Buckle up, people.

Per the New York Times, the US Justice Department will brief state attorneys general on a Google antitrust case, which the feds could file next week.

The issue? Google harming consumers and competitors with its dominant search position.

Among Big Tech companies, Google has the clearest monopoly

The internet giant has a 90% share of the US search market. On a percentage share basis, the positions for Facebook and Amazon in social site visits (56%) and US ecommerce (35%), respectively, are much less significant.

Critics and competitors complain that Google:

• Prioritizes its own products in search results (think restaurant or travel listings)
• Takes publishers’ content without linking to their sites (think the Answer Box)
• And dominates the ad-tech biz

This isn’t the first antitrust rodeo for Google: in 2013, the Federal Trade Commission investigated whether Google searches were biased — but concluded the company didn’t violate any laws.

More recently, the search giant had to change its Play Store policy for Android phones following an EU antitrust case.

But Amex has created a ready-made defense for Google

In a recent Supreme Court case, US states sued American Express (Amex) for charging merchants exorbitant fees and not letting its customers ask for the option to switch to Visa or Mastercard.

Amex offered a “novel” defense that could apply to Google’s current predicament, says antitrust writer Matt Stoller: it wasn’t enough to show that a monopoly existed, but that the company’s policies towards merchants resulted in a net loss across the entire payment network.

In its case, Amex cited the fact that it offered points to consumers, which offset any losses sustained by the merchants.

The argument worked

The Supreme Court sided narrowly with Amex, giving powerful companies “de facto antitrust immunity,” according to legal scholar Lina Khan.

Following this reasoning, Google can say its entire search network is a net positive as the company lowers total ad costs and helps publishers make money by funneling traffic.

However Google plays it, there will surely be fireworks. This could be the biggest monopoly case since Microsoft and — if it makes its way to the Supreme Court — may be decided by whomever replaces Ruth Bader Ginsburg’s seat.

In 2009, AJ Vaynerchuk, then 22, co-founded VaynerMedia with his brother Gary. As COO of the firm for 7 years, AJ helped grow the social and digital agency to 1k employees and $100m+ in revenue.

Since 2016, AJ has been running VaynerSports, a full-service sports agency.

Our Alex Garcia caught up with AJ for some key lessons from his entrepreneurial journey:

How did VaynerMedia differentiate itself as a new agency?

We went… [all in] on social media as a platform. It sounds obvious in 2020 but — in 2009 — social was a complete afterthought for most agencies.

By the time our competition realized that social media was a platform that mattered, we were already 3-4 years ahead of them in terms of best practices, case studies, a client roster, and network of executives at the social platforms.

How were you able to take on the COO role at such a young age?

I’m a big believer that our society views experience in the wrong way. Everybody looks at experience as a defined number based on days, weeks, and years.

At 25, I spent a year managing probably like 40 clients and 300 employees. That is not the same “age 25” level of experience [as other ad agency COOs]. So the way I look at it, I was four years in, but I had like 25 years of experience.

What was VaynerSports’ differentiation when it launched?

The vast majority of agencies focus on contracts. There’s another group that does marketing and off-field endeavors. A few agencies try to bridge those two but — in my opinion — nobody was doing it well.

We also found that agents were often the closest investment advisor to athletes even though most don’t have experience with investing [whereas we do]. So, yeah, I’d say VaynerSports is differentiated because we bring together those 3 prongs: contracts, marketing and investing.

Next time you type your skin rash symptoms into WebMD, brace yourself for a barrage of ointment ads.

According to Blacklight, a new tool from the nonprofit tech site The Markup, dozens of marketing companies track your WebMD visits.

And don’t think health websites are alone here: Blacklight lets you see exactly what info all sorts of websites  have on you.

How does it actually work?

You have to go to the tool’s homepage and enter a link.

The system then reads the page for “trackers.” That means info about you, your keystrokes, and your searches that advertisers and other companies are compiling.

Should I be worried about this?

A lot of what Blacklight reveals is obvious. As Recode points out, you probably won’t be surprised to hear that news sites have a couple dozen ad companies tracking you.

There are definite shades of gray, though. Breitbart, for instance, uses a tool called “canvas fingerprinting” that keeps tabs even if you turn off your cookies. Airbnb’s website does the same.

And then there are the bizarre cases: Even government COVID-19 informational pages apparently forward your info on to ad-tech companies.

Sam recently Slack’d the team with the above fun fact about Tesla’s car model names. (Yes, Sam’s avatar is Harvey Dent / Two-Face.)

Tesla seems to have a knack for pulling off corporate flexes. But this nugget inspired us to go back to the archives and dig up some efforts from other companies that didn’t quite hit the mark.

Freshworks’ Dread Zeppelin

• What it was: A blimp toting the hashtag #Failsforce that circled the Salesforce Tower during its flagship Dreamforce event, with 170K+ attendees looking on.
• Why it failed: Freshworks scored points for sass, but that’s about it. Salesforce continues to absolutely dominate the CRM market.

Richard Branson’s Tank

• What it was: In 1994, the Famous Virgin himself drove a tank through Times Square and “blew up” the Coke sign to announce the arrival of Virgin Soda in the US.
• Why it failed: Coke drove them out of business shortly after. Karma, Sir Richard.

Slack’s “Dear John Microsoft…” Letter

• What it was:: A full page Slack ad in the New York Times welcoming Microsoft Teams (a new competing product) to the scene.
• Why it failed: It read like a passive-aggressive letter that a condescending ex would write. (Microsoft: If you’re reading this, Slack still wants its damn sweatshirt back.)

Did we forget any flex failures? Do share.