UGLY TALK: THE ART HUSTLE IN CHICAGO
💡 What’s the Big Deal
The artist hustle is real—and it’s rarely pretty. From exploitation to burnout, underpayment to rejection, creatives face an uphill battle when pursuing their dreams. Join us for a raw, no-BS conversation about the ugly side of the art world and learn how to navigate it with resilience, strategic insight, and genuine support.
🧠 What You’ll Learn
Breaking In Without Burning Out: Tactics to sustain your craft, your sanity, and your bank account.
Rejection, Recognition & Revenue: Strategies for handling setbacks while building a name and a living.
Finding Your People: How to connect with the right collaborators, mentors, and creative communities.
Real Talk from Real Artists: Honest, unvarnished stories of struggle, success, and everything in between.
🎤 Who’s on the Panel
Panelists:
Grace Federighi - Artist, Photographer, Fashion Creative at Grace Federighi Art
Grace Federighi is a Polish-born painter, photographer and fashion creative who creates work emanating, mystery, edge and sophistication.
Inspired by both personal history and present experiences, Grace photographs models as reference images to explore themes of renewal, awakening and self-acceptance She selects images intuitively, drawn to a model's pose or the way a shadow falls across the skin. While some works follow a planned path, Grace often lets intuition lead, allowing charcoal’s raw spontaneity, color’s emotional resonance, or the texture of paint to guide her process. Blending various techniques and mediums, she refines figurative abstraction into timeless expressions of bold elegance.
Throughout her career, Grace has exhibited in both solo and group shows, including at the Polish Museum of America. Her work has been featured in Showhouse homes, and she has collaborated with local businesses, national retailers, interior designers, and curators. Her art has appeared on NETFLIX and HGTV, and she is currently represented in the Chicagoland area. Meaningfully engaged in her community, Grace actively donates her time and artwork to nonprofit organizations.
Grace’s lifestyle brand, LYLIA, is a natural extension of her artistic vision. Promoting the message “Live Your Life In Art,” it integrates her passions for interior design, wellness, and fashion.
“I’m often amazed—though not entirely surprised—by which of my works resonates with a viewer or collector. It reveals how deeply connected we are through our most personal and private emotions.”
Bob Spoerl - President & CEO of Bear Icebox Communications
With a knack for getting clients in the news and a passion for helping the underdog win, Bob has helped clients land coverage on/in the Wall Street Journal, New York Times, CNBC, CNN Money, the Associated Press, Fox Business, and the Chicago Tribune to name just a few.
His professional background is focused on B2B and franchise clients working in a variety of sectors: from tech startups to healthcare to restaurants and retail concepts.
Bob is a marketer with a background in journalism, which not only helps him gain earned media for clients, but also makes him an asset in the shared and owned media spaces.
He holds degrees in journalism from Northwestern University and English and Philosophy from Loyola University Chicago. When he’s not busy turning clients into sources, he’s with his family, running or playing guitar. Maybe even all at once.
Margaret Gillette - Partner at Curio
A former fashion designer who moved to NYC for a decade to have a successful intimates brand. Maggie then gained extensive organizational leadership experience when she launched and ran the most prominent independent intimates trade show for four years leading up to the pandemic.
At that time, she returned to her hometown of Chicago and, shortly thereafter, joined The Curio as a Principal in May of 2022. Her experiences as a designer and trade show owner perfectly complement Ian’s event-showcasing experiences. In addition to the above, Maggie is a freelance fashion, beauty, and lifestyle writer.
Dahlia Saper - Principal Attorney at Saper Law Offices, LLC
Daliah Saper is an Intellectual Property, Media & Entertainment, and Business Attorney who founded Saper Law in 2005. She is nationally recognized for handling trademark and copyright matters, complex contracts, and cutting-edge internet law issues like online defamation, cyberbullying, and revenge porn. Daliah gained international attention after representing a “catfishing” victim before the Illinois Supreme Court. She has served as an Adjunct Professor at Loyola University Chicago School of Law since 2010. Named to Crain’s “Most Influential Women Lawyers,” Daliah has also appeared on Super Lawyers' list for 16 consecutive years. Learn more: http://saperlaw.com/attorneys/
Moderator:
DeAnna Spoerl - Founder & Editor in Chief of Letty Sparrow
DeAnna Spoerl is a creative strategist, storyteller, and the co-owner of Bear Icebox Communications, a boutique PR agency helping brands turn bold ideas into headlines. With a background that spans fashion, tech, and entrepreneurship, she specializes in elevating emerging voices and underrepresented industries through media, events, and narrative clarity. She’s also the founder of Letty Sparrow, a platform spotlighting luxury fashion designers in Chicago, and a contributor to Entrepreneur magazine, where she writes about leadership, belief, and business breakthroughs.
DeAnna’s work centers on helping people and brands build confidence, communicate clearly, and show up with purpose. Known for her straight talk, sharp instincts, and ability to bridge creative vision with strategic execution, she’s helped companies grow—from scrappy startups to award-winning agencies. Whether she’s producing a panel, curating a fashion event, or consulting founders on their brand story, DeAnna leads with authenticity and intention.
When she’s not working, you’ll find her practicing yoga, styling outfits, or hanging out with her husband and two kids in Chicago.
👥 Who Else Is Going
Artists, performers, and creatives navigating industry challenges
Arts organizations, curators, and supporters of emerging talent
Anyone craving a behind-the-scenes look at the creative grind
Folks who value authenticity over perfection
🎯 Why You Should Attend
Gain Battle-Tested Tools: Learn practical strategies to push through common creative roadblocks.
Build Community: Connect with artists who truly understand the ups and downs of the creative journey.
Get Inspired: Walk away with real stories, lessons learned, and actionable ideas to keep creating.
No Sugar-Coating Allowed: Ugly Talk delivers genuine narratives, honest mistakes, and groundbreaking breakthroughs.
🤝 Co-Hosted By
Bear Icebox - a full-service PR agency you’re looking for to position, amplify and boost your brand story.
Trendsapio - Trendsapio connects diverse talent from creative industries with brands that need fresh ideas.
GREY Journal – Media partner spotlighting modern entrepreneurs.
🤝 Brand Partner
The Yard - Private offices & coworking spaces for individuals and teams.
🎥 Event Vibes
Get a taste of past Ugly Talk energy:
https://www.youtube.com/watch?v=moMfGsBPjpE
⭐ About Ugly Talk
Started in 2019, Ugly Talk has been transforming business setbacks into breakthrough “aha!” moments by hosting unfiltered, no-nonsense events where battle-tested entrepreneurs share their raw lessons and insights.
With a growing presence in cities like New York, Chicago, San Francisco, and Miami, we’ve built a vibrant community of thousands of founders and industry leaders making a profound impact on the entrepreneurial landscape.