Could Be Pretty Cool

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101

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Oct 2026

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About the show

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. Join our creator community at prettycoolcommunity.com couldbeprettycoolnews.substack.com

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October 8, 202627 min

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

Description: Simone D'Antonio, founder of the Italian edibles brand MAMAMIA, 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 MAMAMIA, 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: saymamamia.com and @saymamamia 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 This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit couldbeprettycoolnews.substack.com

September 24, 202622 min

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 This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit couldbeprettycoolnews.substack.com

September 17, 202632 min

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 This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit couldbeprettycoolnews.substack.com

September 10, 202621 min

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 This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit couldbeprettycoolnews.substack.com

September 3, 202611 min

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 This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit couldbeprettycoolnews.substack.com

August 27, 202625 min

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 This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit couldbeprettycoolnews.substack.com

August 20, 202627 min

Melba Moore and the Art of the Lifelong Career

Description: In this special episode, Kacie sits down with the legendary Melba Moore, Tony Award-winning actress, recording artist, and entrepreneur, whose career spans more than five decades. With a new memoir, This Is It: Marvelous and Getting Better, and new music out now, Melba shares what it takes to build a creative life that lasts. What starts as an interview turns into something closer to a masterclass on knowing yourself, and the conversation lands somewhere neither of them expected. Key Topics: Breaking barriers and the reality of being the first in a space Managing pressure, fear, and self-doubt as a creative Finding your own pacing and avoiding burnout Building an authentic connection with audiences beyond algorithms Stillness, reflection, and knowing your own voice Reinventing yourself as an independent artist Creating generational entrepreneurship within a family Health, longevity, and sustaining a lifelong creative career Featured Guest: Melba Moore - Tony Award-winning actress; recording artist; entrepreneur; author of This Is It: Marvelous and Getting Better Notable Quotes: "You're not gonna get over it. Go anyway." - Melba Moore "You're evolving. You're not trying to remain back where you were. You got to move forward." - Melba Moore Connect with our guest: Melba Moore: https://www.iammelbamoore.com/ Instagram: https://www.instagram.com/melba1moore/ Follow Could Be Pretty Cool: @couldbeprettycool | couldbeprettycool.com | couldbeprettycoolnews.substack.com Keywords: Melba Moore, Tony Award, Broadway, creative longevity, independent artist, creative entrepreneurship, breaking barriers, artist wellness, burnout, memoir, music industry, lifelong creative career Learn more about your ad choices. Visit megaphone.fm/adchoices This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit couldbeprettycoolnews.substack.com

August 14, 202628 min

Old Time, New Paths with Annick Odom

Description: What does a thriving creative scene look like in Morgantown, West Virginia? Folk singer, bassist, and clarinetist Annick Odom takes us inside the old time music community that pulled her home from across an ocean, introduces an art form you've probably never heard of, and shares how community projects became the foundation of a creative career built on her own terms. Key Topics: Old time music and Appalachian jam culture Crankies and reviving pre-film storytelling Building a creative career around community projects and grant support The gig filter: good money, good people, good time Balancing a full-time job with a serious creative practice Freelancer safety nets in the Netherlands versus the US Separating being good at something from it being worthwhile to do Making local, in-person art in the age of AI and streaming Apprenticing with master traditional artists Featured Guest: Annick Odom is a Belgian American folk singer, bassist, and clarinetist based in Morgantown, West Virginia. She organizes square dances and a crankie festival in her community, apprentices with master traditional artists in Appalachia, and performs everything from orchestral repertoire to experimental bass and voice music. Her latest album is Linen of Words. Notable Quotes: "The more that AI comes into our lives, the more that I just wanna make art that AI would never." (Annick Odom) "Is it a good amount of money? Is it good people? Is it a good time? And if it doesn't have two of those things, say no." (Annick Odom) Connect with our guest: Find Annick Odom on Bandcamp and streaming platforms. Her latest album is Linen of Words. Follow Could Be Pretty Cool: @couldbeprettycool | couldbeprettycool.com | couldbeprettycoolnews.substack.com Keywords: old time music, Appalachian folk, West Virginia arts, community music, creative career sustainability, crankies, folk musician, experimental music, creative economy, artist grants, square dancing, traditional arts Learn more about your ad choices. Visit megaphone.fm/adchoices This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit couldbeprettycoolnews.substack.com

July 30, 202630 min

Building From the Ground Up with Nick Khamsopa

A kid from Thailand lands at JFK, looks up at the towers in Manhattan for the first time, and decides he's going to figure out how to build one of those. Nick Khamsopa is now an affordable housing developer in New York's Hudson Valley and the founder of Hudson Housing Lifestyle, working inside the state's push to build 800,000 units by 2030. This conversation covers the long road from union apprenticeship to land development, the project that made him realize he was on the wrong side of the deal, and why he thinks the only real business education is the kind you get from failing. Key Topics: Learning entrepreneurship through trial, error, and repeated failure Moving from construction and contracting into land development Recognizing who is actually capturing the value in a deal How New York State's affordable housing initiative and subsidies work What affordable housing really means, and the misconceptions around it Building a business on relationships and mutual benefit Union roots, local labor, and keeping money in the community Marketing and visibility as a founder who'd rather stay behind the camera Featured Guest: Nick Khamsopa (Affordable housing developer and founder of Hudson Housing Lifestyle in New York's Hudson Valley) Notable Quotes: "You can't go to school and learn it. You have to go out and fail." (Nick Khamsopa) "The more you fail, the more knowledge you'll gain." (Nick Khamsopa) "Some of the buildings I built 30 years ago, I drive by and I still get goosebumps." (Nick Khamsopa) "Money is great, but if you don't enjoy it, money is not gonna make you happy." (Nick Khamsopa) Connect with our guest: Nick: hudsonlifestyle.com and Hudson Housing Lifestyle on Instagram Follow Could Be Pretty Cool News: @couldbeprettycool | couldbeprettycool.com | couldbeprettycoolnews.substack.com Keywords: affordable housing, real estate development, creative entrepreneurship, Hudson Valley, New York housing, construction industry, union labor, land development, workforce housing, founder story, business networking, entrepreneurship advice Learn more about your ad choices. Visit megaphone.fm/adchoices This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit couldbeprettycoolnews.substack.com

July 23, 202628 min

Ralph Rolle on Living Without a Plan B

Description Ralph Rolle has spent his career refusing to have a backup plan. He's a professional drummer currently touring with Nile Rodgers, the founder of Soul Snacks Cookie Company, and the builder of multiple digital platforms serving creators and families. In this conversation, he talks about what it takes to keep moving when there's no safety net, why he believes your family stories are a form of generational wealth, and how the tools to build almost anything are already sitting in your pocket. Key Topics Choosing a creative career against family expectations Building confidence and showing up prepared in professional settings The five Ps framework for creative and business practice Launching a food business from a home kitchen and scaling to national retail Preserving family legacy and stories as generational wealth Rethinking how artists get paid in a streaming economy Using AI and no code tools to build ideas without a developer Setting deadlines and beating procrastination Featured Guest Ralph Rolle. Professional drummer and touring musician with Nile Rodgers. Founder of Soul Snacks Cookie Company. Founder of Dear Family Stories and Fund With Music. Global ambassador for Wish For Life. Former A&R manager at Jive Records. Master class instructor. Notable Quotes "I live by there's no plan B because in my mind, if you have a plan B, you're not gonna focus 100% on your plan A." Ralph Rolle "We have the keys to the castle now. We can get any information on anything at any time in the palm of your hand." Ralph Rolle "Your generational wealth is in your family legacy." Ralph Rolle Connect with Ralph Website: ralphrolle.com Social: @Drumroll Dear Family Stories: dearfamilystories.com Fund With Music: fuwimu.com Wish For Life: wishnumberforlife.org Follow the Show @couldbeprettycool | couldbeprettycool.com | couldbeprettycoolnews.substack.com Keywords creative entrepreneurship, serial entrepreneur, professional musician, music industry, Nile Rodgers, family legacy, generational wealth, food business, digital platforms, artist compensation, streaming economy, AI tools for creators, master classes, creative career pivot Learn more about your ad choices. Visit megaphone.fm/adchoices This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit couldbeprettycoolnews.substack.com