We have long been concerned with the value of content to attract, convert, and retain customers. This was believed to be HubSpot’s rationale for acquiring The Hustle in February 2021 for a reported $ 27 million. The business-oriented newsletter had grown to around 1.5 million subscribers, all of them potential HubSpot users.
Adam Ryan joined The Hustle as a part-time advertising salesman in August 2016, four months after launch. He was president in February 2021.
Ryan is now an investor and advisor, advising companies on content strategies. He and I recently spoke and talked about The Hustle, a retail editorial, and more.
Our entire audio conversation is embedded below. The following transcript has been edited for clarity and length.
Eric Bandholz: You joined The Hustle early on.
Adam Ryan: It was pretty new when I got there. It started in April 2016. In August, four months later, I joined the team part-time.
Band wood: Then you headed sales. Beardbrand advertises in The Hustle.
Ryan: You were one of my first five-figure advertisers. But yes, I built the sales team and revenue model there. I did everything myself for the first eight months.
Band wood: Let’s talk about things behind the scenes. We all see this newsletter every day with a million or more subscribers. But few of us know what it takes to do that.
Ryan: The revenue model consisted almost entirely of advertisements. Although it started out selling event tickets. Hustle Con, the annual event for startups, used email to sell tickets. That was before I got there. Then they realized that the newsletter could be much bigger with advertising. We also understood that we could sell them pretty much anything if subscribers trusted us.
These days, the publishing industry often uses content to sell products. It is for this reason that Penn National Gaming, the gaming company, has bought the digital publisher Barstool Sports.
Band wood: Tell us about the process – developing the content and building the team.
Ryan: We needed great content and great writers. The first writer on The Hustle was Kendall Baker. He now writes for Axios Sports.
The other variable is subscriber growth. How do you grow? What are the channels? Organic? Paid? Influencer? You need to know how you are going to expand.
And then understand the ad inventory, the media business. It’s easier to start as a media company and then add trading.
Band wood: Don’t you lose the soul, the independence of a media company when it comes to selling your own products?
Ryan: It depends. The integration of gambling in Barstool Sports is authentic to them. I don’t think any Barstool reader will question that. If anything, it has upgraded the brand. But HubSpot’s February acquisition of The Hustle isn’t that aligned.
One of my favorite examples of a company I work with is Section4. It was founded by Scott Galloway, a professor at New York University. Section4 is an education portal. It democratizes commercial training through courses from top educators. Section4’s newsletter publishes Galloway’s business ideas. It’s widespread. It easily fits into the courses that represent the trading aspect. The newsletter strengthens the brand.
Band wood: How should traditional e-commerce or direct-to-consumer brands handle content?
Ryan: The content must match the products on offer.
For example, I work with a company called Pela that makes environmentally friendly phone cases. They are aimed directly at the consumer and are 100% digitally native. I worked with them to invest more in content. But not a blog. Nobody wants to read a blog. It’s more like what Beardbrand did with its YouTube channel. It fits the lifestyle of your brand.
Pela founded a media company called Everyday Eco, where people can get news and information on sustainability issues. It’s a longer halo game to build a bigger audience. You monetize with ads. So they stay cash flow neutral or cash flow positive, but in the long run they build a community of people who are interested in sustainability. Recently they launched a compost product for the kitchen and used the community to distribute it. They made $ 5 million in revenue in two days.
That is the power. But it has to be organic. It must match. Too many people are trying to force it.
The cheap way to get readers is to be crazy headstrong. That’s what sucks MSNBC and Fox News. They take extreme positions. Gen Z doesn’t care about these outlets. Generation Z people don’t care what you say but how you say it. You are a human being. You are friendly. You are personable, relatable.
My favorite examples of this are Jon Stewart and Jimmy Fallon. People watch and love them not for what they say but for how they say it. This is how you build a content brand – through your personality, not through crazy opinions.
Band wood: How do you like this voice?
Ryan: It’s super hard. Just record yourself talking to your best friend. Then listen to the recording – your turning points, your cadence. Train yourself to do this all the time. Maybe you’re a little polarizing, a little unconventional. But you will attract like-minded people. This is the beginning of a relationship.
Band wood: The things I tell my friends can lead to my being canceled. How do I know what to offer a wider audience?
Ryan: Use common sense. If I were to start a media company, I would have no restrictions on writers and content providers other than following the company’s values. The world is full of opinions and voices. If you start limiting your talent as a media company, you will end up with boring content.
Band wood: Let’s address newsletters, especially for e-commerce. At Beardbrand, we’ve got to a point where we’re losing as many subscribers as we sign up.
Ryan: Migration is difficult. Morning Brew, theSkimm, The Hustle – all the big ones have to do with churn. Ecommerce companies sometimes forget to put on their human hat. Why would you send a marketing email at 1:00 p.m. on a Friday? Do consumers open email at 1:00 p.m. on a Friday from a brand they bought from four weeks ago? No.
So, in order to fix the churn, you need to establish the purpose. When you create a purpose, you can create habits. If you make a habit of it, people will open your email and not unsubscribe.
Think from a deeper perspective as a human. The media is about attention. Trading is about buying. Getting these two to work together can be difficult.
Band wood: It’s hard, of course. Not many people do this well. We briefly discussed the structure of the team. You and your buddies built a team at The Hustle. It sounds like a disaster.
Ryan: Yes. Most people think I’m crazy. But I would do it again. It was the best time of my life. Work with people you love and share their values. I used to wake up at 3 a.m., not from stress but from excitement about going to work.
Working with friends certainly had its drawbacks. Some people I’ve lost touch with. That was difficult. I had tough conversations with others when they weren’t producing. It is not easy. But when you can work day in, day out with some of your best friends for three or four years, this is a rare opportunity. I couldn’t do without it.
Band wood: What does the future of the media look like?
Ryan: Creators have a moment. Platforms like Substack, which help creators monetize content through newsletters, are exploding. Instead of helping brands, creatives make their own money.
But they are creators. How do you manage sales and operations? What are your goals? A lot of these people just want to make content. They don’t want anything to do with the money side. Others say, “I can make life changing money. How do I step on the gas? ”So the goals vary between creatives.
There are two aspects of media that I find exciting. I see local as a great opportunity, mostly through trade, helping local businesses sell more in their area.
And then B2B, industry-specific content. Trade publications have been enormous for so long. You see a lot of people who are after this room. Substack is a breeding ground for industry professionals who have the time to write a weekly newsletter.
So these are two of the things I’ve played with.
There is now an opportunity for ecommerce brands. If I’m at a watch company, I am probably interested in receiving a killer newsletter from someone who is passionate about watches. You will see many opportunities to acquire these types of content providers. And it’s not about pushing a brand, but about building sales.
Band wood: How do brands rate these opportunities? How much are they worth?
Ryan: It’s part heart and part science. Most of them don’t monetize. As acquisition candidates, I classify them in two ways: those who build a brand and those who promote themselves. You have to evaluate them differently. There is only so much you can do with a newsletter tied to one person or personalities. But you can do a lot with a brand.
Band wood: What kind of valuation mathematics is that?
Ryan: It depends on the lifetime value of the acquirer’s customers. The higher the LTV, the more a subscriber is worth. A low LTV product could be worth $ 1.50 or $ 2 per subscriber. A high LTV brand can afford $ 5 or $ 6.
Band wood: Where can people find out more about you or contact you?
Ryan: I’m on Twitter, @AdamRy_n. My website is AdamRyan.com.