpump Rules, The Real Housewives of Beverly Hills, The Real Housewives of Orange County and The Valley, was acquired by Sony Pictures Television, which took a majority stake in the company. Baskin will remain CEO, and the deal expands Sony’s premium nonfiction portfolio while keeping 32 Flavors’ existing leadership team in place. - learn more

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          Heaviside Raises $28M for Autonomous Precision Munitions

          🔦 Spotlight

          Hey Los Angeles,

          For years, Southern California’s defense tech story has largely been told through satellites, rockets, drones and software. This week, another category stepped into the frame: autonomous precision munitions.

          Los Angeles-based Heaviside Industries emerged from stealth with a $28M Series A led by Interlagos, with participation from Menlo Ventures, Flume Ventures, Cantos, Anorak Ventures and several individual defense and technology investors. The company, founded in 2024, is building autonomous precision munitions for U.S. and allied special operations and conventional forces.

          The round will help Heaviside accelerate development, production and delivery of its multi-domain munitions platforms, including its first aerial and underwater systems. According to the company, its products are designed to operate in jammed and GPS-denied environments, where legacy systems can degrade or fail.

          That detail matters. Modern warfare has been reshaped by unmanned systems, contested communications and the growing need for weapons that are not only precise, but affordable enough to be produced and deployed at scale. In other words, the defense tech race is not just about building more advanced systems. It is about building systems that can actually survive the battlefield they are designed for.

          Heaviside has been operating in stealth for more than two years and says it has built a team of more than 50 engineers and operators across Los Angeles and Oslo, Norway. The company also says it already has a roster of U.S. and allied customers, with the new funding going toward expanding production and accelerating deliveries domestically and abroad.

          For LA’s hard tech ecosystem, Heaviside adds to a growing defense-tech cluster that is less about splashy software and more about applied engineering. The company’s work sits at the intersection of autonomy, manufacturing and national security, where Southern California’s aerospace and robotics talent has become increasingly relevant.

          Now onto this week’s LA venture deals and fund announcements.


          🤝 Venture Deals

            LA Companies

            • Furientis emerged from stealth with a $5M pre-seed led by Silent Ventures, with participation from Bessemer Venture Partners, SV Angel and other investors. Founded in 2025, the defense technology startup is developing cost-effective, ship-based interceptor systems designed for scalable production, with the funding going toward initial production, expanded testing and hiring across engineering, manufacturing and operations. - learn more
            • Rogue raised a $2.5M pre-seed led by Science Inc., with participation from Uncommon VC, Simple Food Ventures and strategic investors, to accelerate its national retail and digital commerce strategy. Built by the team behind Dollar Shave Club and Liquid Death, Rogue makes high-protein chips and puffs with active probiotics, no seed oils and no artificial ingredients, and will launch in 2,800 Walmart stores nationwide in July. - learn more
            • Develo raised $14M led by Blueprint Equity, with participation from Villain Capital, Z21 Ventures and Bienville Capital, to grow its AI-native operating system for pediatric practices. The platform unifies clinical, billing and family engagement workflows beyond the traditional EMR, with the new capital going toward R&D and customer success as Develo expands across pediatric providers nationwide. - learn more
            LA Venture Funds
            • Kinship Ventures participated in Nectar Social’s $30M Series A, which was led by Menlo Ventures and its Anthology Fund, with participation from True Ventures and GV. Nectar Social is building an agentic social operating system for modern marketing, helping brands manage social intelligence, community engagement, creator workflows and conversational commerce across platforms like Meta, TikTok, LinkedIn, Reddit and X. The new funding will support engineering and applied AI hiring, deepen platform partnerships and expand Nectar Agent into more brand workflows. - learn more
            • Alexandria Venture Investments participated in CREATE Medicines’ $122M Series B, which was co-led by existing investors Newpath Partners, ARCH Venture Partners and Hatteras Venture Partners. The Cambridge-based biotech is developing in vivo CAR therapies for autoimmune disease and oncology using an mRNA-LNP platform that engineers immune cells directly inside the body, with the funding going toward advancing its CD19-targeted autoimmune program into the clinic, expanding its dual CAR CD19 x BCMA program and continuing work across its oncology pipeline. - learn more
            • Overture Ventures participated in GridCARE’s $64M Series A, which was led by Sutter Hill Ventures with backing from John Doerr, National Grid Partners, Future Energy Ventures, Emerson Collective, Stanford University and other existing investors. Redwood City-based GridCARE is building a physics-based AI platform that helps identify underused grid capacity and accelerate power delivery for AI data centers, compressing interconnection timelines from years to months. The company says it is already engaged in projects across more than a dozen markets representing more than 2 GW of new AI compute capacity. - learn more
            • Taste Tomorrow Ventures invested in Harken Sweets’ seed round, joining Selva and GRTSHT as the early-stage VC firm continues backing better-for-you snack brands. Founded by Katie Lefkowitz, Harken Sweets makes cleaner-label chocolate bars sweetened with whole-food dates instead of refined sugar or synthetic alternatives, and is already sold through retailers including Sprouts, Whole Foods, Kroger, Costco, Walmart, Albertsons and Wegmans. - learn more
            • Bonfire Ventures led Ranger AI’s $8.4M seed round, with participation from 25madison, Inovia Capital and Panache Ventures. Ranger AI is building an agentic revenue operations platform for industrial tendering, helping industrial, manufacturing and supply chain companies automate complex RFP, bid and project workflows. The company says its platform is already being used across more than 1,000 projects and can cut industrial tendering time by up to 50%. - learn more
            • Fika Ventures participated in Outmarket AI’s $17M Series A, which was led by Permanent Capital Ventures, with participation from SignalFire, TTV Capital, Dash Fund and senior insurance industry executives. Outmarket AI builds AI workflow software for insurance agencies and brokers, helping teams automate policy reviews, quote comparisons, renewals, coverage gap analysis, proposal building and other core workflows. The round brings the company’s total funding to $21.7M. - learn more
            • Wedbush Ventures participated in Secludy’s $4M seed round, which was led by Impression Ventures and also included LAUNCH, The Syndicate, Precursor Ventures, Hustle Fund, Script Capital, Mana Ventures and Chispa VC. San Francisco-based Secludy helps banks, payments firms and fintech companies safely use proprietary customer data to train and evaluate GenAI models by generating privacy-protected synthetic data, with the funding going toward hiring, go-to-market growth and expanding its platform across more enterprise AI workflows. - learn more
            • Sound Ventures led a new $17M funding round for Anomaly Insights, joined by Alumni Ventures and existing investors Link Ventures, Redesign Health and RRE Ventures. The New York-based company uses AI to help health systems analyze payer behavior, identify denials, underpayments and contract issues, and strengthen how providers engage with insurers across claims management and managed care negotiations. The new funding brings Anomaly’s total raised to $34M. - learn more
            • B Capital and UP.Partners participated in Havoc’s $100M Series A, backing the company’s push to scale its all-domain autonomous systems for defense operations. Havoc’s autonomy stack is designed to operate across air, sea and land platforms, and the new funding brings its total capital raised to nearly $200M as it expands deployment capacity, engineering and partnerships with defense manufacturers. - learn more
            • B Capital led Star Catcher’s oversubscribed $65M Series A, with the round co-led by Shield Capital and Cerberus Ventures. The Florida-based company is building what it calls the first power grid in space, using optical power beaming to deliver electricity on demand to satellites and other spacecraft, with the funding going toward orbital demonstrations, engineering and commercial expansion. The round brings Star Catcher’s total funding to $88M. - learn more
            • Interlagos participated in Cowboy Space Corporation’s $275M Series B, which was led by Index Ventures and valued the company at $2B. Formerly known as Aetherflux, the San Carlos-based company is building vertically integrated orbital infrastructure for the AI era, including low-Earth orbit satellites, purpose-built launch vehicles and in-orbit data centers designed to help meet rising demand for AI compute. - learn more

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