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Could Be Pretty Cool

Author: Could Be Pretty Cool

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Could Be Pretty Cool (formally Could Be Pretty Cool News) is a podcast featuring conversations with creators and innovators across arts, culture, tech, education, entrepreneurship, sustainability and beyond. Each episode brings you real stories from people doing interesting work, whether they're rethinking creative industries, building community through art, launching passion projects, or finding new ways to make a living doing what they love. Our mission is to amplify the voices of people building something meaningful and share the practical wisdom that helps others do the same.

Learn more at couldbeprettycool.com.



74 Episodes
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Description: Kendra Walker founded Atlanta Art Week to put the city's galleries, artists and institutions in front of audiences who weren't looking for them yet. Several editions later, she's taking a step back to figure out what comes next. In this conversation she's candid about what the work cost her, what the arts community gets wrong about who deserves credit, and why a pause can be the smartest business decision a founder makes. Key Topics: Building a citywide arts event from a personal network Capital as infrastructure, not a nice to have The real line items behind a grassroots event Charging from day one versus proving the concept for free Who gets listened to in a creative scene, and who does the actual organizing Reading participation numbers as information Deciding when to pause, pivot or keep going Application based participation models and why organizers use them Atlanta's place in the national art ecosystem Featured Guests: Kendra Walker, founder of Atlanta Art Week, arts advisor and writer, Georgia State University (psychology, fine art minor) Notable Quotes: "You need money. I lost money believing in this initiative, and it paid out in certain ways, but you have to put money up to take a chance." (Kendra Walker) "If you want respect, you have to give respect. It doesn't matter someone's age. If they're doing the work, you have to respect them." (Kendra Walker) "If the community's not backing it, it doesn't make sense to keep producing and pushing out things if the numbers aren't adding up." (Kendra Walker) Connect with our guest: Kendra Walker on LinkedIn Atlanta Art Week: atlantaartweek.co | @theatlantaartweek Follow Could Be Pretty Cool: @couldbeprettycool | couldbeprettycool.com | couldbeprettycoolnews.substack.com Keywords: Atlanta Art Week, Atlanta art scene, arts ecosystem, creative entrepreneurship, cultural infrastructure, founder pivot, grassroots events, arts funding, gallery ecosystem, independent curators, event sustainability, creative economy Learn more about your ad choices. Visit megaphone.fm/adchoices
Description: Keith McHenry spent his youth working in a Cambridge grocery store and studying art before co-founding Food Not Bombs, a global movement that shares free vegan meals to protest war, poverty, and state violence. Over four decades later, despite facing state surveillance, FBI terror designations, and over a thousand arrests, Keith continues to champion autonomous, community-led care. In this conversation, he discusses the intersection of creative activism and street theater, why authorities fear simple acts of community solidarity, how punk culture helped expand the movement to over 1,000 cities worldwide, and why direct mutual aid remains one of the most powerful tools for social change. Key Topics: The origins of Food Not Bombs and its growth from Boston to San Francisco Blending art, street theater, and humor with direct action activism Navigating state surveillance, FBI Joint Terrorism Task Force filings, and mass arrests The three core principles: free vegan food, non-hierarchical consensus, and nonviolent direct action How touring punk bands helped spread the movement across Asia, Europe, and the Americas Why avoiding foundation grants preserves organizational independence and longevity Reclaiming humanity and compassion through practical, local community support Featured Guest: Keith McHenry is an artist, author, and co-founder of Food Not Bombs. Since 1980, he has dedicated his life to nonviolent direct action, organizing mutual aid initiatives, and supporting autonomous activist chapters in over 1,000 cities globally. He is the author of several books, including his memoir Soup Street and the organizing guide Hungry for Peace. Notable Quotes: "The fear of a good idea is what threatens the people in power the most." (Keith McHenry) "Maybe what the revolution is is that we're taking care of one another in this kind of form of mutual aid..." (Keith McHenry) "There's this deep thing in humans where we just can't be put down." (Keith McHenry) Connect with Keith: foodnotbombs.net | keithmckenry.net | keithmckenry.substack.com | anarchistcook.blog Follow Could Be Pretty Cool News: @couldbeprettycool | couldbeprettycool.com | couldbeprettycoolnews.substack.com Keywords: Food Not Bombs, Keith McHenry, mutual aid, direct action, street theater, grassroots activism, veganism, anti-war movement, Soup Street, social justice, autonomous chapters, community care, creative activism Learn more about your ad choices. Visit megaphone.fm/adchoices
Description: Marjorie Guyon spent decades as an exhibiting artist before she turned her attention to public space and started the I Was Here project, an initiative that installs ancestor portraits in civic places and asks people to reconsider who built this country. In this conversation she talks about keeping ambitious work alive when the money is far from guaranteed, why the way we talk about supporting artists underestimates the people doing the work, and what she would tell anyone sitting on an idea they are afraid to start. Key Topics: Reconsidering who has access to powerful art and where it lives Building public art projects without funding or permission The power of ancestry as a frame, rather than the wound of ancestry Sustaining nonprofit creative work in a shifting funding environment Trust-based grantmaking and what it makes possible for small organizations Expanding a project from a single city into a regional and national initiative Advice for creatives holding an idea they have not started yet Finding collaborators and partners who take the work seriously Featured Guest: Marjorie Guyon is an artist and the founder of the I Was Here project, based in Lexington, Kentucky. After 25 years exhibiting nationally, she turned to public art, creating a set of ancestor spirit portraits installed in the windows surrounding Lexington's historic courthouse. The project has since grown to include the Nation Builders workshop program and is expanding across the South. Notable Quotes: "As long as you operate out of the wound, you stay small." (Marjorie Guyon) "The whole idea is you will not succeed. You will need to be supported, and the fact is there's no guarantees. You have to create them." (Marjorie Guyon) "The arts are muscular, but you have to make them do what you want them to do." (Marjorie Guyon) Connect with Marjorie: i-was-here.org Follow Could Be Pretty Cool News: @couldbeprettycool | couldbeprettycool.com | couldbeprettycoolnews.substack.com Keywords: public art, Marjorie Guyon, I Was Here project, Lexington Kentucky, ancestor portraits, arts nonprofit funding, trust-based philanthropy, South Arts, creative entrepreneurship, artist advice, community art, Southern arts, cultural sustainability, nation builders Learn more about your ad choices. Visit megaphone.fm/adchoices
Description: Could Be Pretty Cool is expanding its community education work with phase two of the Pretty Cool Creator Collective, and this bonus episode introduces the two people teaching alongside Kacie. Kiki (Kiki Said So) Walker has spent about a decade in podcasting and is tackling the thing that intimidates most audio people right now: video. Christina Lee came up through print journalism and has since worked on some of the most talked about audio documentaries to come out of Atlanta. Both of them arrived at podcasting in ways they did not plan for, and both are bringing something specific to this cohort. If you have been thinking about starting a show, or you have started one and gotten stuck, this is a look at what phase two actually covers and who you would be learning from. Key Topics: What phase two of the Pretty Cool Creator Collective includes Making video podcasting work on a zero dollar budget Scaling video content without hiring a full team Applying journalism storytelling fundamentals to any show format Organizing research and thoughts before you record Why most indie podcasters should not lead with ad revenue Finding grants, fellowships, and alternative funding for your show Building a show around a busy life Repurposing panels, events, and local opportunities into content Learning in cohort with people at different experience levels Featured Guests: Kiki (Kiki Said So) Walker, host of Cocktails with Kiki, podcast producer, Howard University alum Christina Lee, journalist and audio producer, credits include Bottom of the Map, King Slime: The Prosecution of Young Thug and YSL, and Atlanta Is Notable Quotes: "While it's hard and it's hard work, it's not out of reach." (Kiki Walker) "The fundamentals of storytelling really count, especially when you're trying to be the sort of presence that everybody's gonna wanna turn to." (Christina Lee) "There is room out here for everyone, and we want everyone to be able to do well." (Kacie) Connect with our guests: Kiki: Instagram @kikisaidso Christina: Instagram @bychristinalee Join the Pretty Cool Creator Collective:couldbeprettycool.com/creatorcollectiveprettycoolcommunity.com Follow Could Be Pretty Cool: @couldbeprettycool | couldbeprettycool.com | couldbeprettycoolnews.substack.com Support our mission to build a more equitable creative economy: https://couldbeprettycool.betterworld.org/donate?utm_source=qr&utm_medium=print Keywords: podcasting education, video podcasting, indie podcasting, podcast cohort, storytelling fundamentals, Atlanta podcast community, podcast funding, creator education, Pretty Cool Creator Collective, media entrepreneurship, audio journalism Learn more about your ad choices. Visit megaphone.fm/adchoices
Description: Every creator trades a little privacy for reach. Tiffany Wisconsin, known online as Wisconsin Tiff, has thought about that trade more than most. She built her business on daily live streams and a subscriber strategy she reverse engineered herself, and she has since had to rethink where she goes, what she posts, and who she lets near her door. In this conversation she talks about the system behind her growth, how she timed her exit from a day job, and what she wishes fans understood about the difference between watching someone work and having access to them. Useful listening for anyone building an audience online. Note: This episode includes discussion of stalking, personal safety, and family loss. Key Topics: Building a subscriber base through daily live streaming Developing a live stream strategy for low engagement days Treating creative growth as a sequence rather than a shortcut Knowing when income is consistent enough to leave a day job Privacy and physical safety as a public facing creator Setting boundaries with fans who confuse visibility with access Rethinking daily habits, travel, and location sharing Industry recognition and what awards confirm Staying motivated while managing real risk Featured Guest: Tiffany Wisconsin (Wisconsin Tiff) is an adult content creator based in Wisconsin. She built her business primarily through OnlyFans and TikTok live streaming and has been recognized with industry awards, including an XBIZ Award. Notable Quotes: "It's almost like a pyramid and a domino effect. You're not just going from here to there. Everything is built up." (Tiffany Wisconsin) "They say, 'Well, that's what you asked for joining the industry,' and it's not what I asked for. That's an excuse for you to go against my boundaries." (Tiffany Wisconsin) "I wish they would understand there's a time and place for everything." (Tiffany Wisconsin) Connect with our guest: Tiffany Wisconsin (Wisconsin Tiff): TikTok Follow Could Be Pretty Cool: @couldbeprettycool | couldbeprettycool.com | couldbeprettycoolnews.substack.com Support the Show: If you'd like to help support Could Be Pretty Cool's mission of building a more equitable creative economy, you can make a tax deductible donation HERE Keywords: creator economy, content creator safety, online privacy, adult content industry, OnlyFans creator, live streaming strategy, audience building, creator boundaries, stalking and safety, independent business building, TikTok growth, creator burnout, women entrepreneurs Learn more about your ad choices. Visit megaphone.fm/adchoices
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