Big Fun, Small Business: An audio sketchbook for building a business that feels good

Deanna Seymour | Graphic Designer + Community Founder
  • 5.0 (16)
  • Marketing
  • Updated Biweekly

Humans evolve. Ideas change. And honestly, how is a creative human supposed to stick to one podcast idea for half a decade and a ton of episodes? I have no idea. That’s why Big Fun, Small Business is an audio sketchbook of all the things I’ve explored since starting back in 2020. It’s a collection of ideas, rants, pep talks, tips, and a very real evolution of what it looks like to build a business when your values are rooted in experimentation, creativity, and being true to yourself. Some episodes might have old ads to products I tried that don’t exist anymore. But for someone who started with a podcast called Imperfect Party, I say eff it.  This audio sketchbook celebrates the mistakes, the pivots, the tears. It’s a journey, and kind of a wild ride. Because no matter what a well oiled sales page tells you, running a business is hard, but it can also be a lot of fun. If you hear something you want to chat about, I’d genuinely love to hear from you. You can email me anytime at deannaseymour.com. And if you want to hang out beyond the podcast, you’re welcome to join my free community, The Playhouse, at jointheplayhouse.com. Happy listening! 🎉💖

  1. 10/03/2025

    Building Trust, Pricing for Profit, and Collaboration over Competition with Emily Reagan

    What’s the simple way service providers can stay booked without posting 24/7? In this Friends of the Playhouse episode, Emily Reagan, founder of Unicorn Digital Marketing Assistant School and the Digital Marketers Work Group, shares practical ways to market yourself without the influencer grind. You’ll hear why owning your role as a business owner changes everything, how collaborating with other service providers leads to better clients, what to do if referrals are your only pipeline, how to talk about your work with confidence, and a reframe that makes selling feel like helping. We wrap with a quick This or That: Service Provider Edition… raise your rates or tighten your boundaries? Learn more about Emily on Instagram at @emilyreaganpr and on her podcast The Marketing Freelancer. 🎃 Come to the Halloween Networking Party! www.jointheplayhouse.com/party 📲 Grab the FREE Static 9 Grid Planner: deannaseymour.com/planner 🙅‍♀️ Grab the FREE Anti-Elevator Pitch Guide: deannaseymour.com/anti-elevator-pitch 🏠 Check out The Playhouse: A space for cool humans who happen to have businesses at jointheplayhouse.com

    Building Trust, Pricing for Profit, and Collaboration over Competition with Emily Reagan

  2. Sep 29

    Messaging That Respects Your Audience and Connects with Lara Eastburn

    Your sales page is a first date, treat them to the steak. Lara Eastburn shares why dropping the marketing “shoulds” and just telling the truth is your greatest sales tool, and how the right people will recognize themselves when your messaging finally matches up with reality. In this episode: 0:00 Why your website’s job is matchmaking, not convincing 2:00 The “virtual business suit” and why it ruins your messaging 5:44 How to strip away sales hacks and just tell the truth 7:15 The magic of helping people self-identify as a fit (or not) 13:44 Why long sales pages won’t make your offer more affordable We also kept the conversation going with a Live Q&A for where we talked about: Why you don’t need a lead magnet (seriously)When NOT to run Facebook adsWhere the best line on your website is probably hidingHow to talk about your business without making assumptions about your peopleWhy “ideal client avatars” can make your copy worse, not betterHang out with Lara: https://laraeastburn.com Hang out with Deanna: https://deannaseymour.com https://instagram.com/thedeannaseymour 🎃 Come to the Halloween Networking Party! www.jointheplayhouse.com/party 📲 Grab the FREE Static 9 Grid Planner: deannaseymour.com/planner 🙅‍♀️ Grab the FREE Anti-Elevator Pitch Guide: deannaseymour.com/anti-elevator-pitch 🏠 Check out The Playhouse: A space for cool humans who happen to have businesses at jointheplayhouse.com

    Messaging That Respects Your Audience and Connects with Lara Eastburn

  3. Sep 15

    How to Improve Your Customer’s User Experience with Nadia Rayward

    If people can’t figure out how to buy from you, or sign up for your events, or hit that dreaded 404 page you are losing sales. I’m chatting with Nadia Rayward from Sugar Beet Studios to chat all about user experience (UX) and why it matters for solopreneurs. In this episode: 02:01 What “user experience” really means (and why bad UX stands out) 04:33 The biggest “points of contact” you MUST consider for your business 06:58 Real-life example: handling waitlists, confirmations & why little details matter 10:42 How to actually TEST your experiences with real people (without fancy tools 13:03 The #1 thing visitors need to know on your homepage (in the first 5 seconds!) The extended episode with a live Q&A for Playhouse members includes: Where to actually put your call-to-action so people don't miss itWhy AI still can't replace real user testing, and what that means for youSimple, low-cost ways to test your website with real people before you launchListen to the extended version when you join us inside The Playhouse: https://jointheplayhouse.com Hang out with Nadia: https://www.sugarbeetstudios.com https://www.linkedin.com/in/nadiarayward https://sugarbeetstudios.kit.com/newsletter https://www.sugarbeetstudios.com/build-with-intention-monthly-meetup Hang out with Deanna: https://deannaseymour.com https://instagram.com/thedeannaseymour 🎃 Come to the Halloween Networking Party! www.jointheplayhouse.com/party 🙅‍♀️ Grab the FREE Anti-Elevator Pitch Guide: deannaseymour.com/anti-elevator-pitch 🏠 Check out The Playhouse: A space for cool humans who happen to have businesses at jointheplayhouse.com

    How to Improve Your Customer’s User Experience with Nadia Rayward

  4. Sep 3

    Anti-Elevator Pitch: Friendship-First Networking Without the Pressure for Small Business Owners

    This one thing might be the reason you hate networking, or think you suck at it. I'm breaking down my "anti-elevator pitch" and why friendship-first networking will get you further than any polished intro ever will. In this episode: 0:00 Why the classic elevator pitch makes you sweat and ramble 2:20 "Friendship first networking" — what it actually means 8:11 The 7-11 word intro formula: what you do + who you do it for 15:12 A no-pressure follow-up system for people who think they're bad at follow-up 19:23 Where to actually keep track of the people you meet (spoiler: it doesn't need to be a CRM) Grab the Anti-Elevator Pitch PDF guide: https://deannaseymour.com/anti-elevator-pitch Listen to the episodes mentioned: Trish Markel on systems: https://www.buzzsprout.com/2423323/episodes/19509750 Maria Medina on systems + follow-up: https://www.buzzsprout.com/2423323/episodes/19678904 Hang out with Deanna: https://deannaseymour.com https://jointheplayhouse.com https://instagram.com/thedeannaseymour 🎃 Come to the Halloween Networking Party! www.jointheplayhouse.com/party 📲 Grab the FREE Static 9 Grid Planner: deannaseymour.com/planner 🙅‍♀️ Grab the FREE Anti-Elevator Pitch Guide: deannaseymour.com/anti-elevator-pitch 🏠 Check out The Playhouse: A space for cool humans who happen to have businesses at jointheplayhouse.com

    Anti-Elevator Pitch: Friendship-First Networking Without the Pressure for Small Business Owners

  5. Sep 1

    Stop Confusing Being Busy for Being Productive with Maria Medina

    If you’ve ever felt like you’re always checking things off your list but your business isn’t moving forward, this episode will help you adjust that to-do list big time! Maria Medina breaks down how to tell if you’re actually being productive or just busy so your workday finally starts working for you. In this episode: 0:00 Why productivity and busy are not the same thing 2:31 How your calendar reveals your real priorities 5:35 The Eisenhower Matrix for prioritizing your to-dos 8:05 ADHD and the hidden productivity struggles business owners face 14:40 The one system you need to clarify your goals and actions We also kept the conversation going with a Live Q&A where we talked about: Why a "good" system can be as simple as Post-it Notes, and how to know if yours actually workThe ADHD-rooted reason follow-up feels so uncomfortable (and how to get past it)How to stop losing track of your best connections with a dead simple follow-up systemListen to the extended version when you join us inside The Playhouse: https://jointheplayhouse.com Hang out with Maria: https://www.instagram.com/mariamedinacoach https://www.linkedin.com/in/mariamedinacoach https://thecoachingnetwork.com Hang out with Deanna: https://deannaseymour.com https://instagram.com/thedeannaseymour 🎃 Come to the Halloween Networking Party! www.jointheplayhouse.com/party 📲 Grab the FREE Static 9 Grid Planner: deannaseymour.com/planner 🙅‍♀️ Grab the FREE Anti-Elevator Pitch Guide: deannaseymour.com/anti-elevator-pitch 🏠 Check out The Playhouse: A space for cool humans who happen to have businesses at jointheplayhouse.com

    Stop Confusing Being Busy for Being Productive with Maria Medina

  6. Aug 25

    Relational Intelligence for Better Collaborations and Teamwork with Cara Steinman

    If you’re obsessed with personality tests like Enneagram or Human Design, you’ll love hearing about Sheer Personality, a totally new (and super visual) way to understand how you and anyone in your life relate and work together. In this episode: 3:35 Why Cara created SHEER Personality and what makes it different 6:04 Using SHEER to overlay your results with friends, co-workers, or your partner 10:16 The five SHEER spectrums and what they actually mean 17:18 Cara shares how SHEER improved her marriage and work relationships 25:14 How understanding your "dark side" leads to empathy and growth Take the SHEER Assessment: https://sheerpersonality.com Hang out with Cara: https://carasteinmann.com https://getrhaina.com Hang out with Deanna: https://deannaseymour.com https://jointheplayhouse.com https://instagram.com/thedeannaseymour 🎃 Come to the Halloween Networking Party! www.jointheplayhouse.com/party 📲 Grab the FREE Static 9 Grid Planner: deannaseymour.com/planner 🙅‍♀️ Grab the FREE Anti-Elevator Pitch Guide: deannaseymour.com/anti-elevator-pitch 🏠 Check out The Playhouse: A space for cool humans who happen to have businesses at jointheplayhouse.com

    Relational Intelligence for Better Collaborations and Teamwork with Cara Steinman

  7. Aug 18

    Fun, Play, and Building a Business That Actually Feels Good with Steph DragonHeart Benedetto

    What if having more fun at work could actually help your business thrive? Steph DragonHeart Benedetto’s here to challenge the idea that play and productivity are opposites, and prove that a playful mindset can spark real results. In this episode: 0:00 Why we think play + productivity can’t mix (and what happens when they do) 2:26 How to redefine play so it fits your business and your personality 5:35 Choosing the “game” you want to play in your business 7:59 Why less pushing and stressing can actually make you more productive 10:28 Simple ways to spot opportunities for play, even if it doesn’t come naturally The extended episode with a live Q&A for Playhouse members includes: What “premature practicality” is and why it kills big ideaWhether you should focus on strategy before play if money’s tightHow to experiment with play in your work without feeling sillyHang out with Steph: https://www.theawakenedbusiness.com https://www.theawakenedbusiness.com/wildspire https://www.dragonheartquest.com https://www.linkedin.com/in/stephanierbenedetto https://www.youtube.com/@StephBenedetto Hang out with Deanna: https://deannaseymour.com https://instagram.com/thedeannaseymour 🎃 Come to the Halloween Networking Party! www.jointheplayhouse.com/party 🙅‍♀️ Grab the FREE Anti-Elevator Pitch Guide: deannaseymour.com/anti-elevator-pitch 🏠 Check out The Playhouse: A space for cool humans who happen to have businesses at jointheplayhouse.com

    Fun, Play, and Building a Business That Actually Feels Good with Steph DragonHeart Benedetto

  8. Aug 11

    How to Practice Joy Every Day as an Act of Rebellion with Ashley Looker

    If you ever feel overwhelmed by your to-do list and wonder how to squeeze more joy into your life (without making it another chore), this conversation I had with Ashley Looker is for you boo. Real talk, a little sassy, and maybe even some tears shed around the subject of joy and what it actually means to practice joy every day. In this episode: 2:29 Why joy is a practice and how to experiment with it 8:56 Joy as a “complete waste of time” (and why that’s powerful) 10:24 The rebellious act of choosing joy 19:00 Feeling “full” vs. feeling “fulfilled” in life 21:29 Joy is found in tiny everyday moments Hang out with Ashley: https://instagram.com/ashleylooker https://ashley-looker.com Hang out with Deanna: https://deannaseymour.com https://jointheplayhouse.com https://instagram.com/thedeannaseymour 🎃 Come to the Halloween Networking Party! www.jointheplayhouse.com/party 📲 Grab the FREE Static 9 Grid Planner: deannaseymour.com/planner 🙅‍♀️ Grab the FREE Anti-Elevator Pitch Guide: deannaseymour.com/anti-elevator-pitch 🏠 Check out The Playhouse: A space for cool humans who happen to have businesses at jointheplayhouse.com

    How to Practice Joy Every Day as an Act of Rebellion with Ashley Looker
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5
out of 5
16 Ratings

About

Humans evolve. Ideas change. And honestly, how is a creative human supposed to stick to one podcast idea for half a decade and a ton of episodes? I have no idea. That’s why Big Fun, Small Business is an audio sketchbook of all the things I’ve explored since starting back in 2020. It’s a collection of ideas, rants, pep talks, tips, and a very real evolution of what it looks like to build a business when your values are rooted in experimentation, creativity, and being true to yourself. Some episodes might have old ads to products I tried that don’t exist anymore. But for someone who started with a podcast called Imperfect Party, I say eff it.  This audio sketchbook celebrates the mistakes, the pivots, the tears. It’s a journey, and kind of a wild ride. Because no matter what a well oiled sales page tells you, running a business is hard, but it can also be a lot of fun. If you hear something you want to chat about, I’d genuinely love to hear from you. You can email me anytime at deannaseymour.com. And if you want to hang out beyond the podcast, you’re welcome to join my free community, The Playhouse, at jointheplayhouse.com. Happy listening! 🎉💖

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