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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Your Bank Wants to Cancel Your Subscriptions

🔦 Spotlight

Hello, LA.

Somewhere between the streaming service you still use and the free trial you forgot to cancel, recurring payments have become a surprisingly complicated part of modern financial life.

Los Angeles-based ScribeUp believes your bank should help manage them.

The fintech company raised a $13M Series A led by Curql, with participation from Mucker Capital and Service Ventures. The financing includes $10M in equity and a $3M venture debt facility, bringing ScribeUp new capital to expand its team, accelerate sales and further develop its AI-powered bill-management technology.

The product is designed to live directly within the apps of banks, credit unions, fintechs and neobanks. Instead of simply showing customers that a recurring charge occurred, ScribeUp gives them tools to do something about it.

That could mean canceling a forgotten subscription, changing a payment method, accessing an advance or exploring refinancing options for an outside loan, all without leaving the financial institution’s app.

It sounds like a useful feature. It is also part of a much larger contest over who gets to manage the consumer’s financial life.

For years, banks have held customers’ money while third-party apps have increasingly helped them understand and manage it. Budgeting platforms organize spending. Subscription services identify recurring charges. Fintech apps recommend ways to save, borrow or invest.

Now AI assistants are beginning to combine those functions into a single interface capable of not only analyzing financial information, but acting on it.

That creates a risk for traditional financial institutions. If consumers begin turning to an outside app whenever they need to cancel a service, manage a bill or make a financial decision, their bank could become little more than the infrastructure beneath someone else’s customer experience.

ScribeUp offers banks a way to compete without building that technology themselves.

Its platform combines recurring-payment information with the financial context a bank already has, including balances, cash flow and payment timing. That allows a financial institution to do more than flag an upcoming charge. It can potentially recommend and execute an action based on the customer’s broader financial position.

ScribeUp says its technology is already used by more than 60 banks, credit unions, fintechs and neobanks. It can be added through an API, software development kit or embedded interface, allowing institutions to introduce bill-management features without creating the underlying infrastructure from scratch.

The new funding will support more advanced AI capabilities that can take action across different billers. That distinction matters. The first generation of personal finance software helped people see where their money was going. The next generation wants permission to do something about it.

For banks, the opportunity is straightforward: become more useful before another app takes their place.

For consumers, the appeal may be even simpler. Most people do not want another financial dashboard. They want the unwanted charge to stop.

The next battle in banking may not be over who holds your money.

It may be over who gets to press cancel.

More from this week’s LA startup and venture scene below.

🤝 Venture Deals

    LA Companies

    • International Dance League raised a $15M Series A led by Elysian Park Ventures, with participation from Sony, KB Partners, APEX, Yamaha Music Innovations Fund and October Ventures. Following a debut season that sold out all six events and generated 2B views, IDL will use the funding to expand its tour, strengthen team and dancer operations, improve broadcast production and develop new fan experiences for 2027. - learn more
    • Santa Fe Springs-based DrizzleX raised a $6.8M Series A-2 led by Israel Investment Fund Group, with several of the water-management platform’s own customers also investing. The company will use the funding to expand sales, streamline hardware manufacturing, build partnerships and develop new products that help property owners detect leaks, reduce water use and lower operating costs. - learn more
    • POV Beauty raised an undisclosed Series A led by Silas Capital, with participation from RÉDO Capital and existing investor Imaginary Ventures. The skin-prep brand will use the funding to build on its nationwide Sephora launch, expand its team and TikTok Shop presence, and develop more skincare-makeup hybrid products. - learn more

    LA Venture Funds
    • Chapter One participated in Warp Sciences’ $215M Series A, which was led by Lightspeed and included a large group of venture firms and angel investors. The company is building AI-powered, increasingly automated laboratories that will manufacture and test molecules for drug developers, aiming to accelerate preclinical research while expanding scientific infrastructure in the U.S. - learn more
    • Capital Group participated in Legora’s $550M Series E, which was led by Atreides Management and valued the legal AI company at $8.8B. Legora will use the funding to expand across the U.S. and international markets while developing new capabilities for its agentic operating system, which is used by more than 140,000 legal professionals. - learn more
    • Group 11 participated in CapitalOS’ $21.9M Series A, which was led by LGVP and included WEX Venture Capital, Great North Ventures and Night Capital. CapitalOS will use the funding to scale its infrastructure, which enables B2B software platforms to quickly offer financial products while outsourcing functions such as compliance, risk management and underwriting. - learn more
    • Starshot Capital participated in IMIO’s $12M funding round, which was led by Sofinnova Partners and included Chipotle’s Cultivate Next, Grow Together Salinas, Earth Foundry and Serra Ventures. The agricultural biotechnology company will use the capital to build a Chicago headquarters, laboratory and manufacturing facility for its freeze-dried microbial products, which are designed to improve soil health and crop yields. - learn more
    • SUM Ventures participated in Vectorial’s $3M seed round, which was co-led by Smilegate and SenseAI Ventures and included several investors connected to UC Berkeley and Stanford. The startup will use the funding to scale its AI-powered consumer research platform, which lets companies test products, marketing campaigns and AI agents against simulated audiences before launching them publicly. - learn more
    • Wave Function Ventures participated in Stellios Technologies’ oversubscribed $5M pre-seed round alongside Sofreh Capital, Cubit Capital, Mana Ventures, Atoms & Bits and other investors. The Austin-based company will use the funding to deliver its first high-power microwave systems, establish domestic research and manufacturing facilities, grow its team and advance technologies spanning directed energy, compact fusion and next-generation propulsion. - learn more
    • Upfront Ventures participated in Daytona’s $60M Series B, marking the Santa Monica firm’s third investment round with the company. Led by FirstMark Growth, the financing valued Daytona at $1B and will help the startup expand sales and engineering for its cloud infrastructure, which provides secure virtual computers where AI agents can execute tasks. - learn more
    • Core Innovation Capital participated in Delegance Brokerage’s $3.1M pre-seed round, which was led by Grit Capital Partners and included Gilgamesh Ventures and Outside VC. The AI-powered commercial insurance brokerage will use the funding to hire licensed brokers and engineers and expand partnerships as it promotes a flat 5% fee model in place of traditional commissions. - learn more
    • Core Innovation Capital participated in Prism Data’s $20M Series A, which was led by Story Ventures and included FINTOP Capital, Obvious Ventures, 1st & Main Growth Partners and Mana Ventures. Prism will use the funding to expand its cash-flow underwriting technology, AI infrastructure and data science team while growing across the U.S. and Canada and preparing for international expansion. - learn more

    LA Exits

    • Sanctuary has been acquired by WSG Brands, adding the contemporary women’s label to a portfolio that includes Von Dutch, Nasty Gal and Allbirds. The purchase price was not officially disclosed, though earlier documents placed it at $67M; WSG plans to expand Sanctuary internationally and into new categories, while founders Ken and Debra Polanco will remain involved. - learn more
    • SecureNet Solutions was acquired by CompassMSP, expanding the managed IT and cybersecurity provider’s presence on the West Coast. The deal gives SecureNet’s real estate, healthcare and professional services clients access to CompassMSP’s national cybersecurity, compliance and advisory resources while retaining their existing service team; financial terms were not disclosed. - learn more

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      Hello Sunshine Sold for More Than $900M. Now Reese Witherspoon Is Buying It Back.
      Image Source: Hello Sunshine

      🔦 Spotlight

      Hey there, LA.

      In Hollywood, every successful story eventually gets a sequel. This one brings Reese Witherspoon back to the company she built.

      Five years after selling control of Hello Sunshine in a deal worth more than $900M, Witherspoon is partnering with French production group Mediawan to buy back the Los Angeles media company.

      The reported purchase price is in the low-to-mid eight figures, significantly below Hello Sunshine’s valuation when Candle Media acquired a controlling stake in 2021.

      That difference tells a larger story than any single Hollywood transaction.

      Hello Sunshine was one of the most prominent acquisitions made during the streaming boom, when platforms were spending aggressively and investors placed enormous value on production companies with recognizable founders, established audiences and libraries of intellectual property.

      Witherspoon had built all three.

      Founded in 2016, Hello Sunshine developed its business around stories centered on women, producing projects including “Big Little Lies,” “The Morning Show,” “Little Fires Everywhere” and “Daisy Jones & The Six.” It also turned Reese’s Book Club into an influential audience and discovery platform that now reaches 6.2 million readers and drives approximately $900M in annual U.S. book sales, according to the company.

      By 2021, that combination of talent, intellectual property and direct audience access looked like the foundation of a next-generation media empire.

      Candle Media, backed by capital from Blackstone, acquired Hello Sunshine as part of a broader effort to assemble a portfolio of entertainment brands. The company also purchased businesses including Moonbug Entertainment, ATTN: and Faraway Road Productions.

      Then the streaming market changed.

      Entertainment companies became more disciplined about content spending. The race to accumulate subscribers gave way to pressure for profitability. Production budgets tightened, consolidation slowed and some of the valuations assigned during the streaming boom became difficult to maintain.

      Hello Sunshine’s return to founder-led ownership reflects how dramatically the media landscape has changed since 2021. It also gives Witherspoon an opportunity to regain greater influence over the company at a moment when its core assets may matter more than its former valuation suggests.

      Under the new ownership structure, Hello Sunshine plans to refocus on premium film and television, Reese’s Book Club and new storytelling and distribution formats. Mediawan brings an international production network, while Witherspoon brings something harder to manufacture: a trusted personal brand and an audience willing to follow her recommendations from books to screens.

      That relationship with consumers is increasingly valuable in a fragmented media market. Studios can finance productions. Streaming services can distribute them. Far fewer companies can reliably convince millions of people to care before a project is even released.

      For Los Angeles, the deal reflects the increasingly fluid boundary between entertainment company, consumer brand and technology-enabled audience platform. The most resilient media businesses may not be those producing the greatest volume of content, but those that own a direct relationship with a specific community.

      The first Hello Sunshine deal captured the optimism of the streaming era.

      The second may offer a more focused model for what comes next, with the company once again guided by the founder who understood its audience from the beginning.

      Hollywood loves a comeback story.

      This time, the company is making one too.

      LA Tech Week’s Final Stretch

      Still making the most of LA Tech Week? We have organized the remaining events by location to make planning the weekend a little easier:

      Event schedules may change, so confirm the latest details with the organizer before heading out.

      More from this week’s LA startup and venture scene below.

      🤝 Venture Deals

        LA Companies

        • Goodweek raised a $12M seed round led by Adara Ventures to expand its AI management platform for small and midsize businesses. The company brings tools such as ChatGPT, Claude, Gemini and Mistral into one governed workspace and will use the capital to accelerate sales and expand into Latin America and Asia. - learn more

        LA Venture Funds
        • Fika Ventures co-led Otter Health’s $8M seed round alongside Evidenced Capital, with participation from Slow Ventures, Metrodora, CoFound Partners, Patient Capital, SemperVirens and Layout Ventures. The startup will use the funding to scale its AI-powered platform, which helps healthcare payers and providers reduce unnecessary care and manage quality without relying as heavily on traditional prior authorization. - learn more
        • Nant Capital co-led Prolific Machines’ $50M Series B2 alongside Atoms & Bits, bringing the biotechnology company’s total funding to more than $100M. Prolific will use the capital to scale its light-controlled biomanufacturing platform, expand pharmaceutical and biotech programs and begin early work on tissue and organ fabrication. - learn more
        • Family Fund participated in Allara’s $30M funding round alongside new investors Camino Partners and Foreground Capital, while existing backers including Index Ventures and GV increased their commitments. The women’s healthcare company will use the capital to expand AI-enabled care, grow its provider and enterprise partnerships and advance research into hormonal, metabolic and reproductive conditions. - learn more
        • Vida Ventures participated in Soufflé Therapeutics’ oversubscribed $135M Series B, which was led by Juvia Group. The biotech will use the funding to move three lead programs into clinical trials for muscular dystrophy, heart failure and muscle and metabolic disorders while advancing its broader pipeline of targeted RNA therapies. - learn more
        • FJOR participated in LightSprint’s $6.1M seed round, which was led by 645 Ventures. The AI software platform will use the funding to expand its enterprise product and grow its engineering and go-to-market teams as it helps employees across departments make changes to company codebases while keeping engineers in control. - learn more
        • Muse Capital participated in Collective X Health’s oversubscribed $3.2M pre-seed round, which was co-led by Council Capital and Anthemis Female Innovators Lab Fund. The women’s health intelligence startup will use the funding to expand its female-focused research and data platform, meet growing enterprise demand and support new research aimed at closing the women’s health data gap. - learn more
        • Act One Ventures participated in Intake AI’s $2.5M pre-seed round, which was led by Kapor Capital. The startup is building AI agents that automate clinical-trial setup and operations, helping research teams turn protocols into documents, search study materials and transfer approved forms into existing systems. - learn more
        • M13 participated in Ultra’s $62M financing, which included a $50M Series A led by Framework Ventures. The Brooklyn-based robotics startup will use the capital to expand deployment of its AI-powered warehouse robots, which handle packing, sorting and other fulfillment tasks and have already processed more than 500,000 orders. - learn more

        LA Exits

        • Farcaster is being acquired by Balaji Srinivasan’s Network School from Neynar, marking the decentralized social network’s second change in ownership this year. The deal includes Farcaster’s app, protocol repositories and related products, with its new owner planning to introduce a rules-based “social smart contract” governing full participation on the platform; financial terms were not disclosed. - learn more
        • Creator Authority has been acquired by Billion Dollar Boy Group, bringing the agency’s B2B influencer marketing expertise and LinkedIn specialization into BDB’s global creator business. The deal will help Creator Authority scale its work with enterprise brands while strengthening BDB’s presence on the U.S. West Coast and expanding its B2B creator marketing capabilities; financial terms were not disclosed. - learn more
        • Burbank-based CareerArc was acquired by AI hiring platform Humanly, with financial terms undisclosed. The deal combines CareerArc’s recruitment marketing and social recruiting tools with Humanly’s AI-powered candidate engagement, screening and interviewing platform, creating a more connected system for employers managing high-volume hiring. - learn more
        • Ethiqly was acquired by Carnegie Learning from Owl Ventures and the company’s management, with financial terms undisclosed. Carnegie Learning plans to integrate Ethiqly’s AI-powered writing platform into its literacy offerings, helping students improve their writing while giving teachers greater visibility into the drafting, revision and learning process. - learn more

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          How to Navigate LA Tech Week 2026

          🔦 Spotlight

          Happy Friday, Los Angeles.

          Next week, hundreds of tech events will take over the city, bringing founders, investors, engineers and creators together from October 12 through 18.

          Calling LA Tech Week a conference does not quite capture the experience.

          Presented by Andreessen Horowitz, Tech Week is a decentralized collection of panels, workshops, demonstrations and gatherings hosted independently by startups, venture firms and technology companies. There is no convention center or central stage. The programming stretches from Santa Monica and Venice to Culver City, Downtown, El Segundo and beyond.

          In other words, the city is the venue.

          AI remains the dominant theme for 2026, appearing across enterprise software, healthcare, finance, media and the creator economy. The schedule also reflects industries where Los Angeles has built a particular advantage, including aerospace, defense, robotics, advanced manufacturing, entertainment and consumer technology.

          That range is what makes LA Tech Week distinct. It brings together the software companies shaping what comes next with the industries that already define Southern California.

          The challenge is deciding where to show up.

          Our advice: apply early and organize your schedule by neighborhood. Crossing from Santa Monica to Downtown may look manageable on a calendar created by someone who has never driven in Los Angeles.

          To help you spend more time meeting people and less time crossing the city, we have organized each day’s events by location:

          You can also browse the complete official LA Tech Week calendar.

          Plan carefully, but do not fill every minute. The best conversation of the week may be the one that was never on your calendar.

          More from this week’s LA startup and venture scene below.

          🤝 Venture Deals

            LA Companies

            • El Segundo-based Gallatin AI raised a $50M Series A from new and existing investors including 8VC and Silent Ventures, bringing its total funding to $70M. The defense technology startup will expand its engineering team and advance Navigator, an AI platform that helps U.S. military units coordinate vehicle readiness, supplies, medical logistics and other mission-support operations. - learn more
            • Pasadena-based quantum computing startup Oratomic raised a $475M Series B at a $5.4B valuation, just three months after its Series A. ARCH Venture Partners, Spark Capital, Khosla Ventures, Index Ventures, General Catalyst and Bezos Expeditions co-led the round, bringing Oratomic’s total funding to $775M as it works toward a commercially viable, fault-tolerant quantum computer by 2030. - learn more
            • Torrance-based Fortastra raised a $30M Series A led by First In, with participation from Upfront Ventures, Space Capital, Rsquared, Side Door Ventures, ATX Ventures and existing investors. The company will use the capital to develop its next-generation maneuverable spacecraft, expand its engineering and operations teams and scale production of systems designed to protect critical assets in orbit. - learn more
            • Parallel Systems raised a $100M Series C led by AVP, with participation from Hillspire, Agility Global, Cobalt Capital, Anthos Capital, Congruent Ventures, Riot Ventures and Collaborative Fund. Founded by former SpaceX engineers, the company will use the funding to scale production and commercial deployment of its autonomous, battery-electric Panther rail vehicles, which are designed to make short-haul freight more competitive with trucking. - learn more
            • Gaming studio Gardens Interactive secured more than $35M in a Series B led by Lightspeed, with participation from Sequoia Capital, Index Ventures, Accel, Innovation Endeavors, Zenith Capital and other investors. The company will use the funding to launch and operate its debut social role-playing “strandbox” game, an evolving multiplayer world shaped by players’ actions and interactions. - learn more
            • Outer Spaces raised an $8M pre-seed round led by Upfront Ventures, with participation from Unlock Venture Partners, Mucker Capital and Genius Ventures. The startup is developing outdoor furnishings with integrated solar panels and batteries, turning backyards into sources of clean energy and backup power. - learn more
            • Furientis raised a $25M seed round led by Benchmark at a reported $125M valuation, following a $5M pre-seed announced in May. The defense startup will use the capital to scale production of lower-cost missile interceptors designed to be assembled quickly with readily available components, with a long-term goal of producing 1,000 systems annually at each factory. - learn more
            • Hiyo raised a $20.8M Series B led by Constellation Brands, with returning investor Live Nation also participating. The nonalcoholic beverage company will use the funding to expand its adaptogen- and nootropic-infused social tonics across more than 13,000 retail locations while growing its presence at hospitality venues and live events. - learn more
            LA Venture Funds
            • Navitas Capital participated in Vesta’s $30M Series B, which was led by Conversion Capital and included backing from several major mortgage lenders and financial institutions. The company will use the funding to scale its AI agents across mortgage origination, automating tasks such as application reviews, underwriting decisions and closing-document checks. - learn more
            • MTech Capital led Nettle’s oversubscribed $4.8M seed round, with participation from Project A Ventures, Sure Valley Ventures, Portfolio Ventures and Ventures Together. The insurtech startup will use the funding to expand across the U.S. and Europe while growing its AI platform, which helps commercial insurers identify property risks, accelerate inspections and generate reports. - learn more
            • Bonfire Ventures doubled down on Santé by participating in the company’s $15M Series A, which was led by FINTOP and included other returning investors. The New York startup will use the funding to expand its AI-powered operating system for independent wine and liquor stores, which combines point-of-sale, e-commerce, payments, inventory and marketing tools in one platform. - learn more

            LA Exits

            • Winnow Solutions was acquired by Marina del Rey-based Spring Labs, with financial terms undisclosed. Winnow’s attorney-built library of more than 100,000 state and federal regulatory requirements will become a core part of SpringGRC, helping financial institutions connect changing laws directly to their compliance policies, controls and workflows. - learn more

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