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Going paid: How Stuart Winchester found product-market fit with skiers


We invited Stuart Winchester, writer and podcaster behind The Storm Skiing Journal and Podcast, to share his insights on launching a paid publication. At a live session for Substack writers, Stuart walked us through how he built his free list using social media, teased his paid launch, and converted paid subscribers. 

Credit: Harley Hall Photography. Pictured: Stuart Winchester at Plattekill ski area.


Clarify your audience and opportunity

In Stuart’s day job in the entertainment industry, he watched journalists cover the companies he works for in a really analytical way. Ski media, which predominantly focuses on “ski studs jumping off hundred-foot cliffs,” lacks this kind of analysis. His Substack, Storm Skiing, covers the “brains” of skiing, the business and history of ski resorts and mountains. Stuart describes his audience as “the 99% of skiers that spend 99% of their time skiing off a lift at a ski resort, not jumping off cliffs in Alaska.” 

Grow your free list with quality posts and promotion 

Before going paid, Stuart built up his list to 5,000 free subscribers by sharing exclusive coverage on ski resorts and promoting on social media. The tone and motivation for posting on each social media platform differed. 

  • Facebook Groups: “I found the most growth from Facebook Groups. No matter what you’re writing about, there’s probably Facebook Groups that are aligned with it.” For skiers, there are many subgroups by region and type of ski pass. “I just tailor whatever the story I publish is to the group.”

  • Twitter: “I have a little Twitter following. I use it mostly to break news and tease the newsletter.”

  • Instagram: “To use a skiing term, I use this more as a ‘stoke’ channel.” Stuart posts pictures and short anecdotes here.

  • LinkedIn: Stuart sums up his podcast on LinkedIn from the business point of view. “People on LinkedIn want to know what’s the strategy and what’s the mindset of people that are successful and thinking differently.”

Tease your paid launch

Every year, Stuart shares an anniversary post. In the post celebrating two years of Storm Skiing, four months before Stuart went paid, he mentioned that he would introduce a paid tier.

Eventually – probably within the next year – I will enable paid subscriptions. Some content, including the podcast, will remain free. But some will not. I welcome any thoughts on this potential change as well.

“I got a lot of feedback from people saying, ‘Hey, we love it. We’re in.’ ”

Read more: The Storm Turns 2 Years Old, Expands Nationally

Make the paid-launch moment urgent and enticing to readers

In February 2022, Stuart announced to readers in a post that he was officially going paid. He borrowed the payment model of ski passes and offered an early bird period.

For the next two weeks, you will be able to lock in a price of $6 per month or $50 per year. Individuals who wish to show extra support for The Storm and independent ski journalism may contribute more through a special “founding member” tier. On March 14, the price will increase. I may run occasional sales or holiday specials in the future, but the price will never be lower than it will be for this introductory period.

In the same post, Stuart promised readers consistency, quality, and relevance. When it comes to consistency, he makes a promise that is sustainable for him and valuable to his readers. “I see a lot of writing about newsletter burnout and these schedules where writers say, ‘I’m going to post twice a week on Friday and Monday.’ I’m not doing that. I’m doing 100 posts a year. That’s something I know I can do.” He’s proven he has the capacity to follow through on those commitments, and it has created flexibility for his personal life.

Read more: The Storm’s Partial Paywall: What It Means, How It Works, & Why It’s Happening

Remind readers

The first launch post drove 279 paid subscriptions. On the final day of the two-week early bird period, Stuart brought in another 123 paid subscriptions. Stuart ended up extending the deal 24 hours and nudging readers one final time, which brought in another 50 subscriptions.

To read more writer advice on going paid on Substack, visit our Going Paid interviews with Edwin Dorsey, Courtney Martin, Christopher Curtis, Illyanna Maisonet, and Camila Russo.

For more information, visit our checklist, which documents the essential knowledge writers need to turn on and grow their paid subscriptions on Substack.

On Substack
Going paid on Substack: A checklist
Feeling ready to turn on paid subscriptions? Or perhaps you are curious about what’s involved. This checklist documents the essential knowledge writers need to turn on and grow their paid subscriptions on Substack. Download a PDF copy here: Step 1: Update your marketing…
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On Substack
Tips, ideas, and resources for writers.