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Freewrite 2.0 - From The Founder

June 01, 2023 | 3 min read

Today we are launching two huge improvements to the Freewrite experience. The first is Freewrite Plus. It's a new paid tier of Freewrite services that unlocks new features on both Freewrite devices and in Postbox. The second is version 2.0 of Freewrite Firmware that will be available to all Traveler and Smart Typewriter Gen3 devices. I couldn’t be more excited to welcome you all to the next phase of Freewrite’s growth.

Freewrite Plus is our first step in providing premium features on top of the core drafting experience we have been refining since the first Freewrite devices shipped in 2016. The fact is that our vision to create the ultimate drafting tool was realized long ago. Writers have been using Freewrite devices to double their hourly wordcount consistently. Nobody needs new features to be prolific. Yes, it’s true. But what we realized, and heard from you, is that some writers just want more flexibility to be able to adapt Freewrite to their writing workflow. This is where Freewrite Plus comes in.

For all those looking to squeeze every possible ounce of productivity out of their writing experience, Freewrite Plus is for you. Today we are launching with two new features, document uploading and advanced send key functionality – more will be added to the Plus plan as time goes on. Stay tuned.

Document uploading is one of the most requested features we’ve heard from you all over the years. We’ve always said, since Freewrite is a drafting machine, not an editing machine, why do you need to upload drafts? Just start a new draft on your device and piece it together with the old draft on your computer later during the edit process. This is still the recommendation for most but for those that want that extra level of convenience of working directly in a previously written draft, now you can with Freewrite Plus.

The second feature launching today adds more options for sending drafts directly from the device. With the new firmware you can hold the [send] key down and email a copy of the active draft to any address. This allows for quick sharing of a draft, without going to a computer, to an editor or collaborator, and even the ability to print directly from the device (with a newer printer that has its own email address).

We haven’t forgot about the core Freewrite experience either.

The new firmware landing on all Traveler and Smart Typewriter Gen3 devices has a completely overhauled writing backend that works flawlessly with drafts of any size, from 100 words to 1,000,000. It looks the same but under the hood it is completely rebuilt. Until now, we've had to recommend people to start a new draft as their word count eclipsed 10,000 in a single document. Truthfully it was a bit embarrassing for a product that was designed for long form drafting! No longer. Firmware version 2.0 works with drafts of any length seamlessly and without slow down regardless of word count. Here we go!

Since 2014, we've dreamt of creating the best productivity tools for the writing experience. In that time, we've built 3 generations of the Freewrite device that started it all, now known as the Smart Typewriter. We launched Traveler, a smaller, folding version with the same distraction-free writing experience. Just last year, we crowdfunded Alpha, the simplest product in our writing tool lineup. We built Sprinter for quick writing sessions in the browser. We created Writing Time Fridays where thousands of people every week receive a writing prompt in their inbox. And all along the way we have been refining the product experience with improved cloud software in Postbox and new firmware delivered seamlessly over the air.

Over the years, some have complained that we may have not always been as responsive as they would like. They aren’t wrong but please believe me that it wasn’t for lack of trying. The truth is, we have never had more than one customer service person (sometimes it was zero!) and we all were heads down building. For many years, we were in survival mode. Now in our 9th year of operation, I can say with complete confidence that our team is better than ever and I’m just as excited today as I was when the OG Hemingwrite concept first went viral in the fall of 2014.

Thank you for coming with us on this journey and your support. Update your devices to the new firmware and give Freewrite Plus a try with a two-week free trial!

- Adam, Freewrite Founder and CEO

September 02, 2026 6 min read

Kentucky farmer and poet Wendell Berry entranced readers across the globe with his poems extolling the power of knowing the natural world. 

For writers who want to do the same, there’s deep knowledge to be gleaned from Berry.

August 26, 2026 5 min read

Freewriter Mike Somerby left a lucrative marketing career in e-commerce to start a print-only literary magazine by and for Montanans. Yes, you read that right.

We sat down with Mike to find out how ... and why.

Mike Somerby identifies as a writer — with some reservation.

"I think all who write are 'writers,'" he says, "even if the writing itself amounts to a simple letter to a friend or a personal journal entry."

We couldn't agree more. And we're thrilled that this particular writer writes his essays on Freewrite. Maybe that's why we felt comfortable asking him:

What inspires a professional brand marketer to leave his 9-5 and jump feet-first into the literary world of Bozeman, Montana?

Luckily, he was happy to tell us.

AC: Before we get into the lit mag, it actually isn't your first foray into the literary community, right?

MS: For about ten years — the lion's share of my professional chapter — I worked, in some capacity, as a brand marketer. Last spring, while enduring a particularly grueling stint as CMO for a Montanan e-commerce brand (yes, those exist), I found myself revisited by the remarks of an old journalism school professor: from his perspective, journalism students who apply their storytelling talents toward PR and marketing have crossed over to "the dark side."

While I find this a touch heavy-handed, I get the point, and I believe his notion resurfaced to meet the moment: we live in a world sorely hurting for analog (human) creativity and high-quality longform.

So I quit, traveled west with my dog in a 1986 U-Haul I'd converted into a camper, and plotted.

Step one: I founded Pulphead, a lounge (named after John Jeremiah Sullivan’s seminal 2011 essay collection) where Bozeman writers commune and grind out their prose until 2 a.m. Entry is a flat $5, which comes with unlimited drip coffee and tea.

Step two: leverage the Pulphead regulars and its online following to secure contributors for my new literary magazine, ANEMONE. Thus far, everything is going to plan.

We live in a world sorely hurting for analog (human) creativity and high-quality longform.

AC: Why do you think it's so important to create and preserve these spaces for authentic writing?

MS: Writing is a solitary act. Nonetheless, younger generations, in particular, struggle to forge IRL community in the way older generations might understand as an ordinary facet of being human.

By building a space that is as homey as it is supportive of their literary interests, we’re not only helping these individuals find their birds of a feather, but also providing them with a dojo that mandates setting aside blocks of time away from phones, home lives, and the other distractions. Win-win?

Incidentally, Livingston boasts the highest per-capita concentration of professional writers anywhere in the country. Couple this with another statistic — that Montana has more bookstores per capita than any other state — and it becomes clear southwest Montana is as fertile a place as any to invest in literature and its related industries.


AC: That's so interesting. What have you learned from being in community with creatives in Bozeman?

MS: In terms of writing, I've learned plenty. What has excited me most, however, is what I’ve learned from a small group of Indigenous women who come to the shop to write poetry and make beaded clothing in the traditions of their respective tribes (most notably, Crow, Cheyenne, Shoshone).

This is a group I’d otherwise have limited opportunity to engage with outside of Pulphead, and learning about their traditions, beliefs, hopes — even a little vocabulary — through firsthand conversation has proved incredibly edifying.

AC: And you mentioned you've seen Freewrites pop up in Pulphead. You use one, right?

MS: Yes. About seven years ago, not long after moving to Montana from New York, I purchased an Olivetti Lettera 32 typewriter from eBay. It appeared that a romanticizing of my newfound remoteness had rekindled my interest in writing.

I loved the mechanical feel and distraction-free interface, but the inability to edit line by line proved a notable annoyance for a mind habituated to modern computers. A few years down the road, some digging for alternatives led me to a blog post about smart/electronic typewriters. Voilà.

I purchased a Freewrite Gen3 Smart Typewriter, and I've been hooked ever since.

AC: That's awesome. So tell us about ANEMONE. What is it?

MS: ANEMONE is a print-only magazine (printed in a traditional broadsheet newspaper format). As for for theme, broadly, the world as told by Montanans. Short fiction, creative nonfiction, poetry, reportage, photography, and visiual illustrations comprise the submission categories.

AC: Print-only!

MS: Print is only dying because we let it.

AC: Is there a story about the name?

MS: Most people know the word anemone to describe a family of flowers — a 200-plus-species family of buttercups, comprising varieties both wild and domesticated. Dubbed “windflowers,” their delicate petals are said to blow open in the breeze; the ancient Greek word anemos means “wind.” I was drawn to the metaphorical value of beauty and how it can be revealed to us through an invisible force.

To add another layer, when I was a boy my father and I would spend weekends at the beaches north of San Francisco, where I was born and raised until I was seven. We would study the massive turqoise, kelly green, and purple sea anemones clinging to rocks left exposed by the receding Pacific tides (as to why, I can't say, outside of them looking funny, almost alien). A good memory.

Finally, “Anemone” is the name of an exquisite song by The Brian Jonestown Massacre, an irreverent and controversial rock band led by Anton Newcombe, an obsessive creative who rejects the surrender of culture and art to commercial interests. The track has a hold on me. It's like a portal to another era.

AC: Why do you think this sort of analog creativity is important?

MS:  I'm told the unending deluge of digital interface is leaving humans less and less capable of “deep work.” Will we ever know the difference?

Will we recognize what a society incapable of deep work looks like compared with those that came before it? Or will the transition manifest as a gradual degradation of quality, much as Coca-Cola was slowly, but surely, divorced from real sugar, such that to taste what Coke used to be like, one must order a Mexican Coke, still made with real cane sugar?

For me, analog perspective (and any creativity wrung from it) is rooted in continuity, tangibility, lived experience, slowness, spatial relation, nuance, emphasis on process, and grace for imperfection — antithetical to one of replicability, speed, binary outcomes, predictability, and optimization.

I prefer the former, and I suspect those who prefer the latter don't read or write much — life is a beautiful, taxing mess, and good writers find merit in this duality.

For me, analog perspective (and any creativity wrung from it) is rooted in continuity, tangibility, lived experience, slowness, spatial relation, nuance, emphasis on process, and grace for imperfection — antithetical to one of replicability, speed, binary outcomes, predictability, and optimization.

AC: Who is invited to submit to ANEMONE?

MS: We do limit submissions to Montanans, past and present, though we will feature writers from other states should the content of their writing bear an obvious relation to Montana — a requirement not imposed on Montanan writers.

All information regarding submissions can be found at www.anemonereview.com, along with all other facets of the magazine.

August 26, 2026 1 min read

Love the Freewrite 500? Here are 3 more writing contests for competitive short fiction writers.

1) Writers' Hour Magazine Prompts

The London Writer's Salon (a global writing group — no London residence necessary!) regularly host a writing contest via their Writers' Hour Magazine. Want to know a secret? Their September theme is all about freewriting.

Join them for a free workshop, Introduction to Freewriting, on Thursday, September 3, and get all the details about the contest.

The winner of the contest will win something Freewrite-shaped. 👀

2) NYC Midnight Challenges

This organization (again, no affiliation with NYC necessary) regularly hosts short story contests. Their next challenge is all about writing a rhyming story.

Learn more and register here.

Note: NYC Midnight writing contests generally have a fee to enter.

3) Henshaw Press Short Story Competition

This short story competition is open to anyone over age 16. And the best part? There is a cash prize, and profits go to charity.

Learn more here.