About The Playhouse...

This is a space for solopreneurs to feel less solo while growing a business they don't end up resenting.

It's a space for creative business experiments, honest stories, and pep talks. Most importantly, it features The Playhouse Gang, creative, curious, slightly rebellious business owners who are growing businesses that do good in the world.

It's like the coworkers you used to talk shit with in the breakroom, or the people you met up with after work for chips and guac at happy hour. 

You could meet your next collaborator, client, or best bud. But at the very least? You'll see the beauty and humor in your business journey, cause this shit's hard, and if we don't laugh, we'll all be crying. 🙃

Vintage TV with a photo of The Playhouse Gang from Pee-Wee's Playhouse
Remember The Playhouse Gang from Pee-Wee's Playhoe (baby Natasha Lyonne)

🦖 Choose Your Own Adventure

Whether you just want some great stories in your inbox or you're looking for your next business friend or collab opportunity, we got you boo.

💌 The Free Newsletter
Get raw, honest stories, business ideas, and insights from me and fellow members delivered straight to your inbox. Perfect if you just want to read along and get a feel for the vibe.

⚡️ The Playhouse Gang
Ready to hang with us? Paid members unlock the ability to comment on posts and swap ideas directly with other Playhousers.
You also get...

  • Extended Podcast Episodes & Premium Posts: The deeper, unfiltered strategies.
  • 4 Seasonal Mixers a year: Virtual gatherings to clink glasses and make introductions.
  • DD's Vault: Access to any business templates or training resources I create.

🏠 The Playhouse Heartbeat Community
Once you're a Playhouser, you'll get an invitation to step inside our private Heartbeat space. This is our active, daily digital breakroom that includes:

  • Coworking: A 24/7 virtual coworking room so solopreneurship doesn't feel so solo and lots of coworking on the calendar so you can plan ahead.
  • Thursday Meetups & Monthly Matchups: Structured ways to get introduced to your next collaborator.
  • Threaded Forums: For active chatting, pitching ideas, asking questions, getting feedback, and celebrating wins in real-time.

Meet Deanna Seymour

I'm a lifelong creative that belives collaboration and strong community makes all the difference.

I went door-to-door selling painted pinecones to my neighbors in first grade. So I guess since '87 I’ve been on a winding path of creativity and entrepreneurship.

  • Teaching art classes + workshops for 13+ years
  • Running an Etsy shop + schlepping my ass to craft shows in Brooklyn, Baltimore, Richmond, Charlotte, and DC
  • Curating local art shows + fundraisers for causes I care about
  • Hosting punk rock aerobics in a vacant building downtown
  • Writing for Richmond Moms Blog about how hard parenting can be

And now, I run The Playhouse with over 100 amazing humans who happen to run online businesses - but I assure that's not the most interesting thing about them.

We're a mix of anti-hustle, feminist, creative, introverted, highly sensitive, neurodivergent freaks and geeks who run businesses that put people over profits and want to do good in the world.

A collage of lots of Deanna Seymour's artistic adventures through the years.
Some of my creative ventures and community events over the years...

💖 You're more than your business bank account here

There's a lot of messages out there about growing your business fast and big and if can make you feel really behind.

As Marcel the Shell said, "Sometimes you just have to disregard those rules and think, well, actually the rule is that I want to be having a good life and stay alive, and not just survive, but have a good life."

We're building profitable businesses here, and havin' good lives.

a shell with google eyes and shoes on a brick ledge with a peeling wooden background
a shell with shoes I made with my niece a long ass time ago