Ep. 73 How To Have More Fun In Your Business w/ Deanna Seymour

When did you last do something in your business that felt really, really fun?

If you are struggling to think of an answer, you are not alone. Most of us start our businesses with a genuine spark, excited about the work, excited about the freedom, excited to finally be doing something on our own terms. And then somewhere between the content calendars and the client deliverables and the taxes and the 45-minute TikToks that turned out terrible, that spark quietly dims.

Deanna Seymour is a graphic designer, founder of The Playhouse and one of the most genuinely fun people in the online business space. She has built something pretty unusual: a virtual social club for business owners who prefer real connection over constant content. In this conversation, we got into how she got here, why she thinks most of us are massively overthinking our marketing, and what it actually looks like to run a sustainable and enjoyable business without burning yourself out trying to do all the things.

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Deanna's Story: From Art Teacher to Online Business Owner

Deanna has always been creative and has always dabbled. Before building her current business, she taught art, taught punk rock aerobics, and ran a business called Missing Monsters selling little plush creatures and upcycled kids clothes. Classic ADHD entrepreneur energy.

When she transitioned into online business, she started the same way most of us do: taking any client who would pay her, offering a little bit of branding, a little bit of graphic design, a little bit of website help. Over time, that simmered down to something more focused. She now primarily helps service providers set up static nine-grid Instagram pages, what she calls a "body of work" approach to social media, so they can spend less time grinding out content and more time doing the actual work they love.

Her whole philosophy centers on one idea: service providers are not influencers. We do not need to be churning out content constantly. We need to show our best work, attract the right people, and have enough time left over to actually serve our clients.

The Problem with Constant Learning

One of the things Deanna and I bonded over immediately is something that does not come up enough in online business conversations: the point at which you have to stop consuming and start doing.

There is a stage early in business where you genuinely need to learn everything. Which platform to use, how to price, how to show up. That learning is valuable. But there is another stage, the one both Deanna and I are in, where adding more information is actually making things worse. You pick an email platform and it is working fine, and then you listen to a podcast and start wondering if you should switch. You have a content strategy that is sort of working and then you hear about a new format and get distracted. You end up with muddy brown paint because you kept mixing wet paint on top of wet paint.

At some point, you have to declare that you have picked your platforms and your systems, and that you will stick with them until they are actually broken, not just until a shinier option comes along.

The platform debate is a good example. Kit versus Flodesk has been one of the most exhausting ongoing conversations in online business. Deanna and I both agree: it does not matter. Pick whichever one you will actually use. The only email marketing platform that is wrong for you is the one you do not send emails from.

The Playhouse: What Happens When You Build What You Actually Want

Deanna's current membership, The Playhouse, did not come from a gap in the market analysis or a strategic pivot. It came from a book.

She read Rainn Wilson's Soul Boom, which makes the argument that a lot of us threw out the spiritual baby with the religious bathwater. We stopped going to church or temple or wherever our community used to live, and we never replaced the thing that mattered about it: the fellowship, the shared meals, the regular gathering of people who genuinely know each other.

Deanna wanted that. A non-church church. A community center for online business owners that was not about learning another framework or absorbing more content, but just about hanging out with genuinely good people.

The Playhouse Collective started with around 20 to 40 members. Events include live training from members who know their stuff (full disclosure: I have hosted live brand audits in there), book clubs with themes like "something pink on the cover" or "one word title," Bravo TV recaps, and pretty much anything else members feel like hosting. The running joke is that if you have hot takes on Real Housewives of Salt Lake City, there is a place for you in the Playhouse.

But underneath the fun, something genuinely valuable is happening. Members are getting to know each other in a way that a month of Instagram reels could not replicate. Real relationships are forming. People are hiring each other. When someone from the Playhouse reaches out to me, there is already an established baseline of trust that skips past a lot of the early getting-to-know-you friction.

In a business landscape where buyers are more skeptical than ever and the time from first awareness to actual purchase has gotten longer, that kind of relationship-first community is not just fun. It is one of the most effective forms of visibility there is.

Stop Doing the Things You Hate

This might be the most important thread running through the whole conversation, so I want to say it plainly: stop doing marketing activities you genuinely hate.

Not because it is too hard. Business has plenty of hard things that are worth pushing through. But because if you are creating content in a format you despise, it shows. Your audience can tell. Buyers are smart and they are discerning, and someone who is grudgingly filming a reel with the energy of a thirteen-year-old being asked to empty the dishwasher is not building trust with their audience. They are actively eroding it.

Deanna uses a great analogy here. She can commit to eating Cheetos every night without any problem because she enjoys it. She cannot commit to going to the gym every day because she does not. Consistency comes from doing the things that you are at least willing to do, ideally the things you actually enjoy. You get better at things by doing them repeatedly, and you will only do things repeatedly if they do not make you miserable.

That said, there is a difference between "this is new and uncomfortable" and "I fundamentally do not want to do this." Deanna gave TikTok a real shot and decided it was not for her. That is fine. She loves podcasting. So she podcasts. The format you will actually show up for consistently is worth more than the format some guru told you is currently winning the algorithm.

And if there is something in your business you genuinely have to do but hate, think about how you could make it more fun. Deanna used to hate bookkeeping until she started co-working with friends to get it done. She turns it into a social event with a little chat at the beginning and end, and suddenly it is something she can actually follow through on. The thing does not have to change. Sometimes just the context around it does.

What I Have Noticed as a Member of the Playhouse

I joined the Playhouse in its early days, honestly not expecting much. Deanna sent me a Google Doc. There was no polished sales page. I paid something like $97 for a full year and thought, sure, let's see how this goes.

That was almost two years ago. I am still there and it is one of the two or three communities I genuinely recommend when people ask what is worth joining.

What keeps me there is not the content or the curriculum. It is the people. Deanna has done a genuinely exceptional job of attracting the kind of business owners who are both talented at what they do and kind and generous with their knowledge. I have had people come to back-to-back brand audits I hosted, implement the feedback in between sessions, and come back to show me the results. That kind of engagement usually costs money. In the Playhouse, it just happens because the community culture supports it.

In January, Deanna opened a free audience tier, and in just six weeks there are already about 100 people in it. The idea is essentially that the paid collective members are the improv troupe on stage, and the free audience tier gives them somewhere to invite people to come see a show before deciding if they want to get on stage themselves. It is a smart, low-pressure way for people to find the community before being asked to commit to it.

The Honest Truth About Running a Membership

Deanna is refreshingly honest about this: growing a membership is hard. It is not passive income. It is not "build it and they will come." She describes the tension between wanting to focus on making the experience incredible for the people who are already there and needing to keep finding new people to bring in.

Her approach has been to keep the Playhouse low-lift in terms of content production. She is not churning out training after training every month. The events are largely community-driven, which means she is not the only one creating value, and that makes the whole thing sustainable for her long-term.

She also keeps the price accessible intentionally. Not because the value is not there, but because the Playhouse is not meant to be a high-stakes learning investment. It is meant to be a place you show up because you want to, not because you paid so much that you feel obligated to justify it.

The result is a community that has now been running for almost two years and keeps growing organically, largely because the people inside it talk about it to their friends.

Which is, as I have been saying on this podcast for a long time, the best marketing strategy there is.

🔗 Links & Resources Mentioned In The Episode:

➡️ Join The Playhouse
➡️ Connect with Deanna on Instagram @thedeannaseymour
➡️ Follow me on Instagram @spechtand.co
➡️ Book Your Stand Out Brand Strategy Session (use code SFBPOD for $100 off)
➡️ Book A Brand Chat

🎧 Listen to episode 72 of The Six Figure Brand Podcast on Spotify, Apple Podcasts, Amazon Music, and YouTube