Something that I truly loved died on Tuesday. 😔 

It was a slow, painful death — several years in the making.

In light of this news, I couldn’t finish the newsletter that was planned for this week. It’s hard to make your brain do one thing when your heart is pulling you in a different direction.

So today, you’ll find my raw and unedited perspective on the rise and fall of Trends by The Hustle — the media company that changed my life.

Oh lord.

Shiny and new

On June 4th, 2019 at precisely 9:09am EDT, my favorite newsletter, The Hustle, announced the launch of its new premium subscription:

Which I promptly ignored.

Why?

I was far more interested in The Hustle’s headlines that day, which included:

—

—

The Hustle had pulled off something truly revolutionary.

It delivered highly credible business and tech news that wasn’t just not boring — it was laugh-out-loud entertaining.

I mean, where else (at that time) could you devour cheeky copy like “Dr. Dre is gonna be pissed” and “thanks to demand for second-hand second hands” from a reputable editorial outfit?

I f*cking adored it.

(Still do. Still read it every day. Still snort coffee out of my nose.)

But there’s another reason I ignored Trends when it first launched (besides the cringy name)—

It was being promoted as the “new premium publication that analyzes the fastest-growing startup trends.”

I simply had no need for that. 🤷

At the time, I owned a commercial real estate advisory business that, while young, couldn’t have been further from a “startup”.

So while I was glad The Hustle was expanding their publishing portfolio, I wasn’t the customer that Trends was built for.

Until I kinda was.

What came first?

Not long after Trends was launched, I suddenly found myself neck-deep in startup culture.

Coincidence? Who the hell knows. 🤷

But the in span of a few months, I was:

• Investing in tech startups

• Considering accepting a board position at a tech startup

• And even laying the groundwork for my own tech startup

I was now an ideal Trends subscriber, but it wasn’t the newsletter that attracted me to the product…

In the final weeks leading up to the launch of Trends, the founding team had haphazardly started a Facebook group for subscribers and friends of the publication.

And when magic started happening in that Facebook group, they noticed its potential, and repositioned it as a core offer instead of just a “bonus feature”.

You weren’t a Trends “subscriber” — you were a Trends “member”.

That’s what caught my attention.

I whipped out my credit card, bought a Trends membership, and dove into their Facebook community.

There’s no quicker way to get smarter about something than to unapologetically throw yourself into a community of people who are smart about that thing.

And that’s what Trends was for me.

Before I knew it, I was checking the Trends Facebook group every day, and devouring every word of the weekly newsletter.

It had the same clever and edgy tone as The Hustle, but dove deep into market insights, and made killer predictions (like when Ethan Brooks confused the hell out of everyone by claiming that pickleball would be the next big thing — and he was damn right.)

I soon befriended the writers, volunteered to lead the Trends blockchain subchapter, and began contributing to research.

So when an opportunity arose for me to join the team in an official capacity, it seemed like a no-brainer.

What I didn’t realize was that it was already the beginning of the end.

Big Tech killed the Media Star

In 2021, The Hustle and Trends were sold to the business solutions software giant, HubSpot, for a reported $27 million.

Why in the world would a boring B2B software company want to shell out that kind of dough to acquire a couple of edgy media assets? 

The strategy is actually quite brilliant, but not without hidden flaws.

Here’s why they did it:

1. They gained access

The Hustle and Trends’ audiences were largely people who had decision-making authority in small-to-medium businesses, which are HubSpot’s ideal customers. By buying those media assets, HubSpot could advertise to those audiences as much as they wanted to, rather than having to repeatedly buy ad placements to get in front of them.

2. They removed access from their competitors

If they owned the media asset, they’d control everything in it. They would be able to nurture that audience and lay off the “promotional gas” any time they pleased without the risk of a competitor sliding in and controlling that audience’s attention.

This seems like a no-lose situation, right?

Tell that to PENN Entertainment, who bought the popular media brand, Barstool Sports, for $551 million for similar reasons… then sold it back to the founder for $1.

That would have been a great outcome for Trends. But instead, HubSpot killed it in a slow and painful way.

Here are my personal thoughts on what happened.

Cultural misalignment

Since I was joining the Trends team post-acquisition, I was technically taking a job with HubSpot.

Margaret Thatcher famously said, "Being powerful is like being a lady. If you have to tell people you are — you aren't."

The first thing I noticed during my cult initiation onboarding training at HubSpot was their obsession with “culture”. 

Obviously companies have culture.  

Obviously it’s important for company leaders to intentionally craft that culture. 

And obviously it’s important to create language that helps express the tenets of the company’s culture.

But HubSpot was shrieking “LOOK AT OUR CULTURE ISN’T IT AMAZING OMG I LOVE WORKING HERE OMG WE’RE ALL SO LUCKY,” like a cheerleader on meth.

They published a 128-page “culture code” — and blasted it out to the entire world.

I think Thatcher would agree that this level of overkill is a massive red flag.

The two weeks of “training” I endured (before I was permitted to even think about doing the stuff they had hired me to do) felt more like they were teaching me how to be a good human rather than a good employee of the company.

It was rooted in group-think, condescending as shit, and most importantly, completely counter to the edgy, contrarian, and authentic voice of The Hustle and Trends.

Uh oh.

Product misalignment

From my very first interview, until my final days with the company, I had one important question that nobody could answer—

What value did Trends bring to HubSpot?

Unlike The Hustle, which was a free publication that had 1.5 million subscribers at the time of the acquisition (now 2.5 million), Trends was a small, premium newsletter with ~15k subscribers, each paying ~$300 per year.

Do the math, and you’ll find that on its own, Trends was a solid little media business.

But since people were paying for Trends “membership”, HubSpot was limited with how much they could push their products on that audience.

Plus, it was a tiny group compared to their other media assets.

What they were left with was the company’s only non-software product, which contributed less than $5 million to the company’s annual revenue of over a billion dollars.

So while it was easy to make sense of The Hustle’s acquisition, giving HubSpot perpetual "presenting sponsor” access to a huge daily audience, the same couldn’t be said for Trends.

So why buy it?

The only answers I ever got were:

1. The Hustle and Trends were just sort of a package deal.

2. HubSpot’s founders, Dharmesh Shah and Brian Halligan, were big fans of Trends.

Neither of those reasons had any strategic substance behind them.

Editorial misalignment

Journalists are the best bullshit detectors on the planet.

It’s literally what they’re trained to do:

• They don’t simply accept what they're told. Prodding is non-negotiable.

• They remain independent from political, corporate, or personal interests.

• They protect objectivity, and always provide context around opinion.

But tech companies have one primary responsibility:

• Protect shareholder value.

So when a tech company buys a media company, they’re doing two things:

1. Inviting the world’s best bullshit sniffers into their internal operations.

2. Creating a situation where the values of their employees are often at odds with the values of their company.

What could possibly go wrong? 🙄

Well…

On January 31, 2023 (during my short tenure), the entire HubSpot workforce woke up to an email from the CEO that began with this paragraph:

As an editorial team, we were instructed to place a moratorium on any kind of reporting on the subject of layoffs for a few weeks.

So basically, we could kiss our objectivity goodbye.

Dozens of big tech companies had been making cuts after the COVID tech-boom began to subside, and we had been reporting on them.

But the company wanted us to all-of-a-sudden pretend like this wasn’t happening.

I accidentally broke the moratorium later that day (seriously, it was actually an accident, I’m not being facetious).

That afternoon, I was scheduled to interview Carmine Gallo, prolific entrepreneur and author of The Bezos Blueprint, in front of a live virtual audience.

When I asked Carmine what had inspired him to become an entrepreneur, he launched into a thoughtful monologue about the instability of full-time employment, and how his experience at big companies who performed layoffs drove him away from corporate America.

Some of these companies were even so insensitive as to announce layoffs over email, he claimed, as his words were broadcasted live. 😳

Whoops. 🤷

Look, journalists are a feisty bunch, and working for a company like HubSpot didn’t jive with most of them. By the time I joined the team at Trends, almost all of the writers were on their way out the door.

And they weren’t replaced.

_{Note — Carmine had no idea HubSpot had just laid off 500 people the day of our interview. He’s an incredibly compassionate and classy guy, and I’m certain he wouldn’t have made those comments within the context of that day if he had known.}

I was the face of a sinking ship. Oh god.

All of a sudden, I found myself to be the public face of Trends, as budgets were being cut and priorities shifted elsewhere.

Strategically, Trends didn’t make sense as a HubSpot asset. And while there were plenty of viable options available, huge, bloated corporations simply aren’t nimble and responsive enough to execute pivots.

It was easier for them to just slowly divest. Over the course of a year:

• We completely halted new member growth.

• Programs and features were stripped away.

• Community management was put on the back burner.

But the biggest problem with those moves was that our ~15k members, who had all paid $300 for our product, weren’t told any of this.

They just knew the product was getting worse.

So to them, it just looked like I was terrible at my job.

I noped out of there, and about a month later, HubSpot sunsetted Trends as a premium media product.

They shut down the community, got rid of every program, and refunded all of the members.

But they retained a pared-down version of the weekly Trends newsletter, crafted entirely by one incredibly talented writer. 

Like The Hustle, it was published for free, and supported by plenty of HubSpot advertising.

And two days ago, at 8:03am EST, they published their final issue — ever.

Not gonna lie, it’s a tad emotional. 

Without Trends, I wouldn’t be doing any of the exciting things I’m doing right now, nor would I have heaps of incredibly special people in my life.

But like an atomic clock, the Trends early-bird pricing GIF beats away for all eternity in one of my long lost inboxes from 2019…

We soldier on.

The Hustle is still owned by HubSpot, and while the original editorial team has moved on, it remains the best source for business and tech news on the internet.

So all is not lost. 🫶

Cheers! 🍻

-Kristin :-)

P.S. — Today’s issue paints a very broad picture of what happened (in my eyes), leaving out a lot of important factors, including mistakes that were made long before HubSpot acquired Trends. I plan to write a deep dive on this story in the near future.

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