Scott Galloway had the audience. Here’s what he came for.

Scott Galloway is a professor of marketing at NYU Stern School of Business, a serial entrepreneur, and, for the past decade, a writer, podcaster and media founder. No Mercy / No Malice, the weekly newsletter he started as a testing ground for book chapters, now goes out to more than 400,000 subscribers, and his media business, Prof G Media, generates roughly $20 million a year in podcast revenue across his portfolio. His reach among the 25-to-54 demographic, he told us, beats the most-watched shows on CNBC.

No Mercy No Malice lived for most of its life passed around a series of email platforms that, as his team describes it, were built for enterprise marketing departments. For the year and a half before they came to Substack, another newsletter, Prof G Markets, was running on beehiiv. In March, the team made the decision to consolidate everything under one roof, bringing a full portfolio of newsletters, video, livestreams, and new subscriber-only content to Substack. In the two months since, they’ve launched three new newsletters and are preparing to debut The Week, a Friday roundup across the Prof G universe. Starting May 27, Jessica Tarlov of Raging Moderates will be co-hosting a weekly livestream with Aaron Parnas of The Parnas Perspective, their first Substack-exclusive show. “For the first time,” his team told us, “we’re supported by a platform purpose-built for content creators.”

We sat down with Galloway after his first two months on the platform to hear what this subscription revenue has unlocked for him and why he projects that Prof G Media will reach $1 million in ARR on Substack by the end of the year. He was characteristically direct about where media is going and about what it actually costs creators to build on platforms that hold the leverage—where your margin, as he puts it, is their opportunity. He is also honest about what’s hard, what he hasn’t figured out yet, and why he thinks the real test is still ahead.

You’ve been publishing the first of your weekly newsletters, No Mercy / No Malice, for what will be 10 years this summer. What were you first hoping to build when you started?

I just enjoy writing, and I used the newsletter as a kind of petri dish or incubator for chapters for a book. I would have a thought about something and just write. It was literally me at midnight on a Thursday writing something. Usually the top was business-related and the bottom was more personal. It was me punching out something Thursday night as a means of exploration, and it was just cathartic.

Did weaving in personal stories feel intuitive to you from the start?

I enjoy writing about family and my sons. I sometimes write about topics that upset people, or people find my content not in line with what they were expecting, or sometimes I just get it wrong. There have been a couple of seminal business moments [in the newsletter]. I wrote a piece saying WeWork was ridiculous. I got the S1 and wrote up an assessment saying it was a ridiculous idea that this company was going public and I think we’re credited with being one of the forces that stopped the IPO. So there have been some important business moments. But immediately it was obvious that the thing that resonates with people is the personal stories. The most-read post I’ve ever published was a post I wrote about putting my dog down. There’s a wide space for men of my age to talk about their emotions.

The WeWork story makes me think about risk-taking and being publicly outspoken. How do you evaluate what risks are worth taking?

I don’t do a risk assessment. I believe what Sam Harris said: if you have economic security and people who love you unconditionally, you have an obligation to speak your mind. I think when I say something off-mark or wrong, that’s what people enjoy the most, because it gives them a chance to weigh in. I try to write as if the only people who are going to read it are my kids in 20 or 30 years. I want them to understand me better and the world a little bit better. But I try—I can’t always say I do it—I try mostly to ignore the comments. I talk about money, about a lot of my personal failings. I know it resonates with people. There’s a real danger in getting too caught up in thinking about what your audience is going to think of what you’re writing, as opposed to what you actually think is going on.

If not the audience, who serves as a check on you?

You need [checks and balances]. It’s important to reflect. Prof G Media is 27 people, and there are a lot of people in the company who tell me when I’m wrong or disagree with me. The newsletter has evolved dramatically. As my following grew, the number of people working on it grew, because now it involves a lot of data. I take the responsibility seriously that 400,000 people are reading it, not 400. You have a responsibility to do more fact-checking and review it more carefully. It used to be literally me at midnight on a Thursday giving myself 90 minutes to bang something out, and publishing it with the typos and a few charts. Now there are probably three or four people who touch it before it goes out. Graphics. It gets a host read-over. It’s its own podcast now. I have a lot of people who, quite frankly, save me from myself on a regular basis.

You built out your consulting firm, L2, specifically to maximize enterprise value, then sold at a significant multiple. Is that a model you’re trying to replicate with Prof G Media?

When I was 26 in business school, I started a strategy firm. After about eight or 10 years, I wanted out. We were doing $10 million in revenue. I sold for $33 million—3.3 times revenues—which is fine, but it was transactional revenue, not recurring revenue. When I started L2, I got a study from Deloitte that had looked at outcomes of private company transactions. They sussed out that companies whose exit multiple was in the top decile typically had four features: recurring revenue, they owned a niche, they had defensible IP, and they were international. So from day one, I set up L2 that way. Instead of charging Nike $800,000 for an engagement, I charged them half a million dollars a year for a quarterly membership.That company got bought for eight times revenues.

With Prof G Media, to be blunt, I’m economically secure. I want to do something I enjoy. But the business is doing really well, and I recognize that people working at Prof G want to have their own houses and cars and college funds. About two years ago, I started thinking there’s enterprise value here. Key to that business is subscription revenue.

Our business does about $20 million top line in podcast revenues, but that business has a multiple of probably two to three times. We just started on Substack and wanted a subscription offering. My guess is we’ll be at an ARR of about a million dollars by the end of the year. That revenue has probably a four to six multiple. In addition, the entire company trades at a higher multiple when subscription revenue is growing faster than your core business. Substack’s role for us was to diversify the revenue mix and create a more valuable one. That’s the entire rationale and motivation for going on Substack.

How would you describe what you’re building on Substack?

We found on YouTube and other platforms, you have to be pretty vertically focused. What we wanted with Substack was a repository for everything we do, because we try to bring a voice of education and insight. We want people to learn and feel like they’re getting real insight, and also entertainment. We try to be funny, irreverent. We wanted a repository where someone could come for all things from Prof G Media.

The two biggest subscriber drivers so far have been our interview with James Talarico and Mia Silverio’s deep dive on storytelling—she puts together all my decks for my presentations. We’re still learning. I don’t know if I would have guessed those things would drive subscriptions. We’re adding about 150 paid subscribers a week, and a lot more unpaid. Have we cracked this nut? I don’t think so. We’re five or six weeks in. We look at people we admire, like The Bulwark or