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Forget about the big game on Sunday. Two heavyweights have been battling it out this week over a topic thats become all-too-familiar over the years: advertising creep. Its a tale as old as time, in some respects. Many a CEO have proudly declared that their companys platform or services will remain ad-free, only to later succumb to the lure of all that advertising revenue and embrace it. And thats creating a new divide among AI platformsone that will play out to the worlds largest TV viewing audience during the Super Bowl. Among the nearly dozen AI-related ads on Sunday will be two 60-second spots each for OpenAI and Anthropic. While OpenAI will use its time to tout how its ChatGPT helps people build things with a real-world impact, Anthropic is taking a swipe at its much-larger competitors recent decision to incorporate ads into the platformand its virtuous decision to keep its Claude AI assistant ad-free. This off-field action has already made for some entertaining viewing. Anthropic dropped four ads this past week set to Dr. Dres 2001 song Whats the Difference, which all conclude with the same warning: Ads are coming to AI. But not Claude. That elicited a lengthy post on X by Sam Altman, OpenAIs CEO, thats since become the topic of much ridicule. While Anthropics Black Mirror-esque ads are extremely clever, theyre also strategic, as the company seeks to position itself much like Apple has with its privacy-first messaging, says John Battelle, an entrepreneur and author. Claudes marketshare may be a tiny fraction of ChatGPTs, but Anthropics swipe at OpenAIs reversal on advertising was well-playedand it makes an important point, according to Battelle. I applaud what they did,” he tells Fast Company. “This needs to be talked about.” Pivot to revenue For Altman, the advertising U-turn took about 15 months. In October 2024, he said that he viewed advertising as a last resort as a business model for OpenAI, only to seemingly reverse course a few weeks ago. Hes hardly the first to do soand for good reason. Theres no question that the only business model that you can employ if you want to scale a business is advertising, Battelle says. Advertising . . . finds a way Recent decades have seen a well-trod path for companies that transitioned to an advertising-supported business model from one that was originally based on subscriptions or, seemingly, free for users. Advertising has slowlyand sometimes not so slowlycrept into almost every major platform controlled by a large tech company, whether it’s social networks like Facebook or streaming services like Netflix, to name a few. But Google perhaps offers the canonical example of a companys founders finding their advertising religion and walking back prior vows to remain ad-free, says Battelle, whose book The Search: How Google and Its Rivals Rewrote the Rules of Business and Transformed Our Culture” was published 20 years ago by Penguin In a 1998 white paper laying out their vision for Google, cofounders Sergey Brin and Larry Page didnt mince words about the potential mixed incentives of a commercial search engine with a business model predicated on advertising. The goals of the advertising business model do not always correspond to providing quality search to users, wrote the duo, then-PhD students at Stanford University. We expect that advertising funded search engines will be inherently biased towards the advertisers and away from the needs of the consumers. In 2000, Google began selling advertisements. To say it’s become a big business would be an understatement. Parent company Alphabet reported this past week that Google advertising accounted for more than 72% of its $113.8 billion revenue in the fourth quarter. A hill to die on For some founders, advertising has been a hill theyve been willing to die on. Clashes about advertising on WhatsApp were reportedly among a variety of reasons why cofounder Jan Koum ultimately left parent company Facebook (now Meta Platforms) in 2018, four years after the messaging app was acquired. Koum had long expressed his disdain for advertising and how it worsened a product. He vowed to keep advertising out of an app where people communicate with friends and family, and his first-ever tweet was a quote from the movie Fight Club that pulls no punches: Advertising has us chasing cars and clothes, working jobs we hate so we can buy shit we dont need. Last year, WhatsApp debuted ads in the app. The future of advertising on AI Like many before them, the founders of AI companies must now determine where their line in the sand is on advertising. And its no surprise that advertising has eventually found its way into AI platforms, as Battelle laid out in a recent blog post. As Google, Facebook, Uber, and other companies have taught us, advertising creep does gradually change the services we know and love, Battelle says. In some cases, like with Instagram, the product today barely resembles its pre-advertising self. When you commit to advertising, you commit to the incentives of advertising, he says. Even if advertising on AI platforms will inevitably evolve with time, Battelle says an imperative question now is what that future will look likeand particularly if social media is the reference point. Man, things are not going to be pretty if the business model that drove social media also drives generative AI.
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E-Commerce
Taking the leap from traditional employee to solopreneur involves a number of decisions and considerations that may come as a surprise if youve always been on someone elses payroll. Being numero uno for every part of your solo enterprise can illuminate just how complicated it can be to keep any kind of business running. Unfortunately, becoming a solopreneur can complicate your personal financial choices as well. Thats because money habits that felt innocuous while you were on a biweekly pay schedule can create financial mayhem on an irregular income. Whether youre considering becoming a solopreneur or have been rocking the solo business world for a while, make sure you dont carry these common paycheck habits with you into your entrepreneurial venture. Ignoring your bank balance Prior to becoming a teacher, I worked a series of low-paying jobs, including several stints where I stitched together multiple part-time positions. During that period of what we might generously describe as my early career, it was my habit to check my bank balance daily. This was in the early 2000s, when the internet still required a kerosene-powered modem to access Google, so it took some effort on my part to indulge in this habit. But since I was making so little money, I needed to know on an almost daily basis what was happening in my account to make sure I hadnt overlooked anything. When I started teaching and bringing in the medium bucks, it was a relief to only check my bank balance when I paid my bills rather than every single day. As a public school teacher, I knew exactly how much money I received in each paycheck, I knew exactly when it would clear my account, and I knew that if my mental accounting was off by a little bit, I didnt have to wait long for the next paycheck. (Ironically, the only time Ive ever overdrawn my account was during the regular-paycheck years of my life.) Befriend your banking tools Becoming a solopreneur is a little like going back to your early twentysomething career, at least financially. Keeping a weather eye on your finances is the only way to stay ahead of problems before they blow up. Theres no steady paycheck to smooth over any issues. The good news is that banking technology has come a long way since I had to keep my modems kerosene tank full just to log onto the internet. These days, virtually every bank and credit union under the sun has an app that will allow you to set up personalized alerts and text notifications, among other tools. This makes it very easy to set up regular bank balance check-ins, whether you create an alert to notify you when your balance dips below a certain dollar amount, or you have your bank text you the current balance every day at the same time. Waiting for tax season Paying taxes is no ones idea of a good timebut at least when youre working for a paycheck, the taxman knocks but once a year. Whether you use a CPA or do them yourself, taxes are fairly straightforward for those who are traditionally employed. Once you have your W-2 in your hot little hand, you can typically get started sometime in early spring, then patiently wait for your tax refund to arrive . . . and youre done until next year. But solopreneurs dont get the luxury of treating taxes like a sucky annual holiday. Because small-business owners dont have taxes withheld from their income, they have to pay quarterly estimated taxes, filing each payment with Form 1040-ES. The approximate due dates for each payment are as follows, but they may be pushed back if the 15th falls on a weekend or holiday. First quarter (January 1-March 31) Due April 15 Second quarter (April 1-May 31) Due June 15 (June 16 in 2026) Third quarter (June 1-August 31) Due September 15 Fourth quarter (September 1-December 31) Due January 15 Solo business owners also typically have to deal with much more complicated tax reporting if they have multiple clients. That means they are fielding more tax formssuch as 1099-NEC and 1099-K formsthan traditional employees. Build tax infrastructure into your business Paying and organizing solo business taxes are overwhelming if you only think about them when theres a due date. But they can be an easy part of your daily routine if you build tax infrastructure into your business plan. For quarterly estimated taxes, it starts with planning ahead for paying Uncle Sam. You can do that by creating a savings account where you transfer about 20% of each payment you receive. This will ensure that you always have the money you need to pay your estimated taxes each quarter, so youre not scrambling to find the cash every three months. Over time, you can adjust how much you set aside for taxes as needed. As for organizing your taxes, this can also be a relatively simple and ongoing part of how you conduct your business. Its important for solopreneurs to have an accurate account of their income, since its always possible a client will make a mistake on the 1099 they issue. An invoicing structure where you record income from specific clients at the same time you mark their invoices as paid can be a small tweak that will make tax organization much easier. This could be as simple as a Google sheet that you keep updated, as long as you are consistent. Taking no vacation days When you work a traditional job, it can be easy to forget to take time off. Whether you get a set number of vacation days per year, or your workplace offers unlimited PTO (which really means you get the hairy eyeball if you try to schedule any), its easy to reach the end of December before youve realized you never took a vacation. This is obviously a serious problem within the American workforce, which is suffering from burnout, lack of work boundaries, and a bad case of the Mondays. While none of that is good, many workplaces do at least offer regular time off in the form of weekends and federal holidays. Workers who habitually leave their vacation days unused can still count on several long weekends and other breaks throughout the year to give them a needed opportunity to rest. Block off time for rest Working for yourself means you dont have to stick to a 9-to-5 schedule, but it also means you might be working at midnight, on weekends, and through Thanksgiving dinner. The habit of working without a vacation can be especially tempting when your success or failure depends on your hustle. But youre solely responsible for your business now, which includes the well-being of your only employee. You cant rely on the holiday calendar to provide you with time away from your work like you did as a paycheck employee. You have to set the boundariesor deal with the consequences of burnout. Which could mean not being able to work at all. This is why you need to set the boundaries your previous schedule gave you automatically. You can do this by blocking off time weekly, monthly, and annually for rest. If you need to, imagine that your rest times are legally mandated so that youre not tempted to work through your vacation time anyway. Building better habits Working for yourself, by yourself, doesnt just require a change in how you structure your work dayyou may also have to revamp your personal financial habits. Without the safety net of a steady paycheck, solopreneurs cant afford to ignore their bank balances like they did as an employee. Your banks mobile app and online tools can help you keep track of your finances with automated alerts and notifications. While paycheck employees get to think of taxes as a single season of the year, solopreneurs have to deal with tax chores year-round. That includes paying quarterly taxes and keeping records organized. Setting aside around 20% of each payment can help solo entrepreneurs have the money they need to pay their estimated taxes every quarter, while recording their income as the invoices are paid can help make tax reporting easier come April. And though all Americans need to take more time off, those working traditional jobs can often count on weekends and federal holidays, even if they forget to use their PTO. Solopreneurs can get stuck in an endless working cycle unless they specifically block off regular time for restand guard it fiercely.
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E-Commerce
Days before the Super Bowl, Anthropic dropped a handful of Super Bowl ads taking aim at OpenAIs impending advertising model for ChatGPT. The ads anthropomorphize OpenAI’s platform, imagining how the chatbot might answer everyday questions like What do you think of my business idea? and “Can I get a six-pack quickly?” The answers, delivered by actors in cheerfully sycophantic robot speak, start out sounding like stilted but helpful advice, before veering into promotional marketing speak for a hypothetical advertiser on ChatGPT. Immediately, the ads sparked a firestorm online. Some called them brilliant. Others called them mean-spirited. OpenAI CEO Sam Altman felt so strongly, he crafted an earnest post on X about why Anthropic’s ads were so misleading. But wrong move, bro. Anthropic, one of your AI rivals, just handed OpenAIand the entire AI industrya huge gift. Not to mention the ad business. An ad battle for the AI age Not since the days of Coke and Pepsi have we seen this kind of ire slung at a category competitor. And I just have to say: I’m here for it. We are at a pivotal time for AI development and adoption across business and culture, with issues ranging from mass layoffs to people using LLMs for dating advice. But AI is also in its brand infancy, with some platforms building massive name recognition but very little brand image. There is no better category than AI to start a full-on advertising battle in 2026, and there are no two better companies to wage it than Anthropic and OpenAI. Anthropic has long framed its Claude platform as a more refined LLM than its OpenAI counterpart. And its Super Bowl ads are delivering an implicit message about the competition: You can’t trust them. Created by award-winning ad agency Mother, the new Anthropic campaign, A Time and a Place, has four spots in total (two are big-game bound). People want an AI they can trustone thats focused solely on working for them. We want Claude to be that choice, Andrew Stirk, Anthropics head of marketing, said in a statement. When OpenAI’s Altman opined on X that it’s on brand for Anthropic doublespeak to use a deceptive ad to critique theoretical deceptive ads that arent real, perhaps he should turn that into a brief for his growing all-star internal marketing team (imagine a 1984-style ad for 2026). I mean, he even has Brandon McGraw, former head of consumer marketing at Anthropic, on the roster. Same story with his second attempt at a clapback: More Texans use ChatGPT for free than total people use Claude in the U.S., so we have a differently-shaped problem than they do. What about an AI Challenge ad set in El Paso or Brownsville where they go full “Get a Mac” and paint Claude as the snooty also-ran to ChatGPT’s bot of the people? This consumer-facing dichotomy is the perfect setup for an advertising battle. You’ve got two brands offering ostensibly the same thing (at least to the average person), just with different positioning. Butas Coke and Pepsi demonstratedeven though brands involved in street fights like this do get a few ego bruises, historically the creative arms race helps both emerge in a stronger position with their audiences. First, the good part of the Anthropic ads: they are funny, and I laughed.But I wonder why Anthropic would go for something so clearly dishonest. Our most important principle for ads says that we wont do exactly this; we would obviously never run ads in the way Anthropic— Sam Altman (@sama) February 4, 2026 Challenger game The decades-long scrap between Coca-Cola and Pepsi is well-documented, but its dynamics have been replicated in various ways over the years in other product categories like tech, fast food, and telecom. There’s a typical anatomy to ad wars that cuts across industries. At their most basic, these campaigns always begin with a challenger brand calling out a much bigger rival by name. For Pepsi, which began the cola wars with less than 20% market share, that meant the Pepsi Challengeshowing real people choosing Pepsi over Coke in blind taste tests. This year, it meant hijacking Coke’s familiar polar bear for the Super Bowl. Apples Get a Mac is widely considered one of the best long-running advertising campaigns of all time. Apple was the challenger (if you can believe that) depicting the dominant PC brands (Microsoft Windows) as dull, cumbersome, and just plain uncool. Of course, the challenger brand is in the eye of the beholder, and in 2011 it was Samsung mocking iPhone fanboys for lining up to get what it deemed an inferior product. Over in fast food, Burger King had an award-winning run of work in the late 2010s under then-CMO Fernando Machado, much of which directly involved McDonalds. To promote the nonprofit Peace One Day, Burger King took out ads and built an entire website proposing to McDonalds that the rivals make peace to create the ultimate burgerthe McWhopper. The ad had $220 million in earned media value, and 8.9 billion impressions. In 2018, Burger King created print ads with photos of barbecue grills at former homes of ex-McDonald’s executives to highlight the flame-grilled taste of Whoppers. That same year, it launched Whopper Detour, a promo campaign that used geofencing to offer a 1-cent Whopper to users who ordered through the Burger King app while within 600 feet of a McDonald’s. It got 1.5 million Burger King app downloads in nine days. Even Taco Bell took a swing at the golden arches when it launched a breakfast menu in 2014. For its largest marketing campaign ever up to that point, Taco Bell recruited real guys named Ronald McDonald to testify to the tastiness of its Breakfast Crunchwrap. Whether people were emotionally invested because they loved one of these brands over the other, or they were just there for the LOLs, each of these sparked two things brands crave absolutelyattention and excitement. Strategic response A 2025 INSEAD study called The Power of Strategic Rivalry found that a well-managed rivalry can extend the story between competitors, keeping consumers tuned in longer andimportantlybenefiting both sides with ongoing engagement and relevance. People love a good brand fight. Coca-Cola maintained its lead throughout the cola wars, but Pepsis market share shot up from 20% to a peak of 30%-plus in the 1990s. And their ad war not only helped increase overall soda consumption from 12.4% of American beverage consumption in 1970 to 22.4% in 1985, but each brand more than doubled revenues over the 1980s. And thanks to the sheer intensity and ad frequency during the most heated years of their ad battle, the brands elbowed their way to the center of pop culture. Between 1975 and 1995, Cokes annual ad spending went from about $25 million to $112 million, while Pepsis grew from $18 million to $82 million. The haymakers from challenger brands are to be expected. But rarely, if ever, do the bigger brands respond with the same level of bite. In fact, the most successful responses have been investing in better creative brand work done more often. McDonalds didnt use its global domination to swipe down at Burger King. Instead it invested in and celebrated its existing fans in fun and unique ways. Specifically, with the Famous Orders work that began with Travis Scott in 2020 and expanded to collaborators as varied as Mariah Carey, BTS, and Cactus Plant Flea Market, driving record app usage, hundreds of millions in sales, and making new fans of younger customers. OpenAI appears to be taking a similar tack in its advertising, at least so far. The brand is focusing on how its tools can inspire and enable people to build new things. Its three regional Super Bowl spots are about how three different American small businessesa seed farm, a metal salvage yard, and a family-run tamale shopare utilizing ChatGPT to grow and thrive. OpenAI CMO Kate Rouch admits the Anthropic spots are funny, but since ads havent landed in ChatGPT yet, its a complete fabrication of what that experience will be like. When I spoke to her this week, she took issue with the spots calling OpenAIs use of advertising to support free access to the tools as a violation, and reiterated Altmans point that ChatGPT has more free monthly users in Texas than Anthropic has globally. And our perspective is that open, free access to this technology will enable individual people to build things that will benefit them and us all, Rouch told me. It really all comes down to self-empowerment and being able to do things that you either didn’t believe you could do before or you actually couldn’t do before. And that’s the whole game. This is a more sound strategy, both overall and in light of Anthropics trolling, than last years animated Super Bowl ad that had many people guessing just what the hell it was trying to say. If this is the dawn of AIs version of the cola warsand I hope it isits an impressive start for both brands. Anthropics challenger strategy here hits, not just for the cojones to step up to the Super Bowl against a much bigger rival. The key to any challenger swipe that actually works hinges on its creative execution, and these spots steer clear of the slop to serve up a bona fide chefs kiss. For OpenAI, creatively telling real stories about real people using its tools to solve real problems and build real things looks less like an advertising street fight and more like a turn for the high road toward the brand image promised land.
Category:
E-Commerce
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