In the summer of 1996, I thought I was ahead of the curve.

I was college-bound and landed an internship at IBM’s headquarters in Paris. Other than earning my first paycheck ever, what excited me most was the opportunity to be immersed in the tech world on the eve of the dot-com boom.

It was picks and shovels time. At my desk, I had a Pentium Pro running OS/2, a 17-inch SVGA CRT for building slideshows in Freelance Graphics, and a copy of Ed Tittel’s HTML for Dummies to teach myself to build websites in my spare time. At meetings, IBM execs took notes on sleek ThinkPad laptops with butterfly keyboards. CEO Lou Gertsner himself paid us a visit on campus to extol the virtues of our new mainframe lineup and how they would power the upcoming Olympic Games in Atlanta. I nodded knowingly. The team I supported was responsible for driving our top EMEA customers to attend, and I must have stuffed hundreds of AS/400-branded keychains, along with other themed tchotchkes, into goodie bags meant to sway them.

I was in the zone: learning from the best, at one of the world’s most prestigious companies, and already thinking about how I’d apply these skills in college to keep my streak of teenage Indian overachievement going 😉.

Poster boy

Then I started hearing about this other boy, Sabeer Bhatia.

Not from the news. Not from the internet — it was still too early for that. But through the way you heard everything in a South Asian household in the 1990s: the aunties. Overheard phone calls. Dinner party conversations. My mother’s voice, rising over the din, exclaiming with the same blend of awe and competitive appraisal whenever she brought up the topic: “Can you imagine? Indian boy… only twenty-seven years old. He goes to Stanford, studies engineering, and then builds this computer thing, and now everyone is talking about it!”

That computer thing? That was Hotmail, one of the world’s first free browser-based email services. Within weeks of its launch, it went viral, spreading online just as quickly as the news of the Indian boy who built something from nothing spread through the global auntie network.

What none of the aunties fully appreciated — what almost nobody outside of Silicon Valley understood at the time — was that Bhatia hadn’t just built a killer service. He’d invented an entirely new way of marketing one. And three decades later, every product that grows by attaching its name to your workflow is still running his play.

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Before Hotmail, Email Was a Walled Garden

In 1996, only about 20 million American adults had access to the internet at all — roughly the same population as Florida. Netscape Navigator, then commanding nearly 80% of the browser market, had only gone public the year before. The web was still a novelty. Most households weren’t on it. And if you were on it, having an email address wasn’t something that traveled with you.

Yes, email existed, but it was tethered. You had an address through your employer, your university, or your ISP, and the moment you left any of those, that address went with it.

Accessing email required a dedicated desktop client. Eudora, the most popular of its era, had a devoted following among power users, but cost up to $65 for the full version and required configuration on a specific server on a specific machine. Microsoft’s Outlook and Lotus Notes were enterprise products bundled into their respective suite.

Bhatia met co-founder Jack Smith while working at Firepower Systems, after an earlier stint at Apple. They had initially planned to build a web-based database where you could store anything — files, pictures, documents — and retrieve it from anywhere. The pivot to Hotmail was almost accidental and came from hitting a mundane wall at their day jobs. Corporate firewalls were blocking their personal email accounts.

“That’s when the idea of making email available on the web came to us. It was as simple as that. We said, wow, we could access our email from anywhere in the world. That was the genesis of Hotmail. And that’s why it’s called Hotmail — HTML mail.”

No configuration. No ISP tie-in. No desk. No institution. Just a username, a password, and a 2MB inbox waiting for you from any connected computer on earth.

They launched on July 4, 1996. Independence Day. A choice that was equal parts symbolic and on-the-nose. Freedom from ISP-bound email. With $300,000 in seed funding from Draper Fisher Jurvetson, two founders, and a prayer, Hotmail opened its doors to the public.

“Just Put It on Every Email”

For the first few months, growth was real but measured. Bhatia was thinking of billboards, radio spots, aka the standard playbook for getting the word out. Then Tim Draper — DFJ’s founder — sat down with the team and asked the question that changed everything.

“Can’t you just give it out to all those guys on the web?”

“That would be spamming”, Smith replied.

Draper, who’d never heard the term before, thought for a moment, then landed somewhere else. He’d recalled a Harvard Business School case study about women holding Tupperware parties — selling to friends, who then sold to their own friends. What if every Hotmail user’s outgoing email became a silent referral by embedding a simple tagline in the footer? He originally suggested “P.S. I love you. Get your free email at Hotmail.” The team resisted at first, but eventually settled for something simpler: “Get your free email at Hotmail.com.”

Six words. No advertising budget. And within hours of flipping the switch, the growth went up and to the right.

Making aunties proud

Within six months, Hotmail had 1 million users. Five weeks after that, 2 million. At its peak, the service was adding 60,000 new accounts every single day — on an internet that still only had tens of millions of users worldwide.

By December 1997, just eighteen months after launch, Hotmail had 8.5 million active accounts (some sources say up to 12 million by early 1998). That made it one of the largest services on the entire internet at the time. That’s also when Microsoft came in and acquired the company for $400 million in stock, making it the largest internet startup deal of its time.

The mechanic itself was dead simple: every email sent through Hotmail was simultaneously an advertisement for the service. You didn’t need to convince anyone to try it. They just had to receive an email from you, someone they trust. This made every user, whether they realized it or not, into a salesperson. Every inbox message composed in Hotmail was an invitation to try the product for free.

It was one of the world’s first examples of viral marketing, but nobody was calling it that yet. The term, borrowed from epidemiology, would come later. But Bhatia had built the virus before anyone named the disease.

Most Remarketable: The Growth Loop That Keeps On Giving

Before Hotmail launched in 1996, social proof meant a logo wall, an endorsement, a case study, a press release. After Hotmail, it could be as simple as six words at the bottom of a colleague’s email or four words attached to a meeting invite. Bhatia and the Hotmail team showed that social proof could be ambient — not a marketing asset you produced, but a byproduct of the product experience itself.

The lineage is direct and traceable. Research in Motion, the company behind BlackBerry, baked “Sent from my BlackBerry” into its default email signature, and enterprise executives happily kept it as a badge of honor. Apple followed with “Sent from my iPhone,” which became arguably the most-read six words in the history of mobile.

When I led ISV Marketing at Salesforce, we built a similar loop into Chatter, the CRM’s built-in social feed, to evangelize partner wins. Every time a partner-sourced deal closed, the rep who owned the account got a public @mention notifying them of the quota relief they received courtesy of that partner. And because account executives followed one another, it spread across the sales org within weeks. The inspo was Bhatia’s logic, even if none of us called it that.

Fast-forward to today and Calendly appends “Scheduling powered by Calendly” to every meeting invite its users send. Notion drops its watermark on every shared page.

But the pattern is always the same: discreetly plug the product at the moment of use, and let network effects do the rest.

Least Remarketable: When the badge does not belong

But here’s the insight that separates the products that ran Bhatia’s play successfully from the dozens that tried to copy the mechanic without copying the logic: the tagline only lands if it’s native to the workflow, not tacked onto it.

Hotmail’s footer worked because it was organic. It lived inside the email itself — the very thing people were already paying attention to. It didn’t redirect you. It didn’t ask for your time. It arrived in context, carried by trust, and cost nothing to deliver. The same is true for “Sent from my Blackberry.” You didn’t see it on a billboard. You saw it at the bottom of a message from your boss, your co-worker, or your client. Calendly’s link appears in the meeting invite you were going to send anyway. In each case, the tagline is native to the action. It doesn’t interrupt it. It doesn’t redirect from it. It just flows.

Contrast that with some of the recent viral mechanics that feel bolted on. “Powered by Shopify” at the bottom of an e-commerce storefront — one of the most Googled phrases in web design is how to remove it. “Made with Lovable” — same story. When the badge feels like free advertising foisted on users rather than a natural artifact of their activity, the user’s first instinct isn’t to share it — it’s to figure out how to get rid of it, with some even willing to pay for removing the badge.

P.S. I love you

Does your product carry your message when it travels?

Not your ad. Not your landing page. The product itself.

When someone uses your tool, shares their work, or sends something through your platform, does that act make your next potential customer curious about your product? Does it make them want in?

Right now, AI startups are locked in a specs war — benchmarks, token counts, context windows — while users hop between models because they all feel interchangeable.

Hotmail made its inroads with none of that. No feature comparison. No benchmark bragging. Just six words at the bottom of something people were already sending and finding useful, promising you the same experience.

Draper’s original line — “P.S. I love you” — never made it onto the product. But in a way, it’s exactly what millions of people were saying, without realizing it, every time they hit send.

To say I was pumped about F1: The Movie coming out this summer would be an understatement. I grew up watching Formula 1 back in France, starting with the Prost-Senna era. As a movie buff, I also knew that having Joseph Kosinski direct, and Brad Pitt star as the aging pro mentoring the young hotshot, basically meant we were going to get Top Gun: Maverick on wheels. Add in Sir Lewis Hamilton (7-time F1 world champion and 🐐) as a producer for good measure, and it was, to channel F1 commentator David Croft, “lights out and away we go” to the closest multiplex on opening day.

By the time the title credits started rolling and Hans Zimmer’s F1 theme kicked in at the 12m30s mark, I was locked in.

• That wideshot of Silverstone... perfection. 👌🏽

• “Apple Originals Films Presents”... our boy Tim Apple is cooking with this one.

• “A Jerry Bruckheimer Production”... let’s go! 🚀

• The camera pans to our first look at the gorgeous APXGP car... As it zooms in, the whine of the F1 engine grows, and that’s when the drum snare kicks in... chef’s kiss. 👨🏽‍🍳💋

• The tracking shot follows the car as it hurtles through a straight, to reveal:

• “Expensify/A Joseph Kosinsky film”... Wait... What?

Ok, so that’s not what was actually on screen... but for a beat, it’s all I could see: Expensify’s logo directly under the director’s name and taking up way more visual space. As the saying goes, you can take the man out of B2B marketing (and to the movies), but you can’t take B2B marketing out of the man.

Expensify. The expense management software? Really? I was floored... then impressed. By the time the title sequence ended, I’d counted 20+ more Expensify logo hits. These were full-view impressions of their brand on the driver’s helmet, the car’s sidepods, rear wing, and halo, as well as on the race suit and team shirts of everyone from the fictitious APXGP racing team. Factoring in the movie’s global audience of 12M+ during its opening weekend, that was over 240M total impressions of Expensify’s brand served up on a global stage in the first 160 seconds alone!

In what is on track to be the highest-grossing sports movie of all time ($632M globally at the box office), about an elite sport that attracts over a billion dollars in annual brand sponsorships to reach a coveted audience of 800M global fans, Expensify managed to place itself front and center. The kicker? Unlike typical product placement, theirs felt organic throughout because, like in real F1, they were APXGP’s title sponsor.

The marketer in me had one burning question: How did they pull this off, and more importantly, why didn’t anyone else think of it first?

Applying the perfect undercut

Sponsoring Formula 1 is not cheap. Companies pay on average $50M to be team title sponsors. It’s estimated that Oracle pays over $90M a year to sponsor Red Bull Racing, one of the sport’s leading teams. The signal-to-noise ratio is also challenging from an ROI perspective. In any given race, viewers are bombarded with hundreds of logos, yet only get a fleeting glance at most of them. According to Nielsen Sports, 58% of F1 fans can’t recall more than two sponsors on a given car.

I would know. I led product marketing at WeWork when we considered sponsoring F1 in 2019. It was a sensible play at the time, given the hypergrowth and hyperawareness we were experiencing. Netflix’s Drive to Survive had just debuted and was already garnering buzz. We also knew the sport appealed to the global mix of ambitious startup founders and incumbents looking to up their cool factor, which was at the heart of our marketing. We had executive support, and so the only matter before us was which car and team to sponsor... that is, of course, until we famously ran out of money.

It was a bummer in more ways than one, believe me, because WeWork would have clearly stood out in a field of sponsors dominated by automotive, oil, gas, tire, and logistics brands (~50% of sponsorships in 2019). Critically, we would also have staked our claim early in a sport about to take the world by storm. It wouldn’t just have been a bold brand play, but—to use an F1 analogy—the perfect marketing undercut.

In F1, an undercut is a pit-stop strategy in which the chasing car pits earlier than the car ahead, aiming to leapfrog it after both cars stop. So while your rival stays out on their current racing strategy, you make an early move they don’t see coming, like pitting for different tires or less fuel. You then go and try to set faster laps to gain an advantage. By the time your rival reacts and pits, you’ve won track position.

Taking the undercut comes in handy in races where overtaking is difficult, or when you know you have a competitive car that can take on rivals if given the chance. Swap out the terms “races”, “overtaking”, and “car” with “markets”, “attaining awareness”, and “product” in the previous sentence, and you can see why executing an undercut is also valuable in marketing.

But here’s the thing: in both cases, you have to commit to the undercut before you know it will work. Success requires accepting uncertainty. And while we didn’t get to execute our undercut at WeWork with a real-life F1 team, watching Expensify execute theirs—with a fictional team, no less—made it clear they were ready to take exactly that kind of bet. It’s that appetite for risk that makes it a remarketable, because it’s what separates great marketing from safe marketing.

Built for combat

Midway through the movie, Brad Pitt tells his lead engineer, played by Kerry Condon, “We need to build our car for combat,” because he realizes APXGP has to fight their competition where they least expect it: in the turns.

By mid-2022, Expensify and its CFO, Ryan Schaffer, were facing a combat situation of their own. The company had IPOed a year earlier but saw its market cap decline by 72% to $788M and a slowdown in revenue growth.

Headwinds came from two directions. At the macro level, the entire SaaS economy was in free fall due to rising interest rates. Tech was about to enter a nuclear winter of layoffs and belt-tightening, putting Expensify’s seat growth and customer activity at risk. Competition was also stiffening. TripActions (soon to rebrand to Navan) had just raised another $300M for their Series G—pushing their valuation to $9.2B—and were aggressively expanding into expense management. Meanwhile, SAP Concur remained the dominant incumbent in the enterprise space, with 85M users and deep pockets.

Expensify needed to take a big swing. Luckily, they knew how.

In 2019, the company spent $15 million on Super Bowl advertising, including a 30-second spot featuring rapper 2 Chainz, actor Adam Scott, and a $200K ice-sculpted Lamborghini. The commercial went viral, generating $62 million in earned media, a 1,000% spike in sign-ups, and even spawning a music video that reached #1 on Vevo’s US Hip-Hop chart.

This unorthodox approach of wanting to be “part of the culture” came from Expensify’s leadership team, including Schaffer. Because Expensify sells, in his words, “business software to consumers who sell us to their boss”, orchestrating big brand moments that fuel water-cooler talk was worth it. The Super Bowl worked because it’s the one time of the year people want to see an ad, and their spot earned them a knock-on awareness effect that lasted the next 9 months.

But for this next move, Schaffer and the executive team wanted to swing for the fences. They also wanted a unique way to reach more people worldwide, including decision-makers. They briefed their agency partner, Alto, on targeting “something on the scale of the Super Bowl but not the Super Bowl again”.

“We can’t if we don’t try.”

Together with Alto’s Chief Creative Officer, Hannes Ciatti, they explored entertainment partnerships, including scripted shows and original content, where Expensify could be woven into popular culture. But it was only when they heard that Apple was seeking $40M in partner sponsorships for its upcoming F1-themed movie that the opportunity to make a splash came into focus.

F1 was now mainstream, and some of the world’s biggest brands, including enterprise SaaS companies, flocked to sponsor it. Strangely enough, none of them competed with Expensify. At a time when every SaaS company was entering cost-cutting mode, the opportunity to become the title sponsor of a fictional F1 team, at a fraction of what it cost in the real world, wasn’t just contrarian. It was a calculated risk, but one that could yield dividends. They took the undercut.

It’s estimated that Expensify committed $10-20 million—roughly 6-12% of their annual revenue at the time—to sponsor the fictional APXGP F1 team, something for which there was no precedent. Payments were to be made over multiple years, but when the expense hit their books in early 2025, Expensify admitted on an earnings call that they were bullish about what could be “one of the best brand placement opportunities ever.”

The movie opened on June 27, 2025.

Snagging the pole

The numbers were staggering. According to brand tracking firm Concave, Expensify secured over $100 million in earned media value from the theatrical run alone. At the Met Gala, co-star Damson Idris wore his APXGP race suit on the red carpet a month before the film’s release, sparking millions of impressions and a 4X spike in sign-ups in a single night.

Expensify also benefited from a multiplier effect as APXGP’s title sponsor, the same way real sponsors would, and then some. Any marketing, tie-in, or companion media that featured elements of the car, team, or the cast in costume gave Expensify an added impression they didn’t pay for. Apple heavily promoted the movie across multiple channels. Expensify was in the Don Toliver/Doja Cat music video for “Lose My Mind”. Heineken ran a spot featuring Pitt and Idris sipping beers in their uniform—they never spoke to Expensify about it.

But that was the bet, wasn’t it? Shortly after the movie’s debut, Schaffer said in an interview, “We didn’t know this was going to happen, but we hypothesized that it would.”

By Q2 2025 earnings, Expensify reported a 50% increase in overall brand awareness, with a 350% surge among 18 to 24-year-olds. The film didn’t just perform at the box office; it also earned plaudits for everyone involved. It is now Brad Pitt’s highest-grossing film as a leading man. It is nominated for four Academy Awards, including Best Picture, and months after its theatrical run, it became the most-streamed movie on Apple TV+.

Compare that to Expensify’s Super Bowl campaign results. For the same spend, the F1 movie nearly doubled earned media value and delivered 35+ minutes of integrated screen time, compared with a single 30-second spot that typically competes with 50+ other advertisers for attention.

Or compare it to festival sponsorships like Cannes, where brands like Pinterest, Spotify, and Meta pay for activations that generate $10–30M in media impact value, but compete for visibility against dozens of other sponsors without the title dominance Expensify secured.

But here's the real difference: those activations are ephemeral. A Super Bowl ad lives and dies in 30 seconds. A festival sponsorship lasts a weekend. This film will stream indefinitely on Apple TV+. Every rewatch, every "I love this part" recommendation, every viewing party years from now delivers another brand impression Expensify doesn't have to pay for again.

By betting on F1: The Movie, Expensify didn’t just evolve their playbook. They got dibs on a less crowded battlefield that offered better positioning and more surface area for their brand to shine.

Most Remarketable: What brands and startups can take away from Expensify’s playbook

The Asymmetry Play

Expensify understood early on that a big and contrarian swing can pay dividends. Their Super Bowl ad back in 2019 stood out for all the right reasons. Committing 6-10% of their revenue on F1 took cojones, but in a market where everyone’s optimizing for the same thing, asymmetry beats efficiency.

In late 2022/early 2023, when better-capitalized competitors were cutting costs, Expensify bet big on a cultural moment nobody else saw coming. You can bet that even Apple and the filmmakers had the jitters on whether the movie would perform. But that’s the thing with asymmetric bets: the risks are real, and you have to commit before you know they will work. But the upside can pay dividends: if it lands, you own the race story or, in this case, the marketing narrative, while leaving your competitors in the dust.

Buying Track Position When Others Won’t

In intensely competitive markets, risk-taking isn’t reckless—it’s strategic. Done right, it’s a unique chance to seize and frame the narrative at your competitor’s expense or to capitalize on their absence or silence.

Anthropic’s preview of their Super Bowl ads this week, which were feral and thinly-veiled takedowns of OpenAI’s decision to bring ads into their product, wasn’t just timed right; it was a calculated risk that earned them track position/awareness ahead of OpenAI airing their creative at the Super Bowl this week. A classic undercut.

Least Remarketable: Pitfalls to Avoid

An outcome that’s out of your control

For all its success, the reality is that Expensify’s strategy was 100% dependent on exogenous variables. The movie had to be great. Critics had to love it. Audiences had to show up on opening weekend. Brad Pitt’s star power still had to matter. Expensify controlled none of that, and that was always the inherent risk of an undercut strategy. If F1 had bombed, the play would have been a write-off, and we wouldn’t still be talking about it, except maybe on Reddit F1 channels.

The Conversion Lag

As of this writing, Expensify’s Q4 earnings have yet to be shared. Yes, the movie delivered spectacular awareness metrics, but did that convert into new paying customers? Back in June of last year, Schaffer told Sports Business Journal, “ultimately, we want this to turn into revenue. The jury is still out on that.”

That’s not an easy thing to admit in the open as an executive, let alone tell your board, given the spend. But here’s what Expensify did to mitigate this, which other brands taking similar bets can do as well. They learned from the Super Bowl campaign that a spike in sign-ups required retooling behind the scenes with their marketing team to better exploit and manage the less-than-MQL-ish quality leads. Faced with the potential for millions of sign-ups coming from the movie, they completely redid their sign-up flow and user education. Conversion may still be probabilistic, but qualification is deterministic.

“Create your own breaks.”

I’d be remiss if I didn’t come back to my original question: why didn’t anyone else jump on this opportunity the way Expensify did?

We may never know. But it’s more than likely that Apple shopped more than just one brand. I could count on one hand the number of enterprise SaaS players for whom this would have/should have been a no-brainer.

The answer isn’t a lack of creativity. It’s an appetite for risk. When you have $9.2 billion in valuation like Navan, or 85 million users like SAP Concur with decades of enterprise dominance, the last thing you do during a market downturn is bet 6-12% of revenue on a fictional racing team in a movie that might flop. You optimize. You cut costs. You wait for the market to stabilize.

As for the brands in other categories that passed on F1, whether for risk aversion, brand value reasons, or simply not seeing the opportunity, they didn’t just avoid a risky bet. They handed Expensify an uncontested lane to gain awareness, cultural relevance, and strategic positioning while everyone else went dark.

Expensify’s F1 bet is a remarketable not because it worked—though the early awareness numbers suggest it might—but because the company was willing to accept uncertainty when their competitors were not. Sometimes the most valuable marketing insight isn’t about creativity or execution. It’s knowing when the race has changed, and having the courage to bet accordingly.

The draw? He had recently moved into his own place and had just picked up an Xbox, Microsoft’s first-ever gaming console, which launched the week before. He also couldn’t stop gushing over a new first-person shooter (FPS) game called “Halo: Combat Evolved”, an Xbox exclusive.

As a longtime PC gamer and FPS player—nerd alert 🤓—I had my reservations about how the genre would translate to consoles. Nonetheless, I drove down a snow-plowed I-90 on that Wednesday and picked up two six-packs of Coors Light on my way up to his apartment.

What happened next will be forever etched in my memory: three days and quasi-all-nighters in which we beat the game’s campaign in split-screen co-op mode, the two of us glued to the visceral experience of defeating an unstoppable horde of aliens, in a race against time to unlock a mysterious galactic artifact.

It felt like we starred in our own Hollywood blockbuster. The whole thing was presented in category-defining high-definition graphics, immersive 5.1 surround sound, and intuitive controller mechanics that put us in the shoes of a space marine — scratch that, the Spartan supersoldier: Master Chief.

I was sold. When I got back home, I went straight to the Virgin Megastore on the corner of Newbury Street and Mass Ave and plunked down my cold, hard cash to buy my own Xbox and copy of Halo. I’ve owned every generation of the console ever since.

The power of a killer app

By launching Xbox with Halo, Microsoft delivered something unique for its time: a cinematic gaming experience, perfectly showcased by a title that took full advantage of the console’s power out of the box.

Halo became one of the most successful launch titles in console history, boasting a 50% attach rate on every Xbox and 6 million units sold over its lifetime. It also helped Microsoft officially enter, expand, and redefine the gaming market over several years, despite many believing it would fail.

Today, it’s a launch moment that stands the test of time because it encapsulates what every new product, platform, or service requires for a successful marketing debut: a killer app—the one experience so good that it makes buying into an entire platform worthwhile.

In a competitive market, Halo proved that the Xbox wasn’t just viable out of the gate but also ushered in something differentiated and possibly better for the console industry.

That’s what makes it an all-time killer app. That’s what makes it remarketable.

At a time when AI-led innovations are taking the world by storm and market expectations are at an all-time high, the need for vendors, large and small, to differentiate themselves through similar and tangible use cases has never been more critical.

So let’s rewind the clock and revisit what made Halo a shining example of the above, and how we can apply the lessons from Microsoft’s playbook today

The state of play in 2001

In the fall of 2001, you’d be excused if you thought Sony had already run away with the gaming console market. The PlayStation 2, launched a year earlier, had sold over 20 million units and offered hundreds of games.

Nintendo launched the GameCube, its next-generation console, three days after the Xbox, but it had decades of brand loyalty and a beloved catalog of characters and franchises at the ready.

Microsoft? A noob by comparison. Yes, the software giant had published a few PC games over the years (e.g., Flight Simulator and Age of Empires), but had little to no console experience.

The stakes couldn’t be higher, however. Microsoft’s original mission -- “a computer on every desk and in every home” was essentially complete. But as the home theater equipment market took off, fueled by the explosive demand for DVDs, which had grown 284% over the past two years, it was clear that the living room was the next frontier.

Sony knew this. Each PlayStation 2 came with a built-in DVD player, a format the Japanese multinational had heavily championed. The race was on: whoever dominated the living room would dominate digital entertainment for the next generation.

The Xbox team, led by Ed Fries, needed to make a statement.

“I need a weapon” - Master Chief

Hardware wasn’t going to be the issue. The original Xbox was essentially a bargain-priced gaming PC in a box. Microsoft knew how to build those and had extensive experience with controllers and peripherals from its PC gaming foothold.

Software also seemed straightforward. Unlike PlayStation’s custom platform, Xbox’s development software leveraged DirectX, a familiar standard for PC developers (ever wonder where the X in “XBox” came from 😉?). Having publishers port their games to the Xbox should be easy enough, in theory.

But ‘should be’ and ‘is’ are different things. Why would publishers invest in an unproven console platform?

Microsoft needed to demonstrate its vision would work. It needed proof that it could earn a space on every TV stand in every home. It needed a killer app.

Enter Bungie Software.

Bungie was a ten-year-old independent game studio founded by two University of Chicago students, Jason Jones and Alex Seropian. It found a niche following in the early 90s through technically impressive games made primarily for the Macintosh, such as the Myth and Marathon series (the latter influencing many of the gameplay mechanics and design philosophy seen in Halo).

By 1999, however, the studio was in financial trouble after a recall of Myth II and was looking for a buyer before it ran out of money. Halo was in development and had actually been previewed on stage at Macworld that summer by Steve Jobs himself.

The clock was also ticking for the Xbox team. They needed a solid library of games by Christmas 2001. When a Bungie executive approached Fries about a potential sale after the Macworld announcement, it wasn’t just serendipitous; it was the Hail Mary the Xbox team needed.

Bungie agreed to be acquired by Microsoft for $30M, with Halo slated to become a first-party console exclusive. The rest, as they say, is gaming history.

Game of the Year

Halo garnered massive praise at launch. In addition to its groundbreaking graphics and cinematic presentation, it was hailed for successfully bringing the FPS genre to consoles in a big way. The game’s positive word of mouth, multiple Game of the Year awards, and long-tail sales through 2002 made it not just a system seller for Xbox, but the system seller. It was the reason consumers bought the Xbox.

Halo did the three things killer apps do remarkably well: it set a new standard, delivered a breakthrough user experience, and offered a glimpse of the future.

Setting a new standard

Until Halo, most FPS games were played on PCs because of the standard mouse-and-keyboard controller scheme, which gave players confidence in their ability to move and aim with precision. While console FPSes did exist, some with even a cult following like GoldenEye 007, they were plagued by awkward controls.

Bungie addressed this by making full use of the Xbox controller’s mapping and ergonomics at launch: left thumbstick for movement, right thumbstick for aiming, triggers for firing, and face buttons for actions like jumping, reloading, and switching weapons. Sounds simple, right? But here’s where they really broke the mold.

• Bungie designer Jaime Griesemer engineered what they called “sticky aim”, an invisible layer of input interpretation that made thumbstick aiming and movement feel as precise as a mouse and keyboard.

• They also ensured that Halo’s action felt seamless through a new integrated combat system. For the first time in an FPS, players could lob grenades while keeping their weapon up, or melee enemies without holstering, or jump out of moving vehicles.

Put together, Halo combined precise player movement and combat actions into a fluid moveset and layout that became the standard for every major console shooter ever since.

Delivering a breakthrough user experience

It’s not an exaggeration to say that playing Halo felt like being dropped into one’s very own Hollywood blockbuster.

The final release of the game dripped with production values.

From the iconic Gregorian chant that guided you through the load menu and punctuated other epic moments in the game, which game composer Marty O’Donnell wrote it in three days, to the magnificently rendered 3-D environments that made it feel like you were interacting with a massive open world for which the game won many DICE awards (think gaming’s Oscars), to the tactile feedback you’d get via the controller each time you’d fire a weapon or sustain damage--all of these elements made for an elevated and differentiated user experience, powered by the Xbox.

Years later, Hideo Kojima, the revered game auteur and producer who worked on flagship titles for Sony such as the Metal Gear Solid series, would credit Halo as one of the releases that sparked a significant shift in what big-budget games could look and feel like in the early aughts.

Offering a glimpse of the future

Last but not least, Halo offered a compelling glimpse at what the future of online gaming could look like from the comfort of one’s couch.

It started with Microsoft’s bet to be the only manufacturer to ship its console with a built-in 10/1000 Ethernet port, enabling console-to-console play via local area networks (LAN) and future-proofing it for online gameplay via broadband.

It was a gutsy move because high-speed internet had yet to take off in most households, but it was also prescient.

Halo supported competitive multiplayer gameplay for up to 16 players by connecting up to 4 Xbox consoles over a local network. PC-savvy and college-aged players saw it as a cheap, relatively hassle-free way to quickly organize LAN parties — a PC-gamer staple —that rapidly became a pillar of Halo’s early growth and cultural popularity.

This is where Microsoft bringing its PC ethos to the console wars paid off. Halo became a party and dorm favorite through addictive and robust multiplayer modes because of the Xbox’s powerful networking capabilities. It also socialized Microsoft’s vision for the future of console gaming: not just split-screen and social, but online — brilliantly setting the stage for what would become their Xbox Live service a few years later.

What’s remarketable about Halo today

Twenty-four years later, Microsoft’s Halo playbook offers many repeatable tactics for brands seeking to differentiate themselves with a killer app, as well as valuable lessons on which pitfalls to avoid.

• Most remarketable- Disrupting the status quo: Halo’s controller scheme is now gospel for every console shooter, from Call of Duty to Fortnite. In business, it’s not often that you get to reinvent the way things are done. But Halo did it for the FPS genre, the same way Uber did it for public transportation, and Apple did it for smartphones. Consoles represent the largest share of the FPS market today because Halo made the genre more viable and approachable--your reminder that killer apps often disrupt the status quo by showing consumers “a better way”.

• Most remarketable - Master Chief = Xbox: Fries and his team may not have planned on it, but Halo’s powerful sci-fi protagonist rapidly became synonymous with the Xbox brand, helping position the console as the more technically powerful gaming platform. That imprimatur helped them attract a coterie of technically ambitious developers and titles over the following years, including Ubisoft’s Splinter Cell, which was first developed for the Xbox as a technical showcase and later downported to PS2 and GameCube. By leaning into this halo effect, pun intended, Xbox became a tractor beam for development, a massive win for any aspiring platform.

• Least remarketable - “The Duke” and alienating Japan: While Halo’s controls were revolutionary, the Xbox’s original controller, nicknamed “The Duke,” was much less so. Comically oversized, it was of a piece with the console’s overall clunky aesthetic. The feedback from Japanese developers, in particular, was immediate and harsh, with many third-party publishers postponing development conversations until ergonomic concerns were addressed. Microsoft had to rush out the slimmer “Controller S” within months, pushing the Japanese launch to 2002, by which time the damage to perception had already been done. This, coupled with other cultural missteps, such as over-reliance on Western-centric games at launch and perceived arrogance and tone deafness during negotiations with local publishers, compounded its woes. Xbox sales bombed in Japan, with fewer than 10% of first-generation consoles sold there during its lifetime.

Xbox’s Japan woes may not have been preventable, but they serve as a reminder that a killer app is not a silver bullet.

More often than not, different markets will require different approaches. In the enterprise software space, for example, it’s great to have a big Fortune 500 logo to lead with in your marketing assets, but that logo is meaningless if it doesn’t resonate with your intended audiences at a local, cultural, or aspirational level.

Why AI needs its Halo

The parallels between the console wars from 2001 and today’s AI wars are hard to ignore.

AI companies are burning through billions in cash on compute infrastructure and racing to deliver more capabilities at lower prices. OpenAI, Google, Anthropic, and others are locked in what feels like a specs war — over which models score higher on benchmarks, which can process the most tokens, and which can integrate with the most workflows — all while chasing users at a net loss. The same users who, by the way, go back and forth between models because they all do similar things.

Sound familiar? It’s the same loss-leader strategy console manufacturers have run over time. But the difference is that each has a killer app users swear by, keeping them loyal. Microsoft has Halo, Nintendo has Mario, and PlayStation has Miles Morales.

ChatGPT had a running start when it proved in late 2022 that LLMs could actually work and were here to stay. But within months, everyone had a chatbot.

Today’s AI competition feels less like a race to create breakthrough experiences and more like a race to raise and blitz-scale while investor sentiment is strong.

It’s a pity, because within that envelope lies a genuine opportunity for companies to innovate further by delivering transformative moments people are willing to pay for: AI-powered experiences that feel magical because they redefine how things are done.

Vertical AI companies seem to be the closest to delivering a killer app right now, whether it’s legal research and workflows that change how attorneys work (Harvey), agentic AI-powered customer service experiences that boost bottom lines (Sierra), or low-code platforms that deliver an army of engineers and designers with every prompt (Lovable).

The cost of not having a killer app

Want to see what happens when you skip the killer app? Look at Apple’s Vision Pro.

Despite jaw-dropping specs and Apple’s undeniable innovations, Vision Pro launched to the public without a buzz-worthy use case that triggered a “holy shit you have to try this” moment. At $3,500, it promised immersive experiences for work and play, but nothing you couldn’t experience for far cheaper through other means or that didn’t require you to wean yourself away from the world.

As a gadget geek who’s all in on the Apple ecosystem across music, movies, and TV, I tried it but couldn’t justify pulling the trigger.

The Vision Pro is a textbook example of what happens when you lead with specifications instead of use cases. Even Apple—with its infinite resources and history of entering established categories late and still winning—couldn’t make its new platform succeed without delivering that one experience that makes people truly care.

Finish the Fight

Here’s what Microsoft taught us with Halo: products and platforms don’t sell on specs—they sell on proof.

Halo was an experience so compelling that it justified buying into a new console platform. The system, with its bulky and then not so bulky controllers, the built-in broadband service, were all worth it because of those split-screen and online sessions that ran until 3 AM.

Twenty-four years later, that lesson is more relevant than ever.

If you’re launching something new—whether it’s in AI, AR, or whatever comes next—ask yourself: what’s your killer app?

Not your specs. Not your benchmarks. But that moment of proof, that time to value, that makes someone realize things have changed for the better, and they can’t wait to do more with your solution.

That’s what I remember about my first time playing Halo. Not the Xbox’s GPU or RAM specs or other technical wizardry. It was knocking back silver bullets with one of my best friends, playing well into the night.

Specs don’t create loyalty—memorable experiences do. In a crowded marketplace, launching with a killer app may not guarantee you victory, but much like having the Master Chief by your side, it gives you a fighting chance.

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