The longer you go in your career, the more you’re in sales.

I’m going to take a break the next two weeks in the run-up to Labor Day. That will allow me to spend a bit of time on planning, figuring out a new podcast concept and preparing to move – always a fun experience.

I tried a shorter version of the newsletter this week. It’s summer, and I got a note that politely encouraged a few forays into brevity. I need to heed my own advice.

Chronicles of an ad salesman

It was my first job in journalism when my boss, Jason Calacanis, introduced me to the cliche “sales solves everything.” No matter the problem with a business, you can be sure it will be better if you’re getting sales in the door.

One of the good parts of starting from scratch is you get to do every job, particularly sales. Outside of Orlando’s Bakery, I’d pretty much never been in a sales role. I was more inclined to the back of the house. Some early lessons in my sales stint the past 18 or so months:

Everyone’s in sales. The truth is, the longer you go in your career, the more you’re in sales. I don’t care what your role is, but if you progress beyond an individual contributor, you’re in sales. You’re either selling initiative internally, both above you and to your team, or you’re trying to recruit the best people, more sales. Even the act of writing to me is sales. You’re trying to create unique value and connect with people in order to persuade them. I’ve chosen to take pretty much the same approach I’ve always taken to journalism: Listen more than talk, and focus on trying to find the important bit from all the unimportant that often shrouds it.

Finding alignment is key. In my view, you need to pick a lane. You can either be an efficiency play – I can get you those leads cheaper, and I’ll guarantee it! – or you can be an influence play. I want to do the former, mostly because I’ve chosen to make a product that’s free of the filler that others use to pad their numbers and show up nicely on a spreadsheet. The best partners understand that.

Understanding what people want is hard. The reality is a lot of times people don’t know for sure. The best partnerships are ones where you work together to find that alignment and where value can be created. People often fall back on spreadsheets, and generating leads is paramount in most B2B marketing, but I find most partners want to align with The Rebooting because the ethos matches with how the partner sees the industry.

Avoid land wars. Revenue is oxygen. And yet at a small scale – and it doesn’t get smaller than 1 – you need to be judicious with your bandwidth. I understand the purpose of “test budgets,” but they’re often a mismatch with small publishers because the administrative burden eats away most of the margin.

Selling is a lot easier when you believe in your product. I always say you have to find your points of leverage. Business is all about leverage. You either use the leverage you have or try to create an illusion of leverage. With no sales experience, a small audience and a new product, I knew a lot of the leverage I didn’t have. But what leverage I did have is it’s unique for the maker of an editorial product to also be the seller. The biggest point of leverage from that is I truly believe in what I’m selling. It isn’t something that was handed to me; it’s something I made. I’ve found that develops a more human connection, not just on the audience side but also with partners.

House of Kaizen collaborates with publishers worldwide to build more sustainable businesses with best practices and experimentation for better acquisition, retention and lifetime value. Matt Cronin, founding partner at House of Kaizen, gives his insight into the critical challenge of subscriptions: keeping customers.

While a subscription business may think of each new customer in terms of their subscription duration, the new customer is thinking of it as a trial – particularly so if they have come to it with a discounted offer or a low CAC strategy of acquisition.It’s at this point where we’ve seen a well-designed and continuously optimized onboarding experience have the greatest impact on retention and CLV. Learning how to get the most from their new subscription and establishing the habits that will deliver on the marketing promise is the best way to shift the trial mindset into the subscriber journey.

Learn more about how House of Kaizen helps publishers build sustainable subscription business lines — and get in touch with Matt directly.


A big test for Axios’ local ambitions is if it can find a recurring revenue model. Scaling national ads to the local level is tough, and local advertisers are hard to reach and tend to have small budgets. Things like job boards can help, but that’s in the incremental bucket. I’ve been checking out the new Axios Miami publication, and I noticed Axios is testing a voluntary contribution model. (The main benefits are around supporting local journalism, with a few extras like a quarterly newsletter. As Axios says: “But these benefits are not why you should join. You should join because you want to support the work.” The Guardian has shown this can work on a large scale, but there are also many other instances where this works, albeit more often with individuals rather than big companies that just sold for $525 million.

For all the deserved grief that platforms like Facebook get for polarization, cable news is a bigger culprit. And before that, I recall the moral panic over talk radio. And I’ve long felt that one of the biggest sources of misinformation among older people is the old-fashioned forwarded email.

If you speed-read through the introspection on being the subject of ridicule on Twitter – does not great – Charlie Warzel has an interesting piece about the implications of AI illustrating tools like DALL-E. My initial reaction was how amazing and “democratizing.” But I hadn’t thought of the illustrators who might get displaced. I believe there’s always room for craft, but I can see the concerns of illustrators, since there’s already a bot churning out passable real estate copy.

Apple’s move to upend a big chunk of digital advertising will continue to have repercussions. The status quo in ad targeting is ending, with Apple’s moves in the name of privacy, regulations and the eventual (maybe?) phaseout of the third-party cookie. Ben Thompson and Eric Seufert get into the weeds on the second-order effects of Apple’s app-tracking transparency. What Eric calls the “digital marketing winter” will be many marketers needing to become more immersed in real marketing versus staring at dashboards and attribution tools to shift their bidding around.

Accountability is something that people like in the abstract and mostly for others. But it’s critical to avoid systems where people cover up mistakes and shortcomings. I was glad to see the CDC begin – and there’s more it needs to do – to face up to the obvious bungling of many phases of the pandemic. Everything I’ve read points to an insular, overly abstract organization more inclined to obsess about process than take action. Ideally, the entire pandemic response at all levels will get similar scrutiny.

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