Every two weeks in Zero Clicks, we explore the interplay of AI, media, and commerce. In each edition, we explore…

• The big picture: The trillion dollar challenge of accelerating discovery

• Job posts: The 28-year-olds who are holding companies together (otherwise known as chiefs of staff) 

• The meme(s) are the message: Laughing through the market pain   

• One final read that’s worth your time: Staying relevant in the age of AI

Tomorrow is now

"Today, online commerce saves customers money and precious time. Tomorrow, through personalization, online commerce will accelerate the very process of discovery." - Amazon Letter to Shareholders, 1997

These are tumultuous times in technology and commerce. President Trump has, in the words of Matt Stoller, taken “a sledgehammer to the world trading system, without answering the question of what he is trying to build.” Markets have reacted in kind, and it quite frankly feels silly to be writing about anything else. But I have no desire to languish in bad vibes, especially when so much interesting work is happening at our industry’s frontier.

The quip at the top of this piece is the most famous line in arguably the most famous business document ever written. It has appeared in probably hundreds of thinkboi decks, analyst reports and startup pitches from those who claim they are building tomorrow. But for much of the past decade, accelerating discovery has remained frustratingly elusive, even as online commerce has advanced.

However, with recent advancements in AI, 2025 feels like the first true year where "tomorrow" is technologically possible. To understand this, it’s important to understand how the vernacular meaning of “AI” has fundamentally changed in our business. 

For the last decade, when somebody was selling you AI as a retailer or brand, they were effectively selling conversion rate optimization (CRO) tech in some way, shape, or form. Long before Chat-GPT, every software that aimed to increase average revenue per visitor billed itself as “AI-powered,” a hodgepodge of conversion rate hacks that the vendor-industrial complex collectively defined as artificial intelligence.

To be clear, much of this technology was incredibly valuable to commerce – automating reasonably basic CRO and product recommendations testing unlocked billions of dollars of incremental value for retailers and spawned a host of nine figure software exits. Whether or not any of this tech was truly “AI” is a purely semantic discussion; what matters is that the value proposition is fundamentally different from most of what is now being sold under the AI banner.

Until now, truly "accelerating discovery” stopped at collaborative filtering, which is essentially the ability to predict user preferences by analyzing similarities between users and items at massive scale. Nobody did this remotely as well as Amazon (except arguably Netflix in a slightly different context) and so Amazon won the first era of commerce. 

Ironically, it looks less likely every day that Amazon is going to be the company that wins accelerating discovery. It is perhaps the only place their vice grip on commerce is vulnerable.

Amazon’s dominance still fundamentally begins from a defined search intent– the company is by and large not in the business of manufacturing moments of serendipity for shoppers. Creating serendipity, and thus demand, is the core reason why Amazon threw their hat in the ring for TikTok, despite the obvious geopolitical complexities in such a deal.

#TikTokmademebuyit is the most important phrase in our business. Is anyone saying Google made me buy it? Or Amazon? Or even Instagram anymore? TikTok is the closest thing we have to an engine that truly accelerates discovery. Impractical though it may be, it is fascinating to think about what would be possible if Perplexity somehow emerged from the fray to rebuild their personalization engine in America.

Online commerce alone is a $6 Trillion industry globally – even if we assume 80% of searches are simple precision search jobs for toilet paper, that still leaves >$1T in value from helping users truly discover what they want to buy.

The spearfishing market of defined user intent is largely tapped out and perfected. The more nebulous notion of “Find me an outfit for a girls trip to Chicago” is where most of the growth in commerce will come in the years ahead.

Solving semantic search problems like the above will unleash hundreds of billions of dollars in new enterprise value and create new commerce experiences that are near impossible to imagine today. This will happen in five years or less.

TL;DR:There’s never been a more fun time to work at the intersection of technology, media and commerce. Tomorrow is now.

Chief of Staff, Fermat

I’ve worked with many chiefs of staff in my career and they are, bar none, the smartest and hardest working people you’ll ever meet. Behind every hyperscaling startup is a 27-year-old holding it all together with toothpicks and 90-hour weeks.

It’s a grind and in many ways, the ultimate sucker’s job on paper. However, if your goal is to rapidly accelerate your learning, joining a Series B/C company that is growing fast and has product-market fit is rocket fuel for your development.

Fermat fits that bill as a successful software business rapidly adapting to the world of agentic commerce. No shortage of hard problems there

Director of Marketing, Bobbie

What does building an iconic brand in 2025 look like? It is opening a job for a marketing leader and having to close the floodgates after one day because you already received 600+(!) applications. 

Congratulations to Kim and team for putting on a masterclass every day.

Director of Sales, Strategic Partnerships, Mr. Beast

From the hottest gig in marketing to what I imagine has to be the hottest gig in ad sales, the pinnacle of modern media is staffing up.

Try as I might, I still can’t make it through two minutes of a Mr. Beast Video without questioning my sanity. Jimmy Donaldson exists solely to remind me I know nothing about GenZ, video, social hooks, media, human psychology, or perhaps the very essence of life itself.

But he sure as hell knows how to make money – go get a piece of the action.

Sr. Director, Membership Marketing, Consumer Reports 

Longtime readers will know that I’m an unapologetic Consumer Reports stan – I think it might be the best place to work in media right now.

If nothing else, they are paying twice as much as many of their peers for a talented lifecycle marketer and doing work that looks more and more necessary every day as the world of global commerce gets increasingly complex.

Ok, so everyone is blaming this market bloodbath on Trump tariffs....have we at least considered that this could simply be a rational market response to the sudden prevalence of "torpedo bats" in Major League Baseball? Last time, there was economic disruption of this scale, bats were allegedly involved…

Meanwhile, on LinkedIn……

And finally, this meme is not an original but is my favorite of 2025 so far:

Read more of Ian Leslie’s writing

We’ve tried a lot of things for this bottom section – stock charts, cocktail recipes and trivia questions. I’ll  sign off now with the best thing I read on the web within the  past two weeks.

Ian Leslie is perhaps my favorite generalist writer. His pieces have incredible range and run the gamut from quips of advertising and politics to the best writing on the enduring power of the Beatles on the web.

His “Nine Principles for Success in the Age of AI” is a uniquely great read – it’s partially behind paywall but this is the moment to use your free Substack post