Catching up with WhereBy.Us: On building Letterhead, a newsletter platform that your company can use, too

When COVID hit the world at warp speed last year, WhereBy.Us the parent company of The New Tropic and a handful of other hyper-local newsletters across the country – found itself in a precarious position: With upcoming events canceled, the Miami-based company’s once oversubscribed ad sales dried up quickly.
The team looked to its existing readers, most of whom didn’t pay a membership, for support.
“In the early days of COVID, we contacted our readers and said, ‘Hey the economics have changed, and it would be great to have your support,” Chris Sopher, WhereBy.Us’ CEO, said in a phone interview.
“Our readers stepped in in a big way, so we saw our membership program grow by 300% this year.”
The venture-funded startup, co-founded by Sopher, Rebekah Monson and Bruce Pinchbeck in 2014, kept its brands afloat, but in the meantime, the startup was brewing up another product that would provide an additional revenue stream.
“People would reach out to us and say ‘I love this newsletter, what tools do you use?’” Sopher told TechCrunch. “We’d tell people that we used our own internal tools and they’d say ‘oh, can we use those, too? And we’d say ‘no, that’s not what we’re doing.’ Eventually, we said no enough that we looked at each other and said, ‘we should figure out how to get to yes on this’. “
The WhereBy.Us team spent years developing the tools to send the perfect newsletter, and now the team has made those tools – and the built-in advertising capabilities – available to other companies through their new newsletter platform: Letterhead.
You may be thinking, “Letterhead sounds a lot like Substack,” but there are a few key distinctions. While Substack is built more for a single writer who wants to monetize a newsletter by charging a subscription fee, LetterHead is designed for businesses or organizations where the newsletter component is only one piece of the business. Additionally, with Letterhead, the company can also sell advertising within the newsletter.
“What we’re seeing is that people outgrow Substack,” Sopher said, pointing out that what might start as a single writer business, if successful, can quickly become a team of writers.
Sopher said the Letterhead team is piloting an advertising program in Miami, where a dedicated ad sales team works on behalf of Letterhead subscribers to place ads at various 
LetterHead’s client’s newsletters. The idea was born when The New Tropic attracted more ads than it could feature.
“In Miami, we started to fill up The New Tropic and had more advertising than we had room for,” explained Sopher. “People always hear about companies that help them drive revenue, but we’re actually doing that,” he added.
Letterhead starts at $100/month on an annual plan, but the startup is rolling out a starter kit soon that will be less expensive.
“Our goal is to make it really, really affordable,” Sopher said.
Photo at top of post of WhereBy.Us co-founders Chris Sopher, Rebekah Monson and Bruce Pinchbeck is by  Ayubi Photography.

Marcella McCarthy