Could Be Pretty Cool

Could Be Pretty Cool
  • 5.0 (3)
  • Arts
  • Biweekly

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.

  1. 1d ago

    Decide, Then Build: Talib Jasir on a Decade in Podcasting

    Description: Talib Jasir, founder of the Afros and Audio Podcast Festival and the Vanguard Podcast Network, joins us to talk about nearly a decade of building in podcasting. His story starts with a love of radio drama and a habit of deciding to do something before he knows exactly how, and it has led to some firsts he didn’t even know about until recently. We talk about his new platform for audio drama creators, where the line falls between a podcast and everything else, and why he believes independent creators hold more power in this industry than they realize. Key Topics: · Discovering audio drama as a modern creative medium · Starting before you have all the answers · Building a conference for and by Black independent podcasters · Taking a break after years of nonstop work · Audio drama as portfolio building for film and TV creatives · What makes a podcast in a video-first landscape · Why the future of podcasting depends on independent creators · Podcasting as a living record of who we are Featured Guest: · Talib Jasir - Founder of the Afros and Audio Podcast Festival, Vanguard Podcast Network, and Down the Road Media Notable Quotes: “I believe that we are, as podcasters, laying down a living record of who we are today.” (Talib Jasir) “I think we have an opportunity if only we know how powerful we are in this industry, because without our content, this industry can’t even move.” (Talib Jasir) Connect with our guest: · Talib: talibjasir.com, vanguardpn.com, afrosandaudio.com, and DowntheRoad.Media · Social: Talib Jasir and Afros and Audio Follow Could Be Pretty Cool: @couldbeprettycool | couldbeprettycool.com | couldbeprettycoolnews.substack.com Keywords: podcasting, audio drama, independent podcasters, Black podcasters, podcast industry, creator economy, scripted fiction, podcast festival, creative careers, storytelling Learn more about your ad choices. Visit megaphone.fm/adchoices

  2. Oct 23

    Lee on Business, Hip Hop, and Making Music for the Love of It

    Description: Hip hop artist Lee joins us to talk about the songs he’s been writing since he was a kid and the long road to finally releasing them. With a background in business and finance, Lee expected to have a head start in the music industry, and he shares what actually happened when he brought that mindset into the studio. We also talk about his influences, the realities of being an independent artist right now, and his advice for young people who want to make music without losing the ability to take care of themselves. Key Topics: · Holding onto a creative passion through years of self-doubt · Writing music rooted in storytelling, culture, and lived experience · Bringing corporate business skills into the music industry · Learning the culture of a new creative space · Social media, streaming, and the independent artist · Balancing a day job with a serious creative practice · Building real craft over chasing viral moments Featured Guest: · Lee - Hip hop artist and songwriter with a lyric-focused, storytelling style; new project coming soon Notable Quotes: “I do this because I just really, really love it... if you do it for free, then you truly love it, and that’s kind of where I am right now.” (Lee) “Focus on really building your craft... because when it’s real, that’s what people are going to respond to most.” (Lee) Connect with our guest: · Lee: @lee___music on Instagram, and his music is available on all major streaming platforms Follow Could Be Pretty Cool: @couldbeprettycool | couldbeprettycool.com | couldbeprettycoolnews.substack.com Keywords: hip hop, independent music, rap, songwriting, music business, creative careers, day job and creativity, music industry, streaming, sustainable creative careers Learn more about your ad choices. Visit megaphone.fm/adchoices

  3. Oct 8

    Simone D'Antonio on Taste, Design, and Calculated Risk

    Description: Simone D'Antonio, founder of the Italian edibles brand MAMMAMIA, joins us to talk about turning a culinary tour of Italy into a cannabis brand. He shares what it took to start before he knew what he was getting into, how customers reshaped his original vision, and the thinking behind a product designed to get people talking. This is a conversation about creative entrepreneurship in a type of business we haven't featured on the show before, and the challenges will sound familiar to founders in any industry. Key Topics: · Spotting a gap and deciding you can do it better · Building a brand around taste, design, and Italian culture · Adapting a creative vision to what customers actually buy · Taking calculated risks with product and marketing · Navigating state and federal cannabis regulation · Persevering through the highs and lows of founding a company Featured Guest: · Simone D'Antonio - Founder of MAMMAMIA, an Italian edibles brand based in California Notable Quotes: "I can do something that tastes better than this, looks better than this... So I focus on branding and the actual recipe." (Simone D'Antonio) "Every business is like a roller coaster... You just focus on that beautiful bigger picture that you have in your mind, and you don't care about the bad days." (Simone D'Antonio) Connect with our guest: · Simone: saymammamia.com and @saymammamia on Instagram Follow Could Be Pretty Cool: @couldbeprettycool | couldbeprettycool.com | couldbeprettycoolnews.substack.com Keywords: creative entrepreneurship, cannabis edibles, hemp edibles, Italian food, brand building, product development, food entrepreneurship, cannabis regulation, calculated risk, startup founders Learn more about your ad choices. Visit megaphone.fm/adchoices

  4. Sep 24

    Respect the Organizer: Kendra Walker on Atlanta Art Week

    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

  5. Sep 17

    Fear of a Good Idea: Keith McHenry on Food Not Bombs

    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

  6. Sep 10

    The Arts Are Muscular: Marjorie Guyon on the I Was Here Project

    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

  7. Sep 3 ·  Bonus

    Meet the Pretty Cool Creator Collective Instructors

    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

  8. Aug 27

    Building and Boundaries with Wisconsin Tiff

    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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Ratings & Reviews

5
out of 5
3 Ratings

About

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.

Information

  • Creator
    Could Be Pretty Cool
  • Years Active
    2024 - 2026
  • Episodes
    77
  • Rating
    Clean
  • Show Website
    Could Be Pretty Cool