🔴 Typos in newlsetters = good

Today’s guest is Adam Ryan, CEO of Workweek, a three-year-old business with an excellent newsletter program. It’s built around a roster of talent writing newsletters serving business niches like HR, healthcare, and marketing.

Adam is a newsletter monetization expert. Before co-founding Workweek, he spent four years at The Hustle, where he was the first sales hire and left as president.

In this issue:

• 🎭️ A Disney and Red Bull-inspired approach to building a content business

• ❌ Learning how and when to say no

• ✍️ Advice on using paid advertising to grow a newsletter audience

— Francis Zierer, Editor

P.S. We have a podcast! Listen to my conversation with Adam or watch it on YouTube.

The campus brand ambassador to media executive pipeline

When Adam Ryan’s parents dropped him off at college for his freshman year, walking by the business school, his mother asked him what people do with business degrees. “I have no clue,” he said.

Adam ended up getting a master’s degree in workforce education, but while studying, he received an education in business through a career as a campus brand ambassador, helping first Procter & Gamble, then HP, and finally Red Bull reach and make customers of his fellow students.

A half-decade later, he would play a significant part in defining the newsletter advertising model at The Hustle, one of the more well-known success stories in the newsletter world (software company HubSpot acquired it for $27 million in 2021).

Adam spent four years at The Hustle, joining as the first salesperson and leaving as president a few months before the acquisition was announced. Today, he is the CEO of Workweek, a business-focused media company that, unsurprisingly, runs a brisk ads business. He looks at it with one eye towards empire; to be the Disney of business. What he means by that is something he learned in his college brand ambassador days once he began working with Red Bull.

Don’t say no to big ideas, stick to your values

Adam was given license and encouragement to pull off ambitious campaigns — one involved him going to 12 town hall meetings to get the major to sign off on a street shutdown for a chariot-racing competition. He says the experience taught him how to be an entrepreneur, but more interestingly for us, it taught him what it meant to work for and operate a values-driven brand.

Workweek is a group united by clarity of values

What is Workweek? It’s a company of about 50 people, around 20 of whom work on ad sales, 8 on podcast, event, and other production operations, and the rest distributed across roles like finance, HR, and community.

At the core of the company is a group of business-vertical-focused creators. The roster currently numbers 6, though that number has fluctuated in just over 3 years of operation. We’ve interviewed two former Workweek creators in Creator Spotlight — Jared Dashevsky, a doctor who runs the Healthcare Huddle newsletter, and Tommy Clark, a content agency owner who runs the Social Files newsletter.

Given that Workweek’s creators are all business-focused, you might think they’d be fine on their own (Workweek, as Jared and Tommy told me when I spoke to them, pays a flat fee to each creator as well as a percentage of ad revenue).

I asked Adam about how he determines whether or not they’d want to work with a given creator, and I really liked how he frames this give-and-take:

Besides pure human labor in ad sales, Workweek threw an upfront event this past September (which is when a media company hosts advertisers to pitch upcoming advertising opportunities).

The Disney model

Workweek has only been around for three years, but it's been quite successful given that relatively brief time. They’re generating multiple millions per year across their ads revenue and other businesses, including an exclusive, fee-based social network for each of their business verticals launched this past summer alongside a $12.5M Series A fundraising round.

Adam says the dream is to “become this third home for the professions” their creators focus on. They may add more verticals and more creators down the line. I asked how many creators they’d feasibly need or want to have on the roster, and he said, “I think we have a multi-billion dollar business at probably 25.”

The model for Workweek is not dissimilar to the model Adam learned at Red Bull, which itself owes much to the Disney model: a house of brands and businesses united by specific values. Walt Disney himself illustrated this model 67 years ago:

It’s ambitious and complex; core brand values to which every decision must cleave blunt the complexity. I asked Adam for the most important piece of advice he could give based on his decade-plus in media:

Connect with Adam on Twitter or LinkedIn.
Subscribe to one of Workweek’s offerings.

🎙️ This was an excellent conversation. Adam is a real expert on the newsletter business and has much to teach; I could only fit a few pieces into this newsletter. I recommend checking out the pod for more, including:

• 💵 Struggling to convince advertisers to buy space in newsletters a decade ago to hosting an in-demand upfront event to sell newsletter ads this year

• 🎨 Everything Adam learned from attempting to become a creator to get better at working with and helping creators

• 🏫 Wild stories from Adam’s days as a highly resourceful campus brand ambassador (like convincing the mayor to close streets for a chariot race)

Listen on your preferred podcast platform or watch on YouTube.

Adam likes to talk about the content business in terms of “hits and habits.” With newsletters, he’s firmly in the “habits business. Newsletters are great for habit-building.”

This is a great way to think about your work as a creator — i.e., a habits-based audience that opens your newsletter every week is very stable, but occasional content designed to play as a hit beyond your existing audience, where you might’ve put a good deal of extra time and resources into production, might be a good vehicle for a high-ticket advertisement, or might bring new audience members into your habit base.

More ways to think about it, but you should know this about yourself: are you in the hits business or the habits business?

Here are a few of the best bits of practical advice Adam gave us:

Use paid advertising to grow, but be very deliberate

Paid advertising has been hugely important in growing the Workweek creators’ audiences — “For six, nine months, it’s very heavy paid advertising” — but the team approaches it rigorously.

1. Define the ideal customer profile (ICP) as distinctly as possible

2. Nail down the content itself to find content-market fit; make sure the content you’re putting out is aligned with what your ICP wants

Imperfect is perfect

To preface this, Adam used a business attire analogy. Thirty years ago, business attire was a suit and tie; that was required to gain credibility. Today, a businessperson at any level can dress casually without necessarily losing credibility; the codes have changed.

It’s the same with business content: if you can communicate something succinctly, even as a meme, and it hits, you gain as much credibility as you would with a dense and lengthy article. (Think in terms of content capital.)

Consistency makes a creator

I always ask people how they define the term creator. Nobody has ever put it in quite the same words Adam did here:

Listen to the latest episode of Tasteland, the weekly podcast about media, tech, and business hosted by Spotlight editor Francis Zierer and Dirt Media CEO Daisy Alioto.

This week we’re joined by gambling writer David Hill, who just wrote "Sportsbook Nation” for Rolling Stone, an entertaining and in-depth look at the state of sports gambling in America in the wake of increased legalization across the majority of the nation’s states.