🔴 Newsletter acquired! And bought back for $1

Today’s guest is Ryan Gilbert, creator of a newsletter called Workspaces. He created it as a sort of “proof of work” while trying to break into the tech startup world in 2020 — it worked.

In the years since, Ryan has built an email list of nearly 14k (and a Twitter following three times as large), successfully switched industries, and even sold the newsletter, before buying it back two years later. His is a unique story.

In this issue:

• 💵 The full story of Workspaces’ acquisition

• 💼 Successes and struggles selling ad space pre- and post-acquisition

• ⚖️ The pros and cons of keeping his voice out of the newsletter

— Francis Zierer, Editor

P.S. We have a podcast! Listen to our full interview with Ryan or watch it on YouTube.

“This is going to sound kind of weird”

This past May, two years after his newsletter was acquired by a company that also hired him to lead their content program, Ryan Gilbert learned he was being laid off. By that point, he had been working on said newsletter, Workspaces, for four years.

Rewind to 2015. Ryan has just graduated college with a marketing degree. He dreams of finding a role in the tech industry, at some exciting startup, but he has no connections, no in; he finds a job in the supply chain industry instead. It’s a fine career. He keeps getting promoted and earning raises, all the while applying for roles at various tech companies to no avail.

It’s April 2020 and the pandemic has created a work-from-home boom. Ryan, active on tech Twitter, starts seeing all these people “from Facebook, Twitter, starting to work from home,” sharing pictures of their setups. Some are elaborate, composed of thousands of dollars of furniture and electronics. Eames chairs, pegboards tiled with tricked-out mechanical keyboards. Some are simpler. A kitchen counter, a couch. But they’re all beautifully photographed, all representative of this world he hasn’t been able to crack.

At the same time, everyone is starting a newsletter. Ryan isn’t technical, but he can make a Substack. So he does. And he texts a friend, then working as an engineer at Facebook:

Newsletters open doors

Ryan didn’t think Workspaces would lead directly to a job offer, but he did think it might open doors leading to other doors containing connections that would.

It only took one year publishing Workspaces for Ryan to get his first break. The project was fun and easy to engage with; it wasn’t long until he had people lining up asking to be featured, so much so that he started sending two issues per week just over a year in. To this day, he receives new submissions at a pace far beyond what he can publish.

In issue #60, Ryan announced that he would begin working with a company called Journal (now Heyday), running content for them part-time.

Heyday co-founder Sam DeBrule was a Workspaces subscriber and had reached out to Ryan to write a Twitter thread on him just a month earlier. Now he was hiring him as a content strategist.

Then, in June 2022 — barely a year after Ryan got his first opportunity in tech — SaaS company Loops came knocking about an acquisition.

Monetizing other people’s workspaces

By the time Loops brought Ryan their proposal, he’d been monetizing the newsletter for over a year. Each issue, from the beginning, included a list of items in the featured workspace: hardware, furniture, stationery. Eventually, this would expand to software and anything else a guest cared to include.

Ryan started using Amazon affiliate links in issue #86. I asked him why he waited a year and a half to implement what seemed like an obvious play:

Of course, when he asked some of his guests how they’d feel about affiliate links and sponsorships in the newsletter, they saw no issue.

Affiliate links ceased under Loops’ ownership. Sponsorships also ceased, at least in plural — every issue from #179 on, the first one post-acquisition, now began with a banner: “Published By Loops.” This sponsorship predated the acquisition: they’d begun sponsoring Workspaces in issue #168.

Why sponsor what you can outright acquire?

Two days after the first Loops-sponsored issue, the company’s CEO messaged Ryan asking to hop on a call. “At that point, they wanted to either buy a bunch more sponsorships or look into acquiring the newsletter, which I wasn’t really interested in selling,” Ryan says.

There was no shortage of sponsorship demand, but balancing ad sales against rapid audience growth was proving to be a headache. He’d been selling ads in bulk — the previous sponsor had run for two months, or around 16 issues.

At this point, Ryan had been at Product Hunt — his first full-time role in this industry he’d been trying to break into for half a decade, remember — for under a year. He loved it and wasn’t looking to leave, but Loops proposed hiring him as part of the acquisition and giving him “the role I would have wanted after four years at Product Hunt.”

It was hard to say no. He’d taken a pay cut when he left the supply chain world and joined Product Hunt. And so he sold Workspaces — for “new car money, not new house money” — and accepted a new role as Loops’ Head of Content.

“They didn’t have to give it back”

Four years after starting Workspaces, three years after it had opened a first door into startupland, and after two years in his post-acquisition role, Ryan was laid off.

It’s part of the game; he was one of 11,011 people in the tech industry laid off this May (according to Layoffs.fyi). Startups inevitably make cuts and marketing departments are often among the first affected.

The project that Ryan had ridden all this way on was no longer his. He had no right to the Workspaces brand, the email list, the Twitter account, any of it. But, in the layoff call, his former employer offered to sell it all back to him for $1.

He accepted. There are conditions to the deal, Ryan says, one of which is that he’s not at liberty to describe them. But Workspaces is his; issue #420 was the last sent under the Loops banner. After that, during the re-acquisition period, he missed a weekend (the newsletter goes out every Saturday and Sunday) for the first time in four years.

Rebuilding in a changed industry

Since re-acquiring Workspaces four months ago, Ryan has been working to re-monetize.

Before the acquisition, he was charging $250 per ad slot, sending two newsletters per week, and reliably clearing $2k per month. Not bad for a little side project. He was booked out three months in advance and only spent about an hour on each issue. Now the audience “has doubled in size,” with open and click rates remaining consistent.

And yet Ryan “cannot sell sponsorships.” He hasn’t even increased rates to account for subscriber gain.

Selling for a second time and spinning up new projects

I asked Ryan what he’d change if he sold the newsletter again — and yes, he says he is “not 100% opposed to selling it again.” He’s even received multiple offers since he bought it back, but has no plans to sell anytime soon.

Ryan’s personal valuation is inevitably based in pride and emotion — this is something he’s spent years building — but also includes the personal-brand and network benefits the newsletter provides. Understandably, the offers he’s received do not price these factors in.

It’s been three years since Ryan left his last supply-chain industry role. Four-and-a-half since he sent the first issue of Workspaces. And he’s succeeded in breaking into the tech industry; it worked.

A new full-time role does not figure into Ryan’s immediate plans, but he’s working on a few projects. Last month he helped relaunch and is continuing to help publish This Week in Design, a newsletter a connection of his acquired this summer.

Just last week, he launched a new project of his own, H1 Gallery, in part because he was “embarrassed by the lack of side projects” he’d launched this year. It involves “featuring and highlighting the best marketing headlines on the internet,” as a weekly digest and he hopes it’ll be able to grow in much the same way he grew Workspaces: “piggybacking off of other people’s audiences.”

H1 Gallery has yet to publish its first newsletter issue, but it’s been a week since Ryan announced it, and some 500 people have signed up.

Before Workspaces, when he was unsuccessfully applying to tech industry jobs, Ryan says the hiring parties would ask him, “How can you help us?” and he would reply, “Well, I really can’t.” He didn’t know the shape of his offering or ability, how it fit into this world.

Looking at Workspaces and now H1 Gallery, though, Ryan’s role is clear: he’s a talented curator and producer. Maybe it’s the years he spent outside this industry looking in that honed this skill — he’s a keen observer with a well-developed taste for a particular tech-culture aesthetic. Also, quite clearly, he’s a newsletter specialist.

H1 and Workspaces are both billboards for other people. Guests often come to Ryan when they’re looking to build hype around a new project. “Honestly, it’s like a giant ad for yourself,” he says.

Ryan, by the way, has never featured his own workspace in Workspaces. And he’s yet to spend a single dollar of that “new car money” he received upon first selling Workspaces.

Connect with Ryan on X/Twitter.
Read and subscribe to Workspaces.

For the full story, listen to our podcast or watch it on YouTube.

And if there are any details you’re still curious about … just reply to this newsletter! We’re always happy to hear feedback and answer questions.

🎙️ It’s not possible to fit every topic we discussed in our conversation with Ryan in this newsletter. In this week’s podcast:

• 🐦️ How Ryan built and leverages Workspace’s 45k-follower Twitter account

• 📈 We discuss all the levers Ryan has used to grow his subscriber list

• 🔗 How Ryan has evolved his affiliate link strategy

Listen on your preferred podcast platform or watch on YouTube.

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

  • This week: Your hosts are joined by Ty Haney, founder of Outdoor Voices and, more recently, TYB and Joggy.
    
    Topics covered include gamifying community-building, building a tool that allows brands to measure community-building efforts, Founder Mode, and building digital-first vs. physical-first.
    
    Also: sports fans and Bostonians suffering.

• For more about newsletter acquisitions …

  • We interviewed Akhil Chauhan about his acquisition of The Writer’s Job Newsletter.

  • We interviewed Ali Abassi about selling AI For Work only six months after he started it.